JP2009542707A5 - - Google Patents
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- JP2009542707A5 JP2009542707A5 JP2009518463A JP2009518463A JP2009542707A5 JP 2009542707 A5 JP2009542707 A5 JP 2009542707A5 JP 2009518463 A JP2009518463 A JP 2009518463A JP 2009518463 A JP2009518463 A JP 2009518463A JP 2009542707 A5 JP2009542707 A5 JP 2009542707A5
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- JP
- Japan
- Prior art keywords
- alkyl
- methyl
- substituted
- group
- ynyl
- 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.)
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- -1 —OH Chemical group 0.000 claims 134
- 125000000217 alkyl group Chemical group 0.000 claims 122
- 150000001875 compounds Chemical class 0.000 claims 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 27
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 26
- 125000005843 halogen group Chemical group 0.000 claims 25
- 125000004093 cyano group Chemical group *C#N 0.000 claims 19
- 229910052757 nitrogen Inorganic materials 0.000 claims 18
- 208000035475 disorder Diseases 0.000 claims 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 14
- 239000008194 pharmaceutical composition Substances 0.000 claims 12
- 125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 11
- 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
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 10
- 125000003342 alkenyl group Chemical group 0.000 claims 9
- 125000000304 alkynyl group Chemical group 0.000 claims 9
- 125000002950 monocyclic group Chemical group 0.000 claims 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 8
- 125000002757 morpholinyl group Chemical group 0.000 claims 7
- 125000003386 piperidinyl group Chemical group 0.000 claims 7
- 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
- 125000001153 fluoro group Chemical group F* 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 208000010877 cognitive disease Diseases 0.000 claims 5
- 125000000719 pyrrolidinyl 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
- 239000002207 metabolite Substances 0.000 claims 4
- 239000000651 prodrug Substances 0.000 claims 4
- 229940002612 prodrug Drugs 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 208000028698 Cognitive impairment Diseases 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 3
- 125000002393 azetidinyl 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
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 3
- 230000013016 learning Effects 0.000 claims 3
- 206010027175 memory impairment Diseases 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 125000004076 pyridyl group Chemical group 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
- 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
- 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
- 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
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 230000006735 deficit Effects 0.000 claims 2
