JP2006501246A5 - - Google Patents
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- JP2006501246A5 JP2006501246A5 JP2004531954A JP2004531954A JP2006501246A5 JP 2006501246 A5 JP2006501246 A5 JP 2006501246A5 JP 2004531954 A JP2004531954 A JP 2004531954A JP 2004531954 A JP2004531954 A JP 2004531954A JP 2006501246 A5 JP2006501246 A5 JP 2006501246A5
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- alkyl
- alkoxy
- bipyridinyl
- tetrahydro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 125000004432 carbon atom Chemical group C* 0.000 claims 1607
- -1 cyano, hydroxyl Chemical group 0.000 claims 662
- 125000000217 alkyl group Chemical group 0.000 claims 587
- 125000003545 alkoxy group Chemical group 0.000 claims 398
- VEKIYFGCEAJDDT-UHFFFAOYSA-N 2-pyridin-3-ylpyridine Chemical group N1=CC=CC=C1C1=CC=CN=C1 VEKIYFGCEAJDDT-UHFFFAOYSA-N 0.000 claims 274
- 229910052736 halogen Inorganic materials 0.000 claims 272
- 150000002367 halogens Chemical class 0.000 claims 254
- 125000003118 aryl group Chemical group 0.000 claims 209
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 175
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 160
- 125000004093 cyano group Chemical group *C#N 0.000 claims 131
- 125000001072 heteroaryl group Chemical group 0.000 claims 124
- 125000004663 dialkyl amino group Chemical group 0.000 claims 122
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 claims 118
- 125000003342 alkenyl group Chemical group 0.000 claims 110
- 125000000753 cycloalkyl group Chemical group 0.000 claims 110
- 125000000304 alkynyl group Chemical group 0.000 claims 108
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 108
- 125000006413 ring segment Chemical group 0.000 claims 96
- 229920006395 saturated elastomer Polymers 0.000 claims 92
- 229910052760 oxygen Inorganic materials 0.000 claims 90
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 80
- 150000001350 alkyl halides Chemical class 0.000 claims 76
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 75
- 125000004414 alkyl thio group Chemical group 0.000 claims 75
- 150000001875 compounds Chemical class 0.000 claims 74
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 73
- 229910052717 sulfur Inorganic materials 0.000 claims 73
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 72
- 125000004043 oxo group Chemical group O=* 0.000 claims 70
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 69
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 68
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 64
- 125000000623 heterocyclic group Chemical group 0.000 claims 63
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 60
- 125000004076 pyridyl group Chemical group 0.000 claims 60
- 125000005842 heteroatom Chemical group 0.000 claims 59
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 53
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 52
- 125000004423 acyloxy group Chemical group 0.000 claims 50
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims 50
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 48
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 47
- 229910052757 nitrogen Inorganic materials 0.000 claims 46
- 125000004429 atom Chemical group 0.000 claims 40
- 125000003226 pyrazolyl group Chemical group 0.000 claims 37
- 229910052799 carbon Inorganic materials 0.000 claims 36
- 125000002252 acyl group Chemical group 0.000 claims 34
- 125000000168 pyrrolyl group Chemical group 0.000 claims 34
- 150000003839 salts Chemical class 0.000 claims 31
