JP2006505590A5 - - Google Patents
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- Publication number
- JP2006505590A5 JP2006505590A5 JP2004547134A JP2004547134A JP2006505590A5 JP 2006505590 A5 JP2006505590 A5 JP 2006505590A5 JP 2004547134 A JP2004547134 A JP 2004547134A JP 2004547134 A JP2004547134 A JP 2004547134A JP 2006505590 A5 JP2006505590 A5 JP 2006505590A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrrolidin
- piperidin
- ylmethylphenyl
- ylmethyl
- phenyl
- 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.)
- Withdrawn
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- 150000001875 compounds Chemical class 0.000 claims 69
- 125000000623 heterocyclic group Chemical group 0.000 claims 65
- 125000000217 alkyl group Chemical group 0.000 claims 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 43
- -1 alkenylene NR 1 Chemical compound 0.000 claims 41
- 125000001424 substituent group Chemical group 0.000 claims 30
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 23
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 claims 22
- 125000002947 alkylene group Chemical group 0.000 claims 21
- 125000003386 piperidinyl group Chemical group 0.000 claims 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 17
- 125000005843 halogen group Chemical group 0.000 claims 16
- 125000002757 morpholinyl group Chemical group 0.000 claims 15
- 229910052760 oxygen Inorganic materials 0.000 claims 14
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 14
- 229910052717 sulfur Inorganic materials 0.000 claims 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 12
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims 12
- 229910052799 carbon Inorganic materials 0.000 claims 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 11
- 125000004452 carbocyclyl group Chemical group 0.000 claims 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 10
- 229910052757 nitrogen Inorganic materials 0.000 claims 10
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 208000035475 disorder Diseases 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 102000005962 receptors Human genes 0.000 claims 9
- 108020003175 receptors Proteins 0.000 claims 9
- 125000003342 alkenyl group Chemical group 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 125000002883 imidazolyl group Chemical group 0.000 claims 7
- 125000004193 piperazinyl group Chemical group 0.000 claims 7
- 229920006395 saturated elastomer Polymers 0.000 claims 7
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 229960001340 histamine Drugs 0.000 claims 6
- 239000001301 oxygen Substances 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims 6
- 239000011593 sulfur Substances 0.000 claims 6
- 125000003831 tetrazolyl group Chemical group 0.000 claims 6
- 125000001425 triazolyl group Chemical group 0.000 claims 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 5
- PLVLVALRHKANNP-UHFFFAOYSA-N 1-[[1-[4-(pyrrolidin-1-ylmethyl)phenyl]piperidin-4-yl]methyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CC1CCN(C=2C=CC(CN3CCCC3)=CC=2)CC1 PLVLVALRHKANNP-UHFFFAOYSA-N 0.000 claims 5
- UZEVBQHLMNPEBL-UHFFFAOYSA-N 4-(piperidin-1-ylmethyl)-1-[4-(pyrrolidin-1-ylmethyl)phenyl]piperidine Chemical compound C1CCCCN1CC(CC1)CCN1C(C=C1)=CC=C1CN1CCCC1 UZEVBQHLMNPEBL-UHFFFAOYSA-N 0.000 claims 5
