JP2009544579A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2009544579A5 JP2009544579A5 JP2009518466A JP2009518466A JP2009544579A5 JP 2009544579 A5 JP2009544579 A5 JP 2009544579A5 JP 2009518466 A JP2009518466 A JP 2009518466A JP 2009518466 A JP2009518466 A JP 2009518466A JP 2009544579 A5 JP2009544579 A5 JP 2009544579A5
- Authority
- JP
- Japan
- Prior art keywords
- piperazin
- alkyl
- phenyl
- phenoxy
- isopropyl
- 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- Withdrawn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
- -1 —OH Chemical group 0.000 claims 146
- 125000000217 alkyl group Chemical group 0.000 claims 78
- 150000001875 compounds Chemical class 0.000 claims 34
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 17
- 208000035475 disorder Diseases 0.000 claims 16
- 125000005843 halogen group Chemical group 0.000 claims 16
- 229910052757 nitrogen Inorganic materials 0.000 claims 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims 13
- 239000008194 pharmaceutical composition Substances 0.000 claims 13
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 10
- 201000010099 disease Diseases 0.000 claims 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 9
- 125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000002757 morpholinyl group Chemical group 0.000 claims 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 7
- 125000003386 piperidinyl group Chemical group 0.000 claims 7
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- 125000000304 alkynyl group Chemical group 0.000 claims 6
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 6
- 125000002950 monocyclic group Chemical group 0.000 claims 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 5
- 208000010877 cognitive disease Diseases 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 5
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims 4
- 125000005959 diazepanyl group Chemical group 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000004193 piperazinyl group Chemical group 0.000 claims 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 4
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 3
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 3
- 208000028698 Cognitive impairment Diseases 0.000 claims 3
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 3
- 125000002393 azetidinyl group Chemical group 0.000 claims 3
- 230000013016 learning Effects 0.000 claims 3
- 206010027175 memory impairment Diseases 0.000 claims 3
- 239000002207 metabolite Substances 0.000 claims 3
- 239000000651 prodrug Substances 0.000 claims 3
- 229940002612 prodrug Drugs 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 208000019116 sleep disease Diseases 0.000 claims 3
- 208000020685 sleep-wake disease Diseases 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([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
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 208000000044 Amnesia Diseases 0.000 claims 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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
- 208000026139 Memory disease 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
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 230000006735 deficit Effects 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
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 229960001340 histamine Drugs 0.000 claims 2
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 230000006984 memory degeneration Effects 0.000 claims 2
- 208000023060 memory loss Diseases 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 125000004076 pyridyl 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- SHJAEMYAMFTTLF-SFHVURJKSA-N (3s)-n,n-dimethyl-1-[3-(methylaminomethyl)-4-(4-methylsulfanylphenoxy)phenyl]pyrrolidin-3-amine Chemical compound CNCC1=CC(N2C[C@H](CC2)N(C)C)=CC=C1OC1=CC=C(SC)C=C1 SHJAEMYAMFTTLF-SFHVURJKSA-N 0.000 claims 1
