JP2006510609A5 - - Google Patents
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- Publication number
- JP2006510609A5 JP2006510609A5 JP2004546967A JP2004546967A JP2006510609A5 JP 2006510609 A5 JP2006510609 A5 JP 2006510609A5 JP 2004546967 A JP2004546967 A JP 2004546967A JP 2004546967 A JP2004546967 A JP 2004546967A JP 2006510609 A5 JP2006510609 A5 JP 2006510609A5
- Authority
- JP
- Japan
- Prior art keywords
- methanone
- ylmethylphenyl
- phenyl
- isopropylpiperazin
- dihydrochloride
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 57
- 125000000217 alkyl group Chemical group 0.000 claims 22
- 125000000623 heterocyclic group Chemical group 0.000 claims 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 19
- -1 piperidin-1-ylmethyl Chemical group 0.000 claims 19
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 12
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 11
- 239000008194 pharmaceutical composition Substances 0.000 claims 9
- 102000005962 receptors Human genes 0.000 claims 9
- 108020003175 receptors Proteins 0.000 claims 9
- 208000035475 disorder Diseases 0.000 claims 8
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 8
- 125000003386 piperidinyl group Chemical group 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- 125000002947 alkylene group Chemical group 0.000 claims 6
- 125000003725 azepanyl group Chemical group 0.000 claims 6
- 125000005959 diazepanyl group Chemical group 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- 229960001340 histamine Drugs 0.000 claims 6
- 125000002757 morpholinyl group Chemical group 0.000 claims 6
- AQNQFXMDJLAVOU-UHFFFAOYSA-N (4-butan-2-ylpiperazin-1-yl)-[4-(piperidin-1-ylmethyl)phenyl]methanone Chemical compound C1CN(C(C)CC)CCN1C(=O)C(C=C1)=CC=C1CN1CCCCC1 AQNQFXMDJLAVOU-UHFFFAOYSA-N 0.000 claims 5
- PJAUZECIHOADBE-UHFFFAOYSA-N (4-pentan-3-ylpiperazin-1-yl)-[4-(piperidin-1-ylmethyl)phenyl]methanone Chemical compound C1CN(C(CC)CC)CCN1C(=O)C(C=C1)=CC=C1CN1CCCCC1 PJAUZECIHOADBE-UHFFFAOYSA-N 0.000 claims 5
- YDVOHRKXZGOHEG-UHFFFAOYSA-N [4-(azepan-1-ylmethyl)phenyl]-(4-butan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)CC)CCN1C(=O)C(C=C1)=CC=C1CN1CCCCCC1 YDVOHRKXZGOHEG-UHFFFAOYSA-N 0.000 claims 5
- DSNALXIKDKGHLJ-UHFFFAOYSA-N [4-(piperidin-1-ylmethyl)phenyl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C(C=C1)=CC=C1CN1CCCCC1 DSNALXIKDKGHLJ-UHFFFAOYSA-N 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- FXUFLERGGYYBSJ-UHFFFAOYSA-N (4-butan-2-ylpiperazin-1-yl)-[4-(morpholin-4-ylmethyl)phenyl]methanone;dihydrochloride Chemical compound Cl.Cl.C1CN(C(C)CC)CCN1C(=O)C(C=C1)=CC=C1CN1CCOCC1 FXUFLERGGYYBSJ-UHFFFAOYSA-N 0.000 claims 4
- ZXUDWXNHQQHHOG-UHFFFAOYSA-N (4-butan-2-ylpiperazin-1-yl)-[4-(pyrrolidin-1-ylmethyl)phenyl]methanone Chemical compound C1CN(C(C)CC)CCN1C(=O)C(C=C1)=CC=C1CN1CCCC1 ZXUDWXNHQQHHOG-UHFFFAOYSA-N 0.000 claims 4
- BBXGPXOLUQTZAV-UHFFFAOYSA-N (4-butan-2-ylpiperazin-1-yl)-[4-[(dimethylamino)methyl]phenyl]methanone Chemical compound C1CN(C(C)CC)CCN1C(=O)C1=CC=C(CN(C)C)C=C1 BBXGPXOLUQTZAV-UHFFFAOYSA-N 0.000 claims 4
