CA2722978A1 - Modulators of dopamine neurotransmission - Google Patents
Modulators of dopamine neurotransmission Download PDFInfo
- Publication number
- CA2722978A1 CA2722978A1 CA2722978A CA2722978A CA2722978A1 CA 2722978 A1 CA2722978 A1 CA 2722978A1 CA 2722978 A CA2722978 A CA 2722978A CA 2722978 A CA2722978 A CA 2722978A CA 2722978 A1 CA2722978 A1 CA 2722978A1
- Authority
- CA
- Canada
- Prior art keywords
- dihydro
- methyl
- methylsulfonyl
- benzodioxin
- amine
- 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.)
- Abandoned
Links
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 title abstract description 37
- 229960003638 dopamine Drugs 0.000 title abstract description 18
- 230000005062 synaptic transmission Effects 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 189
- 238000000034 method Methods 0.000 claims abstract description 24
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
- 239000000203 mixture Substances 0.000 claims description 126
- 150000003839 salts Chemical class 0.000 claims description 53
- -1 3,3,3-trifluoropropyl Chemical group 0.000 claims description 48
- 150000001412 amines Chemical class 0.000 claims description 40
- 150000001204 N-oxides Chemical class 0.000 claims description 38
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 37
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 36
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 29
- 125000000623 heterocyclic group Chemical group 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 21
- 208000035475 disorder Diseases 0.000 claims description 21
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 15
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 15
- 201000010099 disease Diseases 0.000 claims description 15
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 13
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 13
- 241001465754 Metazoa Species 0.000 claims description 13
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 11
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical compound [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 10
- UHCBBWUQDAVSMS-UHFFFAOYSA-N fluoroethane Chemical compound CCF UHCBBWUQDAVSMS-UHFFFAOYSA-N 0.000 claims description 10
- 241000282414 Homo sapiens Species 0.000 claims description 9
- 208000028017 Psychotic disease Diseases 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 7
- 210000003169 central nervous system Anatomy 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical group F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 6
- 108010081348 HRT1 protein Hairy Chemical group 0.000 claims description 6
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 6
- 230000010249 dopaminergic function Effects 0.000 claims description 6
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical group F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 6
- NFLCJVNIHXOFPL-VIFPVBQESA-N n-[[(2s)-5-fluoro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl]methyl]propan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2O[C@@H](CNCCC)COC2=C1F NFLCJVNIHXOFPL-VIFPVBQESA-N 0.000 claims description 6
- 101100533877 Hypocrea jecorina (strain QM6a) sor8 gene Proteins 0.000 claims description 5
- 229910006074 SO2NH2 Inorganic materials 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims description 5
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 208000012661 Dyskinesia Diseases 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- CYBYLIMSZIVQTB-QMMMGPOBSA-N n-[[(2s)-5-fluoro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl]methyl]ethanamine Chemical compound C1=C(S(C)(=O)=O)C=C2O[C@@H](CNCC)COC2=C1F CYBYLIMSZIVQTB-QMMMGPOBSA-N 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 201000000980 schizophrenia Diseases 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- ACSYJWICJIGNLM-UHFFFAOYSA-N 1-(5-fluoro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl)-n,n-dimethylmethanamine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CN(C)C)COC2=C1F ACSYJWICJIGNLM-UHFFFAOYSA-N 0.000 claims description 3
