JP2006505590A5 - - Google Patents
Download PDFInfo
- 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- Withdrawn
Links
- 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
- BYNBAMHAURJNTR-UHFFFAOYSA-N 3-piperidin-4-yl-1h-benzimidazol-2-one Chemical compound O=C1NC2=CC=CC=C2N1C1CCNCC1 BYNBAMHAURJNTR-UHFFFAOYSA-N 0.000 claims 1
- DPBWFNDFMCCGGJ-UHFFFAOYSA-N 4-Piperidine carboxamide Chemical compound NC(=O)C1CCNCC1 DPBWFNDFMCCGGJ-UHFFFAOYSA-N 0.000 claims 1
- IKLCBIKUEYBDJM-UHFFFAOYSA-N 4-[1-[4-(morpholin-4-ylmethyl)phenyl]piperidin-4-yl]morpholine Chemical compound C=1C=C(N2CCC(CC2)N2CCOCC2)C=CC=1CN1CCOCC1 IKLCBIKUEYBDJM-UHFFFAOYSA-N 0.000 claims 1
- 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
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 208000030814 Eating disease Diseases 0.000 claims 1
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- 206010026749 Mania Diseases 0.000 claims 1
- 208000026139 Memory disease Diseases 0.000 claims 1
- 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
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006505590A JP2006505590A (ja) | 2006-02-16 |
| JP2006505590A5 true JP2006505590A5 (https=) | 2006-11-24 |
Family
ID=32176578
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004547134A Withdrawn JP2006505590A (ja) | 2002-10-23 | 2003-10-23 | ヒスタミンｈ３受容体調節物質としてのフェニルピペリジンおよびフェニルピロリジン |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US7279491B2 (https=) |
| EP (1) | EP1556046A1 (https=) |
| JP (1) | JP2006505590A (https=) |
| AU (1) | AU2003287206A1 (https=) |
| CA (1) | CA2504272A1 (https=) |
| WO (1) | WO2004037257A1 (https=) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2004274309B2 (en) | 2003-09-22 | 2010-04-08 | Msd K.K. | Novel piperidine derivative |
| EP1802307B1 (en) * | 2004-10-15 | 2008-02-27 | Glaxo Group Limited | Pyrrolidine derivatives as histamine receptors ligands |
| 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 |
| CN101228127B (zh) * | 2005-05-30 | 2012-05-16 | Msdk.K.公司 | 哌啶衍生物 |
| CA2609388C (en) * | 2005-05-30 | 2013-08-06 | Banyu Pharmaceutical Co., Ltd. | Novel piperidine derivative |
| US7553964B2 (en) * | 2005-06-03 | 2009-06-30 | Abbott Laboratories | Cyclobutyl amine derivatives |
| EP1904442B1 (en) * | 2005-07-01 | 2011-09-07 | Eli Lilly And Company | Histamine h3 receptor agents, preparation and therapeutic uses |
| JP2009501199A (ja) * | 2005-07-12 | 2009-01-15 | グラクソ グループ リミテッド | Ｇｐｒ３８アゴニストとしてのピペラジンヘテロアリール誘導体 |
| EP2212282B1 (en) * | 2007-10-17 | 2011-09-21 | Sanofi | Substituted n-phenyl-bipyrrolidine carboxamides and therapeutic use thereof |
| WO2009052068A1 (en) * | 2007-10-17 | 2009-04-23 | Sanofi-Aventis | Substituted n-phenyl-bipyrrolidine ureas and therapeutic use thereof |
| CN101903340B (zh) | 2007-10-17 | 2013-03-27 | 赛诺菲-安万特 | 取代的n-苯基联吡咯烷羧酰胺及其治疗用途 |
| CN101903342B (zh) * | 2007-10-17 | 2012-11-21 | 赛诺菲-安万特 | 取代的n-苯基-吡咯烷基甲基吡咯烷酰胺及其作为组胺h3受体调节剂的治疗用途 |
| 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. |
| 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. |
| WO2011143155A1 (en) * | 2010-05-11 | 2011-11-17 | Sanofi | Substituted n-heteroaryl tetrahydro-isoquinoline derivatives, preparation and therapeutic use thereof |
| JP5833105B2 (ja) | 2010-05-11 | 2015-12-16 | サノフイ | 置換ｎ−ヘテロアリールスピロラクタムビピロリジン類、その製造及び治療的使用 |
| 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 |
| TW201206889A (en) | 2010-05-11 | 2012-02-16 | Sanofi Aventis | Substituted N-alkyl and N-acyl tetrahydro-isoquinoline derivatives, preparation and therapeutic use thereof |
| WO2011143162A1 (en) | 2010-05-11 | 2011-11-17 | Sanofi | Substituted n-heteroaryl bipyrrolidine carboxamides, preparation and therapeutic use thereof |
| EP2569297A1 (en) | 2010-05-11 | 2013-03-20 | Sanofi | Substituted n-heterocycloalkyl bipyrrolidinylphenyl amide derivatives, preparation and therapeutic use thereof |
| 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 |
| WO2020113094A1 (en) | 2018-11-30 | 2020-06-04 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| WO1985003707A1 (en) * | 1984-02-15 | 1985-08-29 | Schering Corporation | 8-CHLORO-6,11-DIHYDRO-11-(4-PIPERIDYLIDENE)-5H-BENZO AD5,6 BDCYCLOHEPTA AD1,2-b BDPYRIDINE AND ITS SALTS, PROCESSES FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING THESE COMPOUNDS |
