CA2792539C - N-acyl cyclic amine derivative or pharmaceutically acceptable salt thereof - Google Patents
N-acyl cyclic amine derivative or pharmaceutically acceptable salt thereof Download PDFInfo
- Publication number
- CA2792539C CA2792539C CA2792539A CA2792539A CA2792539C CA 2792539 C CA2792539 C CA 2792539C CA 2792539 A CA2792539 A CA 2792539A CA 2792539 A CA2792539 A CA 2792539A CA 2792539 C CA2792539 C CA 2792539C
- Authority
- CA
- Canada
- Prior art keywords
- optionally substituted
- alkyl
- group
- halogen
- same
- 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.)
- Expired - Fee Related
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- 150000003839 salts Chemical class 0.000 title claims abstract description 69
- 150000001875 compounds Chemical class 0.000 claims abstract description 219
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 196
- 150000002367 halogens Chemical class 0.000 claims abstract description 174
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 174
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 162
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 82
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 78
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 57
- 239000001257 hydrogen Substances 0.000 claims abstract description 41
- 201000000980 schizophrenia Diseases 0.000 claims abstract description 34
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 27
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 5
- -1 cyano, carboxyl Chemical group 0.000 claims description 187
- 125000000623 heterocyclic group Chemical group 0.000 claims description 104
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 55
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 52
- 125000004432 carbon atom Chemical group C* 0.000 claims description 43
- 125000001424 substituent group Chemical group 0.000 claims description 40
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 33
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 33
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 33
- 239000003814 drug Substances 0.000 claims description 33
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 28
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 28
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 26
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 24
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 22
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 19
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 19
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 18
- 229940124597 therapeutic agent Drugs 0.000 claims description 18
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 14
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 14
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 13
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 13
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 12
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 12
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 11
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 10
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 10
- 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims description 9
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 9
- 239000005977 Ethylene Substances 0.000 claims description 9
- 125000005169 cycloalkylcarbonylamino group Chemical group 0.000 claims description 9
- 125000005224 heteroarylcarbonylamino group Chemical group 0.000 claims description 7
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 5
- 208000019022 Mood disease Diseases 0.000 claims description 5
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 5
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 208000024714 major depressive disease Diseases 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000005419 heteroarylsulfonylamino group Chemical group 0.000 claims description 3