- CCAIFRVSMWLNEE-UHFFFAOYSA-N 1-(5-fluoro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl)-n-methylmethanamine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CNC)COC2=C1F CCAIFRVSMWLNEE-UHFFFAOYSA-N 0.000 claims description 3
- NWDJQBPQRBURCK-UHFFFAOYSA-N 1-[(5-fluoro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]pyrrolidine Chemical compound O1C2=CC(S(=O)(=O)C)=CC(F)=C2OCC1CN1CCCC1 NWDJQBPQRBURCK-UHFFFAOYSA-N 0.000 claims description 3
- DRKJABUWGLAFKY-UHFFFAOYSA-N 1-[(7-methylsulfonyl-3,4-dihydro-2h-chromen-2-yl)methyl]piperidine Chemical compound O1C2=CC(S(=O)(=O)C)=CC=C2CCC1CN1CCCCC1 DRKJABUWGLAFKY-UHFFFAOYSA-N 0.000 claims description 3
- PQZPJSJBBOGKFA-UHFFFAOYSA-N 1-[(7-methylsulfonyl-3,4-dihydro-2h-chromen-2-yl)methyl]pyrrolidine Chemical compound O1C2=CC(S(=O)(=O)C)=CC=C2CCC1CN1CCCC1 PQZPJSJBBOGKFA-UHFFFAOYSA-N 0.000 claims description 3
- YMYCYPLFBJAPSA-GFCCVEGCSA-N 1-[[(3r)-6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl]methyl]piperidine Chemical compound C([C@@H]1COC2=CC=C(C=C2O1)S(=O)(=O)C)N1CCCCC1 YMYCYPLFBJAPSA-GFCCVEGCSA-N 0.000 claims description 3
- OGXFHSKZILWLNO-NSHDSACASA-N 2,2-dimethyl-n-[[(3s)-6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl]methyl]propan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2O[C@@H](CNCC(C)(C)C)COC2=C1 OGXFHSKZILWLNO-NSHDSACASA-N 0.000 claims description 3
- AYRSCENJQDTKKW-UHFFFAOYSA-N 2-[(6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl)methylamino]ethanol Chemical compound O1CC(CNCCO)OC2=CC(S(=O)(=O)C)=CC=C21 AYRSCENJQDTKKW-UHFFFAOYSA-N 0.000 claims description 3
- UFXCPZGYIFTGBV-UHFFFAOYSA-N 2-[(7-methylsulfonyl-3,4-dihydro-2h-chromen-2-yl)methylamino]ethanol Chemical compound C1CC(CNCCO)OC2=CC(S(=O)(=O)C)=CC=C21 UFXCPZGYIFTGBV-UHFFFAOYSA-N 0.000 claims description 3
- PZGIGAYLGVNPAM-UHFFFAOYSA-N 2-methoxy-n-[(6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]ethanamine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CNCCOC)COC2=C1 PZGIGAYLGVNPAM-UHFFFAOYSA-N 0.000 claims description 3
- XZLUXENLKSWQTA-UHFFFAOYSA-N 2-methyl-n-[(6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]propan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CNCC(C)C)COC2=C1 XZLUXENLKSWQTA-UHFFFAOYSA-N 0.000 claims description 3
- XZLUXENLKSWQTA-LLVKDONJSA-N 2-methyl-n-[[(3r)-6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl]methyl]propan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2O[C@H](CNCC(C)C)COC2=C1 XZLUXENLKSWQTA-LLVKDONJSA-N 0.000 claims description 3
- YNQIUDXOEYHCHG-VIFPVBQESA-N 3,3,3-trifluoro-n-[[(3s)-6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl]methyl]propan-1-amine Chemical compound O1C[C@H](CNCCC(F)(F)F)OC2=CC(S(=O)(=O)C)=CC=C21 YNQIUDXOEYHCHG-VIFPVBQESA-N 0.000 claims description 3
- HMTHTJXBHPRKIF-ZGTCLIOFSA-N 3-methyl-1-[[(3r)-6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl]methyl]piperidine Chemical compound C1C(C)CCCN1C[C@H]1OC2=CC(S(C)(=O)=O)=CC=C2OC1 HMTHTJXBHPRKIF-ZGTCLIOFSA-N 0.000 claims description 3
- QIMAGFLOKOCZDJ-UHFFFAOYSA-N 4-[(5-fluoro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]morpholine Chemical compound O1C2=CC(S(=O)(=O)C)=CC(F)=C2OCC1CN1CCOCC1 QIMAGFLOKOCZDJ-UHFFFAOYSA-N 0.000 claims description 3
- KOFNOWRXIDSMAA-UHFFFAOYSA-N 4-[(6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]morpholine Chemical compound O1C2=CC(S(=O)(=O)C)=CC=C2OCC1CN1CCOCC1 KOFNOWRXIDSMAA-UHFFFAOYSA-N 0.000 claims description 3