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical group C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 claims 30
- 125000002883 imidazolyl group Chemical group 0.000 claims 30
- 125000001786 isothiazolyl group Chemical group 0.000 claims 30
- 125000000842 isoxazolyl group Chemical group 0.000 claims 30
- 125000002971 oxazolyl group Chemical group 0.000 claims 30
- 125000001424 substituent group Chemical group 0.000 claims 30
- 125000000335 thiazolyl group Chemical group 0.000 claims 30
- 125000001425 triazolyl group Chemical group 0.000 claims 30
- 125000003282 alkyl amino group Chemical group 0.000 claims 28
- 239000008194 pharmaceutical composition Substances 0.000 claims 28
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims 22
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 22
- 125000001544 thienyl group Chemical group 0.000 claims 22
- 125000003302 alkenyloxy group Chemical group 0.000 claims 16
- 125000005110 aryl thio group Chemical group 0.000 claims 16
- 125000004430 oxygen atom Chemical group O* 0.000 claims 16
- 125000004434 sulfur atom Chemical group 0.000 claims 16
- 125000003435 aroyl group Chemical group 0.000 claims 15
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 15
- 125000002619 bicyclic group Chemical group 0.000 claims 15
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 14
- 239000000203 mixture Substances 0.000 claims 14
- 206010012289 Dementia Diseases 0.000 claims 12
- 125000002947 alkylene group Chemical group 0.000 claims 12
- 208000010877 cognitive disease Diseases 0.000 claims 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 11
- 125000003107 substituted aryl group Chemical group 0.000 claims 11
- 239000003937 drug carrier Substances 0.000 claims 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims 9
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims 8
- 208000028698 Cognitive impairment Diseases 0.000 claims 7
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 7
- 208000000044 Amnesia Diseases 0.000 claims 6
- 230000032683 aging Effects 0.000 claims 6
- 125000005189 alkyl hydroxy group Chemical group 0.000 claims 6
- 125000004104 aryloxy group Chemical group 0.000 claims 6
- 125000001041 indolyl group Chemical group 0.000 claims 6
- 208000024891 symptom Diseases 0.000 claims 6
- 206010027175 memory impairment Diseases 0.000 claims 5
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 4
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims 4
- 208000024827 Alzheimer disease Diseases 0.000 claims 4
- 208000026139 Memory disease Diseases 0.000 claims 4
- 208000006011 Stroke Diseases 0.000 claims 4
- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 claims 4
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims 4
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims 4
- 125000005433 dihydrobenzodioxinyl group Chemical group O1C(COC2=C1C=CC=C2)* 0.000 claims 4
- 230000006984 memory degeneration Effects 0.000 claims 4
- 208000023060 memory loss Diseases 0.000 claims 4
- 208000027061 mild cognitive impairment Diseases 0.000 claims 4
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 4
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 3
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 3
- LLSRLLPHUVVLQJ-UHFFFAOYSA-N 1-cycloheptyldiazepane Chemical group C1CCCCCC1N1NCCCCC1 LLSRLLPHUVVLQJ-UHFFFAOYSA-N 0.000 claims 2
- ZAPJAISNWWNYTA-UHFFFAOYSA-N 4-[5-[(6-pyridin-3-yl-3,4-dihydro-2H-pyridin-5-ylidene)methyl]thiophen-2-yl]phenol Chemical compound C1=CC(O)=CC=C1C(S1)=CC=C1C=C1C(C=2C=NC=CC=2)=NCCC1 ZAPJAISNWWNYTA-UHFFFAOYSA-N 0.000 claims 2
