SK42499A3 - 1-phenyl-benzimidazole compounds and their use as gabaa receptor modulators - Google Patents

1-phenyl-benzimidazole compounds and their use as gabaa receptor modulators Download PDF

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Publication number: SK42499A3
Authority: SK; Slovakia
Prior art keywords: phenyl; benzimidazole; compound; alkyl; group
Prior art date: 1996-10-21

Application number

SK424-99A

Other languages

English (en)

Slovak (sk)

Inventor

Lene Teuber

Frank Watjen

Original Assignee

Neurosearch As

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.)

1996-10-21

Filing date

1997-10-21

Publication date

2000-05-16

1997-10-21 Application filed by Neurosearch As filed Critical Neurosearch As

2000-05-16 Publication of SK42499A3 publication Critical patent/SK42499A3/sk

Links

102000027484 GABAA receptors Human genes 0.000 title claims abstract description 5
108091008681 GABAA receptors Proteins 0.000 title claims abstract description 5
XNCMQRWVMWLODV-UHFFFAOYSA-N 1-phenylbenzimidazole Chemical class C1=NC2=CC=CC=C2N1C1=CC=CC=C1 XNCMQRWVMWLODV-UHFFFAOYSA-N 0.000 title 1
-1 cyano, amino Chemical group 0.000 claims abstract description 270
150000001875 compounds Chemical class 0.000 claims abstract description 204
125000000217 alkyl group Chemical group 0.000 claims abstract description 127
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 34
125000003545 alkoxy group Chemical group 0.000 claims abstract description 21
125000001424 substituent group Chemical group 0.000 claims abstract description 21
229910052736 halogen Inorganic materials 0.000 claims abstract description 18
150000002367 halogens Chemical class 0.000 claims abstract description 18
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 17
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 17
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 13
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 10
208000019901 Anxiety disease Diseases 0.000 claims abstract description 5
208000026139 Memory disease Diseases 0.000 claims abstract description 5
230000036506 anxiety Effects 0.000 claims abstract description 5
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 5
125000002911 monocyclic heterocycle group Chemical group 0.000 claims abstract description 5
208000019116 sleep disease Diseases 0.000 claims abstract description 5
239000001257 hydrogen Substances 0.000 claims description 55
229910052739 hydrogen Inorganic materials 0.000 claims description 55
229910052757 nitrogen Inorganic materials 0.000 claims description 53
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 31
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 30
238000002360 preparation method Methods 0.000 claims description 29
238000000034 method Methods 0.000 claims description 27
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 25
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 20
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 20
102000005962 receptors Human genes 0.000 claims description 19
108020003175 receptors Proteins 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 19
125000003342 alkenyl group Chemical group 0.000 claims description 18
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 17
150000002431 hydrogen Chemical class 0.000 claims description 17
201000010099 disease Diseases 0.000 claims description 16
208000035475 disorder Diseases 0.000 claims description 14
125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
125000000623 heterocyclic group Chemical group 0.000 claims description 13
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 13
STBJCSYAZSPDHY-UHFFFAOYSA-N 1-[1-[3-(1-methyl-3,6-dihydro-2h-pyridin-5-yl)phenyl]benzimidazol-5-yl]ethanone Chemical compound C1N(C)CCC=C1C1=CC=CC(N2C3=CC=C(C=C3N=C2)C(C)=O)=C1 STBJCSYAZSPDHY-UHFFFAOYSA-N 0.000 claims description 12
VGNCBRNRHXEODV-XXVHXNRLSA-N (6r,7r)-1-[(4s,5r)-4-acetyloxy-5-methyl-3-methylidene-6-phenylhexyl]-6-dodecoxy-4,7-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid Chemical compound C([C@@H](C)[C@H](OC(C)=O)C(=C)CCC12[C@H](O)[C@H](C(O2)(C(O)=O)C(O)(C(O1)C(O)=O)C(O)=O)OCCCCCCCCCCCC)C1=CC=CC=C1 VGNCBRNRHXEODV-XXVHXNRLSA-N 0.000 claims description 11
125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 11
150000002923 oximes Chemical class 0.000 claims description 11
SXUWNRDETUAGAT-UHFFFAOYSA-N 1-[1-[3-(1-methylpiperidin-3-yl)phenyl]benzimidazol-5-yl]ethanone Chemical compound C1N(C)CCCC1C1=CC=CC(N2C3=CC=C(C=C3N=C2)C(C)=O)=C1 SXUWNRDETUAGAT-UHFFFAOYSA-N 0.000 claims description 10
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 10
MNIPVWXWSPXERA-IDNZQHFXSA-N (6r,7r)-1-[(4s,5r)-4-acetyloxy-5-methyl-3-methylidene-6-phenylhexyl]-4,7-dihydroxy-6-(11-phenoxyundecanoyloxy)-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid Chemical compound C([C@@H](C)[C@H](OC(C)=O)C(=C)CCC12[C@@H]([C@@H](OC(=O)CCCCCCCCCCOC=3C=CC=CC=3)C(O1)(C(O)=O)C(O)(C(O2)C(O)=O)C(O)=O)O)C1=CC=CC=C1 MNIPVWXWSPXERA-IDNZQHFXSA-N 0.000 claims description 9
229940126650 Compound 3f Drugs 0.000 claims description 9
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 9
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 9
125000004430 oxygen atom Chemical group O* 0.000 claims description 9
239000008194 pharmaceutical composition Substances 0.000 claims description 9
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 description 9