- JDCIBHCASSGJOB-UHFFFAOYSA-N 4-[(7-methylsulfonyl-3,4-dihydro-2h-chromen-2-yl)methyl]morpholine Chemical compound O1C2=CC(S(=O)(=O)C)=CC=C2CCC1CN1CCOCC1 JDCIBHCASSGJOB-UHFFFAOYSA-N 0.000 claims description 3
- QIMAGFLOKOCZDJ-JTQLQIEISA-N 4-[[(2s)-5-fluoro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl]methyl]morpholine Chemical compound C([C@H]1COC2=C(F)C=C(C=C2O1)S(=O)(=O)C)N1CCOCC1 QIMAGFLOKOCZDJ-JTQLQIEISA-N 0.000 claims description 3
- 208000020925 Bipolar disease Diseases 0.000 claims description 3
- 206010012289 Dementia Diseases 0.000 claims description 3
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- 208000016285 Movement disease Diseases 0.000 claims description 3
- 208000002193 Pain Diseases 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 230000000642 iatrogenic effect Effects 0.000 claims description 3
- QVVXSAIFIWLFAB-UHFFFAOYSA-N n,n-dimethyl-1-(7-methylsulfonyl-3,4-dihydro-2h-chromen-2-yl)methanamine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CN(C)C)CCC2=C1 QVVXSAIFIWLFAB-UHFFFAOYSA-N 0.000 claims description 3
- IWCVJTWXFIQFKV-UHFFFAOYSA-N n-[(5-fluoro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-2-methoxyethanamine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CNCCOC)COC2=C1F IWCVJTWXFIQFKV-UHFFFAOYSA-N 0.000 claims description 3
- JMVMQHJFSAOHCU-UHFFFAOYSA-N n-[(5-fluoro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-2-methylpropan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CNCC(C)C)COC2=C1F JMVMQHJFSAOHCU-UHFFFAOYSA-N 0.000 claims description 3
- COZAOGJDNDUOHZ-UHFFFAOYSA-N n-[(5-fluoro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-n-methylpropan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CN(C)CCC)COC2=C1F COZAOGJDNDUOHZ-UHFFFAOYSA-N 0.000 claims description 3
- HGYAEVSVNVKZRE-UHFFFAOYSA-N n-[(5-fluoro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-n-propylpropan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CN(CCC)CCC)COC2=C1F HGYAEVSVNVKZRE-UHFFFAOYSA-N 0.000 claims description 3
- IZLXMGUNKCDTRS-UHFFFAOYSA-N n-[(5-fluoro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]butan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CNCCCC)COC2=C1F IZLXMGUNKCDTRS-UHFFFAOYSA-N 0.000 claims description 3
- CYBYLIMSZIVQTB-UHFFFAOYSA-N n-[(5-fluoro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]ethanamine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CNCC)COC2=C1F CYBYLIMSZIVQTB-UHFFFAOYSA-N 0.000 claims description 3
- VPONXHJUNCZNLJ-UHFFFAOYSA-N n-[(5-fluoro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]prop-2-en-1-amine Chemical compound O1CC(CNCC=C)OC2=CC(S(=O)(=O)C)=CC(F)=C21 VPONXHJUNCZNLJ-UHFFFAOYSA-N 0.000 claims description 3
- QYNCLOCTEVTRJW-UHFFFAOYSA-N n-[(6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]butan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CNCCCC)COC2=C1 QYNCLOCTEVTRJW-UHFFFAOYSA-N 0.000 claims description 3
- XMHPZKPXIAVGLB-UHFFFAOYSA-N n-[(6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]ethanamine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CNCC)COC2=C1 XMHPZKPXIAVGLB-UHFFFAOYSA-N 0.000 claims description 3
- AUAAOFMSOHILNS-UHFFFAOYSA-N n-[(6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl)methyl]propan-2-amine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CNC(C)C)COC2=C1 AUAAOFMSOHILNS-UHFFFAOYSA-N 0.000 claims description 3
- BMVUMEMDCRNOSK-UHFFFAOYSA-N n-[(7-methylsulfonyl-3,4-dihydro-2h-chromen-2-yl)methyl]-n-propylpropan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CN(CCC)CCC)CCC2=C1 BMVUMEMDCRNOSK-UHFFFAOYSA-N 0.000 claims description 3
