JP2005511740A5 - - Google Patents
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- Publication number
- JP2005511740A5 JP2005511740A5 JP2003551124A JP2003551124A JP2005511740A5 JP 2005511740 A5 JP2005511740 A5 JP 2005511740A5 JP 2003551124 A JP2003551124 A JP 2003551124A JP 2003551124 A JP2003551124 A JP 2003551124A JP 2005511740 A5 JP2005511740 A5 JP 2005511740A5
- Authority
- JP
- Japan
- Prior art keywords
- ynyl
- piperidin
- benzyl
- phenyl
- piperidine
- 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- Withdrawn
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- -1 nitro, hydroxyl Chemical group 0.000 claims 79
- 150000001875 compounds Chemical class 0.000 claims 34
- 125000000623 heterocyclic group Chemical group 0.000 claims 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 24
- 125000000217 alkyl group Chemical group 0.000 claims 19
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims 12
- 125000002947 alkylene group Chemical group 0.000 claims 12
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 10
- 229910052757 nitrogen Inorganic materials 0.000 claims 9
- 125000001424 substituent group Chemical group 0.000 claims 9
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 102000005962 receptors Human genes 0.000 claims 8
- 108020003175 receptors Proteins 0.000 claims 8
- 125000004452 carbocyclyl group Chemical group 0.000 claims 6
- 208000035475 disorder Diseases 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- 229960001340 histamine Drugs 0.000 claims 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- 125000003386 piperidinyl group Chemical group 0.000 claims 6
- HDRIBIYPLKZUDQ-UHFFFAOYSA-N 4-[[3-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]morpholine Chemical compound C=1C=CC(CN2CCOCC2)=CC=1C#CCCN1CCCCC1 HDRIBIYPLKZUDQ-UHFFFAOYSA-N 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 5
- 206010012289 Dementia Diseases 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 125000002883 imidazolyl group Chemical group 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims 4
- 125000001425 triazolyl group Chemical group 0.000 claims 4
- 150000003857 carboxamides Chemical class 0.000 claims 3
- 208000010877 cognitive disease Diseases 0.000 claims 3
- 239000000938 histamine H1 antagonist Substances 0.000 claims 3
- 239000003485 histamine H2 receptor antagonist Substances 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 3
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- RFPKAGSDFZFKNX-UHFFFAOYSA-N 1-[[3-(4-morpholin-4-ylbut-1-ynyl)phenyl]methyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CC1=CC=CC(C#CCCN2CCOCC2)=C1 RFPKAGSDFZFKNX-UHFFFAOYSA-N 0.000 claims 2
- QISKARXISMFONU-UHFFFAOYSA-N 1-[[3-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]-4-[3-(trifluoromethyl)phenyl]piperazine Chemical compound FC(F)(F)C1=CC=CC(N2CCN(CC=3C=C(C=CC=3)C#CCCN3CCCCC3)CC2)=C1 QISKARXISMFONU-UHFFFAOYSA-N 0.000 claims 2