KAFZOLYKKCWUBI-HPMAGDRPSA-N (2s)-2-[[(2s)-2-[[(2s)-1-[(2s)-3-amino-2-[[(2s)-2-[[(2s)-2-(3-cyclohexylpropanoylamino)-4-methylpentanoyl]amino]-5-methylhexanoyl]amino]propanoyl]pyrrolidine-2-carbonyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]butanediamide Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CCC(C)C)C(=O)N[C@@H](CN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CC(N)=O)C(N)=O)C(=O)CCC1CCCCC1 KAFZOLYKKCWUBI-HPMAGDRPSA-N 0.000 claims description 7
VIMMECPCYZXUCI-MIMFYIINSA-N (4s,6r)-6-[(1e)-4,4-bis(4-fluorophenyl)-3-(1-methyltetrazol-5-yl)buta-1,3-dienyl]-4-hydroxyoxan-2-one Chemical compound CN1N=NN=C1C(\C=C\[C@@H]1OC(=O)C[C@@H](O)C1)=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 VIMMECPCYZXUCI-MIMFYIINSA-N 0.000 claims description 7
210000003169 central nervous system Anatomy 0.000 claims description 7
DWCQZINMMYYGKC-UHFFFAOYSA-N methyl 2-[1-[3-(4-methylpiperazin-1-yl)phenyl]benzimidazol-5-yl]acetate Chemical compound C1=NC2=CC(CC(=O)OC)=CC=C2N1C(C=1)=CC=CC=1N1CCN(C)CC1 DWCQZINMMYYGKC-UHFFFAOYSA-N 0.000 claims description 7
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 7
MQZIGVAMPTZJTK-UHFFFAOYSA-N 1-[1-(3-piperidin-1-ylphenyl)benzimidazol-5-yl]-n-propan-2-yloxymethanimine Chemical compound C1=NC2=CC(C=NOC(C)C)=CC=C2N1C(C=1)=CC=CC=1N1CCCCC1 MQZIGVAMPTZJTK-UHFFFAOYSA-N 0.000 claims description 6
RUMROGLMWQZLFN-UHFFFAOYSA-N 1-[1-[3-[4-(n-hydroxy-c-methylcarbonimidoyl)piperazin-1-yl]phenyl]benzimidazol-5-yl]ethanone Chemical compound C1=NC2=CC(C(=O)C)=CC=C2N1C(C=1)=CC=CC=1N1CCN(C(C)=NO)CC1 RUMROGLMWQZLFN-UHFFFAOYSA-N 0.000 claims description 6
102000005915 GABA Receptors Human genes 0.000 claims description 6
108010005551 GABA Receptors Proteins 0.000 claims description 6
125000000304 alkynyl group Chemical group 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
OSVHLUXLWQLPIY-KBAYOESNSA-N butyl 2-[(6aR,9R,10aR)-1-hydroxy-9-(hydroxymethyl)-6,6-dimethyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-3-yl]-2-methylpropanoate Chemical compound C(CCC)OC(C(C)(C)C1=CC(=C2[C@H]3[C@H](C(OC2=C1)(C)C)CC[C@H](C3)CO)O)=O OSVHLUXLWQLPIY-KBAYOESNSA-N 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 6
QMGHHBHPDDAGGO-IIWOMYBWSA-N (2S,4R)-1-[(2S)-2-[[2-[3-[4-[3-[4-[[5-bromo-4-[3-[cyclobutanecarbonyl(methyl)amino]propylamino]pyrimidin-2-yl]amino]phenoxy]propoxy]butoxy]propoxy]acetyl]amino]-3,3-dimethylbutanoyl]-4-hydroxy-N-[[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl]pyrrolidine-2-carboxamide Chemical compound CN(CCCNC1=NC(NC2=CC=C(OCCCOCCCCOCCCOCC(=O)N[C@H](C(=O)N3C[C@H](O)C[C@H]3C(=O)NCC3=CC=C(C=C3)C3=C(C)N=CS3)C(C)(C)C)C=C2)=NC=C1Br)C(=O)C1CCC1 QMGHHBHPDDAGGO-IIWOMYBWSA-N 0.000 claims description 5
PNHBRYIAJCYNDA-VQCQRNETSA-N (4r)-6-[2-[2-ethyl-4-(4-fluorophenyl)-6-phenylpyridin-3-yl]ethyl]-4-hydroxyoxan-2-one Chemical compound C([C@H](O)C1)C(=O)OC1CCC=1C(CC)=NC(C=2C=CC=CC=2)=CC=1C1=CC=C(F)C=C1 PNHBRYIAJCYNDA-VQCQRNETSA-N 0.000 claims description 5
QOLHWXNSCZGWHK-BWBORTOCSA-N (6r,7r)-1-[(4s,5r)-4-acetyloxy-5-methyl-3-methylidene-6-phenylhexyl]-4,7-dihydroxy-6-(11-phenoxyundecylcarbamoyloxy)-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid Chemical compound C([C@@H](C)[C@H](OC(C)=O)C(=C)CCC12[C@@H]([C@@H](OC(=O)NCCCCCCCCCCCOC=3C=CC=CC=3)C(O1)(C(O)=O)C(O)(C(O2)C(O)=O)C(O)=O)O)C1=CC=CC=C1 QOLHWXNSCZGWHK-BWBORTOCSA-N 0.000 claims description 5
VFWBKGCNZWEGDO-UHFFFAOYSA-N 1-(3-morpholin-4-ylphenyl)benzimidazole-5-carbonitrile Chemical compound C1=NC2=CC(C#N)=CC=C2N1C(C=1)=CC=CC=1N1CCOCC1 VFWBKGCNZWEGDO-UHFFFAOYSA-N 0.000 claims description 5
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
TUUXBHONHNOINV-UHFFFAOYSA-N 5-(furan-3-yl)-1-[3-(4-methylpiperazin-1-yl)phenyl]benzimidazole Chemical compound C1CN(C)CCN1C1=CC=CC(N2C3=CC=C(C=C3N=C2)C2=COC=C2)=C1 TUUXBHONHNOINV-UHFFFAOYSA-N 0.000 claims description 5
229940126559 Compound 4e Drugs 0.000 claims description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
229940126540 compound 41 Drugs 0.000 claims description 5
229940125872 compound 4d Drugs 0.000 claims description 5
NFSOTVCRKXRRSI-UHFFFAOYSA-N methyl 3-[5-(1,2-oxazol-5-yl)benzimidazol-1-yl]benzoate Chemical compound COC(=O)C1=CC=CC(N2C3=CC=C(C=C3N=C2)C=2ON=CC=2)=C1 NFSOTVCRKXRRSI-UHFFFAOYSA-N 0.000 claims description 5
125000004193 piperazinyl group Chemical group 0.000 claims description 5
HQTJVOIEPSVHBY-UHFFFAOYSA-N (1-methylpiperidin-4-yl) 3-(5-acetylbenzimidazol-1-yl)-n-propan-2-yloxybenzenecarboximidate Chemical compound C=1C=CC(N2C3=CC=C(C=C3N=C2)C(C)=O)=CC=1C(=NOC(C)C)OC1CCN(C)CC1 HQTJVOIEPSVHBY-UHFFFAOYSA-N 0.000 claims description 4
FANCTJAFZSYTIS-IQUVVAJASA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-4-(phenylsulfonimidoyl)butan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C\1C([C@@H](O)C[C@H](O)C/1)=C)C)CS(=N)(=O)C1=CC=CC=C1 FANCTJAFZSYTIS-IQUVVAJASA-N 0.000 claims description 4
PNMAYDWHUWVZRC-UHFFFAOYSA-N 1-[3-(4-methylpiperazin-1-yl)phenyl]-5-phenylbenzimidazole Chemical compound C1CN(C)CCN1C1=CC=CC(N2C3=CC=C(C=C3N=C2)C=2C=CC=CC=2)=C1 PNMAYDWHUWVZRC-UHFFFAOYSA-N 0.000 claims description 4
KGPGFQWBCSZGEL-ZDUSSCGKSA-N GSK690693 Chemical compound C=12N(CC)C(C=3C(=NON=3)N)=NC2=C(C#CC(C)(C)O)N=CC=1OC[C@H]1CCCNC1 KGPGFQWBCSZGEL-ZDUSSCGKSA-N 0.000 claims description 4
241001465754 Metazoa Species 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
229940126214 compound 3 Drugs 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
206010015037 epilepsy Diseases 0.000 claims description 4
