LT3671B - Substituted 1-(1h-imidazol-4-il)alkylbenzamides - Google Patents

Substituted 1-(1h-imidazol-4-il)alkylbenzamides Download PDF

Info

Publication number: LT3671B
Authority: LT; Lithuania
Prior art keywords: imidazol; methyl; hydroxy; ethyl; chlorohydrate
Prior art date: 1988-04-28

Application number

LTIP827A

Other languages

English (en)

Lithuanian (lt)

Inventor

Eric Cossement

Jean-Pierre Geerts

Jean Gobert

Philippe Michel

Ernst Wuelfert

Original Assignee

Ucb Sa

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.)

1988-04-28

Filing date

1993-08-03

Publication date

1996-01-25

1993-08-03 Application filed by Ucb Sa filed Critical Ucb Sa

1995-02-27 Publication of LTIP827A publication Critical patent/LTIP827A/xx

1996-01-25 Publication of LT3671B publication Critical patent/LT3671B/lt

Links

239000000203 mixture Substances 0.000 claims description 45
125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims description 41
125000000217 alkyl group Chemical group 0.000 claims description 20
239000002253 acid Substances 0.000 claims description 19
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 11
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 5
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
230000003287 optical effect Effects 0.000 claims description 2
208000012902 Nervous system disease Diseases 0.000 claims 1
208000025966 Neurological disease Diseases 0.000 claims 1
208000023589 ischemic disease Diseases 0.000 claims 1
230000000302 ischemic effect Effects 0.000 claims 1
150000001875 compounds Chemical class 0.000 description 95
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 57
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 57
-1 alkyl radical Chemical class 0.000 description 57
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
239000000243 solution Substances 0.000 description 45
238000012360 testing method Methods 0.000 description 42
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 42
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
238000002844 melting Methods 0.000 description 35
230000008018 melting Effects 0.000 description 35
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 33
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 25
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 25
238000004458 analytical method Methods 0.000 description 24
239000000047 product Substances 0.000 description 23
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
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238000010992 reflux Methods 0.000 description 18
239000002904 solvent Substances 0.000 description 18
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
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KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
238000000034 method Methods 0.000 description 15
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229940126062 Compound A Drugs 0.000 description 14
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 14
238000002360 preparation method Methods 0.000 description 14
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
238000004587 chromatography analysis Methods 0.000 description 12
238000010898 silica gel chromatography Methods 0.000 description 12
239000000725 suspension Substances 0.000 description 12
230000002253 anti-ischaemic effect Effects 0.000 description 11
239000003480 eluent Substances 0.000 description 11
150000001408 amides Chemical class 0.000 description 10
230000002490 cerebral effect Effects 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
239000000706 filtrate Substances 0.000 description 10
239000002244 precipitate Substances 0.000 description 10
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
229910052739 hydrogen Inorganic materials 0.000 description 9
AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
239000011780 sodium chloride Substances 0.000 description 9
235000011121 sodium hydroxide Nutrition 0.000 description 9
238000011282 treatment Methods 0.000 description 9
GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical group ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 8
