JP5146766B2 - ５−ヒドロキシトリプタミン−６リガンドとしての置換−３−スルホニルインダゾール誘導体 - Google Patents

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Publication number

JP5146766B2

JP5146766B2 JP2008526995A JP2008526995A JP5146766B2 JP 5146766 B2 JP5146766 B2 JP 5146766B2 JP 2008526995 A JP2008526995 A JP 2008526995A JP 2008526995 A JP2008526995 A JP 2008526995A JP 5146766 B2 JP5146766 B2 JP 5146766B2

Authority

JP

Japan

Prior art keywords

mmol

indazol

ethyl

naphthalene

sulfonyl

Prior art date

2005-08-15

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.)

Expired - Fee Related

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• -1 Substituted-3-sulfonylindazole Chemical class 0.000 title claims description 201
• 239000003446 ligand Substances 0.000 title description 9
• 150000001875 compounds Chemical class 0.000 claims description 305
• 239000000203 mixture Substances 0.000 claims description 164
• 150000001412 amines Chemical class 0.000 claims description 34
• 150000003839 salts Chemical class 0.000 claims description 22
• 108091005435 5-HT6 receptors Proteins 0.000 claims description 15
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
• 208000015114 central nervous system disease Diseases 0.000 claims description 8
• NXQGEDVQXVTCDA-UHFFFAOYSA-N n,n-dimethyl-3-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]propan-1-amine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCCN(C)C)=CC=CC2=C1 NXQGEDVQXVTCDA-UHFFFAOYSA-N 0.000 claims description 7
• FZIDAMYBULCBST-UHFFFAOYSA-N n,n-dimethyl-2-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]ethanamine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCN(C)C)=CC=CC2=C1 FZIDAMYBULCBST-UHFFFAOYSA-N 0.000 claims description 5
• NTWIXXNPWJCUKO-UHFFFAOYSA-N 2-[[3-(benzenesulfonyl)-2h-indazol-5-yl]oxy]-n-ethylethanamine Chemical compound C12=CC(OCCNCC)=CC=C2NN=C1S(=O)(=O)C1=CC=CC=C1 NTWIXXNPWJCUKO-UHFFFAOYSA-N 0.000 claims description 4
• ISLLLFJSCFDYNX-UHFFFAOYSA-N n-[2-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]ethyl]propan-2-amine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCNC(C)C)=CC=CC2=C1 ISLLLFJSCFDYNX-UHFFFAOYSA-N 0.000 claims description 4
• XJBFZLJZSPJQRV-UHFFFAOYSA-N n-methyl-3-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]propan-1-amine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCCNC)=CC=CC2=C1 XJBFZLJZSPJQRV-UHFFFAOYSA-N 0.000 claims description 4
• 208000019901 Anxiety disease Diseases 0.000 claims description 3
• 230000036506 anxiety Effects 0.000 claims description 3
• 230000036651 mood Effects 0.000 claims description 3
• UHISQLHPYWNPQW-UHFFFAOYSA-N n-ethyl-3-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]propan-1-amine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCCNCC)=CC=CC2=C1 UHISQLHPYWNPQW-UHFFFAOYSA-N 0.000 claims description 3
• IWDPUZMWDBQBAA-UHFFFAOYSA-N n-ethyl-n-methyl-2-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]ethanamine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCN(C)CC)=CC=CC2=C1 IWDPUZMWDBQBAA-UHFFFAOYSA-N 0.000 claims description 3
• BQHVXLWCYFWZGS-UHFFFAOYSA-N n-methyl-2-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]ethanamine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCNC)=CC=CC2=C1 BQHVXLWCYFWZGS-UHFFFAOYSA-N 0.000 claims description 3
• PTCSHLCQBWNEIT-UHFFFAOYSA-N 3-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]-n-propan-2-ylpropan-1-amine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCCNC(C)C)=CC=CC2=C1 PTCSHLCQBWNEIT-UHFFFAOYSA-N 0.000 claims description 2
• 208000030814 Eating disease Diseases 0.000 claims description 2
• 208000019454 Feeding and Eating disease Diseases 0.000 claims description 2
• 208000018522 Gastrointestinal disease Diseases 0.000 claims description 2
• 235000014632 disordered eating Nutrition 0.000 claims description 2
• DMCNDPIVSZOUSA-UHFFFAOYSA-N n,n-diethyl-2-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]ethanamine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCN(CC)CC)=CC=CC2=C1 DMCNDPIVSZOUSA-UHFFFAOYSA-N 0.000 claims description 2
• FSUSRKMBYMEREP-UHFFFAOYSA-N n,n-diethyl-3-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]propan-1-amine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCCN(CC)CC)=CC=CC2=C1 FSUSRKMBYMEREP-UHFFFAOYSA-N 0.000 claims description 2
• KMVSONDYAPBQHT-UHFFFAOYSA-N n,n-diethyl-4-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]butan-1-amine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCCCN(CC)CC)=CC=CC2=C1 KMVSONDYAPBQHT-UHFFFAOYSA-N 0.000 claims description 2
• YAYVSICZNRZOGT-UHFFFAOYSA-N n-[2-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]ethyl]cyclopentanamine Chemical compound C=1C=CC2=CC=CC=C2C=1S(=O)(=O)C(C1=C2)=NNC1=CC=C2OCCNC1CCCC1 YAYVSICZNRZOGT-UHFFFAOYSA-N 0.000 claims description 2