QXBRJVSCPIVGEJ-UHFFFAOYSA-N ethyl 3-[5-(furan-3-yl)benzimidazol-1-yl]benzoate Chemical compound CCOC(=O)C1=CC=CC(N2C3=CC=C(C=C3N=C2)C2=COC=C2)=C1 QXBRJVSCPIVGEJ-UHFFFAOYSA-N 0.000 claims description 4
MMMYJMKLEPWDOI-UHFFFAOYSA-N methyl 1-(3-morpholin-4-ylphenyl)benzimidazole-5-carboxylate Chemical compound C1=NC2=CC(C(=O)OC)=CC=C2N1C(C=1)=CC=CC=1N1CCOCC1 MMMYJMKLEPWDOI-UHFFFAOYSA-N 0.000 claims description 4
NJLMWSYRDKRIOW-UHFFFAOYSA-N methyl 3-[1-[3-(4-methylpiperazin-1-yl)phenyl]benzimidazol-5-yl]prop-2-enoate Chemical compound C1=NC2=CC(C=CC(=O)OC)=CC=C2N1C(C=1)=CC=CC=1N1CCN(C)CC1 NJLMWSYRDKRIOW-UHFFFAOYSA-N 0.000 claims description 4
RQEVZDDCLDBNCX-UHFFFAOYSA-N n-ethoxy-1-[1-[3-(1-methylpiperidin-3-yl)phenyl]benzimidazol-5-yl]ethanimine Chemical compound C1=NC2=CC(C(C)=NOCC)=CC=C2N1C(C=1)=CC=CC=1C1CCCN(C)C1 RQEVZDDCLDBNCX-UHFFFAOYSA-N 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
RWWYLEGWBNMMLJ-YSOARWBDSA-N remdesivir Chemical compound NC1=NC=NN2C1=CC=C2[C@]1([C@@H]([C@@H]([C@H](O1)CO[P@](=O)(OC1=CC=CC=C1)N[C@H](C(=O)OCC(CC)CC)C)O)O)C#N RWWYLEGWBNMMLJ-YSOARWBDSA-N 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
NPSJEAUSMFIFIK-UHFFFAOYSA-N (1-methylpiperidin-3-yl) 3-(5-phenylbenzimidazol-1-yl)benzoate Chemical compound C1N(C)CCCC1OC(=O)C1=CC=CC(N2C3=CC=C(C=C3N=C2)C=2C=CC=CC=2)=C1 NPSJEAUSMFIFIK-UHFFFAOYSA-N 0.000 claims description 3
YEHUXQUSKQNYNQ-UHFFFAOYSA-N (1-methylpiperidin-4-yl) 3-(5-phenylbenzimidazol-1-yl)benzoate Chemical compound C1CN(C)CCC1OC(=O)C1=CC=CC(N2C3=CC=C(C=C3N=C2)C=2C=CC=CC=2)=C1 YEHUXQUSKQNYNQ-UHFFFAOYSA-N 0.000 claims description 3
SHAHPWSYJFYMRX-GDLCADMTSA-N (2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C[C@@H]1[C@@H](O)CCC1 SHAHPWSYJFYMRX-GDLCADMTSA-N 0.000 claims description 3
WHQUHTXULUACFD-KRWDZBQOSA-N (3s)-4-[[2-(4-fluoro-3-methylphenyl)-4-methyl-6-propan-2-ylphenyl]methoxy-hydroxyphosphoryl]-3-hydroxybutanoic acid Chemical compound CC(C)C1=CC(C)=CC(C=2C=C(C)C(F)=CC=2)=C1COP(O)(=O)C[C@@H](O)CC(O)=O WHQUHTXULUACFD-KRWDZBQOSA-N 0.000 claims description 3
QVBVQHTXLPNXEY-ZMFCMNQTSA-N (4r)-6-[2-[4-(4-fluorophenyl)-6-phenyl-2-propan-2-ylpyridin-3-yl]ethyl]-4-hydroxyoxan-2-one Chemical compound C([C@H](O)C1)C(=O)OC1CCC=1C(C(C)C)=NC(C=2C=CC=CC=2)=CC=1C1=CC=C(F)C=C1 QVBVQHTXLPNXEY-ZMFCMNQTSA-N 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
GCVJBTCXIQALGD-UHFFFAOYSA-N 1-(3-piperidin-1-ylphenyl)benzimidazole-5-carbonitrile Chemical compound C1=NC2=CC(C#N)=CC=C2N1C(C=1)=CC=CC=1N1CCCCC1 GCVJBTCXIQALGD-UHFFFAOYSA-N 0.000 claims description 3
LWXPFDFLBTYSIG-UHFFFAOYSA-N 1-(3-pyrrolidin-1-ylphenyl)benzimidazole-5-carbonitrile Chemical compound C1=NC2=CC(C#N)=CC=C2N1C(C=1)=CC=CC=1N1CCCC1 LWXPFDFLBTYSIG-UHFFFAOYSA-N 0.000 claims description 3
KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 claims description 3
LBWHKSKKLOKVJY-UHFFFAOYSA-N 1-[3-(1-methylpiperidin-3-yl)phenyl]-5-phenylbenzimidazole Chemical compound C1N(C)CCCC1C1=CC=CC(N2C3=CC=C(C=C3N=C2)C=2C=CC=CC=2)=C1 LBWHKSKKLOKVJY-UHFFFAOYSA-N 0.000 claims description 3
DKUWVWKVJSAWBS-UHFFFAOYSA-N 1-[3-(4-methylpiperazin-1-yl)phenyl]benzimidazole-5-carbonitrile Chemical compound C1CN(C)CCN1C1=CC=CC(N2C3=CC=C(C=C3N=C2)C#N)=C1 DKUWVWKVJSAWBS-UHFFFAOYSA-N 0.000 claims description 3
AYUBOPKUSRAVHD-UHFFFAOYSA-N 2-(dimethylamino)ethyl 1-[3-[4-(2-ethoxy-2-oxoethyl)piperazin-1-yl]phenyl]benzimidazole-5-carboxylate Chemical compound C1CN(CC(=O)OCC)CCN1C1=CC=CC(N2C3=CC=C(C=C3N=C2)C(=O)OCCN(C)C)=C1 AYUBOPKUSRAVHD-UHFFFAOYSA-N 0.000 claims description 3
GHUWOHMJHNKBFQ-UHFFFAOYSA-N 2-[4-[3-[5-(furan-3-yl)benzimidazol-1-yl]phenyl]piperazin-1-yl]ethanol Chemical compound C1CN(CCO)CCN1C1=CC=CC(N2C3=CC=C(C=C3N=C2)C2=COC=C2)=C1 GHUWOHMJHNKBFQ-UHFFFAOYSA-N 0.000 claims description 3
206010002091 Anaesthesia Diseases 0.000 claims description 3
WDYKPBQYCWHNSE-UHFFFAOYSA-N C(C)OC(=O)C1=CC2=C(N(C=N2)C2=CC(=CC=C2)N2CCOCC2)C=C1 Chemical compound C(C)OC(=O)C1=CC2=C(N(C=N2)C2=CC(=CC=C2)N2CCOCC2)C=C1 WDYKPBQYCWHNSE-UHFFFAOYSA-N 0.000 claims description 3
230000037005 anaesthesia Effects 0.000 claims description 3
229940125877 compound 31 Drugs 0.000 claims description 3
230000002920 convulsive effect Effects 0.000 claims description 3
ILJFWULDHBAIPG-UHFFFAOYSA-N diethyl 2-[[4-[3-[5-(furan-3-yl)benzimidazol-1-yl]phenyl]piperazin-1-yl]methylidene]propanedioate Chemical compound C1CN(C=C(C(=O)OCC)C(=O)OCC)CCN1C1=CC=CC(N2C3=CC=C(C=C3N=C2)C2=COC=C2)=C1 ILJFWULDHBAIPG-UHFFFAOYSA-N 0.000 claims description 3
KNSTZUXNWBANHV-UHFFFAOYSA-N ethyl 1-[3-(1-methylpiperidin-3-yl)phenyl]benzimidazole-5-carboxylate Chemical compound C1=NC2=CC(C(=O)OCC)=CC=C2N1C(C=1)=CC=CC=1C1CCCN(C)C1 KNSTZUXNWBANHV-UHFFFAOYSA-N 0.000 claims description 3
MPECXFJDGYRUIM-UHFFFAOYSA-N ethyl 1-[3-(4-acetylpiperazin-1-yl)phenyl]benzimidazole-5-carboxylate Chemical compound C1=NC2=CC(C(=O)OCC)=CC=C2N1C(C=1)=CC=CC=1N1CCN(C(C)=O)CC1 MPECXFJDGYRUIM-UHFFFAOYSA-N 0.000 claims description 3
125000002541 furyl group Chemical group 0.000 claims description 3
125000000842 isoxazolyl group Chemical group 0.000 claims description 3
RXDBYDKTFGXUNU-UHFFFAOYSA-N methyl 1-[3-(4-methylpiperazin-1-yl)phenyl]benzimidazole-5-carboxylate Chemical compound C1=NC2=CC(C(=O)OC)=CC=C2N1C(C=1)=CC=CC=1N1CCN(C)CC1 RXDBYDKTFGXUNU-UHFFFAOYSA-N 0.000 claims description 3
LRAHMXOFTMAPKU-UHFFFAOYSA-N methyl 2-[1-[1-(3-morpholin-4-ylphenyl)benzimidazol-5-yl]ethylideneamino]oxyacetate Chemical compound C1=NC2=CC(C(C)=NOCC(=O)OC)=CC=C2N1C(C=1)=CC=CC=1N1CCOCC1 LRAHMXOFTMAPKU-UHFFFAOYSA-N 0.000 claims description 3
