JP4785677B2 - 複素環化合物 - Google Patents
複素環化合物 Download PDFInfo
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- JP4785677B2 JP4785677B2 JP2006235401A JP2006235401A JP4785677B2 JP 4785677 B2 JP4785677 B2 JP 4785677B2 JP 2006235401 A JP2006235401 A JP 2006235401A JP 2006235401 A JP2006235401 A JP 2006235401A JP 4785677 B2 JP4785677 B2 JP 4785677B2
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- group
- lower alkyl
- alkyl group
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- groups
- Prior art date
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 35
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 1414
- 150000001875 compounds Chemical class 0.000 claims abstract description 105
- 150000003839 salts Chemical class 0.000 claims abstract description 54
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 10
- 125000004450 alkenylene group Chemical group 0.000 claims abstract description 6
- -1 tetrahydroquinoxalinyl group Chemical group 0.000 claims description 2218
- 125000003545 alkoxy group Chemical group 0.000 claims description 311
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 232
- 125000002252 acyl group Chemical group 0.000 claims description 223
- 125000004043 oxo group Chemical group O=* 0.000 claims description 191
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 183
- 125000003118 aryl group Chemical group 0.000 claims description 179
- 125000001424 substituent group Chemical group 0.000 claims description 174
- 125000003277 amino group Chemical group 0.000 claims description 156
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 128
- 125000005936 piperidyl group Chemical group 0.000 claims description 123
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 113
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 110
- 125000004193 piperazinyl group Chemical group 0.000 claims description 94
- 229910052736 halogen Inorganic materials 0.000 claims description 92
- 125000002883 imidazolyl group Chemical group 0.000 claims description 92
- 125000004076 pyridyl group Chemical group 0.000 claims description 92
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 90
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 87
- 150000002367 halogens Chemical class 0.000 claims description 72
- 125000003342 alkenyl group Chemical group 0.000 claims description 62
- 125000005843 halogen group Chemical group 0.000 claims description 60
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 49
- 125000003435 aroyl group Chemical group 0.000 claims description 48
- 125000002541 furyl group Chemical group 0.000 claims description 47
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 44
- 125000002757 morpholinyl group Chemical group 0.000 claims description 44
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 44
- 125000001544 thienyl group Chemical group 0.000 claims description 44
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 43
- 125000000335 thiazolyl group Chemical group 0.000 claims description 41
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 39
- 125000000623 heterocyclic group Chemical group 0.000 claims description 39
- 125000001589 carboacyl group Chemical group 0.000 claims description 33
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 32
- 125000004104 aryloxy group Chemical group 0.000 claims description 31
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 29
- 125000004414 alkyl thio group Chemical group 0.000 claims description 29
- 229910052757 nitrogen Inorganic materials 0.000 claims description 29
- 125000002971 oxazolyl group Chemical group 0.000 claims description 28
- JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 claims description 24
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 23
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 22
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
- 229920006395 saturated elastomer Polymers 0.000 claims description 22
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 22
- 125000002393 azetidinyl group Chemical group 0.000 claims description 21
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 20
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 20
- 125000001624 naphthyl group Chemical group 0.000 claims description 20
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 19
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 19
- 125000000160 oxazolidinyl group Chemical group 0.000 claims description 17
- 125000005052 dihydropyrazolyl group Chemical group N1(NCC=C1)* 0.000 claims description 16
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 16
- 125000001425 triazolyl group Chemical group 0.000 claims description 15
- 125000000304 alkynyl group Chemical group 0.000 claims description 14
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 14
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims description 14
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 14
- 125000004598 dihydrobenzofuryl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims description 12
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 12
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 12
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 12
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 12
- 125000001041 indolyl group Chemical group 0.000 claims description 12
- 125000005493 quinolyl group Chemical group 0.000 claims description 12
- 125000004434 sulfur atom Chemical group 0.000 claims description 12
- 125000004639 dihydroindenyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 11
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 10
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 10
- 125000002950 monocyclic group Chemical group 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 10
- 125000003965 isoxazolidinyl group Chemical group 0.000 claims description 9
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 125000005554 pyridyloxy group Chemical group 0.000 claims description 8
- 125000001984 thiazolidinyl group Chemical group 0.000 claims description 8
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims description 7
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 7