- ODHBRFGOHMIIEN-UHFFFAOYSA-N (4-cyclobutylpiperazin-1-yl)-[4-(3,4-dichlorophenoxy)-3-(methylaminomethyl)phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CC2)C2CCC2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 ODHBRFGOHMIIEN-UHFFFAOYSA-N 0.000 claims 1
- WMIWAHNZDCLEIJ-UHFFFAOYSA-N (4-cyclopentylpiperazin-1-yl)-[4-(3,4-dichlorophenoxy)-3-(methylaminomethyl)phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CC2)C2CCCC2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 WMIWAHNZDCLEIJ-UHFFFAOYSA-N 0.000 claims 1
- HBSKTTXZUZBHRU-UHFFFAOYSA-N (4-cyclopropylpiperazin-1-yl)-[3-(methylaminomethyl)-4-(3-methyl-4-methylsulfanylphenoxy)phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CC2)C2CC2)=CC=C1OC1=CC=C(SC)C(C)=C1 HBSKTTXZUZBHRU-UHFFFAOYSA-N 0.000 claims 1
- BRKDRAMGEIRGGU-UHFFFAOYSA-N (4-cyclopropylpiperazin-1-yl)-[3-(methylaminomethyl)-4-(4-methylsulfanylphenoxy)phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CC2)C2CC2)=CC=C1OC1=CC=C(SC)C=C1 BRKDRAMGEIRGGU-UHFFFAOYSA-N 0.000 claims 1
- OJIYSBJEKUQECW-UHFFFAOYSA-N (4-cyclopropylpiperazin-1-yl)-[3-(methylaminomethyl)-4-(6-methylpyridin-3-yl)oxyphenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CC2)C2CC2)=CC=C1OC1=CC=C(C)N=C1 OJIYSBJEKUQECW-UHFFFAOYSA-N 0.000 claims 1
- HIZHUDHSNMVOFW-UHFFFAOYSA-N (4-cyclopropylpiperazin-1-yl)-[3-(methylaminomethyl)-4-[4-(trifluoromethyl)phenoxy]phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CC2)C2CC2)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 HIZHUDHSNMVOFW-UHFFFAOYSA-N 0.000 claims 1
- SYZMKZBTICLWQD-UHFFFAOYSA-N (4-cyclopropylpiperazin-1-yl)-[3-(methylaminomethyl)-4-phenoxyphenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CC2)C2CC2)=CC=C1OC1=CC=CC=C1 SYZMKZBTICLWQD-UHFFFAOYSA-N 0.000 claims 1
- VRRWISWZKACDCG-UHFFFAOYSA-N (4-cyclopropylpiperazin-1-yl)-[3-(methylaminomethyl)-4-pyridin-2-ylsulfanylphenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CC2)C2CC2)=CC=C1SC1=CC=CC=N1 VRRWISWZKACDCG-UHFFFAOYSA-N 0.000 claims 1
- IQTQCARYEGTKTA-UHFFFAOYSA-N (4-cyclopropylpiperazin-1-yl)-[3-(methylaminomethyl)-4-pyridin-3-yloxyphenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CC2)C2CC2)=CC=C1OC1=CC=CN=C1 IQTQCARYEGTKTA-UHFFFAOYSA-N 0.000 claims 1
- SBAQYPMYNRQKBF-UHFFFAOYSA-N (4-cyclopropylpiperazin-1-yl)-[4-(3,4-dichlorophenoxy)-3-(methylaminomethyl)phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CC2)C2CC2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 SBAQYPMYNRQKBF-UHFFFAOYSA-N 0.000 claims 1
- CNAHRPLBYREXJE-UHFFFAOYSA-N (4-cyclopropylpiperazin-1-yl)-[4-(3-fluorophenoxy)-3-(methylaminomethyl)phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CC2)C2CC2)=CC=C1OC1=CC=CC(F)=C1 CNAHRPLBYREXJE-UHFFFAOYSA-N 0.000 claims 1
- SXCDCSQBMCNNTP-UHFFFAOYSA-N (4-cyclopropylpiperazin-1-yl)-[4-(4-fluorophenoxy)-3-(methylaminomethyl)phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CC2)C2CC2)=CC=C1OC1=CC=C(F)C=C1 SXCDCSQBMCNNTP-UHFFFAOYSA-N 0.000 claims 1
- GWFWRDRCJBZYHI-UHFFFAOYSA-N (4-cyclopropylpiperazin-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)CCN1C1CC1 GWFWRDRCJBZYHI-UHFFFAOYSA-N 0.000 claims 1
- PLNZNJYRHDOZLK-UHFFFAOYSA-N (4-cyclopropylpiperazin-1-yl)-[4-[(3,4-dichlorophenyl)methoxy]-3-(methylaminomethyl)phenyl]methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CC2)C2CC2)=CC=C1OCC1=CC=C(Cl)C(Cl)=C1 PLNZNJYRHDOZLK-UHFFFAOYSA-N 0.000 claims 1
- KFUJQVSCCRBVQH-UHFFFAOYSA-N (4-cyclopropylpiperazin-1-yl)-[4-[(dimethylamino)methyl]-3-(2,6-dimethylpyridin-3-yl)oxyphenyl]methanone Chemical compound CN(C)CC1=CC=C(C(=O)N2CCN(CC2)C2CC2)C=C1OC1=CC=C(C)N=C1C KFUJQVSCCRBVQH-UHFFFAOYSA-N 0.000 claims 1
- SHYYOZRMJMQCFK-UHFFFAOYSA-N (4-cyclopropylpiperazin-1-yl)-[4-[(dimethylamino)methyl]-3-phenylmethoxyphenyl]methanone Chemical compound CN(C)CC1=CC=C(C(=O)N2CCN(CC2)C2CC2)C=C1OCC1=CC=CC=C1 SHYYOZRMJMQCFK-UHFFFAOYSA-N 0.000 claims 1
- QPPLBCQXWDBQFS-UHFFFAOYSA-N 1,4-diazepan-5-one Chemical compound O=C1CCNCCN1 QPPLBCQXWDBQFS-UHFFFAOYSA-N 0.000 claims 1
