JP3459659B2 - イミダゾ−縮合の同素環および複素環 - Google Patents
イミダゾ−縮合の同素環および複素環Info
- Publication number
- JP3459659B2 JP3459659B2 JP24346992A JP24346992A JP3459659B2 JP 3459659 B2 JP3459659 B2 JP 3459659B2 JP 24346992 A JP24346992 A JP 24346992A JP 24346992 A JP24346992 A JP 24346992A JP 3459659 B2 JP3459659 B2 JP 3459659B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- compound
- sio
- title compound
- formula
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Lifetime
Links
- 125000000623 heterocyclic group Chemical group 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 241
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 58
- -1 n- butyl Chemical group 0.000 claims description 44
- 239000001257 hydrogen Substances 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 150000002431 hydrogen Chemical class 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 14
- 150000003839 salts Chemical class 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 230000029936 alkylation Effects 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 239000002333 angiotensin II receptor antagonist Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 5
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 4
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 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 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000005936 piperidyl group Chemical group 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- 229940126317 angiotensin II receptor antagonist Drugs 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 125000006413 ring segment Chemical group 0.000 abstract description 11
- 102000008873 Angiotensin II receptor Human genes 0.000 abstract description 4
- 108050000824 Angiotensin II receptor Proteins 0.000 abstract description 4
- 239000005557 antagonist Substances 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 165
- 229910004298 SiO 2 Inorganic materials 0.000 description 97
- 239000000243 solution Substances 0.000 description 91
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 54
- 238000000034 method Methods 0.000 description 50
- 238000002844 melting Methods 0.000 description 39
- 230000008018 melting Effects 0.000 description 39
- 239000000460 chlorine Substances 0.000 description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 30
- 239000011734 sodium Substances 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 23
- 238000004587 chromatography analysis Methods 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 229920006395 saturated elastomer Polymers 0.000 description 21
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 20
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- 239000000126 substance Substances 0.000 description 16
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 15
- 229910052736 halogen Inorganic materials 0.000 description 15
- 150000002367 halogens Chemical class 0.000 description 15
- 238000010992 reflux Methods 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
- 239000012141 concentrate Substances 0.000 description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 12
- 229950006323 angiotensin ii Drugs 0.000 description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 10
- 125000004076 pyridyl group Chemical group 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 102000005862 Angiotensin II Human genes 0.000 description 9
- 101800000733 Angiotensin-2 Proteins 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 108020003175 receptors Proteins 0.000 description 9