- RBVPQNARVICCEV-UHFFFAOYSA-N 4-(pyrrolidin-1-ylmethyl)-1-[4-(pyrrolidin-1-ylmethyl)phenyl]piperidine Chemical compound C1CCCN1CC(CC1)CCN1C(C=C1)=CC=C1CN1CCCC1 RBVPQNARVICCEV-UHFFFAOYSA-N 0.000 claims 5
- QTZIVPKCYKUXSW-UHFFFAOYSA-N 4-[2-[1-[4-(piperidin-1-ylmethyl)phenyl]pyrrolidin-3-yl]ethyl]morpholine Chemical compound C1CN(C=2C=CC(CN3CCCCC3)=CC=2)CC1CCN1CCOCC1 QTZIVPKCYKUXSW-UHFFFAOYSA-N 0.000 claims 5
- 125000002252 acyl group Chemical group 0.000 claims 5
- YNZIVJKQHARDRX-UHFFFAOYSA-N n,n-diethyl-2-[1-[4-(piperidin-1-ylmethyl)phenyl]pyrrolidin-3-yl]ethanamine Chemical compound C1C(CCN(CC)CC)CCN1C(C=C1)=CC=C1CN1CCCCC1 YNZIVJKQHARDRX-UHFFFAOYSA-N 0.000 claims 5
- FOILQRJGFNEQLP-UHFFFAOYSA-N n-[[1-[4-(pyrrolidin-1-ylmethyl)phenyl]piperidin-4-yl]methyl]cyclohexanamine Chemical compound C1CN(C=2C=CC(CN3CCCC3)=CC=2)CCC1CNC1CCCCC1 FOILQRJGFNEQLP-UHFFFAOYSA-N 0.000 claims 5
- QERMHLLQKWTBPS-UHFFFAOYSA-N n-ethyl-n-[[1-[4-(pyrrolidin-1-ylmethyl)phenyl]piperidin-4-yl]methyl]ethanamine Chemical compound C1CC(CN(CC)CC)CCN1C(C=C1)=CC=C1CN1CCCC1 QERMHLLQKWTBPS-UHFFFAOYSA-N 0.000 claims 5
- 125000004076 pyridyl group Chemical group 0.000 claims 5
- OTLAVTAGAGKZAJ-UHFFFAOYSA-N 1-[2-nitro-4-(pyrrolidin-1-ylmethyl)phenyl]-4-(pyrrolidin-1-ylmethyl)piperidine Chemical compound C=1C=C(N2CCC(CN3CCCC3)CC2)C([N+](=O)[O-])=CC=1CN1CCCC1 OTLAVTAGAGKZAJ-UHFFFAOYSA-N 0.000 claims 4
- TUUXVUCEFJGXOB-UHFFFAOYSA-N 1-[4-(piperidin-1-ylmethyl)phenyl]-4-(pyrrolidin-1-ylmethyl)piperidine Chemical compound C1CCCN1CC(CC1)CCN1C(C=C1)=CC=C1CN1CCCCC1 TUUXVUCEFJGXOB-UHFFFAOYSA-N 0.000 claims 4
- NXUKKSWSMXZVDG-UHFFFAOYSA-N 1-methyl-4-[[1-[4-(pyrrolidin-1-ylmethyl)phenyl]piperidin-4-yl]methyl]piperazine Chemical compound C1CN(C)CCN1CC1CCN(C=2C=CC(CN3CCCC3)=CC=2)CC1 NXUKKSWSMXZVDG-UHFFFAOYSA-N 0.000 claims 4
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims 4
- ZQGLMDGCVUWMNW-UHFFFAOYSA-N 4-[[1-[4-(pyrrolidin-1-ylmethyl)phenyl]piperidin-4-yl]methyl]morpholine Chemical compound C1COCCN1CC(CC1)CCN1C(C=C1)=CC=C1CN1CCCC1 ZQGLMDGCVUWMNW-UHFFFAOYSA-N 0.000 claims 4
- TVFCKYYEWGOTSJ-UHFFFAOYSA-N 4-[[1-[4-(pyrrolidin-1-ylmethyl)phenyl]piperidin-4-yl]methyl]thiomorpholine Chemical compound C1CSCCN1CC(CC1)CCN1C(C=C1)=CC=C1CN1CCCC1 TVFCKYYEWGOTSJ-UHFFFAOYSA-N 0.000 claims 4
- 206010012289 Dementia Diseases 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- GBIKJKYXQVWIKF-UHFFFAOYSA-N n,n-dimethyl-1-[1-[4-(pyrrolidin-1-ylmethyl)phenyl]piperidin-4-yl]methanamine Chemical compound C1CC(CN(C)C)CCN1C(C=C1)=CC=C1CN1CCCC1 GBIKJKYXQVWIKF-UHFFFAOYSA-N 0.000 claims 4
- WOLSYQJVYATUEL-UHFFFAOYSA-N n-[[4-[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]phenyl]methyl]cyclohexanamine Chemical compound C1CCCN1CC(CC1)CCN1C(C=C1)=CC=C1CNC1CCCCC1 WOLSYQJVYATUEL-UHFFFAOYSA-N 0.000 claims 4
- LBBDJKNFJMLOES-UHFFFAOYSA-N n-methyl-n-(2-phenylethyl)-2-[1-[4-(piperidin-1-ylmethyl)phenyl]pyrrolidin-3-yl]ethanamine Chemical compound C=1C=CC=CC=1CCN(C)CCC(C1)CCN1C(C=C1)=CC=C1CN1CCCCC1 LBBDJKNFJMLOES-UHFFFAOYSA-N 0.000 claims 4
- 230000001225 therapeutic effect Effects 0.000 claims 4
- HOTIEXVMRGMORX-UHFFFAOYSA-N 1-[2-methyl-4-(pyrrolidin-1-ylmethyl)phenyl]-3-(pyrrolidin-1-ylmethyl)pyrrolidine Chemical compound C=1C=C(N2CC(CN3CCCC3)CC2)C(C)=CC=1CN1CCCC1 HOTIEXVMRGMORX-UHFFFAOYSA-N 0.000 claims 3
- KLXKXHICVHEMEB-UHFFFAOYSA-N 1-[3-fluoro-4-[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]phenyl]-n,n-dimethylmethanamine Chemical compound FC1=CC(CN(C)C)=CC=C1N1CCC(CN2CCCC2)CC1 KLXKXHICVHEMEB-UHFFFAOYSA-N 0.000 claims 3