- FNZAOUNIKFZTKA-UHFFFAOYSA-N 4-[5-[(6-pyridin-3-yl-3,4-dihydro-2H-pyridin-5-ylidene)methyl]thiophen-2-yl]phenol dihydrobromide Chemical compound Br.Br.C1=CC(O)=CC=C1C(S1)=CC=C1C=C1C(C=2C=NC=CC=2)=NCCC1 FNZAOUNIKFZTKA-UHFFFAOYSA-N 0.000 claims 2
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 2
- 206010065040 AIDS dementia complex Diseases 0.000 claims 2
- 208000007848 Alcoholism Diseases 0.000 claims 2
- 208000031091 Amnestic disease Diseases 0.000 claims 2
- 102000013455 Amyloid beta-Peptides Human genes 0.000 claims 2
- 108010090849 Amyloid beta-Peptides Proteins 0.000 claims 2
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 claims 2
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims 2
- 208000020406 Creutzfeldt Jacob disease Diseases 0.000 claims 2
- 208000003407 Creutzfeldt-Jakob Syndrome Diseases 0.000 claims 2
- 208000010859 Creutzfeldt-Jakob disease Diseases 0.000 claims 2
- 206010012335 Dependence Diseases 0.000 claims 2
- 201000010374 Down Syndrome Diseases 0.000 claims 2
- 201000011240 Frontotemporal dementia Diseases 0.000 claims 2
- 206010019196 Head injury Diseases 0.000 claims 2
- 208000010496 Heart Arrest Diseases 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 2
- 208000001456 Jet Lag Syndrome Diseases 0.000 claims 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 2
- 206010057852 Nicotine dependence Diseases 0.000 claims 2
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims 2
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 208000000609 Pick Disease of the Brain Diseases 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 208000028017 Psychotic disease Diseases 0.000 claims 2
- 208000010340 Sleep Deprivation Diseases 0.000 claims 2
- 208000025569 Tobacco Use disease Diseases 0.000 claims 2
- 201000004810 Vascular dementia Diseases 0.000 claims 2
- 102000015296 acetylcholine-gated cation-selective channel activity proteins Human genes 0.000 claims 2
- 108040006409 acetylcholine-gated cation-selective channel activity proteins Proteins 0.000 claims 2
- 230000003213 activating effect Effects 0.000 claims 2
- 230000007000 age related cognitive decline Effects 0.000 claims 2
- 201000007930 alcohol dependence Diseases 0.000 claims 2
- 208000029650 alcohol withdrawal Diseases 0.000 claims 2
- 230000006986 amnesia Effects 0.000 claims 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 2
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 230000002490 cerebral effect Effects 0.000 claims 2
- 206010008118 cerebral infarction Diseases 0.000 claims 2
- 230000001713 cholinergic effect Effects 0.000 claims 2
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 230000006378 damage Effects 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 230000004064 dysfunction Effects 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 230000003492 excitotoxic effect Effects 0.000 claims 2
- 231100000063 excitotoxicity Toxicity 0.000 claims 2
- 238000002695 general anesthesia Methods 0.000 claims 2
- 229930195712 glutamate Natural products 0.000 claims 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 150000003840 hydrochlorides Chemical class 0.000 claims 2
- 208000028867 ischemia Diseases 0.000 claims 2
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims 2
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 claims 2
- 201000003631 narcolepsy Diseases 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 230000004112 neuroprotection Effects 0.000 claims 2
- 230000036407 pain Effects 0.000 claims 2