- 102000005962 receptors Human genes 0.000 description 9
- 125000004093 cyano group Chemical group *C#N 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 239000002287 radioligand Substances 0.000 description 8
- 229910052786 argon Inorganic materials 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- HEGXUBFMGZWSNA-UHFFFAOYSA-N amino 3-nitrobenzoate Chemical compound NOC(=O)C1=CC=CC([N+]([O-])=O)=C1 HEGXUBFMGZWSNA-UHFFFAOYSA-N 0.000 description 5
- 125000002619 bicyclic group Chemical group 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000006260 foam Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- LENLQGBLVGGAMF-UHFFFAOYSA-N tributyl([1,2,4]triazolo[1,5-a]pyridin-6-yl)stannane Chemical compound C1=C([Sn](CCCC)(CCCC)CCCC)C=CC2=NC=NN21 LENLQGBLVGGAMF-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 230000036772 blood pressure Effects 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 238000001990 intravenous administration Methods 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 229940124530 sulfonamide Drugs 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 description 3
- XWWJWZJOSWSJQV-UHFFFAOYSA-N 2-ethyl-5,7-dimethyl-1h-imidazo[4,5-b]pyridine Chemical compound CC1=CC(C)=C2NC(CC)=NC2=N1 XWWJWZJOSWSJQV-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- HXBPYFMVGFDZFT-UHFFFAOYSA-N allyl isocyanate Chemical group C=CCN=C=O HXBPYFMVGFDZFT-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- AOCYHPQXGJBAQQ-UHFFFAOYSA-N ethyl n-sulfonylcarbamate Chemical group CCOC(=O)N=S(=O)=O AOCYHPQXGJBAQQ-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000004108 freeze drying Methods 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- 210000004185 liver Anatomy 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000700 radioactive tracer Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000000638 stimulation Effects 0.000 description 3
- 150000003456 sulfonamides Chemical class 0.000 description 3
- LGPFFMMQIUXISP-UHFFFAOYSA-N 1-[2-[4-[(2-ethyl-7-methylimidazo[4,5-b]pyridin-3-yl)methyl]phenyl]phenyl]sulfonyl-3-propylurea Chemical compound CCCNC(=O)NS(=O)(=O)C1=CC=CC=C1C(C=C1)=CC=C1CN1C2=NC=CC(C)=C2N=C1CC LGPFFMMQIUXISP-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- BZKBOWJBYJIIDF-UHFFFAOYSA-N 2-butyl-3-[(2-carboxy-3-chloro-1-benzothiophen-6-yl)methyl]benzimidazole-4-carboxylic acid Chemical compound C1=C2C(Cl)=C(C(O)=O)SC2=CC(CN2C3=C(C(O)=O)C=CC=C3N=C2CCCC)=C1 BZKBOWJBYJIIDF-UHFFFAOYSA-N 0.000 description 2
- HJYAVTRUWVKPII-UHFFFAOYSA-N 2-butyl-3-[(3-carboxy-2-phenylimidazo[1,2-a]pyridin-7-yl)methyl]benzimidazole-4-carboxylic acid Chemical compound CCCCC1=NC2=CC=CC(C(O)=O)=C2N1CC(=CC1=N2)C=CN1C(C(O)=O)=C2C1=CC=CC=C1 HJYAVTRUWVKPII-UHFFFAOYSA-N 0.000 description 2
- FZESPVBONPPRAW-UHFFFAOYSA-N 2-methyl-1h-imidazo[4,5-b]pyridine Chemical compound C1=CC=C2NC(C)=NC2=N1 FZESPVBONPPRAW-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- YFHAHGSQHGPKRV-UHFFFAOYSA-N 5-(2-butylimidazo[4,5-b]pyridin-3-yl)-2-(4-methylphenyl)-3-(2h-tetrazol-5-yl)imidazo[4,5-b]pyridine Chemical compound CCCCC1=NC2=CC=CN=C2N1C(N=C1N2C=3NN=NN=3)=CC=C1N=C2C1=CC=C(C)C=C1 YFHAHGSQHGPKRV-UHFFFAOYSA-N 0.000 description 2
- HAVNKTJDVVAOOB-UHFFFAOYSA-N 6-[(2-butylimidazo[4,5-b]pyridin-3-yl)methyl]-3-chloro-1-benzothiophene-2-carboxylic acid Chemical compound C1=C2C(Cl)=C(C(O)=O)SC2=CC(CN2C3=NC=CC=C3N=C2CCCC)=C1 HAVNKTJDVVAOOB-UHFFFAOYSA-N 0.000 description 2