- CVRHIQNRTHGXBL-UHFFFAOYSA-N (4-cyclohexylpiperazin-1-yl)-[4-(piperidin-1-ylmethyl)phenyl]methanone Chemical compound C=1C=C(CN2CCCCC2)C=CC=1C(=O)N(CC1)CCN1C1CCCCC1 CVRHIQNRTHGXBL-UHFFFAOYSA-N 0.000 claims 4
- CZSFUWHJOGCOQT-UHFFFAOYSA-N (4-pentan-3-ylpiperazin-1-yl)-[4-(pyrrolidin-1-ylmethyl)phenyl]methanone Chemical compound C1CN(C(CC)CC)CCN1C(=O)C(C=C1)=CC=C1CN1CCCC1 CZSFUWHJOGCOQT-UHFFFAOYSA-N 0.000 claims 4
- WOBNBEKMLTZEQM-UHFFFAOYSA-N (4-propan-2-ylpiperazin-1-yl)-[4-(pyrrolidin-1-ylmethyl)phenyl]methanone;dihydrochloride Chemical compound Cl.Cl.C1CN(C(C)C)CCN1C(=O)C(C=C1)=CC=C1CN1CCCC1 WOBNBEKMLTZEQM-UHFFFAOYSA-N 0.000 claims 4
- GFVFMRCJTPWIGF-UHFFFAOYSA-N (4-propan-2-ylpiperazin-1-yl)-[4-[[3-(trifluoromethyl)piperidin-1-yl]methyl]phenyl]methanone;dihydrochloride Chemical compound Cl.Cl.C1CN(C(C)C)CCN1C(=O)C(C=C1)=CC=C1CN1CC(C(F)(F)F)CCC1 GFVFMRCJTPWIGF-UHFFFAOYSA-N 0.000 claims 4
- 206010012289 Dementia Diseases 0.000 claims 4
- LMEVWMCUUXVYRX-UHFFFAOYSA-N [4-(azepan-1-ylmethyl)phenyl]-(4-propan-2-ylpiperazin-1-yl)methanone;dihydrochloride Chemical compound Cl.Cl.C1CN(C(C)C)CCN1C(=O)C(C=C1)=CC=C1CN1CCCCCC1 LMEVWMCUUXVYRX-UHFFFAOYSA-N 0.000 claims 4
- YLVOZJYPBJFSFJ-UHFFFAOYSA-N [4-(morpholin-4-ylmethyl)phenyl]-(4-pentan-3-ylpiperazin-1-yl)methanone;dihydrochloride Chemical compound Cl.Cl.C1CN(C(CC)CC)CCN1C(=O)C(C=C1)=CC=C1CN1CCOCC1 YLVOZJYPBJFSFJ-UHFFFAOYSA-N 0.000 claims 4
- JTBLLBRXTOEAIZ-UHFFFAOYSA-N [4-(morpholin-4-ylmethyl)phenyl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C(C=C1)=CC=C1CN1CCOCC1 JTBLLBRXTOEAIZ-UHFFFAOYSA-N 0.000 claims 4
- 239000004480 active ingredient Substances 0.000 claims 4
- 208000010877 cognitive disease Diseases 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 125000002883 imidazolyl group Chemical group 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 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 4
- 125000004193 piperazinyl group Chemical group 0.000 claims 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims 4
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 4
- 125000001425 triazolyl group Chemical group 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- NTTSVWFRPRPGSL-UHFFFAOYSA-N (4-butylpiperazin-1-yl)-[4-(morpholin-4-ylmethyl)phenyl]methanone Chemical compound C1CN(CCCC)CCN1C(=O)C(C=C1)=CC=C1CN1CCOCC1 NTTSVWFRPRPGSL-UHFFFAOYSA-N 0.000 claims 3
- UMYZWFAYEGAUKQ-UHFFFAOYSA-N (4-pentan-3-ylpiperazin-1-yl)-[4-[[3-(trifluoromethyl)piperidin-1-yl]methyl]phenyl]methanone;dihydrochloride Chemical compound Cl.Cl.C1CN(C(CC)CC)CCN1C(=O)C(C=C1)=CC=C1CN1CC(C(F)(F)F)CCC1 UMYZWFAYEGAUKQ-UHFFFAOYSA-N 0.000 claims 3
- BRKXEPOVUAANEO-UHFFFAOYSA-N (4-propan-2-ylpiperazin-1-yl)-[4-(thiomorpholin-4-ylmethyl)phenyl]methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C(C=C1)=CC=C1CN1CCSCC1 BRKXEPOVUAANEO-UHFFFAOYSA-N 0.000 claims 3