239000000556 agonist Substances 0.000 description 8
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 8
239000000460 chlorine Substances 0.000 description 8
239000001257 hydrogen Substances 0.000 description 8
108060003345 Adrenergic Receptor Proteins 0.000 description 7
102000017910 Adrenergic receptor Human genes 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
102000005962 receptors Human genes 0.000 description 7
108020003175 receptors Proteins 0.000 description 7
230000011514 reflex Effects 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
241000700199 Cavia porcellus Species 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
241000700159 Rattus Species 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
208000001871 Tachycardia Diseases 0.000 description 6
229960002896 clonidine Drugs 0.000 description 6
230000000694 effects Effects 0.000 description 6
230000007062 hydrolysis Effects 0.000 description 6
238000006460 hydrolysis reaction Methods 0.000 description 6
230000033001 locomotion Effects 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
230000006794 tachycardia Effects 0.000 description 6
238000005481 NMR spectroscopy Methods 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
238000009835 boiling Methods 0.000 description 5
230000001882 diuretic effect Effects 0.000 description 5
150000002431 hydrogen Chemical class 0.000 description 5
208000028867 ischemia Diseases 0.000 description 5
231100000252 nontoxic Toxicity 0.000 description 5
230000003000 nontoxic effect Effects 0.000 description 5
230000000144 pharmacologic effect Effects 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
239000000377 silicon dioxide Substances 0.000 description 5
RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
DPLPVSAVUWCYNF-UHFFFAOYSA-N 2-hydroxy-3-(1h-imidazol-5-ylmethyl)benzonitrile Chemical compound C1=CC=C(C#N)C(O)=C1CC1=CNC=N1 DPLPVSAVUWCYNF-UHFFFAOYSA-N 0.000 description 4
KIWVQMNOMQFIMX-UHFFFAOYSA-N 2-hydroxy-3-[1-(1h-imidazol-5-yl)ethyl]benzonitrile Chemical compound C=1C=CC(C#N)=C(O)C=1C(C)C1=CNC=N1 KIWVQMNOMQFIMX-UHFFFAOYSA-N 0.000 description 4
241000282472 Canis lupus familiaris Species 0.000 description 4
WCQZCKUNZVMBDC-UHFFFAOYSA-N Methyl 2,6-dihydroxybenzoate Chemical compound COC(=O)C1=C(O)C=CC=C1O WCQZCKUNZVMBDC-UHFFFAOYSA-N 0.000 description 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
230000001270 agonistic effect Effects 0.000 description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
230000010102 embolization Effects 0.000 description 4
239000000284 extract Substances 0.000 description 4
210000002837 heart atrium Anatomy 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
APDJQXVNDDVVLL-UHFFFAOYSA-N methyl 2-hydroxy-3-(1h-imidazol-5-ylmethyl)benzoate Chemical compound COC(=O)C1=CC=CC(CC=2N=CNC=2)=C1O APDJQXVNDDVVLL-UHFFFAOYSA-N 0.000 description 4
SWBLOKTUAMDJFS-UHFFFAOYSA-N methyl 3-(2-chloroprop-2-enyl)-2-hydroxybenzoate Chemical compound COC(=O)C1=CC=CC(CC(Cl)=C)=C1O SWBLOKTUAMDJFS-UHFFFAOYSA-N 0.000 description 4
230000007971 neurological deficit Effects 0.000 description 4
239000001301 oxygen Substances 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
230000003518 presynaptic effect Effects 0.000 description 4
229960003712 propranolol Drugs 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
WWYICDVSTJYCOI-UHFFFAOYSA-N 4-(1h-imidazol-5-ylmethyl)-2h-furan-5-one Chemical compound O=C1OCC=C1CC1=CNC=N1 WWYICDVSTJYCOI-UHFFFAOYSA-N 0.000 description 3
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
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PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
CELPHAGZKFMOMR-UHFFFAOYSA-N azanium;dichloromethane;methanol;hydroxide Chemical compound [NH4+].[OH-].OC.ClCCl CELPHAGZKFMOMR-UHFFFAOYSA-N 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
210000004351 coronary vessel Anatomy 0.000 description 3
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PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 3