- 125000005959 diazepanyl group Chemical group 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
- 238000009472 formulation Methods 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
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 229940127557 pharmaceutical product Drugs 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
- DUKRHXPXPYNWKN-UHFFFAOYSA-N 1-[2-(2-chloro-4-fluorophenoxy)-5-(4-morpholin-4-ylbut-1-ynyl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C#CCCN2CCOCC2)=CC=C1OC1=CC=C(F)C=C1Cl DUKRHXPXPYNWKN-UHFFFAOYSA-N 0.000 claims 1
- GTLCRPKCYIDHGJ-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(4-morpholin-4-ylbut-1-ynyl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C#CCCN2CCOCC2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 GTLCRPKCYIDHGJ-UHFFFAOYSA-N 0.000 claims 1
- BQBXKSFQNZVIMG-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-(4-thiomorpholin-4-ylbut-1-ynyl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C#CCCN2CCSCC2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 BQBXKSFQNZVIMG-UHFFFAOYSA-N 0.000 claims 1
- QSADIYOOZUGQQY-UHFFFAOYSA-N 1-[2-(3,4-dichlorophenoxy)-5-[4-(4-fluoropiperidin-1-yl)but-1-ynyl]phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C#CCCN2CCC(F)CC2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 QSADIYOOZUGQQY-UHFFFAOYSA-N 0.000 claims 1
- VAICHSCZMSGKPN-UHFFFAOYSA-N 1-[2-(3-chlorophenoxy)-5-(4-morpholin-4-ylbut-1-ynyl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C#CCCN2CCOCC2)=CC=C1OC1=CC=CC(Cl)=C1 VAICHSCZMSGKPN-UHFFFAOYSA-N 0.000 claims 1
- SYDKBCVMFJSWKD-UHFFFAOYSA-N 1-[2-(3-fluorophenoxy)-5-(4-morpholin-4-ylbut-1-ynyl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C#CCCN2CCOCC2)=CC=C1OC1=CC=CC(F)=C1 SYDKBCVMFJSWKD-UHFFFAOYSA-N 0.000 claims 1
- AGFIIERRTNLUMS-UHFFFAOYSA-N 1-[2-(4-chlorophenoxy)-5-(4-morpholin-4-ylbut-1-ynyl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C#CCCN2CCOCC2)=CC=C1OC1=CC=C(Cl)C=C1 AGFIIERRTNLUMS-UHFFFAOYSA-N 0.000 claims 1
- BMHXXIGOMMABCD-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)sulfanyl-5-(4-morpholin-4-ylbut-1-ynyl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C#CCCN2CCOCC2)=CC=C1SC1=CC=C(Cl)C=C1 BMHXXIGOMMABCD-UHFFFAOYSA-N 0.000 claims 1
- MFLUAACJGOHFDP-UHFFFAOYSA-N 1-[2-[4-chloro-3-(trifluoromethyl)phenoxy]-5-(4-morpholin-4-ylbut-1-ynyl)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C#CCCN2CCOCC2)=CC=C1OC1=CC=C(Cl)C(C(F)(F)F)=C1 MFLUAACJGOHFDP-UHFFFAOYSA-N 0.000 claims 1
- NLDYNKODZYDSNC-UHFFFAOYSA-N 1-[5-[4-(4-cyclopropylpiperazin-1-yl)but-1-ynyl]-2-(4-methylsulfanylphenoxy)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C#CCCN2CCN(CC2)C2CC2)=CC=C1OC1=CC=C(SC)C=C1 NLDYNKODZYDSNC-UHFFFAOYSA-N 0.000 claims 1
- KSRMXPIAWHFMID-UHFFFAOYSA-N 1-[5-[4-(4-cyclopropylpiperazin-1-yl)butyl]-2-(4-methylsulfanylphenoxy)phenyl]-n-methylmethanamine Chemical compound C=1C=C(OC=2C=CC(SC)=CC=2)C(CNC)=CC=1CCCCN(CC1)CCN1C1CC1 KSRMXPIAWHFMID-UHFFFAOYSA-N 0.000 claims 1