- FZZOEWNUHXOMRZ-UHFFFAOYSA-N 7-[(2-butylimidazo[4,5-b]pyridin-3-yl)methyl]-2-phenylimidazo[1,2-a]pyridine-3-carboxylic acid Chemical compound CCCCC1=NC2=CC=CN=C2N1CC(=CC1=N2)C=CN1C(C(O)=O)=C2C1=CC=CC=C1 FZZOEWNUHXOMRZ-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- PZASAAIJIFDWSB-CKPDSHCKSA-N 8-[(1S)-1-[8-(trifluoromethyl)-7-[4-(trifluoromethyl)cyclohexyl]oxynaphthalen-2-yl]ethyl]-8-azabicyclo[3.2.1]octane-3-carboxylic acid Chemical compound FC(F)(F)C=1C2=CC([C@@H](N3C4CCC3CC(C4)C(O)=O)C)=CC=C2C=CC=1OC1CCC(C(F)(F)F)CC1 PZASAAIJIFDWSB-CKPDSHCKSA-N 0.000 description 2
- 101800000734 Angiotensin-1 Proteins 0.000 description 2
- 102400000344 Angiotensin-1 Human genes 0.000 description 2
- 102100030988 Angiotensin-converting enzyme Human genes 0.000 description 2
- 108010039627 Aprotinin Proteins 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
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- RTYQUIUUJDQGFG-UHFFFAOYSA-N methyl 2-butyl-3-[[4-[2-(ethoxycarbonylsulfamoyl)phenyl]phenyl]methyl]benzimidazole-4-carboxylate Chemical compound CCCCC1=NC2=CC=CC(C(=O)OC)=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1S(=O)(=O)NC(=O)OCC RTYQUIUUJDQGFG-UHFFFAOYSA-N 0.000 description 1
- UZIDUCBUOIGLJJ-UHFFFAOYSA-N methyl 2-butyl-3-[[4-[2-(ethylcarbamoylsulfamoyl)phenyl]phenyl]methyl]benzimidazole-4-carboxylate Chemical compound CCCCC1=NC2=CC=CC(C(=O)OC)=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1S(=O)(=O)NC(=O)NCC UZIDUCBUOIGLJJ-UHFFFAOYSA-N 0.000 description 1
- VPRPZAPGAGSCAL-UHFFFAOYSA-N methyl 3-nitro-2-(pentanoylamino)benzoate Chemical compound CCCCC(=O)NC1=C(C(=O)OC)C=CC=C1[N+]([O-])=O VPRPZAPGAGSCAL-UHFFFAOYSA-N 0.000 description 1
- CPIOBMFNASQBPI-UHFFFAOYSA-N methyl 6-[(2-butylimidazo[4,5-b]pyridin-3-yl)methyl]-3-chloro-1-benzothiophene-2-carboxylate Chemical compound C1=C2C(Cl)=C(C(=O)OC)SC2=CC(CN2C3=NC=CC=C3N=C2CCCC)=C1 CPIOBMFNASQBPI-UHFFFAOYSA-N 0.000 description 1
- NZCLMHZJMDXBLO-UHFFFAOYSA-N methyl n-[2-[4-[(2-ethyl-7-methylimidazo[4,5-b]pyridin-3-yl)methyl]phenyl]phenyl]sulfonylcarbamate Chemical compound CCC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1S(=O)(=O)NC(=O)OC NZCLMHZJMDXBLO-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 210000005164 penile vein Anatomy 0.000 description 1
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- CAEWJEXPFKNBQL-UHFFFAOYSA-N prop-2-enyl carbonochloridate Chemical compound ClC(=O)OCC=C CAEWJEXPFKNBQL-UHFFFAOYSA-N 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 230000029865 regulation of blood pressure Effects 0.000 description 1
- 208000015670 renal artery disease Diseases 0.000 description 1
- 230000036454 renin-angiotensin system Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 102220240796 rs553605556 Human genes 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- DXMISFVOLRPPNP-UHFFFAOYSA-M sodium;nitrite;hydrate Chemical compound O.[Na+].[O-]N=O DXMISFVOLRPPNP-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical compound C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 description 1
- 229940125670 thienopyridine Drugs 0.000 description 1
- 239000002175 thienopyridine Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 230000025033 vasoconstriction Effects 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/08—Radicals containing only hydrogen and carbon atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Heart & Thoracic Surgery (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Detergent Compositions (AREA)
- Lubricants (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4130659:7 | 1991-09-14 | ||