DQGOHMPFGFSZLF-UHFFFAOYSA-N methyl 2-[4-[3-[5-(furan-3-yl)benzimidazol-1-yl]phenyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OC)CCN1C1=CC=CC(N2C3=CC=C(C=C3N=C2)C2=COC=C2)=C1 DQGOHMPFGFSZLF-UHFFFAOYSA-N 0.000 claims description 3
VBJKBFJXHDTTGE-UHFFFAOYSA-N n-[[1-[3-(1-methylpiperidin-3-yl)phenyl]benzimidazol-5-yl]methylidene]hydroxylamine Chemical compound C1N(C)CCCC1C1=CC=CC(N2C3=CC=C(C=NO)C=C3N=C2)=C1 VBJKBFJXHDTTGE-UHFFFAOYSA-N 0.000 claims description 3
ALDLQMCGOPAQEK-UHFFFAOYSA-N n-ethoxy-1-[1-(3-piperidin-1-ylphenyl)benzimidazol-5-yl]ethanimine Chemical compound C1=NC2=CC(C(C)=NOCC)=CC=C2N1C(C=1)=CC=CC=1N1CCCCC1 ALDLQMCGOPAQEK-UHFFFAOYSA-N 0.000 claims description 3
XIQWHYSEDJCWDQ-UHFFFAOYSA-N n-ethoxy-1-[1-[3-(1-methyl-3,6-dihydro-2h-pyridin-5-yl)phenyl]benzimidazol-5-yl]ethanimine Chemical compound C1=NC2=CC(C(C)=NOCC)=CC=C2N1C(C=1)=CC=CC=1C1=CCCN(C)C1 XIQWHYSEDJCWDQ-UHFFFAOYSA-N 0.000 claims description 3
125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
125000003386 piperidinyl group Chemical group 0.000 claims description 3
WGPNSQZKYGFBCJ-UHFFFAOYSA-N propan-2-yl 1-(3-morpholin-4-ylphenyl)benzimidazole-5-carboxylate Chemical compound C1=NC2=CC(C(=O)OC(C)C)=CC=C2N1C(C=1)=CC=CC=1N1CCOCC1 WGPNSQZKYGFBCJ-UHFFFAOYSA-N 0.000 claims description 3
VMLDPKJACQGLQU-UHFFFAOYSA-N propan-2-yl 1-(3-piperidin-1-ylphenyl)benzimidazole-5-carboxylate Chemical compound C1=NC2=CC(C(=O)OC(C)C)=CC=C2N1C(C=1)=CC=CC=1N1CCCCC1 VMLDPKJACQGLQU-UHFFFAOYSA-N 0.000 claims description 3
OTQHHGWRWNRQAW-UHFFFAOYSA-N pyridin-2-ylmethyl 3-(5-acetylbenzimidazol-1-yl)-N-propan-2-yloxybenzenecarboximidate Chemical compound C=1C=CC(N2C3=CC=C(C=C3N=C2)C(C)=O)=CC=1C(=NOC(C)C)OCC1=CC=CC=N1 OTQHHGWRWNRQAW-UHFFFAOYSA-N 0.000 claims description 3
XDNUINMPVLWPNH-UHFFFAOYSA-N pyridin-2-ylmethyl 3-(5-phenylbenzimidazol-1-yl)benzoate Chemical compound C=1C=CC(N2C3=CC=C(C=C3N=C2)C=2C=CC=CC=2)=CC=1C(=O)OCC1=CC=CC=N1 XDNUINMPVLWPNH-UHFFFAOYSA-N 0.000 claims description 3
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 3
SLVHKHFRLHRTLE-UHFFFAOYSA-N (1-methylpiperidin-3-yl) 3-(5-acetylbenzimidazol-1-yl)-N-propan-2-yloxybenzenecarboximidate Chemical compound C=1C=CC(N2C3=CC=C(C=C3N=C2)C(C)=O)=CC=1C(=NOC(C)C)OC1CCCN(C)C1 SLVHKHFRLHRTLE-UHFFFAOYSA-N 0.000 claims description 2
KRIWIRSMQRQYJG-DLBZAZTESA-N (2s,3s)-3-[[7-(benzylamino)-3-propan-2-ylpyrazolo[1,5-a]pyrimidin-5-yl]amino]butane-1,2,4-triol Chemical compound C=1C(N[C@@H](CO)[C@H](O)CO)=NC2=C(C(C)C)C=NN2C=1NCC1=CC=CC=C1 KRIWIRSMQRQYJG-DLBZAZTESA-N 0.000 claims description 2
IGVKWAAPMVVTFX-BUHFOSPRSA-N (e)-octadec-5-en-7,9-diynoic acid Chemical compound CCCCCCCCC#CC#C\C=C\CCCC(O)=O IGVKWAAPMVVTFX-BUHFOSPRSA-N 0.000 claims description 2
AYKMHLURBOFUEW-UHFFFAOYSA-N 1-[1-[3-(1-methylpiperidin-3-yl)phenyl]benzimidazol-5-yl]-n-propan-2-yloxyethanimine Chemical compound C1=NC2=CC(C(C)=NOC(C)C)=CC=C2N1C(C=1)=CC=CC=1C1CCCN(C)C1 AYKMHLURBOFUEW-UHFFFAOYSA-N 0.000 claims description 2
ZOHYWRNYWSESBR-UHFFFAOYSA-N 1-[1-[3-[4-(c-methyl-n-propan-2-yloxycarbonimidoyl)piperazin-1-yl]phenyl]benzimidazol-5-yl]ethanone Chemical compound C1CN(C(C)=NOC(C)C)CCN1C1=CC=CC(N2C3=CC=C(C=C3N=C2)C(C)=O)=C1 ZOHYWRNYWSESBR-UHFFFAOYSA-N 0.000 claims description 2
ABPPKYPSFJNKLP-UHFFFAOYSA-N 1-[3-(1-methylpiperidin-3-yl)phenyl]benzimidazole-5-carbonitrile Chemical compound C1N(C)CCCC1C1=CC=CC(N2C3=CC=C(C=C3N=C2)C#N)=C1 ABPPKYPSFJNKLP-UHFFFAOYSA-N 0.000 claims description 2
NNDIFHXWZCSWLB-UHFFFAOYSA-N 2-(dimethylamino)ethyl 3-[5-(furan-3-yl)benzimidazol-1-yl]benzoate Chemical compound CN(C)CCOC(=O)C1=CC=CC(N2C3=CC=C(C=C3N=C2)C2=COC=C2)=C1 NNDIFHXWZCSWLB-UHFFFAOYSA-N 0.000 claims description 2
AKBHYCHPWZPGAH-UHFFFAOYSA-N 2-[3-[(3-chloro-4-methylphenyl)methoxy]azetidine-1-carbonyl]-7-oxa-5-azaspiro[3.4]octan-6-one Chemical compound CC1=C(Cl)C=C(COC2CN(C2)C(=O)C2CC3(C2)COC(=O)N3)C=C1 AKBHYCHPWZPGAH-UHFFFAOYSA-N 0.000 claims description 2
QXUICGFRIHTVMU-UHFFFAOYSA-N 2-[4-[3-[5-(c-methyl-n-propan-2-yloxycarbonimidoyl)benzimidazol-1-yl]phenyl]piperazin-1-yl]ethanol Chemical compound C1=NC2=CC(C(C)=NOC(C)C)=CC=C2N1C(C=1)=CC=CC=1N1CCN(CCO)CC1 QXUICGFRIHTVMU-UHFFFAOYSA-N 0.000 claims description 2
OZVNQWJJBJFKOK-UHFFFAOYSA-N 2-[4-[3-[5-[c-methyl-n-[(2-methylpropan-2-yl)oxy]carbonimidoyl]benzimidazol-1-yl]phenyl]piperazin-1-yl]ethanol Chemical compound C1=NC2=CC(C(=NOC(C)(C)C)C)=CC=C2N1C(C=1)=CC=CC=1N1CCN(CCO)CC1 OZVNQWJJBJFKOK-UHFFFAOYSA-N 0.000 claims description 2
MIWGBXAQXKXRPQ-UHFFFAOYSA-N 3-cyclopropyl-5-[1-[3-(1-methylpiperidin-3-yl)phenyl]benzimidazol-5-yl]-1,2,4-oxadiazole Chemical compound C1N(C)CCCC1C1=CC=CC(N2C3=CC=C(C=C3N=C2)C=2ON=C(N=2)C2CC2)=C1 MIWGBXAQXKXRPQ-UHFFFAOYSA-N 0.000 claims description 2
QOTYCRJYLMSMSW-UHFFFAOYSA-N 5-(furan-3-yl)-1-[3-(1-methylpiperidin-3-yl)phenyl]benzimidazole Chemical compound C1N(C)CCCC1C1=CC=CC(N2C3=CC=C(C=C3N=C2)C2=COC=C2)=C1 QOTYCRJYLMSMSW-UHFFFAOYSA-N 0.000 claims description 2
KYRZWXOASSXTOD-UHFFFAOYSA-N 5-tert-butyl-1-[3-(1-methylpiperidin-3-yl)phenyl]benzimidazole Chemical compound C1N(C)CCCC1C1=CC=CC(N2C3=CC=C(C=C3N=C2)C(C)(C)C)=C1 KYRZWXOASSXTOD-UHFFFAOYSA-N 0.000 claims description 2
RNIVGJVALWHDLV-UHFFFAOYSA-N COC(=O)CC1N(CCNC1)C1=CC=C(C=C1)N1C=NC2=C1C=CC=C2 Chemical compound COC(=O)CC1N(CCNC1)C1=CC=C(C=C1)N1C=NC2=C1C=CC=C2 RNIVGJVALWHDLV-UHFFFAOYSA-N 0.000 claims description 2