- ZWWUYWBXBLSYOS-UHFFFAOYSA-N 1-[[3-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CC1=CC=CC(C#CCCN2CCCCC2)=C1 ZWWUYWBXBLSYOS-UHFFFAOYSA-N 0.000 claims 2
- MEMJPSSYGARVOB-UHFFFAOYSA-N 1-[[3-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]piperidine-4-carboxamide Chemical compound C1CC(C(=O)N)CCN1CC1=CC=CC(C#CCCN2CCCCC2)=C1 MEMJPSSYGARVOB-UHFFFAOYSA-N 0.000 claims 2
- HNJWKRMESUMDQE-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-methylethanamine Chemical group CNCCC1=CC=C(OC)C(OC)=C1 HNJWKRMESUMDQE-UHFFFAOYSA-N 0.000 claims 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims 2
- HRGXROVFENCVIO-UHFFFAOYSA-N 3-[[3-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]-1,3-thiazolidine Chemical compound C=1C=CC(CN2CSCC2)=CC=1C#CCCN1CCCCC1 HRGXROVFENCVIO-UHFFFAOYSA-N 0.000 claims 2
- PAFPCBPHDUAMIX-UHFFFAOYSA-N 4-[4-[3-(thiomorpholin-4-ylmethyl)phenyl]but-3-ynyl]morpholine Chemical compound C=1C=CC(CN2CCSCC2)=CC=1C#CCCN1CCOCC1 PAFPCBPHDUAMIX-UHFFFAOYSA-N 0.000 claims 2
- ANDUWBDYYCFMSZ-UHFFFAOYSA-N 4-[4-[3-[(4-methylpiperazin-1-yl)methyl]phenyl]but-3-ynyl]morpholine Chemical compound C1CN(C)CCN1CC1=CC=CC(C#CCCN2CCOCC2)=C1 ANDUWBDYYCFMSZ-UHFFFAOYSA-N 0.000 claims 2
- NGJBPOOMWRYCPF-UHFFFAOYSA-N 4-[4-[3-[(4-methylpiperazin-1-yl)methyl]phenyl]but-3-ynyl]thiomorpholine Chemical compound C1CN(C)CCN1CC1=CC=CC(C#CCCN2CCSCC2)=C1 NGJBPOOMWRYCPF-UHFFFAOYSA-N 0.000 claims 2
- QIHBAGTXATWNMI-UHFFFAOYSA-N 4-methoxy-1-[[3-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]piperidine Chemical compound C1CC(OC)CCN1CC1=CC=CC(C#CCCN2CCCCC2)=C1 QIHBAGTXATWNMI-UHFFFAOYSA-N 0.000 claims 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- 206010028735 Nasal congestion Diseases 0.000 claims 2
- 206010062519 Poor quality sleep Diseases 0.000 claims 2
- 206010039085 Rhinitis allergic Diseases 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 201000010105 allergic rhinitis Diseases 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 230000037007 arousal Effects 0.000 claims 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 2
- 239000002552 dosage form Substances 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- 208000027061 mild cognitive impairment Diseases 0.000 claims 2
- XDQMOBHJYLWFRT-UHFFFAOYSA-N n-methyl-n-[[3-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]-2-pyridin-2-ylethanamine Chemical compound C=1C=CC(C#CCCN2CCCCC2)=CC=1CN(C)CCC1=CC=CC=N1 XDQMOBHJYLWFRT-UHFFFAOYSA-N 0.000 claims 2
- NCIKQJBVUNUXLW-UHFFFAOYSA-N n-omega-methyltryptamine Chemical group C1=CC=C2C(CCNC)=CNC2=C1 NCIKQJBVUNUXLW-UHFFFAOYSA-N 0.000 claims 2
- 201000003631 narcolepsy Diseases 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000001422 pyrrolinyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical group C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims 1
- QNSRHBOZQLXYNV-UHFFFAOYSA-N 1,4,7-trioxa-10-azacyclododecane Chemical group C1COCCOCCOCCN1 QNSRHBOZQLXYNV-UHFFFAOYSA-N 0.000 claims 1