- MXPCUQVFTZJROI-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(4-propan-2-yl-1,4-diazepan-1-yl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(N2CCN(CCC2)C(C)C)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 MXPCUQVFTZJROI-UHFFFAOYSA-N 0.000 claims 1
- PMHAELGPMBNQOW-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(4-propan-2-ylpiperazin-1-yl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(N2CCN(CC2)C(C)C)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 PMHAELGPMBNQOW-UHFFFAOYSA-N 0.000 claims 1
- AXKJNMSJKGUNPA-UHFFFAOYSA-N 1-[3-(methylaminomethyl)-4-(4-methylsulfanylphenoxy)phenyl]-4-propan-2-ylpiperazin-2-one Chemical compound CNCC1=CC(N2C(CN(CC2)C(C)C)=O)=CC=C1OC1=CC=C(SC)C=C1 AXKJNMSJKGUNPA-UHFFFAOYSA-N 0.000 claims 1
- TZPXBUZPQMUJKZ-UHFFFAOYSA-N 1-[3-(methylaminomethyl)-4-(4-methylsulfanylphenoxy)phenyl]piperazin-2-one Chemical compound CNCC1=CC(N2C(CNCC2)=O)=CC=C1OC1=CC=C(SC)C=C1 TZPXBUZPQMUJKZ-UHFFFAOYSA-N 0.000 claims 1
- VIXFDDKMIWAIQH-UHFFFAOYSA-N 1-[4-(3,4-dichlorophenoxy)-3-(methylaminomethyl)phenyl]-4-propan-2-ylpiperazin-2-one Chemical compound CNCC1=CC(N2C(CN(CC2)C(C)C)=O)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 VIXFDDKMIWAIQH-UHFFFAOYSA-N 0.000 claims 1
- IBYQNSXLSJWWKR-UHFFFAOYSA-N 1-[5-(4-cyclobutylpiperazin-1-yl)-2-(4-methylsulfanylphenoxy)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(N2CCN(CC2)C2CCC2)=CC=C1OC1=CC=C(SC)C=C1 IBYQNSXLSJWWKR-UHFFFAOYSA-N 0.000 claims 1
- JWLDPMWTMOGTKS-UHFFFAOYSA-N 1-[5-(4-cyclopropyl-1,4-diazepan-1-yl)-2-(3,4-dichlorophenoxy)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 JWLDPMWTMOGTKS-UHFFFAOYSA-N 0.000 claims 1
- ZBGFYTGCXBBWEE-UHFFFAOYSA-N 1-[5-(4-cyclopropyl-1,4-diazepan-1-yl)-2-(4-methylsulfanylphenoxy)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(N2CCN(CCC2)C2CC2)=CC=C1OC1=CC=C(SC)C=C1 ZBGFYTGCXBBWEE-UHFFFAOYSA-N 0.000 claims 1
- CBFYWHDVQMGTDV-UHFFFAOYSA-N 1-[5-[4-(2-fluoroethyl)piperazin-1-yl]-2-(4-methylsulfanylphenoxy)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(N2CCN(CCF)CC2)=CC=C1OC1=CC=C(SC)C=C1 CBFYWHDVQMGTDV-UHFFFAOYSA-N 0.000 claims 1
- JLSNFHBQGVDZNW-UHFFFAOYSA-N 1-[[4-(3,4-dichlorophenoxy)-3-(methylaminomethyl)phenyl]methyl]-4-propan-2-yl-1,4-diazepan-5-one Chemical compound C=1C=C(OC=2C=C(Cl)C(Cl)=CC=2)C(CNC)=CC=1CN1CCN(C(C)C)C(=O)CC1 JLSNFHBQGVDZNW-UHFFFAOYSA-N 0.000 claims 1
- JOJPXECPTQEWRK-UHFFFAOYSA-N 1-[[4-(3,4-dichlorophenoxy)-3-(methylaminomethyl)phenyl]methyl]-4-propan-2-ylpiperazin-2-one Chemical compound C=1C=C(OC=2C=C(Cl)C(Cl)=CC=2)C(CNC)=CC=1CN1CCN(C(C)C)CC1=O JOJPXECPTQEWRK-UHFFFAOYSA-N 0.000 claims 1
- DVSJHGSUFNBLTE-UHFFFAOYSA-N 1-cyclobutyl-4-[[4-(3,4-dichlorophenoxy)-3-(methylaminomethyl)phenyl]methyl]-1,4-diazepan-5-one Chemical compound C=1C=C(OC=2C=C(Cl)C(Cl)=CC=2)C(CNC)=CC=1CN(C(CC1)=O)CCN1C1CCC1 DVSJHGSUFNBLTE-UHFFFAOYSA-N 0.000 claims 1
- LYDJKNWNWFDLAL-UHFFFAOYSA-N 1-cyclopropyl-4-[3-(methylaminomethyl)-4-(4-methylsulfanylphenoxy)phenyl]-1,4-diazepan-5-one Chemical compound CNCC1=CC(N2C(CCN(CC2)C2CC2)=O)=CC=C1OC1=CC=C(SC)C=C1 LYDJKNWNWFDLAL-UHFFFAOYSA-N 0.000 claims 1
- XEGFJPJTBTYPNB-UHFFFAOYSA-N 1-propan-2-yl-1,4-diazepane Chemical compound CC(C)N1CCCNCC1 XEGFJPJTBTYPNB-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
- 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
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[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
- 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
- YVPJWBIFPNWSEI-UHFFFAOYSA-N 4-(3-chlorophenoxy)-3-(methylaminomethyl)-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound CNCC1=CC(C(=O)NCCN2CCCC2)=CC=C1OC1=CC=CC(Cl)=C1 YVPJWBIFPNWSEI-UHFFFAOYSA-N 0.000 claims 1
- VGWUNHLDBUYHOC-UHFFFAOYSA-N 4-(3-chlorophenoxy)-n-[2-(dimethylamino)ethyl]-3-(methylaminomethyl)benzamide Chemical compound CNCC1=CC(C(=O)NCCN(C)C)=CC=C1OC1=CC=CC(Cl)=C1 VGWUNHLDBUYHOC-UHFFFAOYSA-N 0.000 claims 1
- CHJGVHYUTFKJKN-UHFFFAOYSA-N 4-(3-chlorophenoxy)-n-[3-(dimethylamino)propyl]-3-(methylaminomethyl)benzamide Chemical compound CNCC1=CC(C(=O)NCCCN(C)C)=CC=C1OC1=CC=CC(Cl)=C1 CHJGVHYUTFKJKN-UHFFFAOYSA-N 0.000 claims 1