- 241000124008 Mammalia Species 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 208000020401 Depressive disease Diseases 0.000 claims 3
- HIOSXSLJQINPMZ-FQEVSTJZSA-N (4-fluorophenyl)-[1-[2-[(2s)-1-[3-fluoro-6-(trifluoromethoxy)-1h-indole-2-carbonyl]pyrrolidin-2-yl]ethyl]piperidin-4-yl]methanone Chemical compound C([C@@H]1CCCN1C(=O)C1=C(C2=CC=C(OC(F)(F)F)C=C2N1)F)CN(CC1)CCC1C(=O)C1=CC=C(F)C=C1 HIOSXSLJQINPMZ-FQEVSTJZSA-N 0.000 claims 2
- IOCJGSXOVZSTBQ-NRFANRHFSA-N [1-[2-[(2s)-1-(3,6-difluoro-1h-indole-2-carbonyl)pyrrolidin-2-yl]ethyl]piperidin-4-yl]-(4-fluorophenyl)methanone Chemical compound C([C@@H]1CCCN1C(=O)C1=C(C2=CC=C(F)C=C2N1)F)CN(CC1)CCC1C(=O)C1=CC=C(F)C=C1 IOCJGSXOVZSTBQ-NRFANRHFSA-N 0.000 claims 2
- WZFNUGOPNOBVRE-VWLOTQADSA-N (4-fluorophenyl)-[1-[2-[(2s)-1-(1-methylindole-5-carbonyl)pyrrolidin-2-yl]ethyl]piperidin-4-yl]methanone Chemical compound C([C@@H]1CCCN1C(=O)C=1C=C2C=CN(C2=CC=1)C)CN(CC1)CCC1C(=O)C1=CC=C(F)C=C1 WZFNUGOPNOBVRE-VWLOTQADSA-N 0.000 claims 1
- QNBRIOXWQACPNP-DEOSSOPVSA-N (4-fluorophenyl)-[1-[2-[(2s)-1-(6-methyl-1h-indole-2-carbonyl)pyrrolidin-2-yl]ethyl]piperidin-4-yl]methanone Chemical compound C([C@@H]1CCCN1C(=O)C1=CC2=CC=C(C=C2N1)C)CN(CC1)CCC1C(=O)C1=CC=C(F)C=C1 QNBRIOXWQACPNP-DEOSSOPVSA-N 0.000 claims 1
- UTHWIOICGCUXQD-SANMLTNESA-N (4-fluorophenyl)-[1-[2-[(2s)-1-(6-propan-2-yl-1h-indole-2-carbonyl)pyrrolidin-2-yl]ethyl]piperidin-4-yl]methanone Chemical compound C([C@@H]1CCCN1C(=O)C1=CC2=CC=C(C=C2N1)C(C)C)CN(CC1)CCC1C(=O)C1=CC=C(F)C=C1 UTHWIOICGCUXQD-SANMLTNESA-N 0.000 claims 1
- SIDLXAYALUAFFR-QFIPXVFZSA-N (4-fluorophenyl)-[1-[2-[(2s)-1-[6-(trifluoromethoxy)-1h-indole-2-carbonyl]pyrrolidin-2-yl]ethyl]piperidin-4-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)C1CCN(CC[C@H]2N(CCC2)C(=O)C=2NC3=CC(OC(F)(F)F)=CC=C3C=2)CC1 SIDLXAYALUAFFR-QFIPXVFZSA-N 0.000 claims 1
- LIFLLNHDTKBBJP-QFIPXVFZSA-N [(2s)-2-[2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl]pyrrolidin-1-yl]-(3-phenyl-1h-pyrazol-5-yl)methanone Chemical compound C([C@H]1CCN2CCC(CC2)C=2C3=CC=C(C=C3ON=2)F)CCN1C(=O)C(NN=1)=CC=1C1=CC=CC=C1 LIFLLNHDTKBBJP-QFIPXVFZSA-N 0.000 claims 1
- LXLZFQZQRGBWHW-NRFANRHFSA-N [1-[2-[(2s)-1-(3-fluoro-1h-indole-2-carbonyl)pyrrolidin-2-yl]ethyl]piperidin-4-yl]-(4-fluorophenyl)methanone Chemical compound C([C@@H]1CCCN1C(=O)C1=C(C2=CC=CC=C2N1)F)CN(CC1)CCC1C(=O)C1=CC=C(F)C=C1 LXLZFQZQRGBWHW-NRFANRHFSA-N 0.000 claims 1
- RBJAORUTFFXQJR-BOXHHOBZSA-N [1-[2-[(2s)-1-(3-fluoro-1h-indole-2-carbonyl)pyrrolidin-2-yl]ethyl]piperidin-4-yl]-(4-fluorophenyl)methanone;hydrochloride Chemical compound Cl.C([C@@H]1CCCN1C(=O)C1=C(C2=CC=CC=C2N1)F)CN(CC1)CCC1C(=O)C1=CC=C(F)C=C1 RBJAORUTFFXQJR-BOXHHOBZSA-N 0.000 claims 1
- ZHBRGKFUCWANDK-NRFANRHFSA-N [1-[2-[(2s)-1-(5-fluoro-4-methoxy-1h-indole-2-carbonyl)pyrrolidin-2-yl]ethyl]piperidin-4-yl]-(4-fluorophenyl)methanone Chemical compound C([C@@H]1CCCN1C(=O)C=1NC=2C=CC(F)=C(C=2C=1)OC)CN(CC1)CCC1C(=O)C1=CC=C(F)C=C1 ZHBRGKFUCWANDK-NRFANRHFSA-N 0.000 claims 1
- VAMONZHTNGAPAG-QHCPKHFHSA-N [1-[2-[(2s)-1-(6-fluoro-1h-indole-2-carbonyl)pyrrolidin-2-yl]ethyl]piperidin-4-yl]-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)C1CCN(CC[C@H]2N(CCC2)C(=O)C=2NC3=CC(F)=CC=C3C=2)CC1 VAMONZHTNGAPAG-QHCPKHFHSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 abstract description 43
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 41
- 208000024891 symptom Diseases 0.000 abstract description 22
- 230000000694 effects Effects 0.000 abstract description 21
- 208000010877 cognitive disease Diseases 0.000 abstract description 15
- 125000002947 alkylene group Chemical group 0.000 abstract description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract description 5
- 208000012902 Nervous system disease Diseases 0.000 abstract description 4
- 208000025966 Neurological disease Diseases 0.000 abstract description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 267