- OMZLNVHEKAYHQZ-UHFFFAOYSA-N (4-propan-2-ylpiperazin-1-yl)-[4-[(pyridin-2-ylamino)methyl]phenyl]methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C(C=C1)=CC=C1CNC1=CC=CC=N1 OMZLNVHEKAYHQZ-UHFFFAOYSA-N 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- 206010026749 Mania Diseases 0.000 claims 3
- OBVVMIGIVHXHAY-UHFFFAOYSA-N [4-(3,4,4a,5,6,7,8,8a-octahydro-1h-isoquinolin-2-ylmethyl)phenyl]-(4-pentan-3-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(CC)CC)CCN1C(=O)C(C=C1)=CC=C1CN1CC2CCCCC2CC1 OBVVMIGIVHXHAY-UHFFFAOYSA-N 0.000 claims 3
- NDCMXJLEPRYJQA-UHFFFAOYSA-N [4-(azepan-1-ylmethyl)phenyl]-(4-pentan-3-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(CC)CC)CCN1C(=O)C(C=C1)=CC=C1CN1CCCCCC1 NDCMXJLEPRYJQA-UHFFFAOYSA-N 0.000 claims 3
- UBXYHWUPXXOZHQ-UHFFFAOYSA-N [4-(diethylaminomethyl)phenyl]-(4-propan-2-ylpiperazin-1-yl)methanone;dihydrochloride Chemical compound Cl.Cl.C1=CC(CN(CC)CC)=CC=C1C(=O)N1CCN(C(C)C)CC1 UBXYHWUPXXOZHQ-UHFFFAOYSA-N 0.000 claims 3
- JZEBFUFSOGWXOE-UHFFFAOYSA-N [4-[(1-methoxypropan-2-ylamino)methyl]phenyl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1=CC(CNC(C)COC)=CC=C1C(=O)N1CCN(C(C)C)CC1 JZEBFUFSOGWXOE-UHFFFAOYSA-N 0.000 claims 3
- HEMGCELGHZBNNP-UHFFFAOYSA-N [4-[(2-methoxyethylamino)methyl]phenyl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1=CC(CNCCOC)=CC=C1C(=O)N1CCN(C(C)C)CC1 HEMGCELGHZBNNP-UHFFFAOYSA-N 0.000 claims 3
- QLIWADBXAORKRS-UHFFFAOYSA-N [4-[(benzylamino)methyl]phenyl]-(4-propan-2-ylpiperazin-1-yl)methanone;dihydrochloride Chemical compound Cl.Cl.C1CN(C(C)C)CCN1C(=O)C(C=C1)=CC=C1CNCC1=CC=CC=C1 QLIWADBXAORKRS-UHFFFAOYSA-N 0.000 claims 3
- POJSCBVLEPVECE-UHFFFAOYSA-N [4-[(dimethylamino)methyl]phenyl]-(4-pentan-3-ylpiperazin-1-yl)methanone;dihydrochloride Chemical compound Cl.Cl.C1CN(C(CC)CC)CCN1C(=O)C1=CC=C(CN(C)C)C=C1 POJSCBVLEPVECE-UHFFFAOYSA-N 0.000 claims 3
- GTYXNHAYBSHWLL-UHFFFAOYSA-N [4-[(dimethylamino)methyl]phenyl]-(4-propan-2-ylpiperazin-1-yl)methanone;dihydrochloride Chemical compound Cl.Cl.C1CN(C(C)C)CCN1C(=O)C1=CC=C(CN(C)C)C=C1 GTYXNHAYBSHWLL-UHFFFAOYSA-N 0.000 claims 3
- KWTTXWTWWPKHOC-UHFFFAOYSA-N [4-[[2-methoxyethyl(propyl)amino]methyl]phenyl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1=CC(CN(CCOC)CCC)=CC=C1C(=O)N1CCN(C(C)C)CC1 KWTTXWTWWPKHOC-UHFFFAOYSA-N 0.000 claims 3
- QSNGIHWLYIXPHW-UHFFFAOYSA-N [4-[[ethyl(2-methoxyethyl)amino]methyl]phenyl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1=CC(CN(CCOC)CC)=CC=C1C(=O)N1CCN(C(C)C)CC1 QSNGIHWLYIXPHW-UHFFFAOYSA-N 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000004452 carbocyclyl group Chemical group 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000001422 pyrrolinyl group Chemical group 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- YFTOGXGALVURKM-UHFFFAOYSA-N (4-butan-2-ylpiperazin-1-yl)-[4-[[3-(trifluoromethyl)piperidin-1-yl]methyl]phenyl]methanone;dihydrochloride Chemical compound Cl.Cl.C1CN(C(C)CC)CCN1C(=O)C(C=C1)=CC=C1CN1CC(C(F)(F)F)CCC1 YFTOGXGALVURKM-UHFFFAOYSA-N 0.000 claims 2
- DYRDMOISOZFIHC-UHFFFAOYSA-N (4-butylpiperazin-1-yl)-[4-[(dimethylamino)methyl]phenyl]methanone Chemical compound C1CN(CCCC)CCN1C(=O)C1=CC=C(CN(C)C)C=C1 DYRDMOISOZFIHC-UHFFFAOYSA-N 0.000 claims 2