- KGVBKLYECYPAHV-UHFFFAOYSA-N 4-[(dimethylamino)methyl]-n-[2-(methylamino)ethyl]-3-pyridin-3-yloxybenzamide Chemical compound CNCCNC(=O)C1=CC=C(CN(C)C)C(OC=2C=NC=CC=2)=C1 KGVBKLYECYPAHV-UHFFFAOYSA-N 0.000 claims 1
- PHZXWTFXAYSYEH-UHFFFAOYSA-N 4-[3-(methylaminomethyl)-4-(4-methylsulfanylphenoxy)phenyl]-1-propan-2-yl-1,4-diazepan-5-one Chemical compound CNCC1=CC(N2C(CCN(CC2)C(C)C)=O)=CC=C1OC1=CC=C(SC)C=C1 PHZXWTFXAYSYEH-UHFFFAOYSA-N 0.000 claims 1
- XRYNRKPSHZEOEG-UHFFFAOYSA-N 4-[4-(3,4-dichlorophenoxy)-3-(methylaminomethyl)phenyl]-1-propan-2-yl-1,4-diazepan-5-one Chemical compound CNCC1=CC(N2C(CCN(CC2)C(C)C)=O)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 XRYNRKPSHZEOEG-UHFFFAOYSA-N 0.000 claims 1
- VOPDSCUCPZZSKP-UHFFFAOYSA-N 4-[[4-(3,4-dichlorophenoxy)-3-(methylaminomethyl)phenyl]methyl]-1-propan-2-ylpiperazin-2-one Chemical compound C=1C=C(OC=2C=C(Cl)C(Cl)=CC=2)C(CNC)=CC=1CN1CCN(C(C)C)C(=O)C1 VOPDSCUCPZZSKP-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
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 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
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 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
- MWSAJBYJAWJUAG-UHFFFAOYSA-N C(C)(C)N1CCN(CC1)C=1C=CC(=C(CNC)C1)OC1=CC=C(C=C1)SC.C1(CC1)N1CCN(CC1)C(=O)C1=CC(=C(C=C1)CNC)OC1=CC(=C(C=C1)Cl)Cl Chemical compound C(C)(C)N1CCN(CC1)C=1C=CC(=C(CNC)C1)OC1=CC=C(C=C1)SC.C1(CC1)N1CCN(CC1)C(=O)C1=CC(=C(C=C1)CNC)OC1=CC(=C(C=C1)Cl)Cl MWSAJBYJAWJUAG-UHFFFAOYSA-N 0.000 claims 1
- OFPZUICUOZFCKG-UHFFFAOYSA-N C1(CC1)N1CCN(CC1)C=1C=CC(=C(CNC)C1)OC1=CC(=C(C=C1)Cl)Cl.C1(CC1)N1CCN(CC1)C=1C=CC(=C(CNC)C1)OC1=CC=C(C=C1)SC Chemical compound C1(CC1)N1CCN(CC1)C=1C=CC(=C(CNC)C1)OC1=CC(=C(C=C1)Cl)Cl.C1(CC1)N1CCN(CC1)C=1C=CC(=C(CNC)C1)OC1=CC=C(C=C1)SC OFPZUICUOZFCKG-UHFFFAOYSA-N 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
- 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
- COXHURHVNCVNPO-UHFFFAOYSA-N [2-(4-methylsulfanylphenoxy)-5-[(4-propan-2-ylpiperazin-1-yl)methyl]phenyl]methanamine Chemical compound C1=CC(SC)=CC=C1OC(C(=C1)CN)=CC=C1CN1CCN(C(C)C)CC1 COXHURHVNCVNPO-UHFFFAOYSA-N 0.000 claims 1
- NCZVUVFHQXGHRX-UHFFFAOYSA-N [3-(2,6-dimethylpyridin-3-yl)oxy-4-(morpholin-4-ylmethyl)phenyl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C(C=C1OC=2C(=NC(C)=CC=2)C)=CC=C1CN1CCOCC1 NCZVUVFHQXGHRX-UHFFFAOYSA-N 0.000 claims 1
- ILMKHVIQVWPTAB-UHFFFAOYSA-N [3-(3,4-dichlorophenoxy)-4-(methylaminomethyl)phenyl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound CNCC1=CC=C(C(=O)N2CCN(CC2)C(C)C)C=C1OC1=CC=C(Cl)C(Cl)=C1 ILMKHVIQVWPTAB-UHFFFAOYSA-N 0.000 claims 1
- GEZJWWSKBODYLW-UHFFFAOYSA-N [3-(3-chlorophenoxy)-4-(methylaminomethyl)phenyl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound CNCC1=CC=C(C(=O)N2CCN(CC2)C(C)C)C=C1OC1=CC=CC(Cl)=C1 GEZJWWSKBODYLW-UHFFFAOYSA-N 0.000 claims 1
- VGKDAUJYKXJXDH-UHFFFAOYSA-N [3-(4-chlorophenoxy)-4-(methylaminomethyl)phenyl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound CNCC1=CC=C(C(=O)N2CCN(CC2)C(C)C)C=C1OC1=CC=C(Cl)C=C1 VGKDAUJYKXJXDH-UHFFFAOYSA-N 0.000 claims 1
- KMKQJKLVRUKMOJ-UHFFFAOYSA-N [3-(dimethylamino)pyrrolidin-1-yl]-[4-(piperidin-1-ylmethyl)-3-pyridin-3-yloxyphenyl]methanone Chemical compound C1C(N(C)C)CCN1C(=O)C(C=C1OC=2C=NC=CC=2)=CC=C1CN1CCCCC1 KMKQJKLVRUKMOJ-UHFFFAOYSA-N 0.000 claims 1
- YIRWGCANORBOOM-UHFFFAOYSA-N [3-(methylaminomethyl)-4-(3-methyl-4-methylsulfanylphenoxy)phenyl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CC2)C(C)C)=CC=C1OC1=CC=C(SC)C(C)=C1 YIRWGCANORBOOM-UHFFFAOYSA-N 0.000 claims 1
- MZPSKPFIILGTTJ-UHFFFAOYSA-N [3-(methylaminomethyl)-4-(4-methylsulfanylphenoxy)phenyl]-(4-morpholin-4-ylpiperidin-1-yl)methanone Chemical compound CNCC1=CC(C(=O)N2CCC(CC2)N2CCOCC2)=CC=C1OC1=CC=C(SC)C=C1 MZPSKPFIILGTTJ-UHFFFAOYSA-N 0.000 claims 1
- HZRDBNNJLUYHJA-UHFFFAOYSA-N [3-(methylaminomethyl)-4-(4-methylsulfanylphenoxy)phenyl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CC2)C(C)C)=CC=C1OC1=CC=C(SC)C=C1 HZRDBNNJLUYHJA-UHFFFAOYSA-N 0.000 claims 1