- 125000000217 alkyl group Chemical group 0.000 description 161
- 239000000126 substance Substances 0.000 description 131
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 126
- 239000000243 solution Substances 0.000 description 106
- 239000000203 mixture Substances 0.000 description 95
- 230000002829 reductive effect Effects 0.000 description 91
- 238000000034 method Methods 0.000 description 78
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 69
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 58
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 55
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- 239000012044 organic layer Substances 0.000 description 50
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
- 239000012267 brine Substances 0.000 description 46
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 46
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 43
- 229910052938 sodium sulfate Inorganic materials 0.000 description 42
- 235000011152 sodium sulphate Nutrition 0.000 description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 41
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 38
- 239000010410 layer Substances 0.000 description 38
- 238000003756 stirring Methods 0.000 description 38
- 239000002904 solvent Substances 0.000 description 35
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 31
- 239000000741 silica gel Substances 0.000 description 30
- 229910002027 silica gel Inorganic materials 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- 125000005843 halogen group Chemical group 0.000 description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 125000003545 alkoxy group Chemical group 0.000 description 23
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 22
- 101150041968 CDC13 gene Proteins 0.000 description 22
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 22
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 20
- 230000027455 binding Effects 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000005160 1H NMR spectroscopy Methods 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- 125000000753 cycloalkyl group Chemical group 0.000 description 13
- 239000012442 inert solvent Substances 0.000 description 13
- 125000004430 oxygen atom Chemical group O* 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000003365 glass fiber Substances 0.000 description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 description 12
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 12
- 229960004132 diethyl ether Drugs 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 230000005764 inhibitory process Effects 0.000 description 11
- 102000005962 receptors Human genes 0.000 description 11
- 108020003175 receptors Proteins 0.000 description 11
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 10
- 229940079593 drug Drugs 0.000 description 10
- 125000006239 protecting group Chemical group 0.000 description 10
- 238000010898 silica gel chromatography Methods 0.000 description 10
- XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical class [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 9
- 150000001721 carbon Chemical group 0.000 description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 9
- 125000005842 heteroatom Chemical group 0.000 description 9
- 125000004434 sulfur atom Chemical group 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- 230000003042 antagnostic effect Effects 0.000 description 7
- 239000003638 chemical reducing agent Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- WORJRXHJTUTINR-UHFFFAOYSA-N 1,4-dioxane;hydron;chloride Chemical compound Cl.C1COCCO1 WORJRXHJTUTINR-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 229920002873 Polyethylenimine Polymers 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 125000004414 alkyl thio group Chemical group 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- ODCCJTMPMUFERV-UHFFFAOYSA-N ditert-butyl carbonate Chemical compound CC(C)(C)OC(=O)OC(C)(C)C ODCCJTMPMUFERV-UHFFFAOYSA-N 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 229940076279 serotonin Drugs 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 238000010189 synthetic method Methods 0.000 description 6
