JP2013535408A5 - - Google Patents
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- Publication number
- JP2013535408A5 JP2013535408A5 JP2013506362A JP2013506362A JP2013535408A5 JP 2013535408 A5 JP2013535408 A5 JP 2013535408A5 JP 2013506362 A JP2013506362 A JP 2013506362A JP 2013506362 A JP2013506362 A JP 2013506362A JP 2013535408 A5 JP2013535408 A5 JP 2013535408A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- halogen atom
- alkyl
- substituted
- ring
- 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.)
- Granted
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- 125000005843 halogen group Chemical group 0.000 claims 73
- 125000000217 alkyl group Chemical group 0.000 claims 50
- 125000001424 substituent group Chemical group 0.000 claims 36
- -1 7,7-diphenyl-6,7-dihydro-5H-pyrrolo [2,1-c] [1,2,4] thiadiazole-3-ylidene Chemical group 0.000 claims 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 26
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical class C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims 20
- 125000003545 alkoxy group Chemical group 0.000 claims 20
- 150000003839 salts Chemical class 0.000 claims 20
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 17
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 10
- 150000004945 aromatic hydrocarbons Chemical group 0.000 claims 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 10
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 8
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 8
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims 8
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 7
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 7
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 7
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 7
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 6
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 6
- 125000004429 atom Chemical group 0.000 claims 6
- 125000004465 cycloalkenyloxy group Chemical group 0.000 claims 6
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 125000005554 pyridyloxy group Chemical group 0.000 claims 6
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 5
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 5
- 150000001924 cycloalkanes Chemical class 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 5
- 229930192474 thiophene Natural products 0.000 claims 5
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 4
- 125000006591 (C2-C6) alkynylene group Chemical group 0.000 claims 4
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 4
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 4
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical class CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical class C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims 4
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 4
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 4
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims 4
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical class C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 4
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims 3
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims 3
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 3
- NOIXNOMHHWGUTG-UHFFFAOYSA-N 2-[[4-[4-pyridin-4-yl-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(CC(F)(F)F)C=C1C1=CC=NC=C1 NOIXNOMHHWGUTG-UHFFFAOYSA-N 0.000 claims 3
- UCFSYHMCKWNKAH-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound CC1(C)OBOC1(C)C UCFSYHMCKWNKAH-UHFFFAOYSA-N 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 3
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 3
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 3
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims 3
- 125000005530 alkylenedioxy group Chemical group 0.000 claims 3
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 3
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 206010022437 insomnia Diseases 0.000 claims 3
- 125000003566 oxetanyl group Chemical group 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 201000000980 schizophrenia Diseases 0.000 claims 3
- 201000002859 sleep apnea Diseases 0.000 claims 3
- 125000006850 spacer group Chemical group 0.000 claims 3
- KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical class C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 claims 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 2