- YCJMIRPXUUOVHI-UHFFFAOYSA-N [3-(methylaminomethyl)-4-[4-(trifluoromethyl)pyridin-2-yl]sulfanylphenyl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CC2)C(C)C)=CC=C1SC1=CC(C(F)(F)F)=CC=N1 YCJMIRPXUUOVHI-UHFFFAOYSA-N 0.000 claims 1
- KIGQYCHMMUGRRT-UHFFFAOYSA-N [3-(methylaminomethyl)-4-pyridin-3-yloxyphenyl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CC2)C(C)C)=CC=C1OC1=CC=CN=C1 KIGQYCHMMUGRRT-UHFFFAOYSA-N 0.000 claims 1
- JLMGYQRHFXQNCP-UHFFFAOYSA-N [3-[(cyclopropylamino)methyl]-4-pyridin-3-yloxyphenyl]-(4-cyclopropylpiperazin-1-yl)methanone Chemical compound C=1C=C(OC=2C=NC=CC=2)C(CNC2CC2)=CC=1C(=O)N(CC1)CCN1C1CC1 JLMGYQRHFXQNCP-UHFFFAOYSA-N 0.000 claims 1
- ZCEILYSPROPKSD-UHFFFAOYSA-N [3-[(cyclopropylamino)methyl]-4-pyridin-3-yloxyphenyl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C(C=C1CNC2CC2)=CC=C1OC1=CC=CN=C1 ZCEILYSPROPKSD-UHFFFAOYSA-N 0.000 claims 1
- IOKYKJVVVGGLCG-UHFFFAOYSA-N [3-phenoxy-4-[(4-propan-2-ylpiperazin-1-yl)methyl]phenyl]-piperidin-1-ylmethanone Chemical compound C1CN(C(C)C)CCN1CC1=CC=C(C(=O)N2CCCCC2)C=C1OC1=CC=CC=C1 IOKYKJVVVGGLCG-UHFFFAOYSA-N 0.000 claims 1
- NZBRXUBKIJFZOJ-UHFFFAOYSA-N [4-(3,4-dichlorophenoxy)-3-(methylaminomethyl)phenyl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CC2)C(C)C)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 NZBRXUBKIJFZOJ-UHFFFAOYSA-N 0.000 claims 1
- CLENUBFLKNDUTR-UHFFFAOYSA-N [4-(3-chloro-2-fluorophenoxy)-3-(methylaminomethyl)phenyl]-(4-cyclopropylpiperazin-1-yl)methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CC2)C2CC2)=CC=C1OC1=CC=CC(Cl)=C1F CLENUBFLKNDUTR-UHFFFAOYSA-N 0.000 claims 1
- IQYGKDOLYHUFPA-UHFFFAOYSA-N [4-(3-chloro-4-fluorophenoxy)-3-(methylaminomethyl)phenyl]-(4-cyclopropylpiperazin-1-yl)methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CC2)C2CC2)=CC=C1OC1=CC=C(F)C(Cl)=C1 IQYGKDOLYHUFPA-UHFFFAOYSA-N 0.000 claims 1
- UYXHAJGILMDGEM-UHFFFAOYSA-N [4-(3-chlorophenoxy)-3-(methylaminomethyl)phenyl]-(4-cyclobutylpiperazin-1-yl)methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CC2)C2CCC2)=CC=C1OC1=CC=CC(Cl)=C1 UYXHAJGILMDGEM-UHFFFAOYSA-N 0.000 claims 1
- AHWDVVJQAVERCT-UHFFFAOYSA-N [4-(3-chlorophenoxy)-3-(methylaminomethyl)phenyl]-(4-cyclopentylpiperazin-1-yl)methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CC2)C2CCCC2)=CC=C1OC1=CC=CC(Cl)=C1 AHWDVVJQAVERCT-UHFFFAOYSA-N 0.000 claims 1
- NWKCIVHGGAEYQL-UHFFFAOYSA-N [4-(3-chlorophenoxy)-3-(methylaminomethyl)phenyl]-(4-cyclopropylpiperazin-1-yl)methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CC2)C2CC2)=CC=C1OC1=CC=CC(Cl)=C1 NWKCIVHGGAEYQL-UHFFFAOYSA-N 0.000 claims 1
- XQRFKDJVDZKQDO-UHFFFAOYSA-N [4-(3-methoxyphenoxy)-3-(methylaminomethyl)phenyl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CC2)C(C)C)=CC=C1OC1=CC=CC(OC)=C1 XQRFKDJVDZKQDO-UHFFFAOYSA-N 0.000 claims 1
- CCMQZLXEDFXUDK-UHFFFAOYSA-N [4-(4-chloro-2-fluorophenoxy)-3-(methylaminomethyl)phenyl]-(4-cyclopropylpiperazin-1-yl)methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CC2)C2CC2)=CC=C1OC1=CC=C(Cl)C=C1F CCMQZLXEDFXUDK-UHFFFAOYSA-N 0.000 claims 1
- LKRPIMOVLOWXBL-UHFFFAOYSA-N [4-(4-chlorophenoxy)-3-(methylaminomethyl)phenyl]-(4-cyclobutylpiperazin-1-yl)methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CC2)C2CCC2)=CC=C1OC1=CC=C(Cl)C=C1 LKRPIMOVLOWXBL-UHFFFAOYSA-N 0.000 claims 1
- DWIOHHAGWJCPQF-UHFFFAOYSA-N [4-(4-chlorophenoxy)-3-(methylaminomethyl)phenyl]-(4-cyclopentylpiperazin-1-yl)methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CC2)C2CCCC2)=CC=C1OC1=CC=C(Cl)C=C1 DWIOHHAGWJCPQF-UHFFFAOYSA-N 0.000 claims 1
- RAEJZLUTUUNZSA-UHFFFAOYSA-N [4-(4-chlorophenoxy)-3-(methylaminomethyl)phenyl]-(4-cyclopropylpiperazin-1-yl)methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CC2)C2CC2)=CC=C1OC1=CC=C(Cl)C=C1 RAEJZLUTUUNZSA-UHFFFAOYSA-N 0.000 claims 1
- WZXBWZLVHBHFDT-UHFFFAOYSA-N [4-(4-chlorophenoxy)-3-(methylaminomethyl)phenyl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CC2)C(C)C)=CC=C1OC1=CC=C(Cl)C=C1 WZXBWZLVHBHFDT-UHFFFAOYSA-N 0.000 claims 1