- YKCOYIKIANOWTN-UHFFFAOYSA-N 1-[5-[4-(4-fluoropiperidin-1-yl)but-1-ynyl]-2-(4-methylsulfanylphenoxy)phenyl]-n-methylmethanamine Chemical compound CNCC1=CC(C#CCCN2CCC(F)CC2)=CC=C1OC1=CC=C(SC)C=C1 YKCOYIKIANOWTN-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
- 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
- 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
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- UTVHDSOXYJJRDY-UHFFFAOYSA-N 4-[4-[3-(methylaminomethyl)-4-(4-methylsulfanylphenoxy)phenyl]but-3-ynyl]-1-propan-2-ylpiperazin-2-one Chemical compound CNCC1=CC(C#CCCN2CC(=O)N(C(C)C)CC2)=CC=C1OC1=CC=C(SC)C=C1 UTVHDSOXYJJRDY-UHFFFAOYSA-N 0.000 claims 1
- HAOCEOSCGBBHFB-UHFFFAOYSA-N 4-[4-[3-(methylaminomethyl)-4-(4-methylsulfanylphenoxy)phenyl]but-3-ynyl]piperazin-2-one Chemical compound CNCC1=CC(C#CCCN2CC(=O)NCC2)=CC=C1OC1=CC=C(SC)C=C1 HAOCEOSCGBBHFB-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
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 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
- 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 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
- 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
- 201000001880 Sexual dysfunction Diseases 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
- 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
- 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
- 206010027599 migraine Diseases 0.000 claims 1
- 208000027061 mild cognitive impairment Diseases 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
- HAZUWABOLNYYCL-UHFFFAOYSA-N n-[4-[3-(methylaminomethyl)-4-(4-methylsulfanylphenoxy)phenyl]but-3-ynyl]cyclopropanamine Chemical compound CNCC1=CC(C#CCCNC2CC2)=CC=C1OC1=CC=C(SC)C=C1 HAZUWABOLNYYCL-UHFFFAOYSA-N 0.000 claims 1
- VTPCFOYQLMVYRO-UHFFFAOYSA-N n-[4-[4-(3,4-dichlorophenoxy)-3-(methylaminomethyl)phenyl]but-3-ynyl]-n-methylcyclopropanamine Chemical compound CNCC1=CC(C#CCCN(C)C2CC2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 VTPCFOYQLMVYRO-UHFFFAOYSA-N 0.000 claims 1
- CEQAEEYYVALJJW-UHFFFAOYSA-N n-[4-[4-(3,4-dichlorophenoxy)-3-(methylaminomethyl)phenyl]but-3-ynyl]cyclopropanamine Chemical compound CNCC1=CC(C#CCCNC2CC2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 CEQAEEYYVALJJW-UHFFFAOYSA-N 0.000 claims 1
- DBOJAJIGVBCIQO-UHFFFAOYSA-N n-[[2-(4-chlorophenoxy)-5-(4-morpholin-4-ylbut-1-ynyl)phenyl]methyl]cyclopropanamine Chemical compound C1=CC(Cl)=CC=C1OC1=CC=C(C#CCCN2CCOCC2)C=C1CNC1CC1 DBOJAJIGVBCIQO-UHFFFAOYSA-N 0.000 claims 1
- YKEWRERCWUXQJD-UHFFFAOYSA-N n-[[5-(4-morpholin-4-ylbut-1-ynyl)-2-pyridin-3-yloxyphenyl]methyl]cyclopropanamine Chemical compound C=1C=C(OC=2C=NC=CC=2)C(CNC2CC2)=CC=1C#CCCN1CCOCC1 YKEWRERCWUXQJD-UHFFFAOYSA-N 0.000 claims 1
- CEKPOGBTNDOLTR-UHFFFAOYSA-N n-cyclopropyl-n-[4-[4-(3,4-dichlorophenoxy)-3-(methylaminomethyl)phenyl]but-3-ynyl]cyclopropanamine Chemical compound CNCC1=CC(C#CCCN(C2CC2)C2CC2)=CC=C1OC1=CC=C(Cl)C(Cl)=C1 CEKPOGBTNDOLTR-UHFFFAOYSA-N 0.000 claims 1