SJBDRJJRUIXKEQ-UHFFFAOYSA-N ethyl 2-(1h-imidazol-5-ylmethyl)-3-oxo-4-phenylmethoxybutanoate Chemical compound C=1C=CC=CC=1COCC(=O)C(C(=O)OCC)CC1=CNC=N1 SJBDRJJRUIXKEQ-UHFFFAOYSA-N 0.000 description 3
SEOZREAJSKYCRP-UHFFFAOYSA-N ethyl 3-hydroxy-2-(1h-imidazol-5-ylmethyl)-4-phenylmethoxybutanoate Chemical compound C=1C=CC=CC=1COCC(O)C(C(=O)OCC)CC1=CNC=N1 SEOZREAJSKYCRP-UHFFFAOYSA-N 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
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238000002474 experimental method Methods 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
231100000636 lethal dose Toxicity 0.000 description 3
RDJJAOULNAUWLL-UHFFFAOYSA-N methyl 2-(2-chloroprop-2-enoxy)benzoate Chemical compound COC(=O)C1=CC=CC=C1OCC(Cl)=C RDJJAOULNAUWLL-UHFFFAOYSA-N 0.000 description 3
OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
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239000008194 pharmaceutical composition Substances 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
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NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
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JPFXYDIRXPIKKP-UHFFFAOYSA-N 2-hydroxy-3-(1h-imidazol-5-ylmethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC(CC=2N=CNC=2)=C1O JPFXYDIRXPIKKP-UHFFFAOYSA-N 0.000 description 2
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
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GKACPFZUUPNDKR-UHFFFAOYSA-N [2-hydroxy-5-(1h-imidazol-5-ylmethyl)phenyl]-pyrrolidin-1-ylmethanone Chemical compound C1=C(C(=O)N2CCCC2)C(O)=CC=C1CC1=CNC=N1 GKACPFZUUPNDKR-UHFFFAOYSA-N 0.000 description 2
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HYTACLVSJIFYBY-UHFFFAOYSA-N azane;dichloromethane;methanol Chemical compound N.OC.ClCCl HYTACLVSJIFYBY-UHFFFAOYSA-N 0.000 description 2
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230000000747 cardiac effect Effects 0.000 description 2
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WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 2
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125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
238000013421 nuclear magnetic resonance imaging Methods 0.000 description 1
ZWLPBLYKEWSWPD-UHFFFAOYSA-M o-toluate Chemical compound CC1=CC=CC=C1C([O-])=O ZWLPBLYKEWSWPD-UHFFFAOYSA-M 0.000 description 1
239000003605 opacifier Substances 0.000 description 1
229940127240 opiate Drugs 0.000 description 1
229960001027 opium Drugs 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical class C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
210000005037 parasympathetic nerve Anatomy 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
230000008092 positive effect Effects 0.000 description 1
PRWVAPJXQCMOFT-UHFFFAOYSA-M potassium;azane;hydroxide Chemical compound N.[OH-].[K+] PRWVAPJXQCMOFT-UHFFFAOYSA-M 0.000 description 1
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
208000020016 psychiatric disease Diseases 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
239000000018 receptor agonist Substances 0.000 description 1
229940044601 receptor agonist Drugs 0.000 description 1
239000012925 reference material Substances 0.000 description 1
230000029865 regulation of blood pressure Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000011146 sterile filtration Methods 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
230000002936 tranquilizing effect Effects 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
230000002792 vascular Effects 0.000 description 1
239000008215 water for injection Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- 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
- A61P9/08—Vasodilators for multiple indications
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Biomedical Technology (AREA)
Epidemiology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Urology & Nephrology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Vascular Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Adhesives Or Adhesive Processes (AREA)
Lubricants (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pyrrole Compounds (AREA)