- VFWZSSRYGCTVFB-UHFFFAOYSA-N phenyl-[5-[(6-pyridin-3-yl-3,4-dihydro-2h-pyridin-5-ylidene)methyl]-1-benzofuran-2-yl]methanone Chemical compound C=1C=CC=CC=1C(=O)C(OC1=CC=2)=CC1=CC=2C=C1CCCN=C1C1=CC=CN=C1 VFWZSSRYGCTVFB-UHFFFAOYSA-N 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 230000004936 stimulating effect Effects 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 125000005338 substituted cycloalkoxy group Chemical group 0.000 claims 2
- 238000002560 therapeutic procedure Methods 0.000 claims 2
- MFOJBKQUEUVDRO-UHFFFAOYSA-N 1-[4-[3-[(6-pyridin-3-yl-3,4-dihydro-2h-pyridin-5-ylidene)methyl]phenyl]-1,4-diazepan-1-yl]propan-1-one Chemical compound C1CN(C(=O)CC)CCCN1C1=CC=CC(C=C2C(=NCCC2)C=2C=NC=CC=2)=C1 MFOJBKQUEUVDRO-UHFFFAOYSA-N 0.000 claims 1
- QNYLQDGPHBPAAW-UHFFFAOYSA-N 1-[4-[4-[(6-pyridin-3-yl-3,4-dihydro-2h-pyridin-5-ylidene)methyl]phenyl]-1,4-diazepan-1-yl]propan-1-one Chemical compound C1CN(C(=O)CC)CCCN1C(C=C1)=CC=C1C=C1C(C=2C=NC=CC=2)=NCCC1 QNYLQDGPHBPAAW-UHFFFAOYSA-N 0.000 claims 1
- ZYHCKUYXMJTKQY-UHFFFAOYSA-N 1-[4-[4-[(6-pyridin-3-yl-3,4-dihydro-2h-pyridin-5-ylidene)methyl]phenyl]piperazin-1-yl]propan-1-one Chemical compound C1CN(C(=O)CC)CCN1C(C=C1)=CC=C1C=C1C(C=2C=NC=CC=2)=NCCC1 ZYHCKUYXMJTKQY-UHFFFAOYSA-N 0.000 claims 1
- MAJCAETUHFGOKP-UHFFFAOYSA-N 2,2,2-trifluoro-1-[4-[4-[(6-pyridin-3-yl-3,4-dihydro-2h-pyridin-5-ylidene)methyl]phenyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C(F)(F)F)CCN1C(C=C1)=CC=C1C=C1C(C=2C=NC=CC=2)=NCCC1 MAJCAETUHFGOKP-UHFFFAOYSA-N 0.000 claims 1
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims 1
- PNFSOTATMWBLOR-UHFFFAOYSA-N 3-[2-[(6-pyridin-3-yl-3,4-dihydro-2h-pyridin-5-ylidene)methyl]pyrrol-1-yl]benzonitrile Chemical compound N#CC1=CC=CC(N2C(=CC=C2)C=C2C(=NCCC2)C=2C=NC=CC=2)=C1 PNFSOTATMWBLOR-UHFFFAOYSA-N 0.000 claims 1
- NLLXCZFSMUXURQ-UHFFFAOYSA-N 3-[5-[[1-[4-(trifluoromethoxy)phenyl]pyrrol-2-yl]methylidene]-3,4-dihydro-2h-pyridin-6-yl]pyridine Chemical group C1=CC(OC(F)(F)F)=CC=C1N1C(C=C2C(=NCCC2)C=2C=NC=CC=2)=CC=C1 NLLXCZFSMUXURQ-UHFFFAOYSA-N 0.000 claims 1
- LUJFDHSHPZYTSN-UHFFFAOYSA-N 3-[5-[[1-[[4-(trifluoromethoxy)phenyl]methyl]pyrrol-2-yl]methylidene]-3,4-dihydro-2h-pyridin-6-yl]pyridine Chemical group C1=CC(OC(F)(F)F)=CC=C1CN1C(C=C2C(=NCCC2)C=2C=NC=CC=2)=CC=C1 LUJFDHSHPZYTSN-UHFFFAOYSA-N 0.000 claims 1
- 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 claims 1
- 206010021143 Hypoxia Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 206010044688 Trisomy 21 Diseases 0.000 claims 1
- 230000003444 anaesthetic effect Effects 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 238000007675 cardiac surgery Methods 0.000 claims 1
- DVXPPDFIFAVKSV-UHFFFAOYSA-N cyclopropyl-[4-[3-[(6-pyridin-3-yl-3,4-dihydro-2h-pyridin-5-ylidene)methyl]phenyl]-1,4-diazepan-1-yl]methanone Chemical compound C1CCN(C=2C=C(C=C3C(=NCCC3)C=3C=NC=CC=3)C=CC=2)CCN1C(=O)C1CC1 DVXPPDFIFAVKSV-UHFFFAOYSA-N 0.000 claims 1
- JEHITFUGEWUVPA-UHFFFAOYSA-N cyclopropyl-[4-[4-[(6-pyridin-3-yl-3,4-dihydro-2h-pyridin-5-ylidene)methyl]phenyl]-1,4-diazepan-1-yl]methanone Chemical compound C1CCN(C=2C=CC(C=C3C(=NCCC3)C=3C=NC=CC=3)=CC=2)CCN1C(=O)C1CC1 JEHITFUGEWUVPA-UHFFFAOYSA-N 0.000 claims 1
- YWPYSGJNWPTQLJ-UHFFFAOYSA-N cyclopropyl-[4-[4-[(6-pyridin-3-yl-3,4-dihydro-2h-pyridin-5-ylidene)methyl]phenyl]piperazin-1-yl]methanone Chemical compound C1CN(C=2C=CC(C=C3C(=NCCC3)C=3C=NC=CC=3)=CC=2)CCN1C(=O)C1CC1 YWPYSGJNWPTQLJ-UHFFFAOYSA-N 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- ZWWCURLKEXEFQT-UHFFFAOYSA-N dinitrogen pentaoxide Chemical compound [O-][N+](=O)O[N+]([O-])=O ZWWCURLKEXEFQT-UHFFFAOYSA-N 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 230000007954 hypoxia Effects 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- ZULLAVFVXBSWQQ-UHFFFAOYSA-N nitro hydrogen carbonate Chemical compound OC(=O)O[N+]([O-])=O ZULLAVFVXBSWQQ-UHFFFAOYSA-N 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 230000005586 smoking cessation Effects 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40698102P | 2002-08-30 | 2002-08-30 | |