- SBACPJOFFKRFLY-UHFFFAOYSA-N 1-[[3-nitro-4-[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]phenyl]methyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CC(C=C1[N+]([O-])=O)=CC=C1N1CCC(CN2CCCC2)CC1 SBACPJOFFKRFLY-UHFFFAOYSA-N 0.000 claims 3
- PABBGGVSULEGAG-UHFFFAOYSA-N 1-[[4-[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]phenyl]methyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CC1=CC=C(N2CCC(CN3CCCC3)CC2)C=C1 PABBGGVSULEGAG-UHFFFAOYSA-N 0.000 claims 3
- RZRWYYDNMDQWLH-UHFFFAOYSA-N 4-(piperidin-1-ylmethyl)-1-[4-(piperidin-1-ylmethyl)phenyl]piperidine Chemical compound C1CCCCN1CC(CC1)CCN1C(C=C1)=CC=C1CN1CCCCC1 RZRWYYDNMDQWLH-UHFFFAOYSA-N 0.000 claims 3
- HAFNMJJPFDHELH-UHFFFAOYSA-N 4-[[1-[4-(piperidin-1-ylmethyl)phenyl]piperidin-4-yl]methyl]morpholine Chemical compound C1COCCN1CC(CC1)CCN1C(C=C1)=CC=C1CN1CCCCC1 HAFNMJJPFDHELH-UHFFFAOYSA-N 0.000 claims 3
- DRBCWDITQPAELE-UHFFFAOYSA-N 4-[[4-[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]phenyl]methyl]thiomorpholine Chemical compound C1CCCN1CC(CC1)CCN1C(C=C1)=CC=C1CN1CCSCC1 DRBCWDITQPAELE-UHFFFAOYSA-N 0.000 claims 3
- WRGJNDFQGMHERH-UHFFFAOYSA-N 4-piperidin-1-yl-1-[4-(piperidin-1-ylmethyl)phenyl]piperidine Chemical group C=1C=C(N2CCC(CC2)N2CCCCC2)C=CC=1CN1CCCCC1 WRGJNDFQGMHERH-UHFFFAOYSA-N 0.000 claims 3
- ZSBDQOWXWWDUCG-UHFFFAOYSA-N N-amino-N-carbonocyanidoylnitramide Chemical compound [O-][N+](=O)N(N)C(=O)C#N ZSBDQOWXWWDUCG-UHFFFAOYSA-N 0.000 claims 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 3
- 208000010877 cognitive disease Diseases 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 125000002541 furyl group Chemical group 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- CFNVVWNKWBOFRI-UHFFFAOYSA-N n,n-dimethyl-1-[4-[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]phenyl]methanamine Chemical compound C1=CC(CN(C)C)=CC=C1N1CCC(CN2CCCC2)CC1 CFNVVWNKWBOFRI-UHFFFAOYSA-N 0.000 claims 3
- ZPPVOSUTPPAQIX-UHFFFAOYSA-N n-[[1-[4-(pyrrolidin-1-ylmethyl)phenyl]piperidin-4-yl]methyl]pyridin-2-amine Chemical compound C1CN(C=2C=CC(CN3CCCC3)=CC=2)CCC1CNC1=CC=CC=N1 ZPPVOSUTPPAQIX-UHFFFAOYSA-N 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 125000002971 oxazolyl group Chemical group 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 125000001422 pyrrolinyl group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims 2
- QNSRHBOZQLXYNV-UHFFFAOYSA-N 1,4,7-trioxa-10-azacyclododecane Chemical compound C1COCCOCCOCCN1 QNSRHBOZQLXYNV-UHFFFAOYSA-N 0.000 claims 2
- MRBFGEHILMYPTF-UHFFFAOYSA-N 1-(2-Pyrimidyl)piperazine Chemical compound C1CNCCN1C1=NC=CC=N1 MRBFGEHILMYPTF-UHFFFAOYSA-N 0.000 claims 2
- KKIMDKMETPPURN-UHFFFAOYSA-N 1-(3-(trifluoromethyl)phenyl)piperazine Chemical compound FC(F)(F)C1=CC=CC(N2CCNCC2)=C1 KKIMDKMETPPURN-UHFFFAOYSA-N 0.000 claims 2
- DTWUNJHTJDNWIE-UHFFFAOYSA-N 1-[2-fluoro-4-[(4-phenylpiperidin-1-yl)methyl]phenyl]-4-(pyrrolidin-1-ylmethyl)piperidine Chemical compound C=1C=C(N2CCC(CN3CCCC3)CC2)C(F)=CC=1CN(CC1)CCC1C1=CC=CC=C1 DTWUNJHTJDNWIE-UHFFFAOYSA-N 0.000 claims 2
- MFUADFONPBYSJK-UHFFFAOYSA-N 1-[3-(piperidin-1-ylmethyl)phenyl]-4-(pyrrolidin-1-ylmethyl)piperidine Chemical compound C1CCCN1CC(CC1)CCN1C(C=1)=CC=CC=1CN1CCCCC1 MFUADFONPBYSJK-UHFFFAOYSA-N 0.000 claims 2
- QRVYLRQQLDMXSJ-UHFFFAOYSA-N 1-[[4-[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]phenyl]methyl]-azacyclotridecane Chemical compound C1CCCN1CC(CC1)CCN1C(C=C1)=CC=C1CN1CCCCCCCCCCCC1 QRVYLRQQLDMXSJ-UHFFFAOYSA-N 0.000 claims 2