- MRBFGEHILMYPTF-UHFFFAOYSA-N 1-(2-Pyrimidyl)piperazine Chemical group C1CNCCN1C1=NC=CC=N1 MRBFGEHILMYPTF-UHFFFAOYSA-N 0.000 claims 1
- KKIMDKMETPPURN-UHFFFAOYSA-N 1-(3-(trifluoromethyl)phenyl)piperazine Chemical group FC(F)(F)C1=CC=CC(N2CCNCC2)=C1 KKIMDKMETPPURN-UHFFFAOYSA-N 0.000 claims 1
- NZMRGJYRQBXRTL-UHFFFAOYSA-N 1-[4-[3-(aziridin-1-ylmethyl)phenyl]but-3-ynyl]piperidine Chemical compound C=1C=CC(CN2CC2)=CC=1C#CCCN1CCCCC1 NZMRGJYRQBXRTL-UHFFFAOYSA-N 0.000 claims 1
- CQEZMXAJOCXNTK-UHFFFAOYSA-N 1-[4-[3-(pyrrolidin-1-ylmethyl)phenyl]but-3-ynyl]piperidine Chemical compound C=1C=CC(CN2CCCC2)=CC=1C#CCCN1CCCCC1 CQEZMXAJOCXNTK-UHFFFAOYSA-N 0.000 claims 1
- KCDNDVYRBIJQQP-UHFFFAOYSA-N 1-[[3-(4-thiomorpholin-4-ylbut-1-ynyl)phenyl]methyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CC1=CC=CC(C#CCCN2CCSCC2)=C1 KCDNDVYRBIJQQP-UHFFFAOYSA-N 0.000 claims 1
- KJUYUPFAJWJDHB-UHFFFAOYSA-N 1-benzyl-4-[[4-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]piperazine Chemical compound C=1C=C(CN2CCN(CC=3C=CC=CC=3)CC2)C=CC=1C#CCCN1CCCCC1 KJUYUPFAJWJDHB-UHFFFAOYSA-N 0.000 claims 1
- NVYKUZPOGWHWQN-UHFFFAOYSA-N 1-methyl-4-[[3-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]piperazine Chemical compound C1CN(C)CCN1CC1=CC=CC(C#CCCN2CCCCC2)=C1 NVYKUZPOGWHWQN-UHFFFAOYSA-N 0.000 claims 1
- GNEXGCZJYUOOFU-UHFFFAOYSA-N 1-methyl-4-[[4-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]piperazine Chemical compound C1CN(C)CCN1CC1=CC=C(C#CCCN2CCCCC2)C=C1 GNEXGCZJYUOOFU-UHFFFAOYSA-N 0.000 claims 1
- HTQWGIHCFPWKAS-UHFFFAOYSA-N 1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one Chemical group C1CNCCC11C(=O)NCN1C1=CC=CC=C1 HTQWGIHCFPWKAS-UHFFFAOYSA-N 0.000 claims 1
- GZLFAQOQWQWXSE-UHFFFAOYSA-N 1-phenyl-4-[[4-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]piperazine Chemical compound C=1C=C(CN2CCN(CC2)C=2C=CC=CC=2)C=CC=1C#CCCN1CCCCC1 GZLFAQOQWQWXSE-UHFFFAOYSA-N 0.000 claims 1
- TZAXUPJWBWKZPL-UHFFFAOYSA-N 10-[[3-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]-1,4,7-trioxa-10-azacyclododecane Chemical compound C=1C=CC(CN2CCOCCOCCOCC2)=CC=1C#CCCN1CCCCC1 TZAXUPJWBWKZPL-UHFFFAOYSA-N 0.000 claims 1
- MAUNJNQYQQHKDB-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-methyl-n-[[3-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]ethanamine Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CC1=CC=CC(C#CCCN2CCCCC2)=C1 MAUNJNQYQQHKDB-UHFFFAOYSA-N 0.000 claims 1
- PGVWHUHUERGTCL-UHFFFAOYSA-N 2-[1-[[3-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]piperidin-4-yl]oxypyrimidine Chemical compound C=1C=CC(CN2CCC(CC2)OC=2N=CC=CN=2)=CC=1C#CCCN1CCCCC1 PGVWHUHUERGTCL-UHFFFAOYSA-N 0.000 claims 1
- DYDQDHCNGTXGJV-UHFFFAOYSA-N 2-[4-[[3-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]piperazin-1-yl]pyrimidine Chemical compound C=1C=CC(CN2CCN(CC2)C=2N=CC=CN=2)=CC=1C#CCCN1CCCCC1 DYDQDHCNGTXGJV-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
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 1