- JUKYRQPWRKYMEH-UHFFFAOYSA-N n-[(7-methylsulfonyl-3,4-dihydro-2h-chromen-2-yl)methyl]butan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CNCCCC)CCC2=C1 JUKYRQPWRKYMEH-UHFFFAOYSA-N 0.000 claims description 3
- WIVADSNAUYDWFY-UHFFFAOYSA-N n-[(7-methylsulfonyl-3,4-dihydro-2h-chromen-2-yl)methyl]ethanamine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CNCC)CCC2=C1 WIVADSNAUYDWFY-UHFFFAOYSA-N 0.000 claims description 3
- DPQXIDNQWGFQAA-UHFFFAOYSA-N n-[(7-methylsulfonyl-3,4-dihydro-2h-chromen-2-yl)methyl]prop-2-en-1-amine Chemical compound C1CC(CNCC=C)OC2=CC(S(=O)(=O)C)=CC=C21 DPQXIDNQWGFQAA-UHFFFAOYSA-N 0.000 claims description 3
- VLRJTIYKLYDRSN-JTQLQIEISA-N n-[[(2s)-5-chloro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl]methyl]-2,2-dimethylpropan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2O[C@@H](CNCC(C)(C)C)COC2=C1Cl VLRJTIYKLYDRSN-JTQLQIEISA-N 0.000 claims description 3
- WVGMRJOHWGRXDB-JTQLQIEISA-N n-[[(2s)-5-chloro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl]methyl]-2-methylpropan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2O[C@@H](CNCC(C)C)COC2=C1Cl WVGMRJOHWGRXDB-JTQLQIEISA-N 0.000 claims description 3
- KYUKFUXUFQAWEO-JTQLQIEISA-N n-[[(2s)-5-chloro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl]methyl]-n-ethylethanamine Chemical compound C1=C(S(C)(=O)=O)C=C2O[C@@H](CN(CC)CC)COC2=C1Cl KYUKFUXUFQAWEO-JTQLQIEISA-N 0.000 claims description 3
- OSKPEFIPFULJMA-NSHDSACASA-N n-[[(2s)-5-chloro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl]methyl]-n-ethylpropan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2O[C@@H](CN(CC)CCC)COC2=C1Cl OSKPEFIPFULJMA-NSHDSACASA-N 0.000 claims description 3
- ZZZDEINEZALERV-JTQLQIEISA-N n-[[(2s)-5-chloro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl]methyl]-n-methylpropan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2O[C@@H](CN(C)CCC)COC2=C1Cl ZZZDEINEZALERV-JTQLQIEISA-N 0.000 claims description 3
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- DENNJTQQOMENLP-VIFPVBQESA-N n-[[(2s)-5-chloro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl]methyl]propan-2-amine Chemical compound C1=C(S(C)(=O)=O)C=C2O[C@@H](CNC(C)C)COC2=C1Cl DENNJTQQOMENLP-VIFPVBQESA-N 0.000 claims description 3
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- KHWNHRMQYUBIMK-VIFPVBQESA-N n-[[(3s)-6-(trifluoromethylsulfonyl)-2,3-dihydro-1,4-benzodioxin-3-yl]methyl]propan-1-amine Chemical compound C1=C(S(=O)(=O)C(F)(F)F)C=C2O[C@@H](CNCCC)COC2=C1 KHWNHRMQYUBIMK-VIFPVBQESA-N 0.000 claims description 3
- XENWRVWPGWCBES-VIFPVBQESA-N n-[[(3s)-6-(trifluoromethylsulfonyl)-2,3-dihydro-1,4-benzodioxin-3-yl]methyl]propan-2-amine Chemical compound C1=C(S(=O)(=O)C(F)(F)F)C=C2O[C@@H](CNC(C)C)COC2=C1 XENWRVWPGWCBES-VIFPVBQESA-N 0.000 claims description 3
- XMHPZKPXIAVGLB-VIFPVBQESA-N n-[[(3s)-6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl]methyl]ethanamine Chemical compound C1=C(S(C)(=O)=O)C=C2O[C@@H](CNCC)COC2=C1 XMHPZKPXIAVGLB-VIFPVBQESA-N 0.000 claims description 3
- MAMVDUBLWPVXIQ-JTQLQIEISA-N n-[[(3s)-6-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-3-yl]methyl]propan-1-amine Chemical compound C1=C(S(C)(=O)=O)C=C2O[C@@H](CNCCC)COC2=C1 MAMVDUBLWPVXIQ-JTQLQIEISA-N 0.000 claims description 3
- JIUTZSUQHJMGKF-UHFFFAOYSA-N n-ethyl-n-[(5-fluoro-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]ethanamine Chemical compound C1=C(S(C)(=O)=O)C=C2OC(CN(CC)CC)COC2=C1F JIUTZSUQHJMGKF-UHFFFAOYSA-N 0.000 claims description 3
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/20—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 hydrogenated in the hetero ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
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- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