- UCTWMZQNUQWSLP-UHFFFAOYSA-N Adrenaline Natural products CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 5
- 125000003282 alkyl amino group Chemical group 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 229960003638 dopamine Drugs 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- 238000001525 receptor binding assay Methods 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
- 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 4
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- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
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- 230000015572 biosynthetic process Effects 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
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- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
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- 159000000007 calcium salts Chemical class 0.000 description 1
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- 235000015165 citric acid Nutrition 0.000 description 1
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- 108010011222 cyclo(Arg-Pro) Proteins 0.000 description 1
- 125000006637 cyclobutyl carbonyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
- 125000006622 cycloheptylmethyl group Chemical group 0.000 description 1
- 125000006639 cyclohexyl carbonyl group Chemical group 0.000 description 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 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- 125000006638 cyclopentyl carbonyl group Chemical group 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000006317 cyclopropyl amino group Chemical group 0.000 description 1
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- RYFCSKVXWRJEOB-UHFFFAOYSA-N dibenzyl propanedioate Chemical compound C=1C=CC=CC=1COC(=O)CC(=O)OCC1=CC=CC=C1 RYFCSKVXWRJEOB-UHFFFAOYSA-N 0.000 description 1
- 125000004639 dihydroindenyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
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- 150000002169 ethanolamines Chemical class 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- JHQOAVNMSFGFAS-UHFFFAOYSA-N ethyl 4-methoxy-1h-indole-2-carboxylate Chemical compound C1=CC=C2NC(C(=O)OCC)=CC2=C1OC JHQOAVNMSFGFAS-UHFFFAOYSA-N 0.000 description 1
- KOLXHQLPMICACW-UHFFFAOYSA-N ethyl 6-fluoro-1h-indole-2-carboxylate Chemical compound C1=C(F)C=C2NC(C(=O)OCC)=CC2=C1 KOLXHQLPMICACW-UHFFFAOYSA-N 0.000 description 1
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
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- 239000008187 granular material Substances 0.000 description 1
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- 150000004678 hydrides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
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- UEXQBEVWFZKHNB-UHFFFAOYSA-N intermediate 29 Natural products C1=CC(N)=CC=C1NC1=NC=CC=N1 UEXQBEVWFZKHNB-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
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- 125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 1
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
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- 239000011707 mineral Substances 0.000 description 1
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- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 229960005017 olanzapine Drugs 0.000 description 1
- KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
