JP2009542708A5 - - Google Patents
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- JP2009542708A5 JP2009542708A5 JP2009518465A JP2009518465A JP2009542708A5 JP 2009542708 A5 JP2009542708 A5 JP 2009542708A5 JP 2009518465 A JP2009518465 A JP 2009518465A JP 2009518465 A JP2009518465 A JP 2009518465A JP 2009542708 A5 JP2009542708 A5 JP 2009542708A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- phenyl
- diazepan
- methanone
- cyclopropyl
- 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- Withdrawn
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- 125000000217 alkyl group Chemical group 0.000 claims 83
- -1 —OH Chemical group 0.000 claims 79
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 26
- 150000001875 compounds Chemical class 0.000 claims 25
- 208000035475 disorder Diseases 0.000 claims 16
- 125000005843 halogen group Chemical group 0.000 claims 15
- 239000008194 pharmaceutical composition Substances 0.000 claims 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 10
- 201000010099 disease Diseases 0.000 claims 10
- 125000003342 alkenyl group Chemical group 0.000 claims 9
- 125000000304 alkynyl group Chemical group 0.000 claims 6
- 125000004122 cyclic group Chemical group 0.000 claims 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 208000010877 cognitive disease Diseases 0.000 claims 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 5
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 239000002207 metabolite Substances 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 239000000651 prodrug Substances 0.000 claims 4
- 229940002612 prodrug Drugs 0.000 claims 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- 208000026139 Memory disease Diseases 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 208000019116 sleep disease Diseases 0.000 claims 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 2
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 2
- 208000000044 Amnesia Diseases 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
- 208000028698 Cognitive impairment Diseases 0.000 claims 2
- 206010012289 Dementia Diseases 0.000 claims 2
- 208000030814 Eating disease Diseases 0.000 claims 2
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 2
- 206010024264 Lethargy Diseases 0.000 claims 2
- 102000019208 Serotonin Plasma Membrane Transport Proteins Human genes 0.000 claims 2
- 108010012996 Serotonin Plasma Membrane Transport Proteins Proteins 0.000 claims 2
- 206010041349 Somnolence Diseases 0.000 claims 2
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 2
- 235000014632 disordered eating Nutrition 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 206010016256 fatigue Diseases 0.000 claims 2
- 229960001340 histamine Drugs 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 230000006984 memory degeneration Effects 0.000 claims 2
- 206010027175 memory impairment Diseases 0.000 claims 2
- 208000023060 memory loss Diseases 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 claims 2
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 claims 2
- 208000020685 sleep-wake disease Diseases 0.000 claims 2
- GNTOQRRKRNHLBL-UHFFFAOYSA-N (4-cyclobutyl-1,4-diazepan-1-yl)-[4-(3,4-dichlorophenoxy)-3-(methylaminomethyl)phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CCC2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 GNTOQRRKRNHLBL-UHFFFAOYSA-N 0.000 claims 1
- AJJXEACVSPXKMS-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[3-(3,4-dichlorophenoxy)-4-(methylaminomethyl)phenyl]methanone Chemical compound CNCC1=CC=C(C(=O)N2CCN(CCC2)C2CC2)C=C1OC1=CC=C(Cl)C(Cl)=C1 AJJXEACVSPXKMS-UHFFFAOYSA-N 0.000 claims 1
