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 (enExample) | 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 |
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|---|---|
| US (2) | US7767666B2 (enExample) |
| EP (1) | EP2049466A1 (enExample) |
| JP (1) | JP2009542707A (enExample) |
| CN (1) | CN101511775A (enExample) |
| AU (1) | AU2007265239A1 (enExample) |
| CA (1) | CA2656075A1 (enExample) |
| WO (1) | WO2008002817A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5069907B2 (ja) * | 2003-09-17 | 2012-11-07 | 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 | 縮合複素環式化合物 |
| 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 |
| AR076590A1 (es) * | 2009-05-19 | 2011-06-22 | Vivia Biotech Sl | Metodos para proveer pruebas medicinales personalizada ex vivo para neoplasmas hematologicos |
| EP2567959B1 (en) | 2011-09-12 | 2014-04-16 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| US8652527B1 (en) | 2013-03-13 | 2014-02-18 | Upsher-Smith Laboratories, Inc | Extended-release topiramate capsules |
| US9101545B2 (en) | 2013-03-15 | 2015-08-11 | Upsher-Smith Laboratories, Inc. | Extended-release topiramate capsules |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| IL144309A0 (en) | 1999-02-23 | 2002-05-23 | Pfizer Prod Inc | Monoamine reuptake inhibitors for treatment of cns disorders |
| 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 |
| 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 |
| DE602006002894D1 (de) | 2005-06-17 | 2008-11-06 | Janssen Pharmaceutica Nv | Naphthyridinverbindungen |
| US7754882B2 (en) | 2005-06-17 | 2010-07-13 | Janssen Pharmaceutica Nv | Hexahydro-pyrrolo-isoquinoline compounds |
| WO2007036781A1 (en) | 2005-09-30 | 2007-04-05 | Pfizer Products Inc. | Diphenyl ether monoamine reuptake inhibitor |
-
2007
- 2007-06-21 AU AU2007265239A patent/AU2007265239A1/en not_active Abandoned
- 2007-06-21 CN CNA2007800325942A patent/CN101511775A/zh active Pending
- 2007-06-21 JP JP2009518463A patent/JP2009542707A/ja not_active Withdrawn
- 2007-06-21 EP EP07784495A patent/EP2049466A1/en not_active Withdrawn
- 2007-06-21 US US11/766,151 patent/US7767666B2/en not_active Expired - Fee Related
- 2007-06-21 WO PCT/US2007/071735 patent/WO2008002817A1/en not_active Ceased
- 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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