- OFUFIDWGBOOQHU-UHFFFAOYSA-N 1-methyl-4-[[4-[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]phenyl]methyl]piperazine Chemical compound C1CN(C)CCN1CC1=CC=C(N2CCC(CN3CCCC3)CC2)C=C1 OFUFIDWGBOOQHU-UHFFFAOYSA-N 0.000 claims 2
- HTQWGIHCFPWKAS-UHFFFAOYSA-N 1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound C1CNCCC11C(=O)NCN1C1=CC=CC=C1 HTQWGIHCFPWKAS-UHFFFAOYSA-N 0.000 claims 2
- HNJWKRMESUMDQE-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-methylethanamine Chemical compound CNCCC1=CC=C(OC)C(OC)=C1 HNJWKRMESUMDQE-UHFFFAOYSA-N 0.000 claims 2
- FVDOFIVSQBSGBG-UHFFFAOYSA-N 4-(pyrrolidin-1-ylmethyl)-1-[3-(pyrrolidin-1-ylmethyl)phenyl]piperidine Chemical compound C1CCCN1CC(CC1)CCN1C(C=1)=CC=CC=1CN1CCCC1 FVDOFIVSQBSGBG-UHFFFAOYSA-N 0.000 claims 2
- IFMBHNNPGHQVGS-UHFFFAOYSA-N 4-[[3-[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]phenyl]methyl]thiomorpholine Chemical compound C1CCCN1CC(CC1)CCN1C(C=1)=CC=CC=1CN1CCSCC1 IFMBHNNPGHQVGS-UHFFFAOYSA-N 0.000 claims 2
- WSLSJAMMMLIRTL-UHFFFAOYSA-N 4-[[4-(4-piperidin-1-ylpiperidin-1-yl)phenyl]methyl]morpholine Chemical group C=1C=C(N2CCC(CC2)N2CCCCC2)C=CC=1CN1CCOCC1 WSLSJAMMMLIRTL-UHFFFAOYSA-N 0.000 claims 2
- KRJPTXSGPDNFAX-UHFFFAOYSA-N 4-pyrrolidin-1-yl-1-[[4-[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]-3-(trifluoromethyl)phenyl]methyl]piperidine Chemical compound C=1C=C(N2CCC(CN3CCCC3)CC2)C(C(F)(F)F)=CC=1CN(CC1)CCC1N1CCCC1 KRJPTXSGPDNFAX-UHFFFAOYSA-N 0.000 claims 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 208000020358 Learning disease Diseases 0.000 claims 2
- 206010028735 Nasal congestion Diseases 0.000 claims 2
- 206010039085 Rhinitis allergic Diseases 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000001118 alkylidene group Chemical group 0.000 claims 2
- 125000004419 alkynylene group Chemical group 0.000 claims 2
- 208000026935 allergic disease Diseases 0.000 claims 2
- 201000010105 allergic rhinitis Diseases 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 230000037007 arousal Effects 0.000 claims 2
- 125000005110 aryl thio group Chemical group 0.000 claims 2
- 125000004069 aziridinyl group Chemical group 0.000 claims 2
- UUQMNUMQCIQDMZ-UHFFFAOYSA-N betahistine Chemical compound CNCCC1=CC=CC=N1 UUQMNUMQCIQDMZ-UHFFFAOYSA-N 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 150000003857 carboxamides Chemical class 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 239000002552 dosage form Substances 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 239000000938 histamine H1 antagonist Substances 0.000 claims 2
- 239000003485 histamine H2 receptor antagonist Substances 0.000 claims 2
- 201000003723 learning disability Diseases 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 208000027061 mild cognitive impairment Diseases 0.000 claims 2
- VGHDJHADNFTDFL-UHFFFAOYSA-N n-[[1-[4-(pyrrolidin-1-ylmethyl)phenyl]piperidin-4-yl]methyl]aniline Chemical compound C1CN(C=2C=CC(CN3CCCC3)=CC=2)CCC1CNC1=CC=CC=C1 VGHDJHADNFTDFL-UHFFFAOYSA-N 0.000 claims 2
- QYWNDCJNJYXYNE-UHFFFAOYSA-N n-cyclohexyl-n-methyl-1-[4-(morpholin-4-ylmethyl)phenyl]piperidin-4-amine Chemical compound C1CN(C=2C=CC(CN3CCOCC3)=CC=2)CCC1N(C)C1CCCCC1 QYWNDCJNJYXYNE-UHFFFAOYSA-N 0.000 claims 2
- SBSLCPHONZWKIE-UHFFFAOYSA-N n-piperidin-4-ylpyridin-2-amine Chemical compound C1CNCCC1NC1=CC=CC=N1 SBSLCPHONZWKIE-UHFFFAOYSA-N 0.000 claims 2