- HASNZFFRDSPBMJ-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[3-(methylaminomethyl)-4-(3-methyl-4-methylsulfanylphenoxy)phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=C(SC)C(C)=C1 HASNZFFRDSPBMJ-UHFFFAOYSA-N 0.000 claims 1
- DGRXLTADUFHHBN-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[3-(methylaminomethyl)-4-(4-methylsulfanylphenoxy)phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=C(SC)C=C1 DGRXLTADUFHHBN-UHFFFAOYSA-N 0.000 claims 1
- IRQHEXHOAZGQDN-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[3-(methylaminomethyl)-4-(6-methylpyridin-3-yl)oxyphenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=C(C)N=C1 IRQHEXHOAZGQDN-UHFFFAOYSA-N 0.000 claims 1
- WRACQGSYQITGPK-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[3-(methylaminomethyl)-4-[2-(trifluoromethoxy)phenoxy]phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=CC=C1OC(F)(F)F WRACQGSYQITGPK-UHFFFAOYSA-N 0.000 claims 1
- BPYJWNTUBNVSJN-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[3-(methylaminomethyl)-4-[2-(trifluoromethyl)phenoxy]phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=CC=C1C(F)(F)F BPYJWNTUBNVSJN-UHFFFAOYSA-N 0.000 claims 1
- DMKNBJGZUPGVEW-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[3-(methylaminomethyl)-4-[4-(trifluoromethyl)phenoxy]phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 DMKNBJGZUPGVEW-UHFFFAOYSA-N 0.000 claims 1
- JTTOIYGKVCKBNW-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[3-(methylaminomethyl)-4-[4-(trifluoromethyl)pyridin-2-yl]sulfanylphenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1SC1=CC(C(F)(F)F)=CC=N1 JTTOIYGKVCKBNW-UHFFFAOYSA-N 0.000 claims 1
- PUCXAAZLYORUSG-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[3-(methylaminomethyl)-4-[4-(trifluoromethylsulfanyl)phenoxy]phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=C(SC(F)(F)F)C=C1 PUCXAAZLYORUSG-UHFFFAOYSA-N 0.000 claims 1
- ZRHGDWMRFCDZHY-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[3-(methylaminomethyl)-4-phenoxyphenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=CC=C1 ZRHGDWMRFCDZHY-UHFFFAOYSA-N 0.000 claims 1
- NTCDZWFHVBSFMK-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[3-(methylaminomethyl)-4-pyridin-2-yloxyphenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=CC=N1 NTCDZWFHVBSFMK-UHFFFAOYSA-N 0.000 claims 1
- MJSYNNLNHBQPKS-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[3-(methylaminomethyl)-4-pyridin-2-ylsulfanylphenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1SC1=CC=CC=N1 MJSYNNLNHBQPKS-UHFFFAOYSA-N 0.000 claims 1
- SZLNZRZZYLIKDT-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[3-(methylaminomethyl)-4-pyridin-3-yloxyphenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=CN=C1 SZLNZRZZYLIKDT-UHFFFAOYSA-N 0.000 claims 1
- ABRACSMRTBYWFF-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[3-[(dimethylamino)methyl]-4-(6-methylpyridin-3-yl)oxyphenyl]methanone Chemical compound CN(C)CC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=C(C)N=C1 ABRACSMRTBYWFF-UHFFFAOYSA-N 0.000 claims 1
- RWTPCDGKWMQRGA-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[4-(2,3-dichlorophenoxy)-3-(methylaminomethyl)phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=CC(Cl)=C1Cl RWTPCDGKWMQRGA-UHFFFAOYSA-N 0.000 claims 1
- LNWOQXOSMRBZBN-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[4-(2,3-difluorophenoxy)-3-(methylaminomethyl)phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=CC(F)=C1F LNWOQXOSMRBZBN-UHFFFAOYSA-N 0.000 claims 1