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000005435 dihydrobenzoxazolyl group Chemical group O1C(NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000004609 dihydroquinazolinyl group Chemical group N1(CN=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000004634 hexahydroazepinyl group Chemical group N1(CCCCCC1)* 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Chemical group 0.000 claims description 6
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 6
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 6
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 5
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 5
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 5
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 5
- 125000004460 dihydrobenzooxazinyl group Chemical group O1N(CCC2=C1C=CC=C2)* 0.000 claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000011593 sulfur Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000001769 aryl amino group Chemical group 0.000 claims description 3
- FDODVZVWGKVMBO-UHFFFAOYSA-N cyclohex-2-ene-1,4-diol Chemical group OC1CCC(O)C=C1 FDODVZVWGKVMBO-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000005476 oxopyrrolidinyl group Chemical group 0.000 claims description 3
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
- QWNCDHYYJATYOG-UHFFFAOYSA-N 2-phenylquinoxaline Chemical compound C1=CC=CC=C1C1=CN=C(C=CC=C2)C2=N1 QWNCDHYYJATYOG-UHFFFAOYSA-N 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 1
- 238000001228 spectrum Methods 0.000 abstract description 5
- 208000015114 central nervous system disease Diseases 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 2
- 231100000957 no side effect Toxicity 0.000 abstract 1
- 208000020016 psychiatric disease Diseases 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 description 187
- 238000006243 chemical reaction Methods 0.000 description 51
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 47
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 47
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 27
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 25
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 22
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
- 239000004305 biphenyl Substances 0.000 description 11
- 235000010290 biphenyl Nutrition 0.000 description 11
- 238000006467 substitution reaction Methods 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 125000000068 chlorophenyl group Chemical group 0.000 description 7
- 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 7
- 239000002994 raw material Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 125000001207 fluorophenyl group Chemical group 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 6
- 125000003944 tolyl group Chemical group 0.000 description 6
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- 230000003042 antagnostic effect Effects 0.000 description 5
- 102000005962 receptors Human genes 0.000 description 5
- 108020003175 receptors Proteins 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- YWSBWHMBCHGEGX-UHFFFAOYSA-N 1,4-dioxa-8-azaspiro[4.5]decyl Chemical group [O+]1=CCOC11CC[N-]CC1 YWSBWHMBCHGEGX-UHFFFAOYSA-N 0.000 description 4
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 4
- 230000002411 adverse Effects 0.000 description 4
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 4
- 150000007514 bases Chemical class 0.000 description 4
- 125000005605 benzo group Chemical group 0.000 description 4
- 239000004210 ether based solvent Substances 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 239000004031 partial agonist Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 description 3
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 description 3
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 3
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 239000005456 alcohol based solvent Substances 0.000 description 3
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 3
- 150000008041 alkali metal carbonates Chemical class 0.000 description 3
- 125000002785 azepinyl group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000004799 bromophenyl group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003759 ester based solvent Substances 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 150000008282 halocarbons Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000004678 hydrides Chemical class 0.000 description 3
- 239000005453 ketone based solvent Substances 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 125000001715 oxadiazolyl group Chemical group 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 3
- 235000015497 potassium bicarbonate Nutrition 0.000 description 3
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Classifications
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- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D417/02—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 two hetero rings
- C07D417/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
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| SA05260357B1 (ar) | 2004-11-19 | 2008-09-08 | ارينا فارماسيتو تيكالز ، أنك | مشتقات 3_فينيل_بيرازول كمعدلات لمستقبل سيروتينين 5_ht2a مفيدة في علاج الاضطرابات المتعلقه به |
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| WO2011151251A1 (en) | 2010-06-01 | 2011-12-08 | Boehringer Ingelheim International Gmbh | New ccr2 antagonists |
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| US10273243B2 (en) * | 2013-03-14 | 2019-04-30 | The Trustees Of Columbia University In The City Of New York | 4-phenylpiperidines, their preparation and use |
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| WO2020087031A1 (en) | 2018-10-26 | 2020-04-30 | The Research Foundation For The State University Of New York | Combination serotonin specific reuptake inhibitor and serotonin 1a receptor partial agonist for reducing l-dopa-induced dyskinesia |
| CN112079812B (zh) * | 2020-09-29 | 2021-08-06 | 浙江大学 | 哌唑类抗精神病药物关键中间体及其电还原方法 |
| CN112125896B (zh) * | 2020-09-29 | 2021-10-29 | 湖南省湘中制药有限公司 | 一种抗精神病药依匹哌唑电化学制备方法 |
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| CN115772175A (zh) * | 2021-09-07 | 2023-03-10 | 中国科学院分子细胞科学卓越创新中心 | 噻吩并环化合物及其制备方法和应用 |
| CN116554145B (zh) * | 2022-01-29 | 2025-06-03 | 江苏恩华药业股份有限公司 | 芳烷基-4-(1h)吲哚基哌嗪衍生物、其制备方法和应用 |
| JP7623550B1 (ja) | 2022-01-29 | 2025-01-28 | スヴェン・ライフ・サイエンシーズ・リミテッド | 精神障害の処置のためのベンゾチアゾール及びベンゾイソキサゾール化合物 |
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