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- 229910000489 osmium tetroxide Inorganic materials 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
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- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
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- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
- 229940074439 potassium sodium tartrate Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 238000000746 purification Methods 0.000 description 1
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- JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 description 1
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- 229960001534 risperidone Drugs 0.000 description 1
- RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000012363 selectfluor Substances 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- ZFRKQXVRDFCRJG-UHFFFAOYSA-N skatole Chemical compound C1=CC=C2C(C)=CNC2=C1 ZFRKQXVRDFCRJG-UHFFFAOYSA-N 0.000 description 1
- 229910001023 sodium amalgam Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 229950001675 spiperone Drugs 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229960005453 strychnine Drugs 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- BFFLLBPMZCIGRM-QMMMGPOBSA-N tert-butyl (2s)-2-(hydroxymethyl)pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@H]1CO BFFLLBPMZCIGRM-QMMMGPOBSA-N 0.000 description 1
- OJCLHERKFHHUTB-SECBINFHSA-N tert-butyl (3r)-3-(hydroxymethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@@H](CO)C1 OJCLHERKFHHUTB-SECBINFHSA-N 0.000 description 1
- ROUYFJUVMYHXFJ-UHFFFAOYSA-N tert-butyl 4-oxopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(=O)CC1 ROUYFJUVMYHXFJ-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000006173 tetrahydropyranylmethyl group Chemical group 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- HYWCXWRMUZYRPH-UHFFFAOYSA-N trimethyl(prop-2-enyl)silane Chemical compound C[Si](C)(C)CC=C HYWCXWRMUZYRPH-UHFFFAOYSA-N 0.000 description 1
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 230000007497 verbal memory Effects 0.000 description 1
- 230000031836 visual learning Effects 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 230000003936 working memory Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/16—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/18—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2010-054177 | 2010-03-11 | ||
| JP2010054177 | 2010-03-11 | ||
| JP2010285844 | 2010-12-22 | ||
| JP2010-285844 | 2010-12-22 | ||
| PCT/JP2011/056497 WO2011111875A1 (en) | 2010-03-11 | 2011-03-11 | N-acyl cyclic amine derivative or pharmaceutically acceptable salt thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2792539A1 CA2792539A1 (en) | 2011-09-15 |
| CA2792539C true CA2792539C (en) | 2017-04-18 |
Family
ID=44563664
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2792539A Expired - Fee Related CA2792539C (en) | 2010-03-11 | 2011-03-11 | N-acyl cyclic amine derivative or pharmaceutically acceptable salt thereof |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8541585B2 (enExample) |
| EP (1) | EP2545046A4 (enExample) |
| JP (1) | JP5661791B2 (enExample) |
| KR (1) | KR101756495B1 (enExample) |
| CN (1) | CN102884059B (enExample) |
| AU (1) | AU2011225095C1 (enExample) |
| CA (1) | CA2792539C (enExample) |
| TW (1) | TWI475015B (enExample) |
| WO (1) | WO2011111875A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102180872B (zh) * | 2011-04-01 | 2014-04-02 | 华中科技大学 | [1,3,4]噁二唑类衍生物及其应用 |
| CN104892589A (zh) * | 2014-03-07 | 2015-09-09 | 中国科学院上海药物研究所 | 一类杂环化合物、其制备方法和用途 |
| PL245933B1 (pl) | 2014-07-04 | 2024-11-04 | Inst Farmakologii Polskiej Akademii Nauk | (Chinolino lub izochinolino) sulfonamidy amin cyklicznych, kompozycja je zawierająca, sposób ich wytwarzania oraz ich zastosowanie medyczne |
| CN105315267B (zh) * | 2014-07-30 | 2019-06-04 | 江苏恩华药业股份有限公司 | 一种酰胺类衍生物及其应用 |