- IKHWXPAJZVZYHU-UHFFFAOYSA-N [4-(4-chlorophenoxy)-3-[(cyclopropylamino)methyl]phenyl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C(C=C1CNC2CC2)=CC=C1OC1=CC=C(Cl)C=C1 IKHWXPAJZVZYHU-UHFFFAOYSA-N 0.000 claims 1
- WEUNWBPJZSMBEU-UHFFFAOYSA-N [4-(4-chlorophenyl)sulfanyl-3-(methylaminomethyl)phenyl]-(4-cyclopropylpiperazin-1-yl)methanone Chemical compound CNCC1=CC(C(=O)N2CCN(CC2)C2CC2)=CC=C1SC1=CC=C(Cl)C=C1 WEUNWBPJZSMBEU-UHFFFAOYSA-N 0.000 claims 1
- LFYCDFNCVIPYHZ-UHFFFAOYSA-N [4-(piperidin-1-ylmethyl)-3-pyridin-3-yloxyphenyl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C(C=C1OC=2C=NC=CC=2)=CC=C1CN1CCCCC1 LFYCDFNCVIPYHZ-UHFFFAOYSA-N 0.000 claims 1
- YOYMOCDASRCKLP-UHFFFAOYSA-N [4-[(cyclopropylamino)methyl]-3-pyridin-3-yloxyphenyl]-(4-cyclopropylpiperazin-1-yl)methanone Chemical compound C=1C=C(CNC2CC2)C(OC=2C=NC=CC=2)=CC=1C(=O)N(CC1)CCN1C1CC1 YOYMOCDASRCKLP-UHFFFAOYSA-N 0.000 claims 1
- FHBNUAOUPZCGKV-UHFFFAOYSA-N [4-[(cyclopropylamino)methyl]-3-pyridin-3-yloxyphenyl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C(C=C1OC=2C=NC=CC=2)=CC=C1CNC1CC1 FHBNUAOUPZCGKV-UHFFFAOYSA-N 0.000 claims 1
- RXAVNPOMPXETBX-UHFFFAOYSA-N [4-[(cyclopropylamino)methyl]-3-pyridin-3-yloxyphenyl]-[3-(dimethylamino)pyrrolidin-1-yl]methanone Chemical compound C1C(N(C)C)CCN1C(=O)C(C=C1OC=2C=NC=CC=2)=CC=C1CNC1CC1 RXAVNPOMPXETBX-UHFFFAOYSA-N 0.000 claims 1
- XSAKANDPMMGFMO-UHFFFAOYSA-N [4-[(dimethylamino)methyl]-3-phenoxyphenyl]-piperidin-1-ylmethanone Chemical compound CN(C)CC1=CC=C(C(=O)N2CCCCC2)C=C1OC1=CC=CC=C1 XSAKANDPMMGFMO-UHFFFAOYSA-N 0.000 claims 1
- IHYJSTACELXCAS-UHFFFAOYSA-N [4-[[bis(2-methoxyethyl)amino]methyl]-3-phenoxyphenyl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound COCCN(CCOC)CC1=CC=C(C(=O)N2CCN(CC2)C(C)C)C=C1OC1=CC=CC=C1 IHYJSTACELXCAS-UHFFFAOYSA-N 0.000 claims 1
- UYJPBPXQMFGXSL-UHFFFAOYSA-N [4-[[bis(2-methoxyethyl)amino]methyl]-3-pyridin-3-yloxyphenyl]-[4-(dimethylamino)piperidin-1-yl]methanone Chemical compound COCCN(CCOC)CC1=CC=C(C(=O)N2CCC(CC2)N(C)C)C=C1OC1=CC=CN=C1 UYJPBPXQMFGXSL-UHFFFAOYSA-N 0.000 claims 1
- 230000032683 aging Effects 0.000 claims 1
- 238000002512 chemotherapy Methods 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000000544 cholinesterase inhibitor Substances 0.000 claims 1
- 230000002060 circadian Effects 0.000 claims 1
- 230000006999 cognitive decline Effects 0.000 claims 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 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
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 208000002173 dizziness Diseases 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 239000000938 histamine H1 antagonist Substances 0.000 claims 1
- 239000003485 histamine H2 receptor antagonist Substances 0.000 claims 1
- 239000003395 histamine H3 receptor antagonist Substances 0.000 claims 1
- 230000013632 homeostatic process Effects 0.000 claims 1
- 230000003054 hormonal effect Effects 0.000 claims 1
- 206010022437 insomnia Diseases 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
- 208000002780 macular degeneration Diseases 0.000 claims 1
- 230000009245 menopause Effects 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 208000027061 mild cognitive impairment Diseases 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 229960001165 modafinil Drugs 0.000 claims 1
- 201000003152 motion sickness Diseases 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- XJDNSQODKGSPSV-UHFFFAOYSA-N n,n-dimethyl-1-[2-(4-methylsulfanylphenoxy)-5-[(4-propan-2-ylpiperazin-1-yl)methyl]phenyl]methanamine Chemical compound C1=CC(SC)=CC=C1OC(C(=C1)CN(C)C)=CC=C1CN1CCN(C(C)C)CC1 XJDNSQODKGSPSV-UHFFFAOYSA-N 0.000 claims 1
- CSPPMLXQHZZECT-UHFFFAOYSA-N n-[2-[cyclopropyl(methyl)amino]ethyl]-4-[(dimethylamino)methyl]-3-pyridin-3-yloxybenzamide Chemical compound CN(C)CC1=CC=C(C(=O)NCCN(C)C2CC2)C=C1OC1=CC=CN=C1 CSPPMLXQHZZECT-UHFFFAOYSA-N 0.000 claims 1