- ORIYQOUBEPERFH-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[4-(2-fluorophenoxy)-3-(methylaminomethyl)phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=CC=C1F ORIYQOUBEPERFH-UHFFFAOYSA-N 0.000 claims 1
- ANDYBNKRXGVQGP-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[4-(3,4-dichlorophenoxy)-3-(methylaminomethyl)phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 ANDYBNKRXGVQGP-UHFFFAOYSA-N 0.000 claims 1
- PIVRFBAMCBQCDZ-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[4-(3-fluorophenoxy)-3-(methylaminomethyl)phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=CC(F)=C1 PIVRFBAMCBQCDZ-UHFFFAOYSA-N 0.000 claims 1
- DIKWOUATAGYMJW-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[4-(3-methoxyphenoxy)-3-(methylaminomethyl)phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=CC(OC)=C1 DIKWOUATAGYMJW-UHFFFAOYSA-N 0.000 claims 1
- LOMPCAVUANIGGY-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[4-(4-fluorophenoxy)-3-(methylaminomethyl)phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=C(F)C=C1 LOMPCAVUANIGGY-UHFFFAOYSA-N 0.000 claims 1
- OWBACNIWWBKBHC-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[4-(morpholin-4-ylmethyl)-3-pyridin-3-yloxyphenyl]methanone Chemical compound C=1C=C(CN2CCOCC2)C(OC=2C=NC=CC=2)=CC=1C(=O)N(CC1)CCCN1C1CC1 OWBACNIWWBKBHC-UHFFFAOYSA-N 0.000 claims 1
- KMHZJBNYIWFWAY-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[4-(piperidin-1-ylmethyl)-3-pyridin-3-yloxyphenyl]methanone Chemical compound C=1C=C(CN2CCCCC2)C(OC=2C=NC=CC=2)=CC=1C(=O)N(CC1)CCCN1C1CC1 KMHZJBNYIWFWAY-UHFFFAOYSA-N 0.000 claims 1
- NURMXNUIQVJHSR-UHFFFAOYSA-N (4-cyclopropyl-1,4-diazepan-1-yl)-[4-[(3,4-dichlorophenyl)methoxy]-3-(methylaminomethyl)phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OCC1=CC=C(Cl)C(Cl)=C1 NURMXNUIQVJHSR-UHFFFAOYSA-N 0.000 claims 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 1
- YFGHCGITMMYXAQ-UHFFFAOYSA-N 2-[(diphenylmethyl)sulfinyl]acetamide Chemical compound C=1C=CC=CC=1C(S(=O)CC(=O)N)C1=CC=CC=C1 YFGHCGITMMYXAQ-UHFFFAOYSA-N 0.000 claims 1
- XTALQXXENKAGEX-UHFFFAOYSA-N 2-[4-(4-cyclopropyl-1,4-diazepane-1-carbonyl)-2-(methylaminomethyl)phenoxy]benzonitrile Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=CC=C1C#N XTALQXXENKAGEX-UHFFFAOYSA-N 0.000 claims 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 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
- UWCGILLDYHOPEU-UHFFFAOYSA-N 3-[4-(4-cyclopropyl-1,4-diazepane-1-carbonyl)-2-(methylaminomethyl)phenoxy]benzonitrile Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=CC(C#N)=C1 UWCGILLDYHOPEU-UHFFFAOYSA-N 0.000 claims 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 1
- 125000006305 3-iodophenyl group Chemical group [H]C1=C([H])C(I)=C([H])C(*)=C1[H] 0.000 claims 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- NLHDACBKUHRZEW-UHFFFAOYSA-N 4-[4-(4-cyclopropyl-1,4-diazepane-1-carbonyl)-2-(methylaminomethyl)phenoxy]benzonitrile Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=C(C#N)C=C1 NLHDACBKUHRZEW-UHFFFAOYSA-N 0.000 claims 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims 1
- 229940100578 Acetylcholinesterase inhibitor Drugs 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims 1
- 208000007590 Disorders of Excessive Somnolence Diseases 0.000 claims 1
- 206010013578 Dizziness postural Diseases 0.000 claims 1
- 208000001456 Jet Lag Syndrome Diseases 0.000 claims 1
- 208000020358 Learning disease Diseases 0.000 claims 1
- 206010026749 Mania Diseases 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 208000016285 Movement disease Diseases 0.000 claims 1