- YHJVHZKJFNZUKO-UHFFFAOYSA-N (4-butylpiperazin-1-yl)-[4-[[3-(trifluoromethyl)piperidin-1-yl]methyl]phenyl]methanone Chemical compound C1CN(CCCC)CCN1C(=O)C(C=C1)=CC=C1CN1CC(C(F)(F)F)CCC1 YHJVHZKJFNZUKO-UHFFFAOYSA-N 0.000 claims 2
- OZEFFBHWWRSIQI-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[4-(morpholin-4-ylmethyl)phenyl]methanone;dihydrochloride Chemical compound Cl.Cl.C1CN(C)CCN1C(=O)C(C=C1)=CC=C1CN1CCOCC1 OZEFFBHWWRSIQI-UHFFFAOYSA-N 0.000 claims 2
- NIXYZZVUBZQMAO-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[4-(piperidin-1-ylmethyl)phenyl]methanone;dihydrochloride Chemical compound Cl.Cl.C1CN(C)CCN1C(=O)C(C=C1)=CC=C1CN1CCCCC1 NIXYZZVUBZQMAO-UHFFFAOYSA-N 0.000 claims 2
- DNCYBIWEMYYNKN-UHFFFAOYSA-N (4-propan-2-ylpiperazin-1-yl)-[4-[(4-propan-2-ylpiperazin-1-yl)methyl]phenyl]methanone Chemical compound C1CN(C(C)C)CCN1CC1=CC=C(C(=O)N2CCN(CC2)C(C)C)C=C1 DNCYBIWEMYYNKN-UHFFFAOYSA-N 0.000 claims 2
- VGRYSYGIGQYWPW-UHFFFAOYSA-N (4-propan-2-ylpiperazin-1-yl)-[4-[[[5-(trifluoromethyl)pyridin-2-yl]amino]methyl]phenyl]methanone;dihydrochloride Chemical compound Cl.Cl.C1CN(C(C)C)CCN1C(=O)C(C=C1)=CC=C1CNC1=CC=C(C(F)(F)F)C=N1 VGRYSYGIGQYWPW-UHFFFAOYSA-N 0.000 claims 2
- CHSWBOGCMFBMRF-UHFFFAOYSA-N (4-propan-2-ylpiperazin-1-yl)-[4-[[[6-(trifluoromethyl)pyridin-3-yl]amino]methyl]phenyl]methanone;dihydrochloride Chemical compound Cl.Cl.C1CN(C(C)C)CCN1C(=O)C(C=C1)=CC=C1CNC1=CC=C(C(F)(F)F)N=C1 CHSWBOGCMFBMRF-UHFFFAOYSA-N 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 2
- 208000020925 Bipolar disease Diseases 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
- XLRDWGHKLGGZKC-UHFFFAOYSA-N [3-(piperidin-1-ylmethyl)phenyl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C1=CC=CC(CN2CCCCC2)=C1 XLRDWGHKLGGZKC-UHFFFAOYSA-N 0.000 claims 2
- VEFWAZBDPOSKBN-UHFFFAOYSA-N [4-(anilinomethyl)phenyl]-(4-butan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)CC)CCN1C(=O)C(C=C1)=CC=C1CNC1=CC=CC=C1 VEFWAZBDPOSKBN-UHFFFAOYSA-N 0.000 claims 2
- COVZTMSLZVPQIW-UHFFFAOYSA-N [4-(anilinomethyl)phenyl]-(4-propan-2-ylpiperazin-1-yl)methanone;dihydrochloride Chemical compound Cl.Cl.C1CN(C(C)C)CCN1C(=O)C(C=C1)=CC=C1CNC1=CC=CC=C1 COVZTMSLZVPQIW-UHFFFAOYSA-N 0.000 claims 2
- 208000026935 allergic disease Diseases 0.000 claims 2
- 201000010105 allergic rhinitis Diseases 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
- 150000003857 carboxamides Chemical group 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 239000002552 dosage form Substances 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 239000000938 histamine H1 antagonist Substances 0.000 claims 2
- 239000003485 histamine H2 receptor antagonist Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 201000003723 learning disability Diseases 0.000 claims 2
- 208000027061 mild cognitive impairment Diseases 0.000 claims 2