| PCT/US2003/027164 WO2004019943A1 (en) | 2002-08-30 | 2003-08-29 | Anabaseine derivatives useful in the treatment of neurodegenerative diseases |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011117305A Division JP2011168617A (ja) | 2002-08-30 | 2011-05-25 | 神経変性疾患の治療において有用なアナバセイン誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006501246A JP2006501246A (ja) | 2006-01-12 |
| JP2006501246A5 true JP2006501246A5 (OSRAM) | 2006-11-09 |
Family
ID=31978399
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004531954A Withdrawn JP2006501246A (ja) | 2002-08-30 | 2003-08-29 | 神経変性疾患の治療において有用なアナバセイン誘導体 |
| JP2011117305A Pending JP2011168617A (ja) | 2002-08-30 | 2011-05-25 | 神経変性疾患の治療において有用なアナバセイン誘導体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011117305A Pending JP2011168617A (ja) | 2002-08-30 | 2011-05-25 | 神経変性疾患の治療において有用なアナバセイン誘導体 |
Country Status (6)
| Country | Link |
|---|---|
| US (3) | US7244745B2 (OSRAM) |
| EP (4) | EP1531820A1 (OSRAM) |
| JP (2) | JP2006501246A (OSRAM) |
| AU (1) | AU2003265842A1 (OSRAM) |
| CA (1) | CA2495248A1 (OSRAM) |
| WO (1) | WO2004019943A1 (OSRAM) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2610795C (en) | 2005-06-07 | 2015-01-06 | University Of Florida Research Foundation, Inc. | 3-arylidene-anabaseine compounds as alpha 7 nicotitnic receptor selective ligands |
| US7662965B2 (en) * | 2006-01-26 | 2010-02-16 | Cornerstone Therapeutics, Inc. | Anabaseine derivatives, pharmaceutical compositions and method of use thereof |
| SA08290475B1 (ar) | 2007-08-02 | 2013-06-22 | Targacept Inc | (2s، 3r)-n-(2-((3-بيردينيل)ميثيل)-1-آزا بيسيكلو[2، 2، 2]أوكت-3-يل)بنزو فيوران-2-كربوكساميد، وصور أملاحه الجديدة وطرق استخدامه |
| JP2011516489A (ja) * | 2008-03-31 | 2011-05-26 | ユニバーシティ・オブ・サウス・フロリダ | 疾患誘発性運動失調症および非運動失調性平衡異常の治療法 |
| TW201031664A (en) | 2009-01-26 | 2010-09-01 | Targacept Inc | Preparation and therapeutic applications of (2S,3R)-N-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)-3,5-difluorobenzamide |
| WO2011009890A2 (en) * | 2009-07-23 | 2011-01-27 | Novartis Ag | Use of azabicycloalkyl derivatives or pyrrolidine-2-one derivatives |
| JO3250B1 (ar) | 2009-09-22 | 2018-09-16 | Novartis Ag | إستعمال منشطات مستقبل نيكوتينيك أسيتيل كولين ألفا 7 |
| PT3029039T (pt) | 2010-05-17 | 2017-11-28 | Forum Pharmaceuticals Inc | Formulações farmacêuticas que compreendem formas cristalinas de cloridrato de (r)-7-cloro-n-(quinuclidin-3-il)benzo(b)tiofeno-2-carboxamida mono-hidratado |
| WO2013090260A1 (en) * | 2011-12-12 | 2013-06-20 | University Of Florida Research Foundation | Nicotinic receptor targeted compounds and compositions |
| EP2846796A4 (en) | 2012-05-08 | 2015-10-21 | Forum Pharmaceuticals Inc | METHODS OF MAINTAINING, PROCESSING OR ENHANCING COGNITIVE FUNCTION |
| IL262957B2 (en) * | 2016-05-12 | 2024-04-01 | Buck Inst Res Aging | 6-Fluorotropistrone and a pharmaceutical formulation comprising it for the relief of amyloid-related diseases |
| CN111808907B (zh) * | 2019-10-09 | 2021-07-09 | 北京原基华毅生物科技有限公司 | 调整觉醒的物质及方法 |
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| DE3508258A1 (de) | 1985-03-08 | 1986-09-18 | Bayer Ag, 5090 Leverkusen | Ss-lactamantibiotika, verfahren zur herstellung und ihre verwendung als und in arzneimitteln |