- UASGINNMRCXREG-UHFFFAOYSA-N n-[[2-(4-methylsulfanylphenoxy)-5-[(4-propan-2-ylpiperazin-1-yl)methyl]phenyl]methyl]cyclopropanamine Chemical compound C1=CC(SC)=CC=C1OC(C(=C1)CNC2CC2)=CC=C1CN1CCN(C(C)C)CC1 UASGINNMRCXREG-UHFFFAOYSA-N 0.000 claims 1
- IKDRGYVTJLBARP-UHFFFAOYSA-N n-[[2-(4-methylsulfanylphenoxy)-5-[(4-propan-2-ylpiperazin-1-yl)methyl]phenyl]methyl]ethanamine Chemical compound C=1C=C(OC=2C=CC(SC)=CC=2)C(CNCC)=CC=1CN1CCN(C(C)C)CC1 IKDRGYVTJLBARP-UHFFFAOYSA-N 0.000 claims 1
- ZLGKIVKSEZDTKE-UHFFFAOYSA-N n-[[2-(4-methylsulfanylphenoxy)-5-[(4-propan-2-ylpiperazin-1-yl)methyl]phenyl]methyl]propan-2-amine Chemical compound C1=CC(SC)=CC=C1OC(C(=C1)CNC(C)C)=CC=C1CN1CCN(C(C)C)CC1 ZLGKIVKSEZDTKE-UHFFFAOYSA-N 0.000 claims 1
- MLBGLHSFALOHGW-UHFFFAOYSA-N n-methyl-1-[2-(4-methylsulfanylphenoxy)-5-(4-morpholin-4-ylpiperidin-1-yl)phenyl]methanamine Chemical compound CNCC1=CC(N2CCC(CC2)N2CCOCC2)=CC=C1OC1=CC=C(SC)C=C1 MLBGLHSFALOHGW-UHFFFAOYSA-N 0.000 claims 1
- XLCFIHVFWXOWEZ-UHFFFAOYSA-N n-methyl-1-[2-(4-methylsulfanylphenoxy)-5-(4-propan-2-yl-1,4-diazepan-1-yl)phenyl]methanamine Chemical compound CNCC1=CC(N2CCN(CCC2)C(C)C)=CC=C1OC1=CC=C(SC)C=C1 XLCFIHVFWXOWEZ-UHFFFAOYSA-N 0.000 claims 1
- MZIXKAAXYDMGDK-UHFFFAOYSA-N n-methyl-1-[2-(4-methylsulfanylphenoxy)-5-(4-pyridin-4-ylpiperazin-1-yl)phenyl]methanamine Chemical compound CNCC1=CC(N2CCN(CC2)C=2C=CN=CC=2)=CC=C1OC1=CC=C(SC)C=C1 MZIXKAAXYDMGDK-UHFFFAOYSA-N 0.000 claims 1
- BNGNVHRONNZKDF-UHFFFAOYSA-N n-methyl-1-[2-(4-methylsulfanylphenoxy)-5-[(4-propan-2-ylpiperazin-1-yl)methyl]phenyl]methanamine Chemical compound C=1C=C(OC=2C=CC(SC)=CC=2)C(CNC)=CC=1CN1CCN(C(C)C)CC1 BNGNVHRONNZKDF-UHFFFAOYSA-N 0.000 claims 1
- NIFJVMMHLGJDQJ-UHFFFAOYSA-N n-methyl-1-[5-(4-methylpiperazin-1-yl)-2-(4-methylsulfanylphenoxy)phenyl]methanamine Chemical compound CNCC1=CC(N2CCN(C)CC2)=CC=C1OC1=CC=C(SC)C=C1 NIFJVMMHLGJDQJ-UHFFFAOYSA-N 0.000 claims 1
- 201000003631 narcolepsy Diseases 0.000 claims 1
- 239000002767 noradrenalin uptake inhibitor Substances 0.000 claims 1
- 229940126569 noradrenaline reuptake inhibitor Drugs 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 claims 1
- 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
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 229940127557 pharmaceutical product Drugs 0.000 claims 1
- FMHVMKQCQDBRRA-UHFFFAOYSA-N piperidin-1-yl-[4-[(4-propan-2-ylpiperazin-1-yl)methyl]-3-pyridin-3-yloxyphenyl]methanone Chemical compound C1CN(C(C)C)CCN1CC1=CC=C(C(=O)N2CCCCC2)C=C1OC1=CC=CN=C1 FMHVMKQCQDBRRA-UHFFFAOYSA-N 0.000 claims 1
- 208000028173 post-traumatic stress disease Diseases 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 201000010634 retinitis pigmentosa 38 Diseases 0.000 claims 1
- 230000033764 rhythmic process Effects 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 239000003775 serotonin noradrenalin reuptake inhibitor Substances 0.000 claims 1
- 201000002859 sleep apnea Diseases 0.000 claims 1
- 230000037321 sleepiness Effects 0.000 claims 1
- 201000009032 substance abuse Diseases 0.000 claims 1
- 231100000736 substance abuse Toxicity 0.000 claims 1
- 208000011117 substance-related disease Diseases 0.000 claims 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 1
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 231100000886 tinnitus Toxicity 0.000 claims 1
- 229960004394 topiramate Drugs 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80616906P | 2006-06-29 | 2006-06-29 | |
| PCT/US2007/071742 WO2008002820A2 (en) | 2006-06-29 | 2007-06-21 | Substituted benzyl amine compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009544579A JP2009544579A (ja) | 2009-12-17 |
| JP2009544579A5 true JP2009544579A5 (https=) | 2010-08-05 |
Family
ID=38659265
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009518466A Withdrawn JP2009544579A (ja) | 2006-06-29 | 2007-06-21 | 置換ベンジルアミン化合物 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US7479493B2 (https=) |
| EP (1) | EP2049473A2 (https=) |
| JP (1) | JP2009544579A (https=) |
| CN (1) | CN101511785A (https=) |