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- Hematology (AREA)
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- Gynecology & Obstetrics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
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| DKPA200800598 | 2008-04-29 | ||
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| US4905908P | 2008-04-30 | 2008-04-30 | |
| US61/049,059 | 2008-04-30 | ||
| PCT/EP2009/055137 WO2009133107A1 (en) | 2008-04-29 | 2009-04-28 | Modulators of dopamine neurotransmission |
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| CA2722978A1 true CA2722978A1 (en) | 2009-11-05 |
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| EP (1) | EP2271634B1 (enExample) |
| JP (1) | JP5514804B2 (enExample) |
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| EP2271635A1 (en) * | 2008-04-29 | 2011-01-12 | NSAB, Filial af NeuroSearch Sweden AB, Sverige | Modulators of dopamine neurotransmission |
| MX2010011498A (es) | 2008-04-29 | 2010-11-12 | Nsab Af Neurosearch Sweden Ab | Moduladores de neurotransmision de dopamina. |
| CN102180856B (zh) * | 2011-03-01 | 2016-01-20 | 浙江华海药业股份有限公司 | 一种制备6-氟-3,4-二氢-2h-1-苯并吡喃-2-甲酸乙酯的方法 |
| JP5876140B2 (ja) | 2011-04-19 | 2016-03-02 | インテグレイティブ・リサーチ・ラボラトリーズ・スウェーデン・アーベー | 皮質のドーパミン作動性及びｎｍｄａ受容体介在のグルタミン酸作動性神経伝達の新規なモジュレータ |
| KR20160027218A (ko) | 2012-05-23 | 2016-03-09 | 에프. 호프만-라 로슈 아게 | 내배엽 및 간세포를 수득하고 사용하는 조성물 및 방법 |
| JP6481689B2 (ja) | 2014-06-26 | 2019-03-13 | 住友化学株式会社 | フェノール化合物の製造方法 |
| US9125866B1 (en) | 2015-01-28 | 2015-09-08 | King Saud University | Antidepressant compounds |
| CH712810B1 (de) * | 2015-07-21 | 2020-07-15 | Sumitomo Chemical Co | Verfahren zur Herstellung einer 4-(Trifluormethylsulfonyl)phenol-Verbindung. |
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| DE1110175B (de) * | 1957-01-08 | 1961-07-06 | Rhone Poulenc Sa | Verfahren zur Herstellung von Benzodioxanderivaten |
| JPS55124781A (en) * | 1979-03-20 | 1980-09-26 | Shionogi & Co Ltd | 1,4-benzdioxanesulfonamide derivative |
| US5236055A (en) * | 1991-03-13 | 1993-08-17 | Canadian Aging & Rehabilitation Product Development Corporation | Wheel with coaxial drive system mounted in the wheelhub field of the invention |
| US5189171A (en) * | 1991-06-21 | 1993-02-23 | American Home Products Corporation | Antipsychotic benzodioxan derivatives |
| US5166367A (en) * | 1991-06-21 | 1992-11-24 | American Home Products Corporation | Antipsychotic benzodioxan derivatives |
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| DE4135474A1 (de) * | 1991-10-28 | 1993-04-29 | Bayer Ag | 2-aminomethyl-chromane |
| US5235055A (en) | 1992-09-02 | 1993-08-10 | American Home Products Corporation | Antipsychotic quinoline derivatives of benzodioxanmethylamine |
| US5245051A (en) * | 1992-09-03 | 1993-09-14 | American Home Products Corporation | Antipsychotic chroman derivatives of benzodioxanmethylamine |
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| US5663194A (en) * | 1995-07-25 | 1997-09-02 | Mewshaw; Richard E. | Chroman-2-ylmethylamino derivatives |
| US5684039A (en) * | 1995-07-25 | 1997-11-04 | American Home Products Corporation | Chroman-2-ylmethylamino derivatives |
| AR004229A1 (es) * | 1995-11-06 | 1998-11-04 | Wyeth Corp | Derivados indolalquilo de benzodioxanmetilamina y su uso para preparar medicamentos |
| FR2791675B1 (fr) | 1999-03-30 | 2001-05-04 | Synthelabo | Derives de n-[2-(4-aminophenyl) ethyl] -2,3-dihydro-1,4- benzodioxinne-2-methanamine, leur preparation et leur application en therapeutique |
| SE9904724D0 (sv) * | 1999-12-22 | 1999-12-22 | Carlsson A Research Ab | New modulators of dopamine neurotransmission I |