• MDTWXGWSXAWFTR-UHFFFAOYSA-N n-[2-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]ethyl]cyclopropanamine Chemical compound C=1C=CC2=CC=CC=C2C=1S(=O)(=O)C(C1=C2)=NNC1=CC=C2OCCNC1CC1 MDTWXGWSXAWFTR-UHFFFAOYSA-N 0.000 claims description 2
• LKWUURPREMRAAG-UHFFFAOYSA-N n-[3-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]propyl]butan-1-amine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCCNCCCC)=CC=CC2=C1 LKWUURPREMRAAG-UHFFFAOYSA-N 0.000 claims description 2
• LQTIUQBMJBAWMD-UHFFFAOYSA-N n-[3-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]propyl]cyclopentanamine Chemical compound C=1C=CC2=CC=CC=C2C=1S(=O)(=O)C(C1=C2)=NNC1=CC=C2OCCCNC1CCCC1 LQTIUQBMJBAWMD-UHFFFAOYSA-N 0.000 claims description 2
• ROYVCTNFSAPNLB-UHFFFAOYSA-N n-[3-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]propyl]cyclopropanamine Chemical compound C=1C=CC2=CC=CC=C2C=1S(=O)(=O)C(C1=C2)=NNC1=CC=C2OCCCNC1CC1 ROYVCTNFSAPNLB-UHFFFAOYSA-N 0.000 claims description 2
• NKQVYPRRVFKJKV-UHFFFAOYSA-N n-ethyl-2-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]ethanamine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCNCC)=CC=CC2=C1 NKQVYPRRVFKJKV-UHFFFAOYSA-N 0.000 claims description 2
• KFBPBGMNYWGBTK-UHFFFAOYSA-N n-ethyl-n-methyl-3-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]propan-1-amine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCCN(C)CC)=CC=CC2=C1 KFBPBGMNYWGBTK-UHFFFAOYSA-N 0.000 claims description 2
• BASVWLXZWDUZQN-UHFFFAOYSA-N n-methyl-4-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]-n-propylbutan-1-amine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCCCN(C)CCC)=CC=CC2=C1 BASVWLXZWDUZQN-UHFFFAOYSA-N 0.000 claims description 2
• SVLXZUBLXJBMKV-UHFFFAOYSA-N 3-(diethylamino)-n-(3-naphthalen-1-ylsulfonyl-2h-indazol-7-yl)propanamide Chemical compound C1=CC=C2C(S(=O)(=O)C=3C=4C=CC=C(C=4NN=3)NC(=O)CCN(CC)CC)=CC=CC2=C1 SVLXZUBLXJBMKV-UHFFFAOYSA-N 0.000 claims 1
• 208000010643 digestive system disease Diseases 0.000 claims 1
• 208000018685 gastrointestinal system disease Diseases 0.000 claims 1
• AOTJTGAUOFWJJI-UHFFFAOYSA-N n,n-dimethyl-4-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]butan-1-amine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCCCN(C)C)=CC=CC2=C1 AOTJTGAUOFWJJI-UHFFFAOYSA-N 0.000 claims 1
• CTSGPIZWRUYBCN-UHFFFAOYSA-N n-methyl-4-[(3-naphthalen-1-ylsulfonyl-2h-indazol-5-yl)oxy]butan-1-amine Chemical compound C1=CC=C2C(S(=O)(=O)C3=NNC4=CC=C(C=C43)OCCCCNC)=CC=CC2=C1 CTSGPIZWRUYBCN-UHFFFAOYSA-N 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 510
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 323
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 266
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 242
• 235000019439 ethyl acetate Nutrition 0.000 description 201
• 239000011541 reaction mixture Substances 0.000 description 185
• 239000007787 solid Substances 0.000 description 182
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 158
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 136
• 239000000243 solution Substances 0.000 description 126
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 126
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 121
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 115
• 239000012267 brine Substances 0.000 description 97
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 97
• 238000001819 mass spectrum Methods 0.000 description 81
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 77
• 239000011734 sodium Substances 0.000 description 76
• 239000012074 organic phase Substances 0.000 description 74
• 238000000034 method Methods 0.000 description 73
• 229910052757 nitrogen Inorganic materials 0.000 description 72
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 62
• 235000017557 sodium bicarbonate Nutrition 0.000 description 62
• 238000001816 cooling Methods 0.000 description 61
• 230000008018 melting Effects 0.000 description 61
• 238000002844 melting Methods 0.000 description 61
• 239000006260 foam Substances 0.000 description 58
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 57
• 238000000921 elemental analysis Methods 0.000 description 55
• 238000003818 flash chromatography Methods 0.000 description 54
• QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 50
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 49
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 47
• 239000000460 chlorine Substances 0.000 description 45
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 40
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 38
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 37
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 35
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 32
• 239000003480 eluent Substances 0.000 description 31
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 29