- 201000003631 narcolepsy Diseases 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 238000002600 positron emission tomography Methods 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 230000001105 regulatory effect Effects 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 230000001225 therapeutic effect Effects 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- NRCMGFSQARHMMS-UHFFFAOYSA-N (4-butylpiperazin-1-yl)-[4-[[4-(trifluoromethyl)anilino]methyl]phenyl]methanone Chemical compound C1CN(CCCC)CCN1C(=O)C(C=C1)=CC=C1CNC1=CC=C(C(F)(F)F)C=C1 NRCMGFSQARHMMS-UHFFFAOYSA-N 0.000 claims 1
- VIRLAMQSVXOZLS-UHFFFAOYSA-N (4-octan-2-ylpiperazin-1-yl)-[4-(piperidin-1-ylmethyl)phenyl]methanone Chemical compound C1CN(C(C)CCCCCC)CCN1C(=O)C(C=C1)=CC=C1CN1CCCCC1 VIRLAMQSVXOZLS-UHFFFAOYSA-N 0.000 claims 1
- FEJYEFRCINULQY-UHFFFAOYSA-N (4-pentan-3-ylpiperazin-1-yl)-[4-[[4-(trifluoromethyl)anilino]methyl]phenyl]methanone;dihydrochloride Chemical compound Cl.Cl.C1CN(C(CC)CC)CCN1C(=O)C(C=C1)=CC=C1CNC1=CC=C(C(F)(F)F)C=C1 FEJYEFRCINULQY-UHFFFAOYSA-N 0.000 claims 1
- OGHKWFIGIDBLFO-UHFFFAOYSA-N (4-propan-2-ylpiperazin-1-yl)-[4-[[4-(trifluoromethyl)anilino]methyl]phenyl]methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C(C=C1)=CC=C1CNC1=CC=C(C(F)(F)F)C=C1 OGHKWFIGIDBLFO-UHFFFAOYSA-N 0.000 claims 1
- KBIIDENNVCCHKP-UHFFFAOYSA-N (4-propan-2-ylpiperazin-1-yl)-[4-[[[4-(trifluoromethyl)pyridin-2-yl]amino]methyl]phenyl]methanone;dihydrochloride Chemical compound Cl.Cl.C1CN(C(C)C)CCN1C(=O)C(C=C1)=CC=C1CNC1=CC(C(F)(F)F)=CC=N1 KBIIDENNVCCHKP-UHFFFAOYSA-N 0.000 claims 1
- 125000006273 (C1-C3) alkyl 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 compound C1CNCCN1C1=NC=CC=N1 MRBFGEHILMYPTF-UHFFFAOYSA-N 0.000 claims 1
- KKIMDKMETPPURN-UHFFFAOYSA-N 1-(3-(trifluoromethyl)phenyl)piperazine Chemical compound FC(F)(F)C1=CC=CC(N2CCNCC2)=C1 KKIMDKMETPPURN-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
- HNJWKRMESUMDQE-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-methylethanamine Chemical compound CNCCC1=CC=C(OC)C(OC)=C1 HNJWKRMESUMDQE-UHFFFAOYSA-N 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
- 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
- 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
- 208000026139 Memory disease Diseases 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 208000007920 Neurogenic Inflammation Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 206010062519 Poor quality sleep Diseases 0.000 claims 1
- 208000003251 Pruritus Diseases 0.000 claims 1
- 206010041349 Somnolence Diseases 0.000 claims 1
- HHUNKGKTNMLKNK-UHFFFAOYSA-N [3-(morpholin-4-ylmethyl)phenyl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C1=CC=CC(CN2CCOCC2)=C1 HHUNKGKTNMLKNK-UHFFFAOYSA-N 0.000 claims 1
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| ATE449766T1 (de) | 2002-10-23 | 2009-12-15 | Janssen Pharmaceutica Nv | Piperazinyl- und diazapanylbenzamide und- benzothioamide |
| GB0324159D0 (en) | 2003-10-15 | 2003-11-19 | Glaxo Group Ltd | Novel compounds |
| CA2561791A1 (en) * | 2004-03-31 | 2005-10-20 | Janssen Pharmaceutica, N.V. | Non-imidazole heterocyclic compounds |
| JP2007531755A (ja) * | 2004-03-31 | 2007-11-08 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 非イミダゾール系複素環式化合物 |