| 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 |
| US5352707A (en) | 1992-03-26 | 1994-10-04 | Harbor Branch Oceanographic Institution, Inc. | Method for treating airway congestion |
| US5217986A (en) | 1992-03-26 | 1993-06-08 | Harbor Branch Oceanographic Institution, Inc. | Anti-allergy agent |
| 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 |
| ATE542797T1 (de) | 1998-04-09 | 2012-02-15 | Meiji Seika Pharma Co Ltd | Aminopiperidinderivate als integrin alpha v beta 3 antagonisten |
| ES2226284T3 (es) * | 1998-04-16 | 2005-03-16 | Pfizer Products Inc. | N-acil y n-aroil-aralquilamidas. |
| 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 |
| ATE319696T1 (de) * | 2000-08-08 | 2006-03-15 | Ortho Mcneil Pharm Inc | Nicht-imidazol aryloxyalkylamine als h3 rezeptor liganden |
| CZ2003686A3 (cs) | 2000-08-08 | 2003-08-13 | Ortho Mcneil Pharmaceutical, Inc. | Neimidazolové aryloxypiperidiny |
| JP2004510712A (ja) | 2000-09-22 | 2004-04-08 | 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 | オクタヒドロ−インドリジンおよびキノリジンおよびヘキサヒドロ−ピロリジン |
| JP2004532834A (ja) * | 2001-03-23 | 2004-10-28 | イーライ・リリー・アンド・カンパニー | ヒスタミンｈ３受容体アンタゴニストである非イミダゾール系アリールアルキルアミン化合物、その製造および治療的使用 |
| TW200302225A (en) * | 2001-12-04 | 2003-08-01 | Bristol Myers Squibb Co | Substituted amino methyl factor Xa inhibitors |
| PT1451167E (pt) | 2001-12-10 | 2006-07-31 | Ortho Mcneil Pharm Inc | Fenilalcinos |
| CN1289469C (zh) | 2001-12-20 | 2006-12-13 | 布里斯托尔-迈尔斯斯奎布公司 | α－(N－磺酰氨基)乙酰胺衍生物作为β－淀粉样蛋白抑制剂 |
| 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 US US10/692,080 patent/US7279491B2/en not_active Expired - Lifetime
- 2003-10-23 AU AU2003287206A patent/AU2003287206A1/en not_active Abandoned
- 2003-10-23 JP JP2004547134A patent/JP2006505590A/ja not_active Withdrawn
- 2003-10-23 EP EP03781386A patent/EP1556046A1/en not_active Withdrawn
- 2003-10-23 CA CA002504272A patent/CA2504272A1/en not_active Abandoned
- 2003-10-23 WO PCT/US2003/033809 patent/WO2004037257A1/en not_active Ceased
-
2007
- 2007-08-08 US US11/835,880 patent/US20080004314A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2006505590A5 (https=) | ||
| JP2006510609A5 (https=) | ||
| CA2425876C (en) | Piperidine derivatives as antagonists of tachykinins | |
| RU2201927C2 (ru) | Амидиновые соединения и фармацевтическая композиция, обладающая фактор ха ингибирующим действием | |
| US9096571B2 (en) | Picolinamide and pyrimidine-4-carboxamide compounds, process for preparing and pharmaceutical composition comprising the same | |
| CN100415716C (zh) | 1－(1，2－双取代哌啶基)－4－取代哌嗪衍生物 | |
| JP6109575B2 (ja) | 置換されたベンズアミド誘導体 | |
| AU2002228072B2 (en) | Piperidinee derivatives as neurokinin 1 antagonists | |
| CA2504269A1 (en) | Piperazinyl and diazapanyl benzamides and benzthioamides | |
| HRP20140252T1 (hr) | Derivati imidazola kao inhibitori kazeinske kinaze | |
| JP2004525892A5 (https=) | ||
| JP2011503210A5 (https=) | ||
| NO310913B1 (no) | 1-(1,2-disubstituert piperidinyl)-4-substituert piperidinderivater som tachykinin reseptorantagonister | |
| JP5232143B2 (ja) | モチリン受容体アンタゴニストとしてのベンジルピペラジン誘導体 | |
| KR910009705A (ko) | 수용성이 개선된 이미다조[4,5-b] 퀴놀리닐 옥시알칸산 아미드 | |
| JP2007532596A5 (https=) | ||
| RU2005134006A (ru) | Производные 4-(4-{гетероциклилалкокси}фенил0-1-(гетероциклилкарбонил)пиперидина и родственные соединения как антагонисты гистамина н3 для лечения неврологических заболеваний, таких как болезнь альцгеймера | |
| CN1146559C (zh) | 毒蕈碱性拮抗剂 | |
| HUP0402567A2 (hu) | Piperidinszármazékok és alkalmazásuk kemokin receptor (különösen CCR5) aktivitás modulátoraiként | |
| NO327074B1 (no) | Cyklisk aminforbindelse, slike forbindelser for bruk som medikament, farmasoytiske blandinger inneholdende slike samt anvendelse av disse for fremstilling av medisin for behandling av sykdommer. | |
| US6395753B1 (en) | Cyclic amine compounds and pharmaceutical composition containing the same | |
| JP2007520466A5 (https=) | ||
| CN1541203A (zh) | 4-(苯基-(哌啶-4基)-氨基)-苯甲酰胺衍生物及其在治疗疼痛、焦虑症或胃肠病中的应用 | |
| WO2002055497A1 (en) | Aryl piperidine derivatives as inducers of ldl-receptor expression | |
| US6605620B1 (en) | Cyclic amine compounds and pharmaceutical composition containing the same |