- KUYNMYBNRQCGCC-UHFFFAOYSA-N n-methyl-1-[2-(3-methyl-4-methylsulfanylphenoxy)-5-(4-morpholin-4-ylbut-1-ynyl)phenyl]methanamine Chemical compound CNCC1=CC(C#CCCN2CCOCC2)=CC=C1OC1=CC=C(SC)C(C)=C1 KUYNMYBNRQCGCC-UHFFFAOYSA-N 0.000 claims 1
- OARTTZNTSJLCDS-UHFFFAOYSA-N n-methyl-1-[2-(4-methylsulfanylphenoxy)-4-(4-morpholin-4-ylbut-1-ynyl)phenyl]methanamine Chemical compound CNCC1=CC=C(C#CCCN2CCOCC2)C=C1OC1=CC=C(SC)C=C1 OARTTZNTSJLCDS-UHFFFAOYSA-N 0.000 claims 1
- DYUSEVKSEDICGM-UHFFFAOYSA-N n-methyl-1-[2-(4-methylsulfanylphenoxy)-5-(4-morpholin-4-ylbut-1-ynyl)phenyl]methanamine Chemical compound CNCC1=CC(C#CCCN2CCOCC2)=CC=C1OC1=CC=C(SC)C=C1 DYUSEVKSEDICGM-UHFFFAOYSA-N 0.000 claims 1
- WTAQICPSTMPTOD-UHFFFAOYSA-N n-methyl-1-[2-(4-methylsulfanylphenoxy)-5-(4-piperidin-1-ylbut-1-ynyl)phenyl]methanamine Chemical compound CNCC1=CC(C#CCCN2CCCCC2)=CC=C1OC1=CC=C(SC)C=C1 WTAQICPSTMPTOD-UHFFFAOYSA-N 0.000 claims 1
- KECSEMPMGDAAQZ-UHFFFAOYSA-N n-methyl-1-[2-(4-methylsulfanylphenoxy)-5-(4-thiomorpholin-4-ylbut-1-ynyl)phenyl]methanamine Chemical compound CNCC1=CC(C#CCCN2CCSCC2)=CC=C1OC1=CC=C(SC)C=C1 KECSEMPMGDAAQZ-UHFFFAOYSA-N 0.000 claims 1
- JVYJGMIWWGWCJQ-UHFFFAOYSA-N n-methyl-1-[2-(4-methylsulfanylphenoxy)-5-(4-thiomorpholin-4-ylbutyl)phenyl]methanamine Chemical compound C=1C=C(OC=2C=CC(SC)=CC=2)C(CNC)=CC=1CCCCN1CCSCC1 JVYJGMIWWGWCJQ-UHFFFAOYSA-N 0.000 claims 1
- MKSDMOQTAOJLSE-UHFFFAOYSA-N n-methyl-1-[2-(4-methylsulfanylphenoxy)-5-[4-(4-propan-2-yl-1,4-diazepan-1-yl)but-1-ynyl]phenyl]methanamine Chemical compound CNCC1=CC(C#CCCN2CCN(CCC2)C(C)C)=CC=C1OC1=CC=C(SC)C=C1 MKSDMOQTAOJLSE-UHFFFAOYSA-N 0.000 claims 1
- BJWZNXSSJMLUNB-UHFFFAOYSA-N n-methyl-1-[2-(4-methylsulfanylphenoxy)-5-[4-(4-propan-2-ylpiperazin-1-yl)but-1-ynyl]phenyl]methanamine Chemical compound CNCC1=CC(C#CCCN2CCN(CC2)C(C)C)=CC=C1OC1=CC=C(SC)C=C1 BJWZNXSSJMLUNB-UHFFFAOYSA-N 0.000 claims 1
- OITIJKINXHWSKF-UHFFFAOYSA-N n-methyl-1-[2-(4-methylsulfanylphenoxy)-5-[4-(4-propan-2-ylpiperazin-1-yl)butyl]phenyl]methanamine Chemical compound C=1C=C(OC=2C=CC(SC)=CC=2)C(CNC)=CC=1CCCCN1CCN(C(C)C)CC1 OITIJKINXHWSKF-UHFFFAOYSA-N 0.000 claims 1
- GMVKCERWOQSJRI-UHFFFAOYSA-N n-methyl-1-[2-(6-methylpyridin-3-yl)oxy-5-(4-morpholin-4-ylbut-1-ynyl)phenyl]methanamine Chemical compound CNCC1=CC(C#CCCN2CCOCC2)=CC=C1OC1=CC=C(C)N=C1 GMVKCERWOQSJRI-UHFFFAOYSA-N 0.000 claims 1
- RVSCXYLNWULPGJ-UHFFFAOYSA-N n-methyl-1-[5-(4-morpholin-4-ylbut-1-ynyl)-2-[4-(trifluoromethyl)phenoxy]phenyl]methanamine Chemical compound CNCC1=CC(C#CCCN2CCOCC2)=CC=C1OC1=CC=C(C(F)(F)F)C=C1 RVSCXYLNWULPGJ-UHFFFAOYSA-N 0.000 claims 1
- SBRHBZUZVJOLQE-UHFFFAOYSA-N n-methyl-1-[5-(4-morpholin-4-ylbut-1-ynyl)-2-[4-(trifluoromethyl)pyridin-2-yl]sulfanylphenyl]methanamine Chemical compound CNCC1=CC(C#CCCN2CCOCC2)=CC=C1SC1=CC(C(F)(F)F)=CC=N1 SBRHBZUZVJOLQE-UHFFFAOYSA-N 0.000 claims 1
- OICXGVDCXUDGKS-UHFFFAOYSA-N n-methyl-1-[5-(4-morpholin-4-ylbut-1-ynyl)-2-phenoxyphenyl]methanamine Chemical compound CNCC1=CC(C#CCCN2CCOCC2)=CC=C1OC1=CC=CC=C1 OICXGVDCXUDGKS-UHFFFAOYSA-N 0.000 claims 1