- CTSIKBGUCQWRIM-UHFFFAOYSA-N n-prop-2-enylcyclopentanamine Chemical compound C=CCNC1CCCC1 CTSIKBGUCQWRIM-UHFFFAOYSA-N 0.000 claims 2
- 201000003631 narcolepsy Diseases 0.000 claims 2
- 238000002600 positron emission tomography Methods 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- YSHVOKPFFKOFSH-UHFFFAOYSA-N 1-(6-oxocyclohexa-2,4-dien-1-yl)-2-phenylethane-1,2-dione Chemical group O=C1C(C=CC=C1)C(C(C1=CC=CC=C1)=O)=O YSHVOKPFFKOFSH-UHFFFAOYSA-N 0.000 claims 1
- VHECJYWGTIVAFE-UHFFFAOYSA-N 1-[2-fluoro-4-(piperidin-1-ylmethyl)phenyl]-4-(pyrrolidin-1-ylmethyl)piperidine Chemical compound C=1C=C(N2CCC(CN3CCCC3)CC2)C(F)=CC=1CN1CCCCC1 VHECJYWGTIVAFE-UHFFFAOYSA-N 0.000 claims 1
- PFLMHMTVUVACKY-UHFFFAOYSA-N 1-[2-methyl-4-(pyrrolidin-1-ylmethyl)phenyl]-4-(pyrrolidin-1-ylmethyl)piperidine Chemical compound C=1C=C(N2CCC(CN3CCCC3)CC2)C(C)=CC=1CN1CCCC1 PFLMHMTVUVACKY-UHFFFAOYSA-N 0.000 claims 1
- QSCIOFFZDYWYJP-UHFFFAOYSA-N 1-[4-(piperidin-1-ylmethyl)-2-(trifluoromethyl)phenyl]-4-(pyrrolidin-1-ylmethyl)piperidine Chemical compound C=1C=C(N2CCC(CN3CCCC3)CC2)C(C(F)(F)F)=CC=1CN1CCCCC1 QSCIOFFZDYWYJP-UHFFFAOYSA-N 0.000 claims 1
- YNHDRGOVQXRBIM-UHFFFAOYSA-N 1-[4-(piperidin-1-ylmethyl)-3-(trifluoromethyl)phenyl]-4-(pyrrolidin-1-ylmethyl)piperidine Chemical compound FC(F)(F)C1=CC(N2CCC(CN3CCCC3)CC2)=CC=C1CN1CCCCC1 YNHDRGOVQXRBIM-UHFFFAOYSA-N 0.000 claims 1
- TXQJICMVDLSSHG-UHFFFAOYSA-N 1-[[1-[4-(pyrrolidin-1-ylmethyl)phenyl]piperidin-4-yl]methyl]-azacyclotridecane Chemical compound C1CCCCCCCCCCCN1CC(CC1)CCN1C(C=C1)=CC=C1CN1CCCC1 TXQJICMVDLSSHG-UHFFFAOYSA-N 0.000 claims 1
- KDTOUPSXMARKSX-UHFFFAOYSA-N 1-[[3-methyl-4-[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]phenyl]methyl]-4-propan-2-ylpiperazine Chemical compound C1CN(C(C)C)CCN1CC(C=C1C)=CC=C1N1CCC(CN2CCCC2)CC1 KDTOUPSXMARKSX-UHFFFAOYSA-N 0.000 claims 1
- DLLVKVXWXCQRDR-UHFFFAOYSA-N 1-[[4-[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]-2-(trifluoromethyl)phenyl]methyl]-4-[4-(trifluoromethyl)phenyl]piperidine Chemical compound C1=CC(C(F)(F)F)=CC=C1C1CCN(CC=2C(=CC(=CC=2)N2CCC(CN3CCCC3)CC2)C(F)(F)F)CC1 DLLVKVXWXCQRDR-UHFFFAOYSA-N 0.000 claims 1
- IAFUZCLDORRBJY-UHFFFAOYSA-N 2-piperidin-4-yloxypyrimidine Chemical compound C1CNCCC1OC1=NC=CC=N1 IAFUZCLDORRBJY-UHFFFAOYSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
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- YDNBOQKWNWPBCE-UHFFFAOYSA-N 4-[[2-[4-(piperidin-1-ylmethyl)piperidin-1-yl]phenyl]methyl]morpholine Chemical compound C1CCCCN1CC(CC1)CCN1C1=CC=CC=C1CN1CCOCC1 YDNBOQKWNWPBCE-UHFFFAOYSA-N 0.000 claims 1
- QBXIFOODEPYGPV-UHFFFAOYSA-N 4-[[2-[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]phenyl]methyl]morpholine Chemical compound C1CCCN1CC(CC1)CCN1C1=CC=CC=C1CN1CCOCC1 QBXIFOODEPYGPV-UHFFFAOYSA-N 0.000 claims 1
- HIPKKOLMDLDNTG-UHFFFAOYSA-N 4-[[3-[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]phenyl]methyl]morpholine Chemical compound C1CCCN1CC(CC1)CCN1C(C=1)=CC=CC=1CN1CCOCC1 HIPKKOLMDLDNTG-UHFFFAOYSA-N 0.000 claims 1
- ORRDDIYRKNUJMG-UHFFFAOYSA-N 4-[[3-nitro-4-[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]phenyl]methyl]morpholine Chemical compound C=1C=C(N2CCC(CN3CCCC3)CC2)C([N+](=O)[O-])=CC=1CN1CCOCC1 ORRDDIYRKNUJMG-UHFFFAOYSA-N 0.000 claims 1
- LVQPYDDLKXXOLP-UHFFFAOYSA-N 4-[[4-(4-pyrrolidin-1-ylpiperidin-1-yl)phenyl]methyl]morpholine Chemical compound C=1C=C(N2CCC(CC2)N2CCCC2)C=CC=1CN1CCOCC1 LVQPYDDLKXXOLP-UHFFFAOYSA-N 0.000 claims 1