| SE9904723D0 (sv) * | 1999-12-22 | 1999-12-22 | Carlsson A Research Ab | New modulators of dopamine neurotransmission II |
| GB0007376D0 (en) | 2000-03-28 | 2000-05-17 | Knoll Ag | Therapeutic agents |
| JP2005505586A (ja) * | 2001-10-04 | 2005-02-24 | ワイス | ５−ヒドロキシトリプタミン−６リガンドとしてのクロマン誘導体 |
| TWI281470B (en) * | 2002-05-24 | 2007-05-21 | Elan Pharm Inc | Heterocyclic compounds which inhibit leukocyte adhesion mediated by alpha4 integrins |
| US20070208166A1 (en) * | 2003-10-24 | 2007-09-06 | Exelixis, Inc. | Tao Kinase Modulators And Method Of Use |
| NZ550441A (en) * | 2004-05-05 | 2009-07-31 | Hoffmann La Roche | Arylsulfonyl benzodioxanes useful for modulating the 5-HT6 receptor, the 5-HT2A receptor or both |
| KR101245075B1 (ko) * | 2004-06-08 | 2013-03-18 | 엔에스아베 필리알 아프 뉴로서치 스웨덴 아베 스베리게 | 도파민 신경전달의 모듈레이터로서 신 2기치환된페닐피페리딘/피페라진 |
| MY147767A (en) * | 2004-06-16 | 2013-01-31 | Janssen Pharmaceutica Nv | Novel sulfamate and sulfamide derivatives useful for the treatment of epilepsy and related disorders |
| TW200612905A (en) * | 2004-06-16 | 2006-05-01 | Janssen Pharmaceutica Nv | Novel sulfamate and sulfamide derivatives useful for the treatment of epilepsy and related disorders |
| US7713954B2 (en) * | 2004-09-30 | 2010-05-11 | Roche Palo Alto Llc | Compositions and methods for treating cognitive disorders |
| BRPI0610046A2 (pt) * | 2005-04-22 | 2010-05-25 | Wyeth Corp | derivados de benzodioxano e benzodioxolano e usos destes |
| SE529246C2 (sv) * | 2005-10-13 | 2007-06-12 | Neurosearch Sweden Ab | Nya disubstituerade fenyl-piperidiner som modulatorer för dopaminneurotransmission |
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| EP2271635A1 (en) | 2008-04-29 | 2011-01-12 | NSAB, Filial af NeuroSearch Sweden AB, Sverige | Modulators of dopamine neurotransmission |
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-
2009
- 2009-04-28 DK DK09738151.1T patent/DK2271634T3/da active
- 2009-04-28 EP EP09738151.1A patent/EP2271634B1/en not_active Not-in-force
- 2009-04-28 CA CA2722978A patent/CA2722978A1/en not_active Abandoned
- 2009-04-28 BR BRPI0911772A patent/BRPI0911772A2/pt not_active IP Right Cessation
- 2009-04-28 NZ NZ588209A patent/NZ588209A/xx not_active IP Right Cessation
- 2009-04-28 KR KR1020107026636A patent/KR20100135325A/ko not_active Withdrawn
- 2009-04-28 AU AU2009242092A patent/AU2009242092A1/en not_active Abandoned
- 2009-04-28 RU RU2010141964/04A patent/RU2010141964A/ru not_active Application Discontinuation
- 2009-04-28 MX MX2010011724A patent/MX2010011724A/es unknown
- 2009-04-28 US US12/990,048 patent/US8524766B2/en not_active Expired - Fee Related
- 2009-04-28 WO PCT/EP2009/055137 patent/WO2009133107A1/en not_active Ceased
- 2009-04-28 CN CN200980115417XA patent/CN102036976B/zh not_active Expired - Fee Related
- 2009-04-28 JP JP2011506689A patent/JP5514804B2/ja not_active Expired - Fee Related
-
2010
- 2010-09-21 IL IL208289A patent/IL208289A0/en unknown
- 2010-09-29 ZA ZA2010/06932A patent/ZA201006932B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US8524766B2 (en) | 2013-09-03 |
| US20110105461A1 (en) | 2011-05-05 |
| MX2010011724A (es) | 2010-11-30 |
| AU2009242092A1 (en) | 2009-11-05 |
| ZA201006932B (en) | 2011-12-28 |
| CN102036976A (zh) | 2011-04-27 |
| EP2271634A1 (en) | 2011-01-12 |
| DK2271634T3 (da) | 2014-05-05 |
| NZ588209A (en) | 2012-08-31 |
| JP2011518858A (ja) | 2011-06-30 |
| BRPI0911772A2 (pt) | 2017-06-27 |
| CN102036976B (zh) | 2013-05-01 |
| EP2271634B1 (en) | 2014-02-12 |
| JP5514804B2 (ja) | 2014-06-04 |
| WO2009133107A1 (en) | 2009-11-05 |
| IL208289A0 (en) | 2010-12-30 |
| KR20100135325A (ko) | 2010-12-24 |
| RU2010141964A (ru) | 2012-06-10 |
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