JP5661791B2 - N−アシル環状アミン誘導体またはその医薬上許容される塩 - Google Patents
N−アシル環状アミン誘導体またはその医薬上許容される塩 Download PDFInfo
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- JP5661791B2 JP5661791B2 JP2012541257A JP2012541257A JP5661791B2 JP 5661791 B2 JP5661791 B2 JP 5661791B2 JP 2012541257 A JP2012541257 A JP 2012541257A JP 2012541257 A JP2012541257 A JP 2012541257A JP 5661791 B2 JP5661791 B2 JP 5661791B2
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- optionally substituted
- substituted
- saturated heterocyclic
- alkyl
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- 150000003839 salts Chemical class 0.000 title claims description 66
- 150000001875 compounds Chemical class 0.000 claims description 218
- -1 C 3 substituted Chemical class 0.000 claims description 194
- 125000005843 halogen group Chemical group 0.000 claims description 193
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 174
- 125000000623 heterocyclic group Chemical group 0.000 claims description 168
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 166
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 129
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 107
- 125000000217 alkyl group Chemical group 0.000 claims description 95
- 125000001072 heteroaryl group Chemical group 0.000 claims description 85
- 125000003118 aryl group Chemical group 0.000 claims description 76
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 52
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 40
- 125000001424 substituent group Chemical group 0.000 claims description 39
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 36
- 229910052799 carbon Inorganic materials 0.000 claims description 36
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 33
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 33
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 32
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 125000003277 amino group Chemical group 0.000 claims description 24
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 24
- 229920006395 saturated elastomer Polymers 0.000 claims description 24
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 22
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 22
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 20
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 18
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 16
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 15
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 15
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 15
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 15
- 125000004434 sulfur atom Chemical group 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 13
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 13
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 13
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 12
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 12
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 12
- 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims description 11
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 11
- 125000004104 aryloxy group Chemical group 0.000 claims description 11
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 10
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 10
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 9
- 125000005224 heteroarylcarbonylamino group Chemical group 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000005169 cycloalkylcarbonylamino group Chemical group 0.000 claims description 8
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 8
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 7
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 7
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 6
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 6
- 125000005419 heteroarylsulfonylamino group Chemical group 0.000 claims description 5
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 5
- 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 description 4
- 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 description 4
- 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 description 4
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 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 description 3
- 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 description 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 description 3
- 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 description 3
- XRUIIJREVLDYTG-UHFFFAOYSA-N 6-(trifluoromethyl)-1h-indole-2-carbaldehyde Chemical compound FC(F)(F)C1=CC=C2C=C(C=O)NC2=C1 XRUIIJREVLDYTG-UHFFFAOYSA-N 0.000 claims description 3