- DPBWFNDFMCCGGJ-UHFFFAOYSA-N 4-Piperidine carboxamide Chemical group NC(=O)C1CCNCC1 DPBWFNDFMCCGGJ-UHFFFAOYSA-N 0.000 claims 1
- KDCNZRKFUMNRBU-UHFFFAOYSA-N 4-[4-[3-[(4-methoxypiperidin-1-yl)methyl]phenyl]but-3-ynyl]thiomorpholine Chemical compound C1CC(OC)CCN1CC1=CC=CC(C#CCCN2CCSCC2)=C1 KDCNZRKFUMNRBU-UHFFFAOYSA-N 0.000 claims 1
- MYKKJZCGIIDDFB-UHFFFAOYSA-N 4-[[3-(4-morpholin-4-ylbut-1-ynyl)phenyl]methyl]morpholine Chemical compound C=1C=CC(CN2CCOCC2)=CC=1C#CCCN1CCOCC1 MYKKJZCGIIDDFB-UHFFFAOYSA-N 0.000 claims 1
- FSHOZBSEBOHWPV-UHFFFAOYSA-N 4-[[3-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]thiomorpholine Chemical compound C=1C=CC(CN2CCSCC2)=CC=1C#CCCN1CCCCC1 FSHOZBSEBOHWPV-UHFFFAOYSA-N 0.000 claims 1
- UTXBZYNRYPXBIF-UHFFFAOYSA-N 4-[[3-(4-thiomorpholin-4-ylbut-1-ynyl)phenyl]methyl]thiomorpholine Chemical compound C=1C=CC(CN2CCSCC2)=CC=1C#CCCN1CCSCC1 UTXBZYNRYPXBIF-UHFFFAOYSA-N 0.000 claims 1
- FUFZNHHSSMCXCZ-UHFFFAOYSA-N 5-piperidin-4-yl-3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazole Chemical compound FC(F)(F)C1=CC=CC(C=2N=C(ON=2)C2CCNCC2)=C1 FUFZNHHSSMCXCZ-UHFFFAOYSA-N 0.000 claims 1
- BJUFNUDBCWCZKX-UHFFFAOYSA-N 8-[[4-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]-1,4-dioxa-8-azaspiro[4.5]decane Chemical compound C=1C=C(CN2CCC3(CC2)OCCO3)C=CC=1C#CCCN1CCCCC1 BJUFNUDBCWCZKX-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
- 208000030814 Eating disease Diseases 0.000 claims 1
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 206010020751 Hypersensitivity Diseases 0.000 claims 1
- WZELXJBMMZFDDU-UHFFFAOYSA-N Imidazol-2-one Chemical compound O=C1N=CC=N1 WZELXJBMMZFDDU-UHFFFAOYSA-N 0.000 claims 1
- 208000020358 Learning 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
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000004450 alkenylene group Chemical group 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 208000030961 allergic reaction Diseases 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- MTXSIJUGVMTTMU-UHFFFAOYSA-N anabasine Chemical group N1CCCCC1C1=CC=CN=C1 MTXSIJUGVMTTMU-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 1
- 125000004069 aziridinyl group Chemical group 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
- UUQMNUMQCIQDMZ-UHFFFAOYSA-N betahistine Chemical group CNCCC1=CC=CC=N1 UUQMNUMQCIQDMZ-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 239000003814 drug Substances 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 201000003723 learning disability Diseases 0.000 claims 1
- 230000014759 maintenance of location Effects 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 201000003152 motion sickness Diseases 0.000 claims 1
- ZXQKYQVJDRTTLZ-UHFFFAOYSA-N n,n-diethylpiperidine-3-carboxamide Chemical group CCN(CC)C(=O)C1CCCNC1 ZXQKYQVJDRTTLZ-UHFFFAOYSA-N 0.000 claims 1
- BRNCNUHXAAXCET-UHFFFAOYSA-N n,n-dimethyl-1-[4-(4-piperidin-1-ylbut-1-ynyl)phenyl]methanamine Chemical compound C1=CC(CN(C)C)=CC=C1C#CCCN1CCCCC1 BRNCNUHXAAXCET-UHFFFAOYSA-N 0.000 claims 1