AKQOBHZKBDHWQI-BZEFIUHZSA-N O[C@H]1C[C@@H](CCC1)N1C(C2(C3=C1N=C(N=C3)NC1=CC=C(C=C1)S(=O)(=O)NC([2H])([2H])[2H])CC2)=O Chemical compound O[C@H]1C[C@@H](CCC1)N1C(C2(C3=C1N=C(N=C3)NC1=CC=C(C=C1)S(=O)(=O)NC([2H])([2H])[2H])CC2)=O AKQOBHZKBDHWQI-BZEFIUHZSA-N 0.000 claims description 2
229940125907 SJ995973 Drugs 0.000 claims description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
125000005518 carboxamido group Chemical group 0.000 claims description 2
229940125796 compound 3d Drugs 0.000 claims description 2
229940126115 compound 4f Drugs 0.000 claims description 2
229940125880 compound 4j Drugs 0.000 claims description 2
229940127108 compound 5g Drugs 0.000 claims description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
VXCDZSPJDBMPCO-UHFFFAOYSA-N ethyl 1-[3-[4-(2-hydroxyethyl)piperazin-1-yl]phenyl]benzimidazole-5-carboxylate Chemical compound C1=NC2=CC(C(=O)OCC)=CC=C2N1C(C=1)=CC=CC=1N1CCN(CCO)CC1 VXCDZSPJDBMPCO-UHFFFAOYSA-N 0.000 claims description 2
AXLJBGTZVRRITO-UHFFFAOYSA-N ethyl 2-[1-[1-[3-[4-(2-hydroxyethyl)piperazin-1-yl]phenyl]benzimidazol-5-yl]ethylideneamino]oxyacetate Chemical compound C1=NC2=CC(C(C)=NOCC(=O)OCC)=CC=C2N1C(C=1)=CC=CC=1N1CCN(CCO)CC1 AXLJBGTZVRRITO-UHFFFAOYSA-N 0.000 claims description 2
PANIQKYBXHWNEP-UHFFFAOYSA-N ethyl 2-[1-[3-(4-methylpiperazin-1-yl)phenyl]benzimidazol-5-yl]acetate Chemical compound C1=NC2=CC(CC(=O)OCC)=CC=C2N1C(C=1)=CC=CC=1N1CCN(C)CC1 PANIQKYBXHWNEP-UHFFFAOYSA-N 0.000 claims description 2
BAEZPJMGPJBLOJ-UHFFFAOYSA-N ethyl 2-[1-[3-(5-acetylbenzimidazol-1-yl)phenyl]piperidin-4-yl]-n-ethoxyethanimidate Chemical compound C1CC(CC(=NOCC)OCC)CCN1C1=CC=CC(N2C3=CC=C(C=C3N=C2)C(C)=O)=C1 BAEZPJMGPJBLOJ-UHFFFAOYSA-N 0.000 claims description 2
CYFSMPVYJUBFLN-UHFFFAOYSA-N ethyl 2-[4-[3-[5-(furan-3-yl)benzimidazol-1-yl]phenyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCN1C1=CC=CC(N2C3=CC=C(C=C3N=C2)C2=COC=C2)=C1 CYFSMPVYJUBFLN-UHFFFAOYSA-N 0.000 claims description 2
RTAIZRVDGGEMOO-UHFFFAOYSA-N ethyl 3-[4-[3-(5-acetylbenzimidazol-1-yl)phenyl]piperazin-1-yl]-2-(C-ethoxy-N-propan-2-yloxycarbonimidoyl)prop-2-enoate Chemical compound C1CN(C=C(C(=O)OCC)C(OCC)=NOC(C)C)CCN1C1=CC=CC(N2C3=CC=C(C=C3N=C2)C(C)=O)=C1 RTAIZRVDGGEMOO-UHFFFAOYSA-N 0.000 claims description 2
MUTCAPXLKRYEPR-ITWZMISCSA-N methyl (e,3r,5s)-7-[4-bromo-2,3-bis(4-fluorophenyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyhept-6-enoate Chemical compound COC(=O)C[C@H](O)C[C@H](O)\C=C\N1C(C(C)C)=C(Br)C(C=2C=CC(F)=CC=2)=C1C1=CC=C(F)C=C1 MUTCAPXLKRYEPR-ITWZMISCSA-N 0.000 claims description 2
JOWSJYSXSKUNHQ-UHFFFAOYSA-N methyl 2-[4-[3-(5-acetylbenzimidazol-1-yl)phenyl]piperazin-1-yl]-N-propan-2-yloxyethanimidate Chemical compound C1CN(CC(OC)=NOC(C)C)CCN1C1=CC=CC(N2C3=CC=C(C=C3N=C2)C(C)=O)=C1 JOWSJYSXSKUNHQ-UHFFFAOYSA-N 0.000 claims description 2
VBDRJNSUUNVOPL-UHFFFAOYSA-N methyl 3-[1-(3-morpholin-4-ylphenyl)benzimidazol-5-yl]prop-2-enoate Chemical compound C1=NC2=CC(C=CC(=O)OC)=CC=C2N1C(C=1)=CC=CC=1N1CCOCC1 VBDRJNSUUNVOPL-UHFFFAOYSA-N 0.000 claims description 2
WNKBVASXOLYLAC-UHFFFAOYSA-N methyl 3-[4-[3-[5-(furan-3-yl)benzimidazol-1-yl]phenyl]piperazin-1-yl]prop-2-enoate Chemical compound C1CN(C=CC(=O)OC)CCN1C1=CC=CC(N2C3=CC=C(C=C3N=C2)C2=COC=C2)=C1 WNKBVASXOLYLAC-UHFFFAOYSA-N 0.000 claims description 2
XZMHJYWMCRQSSI-UHFFFAOYSA-N n-[5-[2-(3-acetylanilino)-1,3-thiazol-4-yl]-4-methyl-1,3-thiazol-2-yl]benzamide Chemical compound CC(=O)C1=CC=CC(NC=2SC=C(N=2)C2=C(N=C(NC(=O)C=3C=CC=CC=3)S2)C)=C1 XZMHJYWMCRQSSI-UHFFFAOYSA-N 0.000 claims description 2
RDHBLALFSYHJJT-UHFFFAOYSA-N n-[[1-(3-piperidin-1-ylphenyl)benzimidazol-5-yl]methylidene]hydroxylamine Chemical compound C1=NC2=CC(C=NO)=CC=C2N1C(C=1)=CC=CC=1N1CCCCC1 RDHBLALFSYHJJT-UHFFFAOYSA-N 0.000 claims description 2
DIHXEQDJAHTVTN-UHFFFAOYSA-N n-[[1-(3-pyrrolidin-1-ylphenyl)benzimidazol-5-yl]methylidene]hydroxylamine Chemical compound C1=NC2=CC(C=NO)=CC=C2N1C(C=1)=CC=CC=1N1CCCC1 DIHXEQDJAHTVTN-UHFFFAOYSA-N 0.000 claims description 2
WOZCXIMLACJTPL-UHFFFAOYSA-N n-[[1-[3-(4-methylpiperazin-1-yl)phenyl]benzimidazol-5-yl]methylidene]hydroxylamine Chemical compound C1CN(C)CCN1C1=CC=CC(N2C3=CC=C(C=NO)C=C3N=C2)=C1 WOZCXIMLACJTPL-UHFFFAOYSA-N 0.000 claims description 2
BPPRYIIZWWHEPR-UHFFFAOYSA-N n-ethoxy-1-[1-(3-pyrrolidin-1-ylphenyl)benzimidazol-5-yl]ethanimine Chemical compound C1=NC2=CC(C(C)=NOCC)=CC=C2N1C(C=1)=CC=CC=1N1CCCC1 BPPRYIIZWWHEPR-UHFFFAOYSA-N 0.000 claims description 2
HPXSSCBMYWFFIB-UHFFFAOYSA-N n-ethoxy-1-[1-[3-(4-methylpiperazin-1-yl)phenyl]benzimidazol-5-yl]ethanimine Chemical compound C1=NC2=CC(C(C)=NOCC)=CC=C2N1C(C=1)=CC=CC=1N1CCN(C)CC1 HPXSSCBMYWFFIB-UHFFFAOYSA-N 0.000 claims description 2
OPHPQBJTRCWHHW-UHFFFAOYSA-N n-ethoxy-1-[1-[3-(pyrrolidin-1-ylmethyl)phenyl]benzimidazol-5-yl]ethanimine Chemical compound C1=NC2=CC(C(C)=NOCC)=CC=C2N1C(C=1)=CC=CC=1CN1CCCC1 OPHPQBJTRCWHHW-UHFFFAOYSA-N 0.000 claims description 2
OXYXREHEDMZNLR-UHFFFAOYSA-N n-methoxy-1-[1-(3-piperidin-1-ylphenyl)benzimidazol-5-yl]methanimine Chemical compound C1=NC2=CC(C=NOC)=CC=C2N1C(C=1)=CC=CC=1N1CCCCC1 OXYXREHEDMZNLR-UHFFFAOYSA-N 0.000 claims description 2
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 2
CIWUBESBWRSUJY-UHFFFAOYSA-N propan-2-yl 1-[3-(4-methylpiperazin-1-yl)phenyl]benzimidazole-5-carboxylate Chemical compound C1=NC2=CC(C(=O)OC(C)C)=CC=C2N1C(C=1)=CC=CC=1N1CCN(C)CC1 CIWUBESBWRSUJY-UHFFFAOYSA-N 0.000 claims description 2
PSMSKHAYMKLTOP-UHFFFAOYSA-N pyridin-3-ylmethyl 1-[3-(1-methylpiperidin-3-yl)phenyl]benzimidazole-5-carboxylate Chemical compound C1N(C)CCCC1C1=CC=CC(N2C3=CC=C(C=C3N=C2)C(=O)OCC=2C=NC=CC=2)=C1 PSMSKHAYMKLTOP-UHFFFAOYSA-N 0.000 claims description 2
