JP2009544579A - 置換ベンジルアミン化合物 - Google Patents
置換ベンジルアミン化合物 Download PDFInfo
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- JP2009544579A JP2009544579A JP2009518466A JP2009518466A JP2009544579A JP 2009544579 A JP2009544579 A JP 2009544579A JP 2009518466 A JP2009518466 A JP 2009518466A JP 2009518466 A JP2009518466 A JP 2009518466A JP 2009544579 A JP2009544579 A JP 2009544579A
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- JP
- Japan
- Prior art keywords
- alkyl
- piperazin
- phenoxy
- phenyl
- 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- Withdrawn
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- 150000003939 benzylamines Chemical class 0.000 title abstract description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 72
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims abstract description 44
- 201000010099 disease Diseases 0.000 claims abstract description 31
- 102000019208 Serotonin Plasma Membrane Transport Proteins Human genes 0.000 claims abstract description 28
- 108010012996 Serotonin Plasma Membrane Transport Proteins Proteins 0.000 claims abstract description 28
- 229960001340 histamine Drugs 0.000 claims abstract description 22
- 238000011282 treatment Methods 0.000 claims abstract description 22
- 230000001404 mediated effect Effects 0.000 claims abstract description 11
- -1 —OH Chemical group 0.000 claims description 335
- 125000000217 alkyl group Chemical group 0.000 claims description 172
- 150000001875 compounds Chemical class 0.000 claims description 141
- 201000006417 multiple sclerosis Diseases 0.000 claims description 103
- 238000000034 method Methods 0.000 claims description 59
- 208000035475 disorder Diseases 0.000 claims description 41
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
- 125000005843 halogen group Chemical group 0.000 claims description 33
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 31
- 239000000651 prodrug Substances 0.000 claims description 28
- 229940002612 prodrug Drugs 0.000 claims description 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 20
- 230000000694 effects Effects 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims description 16
- 125000000304 alkynyl group Chemical group 0.000 claims description 15
- 208000010877 cognitive disease Diseases 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000002757 morpholinyl group Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000003386 piperidinyl group Chemical group 0.000 claims description 14
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 14
- 208000019116 sleep disease Diseases 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 12
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 12
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
- 239000002207 metabolite Substances 0.000 claims description 11
- 125000002950 monocyclic group Chemical group 0.000 claims description 11
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 208000028698 Cognitive impairment Diseases 0.000 claims description 8
- 206010016256 fatigue Diseases 0.000 claims description 8
- 230000013016 learning Effects 0.000 claims description 8
- 125000004193 piperazinyl group Chemical group 0.000 claims description 8
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 7
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 7
- 208000026139 Memory disease Diseases 0.000 claims description 7
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 7
- 125000005959 diazepanyl group Chemical group 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 206010041349 Somnolence Diseases 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000002393 azetidinyl group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 5
- 208000000044 Amnesia Diseases 0.000 claims description 5
- 206010024264 Lethargy Diseases 0.000 claims description 5
- 208000032140 Sleepiness Diseases 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 230000006735 deficit Effects 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 230000006984 memory degeneration Effects 0.000 claims description 5
- 206010027175 memory impairment Diseases 0.000 claims description 5
- 208000023060 memory loss Diseases 0.000 claims description 5
- 208000020016 psychiatric disease Diseases 0.000 claims description 5
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 claims description 5
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 claims description 5
- 208000020685 sleep-wake disease Diseases 0.000 claims description 5
- 230000037321 sleepiness Effects 0.000 claims description 5
- 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 description 4
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 4
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
- 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 description 4
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 4
- 206010012289 Dementia Diseases 0.000 claims description 4
- 208000030814 Eating disease Diseases 0.000 claims description 4
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 4
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 235000014632 disordered eating Nutrition 0.000 claims description 4
- 239000003395 histamine H3 receptor antagonist Substances 0.000 claims description 4
- 229960001165 modafinil Drugs 0.000 claims description 4
- 201000003631 narcolepsy Diseases 0.000 claims description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 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 description 3
- 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 description 3
- 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 description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims description 3
- 208000001456 Jet Lag Syndrome Diseases 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 208000002173 dizziness Diseases 0.000 claims description 3
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims description 3
- 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 description 3
- 201000000980 schizophrenia Diseases 0.000 claims description 3
- 208000011117 substance-related disease Diseases 0.000 claims description 3
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 2
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
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- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
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- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Chemical & Material Sciences (AREA)
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Applications Claiming Priority (2)
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| 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 |
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| JP2009544579A true JP2009544579A (ja) | 2009-12-17 |
| JP2009544579A5 JP2009544579A5 (enExample) | 2010-08-05 |
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| EA010905B1 (ru) * | 2003-09-17 | 2008-12-30 | Янссен Фармацевтика Н.В. | Сопряжённые гетероциклические соединения |
| 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 |
| US20090325964A1 (en) * | 2008-05-23 | 2009-12-31 | 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 |
| CN118290322A (zh) * | 2018-08-24 | 2024-07-05 | 赛尼欧普罗有限责任公司 | 用于治疗病态状况的芳香型分子 |
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| EE200100441A (et) * | 1999-02-23 | 2002-12-16 | Pfizer Products Inc. | Monoamiinide taasomastamise inhibiitorid kesknärvisüsteemi haiguste raviks |
| YU21602A (sh) * | 1999-10-13 | 2005-06-10 | Pfizer Products Inc. | Derivati biaril etra korisni kao inhibitori ponovnog podizanja monoamina |
| GB0007884D0 (en) * | 2000-03-31 | 2000-05-17 | Pfizer Ltd | Diphenyl ether compounds useful in therapy |
| JP2004507523A (ja) | 2000-08-31 | 2004-03-11 | ファイザー・インク | 選択的セロトニン再取込み阻害剤としてのフェノキシベンジルアミン誘導体 |
| 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 |
| ATE496892T1 (de) * | 2004-12-17 | 2011-02-15 | Janssen Pharmaceutica Nv | Tetrahydroisochinolinverbindungen zur behandlung von zns-erkrankungen |
| PL1899334T3 (pl) * | 2005-06-17 | 2009-04-30 | Janssen Pharmaceutica Nv | Związki naftyrydynowe |
| JP2008546711A (ja) * | 2005-06-17 | 2008-12-25 | 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 | Cns障害の処置のためのヘキサヒドロ−ピロロ−イソキノリン化合物 |
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2007
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2008
- 2008-12-09 US US12/330,574 patent/US20090137562A1/en not_active Abandoned
Also Published As
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| CN101511785A (zh) | 2009-08-19 |
| AU2007265242A1 (en) | 2008-01-03 |
| EP2049473A2 (en) | 2009-04-22 |
| US7479493B2 (en) | 2009-01-20 |
| CA2656089A1 (en) | 2008-01-03 |
| US20080045509A1 (en) | 2008-02-21 |
| WO2008002820A3 (en) | 2008-06-26 |
| US20090137562A1 (en) | 2009-05-28 |
| WO2008002820A2 (en) | 2008-01-03 |
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