| DE4130659 | 1991-09-14 | ||
| DE4131325:9 | 1991-09-20 | ||
| DE19914131325 DE4131325A1 (de) | 1991-09-20 | 1991-09-20 | Imidazo-annellierte iso und heterocyclen, verfahren zu deren herstellung, sie enthaltende mittel und ihre verwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05262742A JPH05262742A (ja) | 1993-10-12 |
| JP3459659B2 true JP3459659B2 (ja) | 2003-10-20 |
Family
ID=25907347
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP24346992A Expired - Lifetime JP3459659B2 (ja) | 1991-09-14 | 1992-09-11 | イミダゾ−縮合の同素環および複素環 |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US5444068A (enExample) |
| EP (1) | EP0533058B1 (enExample) |
| JP (1) | JP3459659B2 (enExample) |
| KR (1) | KR930006020A (enExample) |
| CN (1) | CN1070646A (enExample) |
| AT (1) | ATE247644T1 (enExample) |
| AU (1) | AU659485B2 (enExample) |
| BR (1) | BR9203543A (enExample) |
| CA (1) | CA2078058A1 (enExample) |
| CZ (1) | CZ280492A3 (enExample) |
| DE (1) | DE59209986D1 (enExample) |
| DK (1) | DK0533058T3 (enExample) |
| ES (1) | ES2204888T3 (enExample) |
| FI (1) | FI924054A7 (enExample) |
| HU (1) | HUT62892A (enExample) |
| IL (1) | IL103141A0 (enExample) |
| NO (1) | NO300326B1 (enExample) |
| NZ (1) | NZ244303A (enExample) |
| PL (1) | PL171766B1 (enExample) |
| PT (1) | PT533058E (enExample) |
| RU (1) | RU2076105C1 (enExample) |
| TW (1) | TW300219B (enExample) |
Families Citing this family (63)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5223499A (en) * | 1989-05-30 | 1993-06-29 | Merck & Co., Inc. | 6-amino substituted imidazo[4,5-bipyridines as angiotensin II antagonists |
| US5210092A (en) * | 1990-09-25 | 1993-05-11 | Fujisawa Pharmaceutical Co., Ltd. | Angiotensin ii antagonizing heterocyclic derivatives |
| CA2062558A1 (en) * | 1991-03-08 | 1992-09-09 | Prasun K. Chakravarty | Heterocyclic compounds bearing acidic functional groups as angiotensin ii antagonists |
| US5627191A (en) * | 1992-07-10 | 1997-05-06 | The Boots Company Plc | Therapeutic agents |
| TW348175B (en) * | 1993-01-06 | 1998-12-21 | Hoechst Ag | Process for the preparation of biphenyl derivatives |
| CA2125251C (en) * | 1993-06-07 | 2005-04-26 | Yoshiyuki Inada | A pharmaceutical composition for angiotensin ii-mediated diseases |
| US5571813A (en) * | 1993-06-10 | 1996-11-05 | Beiersdorf-Lilly Gmbh | Fused pyrimidine compounds and their use as pharmaceuticals |
| EP0628559B1 (en) * | 1993-06-10 | 2002-04-03 | Beiersdorf-Lilly GmbH | Pyrimidine compounds and their use as pharmaceuticals |
| DE4320432A1 (de) * | 1993-06-21 | 1994-12-22 | Bayer Ag | Substituierte Mono- und Bipyridylmethylderivate |
| FR2708612B1 (fr) * | 1993-08-05 | 1996-03-01 | Roussel Uclaf | Nouveaux dérivés bicycliques de l'imidazole, leur procédé de préparation, les nouveaux intermédiaires obtenus, leur application à titre de médicaments et les compositions pharmaceutiques les renfermant. |
| WO1996004270A1 (en) | 1994-08-04 | 1996-02-15 | Synaptic Pharmaceutical Corporation | Novel benzimidazole derivatives |
| DE69712167T2 (de) * | 1996-12-18 | 2002-11-21 | Showa Denko K.K., Tokio/Tokyo | Speicher |
| US6495583B1 (en) | 1997-03-25 | 2002-12-17 | Synaptic Pharmaceutical Corporation | Benzimidazole derivatives |
| WO1998047892A1 (en) * | 1997-04-24 | 1998-10-29 | Ortho-Mcneil Corporation, Inc. | Substituted imidazoles useful in the treatment of inflammatory diseases |
| TW589309B (en) | 1997-07-03 | 2004-06-01 | Bristol Myers Squibb Pharma Co | Imidazopyrimidines and imidazopyridines for the treatment of neurological disorders |