125000005942 tetrahydropyridyl group Chemical group 0.000 claims description 2
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 5
OVDGUTHABMXVMI-UHFFFAOYSA-N 3-nitro-4-(propylamino)benzoic acid Chemical compound CCCNC1=CC=C(C(O)=O)C=C1[N+]([O-])=O OVDGUTHABMXVMI-UHFFFAOYSA-N 0.000 claims 3
OMBVEVHRIQULKW-DNQXCXABSA-M (3r,5r)-7-[3-(4-fluorophenyl)-8-oxo-7-phenyl-1-propan-2-yl-5,6-dihydro-4h-pyrrolo[2,3-c]azepin-2-yl]-3,5-dihydroxyheptanoate Chemical compound O=C1C=2N(C(C)C)C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C=3C=CC(F)=CC=3)C=2CCCN1C1=CC=CC=C1 OMBVEVHRIQULKW-DNQXCXABSA-M 0.000 claims 2
JGMXNNSYEFOBHQ-OWOJBTEDSA-N 2-[(e)-4-morpholin-4-ylbut-2-enyl]-1,1-dioxothieno[3,2-e]thiazine-6-sulfonamide Chemical compound O=S1(=O)C=2SC(S(=O)(=O)N)=CC=2C=CN1C\C=C\CN1CCOCC1 JGMXNNSYEFOBHQ-OWOJBTEDSA-N 0.000 claims 2
TZYWCYJVHRLUCT-VABKMULXSA-N N-benzyloxycarbonyl-L-leucyl-L-leucyl-L-leucinal Chemical compound CC(C)C[C@@H](C=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)OCC1=CC=CC=C1 TZYWCYJVHRLUCT-VABKMULXSA-N 0.000 claims 2
YFOSBWWRMNGTNH-UHFFFAOYSA-N ethyl 1-[3-[4-(2-ethoxy-2-oxoethyl)piperazin-1-yl]phenyl]benzimidazole-5-carboxylate Chemical compound C1CN(CC(=O)OCC)CCN1C1=CC=CC(N2C3=CC=C(C=C3N=C2)C(=O)OCC)=C1 YFOSBWWRMNGTNH-UHFFFAOYSA-N 0.000 claims 2
URFXQXNVADAKIG-UHFFFAOYSA-N ethyl 2-[4-[3-(5-acetylbenzimidazol-1-yl)phenyl]piperazin-1-yl]-n-hydroxyethanimidate Chemical compound C1CN(CC(OCC)=NO)CCN1C1=CC=CC(N2C3=CC=C(C=C3N=C2)C(C)=O)=C1 URFXQXNVADAKIG-UHFFFAOYSA-N 0.000 claims 2
WDYDSAZPLMOVET-UHFFFAOYSA-N methyl 1-[3-(4-acetylpiperazin-2-yl)phenyl]benzimidazole-5-carboxylate Chemical compound C1=NC2=CC(C(=O)OC)=CC=C2N1C(C=1)=CC=CC=1C1CN(C(C)=O)CCN1 WDYDSAZPLMOVET-UHFFFAOYSA-N 0.000 claims 2
IZGDXVLRMHXOJV-SFHVURJKSA-N (3s)-4-[2-[2-(4-fluoro-3-methylphenyl)-4-methyl-6-propan-2-ylphenyl]ethyl-hydroxyphosphoryl]-3-hydroxybutanoic acid Chemical compound CC(C)C1=CC(C)=CC(C=2C=C(C)C(F)=CC=2)=C1CCP(O)(=O)C[C@@H](O)CC(O)=O IZGDXVLRMHXOJV-SFHVURJKSA-N 0.000 claims 1
MOQCFMZWVKQBAP-UHFFFAOYSA-N 1-[3,5-bis(trifluoromethyl)benzoyl]-n-(4-chlorophenyl)piperidine-3-carboxamide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C(=O)N2CC(CCC2)C(=O)NC=2C=CC(Cl)=CC=2)=C1 MOQCFMZWVKQBAP-UHFFFAOYSA-N 0.000 claims 1
PSWDQTMAUUQILQ-UHFFFAOYSA-N 2-[(6-methoxy-4-methylquinazolin-2-yl)amino]-5,6-dimethyl-1h-pyrimidin-4-one Chemical compound N1=C(C)C2=CC(OC)=CC=C2N=C1NC1=NC(=O)C(C)=C(C)N1 PSWDQTMAUUQILQ-UHFFFAOYSA-N 0.000 claims 1
UFMQJYHLIUACCG-UHFFFAOYSA-N 8-nitroindolo[2,1-b]quinazoline-6,12-dione Chemical compound C1=CC=C2C(=O)N3C4=CC=C([N+](=O)[O-])C=C4C(=O)C3=NC2=C1 UFMQJYHLIUACCG-UHFFFAOYSA-N 0.000 claims 1
XOJIWLOIBYITQL-UHFFFAOYSA-N C(C)(C1=CC2=C(N(C=N2)C2=CC(=CC=C2)N2CCN(CC2)CCO)C=C1)=NO Chemical compound C(C)(C1=CC2=C(N(C=N2)C2=CC(=CC=C2)N2CCN(CC2)CCO)C=C1)=NO XOJIWLOIBYITQL-UHFFFAOYSA-N 0.000 claims 1
TZCCKCLHNUSAMQ-DUGSHLAESA-N NC(=O)C[C@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](Cc2ccc(F)cc2)NC(=O)[C@H](Cc3c[nH]c4ccccc34)NC(=O)Cc5cccs5)C(=O)N Chemical compound NC(=O)C[C@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](Cc2ccc(F)cc2)NC(=O)[C@H](Cc3c[nH]c4ccccc34)NC(=O)Cc5cccs5)C(=O)N TZCCKCLHNUSAMQ-DUGSHLAESA-N 0.000 claims 1
239000000654 additive Substances 0.000 claims 1
230000000996 additive effect Effects 0.000 claims 1
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 1
XMNGGULIGPHBDR-UHFFFAOYSA-N benzyl 1-[3-(1-methylpiperidin-3-yl)phenyl]benzimidazole-5-carboxylate Chemical compound C1N(C)CCCC1C1=CC=CC(N2C3=CC=C(C=C3N=C2)C(=O)OCC=2C=CC=CC=2)=C1 XMNGGULIGPHBDR-UHFFFAOYSA-N 0.000 claims 1
229940126136 compound 5i Drugs 0.000 claims 1
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IHSUFLCKRIHFGY-UHFFFAOYSA-N ethyl 2-piperidin-4-ylacetate Chemical compound CCOC(=O)CC1CCNCC1 IHSUFLCKRIHFGY-UHFFFAOYSA-N 0.000 description 1
ROTLCYMZFRFVES-UHFFFAOYSA-N ethyl 3-(1h-benzimidazol-2-yl)benzoate Chemical compound CCOC(=O)C1=CC=CC(C=2NC3=CC=CC=C3N=2)=C1 ROTLCYMZFRFVES-UHFFFAOYSA-N 0.000 description 1
LQTUGHREZCYQEM-UHFFFAOYSA-N ethyl 3-[4-(furan-3-yl)-2-nitroanilino]benzoate Chemical compound CCOC(=O)C1=CC=CC(NC=2C(=CC(=CC=2)C2=COC=C2)[N+]([O-])=O)=C1 LQTUGHREZCYQEM-UHFFFAOYSA-N 0.000 description 1
BLNLZRQIUGDTAO-UHFFFAOYSA-N ethyl 4-chloro-3-nitrobenzoate Chemical compound CCOC(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 BLNLZRQIUGDTAO-UHFFFAOYSA-N 0.000 description 1
UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
230000002964 excitative effect Effects 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000006260 foam Substances 0.000 description 1
210000001061 forehead Anatomy 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
PZJSZBJLOWMDRG-UHFFFAOYSA-N furan-2-ylboronic acid Chemical compound OB(O)C1=CC=CO1 PZJSZBJLOWMDRG-UHFFFAOYSA-N 0.000 description 1
CYEFKCRAAGLNHW-UHFFFAOYSA-N furan-3-ylboronic acid Chemical compound OB(O)C=1C=COC=1 CYEFKCRAAGLNHW-UHFFFAOYSA-N 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000003349 gelling agent Substances 0.000 description 1
229930195712 glutamate Natural products 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
150000002460 imidazoles Chemical class 0.000 description 1
JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
238000011534 incubation Methods 0.000 description 1
230000004941 influx Effects 0.000 description 1