LTIP827A 1988-04-28 1993-08-03 Substituted 1-(1h-imidazol-4-il)alkylbenzamides LT3671B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB888810067A GB8810067D0 (en)	1988-04-28	1988-04-28	Substituted 1-(1h-imidazol-4-yl)alkyl-benzamides

Publications (2)

Publication Number	Publication Date
LTIP827A LTIP827A (en)	1995-02-27
LT3671B true LT3671B (en)	1996-01-25

Family

ID=10636026

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LTIP827A LT3671B (en)	1988-04-28	1993-08-03	Substituted 1-(1h-imidazol-4-il)alkylbenzamides

Country Status (30)

Country	Link
US (1)	US4923865A (hu)
EP (1)	EP0341231B1 (hu)
JP (1)	JP2840288B2 (hu)
KR (1)	KR970011275B1 (hu)
AT (1)	ATE82571T1 (hu)
AU (1)	AU610796B2 (hu)
BR (2)	BR1100052A (hu)
CA (1)	CA1310966C (hu)
CY (1)	CY1758A (hu)
DE (1)	DE68903531T2 (hu)
DK (1)	DK205589A (hu)
ES (1)	ES2052969T3 (hu)
FI (1)	FI101791B1 (hu)
GB (1)	GB8810067D0 (hu)
GR (1)	GR3006836T3 (hu)
HK (1)	HK9494A (hu)
HU (1)	HU203877B (hu)
IE (1)	IE63698B1 (hu)
IL (1)	IL90087A0 (hu)
LT (1)	LT3671B (hu)
LV (1)	LV10437B (hu)
MY (1)	MY104084A (hu)
NO (1)	NO173331C (hu)
NZ (1)	NZ228897A (hu)
PH (1)	PH25461A (hu)
PL (2)	PL156250B1 (hu)
PT (1)	PT90368B (hu)
RU (3)	RU1830063C (hu)
UA (1)	UA12835A1 (hu)
ZA (1)	ZA893140B (hu)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9310965D0 (en) *	1993-05-27	1993-07-14	Ucb Sa	2-hydroxy-3-(1h-imidazol-4-yl)alkyl)benzenecarboximidamides
HUT74386A (en) *	1993-11-15	1996-12-30	Schering Corp	Phenyl-alkyl imidazoles as h3-receptor antagonists and pharmaceutical compositions containing them
JP3294961B2 (ja) *	1993-12-10	2002-06-24	杏林製薬株式会社	新規イミダゾール誘導体及びその製造法
GB9521680D0 (en) *	1995-10-23	1996-01-03	Orion Yhtymo Oy	New use of imidazole derivatives
DE10161818A1 (de) *	2001-12-14	2003-06-26	Gruenenthal Gmbh	Substituierte 1,5-Diaminopentan-3-ol-Verbindungen
BRPI0516132A (pt) *	2004-10-07	2007-12-04	Vitae Pharmaceuticals Inc	compostos, composição destes, método de antagonização de uma ou mais proteases aspárticas e método para tratar ou melhorar um distúrbio mediado por protease aspártica
TWI411607B (zh) *	2005-11-14	2013-10-11	Vitae Pharmaceuticals Inc	天門冬胺酸蛋白酶抑制劑
CL2007002689A1 (es)	2006-09-18	2008-04-18	Vitae Pharmaceuticals Inc	Compuestos derivados de piperidin-1-carboxamida, inhibidores de la renina; compuestos intermediarios; composicion farmaceutica; y uso en el tratamiento de enfermedades tales como hipertension, insuficiencia cardiaca, fibrosis cardiaca, entre otras.
EP2167609A1 (en) *	2007-06-20	2010-03-31	Vitae Pharmaceuticals, Inc.	Renin inhibitors
US20100160424A1 (en) *	2007-06-20	2010-06-24	Baldwin John J	Renin inhibitors
US20090226549A1 (en)	2008-03-06	2009-09-10	Kenneth John Hughes	Herbal extracts and flavor systems for oral products and methods of making the same
US20110160300A1 (en) *	2008-06-20	2011-06-30	Marlys Hammond	Renin Inhibitors and Methods of Use Thereof
CN102088850A (zh) *	2008-06-26	2011-06-08	生命医药公司	甲基2-((r)-(3-氯苯基)((r)-1-((s)-2-(甲氨基)-3((r)-四氢-2h-吡喃-3-基)丙基氨甲酰基)哌啶-3-基)甲氧基)氨基甲酸乙酯的盐
AR077692A1 (es) *	2009-08-06	2011-09-14	Vitae Pharmaceuticals Inc	Sales de 2-((r)-(3-clorofenil) ((r)-1-((s) -2-(metilamino)-3-((r)-tetrahidro-2h-piran-3-il) propilcarbamoil) piperidin -3-il) metoxi) etilcarbamato de metilo
US9249087B2 (en) *	2011-02-01	2016-02-02	The Board Of Trustees Of The University Of Illinois	HDAC inhibitors and therapeutic methods using the same