• 238000004128 high performance liquid chromatography Methods 0.000 description 29
• 239000002904 solvent Substances 0.000 description 27
• 238000006243 chemical reaction Methods 0.000 description 23
• 238000003756 stirring Methods 0.000 description 23
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 22
• 239000012043 crude product Substances 0.000 description 22
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 22
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 21
• 229910052760 oxygen Inorganic materials 0.000 description 21
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 21
• 125000001072 heteroaryl group Chemical group 0.000 description 20
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
• 238000001291 vacuum drying Methods 0.000 description 19
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 18
• 125000003118 aryl group Chemical group 0.000 description 18
• 239000000706 filtrate Substances 0.000 description 18
• 229910052763 palladium Inorganic materials 0.000 description 18
• 239000000047 product Substances 0.000 description 18
• 125000000547 substituted alkyl group Chemical group 0.000 description 17
• 229910052717 sulfur Inorganic materials 0.000 description 17
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 16
• 239000000908 ammonium hydroxide Substances 0.000 description 16
• 125000000753 cycloalkyl group Chemical group 0.000 description 16
• 102000005962 receptors Human genes 0.000 description 16
• 108020003175 receptors Proteins 0.000 description 16
• 235000010288 sodium nitrite Nutrition 0.000 description 16
• 238000005984 hydrogenation reaction Methods 0.000 description 15
• 238000010183 spectrum analysis Methods 0.000 description 15
• 125000006012 2-chloroethoxy group Chemical group 0.000 description 14
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
• 150000003840 hydrochlorides Chemical class 0.000 description 14
• 239000007788 liquid Substances 0.000 description 14
• 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 description 13
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 description 13
• 0 C1CC*CC1 Chemical compound C1CC*CC1 0.000 description 13
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 13
• 238000001035 drying Methods 0.000 description 13
• JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 13
• 239000011345 viscous material Substances 0.000 description 13
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 12
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 12
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 description 11
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 11
• 229910052739 hydrogen Inorganic materials 0.000 description 11
• 239000007858 starting material Substances 0.000 description 11
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 11
• APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 description 10
• XHMLYFRREKIYDU-UHFFFAOYSA-N 1-(chloromethylsulfonyl)naphthalene Chemical compound C1=CC=C2C(S(=O)(=O)CCl)=CC=CC2=C1 XHMLYFRREKIYDU-UHFFFAOYSA-N 0.000 description 10
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
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• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
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• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 9
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• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 9
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• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
• 125000003342 alkenyl group Chemical group 0.000 description 8
• 125000000217 alkyl group Chemical group 0.000 description 8
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 description 8
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• 239000012458 free base Substances 0.000 description 8
• 125000005842 heteroatom Chemical group 0.000 description 8
• 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 description 8
• 238000004305 normal phase HPLC Methods 0.000 description 8
• 239000003208 petroleum Substances 0.000 description 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
• 230000002829 reductive effect Effects 0.000 description 8
• 125000001424 substituent group Chemical group 0.000 description 8
• LZIYAIRGDHSVED-UHFFFAOYSA-N 1-(bromomethyl)-3-chlorobenzene Chemical compound ClC1=CC=CC(CBr)=C1 LZIYAIRGDHSVED-UHFFFAOYSA-N 0.000 description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
• 239000004480 active ingredient Substances 0.000 description 7
• 125000000304 alkynyl group Chemical group 0.000 description 7
• 125000002619 bicyclic group Chemical group 0.000 description 7
• 229910052794 bromium Inorganic materials 0.000 description 7
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