| AU (1) | AU2007265242A1 (https=) |
| CA (1) | CA2656089A1 (https=) |
| WO (1) | WO2008002820A2 (https=) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| WO2009119528A1 (ja) * | 2008-03-24 | 2009-10-01 | 武田薬品工業株式会社 | 複素環化合物 |
| WO2009143404A1 (en) * | 2008-05-23 | 2009-11-26 | Wyeth | Piperazine metabotropic glutamate receptor 5 (mglur5) negative allosteric modulators for anxiety/depression |
| AR074466A1 (es) | 2008-12-05 | 2011-01-19 | Sanofi Aventis | Piperidina espiro pirrolidinona y piperidinona sustituidas y su uso terapeutico en enfermedades mediadas por la modulacion de los receptores h3. |
| AR074467A1 (es) | 2008-12-05 | 2011-01-19 | Sanofi Aventis | Tetrahidropiran espiro pirrolidinonas y piperidinonas sustituidas, composiciones farmaceuticas que las contienen y uso de las mismas en el tratamiento y/o prevencion de enfermedades del snc ,tales como alzheimer y parkinson, entre otras. |
| 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 |
| GB201416351D0 (en) * | 2014-09-16 | 2014-10-29 | Shire Internat Gmbh | Heterocyclic derivatives |
| JP2021534215A (ja) * | 2018-08-24 | 2021-12-09 | ゼニオプロ ゲーエムベーハー | 病的症状の治療における使用のための芳香族分子 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR0008958A (pt) * | 1999-02-23 | 2001-11-27 | Pfizer Prod Inc | Inibidores de reabsorção de monoamina para otratamento de distúrbios do snc |
| AP2002002481A0 (en) | 1999-10-13 | 2002-06-30 | Pfizer Prod Inc | Biaryl ether derivatives useful as monoamine reuptake inhibitors. |
| 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. |
| US20020107244A1 (en) * | 2001-02-02 | 2002-08-08 | Howard Harry R. | Combination treatment for depression |
| GB0324159D0 (en) | 2003-10-15 | 2003-11-19 | Glaxo Group Ltd | Novel compounds |
| 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 |
-
2007
- 2007-06-21 CA CA002656089A patent/CA2656089A1/en not_active Abandoned
- 2007-06-21 WO PCT/US2007/071742 patent/WO2008002820A2/en not_active Ceased
- 2007-06-21 CN CNA2007800324649A patent/CN101511785A/zh active Pending
- 2007-06-21 AU AU2007265242A patent/AU2007265242A1/en not_active Abandoned
- 2007-06-21 US US11/766,172 patent/US7479493B2/en active Active
- 2007-06-21 EP EP07798864A patent/EP2049473A2/en not_active Withdrawn
- 2007-06-21 JP JP2009518466A patent/JP2009544579A/ja not_active Withdrawn
-
2008
- 2008-12-09 US US12/330,574 patent/US20090137562A1/en not_active Abandoned
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2009544579A5 (https=) | ||
| JP2009542707A5 (https=) | ||
| JP6242855B2 (ja) | 有機化合物 | |
| JP2009542708A5 (https=) | ||
| CN104395288B (zh) | 用于治疗尤文肉瘤家族肿瘤的方法和组合物 | |
| JP2013537887A5 (https=) | ||
| JP2018530571A5 (https=) | ||
| JP2009541216A5 (https=) | ||
| US7479493B2 (en) | Substituted benzyl amine compounds | |
| JP2007531753A5 (https=) | ||
| WO2007102770A8 (en) | Gsk-3 inhibitors for the treatment of osteoporosis | |
| CA2763589A1 (en) | N,n'-diarylurea compounds and n,n'-diarylthiourea compounds as inhibitors of translation initiation | |
| HUP0202492A2 (hu) | {[(Aril-metil)-karbonil]-amino}-tiazol-származékok, eljárás előállításukra és tumorellenes hatóanyagokként történő felhasználásuk | |
| RU2009136330A (ru) | Тетрагидроизохинолиновые соединения в качестве модуляторов гистаминового н3 рецептора | |
| JPS60222472A (ja) | 新規なピペラジン誘導体および該化合物を有効成分とする医薬組成物 | |
| CN1326450A (zh) | 作为τ蛋白激酶1抑制剂的羟基黄酮衍生物 | |
| JP4800936B2 (ja) | ヒスタミンレセプターｈ３のアンタゴニスト又は逆アゴニスト及び抗生精神病又は抗うつ病剤を含んで成る組み合わせ産物、並びにそれらの抗精神薬の不都合な効果を予防する医薬を調製するための使用 | |
| CN101123954B (zh) | 抗肿瘤剂 | |
| JP2013536243A5 (https=) | ||
| JP2009542661A5 (https=) | ||
| HRP20161412T1 (hr) | Fluorirani derivati arilalkilaminokarboksamida | |
| JP2009542707A (ja) | ブチルおよびブチニルベンジルアミン化合物 | |
| JP2007533685A (ja) | 偏頭痛を治療するためのセロトニン再吸収阻害剤と組合わせたｃｇｒｐアンタゴニストの使用 | |
| ES2987503T3 (es) | Compuestos que tienen afinidad por el receptor de melatonina como agente profiláctico o terapéutico para el delirio confusional | |
| JPH10500674A (ja) | ５ｈｔ▲下１ａ▼および５ｈｔ▲下１ｄ▼拮抗薬含有組成物 |