| EP0573568B1 (en) | 1991-03-01 | 2001-01-24 | University Of Florida Research Foundation, Inc. | Use of nicotinic analogs for treatment of degenerative diseases of the nervous system |
| US5977144A (en) * | 1992-08-31 | 1999-11-02 | University Of Florida | Methods of use and compositions for benzylidene- and cinnamylidene-anabaseines |
| JP3034953B2 (ja) * | 1992-08-31 | 2000-04-17 | ユニバーシティー オブ フロリダ リサーチ ファンデーション，インコーポレーテッド | 神経系の変性疾患の治療に有用なアナバセイン誘導体 |
| CA2186371A1 (en) | 1994-03-25 | 1995-10-05 | Robert T. Foster | Enhancement of the efficacy of dihydropyridines by deuteration |
| US6334997B1 (en) | 1994-03-25 | 2002-01-01 | Isotechnika, Inc. | Method of using deuterated calcium channel blockers |
| US5510355A (en) * | 1994-09-06 | 1996-04-23 | Bencherif; Merouane | Depolarizing skeletal muscle relaxants |
| JP3219946B2 (ja) * | 1994-09-22 | 2001-10-15 | 大鵬薬品工業株式会社 | 新規製造中間体及びピリジン誘導体の製造方法 |
| US20020028798A1 (en) * | 1995-12-12 | 2002-03-07 | Omeros Medical Systems | Irrigation solution and method for inhibition of pain and inflammation |
| SE9600683D0 (sv) | 1996-02-23 | 1996-02-23 | Astra Ab | Azabicyclic esters of carbamic acids useful in therapy |
| DE19622353A1 (de) * | 1996-06-04 | 1997-12-11 | Bayer Ag | Substituierte Pyridine zur Bekämpfung tierischer Schädlinge |
| SI0912518T1 (en) | 1996-07-18 | 2003-12-31 | Merck Frosst Canada & Co. | Substituted pyridines as selective cyclooxygenase-2 inhibitors |
| KR100247563B1 (ko) | 1997-07-16 | 2000-04-01 | 박영구 | 키랄3,4-에폭시부티르산및이의염의제조방법 |
| US6277870B1 (en) | 1998-05-04 | 2001-08-21 | Astra Ab | Use |
| ATE255888T1 (de) | 1998-06-01 | 2003-12-15 | Ortho Mcneil Pharm Inc | Tetrahydronaphtalene verbindungen und deren verwendung zur behandlung von neurodegenerativen krankheiten |
| SE9900100D0 (sv) | 1999-01-15 | 1999-01-15 | Astra Ab | New compounds |
| FR2788982B1 (fr) | 1999-02-02 | 2002-08-02 | Synthelabo | Compositions pharmaceutiques contenant de la nicotine et leur application dans le sevrage tabagique |
| US6313110B1 (en) | 1999-06-02 | 2001-11-06 | Dupont Pharmaceuticals Company | Substituted 2H-1,3-diazapin-2-one useful as an HIV protease inhibitor |
| SE9903997D0 (sv) | 1999-11-03 | 1999-11-03 | Astra Ab | New compounds |
| SE9903998D0 (sv) | 1999-11-03 | 1999-11-03 | Astra Ab | New compounds |
| SE9904176D0 (sv) | 1999-11-18 | 1999-11-18 | Astra Ab | New use |
| EP1269201A1 (en) | 2000-03-29 | 2003-01-02 | Synaptica Limited | Alpha 7 nicotinic receptor screening assays |
| US6852741B2 (en) | 2001-12-31 | 2005-02-08 | University Of Florida | Compositions and methods for treatment of neurological disorders |
-
2003
- 2003-08-29 EP EP03791954A patent/EP1531820A1/en not_active Withdrawn
- 2003-08-29 EP EP10190760A patent/EP2298758A1/en not_active Withdrawn
- 2003-08-29 CA CA002495248A patent/CA2495248A1/en not_active Abandoned
- 2003-08-29 US US10/651,023 patent/US7244745B2/en not_active Expired - Fee Related
- 2003-08-29 WO PCT/US2003/027164 patent/WO2004019943A1/en not_active Ceased
- 2003-08-29 JP JP2004531954A patent/JP2006501246A/ja not_active Withdrawn
- 2003-08-29 AU AU2003265842A patent/AU2003265842A1/en not_active Abandoned
- 2003-08-29 EP EP10190764A patent/EP2305664A1/en not_active Withdrawn
- 2003-08-29 EP EP10190762A patent/EP2298759A1/en not_active Withdrawn
-
2007
- 2007-04-06 US US11/783,193 patent/US7700630B2/en not_active Expired - Fee Related
-
2010
- 2010-03-16 US US12/724,754 patent/US7994199B2/en not_active Expired - Fee Related
-
2011
- 2011-05-25 JP JP2011117305A patent/JP2011168617A/ja active Pending
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