- AWWLOYBXGYSTPT-UHFFFAOYSA-N 6-(trifluoromethylsulfanyl)-1H-indole-2-carbaldehyde Chemical compound FC(SC1=CC=C2C=C(NC2=C1)C=O)(F)F AWWLOYBXGYSTPT-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 description 2
- 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 description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 267
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 126
- 239000000243 solution Substances 0.000 description 98
- 230000002829 reductive effect Effects 0.000 description 91
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 72
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 66
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 60
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 58
- 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
- 239000000203 mixture Substances 0.000 description 51
- 235000002639 sodium chloride Nutrition 0.000 description 50
- 239000012044 organic layer Substances 0.000 description 49
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 46
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 44
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 43
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 42
- 229910052938 sodium sulfate Inorganic materials 0.000 description 42
- 235000011152 sodium sulphate Nutrition 0.000 description 42
- 238000003756 stirring Methods 0.000 description 42
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 31
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 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
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- MXPOLUPSEVGAAS-VIFPVBQESA-N tert-butyl (2s)-2-(2-hydroxyethyl)pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@H]1CCO MXPOLUPSEVGAAS-VIFPVBQESA-N 0.000 description 1
- VPUHJQDNBOTMSI-JTQLQIEISA-N tert-butyl (2s)-2-(2-oxoethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC[C@H]1CC=O VPUHJQDNBOTMSI-JTQLQIEISA-N 0.000 description 1
- DCUJWFJDQRXQBK-VIFPVBQESA-N tert-butyl (2s)-2-(2-oxoethyl)pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@H]1CC=O DCUJWFJDQRXQBK-VIFPVBQESA-N 0.000 description 1
- GSNDDHMLFYORQI-VIFPVBQESA-N tert-butyl (2s)-2-(cyanomethyl)pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@H]1CC#N GSNDDHMLFYORQI-VIFPVBQESA-N 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
- VSVOPDINJSHSBZ-AWEZNQCLSA-N tert-butyl (2s)-2-[(4-methylphenyl)sulfonyloxymethyl]pyrrolidine-1-carboxylate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC[C@H]1N(C(=O)OC(C)(C)C)CCC1 VSVOPDINJSHSBZ-AWEZNQCLSA-N 0.000 description 1
- YUGKZTZHHPHPMT-UWVGGRQHSA-N tert-butyl (2s,5s)-2-(2-hydroxyethyl)-5-methylpyrrolidine-1-carboxylate Chemical compound C[C@H]1CC[C@@H](CCO)N1C(=O)OC(C)(C)C YUGKZTZHHPHPMT-UWVGGRQHSA-N 0.000 description 1
- YBIWUYHZEQSEFL-UWVGGRQHSA-N tert-butyl (2s,5s)-2-(cyanomethyl)-5-methylpyrrolidine-1-carboxylate Chemical compound C[C@H]1CC[C@@H](CC#N)N1C(=O)OC(C)(C)C YBIWUYHZEQSEFL-UWVGGRQHSA-N 0.000 description 1
- ISQYKHGGGYDEKA-SECBINFHSA-N tert-butyl (3r)-3-(2-hydroxyethyl)morpholine-4-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCOC[C@H]1CCO ISQYKHGGGYDEKA-SECBINFHSA-N 0.000 description 1
- KAKZEJFXZCXYMP-SECBINFHSA-N tert-butyl (3r)-3-(2-oxoethyl)morpholine-4-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCOC[C@H]1CC=O KAKZEJFXZCXYMP-SECBINFHSA-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
- GOCADJZGBKCYNV-OAHLLOKOSA-N tert-butyl (3r)-3-[(4-methylphenyl)sulfonyloxymethyl]piperidine-1-carboxylate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC[C@H]1CN(C(=O)OC(C)(C)C)CCC1 GOCADJZGBKCYNV-OAHLLOKOSA-N 0.000 description 1
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- LDEMIIVSMVEGEL-LEWJYISDSA-N tert-butyl 3-[1-[2-[(2s,4r)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidin-2-yl]acetyl]piperidin-4-yl]indole-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1C[C@H](O)C[C@H]1CC(=O)N1CCC(C=2C3=CC=CC=C3N(C(=O)OC(C)(C)C)C=2)CC1 LDEMIIVSMVEGEL-LEWJYISDSA-N 0.000 description 1
- QTIKWXQBUWGSCP-FCHUYYIVSA-N tert-butyl 3-[1-[2-[(2s,4r)-4-methoxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidin-2-yl]acetyl]piperidin-4-yl]indole-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1C[C@H](OC)C[C@H]1CC(=O)N1CCC(C=2C3=CC=CC=C3N(C(=O)OC(C)(C)C)C=2)CC1 QTIKWXQBUWGSCP-FCHUYYIVSA-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
- ORTIWUZWTYLFPU-UHFFFAOYSA-N tert-butyl 5-(2-oxoethyl)-1,4-oxazepane-4-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCOCCC1CC=O ORTIWUZWTYLFPU-UHFFFAOYSA-N 0.000 description 1
- CYNVRSNKCKTHMU-UHFFFAOYSA-N tert-butyl 5-[2-[4-(1h-indol-3-yl)piperidin-1-yl]ethyl]-1,4-oxazepane-4-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCOCCC1CCN1CCC(C=2C3=CC=CC=C3NC=2)CC1 CYNVRSNKCKTHMU-UHFFFAOYSA-N 0.000 description 1
- RCGZPJBSSIQFBH-UHFFFAOYSA-N tert-butyl 5-oxo-1,4-oxazepane-4-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCOCCC1=O RCGZPJBSSIQFBH-UHFFFAOYSA-N 0.000 description 1