Citations (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0024839A1 (en)	1979-08-20	1981-03-11	Minnesota Mining And Manufacturing Company	Photopolymerizable mixtures and methods of making viscoelastic and pressure sensitive adhesive products therewith
EP0058047A1 (en)	1981-02-05	1982-08-18	Farmos-Yhtyma Oy	Substituted imidazole derivatives and their preparation and use
EP0072615A1 (en)	1981-07-10	1983-02-23	Farmos Group Ltd.	Substituted imidazole derivatives and their preparation and use
EP0269559A2 (de)	1986-10-21	1988-06-01	Visita Mtc Ltd.	Hubeinrichtung

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU518569B2 (en) *	1979-08-07	1981-10-08	Farmos-Yhtyma Oy	4-benzyl- and 4-benzoyl imidazole derivatives
GB8626287D0 (en) *	1986-11-04	1986-12-03	Ucb Sa	Substituted 1h-imidazoles
GB8714013D0 (en) *	1987-06-16	1987-07-22	Ici Plc	(substituted-aralkyl)heterocyclic compounds

1988
- 1988-04-28 GB GB888810067A patent/GB8810067D0/en active Pending
1989
- 1989-03-31 CA CA000595384A patent/CA1310966C/en not_active Expired - Lifetime
- 1989-04-06 US US07/334,854 patent/US4923865A/en not_active Expired - Fee Related
- 1989-04-20 DE DE8989870054T patent/DE68903531T2/de not_active Expired - Fee Related
- 1989-04-20 EP EP89870054A patent/EP0341231B1/fr not_active Expired - Lifetime
- 1989-04-20 AT AT89870054T patent/ATE82571T1/de active
- 1989-04-20 ES ES89870054T patent/ES2052969T3/es not_active Expired - Lifetime
- 1989-04-25 PL PL1989279104A patent/PL156250B1/pl unknown
- 1989-04-25 IL IL90087A patent/IL90087A0/xx not_active IP Right Cessation
- 1989-04-25 PL PL1989283865A patent/PL161362B1/pl unknown
- 1989-04-25 MY MYPI89000528A patent/MY104084A/en unknown
- 1989-04-25 PH PH38563A patent/PH25461A/en unknown
- 1989-04-26 NZ NZ228897A patent/NZ228897A/xx unknown
- 1989-04-26 PT PT90368A patent/PT90368B/pt not_active IP Right Cessation
- 1989-04-26 FI FI891975A patent/FI101791B1/fi not_active IP Right Cessation
- 1989-04-26 IE IE136089A patent/IE63698B1/en not_active IP Right Cessation
- 1989-04-27 RU SU894613927A patent/RU1830063C/ru active
- 1989-04-27 AU AU33730/89A patent/AU610796B2/en not_active Ceased
- 1989-04-27 NO NO891760A patent/NO173331C/no not_active IP Right Cessation
- 1989-04-27 DK DK205589A patent/DK205589A/da unknown
- 1989-04-27 JP JP1109030A patent/JP2840288B2/ja not_active Expired - Lifetime
- 1989-04-27 ZA ZA893140A patent/ZA893140B/xx unknown
- 1989-04-28 HU HU892041A patent/HU203877B/hu not_active IP Right Cessation
- 1989-04-28 KR KR1019890005825A patent/KR970011275B1/ko not_active Expired - Fee Related
- 1989-10-04 RU SU894742030A patent/RU1814647C/ru active
- 1989-10-04 UA UA4613927A patent/UA12835A1/uk unknown
1990
- 1990-04-05 RU SU904743506A patent/RU1836353C/ru active
1993
- 1993-01-21 GR GR930400087T patent/GR3006836T3/el unknown
- 1993-06-11 LV LVP-93-548A patent/LV10437B/lv unknown
- 1993-08-03 LT LTIP827A patent/LT3671B/lt not_active IP Right Cessation
1994
- 1994-02-02 HK HK94/94A patent/HK9494A/xx not_active IP Right Cessation
- 1994-07-15 CY CY175894A patent/CY1758A/xx unknown
1996
- 1996-09-23 BR BR1100052-0A patent/BR1100052A/pt active IP Right Grant
- 1996-10-17 BR BR1100064-3A patent/BR1100064A/pt active IP Right Grant