- CATAMUJOZCFLMP-UHFFFAOYSA-N n,n-dimethyl-4-[4-(piperidin-1-ylmethyl)phenyl]but-3-yn-1-amine Chemical compound C1=CC(C#CCCN(C)C)=CC=C1CN1CCCCC1 CATAMUJOZCFLMP-UHFFFAOYSA-N 0.000 claims 1
- LYXRZUISRBVWCN-UHFFFAOYSA-N n-[[4-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]-2,3-dihydro-1h-inden-1-amine Chemical compound C=1C=C(CNC2C3=CC=CC=C3CC2)C=CC=1C#CCCN1CCCCC1 LYXRZUISRBVWCN-UHFFFAOYSA-N 0.000 claims 1
- AXZSXPZOIMXFFJ-UHFFFAOYSA-N n-[[4-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]aniline Chemical compound C=1C=C(CNC=2C=CC=CC=2)C=CC=1C#CCCN1CCCCC1 AXZSXPZOIMXFFJ-UHFFFAOYSA-N 0.000 claims 1
- JKEPYAMUBPWXCQ-UHFFFAOYSA-N n-[[4-(4-piperidin-1-ylbut-1-ynyl)phenyl]methyl]cyclohexanamine Chemical compound C=1C=C(CNC2CCCCC2)C=CC=1C#CCCN1CCCCC1 JKEPYAMUBPWXCQ-UHFFFAOYSA-N 0.000 claims 1
- SBSLCPHONZWKIE-UHFFFAOYSA-N n-piperidin-4-ylpyridin-2-amine Chemical compound C1CNCCC1NC1=CC=CC=N1 SBSLCPHONZWKIE-UHFFFAOYSA-N 0.000 claims 1
- CTSIKBGUCQWRIM-UHFFFAOYSA-N n-prop-2-enylcyclopentanamine Chemical group C=CCNC1CCCC1 CTSIKBGUCQWRIM-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000000241 respiratory effect Effects 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33952301P | 2001-12-10 | 2001-12-10 | |
| PCT/US2002/038480 WO2003050099A1 (en) | 2001-12-10 | 2002-12-02 | Phenylalkynes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005511740A JP2005511740A (ja) | 2005-04-28 |
| JP2005511740A5 true JP2005511740A5 (https=) | 2006-01-19 |
Family
ID=23329400
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003551124A Withdrawn JP2005511740A (ja) | 2001-12-10 | 2002-12-02 | フェニルアルキン |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US6884803B2 (https=) |
| EP (1) | EP1451167B1 (https=) |
| JP (1) | JP2005511740A (https=) |
| KR (1) | KR20040068202A (https=) |
| CN (1) | CN1617865A (https=) |
| AR (1) | AR037757A1 (https=) |
| AT (1) | ATE319694T1 (https=) |
| AU (1) | AU2002357775A1 (https=) |
| BR (1) | BR0214886A (https=) |
| CA (1) | CA2469893A1 (https=) |
| CO (1) | CO5590900A2 (https=) |
| CY (1) | CY1105345T1 (https=) |
| DE (1) | DE60209794T2 (https=) |
| DK (1) | DK1451167T3 (https=) |
| EA (1) | EA200400661A1 (https=) |
| ES (1) | ES2259728T3 (https=) |
| IL (1) | IL162309A0 (https=) |
| MX (1) | MXPA04005562A (https=) |
| NO (1) | NO20042919L (https=) |
| NZ (1) | NZ533990A (https=) |
| PT (1) | PT1451167E (https=) |
| TW (1) | TWI281471B (https=) |
| WO (1) | WO2003050099A1 (https=) |
| ZA (1) | ZA200405452B (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040002604A1 (en) | 2001-12-10 | 2004-01-01 | Richard Apodaca | Phenylalkynes |
| EP1556046A1 (en) | 2002-10-23 | 2005-07-27 | Janssen Pharmaceutica N.V. | Phenylpiperidines and phenylpyrrolidines as histamine h3 receptor modulators |
| EP1558595B1 (en) | 2002-10-23 | 2009-11-25 | Janssen Pharmaceutica N.V. | Piperazinyl and diazapanyl benzamides and benzthioamides |