239000003978 infusion fluid Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
108091008042 inhibitory receptors Proteins 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001793 isothiazol-3-yl group Chemical group [H]C1=C([H])C(*)=NS1 0.000 description 1
125000004500 isothiazol-4-yl group Chemical group S1N=CC(=C1)* 0.000 description 1
125000004501 isothiazol-5-yl group Chemical group S1N=CC=C1* 0.000 description 1
125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 description 1
125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 description 1
125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 description 1
125000003965 isoxazolidinyl group Chemical group 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
239000012669 liquid formulation Substances 0.000 description 1
239000006210 lotion Substances 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
210000005171 mammalian brain Anatomy 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
YBXNTIKBYFNCFB-UHFFFAOYSA-N methyl 2-[1-[1-[3-(1-methylpiperidin-3-yl)phenyl]benzimidazol-5-yl]ethylideneamino]oxyacetate Chemical compound C1=NC2=CC(C(C)=NOCC(=O)OC)=CC=C2N1C(C=1)=CC=CC=1C1CCCN(C)C1 YBXNTIKBYFNCFB-UHFFFAOYSA-N 0.000 description 1
FVTZYNDTBQLKKM-UHFFFAOYSA-N methyl 2-[1-[4-[3-(5-acetylbenzimidazol-1-yl)phenyl]piperazin-1-yl]ethylideneamino]oxyacetate Chemical compound C1CN(C(C)=NOCC(=O)OC)CCN1C1=CC=CC(N2C3=CC=C(C=C3N=C2)C(C)=O)=C1 FVTZYNDTBQLKKM-UHFFFAOYSA-N 0.000 description 1
ZLJPXRLXOUUISR-UHFFFAOYSA-N methyl 2-aminooxy-2-methylpropanoate Chemical compound COC(=O)C(C)(C)ON ZLJPXRLXOUUISR-UHFFFAOYSA-N 0.000 description 1
CTSAXXHOGZNKJR-UHFFFAOYSA-N methyl 2-diethoxyphosphorylacetate Chemical compound CCOP(=O)(OCC)CC(=O)OC CTSAXXHOGZNKJR-UHFFFAOYSA-N 0.000 description 1
SDZFFOAJFKWQMS-UHFFFAOYSA-N methyl 3-(1h-benzimidazol-2-yl)benzoate Chemical compound COC(=O)C1=CC=CC(C=2NC3=CC=CC=C3N=2)=C1 SDZFFOAJFKWQMS-UHFFFAOYSA-N 0.000 description 1
FSLFGFPQIKPYCT-UHFFFAOYSA-N methyl 4-[3-(4-acetylpiperazin-1-yl)anilino]-3-nitrobenzoate Chemical compound [O-][N+](=O)C1=CC(C(=O)OC)=CC=C1NC1=CC=CC(N2CCN(CC2)C(C)=O)=C1 FSLFGFPQIKPYCT-UHFFFAOYSA-N 0.000 description 1
IMAKHNTVDGLIRY-UHFFFAOYSA-N methyl prop-2-ynoate Chemical compound COC(=O)C#C IMAKHNTVDGLIRY-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
235000019426 modified starch Nutrition 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
239000002324 mouth wash Substances 0.000 description 1
OMCUPXRCMTUDHI-UHFFFAOYSA-N n'-hydroxycyclopropanecarboximidamide Chemical compound ON=C(N)C1CC1 OMCUPXRCMTUDHI-UHFFFAOYSA-N 0.000 description 1
KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
235000021096 natural sweeteners Nutrition 0.000 description 1
230000001537 neural effect Effects 0.000 description 1
239000002858 neurotransmitter agent Substances 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
NUXCOKIYARRTDC-UHFFFAOYSA-N o-ethylhydroxylamine;hydron;chloride Chemical compound Cl.CCON NUXCOKIYARRTDC-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
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150000007524 organic acids Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 description 1
125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 description 1
125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 description 1
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239000006072 paste Substances 0.000 description 1
235000010603 pastilles Nutrition 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
210000001428 peripheral nervous system Anatomy 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
VJKUPQSHOVKBCO-AHMKVGDJSA-N picrotoxin Chemical compound O=C([C@@]12O[C@@H]1C[C@]1(O)[C@@]32C)O[C@@H]3[C@H]2[C@@H](C(=C)C)[C@@H]1C(=O)O2.O=C([C@@]12O[C@@H]1C[C@]1(O)[C@@]32C)O[C@@H]3[C@H]2[C@@H](C(C)(O)C)[C@@H]1C(=O)O2 VJKUPQSHOVKBCO-AHMKVGDJSA-N 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
108020001213 potassium channel Proteins 0.000 description 1
239000004323 potassium nitrate Substances 0.000 description 1
235000010333 potassium nitrate Nutrition 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
230000008569 process Effects 0.000 description 1
230000000216 proconvulsive effect Effects 0.000 description 1
ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
QYTCRTYEQVJZSM-UHFFFAOYSA-N propan-2-yl 3-nitro-4-(3-piperidin-1-ylanilino)benzoate Chemical compound [O-][N+](=O)C1=CC(C(=O)OC(C)C)=CC=C1NC1=CC=CC(N2CCCCC2)=C1 QYTCRTYEQVJZSM-UHFFFAOYSA-N 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
SHNUBALDGXWUJI-UHFFFAOYSA-N pyridin-2-ylmethanol Chemical compound OCC1=CC=CC=N1 SHNUBALDGXWUJI-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
229910001495 sodium tetrafluoroborate Inorganic materials 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
DUTLKLPXMPHUMV-UHFFFAOYSA-N tert-butyl 4-(3-nitrophenyl)piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=CC([N+]([O-])=O)=C1 DUTLKLPXMPHUMV-UHFFFAOYSA-N 0.000 description 1
CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000012085 test solution Substances 0.000 description 1
125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 description 1
125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 description 1
230000008719 thickening Effects 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
229940029284 trichlorofluoromethane Drugs 0.000 description 1
GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
210000003462 vein Anatomy 0.000 description 1