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0024839A1 (en)	1979-08-20	1981-03-11	Minnesota Mining And Manufacturing Company	Photopolymerizable mixtures and methods of making viscoelastic and pressure sensitive adhesive products therewith
EP0058047A1 (en)	1981-02-05	1982-08-18	Farmos-Yhtyma Oy	Substituted imidazole derivatives and their preparation and use
EP0072615A1 (en)	1981-07-10	1983-02-23	Farmos Group Ltd.	Substituted imidazole derivatives and their preparation and use
EP0269559A2 (de)	1986-10-21	1988-06-01	Visita Mtc Ltd.	Hubeinrichtung

Non-Patent Citations (12)

* Cited by examiner, † Cited by third party
Title
A. DENARO ET AL.: "Headache and noradrenergic involvement: the effects of Î±2-stimulants and Î±2-antagonists", ACTA PSYCHIATRICA SCANDINAVICA, 1985, pages 20 - 25
BRALET AM , ET AL.: "Brain edema and blood-brain barrier permeability following quantitative cere-bral microembolism", STROKE, 1979, pages 34 - 38
EPSTEIN SE ET AL.: "Protection of ischemic myocardium by nitroglycerin: Experimental and clinical results", CIRCULATION, 1976, pages 191 - 197
G.M. DREW: "Pharmacological characterization of the presynaptic Î±-adrenoceptors regulating cholinergic activity in the guinea-pig ileum", BR J PHARMACOL., 1978, pages 293 - 300
I. C. MEDGETT, M. W. MCCULLOCH, M. J. RAND: "Partial agonist action of clonidine on prejunctional and postjunctional Î±-adrenoceptors", NAUNYN-SCHMIEDEBERGS ARCHIVES OF PHARMACOLOGY, 1978, pages 215 - 221
JOHN F. MARSHALL ET AL.: "Sensory Neglect Produced by Lateral Hypothalamic Damage", SCIENCE, 1971, pages 523 - 525
M LA PONCIN-LAFITTE ET AL.: "Demonstration of a vertebro-basilar support in carotid complications", JOURNAL DE PHARMACOLOGIE, 1983, pages 99 - 102
M. ANDRÉJAK, Y. POMMIER, P. MOUILLÉ, H. SCH: "Effects of some Î±-adrenoceptor agonists and antagonists on the guinea-pig ileum", NAUNYN-SCHMIEDEBERGS ARCHIVES OF PHARMACOLOGY, 1980, pages 83 - 87
M. J. RAND ET AL.: "Central Action Drugs in Blood Pressure Regulation", pages: 94 - 132
MAROKO PR ET AL: "fects of metabolic and pharmacologic nterventions on myocardial infarct size following coronary occlusion", CIRCULATION, 1976, pages 162 - 168
MOTULSKY HJ, INSEL PA: "Adrenergic receptors in man: direct identification, physiologic regulation, and clinical alterations", N ENGL J MED., 1982, pages 18 - 29
YOSHIHIRO KIYOTA ET AL.: "Cerebral embolization leads to memory impairment of several learning tasks in rats", PHARMACOLOGY BIOCHEMISTRY AND BEHAVIOR, 1986, pages 687 - 692