- QZWWWVGMWSIXOK-UHFFFAOYSA-N 4-[[4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl]methyl]morpholine Chemical compound C1CN(C)CCN1C1CCN(C=2C=CC(CN3CCOCC3)=CC=2)CC1 QZWWWVGMWSIXOK-UHFFFAOYSA-N 0.000 claims 1
- YGOOQHALGSJELC-UHFFFAOYSA-N 4-[[4-[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]phenyl]methyl]morpholine Chemical compound C1CCCN1CC(CC1)CCN1C(C=C1)=CC=C1CN1CCOCC1 YGOOQHALGSJELC-UHFFFAOYSA-N 0.000 claims 1
- GJQCDNVDDCGWQO-UHFFFAOYSA-N 4-fluoro-n-[[4-[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]phenyl]methyl]aniline Chemical compound C1=CC(F)=CC=C1NCC1=CC=C(N2CCC(CN3CCCC3)CC2)C=C1 GJQCDNVDDCGWQO-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
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- 208000019695 Migraine disease Diseases 0.000 claims 1
- NCIKQJBVUNUXLW-UHFFFAOYSA-N N-methyltryptamine Chemical compound C1=CC=C2C(CCNC)=CNC2=C1 NCIKQJBVUNUXLW-UHFFFAOYSA-N 0.000 claims 1
- 206010062519 Poor quality sleep Diseases 0.000 claims 1
- 206010041349 Somnolence Diseases 0.000 claims 1
- SLMBFZLCHGHKEQ-UHFFFAOYSA-N [1-[[4-[4-(pyrrolidin-1-ylmethyl)piperidin-1-yl]-3-(trifluoromethyl)phenyl]methyl]piperidin-4-yl]methanol Chemical compound C1CC(CO)CCN1CC(C=C1C(F)(F)F)=CC=C1N1CCC(CN2CCCC2)CC1 SLMBFZLCHGHKEQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004450 alkenylene group Chemical group 0.000 claims 1
- MTXSIJUGVMTTMU-UHFFFAOYSA-N anabasine Chemical group N1CCCCC1C1=CC=CN=C1 MTXSIJUGVMTTMU-UHFFFAOYSA-N 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000005518 carboxamido group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 230000006735 deficit Effects 0.000 claims 1
- 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 claims 1
- 235000014632 disordered eating Nutrition 0.000 claims 1
- 208000002173 dizziness Diseases 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 208000013403 hyperactivity Diseases 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 230000014759 maintenance of location Effects 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 239000003068 molecular probe Substances 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 201000003152 motion sickness Diseases 0.000 claims 1
- ZXQKYQVJDRTTLZ-UHFFFAOYSA-N n,n-diethylpiperidine-3-carboxamide Chemical compound CCN(CC)C(=O)C1CCCNC1 ZXQKYQVJDRTTLZ-UHFFFAOYSA-N 0.000 claims 1
- RPXHDXWBRSHQAM-UHFFFAOYSA-N n-cyclohexyl-1-[4-(morpholin-4-ylmethyl)phenyl]piperidin-4-amine Chemical compound C=1C=C(N2CCC(CC2)NC2CCCCC2)C=CC=1CN1CCOCC1 RPXHDXWBRSHQAM-UHFFFAOYSA-N 0.000 claims 1
- HLBDXSMVHZHKFF-UHFFFAOYSA-N n-ethyl-n-methyl-1-[4-(morpholin-4-ylmethyl)phenyl]piperidin-4-amine Chemical compound C1CC(N(C)CC)CCN1C(C=C1)=CC=C1CN1CCOCC1 HLBDXSMVHZHKFF-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 230000000069 prophylactic effect Effects 0.000 claims 1
- 238000002603 single-photon emission computed tomography Methods 0.000 claims 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 1
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| US42049402P | 2002-10-23 | 2002-10-23 | |
| PCT/US2003/033809 WO2004037257A1 (en) | 2002-10-23 | 2003-10-23 | Phenylpiperidines and phenylpyrrolidines as histamine h3 receptor modulators |
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| JP2006505590A JP2006505590A (ja) | 2006-02-16 |