Classifications

- 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
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
- 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
- A61P25/22—Anxiolytics
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Pain & Pain Management (AREA)
Hospice & Palliative Care (AREA)
Psychiatry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

SK424-99A 1996-10-21 1997-10-21 1-phenyl-benzimidazole compounds and their use as gabaa receptor modulators SK42499A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DK115796		1996-10-21
PCT/DK1997/000462 WO1998017651A1 (fr)	1996-10-21	1997-10-21	Composes 1-phenyl-benzimidazole et leur utilisation comme modulateurs du recepteur baga-¿a?

Publications (1)

Publication Number	Publication Date
SK42499A3 true SK42499A3 (en)	2000-05-16

Family

ID=8101649

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK424-99A SK42499A3 (en)	1996-10-21	1997-10-21	1-phenyl-benzimidazole compounds and their use as gabaa receptor modulators

Country Status (13)

Country	Link
US (3)	US6218547B1 (fr)
EP (1)	EP0934281B1 (fr)
JP (1)	JP2001502675A (fr)
CN (1)	CN1115336C (fr)
AT (1)	ATE454375T1 (fr)
AU (1)	AU726447B2 (fr)
CA (1)	CA2267114A1 (fr)
CZ (1)	CZ127299A3 (fr)
DE (1)	DE69739733D1 (fr)
NZ (1)	NZ334868A (fr)
RU (1)	RU2194699C2 (fr)
SK (1)	SK42499A3 (fr)
WO (1)	WO1998017651A1 (fr)

Families Citing this family (49)

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1997
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- 1997-10-21 JP JP10518852A patent/JP2001502675A/ja active Pending
- 1997-10-21 RU RU99110508/04A patent/RU2194699C2/ru not_active IP Right Cessation
- 1997-10-21 US US09/269,643 patent/US6218547B1/en not_active Expired - Fee Related
- 1997-10-21 CN CN97198988A patent/CN1115336C/zh not_active Expired - Fee Related
- 1997-10-21 NZ NZ334868A patent/NZ334868A/en unknown
- 1997-10-21 SK SK424-99A patent/SK42499A3/sk unknown
- 1997-10-21 WO PCT/DK1997/000462 patent/WO1998017651A1/fr not_active Ceased
- 1997-10-21 AT AT97944749T patent/ATE454375T1/de not_active IP Right Cessation
- 1997-10-21 EP EP97944749A patent/EP0934281B1/fr not_active Expired - Lifetime
- 1997-10-21 DE DE69739733T patent/DE69739733D1/de not_active Expired - Lifetime
- 1997-10-21 CA CA002267114A patent/CA2267114A1/fr not_active Abandoned
- 1997-10-21 AU AU46161/97A patent/AU726447B2/en not_active Ceased
2001
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2002
- 2002-11-20 US US10/299,854 patent/US6710044B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CN1234025A (zh)	1999-11-03
CZ127299A3 (cs)	1999-09-15
AU4616197A (en)	1998-05-15
CA2267114A1 (fr)	1998-04-30
CN1115336C (zh)	2003-07-23
WO1998017651A1 (fr)	1998-04-30
RU2194699C2 (ru)	2002-12-20
EP0934281B1 (fr)	2010-01-06
JP2001502675A (ja)	2001-02-27
AU726447B2 (en)	2000-11-09
EP0934281A1 (fr)	1999-08-11
US20030166638A1 (en)	2003-09-04
DE69739733D1 (de)	2010-02-25
US6218547B1 (en)	2001-04-17
US6710044B2 (en)	2004-03-23
ATE454375T1 (de)	2010-01-15
NZ334868A (en)	2001-02-23
US6503925B1 (en)	2003-01-07

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CZ287545B6 (en)	2000-12-13	Benzimidazole derivatives, pharmaceutical preparation in which they are comprised and their use
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