- PFNGKHWWSSRASV-UHFFFAOYSA-N n-methyl-1-[5-(4-morpholin-4-ylbut-1-ynyl)-2-pyridin-2-yloxyphenyl]methanamine Chemical compound CNCC1=CC(C#CCCN2CCOCC2)=CC=C1OC1=CC=CC=N1 PFNGKHWWSSRASV-UHFFFAOYSA-N 0.000 claims 1
- IEWMEQZOVYLGPP-UHFFFAOYSA-N n-methyl-1-[5-(4-morpholin-4-ylbut-1-ynyl)-2-pyridin-3-yloxyphenyl]methanamine Chemical compound CNCC1=CC(C#CCCN2CCOCC2)=CC=C1OC1=CC=CN=C1 IEWMEQZOVYLGPP-UHFFFAOYSA-N 0.000 claims 1
- FWJKAQILVAFVQQ-UHFFFAOYSA-N n-methyl-n-[4-[3-(methylaminomethyl)-4-(4-methylsulfanylphenoxy)phenyl]but-3-ynyl]cyclopropanamine Chemical compound CNCC1=CC(C#CCCN(C)C2CC2)=CC=C1OC1=CC=C(SC)C=C1 FWJKAQILVAFVQQ-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
- 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
- 201000010615 retinitis pigmentosa 40 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
- 231100000872 sexual dysfunction Toxicity 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 |
|---|---|---|---|
| US80616506P | 2006-06-29 | 2006-06-29 | |
| PCT/US2007/071735 WO2008002817A1 (en) | 2006-06-29 | 2007-06-21 | Butyl and butynyl benzyl amine compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009542707A JP2009542707A (ja) | 2009-12-03 |
| JP2009542707A5 true JP2009542707A5 (https=) | 2010-08-05 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009518463A Withdrawn JP2009542707A (ja) | 2006-06-29 | 2007-06-21 | ブチルおよびブチニルベンジルアミン化合物 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US7767666B2 (https=) |
| EP (1) | EP2049466A1 (https=) |
| JP (1) | JP2009542707A (https=) |
| CN (1) | CN101511775A (https=) |
| AU (1) | AU2007265239A1 (https=) |
| CA (1) | CA2656075A1 (https=) |
| WO (1) | WO2008002817A1 (https=) |
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| 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 |
| SG176571A1 (en) * | 2009-05-19 | 2012-01-30 | Vivia Biotech Sl | Methods for providing personalized medicine tests ex vivo for hematological neoplasms |
| 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 |
Family Cites Families (8)
| 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 |
| 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. |
| 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 |
| WO2007036781A1 (en) | 2005-09-30 | 2007-04-05 | Pfizer Products Inc. | Diphenyl ether monoamine reuptake inhibitor |
-
2007
- 2007-06-21 WO PCT/US2007/071735 patent/WO2008002817A1/en not_active Ceased
- 2007-06-21 EP EP07784495A patent/EP2049466A1/en not_active Withdrawn
- 2007-06-21 AU AU2007265239A patent/AU2007265239A1/en not_active Abandoned
- 2007-06-21 CN CNA2007800325942A patent/CN101511775A/zh active Pending
- 2007-06-21 US US11/766,151 patent/US7767666B2/en not_active Expired - Fee Related
- 2007-06-21 JP JP2009518463A patent/JP2009542707A/ja not_active Withdrawn
- 2007-06-21 CA CA002656075A patent/CA2656075A1/en not_active Abandoned
-
2010
- 2010-06-22 US US12/820,365 patent/US20100256122A1/en not_active Abandoned
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