- RHUKFNUPFQJTIJ-UHFFFAOYSA-N tert-butyl 5-trimethylsilyloxy-1,4-oxazepane-4-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCOCCC1O[Si](C)(C)C RHUKFNUPFQJTIJ-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
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 230000031836 visual learning Effects 0.000 description 1
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Classifications
-
- 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
- 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
- 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
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- 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
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- C—CHEMISTRY; METALLURGY
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- 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
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- 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
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- 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
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- C07D—HETEROCYCLIC COMPOUNDS
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- 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
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- 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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- 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)
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2012541257A JP5661791B2 (ja) | 2010-03-11 | 2011-03-11 | N−アシル環状アミン誘導体またはその医薬上許容される塩 |
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| Application Number | Priority Date | Filing Date | Title |
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| JP2010054177 | 2010-03-11 | ||
| JP2010054177 | 2010-03-11 | ||
| JP2010285844 | 2010-12-22 | ||
| JP2010285844 | 2010-12-22 | ||
| JP2012541257A JP5661791B2 (ja) | 2010-03-11 | 2011-03-11 | N−アシル環状アミン誘導体またはその医薬上許容される塩 |
| PCT/JP2011/056497 WO2011111875A1 (en) | 2010-03-11 | 2011-03-11 | N-acyl cyclic amine derivative or pharmaceutically acceptable salt thereof |
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| Publication Number | Publication Date |
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| JP2013522165A JP2013522165A (ja) | 2013-06-13 |
| JP2013522165A5 JP2013522165A5 (enExample) | 2014-03-13 |
| JP5661791B2 true JP5661791B2 (ja) | 2015-01-28 |
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| EP (1) | EP2545046A4 (enExample) |
| JP (1) | JP5661791B2 (enExample) |
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| 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 |
| PE20232046A1 (es) | 2020-12-17 | 2023-12-27 | 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 |
| AU5292393A (en) | 1992-10-07 | 1994-04-26 | Merck & Co., Inc. | 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 |
| WO2002085890A1 (en) | 2001-04-20 | 2002-10-31 | Banyu Pharmaceutical 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 |
| MXPA04005988A (es) | 2001-12-19 | 2004-09-27 | Lundbeck & Co As H | 3,4-dihidro-1h-isoquinolin-2-il-derivados. |
| WO2005066165A1 (en) | 2003-12-31 | 2005-07-21 | Warner-Lambert Company Llc | N-substituted piperidine and piperazine derivatives |
| EP1797072A4 (en) | 2004-09-17 | 2009-09-09 | Exelixis Inc | PYRAZOLKINASE MODULATORS AND USE METHOD |
| CA2628527A1 (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 |
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- 2011-03-11 CN CN201180023571.1A patent/CN102884059B/zh not_active Expired - Fee Related
- 2011-03-11 EP EP11753530.2A patent/EP2545046A4/en not_active Withdrawn
- 2011-03-11 US US13/505,161 patent/US8541585B2/en not_active Expired - Fee Related
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- 2011-03-11 JP JP2012541257A patent/JP5661791B2/ja not_active Expired - Fee Related
- 2011-03-11 WO PCT/JP2011/056497 patent/WO2011111875A1/en not_active Ceased
- 2011-03-11 TW TW100108373A patent/TWI475015B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2792539C (en) | 2017-04-18 |
| KR20130016234A (ko) | 2013-02-14 |
| AU2011225095C1 (en) | 2017-01-19 |
| EP2545046A1 (en) | 2013-01-16 |
| AU2011225095A1 (en) | 2012-09-27 |
| EP2545046A4 (en) | 2015-03-25 |
| WO2011111875A1 (en) | 2011-09-15 |
| KR101756495B1 (ko) | 2017-07-10 |
| US8541585B2 (en) | 2013-09-24 |
| AU2011225095B2 (en) | 2016-05-19 |
| CN102884059B (zh) | 2015-08-26 |
| TWI475015B (zh) | 2015-03-01 |
| CN102884059A (zh) | 2013-01-16 |
| CA2792539A1 (en) | 2011-09-15 |
| JP2013522165A (ja) | 2013-06-13 |
| TW201139413A (en) | 2011-11-16 |
| US20120214790A1 (en) | 2012-08-23 |
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