ES2911910T3 - Compuestos de 1-heterociclilisocromanilo y análogos para tratar trastornos del SNC - Google Patents

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Publication number

ES2911910T3

ES2911910T3 ES16708262T ES16708262T ES2911910T3 ES 2911910 T3 ES2911910 T3 ES 2911910T3 ES 16708262 T ES16708262 T ES 16708262T ES 16708262 T ES16708262 T ES 16708262T ES 2911910 T3 ES2911910 T3 ES 2911910T3

Authority

ES

Spain

Prior art keywords

compound

pyrrolidine

tert

butyl

mmol

Prior art date

2015-02-11

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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• 150000001875 compounds Chemical class 0.000 title claims abstract description 200
• 208000015114 central nervous system disease Diseases 0.000 title description 2
• -1 -OH Chemical group 0.000 claims abstract description 79
• 150000003839 salts Chemical class 0.000 claims abstract description 49
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 27
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 21
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 17
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 15
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
• 125000001475 halogen functional group Chemical group 0.000 claims abstract 13
• 239000000203 mixture Substances 0.000 claims description 185
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• 230000000926 neurological effect Effects 0.000 claims description 33
• 229910052799 carbon Inorganic materials 0.000 claims description 31
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• 201000000980 schizophrenia Diseases 0.000 claims description 19
• 238000011282 treatment Methods 0.000 claims description 16
• 208000024714 major depressive disease Diseases 0.000 claims description 14
• 229910052739 hydrogen Inorganic materials 0.000 claims description 13
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 13
• 208000020925 Bipolar disease Diseases 0.000 claims description 10
• 239000003937 drug carrier Substances 0.000 claims description 9
• 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 8
• 239000002671 adjuvant Substances 0.000 claims description 8
• 206010026749 Mania Diseases 0.000 claims description 7
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• 208000028173 post-traumatic stress disease Diseases 0.000 claims description 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 24
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 1
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 227
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 175
• 238000005160 1H NMR spectroscopy Methods 0.000 description 122
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 119
• 238000000034 method Methods 0.000 description 107
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• OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 93
• 239000000243 solution Substances 0.000 description 92
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 90
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 77
• 241001649081 Dina Species 0.000 description 74
• 235000019439 ethyl acetate Nutrition 0.000 description 71
• 150000003840 hydrochlorides Chemical class 0.000 description 68
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 56
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 54
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• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
• 239000012043 crude product Substances 0.000 description 47
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• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 37
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
• 125000005843 halogen group Chemical group 0.000 description 35
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• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 22
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 21
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• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 20
• 239000003795 chemical substances by application Substances 0.000 description 20
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
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• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
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• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
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• 125000000623 heterocyclic group Chemical group 0.000 description 15
• 229920006395 saturated elastomer Polymers 0.000 description 15
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
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• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
• WCHMYCOJRHCHAK-UHFFFAOYSA-N 2-(2-bromo-5-fluorophenyl)ethanol Chemical compound OCCC1=CC(F)=CC=C1Br WCHMYCOJRHCHAK-UHFFFAOYSA-N 0.000 description 13
• 238000005481 NMR spectroscopy Methods 0.000 description 13
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• 238000003818 flash chromatography Methods 0.000 description 13
• 239000000126 substance Substances 0.000 description 13
• YDBPZCVWPFMBDH-QMMMGPOBSA-N tert-butyl (2s)-2-formylpyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@H]1C=O YDBPZCVWPFMBDH-QMMMGPOBSA-N 0.000 description 13
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
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• 230000008448 thought Effects 0.000 description 12
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• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 10
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• BRHMPAKAVCYAIB-RYUDHWBXSA-N (2S)-2-[(1S)-5-fluoro-1,3-dihydro-2-benzofuran-1-yl]pyrrolidine Chemical compound FC1=CC=C2[C@H](OCC2=C1)[C@@H]1CCCN1 BRHMPAKAVCYAIB-RYUDHWBXSA-N 0.000 description 7
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