| TR200002242T2 (tr) * | 1997-11-24 | 2000-11-21 | The Procter &Gamble Company | 5-(2-İmidazolinilamino)-benzimidazol türevleri, bunların hazırlanması ve metabolik kararlılığı gelişmiş alfa-adrenoseptör agonistleri olarak kullanımları. |
| US6365589B1 (en) | 1998-07-02 | 2002-04-02 | Bristol-Myers Squibb Pharma Company | Imidazo-pyridines, -pyridazines, and -triazines as corticotropin releasing factor antagonists |
| US6124463A (en) * | 1998-07-02 | 2000-09-26 | Dupont Pharmaceuticals | Benzimidazoles as corticotropin release factor antagonists |
| EP1097926A4 (en) | 1998-07-15 | 2004-06-30 | Teijin Ltd | THIOBENZIMIDAZOLE DERIVATIVES |
| US20050267148A1 (en) * | 1998-07-15 | 2005-12-01 | Teijin Limited | Benzimidazole derivative |
| EP1117966A1 (en) * | 1998-09-29 | 2001-07-25 | Stanhope Products Company | Self-positioning adsorbent package for air conditioning accumulators |
| US6331539B1 (en) * | 1999-06-10 | 2001-12-18 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
| US6279341B1 (en) * | 1999-07-01 | 2001-08-28 | Multisorb Technologies, Inc. | Self-retaining adsorbent unit |
| GB9919778D0 (en) * | 1999-08-21 | 1999-10-27 | Zeneca Ltd | Chemical compounds |
| CA2365118A1 (en) * | 2000-01-17 | 2001-07-26 | Teijin Limited | Inhibitor against human chymase activity |
| WO2003064414A1 (en) * | 2002-01-29 | 2003-08-07 | Vicore Pharma Ab. | Tricyclic compounds useful as angiotensin ii agonists |
| AU2003263413A1 (en) * | 2002-09-17 | 2004-04-08 | Warner-Lambert Company Llc | Heterocyclic substituted piperazines for the treatment of schizophrenia |
| US20040102360A1 (en) * | 2002-10-30 | 2004-05-27 | Barnett Stanley F. | Combination therapy |
| BRPI0413558A (pt) | 2003-08-12 | 2006-10-17 | 3M Innovative Properties Co | compostos contendo imidazo substituìdo por hidroxilamina |
| MY145983A (en) | 2003-08-27 | 2012-05-31 | 3M Innovative Properties Co | Aryloxy and arylalkyleneoxy substituted imidazoquinolines |
| EP1660026A4 (en) | 2003-09-05 | 2008-07-16 | 3M Innovative Properties Co | 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 |
| WO2005048933A2 (en) | 2003-11-14 | 2005-06-02 | 3M Innovative Properties Company | Oxime substituted imidazo ring compounds |
| CN1906192A (zh) | 2003-11-14 | 2007-01-31 | 3M创新有限公司 | 羟胺取代的咪唑环化合物 |
| AU2004293078B2 (en) | 2003-11-25 | 2012-01-19 | 3M Innovative Properties Company | Substituted imidazo ring systems and methods |
| US8802853B2 (en) | 2003-12-29 | 2014-08-12 | 3M Innovative Properties Company | Arylalkenyl and arylalkynyl substituted imidazoquinolines |
| JP2007517044A (ja) | 2003-12-30 | 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 | イミダゾキノリニル、イミダゾピリジニル、およびイミダゾナフチリジニルスルホンアミド |
| 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 |
| US7897609B2 (en) | 2004-06-18 | 2011-03-01 | 3M Innovative Properties Company | Aryl substituted imidazonaphthyridines |
| US7915281B2 (en) | 2004-06-18 | 2011-03-29 | 3M Innovative Properties Company | Isoxazole, dihydroisoxazole, and oxadiazole substituted imidazo ring compounds and method |
| EP1831226B1 (en) | 2004-12-30 | 2012-08-08 | 3M Innovative Properties Company | Chiral tetracyclic compounds inducing interferon biosynthesis |
| WO2006083440A2 (en) | 2004-12-30 | 2006-08-10 | 3M Innovative Properties Company | Substituted chiral fused [1,2]imidazo[4,5-c] ring compounds |
| WO2006084251A2 (en) | 2005-02-04 | 2006-08-10 | Coley Pharmaceutical Group, Inc. | Aqueous gel formulations containing immune reponse modifiers |