- 208000007920 Neurogenic Inflammation Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 208000025535 REM sleep behavior disease Diseases 0.000 claims 1
- 208000005793 Restless legs syndrome Diseases 0.000 claims 1
- 229940121991 Serotonin and norepinephrine reuptake inhibitor Drugs 0.000 claims 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims 1
- 208000032140 Sleepiness Diseases 0.000 claims 1
- 208000009205 Tinnitus Diseases 0.000 claims 1
- KJADKKWYZYXHBB-XBWDGYHZSA-N Topiramic acid Chemical compound C1O[C@@]2(COS(N)(=O)=O)OC(C)(C)O[C@H]2[C@@H]2OC(C)(C)O[C@@H]21 KJADKKWYZYXHBB-XBWDGYHZSA-N 0.000 claims 1
- FSAUBGQRVAOUAE-UHFFFAOYSA-N [3-(methylaminomethyl)-4-(4-methylsulfanylphenoxy)phenyl]-(4-propan-2-yl-1,4-diazepan-1-yl)methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C(C)C)=CC=C1OC1=CC=C(SC)C=C1 FSAUBGQRVAOUAE-UHFFFAOYSA-N 0.000 claims 1
- BUDXPODSGXONSZ-UHFFFAOYSA-N [3-(methylaminomethyl)-4-[4-(trifluoromethyl)phenoxy]phenyl]-(4-propan-2-yl-1,4-diazepan-1-yl)methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C(C)C)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 BUDXPODSGXONSZ-UHFFFAOYSA-N 0.000 claims 1
- GTKIXXYJXPDXOP-UHFFFAOYSA-N [3-[(cyclopropylamino)methyl]-4-(3,4-dichlorophenoxy)phenyl]-(4-cyclopropyl-1,4-diazepan-1-yl)methanone Chemical compound C1=C(Cl)C(Cl)=CC=C1OC1=CC=C(C(=O)N2CCN(CCC2)C2CC2)C=C1CNC1CC1 GTKIXXYJXPDXOP-UHFFFAOYSA-N 0.000 claims 1
- FUZGNJYLLVRAMT-UHFFFAOYSA-N [3-[(cyclopropylamino)methyl]-4-(3,4-dichlorophenoxy)phenyl]-(4-propan-2-yl-1,4-diazepan-1-yl)methanone Chemical compound C1CN(C(C)C)CCCN1C(=O)C(C=C1CNC2CC2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 FUZGNJYLLVRAMT-UHFFFAOYSA-N 0.000 claims 1
- NQRPBAJKYSQQRJ-UHFFFAOYSA-N [3-[(cyclopropylamino)methyl]-4-pyridin-3-yloxyphenyl]-(4-cyclopropyl-1,4-diazepan-1-yl)methanone Chemical compound C=1C=C(OC=2C=NC=CC=2)C(CNC2CC2)=CC=1C(=O)N(CC1)CCCN1C1CC1 NQRPBAJKYSQQRJ-UHFFFAOYSA-N 0.000 claims 1
- QYNGZGASLPHHCL-UHFFFAOYSA-N [3-phenylmethoxy-4-(piperidin-1-ylmethyl)phenyl]-(4-propan-2-yl-1,4-diazepan-1-yl)methanone Chemical compound C1CN(C(C)C)CCCN1C(=O)C(C=C1OCC=2C=CC=CC=2)=CC=C1CN1CCCCC1 QYNGZGASLPHHCL-UHFFFAOYSA-N 0.000 claims 1
- HYGYMUXCJFZKTO-UHFFFAOYSA-N [4-(2-chloro-4-fluorophenoxy)-3-(methylaminomethyl)phenyl]-(4-cyclopropyl-1,4-diazepan-1-yl)methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=C(F)C=C1Cl HYGYMUXCJFZKTO-UHFFFAOYSA-N 0.000 claims 1
- MAQNQIWTRFNBKG-UHFFFAOYSA-N [4-(2-chloro-4-fluorophenoxy)-3-(methylaminomethyl)phenyl]-(4-propan-2-yl-1,4-diazepan-1-yl)methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C(C)C)=CC=C1OC1=CC=C(F)C=C1Cl MAQNQIWTRFNBKG-UHFFFAOYSA-N 0.000 claims 1
- DTGQAURGKWOQAA-UHFFFAOYSA-N [4-(3,4-dichlorophenoxy)-3-(methylaminomethyl)phenyl]-(4-propan-2-yl-1,4-diazepan-1-yl)methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C(C)C)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 DTGQAURGKWOQAA-UHFFFAOYSA-N 0.000 claims 1
- IIIHKNDFLNZYSC-UHFFFAOYSA-N [4-(3-chloro-2-fluorophenoxy)-3-(methylaminomethyl)phenyl]-(4-cyclopropyl-1,4-diazepan-1-yl)methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=CC(Cl)=C1F IIIHKNDFLNZYSC-UHFFFAOYSA-N 0.000 claims 1
- GMTUNRCWXIGLSX-UHFFFAOYSA-N [4-(3-chloro-4-fluorophenoxy)-3-(methylaminomethyl)phenyl]-(4-cyclopropyl-1,4-diazepan-1-yl)methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=C(F)C(Cl)=C1 GMTUNRCWXIGLSX-UHFFFAOYSA-N 0.000 claims 1
- QUZXTJYADOYRDB-UHFFFAOYSA-N [4-(3-chlorophenoxy)-3-(methylaminomethyl)phenyl]-(4-cyclopropyl-1,4-diazepan-1-yl)methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=CC(Cl)=C1 QUZXTJYADOYRDB-UHFFFAOYSA-N 0.000 claims 1