| AU2003245613A1 (en) * | 2002-12-02 | 2004-06-23 | Ortho-Mcneil Pharmaceutical, Inc. | Methods for preparing phenylalkyne derivatives |
| 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 |
| SI1948607T1 (sl) | 2005-09-16 | 2010-07-30 | Janssen Pharmaceutica Nv | Ciklopropil amini kot modulatorji histaminskega H3 receptorja |
| RU2470910C9 (ru) * | 2007-06-29 | 2013-05-20 | Акьюсела, Инк. | Соединения, представляющие собой алкинилфенильные производные, для лечения офтальмических заболеваний и расстройств |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| WO1999059969A1 (en) | 1998-05-15 | 1999-11-25 | American Home Products Corporation | Compositions comprising 2-phenyl-indole compounds and estrogen formulations |
| 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 |
| WO2001066534A2 (en) * | 2000-03-09 | 2001-09-13 | Abbott Laboratories | Cyclic and bicyclic diamino histamine-3 receptor antagonists |
| SE0002419D0 (sv) | 2000-06-27 | 2000-06-27 | Ericsson Telefon Ab L M | Telekommunikationsförfarande och anordning |
| 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 |
| WO2003060099A2 (en) | 2002-01-11 | 2003-07-24 | Nexia Biotechnologies, Inc. | Methods and apparatus for spinning spider silk protein |
-
2002
- 2002-12-02 ES ES02792315T patent/ES2259728T3/es not_active Expired - Lifetime
- 2002-12-02 BR BR0214886-2A patent/BR0214886A/pt not_active IP Right Cessation
- 2002-12-02 IL IL16230902A patent/IL162309A0/xx unknown
- 2002-12-02 EP EP02792315A patent/EP1451167B1/en not_active Expired - Lifetime
- 2002-12-02 AT AT02792315T patent/ATE319694T1/de not_active IP Right Cessation
- 2002-12-02 DE DE60209794T patent/DE60209794T2/de not_active Expired - Lifetime
- 2002-12-02 EA EA200400661A patent/EA200400661A1/ru unknown
- 2002-12-02 KR KR10-2004-7008770A patent/KR20040068202A/ko not_active Withdrawn
- 2002-12-02 MX MXPA04005562A patent/MXPA04005562A/es unknown
- 2002-12-02 NZ NZ533990A patent/NZ533990A/en unknown
- 2002-12-02 JP JP2003551124A patent/JP2005511740A/ja not_active Withdrawn
- 2002-12-02 PT PT02792315T patent/PT1451167E/pt unknown
- 2002-12-02 AU AU2002357775A patent/AU2002357775A1/en not_active Abandoned
- 2002-12-02 CA CA002469893A patent/CA2469893A1/en not_active Abandoned
- 2002-12-02 DK DK02792315T patent/DK1451167T3/da active
- 2002-12-02 WO PCT/US2002/038480 patent/WO2003050099A1/en not_active Ceased
- 2002-12-02 CN CNA028278194A patent/CN1617865A/zh active Pending
- 2002-12-02 US US10/307,870 patent/US6884803B2/en not_active Expired - Lifetime
- 2002-12-09 AR ARP020104760A patent/AR037757A1/es unknown
- 2002-12-10 TW TW091135617A patent/TWI281471B/zh not_active IP Right Cessation
-
2004
- 2004-06-17 CO CO04056829A patent/CO5590900A2/es not_active Application Discontinuation
- 2004-07-08 NO NO20042919A patent/NO20042919L/no not_active Application Discontinuation
- 2004-07-08 ZA ZA200405452A patent/ZA200405452B/en unknown
-
2006
- 2006-05-17 CY CY20061100639T patent/CY1105345T1/el unknown
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