| US7968563B2 (en) | 2005-02-11 | 2011-06-28 | 3M Innovative Properties Company | Oxime and hydroxylamine substituted imidazo[4,5-c] ring compounds and methods |
| AU2006232377A1 (en) | 2005-04-01 | 2006-10-12 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridine-1,4-diamines and analogs thereof |
| WO2006107851A1 (en) | 2005-04-01 | 2006-10-12 | Coley Pharmaceutical Group, Inc. | 1-substituted pyrazolo (3,4-c) ring compounds as modulators of cytokine biosynthesis for the treatment of viral infections and neoplastic diseases |
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| JP2018516973A (ja) | 2015-06-10 | 2018-06-28 | フォーラム・ファーマシューティカルズ・インコーポレイテッドＦｏｒｕｍ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃ． | α７−ニコチン性アセチルコリン受容体のアゴニストとしてのアミノベンゾイソオキサゾール化合物 |
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-
1992
- 1992-03-07 TW TW081101731A patent/TW300219B/zh active
- 1992-09-10 DE DE59209986T patent/DE59209986D1/de not_active Expired - Lifetime
- 1992-09-10 EP EP92115500A patent/EP0533058B1/de not_active Expired - Lifetime
- 1992-09-10 ES ES92115500T patent/ES2204888T3/es not_active Expired - Lifetime
- 1992-09-10 DK DK92115500T patent/DK0533058T3/da active
- 1992-09-10 FI FI924054A patent/FI924054A7/fi not_active Application Discontinuation
- 1992-09-10 PT PT92115500T patent/PT533058E/pt unknown
- 1992-09-10 AT AT92115500T patent/ATE247644T1/de active
- 1992-09-11 NZ NZ244303A patent/NZ244303A/en unknown
- 1992-09-11 NO NO923535A patent/NO300326B1/no unknown
- 1992-09-11 BR BR929203543A patent/BR9203543A/pt not_active Application Discontinuation
- 1992-09-11 CZ CS922804A patent/CZ280492A3/cs unknown
- 1992-09-11 JP JP24346992A patent/JP3459659B2/ja not_active Expired - Lifetime
- 1992-09-11 IL IL103141A patent/IL103141A0/xx unknown
- 1992-09-11 PL PL92295911A patent/PL171766B1/pl unknown
- 1992-09-11 RU SU925053022A patent/RU2076105C1/ru active
- 1992-09-11 CA CA002078058A patent/CA2078058A1/en not_active Abandoned
- 1992-09-11 AU AU23533/92A patent/AU659485B2/en not_active Ceased
- 1992-09-12 CN CN92110562A patent/CN1070646A/zh active Pending
- 1992-09-14 HU HU9202931A patent/HUT62892A/hu unknown
- 1992-09-14 KR KR1019920016634A patent/KR930006020A/ko not_active Ceased
-
1993
- 1993-12-13 US US08/165,655 patent/US5444068A/en not_active Expired - Lifetime
-
1995
- 1995-06-05 US US08/463,299 patent/US5635525A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| AU2353392A (en) | 1993-03-18 |
| NO300326B1 (no) | 1997-05-12 |
| US5444068A (en) | 1995-08-22 |
| ATE247644T1 (de) | 2003-09-15 |
| EP0533058A1 (de) | 1993-03-24 |
| NO923535D0 (no) | 1992-09-11 |
| HU9202931D0 (en) | 1992-11-30 |
| PL171766B1 (pl) | 1997-06-30 |
| RU2076105C1 (ru) | 1997-03-27 |
| NO923535L (no) | 1993-03-15 |
| JPH05262742A (ja) | 1993-10-12 |
| BR9203543A (pt) | 1993-04-13 |
| US5635525A (en) | 1997-06-03 |
| PL295911A1 (en) | 1993-03-22 |
| CA2078058A1 (en) | 1993-03-15 |
| KR930006020A (ko) | 1993-04-20 |
| TW300219B (enExample) | 1997-03-11 |
| CN1070646A (zh) | 1993-04-07 |
| AU659485B2 (en) | 1995-05-18 |
| IL103141A0 (en) | 1993-02-21 |
| FI924054A0 (fi) | 1992-09-10 |
| HUT62892A (en) | 1993-06-28 |
| ES2204888T3 (es) | 2004-05-01 |
| PT533058E (pt) | 2004-01-30 |
| FI924054L (fi) | 1993-03-15 |
| NZ244303A (en) | 1995-12-21 |
| DE59209986D1 (de) | 2003-09-25 |
| CZ280492A3 (en) | 1993-04-14 |
| EP0533058B1 (de) | 2003-08-20 |
| DK0533058T3 (da) | 2003-11-24 |
| FI924054A7 (fi) | 1993-03-15 |
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