- RGPYWCVMPLKNBH-UHFFFAOYSA-N [4-(3-chlorophenoxy)-3-(methylaminomethyl)phenyl]-(4-propan-2-yl-1,4-diazepan-1-yl)methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C(C)C)=CC=C1OC1=CC=CC(Cl)=C1 RGPYWCVMPLKNBH-UHFFFAOYSA-N 0.000 claims 1
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- LUJLISGGFLGFKZ-UHFFFAOYSA-N [4-(4-chlorophenoxy)-3-(methylaminomethyl)phenyl]-(4-cyclopropyl-1,4-diazepan-1-yl)methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=C(Cl)C=C1 LUJLISGGFLGFKZ-UHFFFAOYSA-N 0.000 claims 1
- CVFUNUQUAWLUGT-UHFFFAOYSA-N [4-(4-chlorophenoxy)-3-(methylaminomethyl)phenyl]-(4-propan-2-yl-1,4-diazepan-1-yl)methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C(C)C)=CC=C1OC1=CC=C(Cl)C=C1 CVFUNUQUAWLUGT-UHFFFAOYSA-N 0.000 claims 1
- QSYJJNOIIJRBCL-UHFFFAOYSA-N [4-(4-chlorophenoxy)-3-(methylaminomethyl)phenyl]-(5-propan-2-yl-2,5-diazabicyclo[2.2.1]heptan-2-yl)methanone Chemical compound CNCC1=CC(C(=O)N2C3CC(N(C3)C(C)C)C2)=CC=C1OC1=CC=C(Cl)C=C1 QSYJJNOIIJRBCL-UHFFFAOYSA-N 0.000 claims 1
- PYHIXIXROUXPRF-UHFFFAOYSA-N [4-(4-chlorophenoxy)-3-[(cyclopropylamino)methyl]phenyl]-(4-cyclopropyl-1,4-diazepan-1-yl)methanone Chemical compound C1=CC(Cl)=CC=C1OC1=CC=C(C(=O)N2CCN(CCC2)C2CC2)C=C1CNC1CC1 PYHIXIXROUXPRF-UHFFFAOYSA-N 0.000 claims 1
- XQIMZDXBCQKPGH-UHFFFAOYSA-N [4-(4-chlorophenoxy)-3-[(cyclopropylamino)methyl]phenyl]-(4-propan-2-yl-1,4-diazepan-1-yl)methanone Chemical compound C1CN(C(C)C)CCCN1C(=O)C(C=C1CNC2CC2)=CC=C1OC1=CC=C(Cl)C=C1 XQIMZDXBCQKPGH-UHFFFAOYSA-N 0.000 claims 1
- WVDZKFHNTDXNHW-UHFFFAOYSA-N [4-(4-chlorophenoxy)-3-[[cyclopropyl(methyl)amino]methyl]phenyl]-(4-cyclopropyl-1,4-diazepan-1-yl)methanone Chemical compound C1CC1N(C)CC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=C(Cl)C=C1 WVDZKFHNTDXNHW-UHFFFAOYSA-N 0.000 claims 1
- LMZUKDCJCWRZBR-UHFFFAOYSA-N [4-(4-chlorophenyl)sulfanyl-3-(methylaminomethyl)phenyl]-(4-cyclopropyl-1,4-diazepan-1-yl)methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C2CC2)=CC=C1SC1=CC=C(Cl)C=C1 LMZUKDCJCWRZBR-UHFFFAOYSA-N 0.000 claims 1
- RWOGAYUMNHAMLE-UHFFFAOYSA-N [4-(4-chlorophenyl)sulfanyl-3-(methylaminomethyl)phenyl]-(5-propan-2-yl-2,5-diazabicyclo[2.2.1]heptan-2-yl)methanone Chemical compound CNCC1=CC(C(=O)N2C3CC(N(C3)C(C)C)C2)=CC=C1SC1=CC=C(Cl)C=C1 RWOGAYUMNHAMLE-UHFFFAOYSA-N 0.000 claims 1
- DPWSSZGTQMQUTM-UHFFFAOYSA-N [4-[(cyclopropylamino)methyl]-3-pyridin-3-yloxyphenyl]-(4-cyclopropyl-1,4-diazepan-1-yl)methanone Chemical compound C=1C=C(CNC2CC2)C(OC=2C=NC=CC=2)=CC=1C(=O)N(CC1)CCCN1C1CC1 DPWSSZGTQMQUTM-UHFFFAOYSA-N 0.000 claims 1
- URRKXZIAXKKOAU-UHFFFAOYSA-N [4-[(dimethylamino)methyl]-3-(2,6-dimethylpyridin-3-yl)oxyphenyl]-(4-propan-2-yl-1,4-diazepan-1-yl)methanone Chemical compound C1CN(C(C)C)CCCN1C(=O)C1=CC=C(CN(C)C)C(OC=2C(=NC(C)=CC=2)C)=C1 URRKXZIAXKKOAU-UHFFFAOYSA-N 0.000 claims 1
- PKFXVENTYDHHPZ-UHFFFAOYSA-N [4-[4-chloro-3-(trifluoromethyl)phenoxy]-3-(methylaminomethyl)phenyl]-(4-propan-2-yl-1,4-diazepan-1-yl)methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CCC2)C(C)C)=CC=C1OC1=CC=C(Cl)C(C(F)(F)F)=C1 PKFXVENTYDHHPZ-UHFFFAOYSA-N 0.000 claims 1
- OZMICXPEMZDZPC-UHFFFAOYSA-N [4-[[2-(hydroxymethyl)morpholin-4-yl]methyl]-3-phenoxyphenyl]-(4-propan-2-yl-1,4-diazepan-1-yl)methanone Chemical compound C1CN(C(C)C)CCCN1C(=O)C(C=C1OC=2C=CC=CC=2)=CC=C1CN1CC(CO)OCC1 OZMICXPEMZDZPC-UHFFFAOYSA-N 0.000 claims 1
- VDNZYSMPDQTVEA-UHFFFAOYSA-N [4-[[bis(2-methoxyethyl)amino]methyl]-3-phenylmethoxyphenyl]-(4-cyclopropyl-1,4-diazepan-1-yl)methanone Chemical compound COCCN(CCOC)CC1=CC=C(C(=O)N2CCN(CCC2)C2CC2)C=C1OCC1=CC=CC=C1 VDNZYSMPDQTVEA-UHFFFAOYSA-N 0.000 claims 1