| JP2019059672A (ja) * | 2015-12-28 | 2019-04-18 | 大日本住友製薬株式会社 | 治療抵抗性うつ病等の治療薬 |
| UY39569A (es) | 2020-12-17 | 2022-07-29 | Astrazeneca Ab | N-(2-(4-cianotiazolidin-3-il)-2-oxoetil)- quinolin-4-carboxamidas |
| JP7655885B2 (ja) * | 2021-06-30 | 2025-04-02 | 住友ファーマ株式会社 | 脂肪族酸アミド誘導体を含有する医薬組成物 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3133061A (en) | 1962-11-13 | 1964-05-12 | Sterling Drug Inc | Piperidine carboxamides and derivatives thereof |
| FR2285883A1 (fr) * | 1974-09-30 | 1976-04-23 | Cerm Cent Europ Rech Mauvernay | Nouveaux composes chimiques a activite bronchospasmolytique et antitussive, et procede pour leur obtention |
| CA2143117A1 (en) * | 1992-10-07 | 1994-04-14 | Ben E. Evans | Tocolytic oxytocin receptor antagonists |
| JP3162572B2 (ja) | 1993-04-28 | 2001-05-08 | 住友製薬株式会社 | インドロイルグアニジン誘導体 |
| JPH08208602A (ja) | 1994-10-18 | 1996-08-13 | Sumitomo Pharmaceut Co Ltd | インドロイルグアニジン誘導体 |
| FR2729954B1 (fr) | 1995-01-30 | 1997-08-01 | Sanofi Sa | Composes heterocycliques substitues, procede pour leur preparation et compositions pharmaceutiques les contenant |
| US5861417A (en) * | 1996-12-19 | 1999-01-19 | Hoechst Marion Roussel, Inc. | Heterocyclic substituted pyrrolidine amide derivatives |
| US6166037A (en) * | 1997-08-28 | 2000-12-26 | Merck & Co., Inc. | Pyrrolidine and piperidine modulators of chemokine receptor activity |
| UA58476C2 (uk) | 1997-10-09 | 2003-08-15 | Санофі-Сентелябо | Похідні 8-азабіцикло[3.2.1]октан-3-метанаміну, фармацевтична композиція та лікарський засіб |
| EP1386920A4 (en) | 2001-04-20 | 2005-09-14 | Banyu Pharma Co Ltd | benzimidazolone derivatives |
| FR2824828B1 (fr) * | 2001-05-21 | 2005-05-20 | Sanofi Synthelabo | Nouveaux derives de piperidinecarboxamide, un procede pour leur preparation et les compositions pharmaceutiques les contenant |
| EA006082B1 (ru) * | 2001-12-19 | 2005-08-25 | Х. Лундбекк А/С | Производные 3,4-дигидро-1h-изохинолин-2-ила |
| WO2005066165A1 (en) * | 2003-12-31 | 2005-07-21 | Warner-Lambert Company Llc | N-substituted piperidine and piperazine derivatives |
| JP5063351B2 (ja) | 2004-09-17 | 2012-10-31 | エグゼリクシス, インコーポレイテッド | ピラゾールキナーゼモジュレーターおよび使用方法 |
| WO2007061741A2 (en) | 2005-11-17 | 2007-05-31 | Arena Pharmaceuticals, Inc. | Modulators of the h3 receptor useful for the treatment of disorders related thereto |
| JP5176281B2 (ja) | 2006-03-23 | 2013-04-03 | 大日本印刷株式会社 | リチウムイオン電池 |
-
2011
- 2011-03-11 KR KR1020127024562A patent/KR101756495B1/ko not_active Expired - Fee Related
- 2011-03-11 TW TW100108373A patent/TWI475015B/zh not_active IP Right Cessation
- 2011-03-11 CN CN201180023571.1A patent/CN102884059B/zh not_active Expired - Fee Related
- 2011-03-11 US US13/505,161 patent/US8541585B2/en not_active Expired - Fee Related
- 2011-03-11 EP EP11753530.2A patent/EP2545046A4/en not_active Withdrawn
- 2011-03-11 WO PCT/JP2011/056497 patent/WO2011111875A1/en not_active Ceased
- 2011-03-11 AU AU2011225095A patent/AU2011225095C1/en not_active Ceased
- 2011-03-11 CA CA2792539A patent/CA2792539C/en not_active Expired - Fee Related
- 2011-03-11 JP JP2012541257A patent/JP5661791B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| TW201139413A (en) | 2011-11-16 |
| EP2545046A4 (en) | 2015-03-25 |
| JP5661791B2 (ja) | 2015-01-28 |
| CN102884059A (zh) | 2013-01-16 |
| AU2011225095C1 (en) | 2017-01-19 |
| US8541585B2 (en) | 2013-09-24 |
| WO2011111875A1 (en) | 2011-09-15 |
| TWI475015B (zh) | 2015-03-01 |
| EP2545046A1 (en) | 2013-01-16 |
| KR101756495B1 (ko) | 2017-07-10 |
| AU2011225095A1 (en) | 2012-09-27 |
| CN102884059B (zh) | 2015-08-26 |
| US20120214790A1 (en) | 2012-08-23 |
| JP2013522165A (ja) | 2013-06-13 |
| AU2011225095B2 (en) | 2016-05-19 |
| CA2792539A1 (en) | 2011-09-15 |
| KR20130016234A (ko) | 2013-02-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20160202 |
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| MKLA | Lapsed |
Effective date: 20190311 |