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| US7547693B2 (en) | 2003-09-22 | 2009-06-16 | Banyu Pharmaceutical Co. Ltd. | Piperidine derivative |
| ES2303280T3 (es) * | 2004-10-15 | 2008-08-01 | Glaxo Group Limited | Derivados de pirrolidina como ligandos de receptores de histamina. |
| GB0611907D0 (en) * | 2006-06-15 | 2006-07-26 | Glaxo Group Ltd | Compounds |
| EP1707203A1 (en) * | 2005-04-01 | 2006-10-04 | Bioprojet | Treatment of parkinson's disease obstructive sleep apnea, dementia with lewy bodies, vascular dementia with non-imidazole alkylamines histamine H3- receptor ligands |
| KR101397913B1 (ko) * | 2005-05-30 | 2014-05-26 | 엠에스디 가부시키가이샤 | 신규 피페리딘 유도체 |
| CN101228127B (zh) * | 2005-05-30 | 2012-05-16 | Msdk.K.公司 | 哌啶衍生物 |
| US7553964B2 (en) * | 2005-06-03 | 2009-06-30 | Abbott Laboratories | Cyclobutyl amine derivatives |
| AU2006265997B2 (en) * | 2005-07-01 | 2011-11-17 | Eli Lilly And Company | Histamine H3 receptor agents, preparation and therapeutic uses |
| WO2007007018A1 (en) * | 2005-07-12 | 2007-01-18 | Glaxo Group Limited | Piperazine heteroaryl derivates as gpr38 agonists |
| ES2372332T3 (es) * | 2007-10-17 | 2012-01-18 | Sanofi | N-fenil-bipirrolidina carboxamidas sustituidas y su uso terapéutico. |
| HRP20110953T1 (hr) * | 2007-10-17 | 2012-01-31 | Sanofi | Supstituirani n-fenilbipirolidinkarboksamidi i njihova upotreba u terapiji |
| KR20100092443A (ko) * | 2007-10-17 | 2010-08-20 | 사노피-아벤티스 | 치환된 ｎ-페닐-피롤리디닐메틸피롤리딘 아미드 및 히스타민 ｈ3 수용체 조절제로서의 이의 치료적 용도 |
| DK2215058T3 (da) | 2007-10-17 | 2012-03-12 | Sanofi Sa | Substituerede N-phenylbipyrrolidinureaer og terapeutisk anvendelse deraf |
| AR074466A1 (es) | 2008-12-05 | 2011-01-19 | Sanofi Aventis | Piperidina espiro pirrolidinona y piperidinona sustituidas y su uso terapeutico en enfermedades mediadas por la modulacion de los receptores h3. |
| AR074467A1 (es) * | 2008-12-05 | 2011-01-19 | Sanofi Aventis | Tetrahidropiran espiro pirrolidinonas y piperidinonas sustituidas, composiciones farmaceuticas que las contienen y uso de las mismas en el tratamiento y/o prevencion de enfermedades del snc ,tales como alzheimer y parkinson, entre otras. |
| TW201206901A (en) | 2010-05-11 | 2012-02-16 | Sanofi Aventis | Substituted N-heteroaryl bipyrrolidine carboxamides, preparation and therapeutic use thereof |
| AR083718A1 (es) * | 2010-05-11 | 2013-03-20 | Sanofi Aventis | Fenil cicloalquil pirrolidina (piperidina) espirolactamas y amidas sustituidas, preparacion y uso terapeutico de las mismas |
| WO2011143148A1 (en) | 2010-05-11 | 2011-11-17 | Sanofi | Substituted n-heteroaryl spirolactam bipyrrolidines, preparation and therapeutic use thereof |
| TW201206889A (en) | 2010-05-11 | 2012-02-16 | Sanofi Aventis | Substituted N-alkyl and N-acyl tetrahydro-isoquinoline derivatives, preparation and therapeutic use thereof |
| TW201206910A (en) | 2010-05-11 | 2012-02-16 | Sanofi Aventis | Substituted N-heterocycloalkyl bipyrrolidinylphenyl amide derivatives, preparation and therapeutic use thereof |
| AR081034A1 (es) | 2010-05-11 | 2012-05-30 | Sanofi Aventis | Derivados de n-heteroaril tetrahidro-isoquinolina sustituidos, composiciones farmaceuticas que los contienen y uso de los mismos para el tratamiento de enfermedades del sistema nervioso central |
| JP6364568B1 (ja) * | 2018-03-19 | 2018-07-25 | 株式会社片岡商店 | 工場内安全標識投影装置 |
| AU2019387370A1 (en) | 2018-11-30 | 2021-06-10 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