- 230000032683 aging Effects 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
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- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims 1
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- 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
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
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- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
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- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
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- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 1
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| US80616706P | 2006-06-29 | 2006-06-29 | |
| PCT/US2007/071739 WO2008002818A1 (en) | 2006-06-29 | 2007-06-21 | Substituted aminomethyl benzamide compounds |
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| JP2009542708A JP2009542708A (ja) | 2009-12-03 |
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| SI1668014T1 (sl) * | 2003-09-17 | 2009-06-30 | Janssen Pharmaceutica Nv | Kondenzirane heterociklične spojine kot modulatorji serotoninskih receptorjev |
| US7598255B2 (en) * | 2005-08-04 | 2009-10-06 | Janssen Pharmaceutica Nv | Pyrimidine compounds as serotonin receptor modulators |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| EP2257536A4 (en) * | 2008-02-14 | 2011-03-23 | Amira Pharmaceuticals Inc | CYCLIC DIARYL ETHERS AS ANTAGONISTS OF PROSTAGLANDIN D2 RECEPTORS |
| WO2009145989A2 (en) * | 2008-04-02 | 2009-12-03 | Amira Pharmaceuticals, Inc. | Aminoalkylphenyl antagonists of prostaglandin d2 receptors |
| US8383654B2 (en) | 2008-11-17 | 2013-02-26 | Panmira Pharmaceuticals, Llc | Heterocyclic antagonists of prostaglandin D2 receptors |
| EP2567959B1 (en) | 2011-09-12 | 2014-04-16 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| US8652527B1 (en) | 2013-03-13 | 2014-02-18 | Upsher-Smith Laboratories, Inc | Extended-release topiramate capsules |
| US9101545B2 (en) | 2013-03-15 | 2015-08-11 | Upsher-Smith Laboratories, Inc. | Extended-release topiramate capsules |
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| BR0008958A (pt) * | 1999-02-23 | 2001-11-27 | Pfizer Prod Inc | Inibidores de reabsorção de monoamina para otratamento de distúrbios do snc |
| GB0007884D0 (en) * | 2000-03-31 | 2000-05-17 | Pfizer Ltd | Diphenyl ether compounds useful in therapy |
| AP2001002265A0 (en) * | 2000-08-31 | 2001-09-30 | Pfizer | Phenoxybenzylamine derivatives as SSRIs. |
| EP1831173B1 (en) * | 2004-12-17 | 2011-01-26 | Janssen Pharmaceutica NV | Tetrahydroisoquinoline compounds for treatment of cns disorders |
| CA2612495A1 (en) * | 2005-06-17 | 2006-12-28 | Janssen Pharmaceutica N.V. | Hexahydro-pyrrolo-isoquinoline compounds for the treatment of cns disorders |
| WO2006138714A2 (en) * | 2005-06-17 | 2006-12-28 | Janssen Pharmaceutica N.V. | Naphthyridine compounds |
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- 2007-06-21 CN CNA2007800323970A patent/CN101511790A/zh active Pending
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- 2007-06-21 WO PCT/US2007/071739 patent/WO2008002818A1/en not_active Ceased
- 2007-06-21 US US11/766,153 patent/US20080045508A1/en not_active Abandoned
- 2007-06-21 EP EP07798863A patent/EP2046747A1/en not_active Withdrawn
- 2007-06-21 CA CA002656083A patent/CA2656083A1/en not_active Abandoned
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