| KR101336106B1 (ko) | 2005-09-16 | 2013-12-05 | 얀센 파마슈티카 엔.브이. | 히스타민 ｈ3 수용체의 조절제로서 사이클로프로필 아민 |
| US7795426B2 (en) | 2005-10-31 | 2010-09-14 | Janssen Pharmaceutica Nv | Processes for the preparation of cyclopropyl-amide derivatives |
| EP1951699B1 (en) | 2005-10-31 | 2012-10-10 | Janssen Pharmaceutica NV | Processes for the preparation of cyclopropyl-amide derivatives |
| CN101389617A (zh) | 2005-10-31 | 2009-03-18 | 詹森药业有限公司 | 制备哌嗪基和二氮杂环庚烷基苯甲酰胺衍生物的新方法 |
| KR101318127B1 (ko) * | 2005-11-10 | 2013-10-16 | 엠에스디 가부시키가이샤 | 아자 치환된 스피로 유도체 |
| EA015555B1 (ru) * | 2006-05-30 | 2011-08-30 | Янссен Фармацевтика Н.В. | Замещенные пиридиламидные соединения в качестве модуляторов гистаминового h-рецептора |
| KR20090024811A (ko) | 2006-06-23 | 2009-03-09 | 아보트 러보러터리즈 | 히스타민 ｈ3 수용체 조절제로서의 사이클로프로필 아민 유도체 |
| US9108948B2 (en) | 2006-06-23 | 2015-08-18 | Abbvie Inc. | Cyclopropyl amine derivatives |
| AU2007265238A1 (en) * | 2006-06-29 | 2008-01-03 | Janssen Pharmaceutica N.V. | Substituted benzamide modulators of the histamine H3 receptor |
| CA2672661C (en) | 2006-12-14 | 2015-04-28 | Janssen Pharmaceutica N.V. | Process for the preparation of piperazinyl and diazepanyl benzamide derivatives |
| TW200918527A (en) * | 2007-09-06 | 2009-05-01 | Glaxo Group Ltd | Piperazine derivative having affinity for the histamine H3 receptor |
| AR068509A1 (es) * | 2007-09-19 | 2009-11-18 | Jerini Ag | Antagosnistas del receptor de bradiquinina b1 |
| CA2706328C (en) | 2007-11-20 | 2016-04-19 | Janssen Pharmaceutica N.V. | Cycloalkyloxy- and heterocycloalkyloxypyridine compounds as modulators of the histamine h3 receptor |
| US20100130477A1 (en) * | 2008-11-25 | 2010-05-27 | Astrazeneca Ab | Spirocyclobutyl Piperidine Derivatives |
| SI3216784T1 (sl) * | 2009-03-18 | 2019-05-31 | Janssen Pharmaceutica Nv | Postopek za pripravo modulatorjev histaminskih H3 receptorjev |
| US9186353B2 (en) | 2009-04-27 | 2015-11-17 | Abbvie Inc. | Treatment of osteoarthritis pain |
| US8853390B2 (en) | 2010-09-16 | 2014-10-07 | Abbvie Inc. | Processes for preparing 1,2-substituted cyclopropyl derivatives |
| RU2700595C1 (ru) * | 2019-07-30 | 2019-09-18 | Общество с ограниченной ответственностью "Кью Эм Фарма" | Производное 3,6,9-триазатрициклотетрадекана и его применение для лечения депрессии |
| WO2022113008A1 (en) | 2020-11-27 | 2022-06-02 | Richter Gedeon Nyrt. | Histamine h3 receptor antagonists/inverse agonists for the treatment of autism spectrum disorder |
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- 2003-10-21 WO PCT/US2003/033343 patent/WO2004037801A1/en not_active Ceased
- 2003-10-21 EA EA200500528A patent/EA009860B1/ru unknown
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- 2003-10-21 KR KR1020057006864A patent/KR101067732B1/ko not_active Expired - Fee Related
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- 2003-10-21 BR BRPI0315644A patent/BRPI0315644B8/pt not_active IP Right Cessation
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