Also Published As

Publication number	Publication date
IE63698B1 (en)	1995-05-31
FI891975A7 (fi)	1989-10-29
CY1758A (en)	1994-07-15
RU1814647C (ru)	1993-05-07
HUT51257A (en)	1990-04-28
HK9494A (en)	1994-02-09
FI101791B (fi)	1998-08-31
EP0341231B1 (fr)	1992-11-19
DE68903531D1 (de)	1992-12-24
NO891760D0 (no)	1989-04-27
AU610796B2 (en)	1991-05-23
EP0341231A1 (fr)	1989-11-08
BR1100064A (pt)	1999-12-07
LTIP827A (en)	1995-02-27
NO173331B (no)	1993-08-23
MY104084A (en)	1993-11-30
HU203877B (en)	1991-10-28
GR3006836T3 (hu)	1993-06-30
PH25461A (en)	1991-07-01
FI891975A0 (fi)	1989-04-26
PT90368B (pt)	1994-08-31
JP2840288B2 (ja)	1998-12-24
ES2052969T3 (es)	1994-07-16
FI101791B1 (fi)	1998-08-31
IL90087A0 (en)	1989-12-15
BR1100052A (pt)	1999-12-07
PT90368A (pt)	1989-11-10
IE891360L (en)	1989-10-28
DK205589A (da)	1989-10-29
ZA893140B (en)	1990-01-31
KR970011275B1 (ko)	1997-07-09
PL156250B1 (pl)	1992-02-28
UA12835A1 (uk)	1997-02-28
RU1836353C (ru)	1993-08-23
NO173331C (no)	1993-12-08
NZ228897A (en)	1990-08-28
AU3373089A (en)	1989-11-02
DE68903531T2 (de)	1993-04-29
ATE82571T1 (de)	1992-12-15
JPH01313467A (ja)	1989-12-18
CA1310966C (en)	1992-12-01
US4923865A (en)	1990-05-08
RU1830063C (ru)	1993-07-23
KR890016017A (ko)	1989-11-28
LV10437B (en)	1996-04-20
NO891760L (no)	1989-10-30
PL161362B1 (pl)	1993-06-30
DK205589D0 (da)	1989-04-27
GB8810067D0 (en)	1988-06-02
LV10437A (lv)	1995-02-20

Publication	Publication Date	Title
RU2005721C1 (ru)	1994-01-15	Способ получения 3-хинуклидинилпропаноатов
AU769081B2 (en)	2004-01-15	NPY antagonists: spiroisoquinolinone derivatives
US6054590A (en)	2000-04-25	Imidazolone anorectic agents: II. phenyl derivatives
LT3671B (en)	1996-01-25	Substituted 1-(1h-imidazol-4-il)alkylbenzamides
DE69215965T2 (de)	1997-04-10	Pyrazolopyridinverbindungen und Verfahren zu ihrer Herstellung
DE68904586T2 (de)	1993-08-19	Histamin-derivat, verfahren zu dessen herstellung und therapeutischen anwendung.
KR20010099674A (ko)	2001-11-09	타키키닌 수용체 길항물질로서의 나프탈렌카르복스아미드
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JP2656594B2 (ja)	1997-09-24	ジアミン化合物、その製法及び該化合物を含有する高血圧症及び炎症を治療するための医薬
JPWO1999031045A1 (ja)	2002-09-17	フェニルアミノアルキルカルボン酸誘導体およびそれを含有する医薬組成物
JP3068458B2 (ja)	2000-07-24	クロモン誘導体
JP3093419B2 (ja)	2000-10-03	１，４‐ベンゾチアゼピン誘導体
US4863953A (en)	1989-09-05	[3R]-3-amino-1-hydroxy pyrrolidin-2-one and its use as a neuroprotective agent
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