- 125000004450 alkenylene group Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 239000000470 constituent Substances 0.000 claims 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 230000000069 prophylactic effect Effects 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 150000005071 1,2,4-oxadiazoles Chemical class 0.000 claims 1
- ZHLRQRDFRMUFGQ-UHFFFAOYSA-N 7-methyl-4,8-diphenyl-6h-pyrazolo[5,1-c][1,2,4]thiadiazine 2,2-dioxide Chemical compound N12NC(C)=C(C=3C=CC=CC=3)C2=NS(=O)(=O)C=C1C1=CC=CC=C1 ZHLRQRDFRMUFGQ-UHFFFAOYSA-N 0.000 claims 1
- 125000005330 8 membered heterocyclic group Chemical group 0.000 claims 1
- IZPXKCJSCJNGAF-UHFFFAOYSA-N 9-(4-cyclohexyloxyphenyl)-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide Chemical compound C12=NS(=O)(=O)CCN2C=CC=C1C(C=C1)=CC=C1OC1CCCCC1 IZPXKCJSCJNGAF-UHFFFAOYSA-N 0.000 claims 1
- PXJBHEHFVQVDDS-UHFFFAOYSA-N 9-(4-cyclohexyloxyphenyl)-7-methyl-3,4-dihydropyrazino[2,1-c][1,2,4]thiadiazine 2,2-dioxide Chemical compound N=1C(C)=CN2CCS(=O)(=O)N=C2C=1C(C=C1)=CC=C1OC1CCCCC1 PXJBHEHFVQVDDS-UHFFFAOYSA-N 0.000 claims 1
- VKKLOYOLCCDGLD-UHFFFAOYSA-N 9-(4-phenoxyphenyl)-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide Chemical compound C12=NS(=O)(=O)CCN2C=CC=C1C(C=C1)=CC=C1OC1=CC=CC=C1 VKKLOYOLCCDGLD-UHFFFAOYSA-N 0.000 claims 1
- CFZWPHLWYCTJFX-UHFFFAOYSA-N 9-[4-(4-methylphenoxy)phenyl]-3,4-dihydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide Chemical compound C1=CC(C)=CC=C1OC1=CC=C(C=2C3=NS(=O)(=O)CCN3C=CC=2)C=C1 CFZWPHLWYCTJFX-UHFFFAOYSA-N 0.000 claims 1
- 102000003678 AMPA Receptors Human genes 0.000 claims 1
- 108090000078 AMPA Receptors Proteins 0.000 claims 1
- 125000005914 C6-C14 aryloxy group Chemical group 0.000 claims 1
- 208000020401 Depressive disease Diseases 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 1
- 150000001539 azetidines Chemical class 0.000 claims 1
- 150000001556 benzimidazoles Chemical class 0.000 claims 1
- 150000005528 benzodioxoles Chemical class 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 239000003623 enhancer Substances 0.000 claims 1
- 150000002240 furans Chemical class 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 150000002475 indoles Chemical class 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 150000002921 oxetanes Chemical class 0.000 claims 1
- 150000003053 piperidines Chemical class 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 229940043274 prophylactic drug Drugs 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
- 150000003248 quinolines Chemical class 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 229940126585 therapeutic drug Drugs 0.000 claims 1
- 150000003577 thiophenes Chemical class 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2013506362A JP5788496B2 (ja) | 2010-08-10 | 2011-08-09 | 複素環化合物およびその用途 |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2010179577 | 2010-08-10 | ||
| JP2010179577 | 2010-08-10 | ||
| PCT/JP2011/068497 WO2012020848A1 (en) | 2010-08-10 | 2011-08-09 | Heterocyclic compound and use thereof |
| JP2013506362A JP5788496B2 (ja) | 2010-08-10 | 2011-08-09 | 複素環化合物およびその用途 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015149216A Division JP6113789B2 (ja) | 2010-08-10 | 2015-07-29 | 複素環化合物およびその用途 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013535408A JP2013535408A (ja) | 2013-09-12 |
| JP2013535408A5 true JP2013535408A5 (cg-RX-API-DMAC7.html) | 2014-09-18 |
| JP5788496B2 JP5788496B2 (ja) | 2015-09-30 |
Family
ID=44534564
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013506362A Active JP5788496B2 (ja) | 2010-08-10 | 2011-08-09 | 複素環化合物およびその用途 |
| JP2015149216A Active JP6113789B2 (ja) | 2010-08-10 | 2015-07-29 | 複素環化合物およびその用途 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015149216A Active JP6113789B2 (ja) | 2010-08-10 | 2015-07-29 | 複素環化合物およびその用途 |
Country Status (39)
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| WO2013118845A1 (ja) * | 2012-02-08 | 2013-08-15 | 武田薬品工業株式会社 | 複素環化合物およびその用途 |
| US20150011554A1 (en) * | 2013-06-13 | 2015-01-08 | Veroscience Llc | Compositions and Methods for Treating Metabolic Disorders |
| EA028637B1 (ru) | 2013-06-27 | 2017-12-29 | Пфайзер Инк. | Гетероароматические соединения и их применение в качестве лигандов к дофаминовым d1-рецепторам |
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| CN110312712B (zh) | 2016-12-21 | 2023-06-23 | Fmc公司 | 硝酮除草剂 |
| CN107892697B (zh) | 2016-12-26 | 2020-11-03 | 郑州泰基鸿诺医药股份有限公司 | 一种[1,3]噻嗪-2-胺类化合物及应用，药物组合物 |
| JP7201609B2 (ja) | 2017-03-21 | 2023-01-10 | エフ エム シー コーポレーション | ピロリジノン及びこれらを調製するためのプロセス |
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