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| US3714179A (en) | 1970-09-08 | 1973-01-30 | Searle & Co | 1-alkyl-2-furfurylthioimidazoles and congeners |
| US3886160A (en) | 1972-09-28 | 1975-05-27 | Searle & Co | 2-(2-Methyl-5-nitro-1-imidazolyl) ethyl-2-thiopseudoureas |
| JPS61501205A (ja) * | 1984-02-15 | 1986-06-19 | シェリング・コ−ポレ−ション | ８↓−クロル↓−６，１１↓−ジヒドロ↓−１１↓−（４↓−ピペリジリデン）↓−５Ｈ↓−ベンゾ〔５，６〕シクロヘプタ〔１，２−ｂ〕ピリジンおよびその塩、これらの化合物の製造方法、ならびにこれらの化合物を含有する医薬組成物 |
| JP2813747B2 (ja) | 1989-05-22 | 1998-10-22 | 富士写真フイルム株式会社 | 画像形成法 |
| US5030644A (en) | 1989-07-31 | 1991-07-09 | Merck & Co., Inc. | Imidazole compounds and their use as transglutaminase inhibitors |
| US5217986A (en) | 1992-03-26 | 1993-06-08 | Harbor Branch Oceanographic Institution, Inc. | Anti-allergy agent |
| US5352707A (en) | 1992-03-26 | 1994-10-04 | Harbor Branch Oceanographic Institution, Inc. | Method for treating airway congestion |
| US5869479A (en) | 1997-08-14 | 1999-02-09 | Schering Corporation | Treatment of upper airway allergic responses |
| GB9803536D0 (en) | 1998-02-19 | 1998-04-15 | Black James Foundation | Histamine H,receptor ligands |
| WO1999052872A1 (en) * | 1998-04-09 | 1999-10-21 | Meiji Seika Kaisha, Ltd. | AMINOPIPERIDINE DERIVATIVES AS INTEGRIN αvβ3 ANTAGONISTS |
| EP0952154B1 (en) | 1998-04-16 | 2004-08-18 | Pfizer Products Inc. | N-acyl and N-aroyl aralkyl amides |
| EP0978512A1 (en) | 1998-07-29 | 2000-02-09 | Societe Civile Bioprojet | Non-imidazole aryloxy (or arylthio) alkylamines as histamine H3-receptor antagonists and their therapeutic applications |
| BRPI0113162B8 (pt) | 2000-08-08 | 2021-05-25 | Johnson & Johnson | compostos ariloxialquilaminas nao-imidazólicos e composição farmacêutica compreendendo os referidos compostos |
| MXPA03001268A (es) | 2000-08-08 | 2004-09-06 | Johnson & Johnson | Ariloxipiperidinas sin imidazol. |
| EP1326863A2 (en) | 2000-09-22 | 2003-07-16 | Ortho-McNeil Pharmaceutical, Inc. | Octahydro-indolizines and quinolizines and hexahydro-pyrrolizines |
| CA2441080A1 (en) | 2001-03-23 | 2002-10-03 | Eli Lilly And Company | Non-imidazole aryl alkylamines compounds as histamine h3 receptor antagonists, preparation and therapeutic uses |
| TW200302225A (en) * | 2001-12-04 | 2003-08-01 | Bristol Myers Squibb Co | Substituted amino methyl factor Xa inhibitors |
| JP2005511740A (ja) | 2001-12-10 | 2005-04-28 | オーソ−マクニール・フアーマシユーチカル・インコーポレーテツド | フェニルアルキン |
| ATE430727T1 (de) | 2001-12-20 | 2009-05-15 | Bristol Myers Squibb Co | Alpha-(n-sulfonamid)acetamidderivate als beta- amyloidinhibitoren |
| AU2003203148A1 (en) | 2002-02-05 | 2003-09-02 | High Point Pharmaceuticals, Llc | Novel aryl- and heteroarylpiperazines |
| US20050222408A1 (en) * | 2003-07-14 | 2005-10-06 | University Of Tennessee Research Foundation | Heterocyclic amides with anti-tuberculosis activity |
-
2003
- 2003-10-23 CA CA002504272A patent/CA2504272A1/en not_active Abandoned
- 2003-10-23 AU AU2003287206A patent/AU2003287206A1/en not_active Abandoned
- 2003-10-23 EP EP03781386A patent/EP1556046A1/en not_active Withdrawn
- 2003-10-23 WO PCT/US2003/033809 patent/WO2004037257A1/en not_active Ceased
- 2003-10-23 US US10/692,080 patent/US7279491B2/en not_active Expired - Lifetime
- 2003-10-23 JP JP2004547134A patent/JP2006505590A/ja not_active Withdrawn
-
2007
- 2007-08-08 US US11/835,880 patent/US20080004314A1/en not_active Abandoned
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