JP2009507801A5

JP2009507801A5 -

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Publication number: JP2009507801A5
Authority: JP; Japan
Prior art keywords: mmol; added; solution; compound; stirred
Prior art date: 2006-09-07
Legal status : Granted

Application number

JP2008529564A

Other languages

English (en)

Japanese (ja)

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JP5121716B2 (ja

JP2009507801A (ja

Filing date

2006-09-07

Publication date

2012-10-25

2005-09-09 Priority claimed from GB0518472A external-priority patent/GB0518472D0/en

2006-06-06 Priority claimed from GB0611153A external-priority patent/GB0611153D0/en

2006-09-07 Application filed filed Critical

2006-09-07 Priority claimed from PCT/EP2006/008845 external-priority patent/WO2007028654A1/en

2009-02-26 Publication of JP2009507801A publication Critical patent/JP2009507801A/ja

2012-10-25 Publication of JP2009507801A5 publication Critical patent/JP2009507801A5/ja

2013-01-16 Application granted granted Critical

2013-01-16 Publication of JP5121716B2 publication Critical patent/JP5121716B2/ja

Status Active legal-status Critical Current

2026-09-07 Anticipated expiration legal-status Critical

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150000001875 compounds Chemical class 0.000 claims description 321
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 163
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 156
-1 4- fluoro-2-methylphenyl Chemical group 0.000 claims description 85
150000003839 salts Chemical class 0.000 claims description 55
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 49
208000035475 disorder Diseases 0.000 claims description 45
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 32
208000020016 psychiatric disease Diseases 0.000 claims description 18
239000003814 drug Substances 0.000 claims description 16
239000008194 pharmaceutical composition Substances 0.000 claims description 12
201000000980 schizophrenia Diseases 0.000 claims description 11
208000007848 Alcoholism Diseases 0.000 claims description 8
208000028505 alcohol-related disease Diseases 0.000 claims description 8
239000003937 drug carrier Substances 0.000 claims description 7
208000020925 Bipolar disease Diseases 0.000 claims description 6
201000007930 alcohol dependence Diseases 0.000 claims description 6
208000020401 Depressive disease Diseases 0.000 claims description 5
208000028017 Psychotic disease Diseases 0.000 claims description 4
238000002560 therapeutic procedure Methods 0.000 claims description 3
229940125782 compound 2 Drugs 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 508
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 458
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 353
239000000243 solution Substances 0.000 description 265
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 164
235000019439 ethyl acetate Nutrition 0.000 description 144
238000001819 mass spectrum Methods 0.000 description 139
239000002904 solvent Substances 0.000 description 138
238000006243 chemical reaction Methods 0.000 description 132
239000011541 reaction mixture Substances 0.000 description 115
239000000203 mixture Substances 0.000 description 109
125000000217 alkyl group Chemical group 0.000 description 103
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 98
239000000047 product Substances 0.000 description 89
229910052757 nitrogen Inorganic materials 0.000 description 88
238000005160 1H NMR spectroscopy Methods 0.000 description 87
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 87
239000007787 solid Substances 0.000 description 86
239000000377 silicon dioxide Substances 0.000 description 79
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 75
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 72
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 71
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 70
239000012043 crude product Substances 0.000 description 67
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 66
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 65
238000001946 ultra-performance liquid chromatography-mass spectrometry Methods 0.000 description 65
238000005481 NMR spectroscopy Methods 0.000 description 62
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 59
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 54
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 52
229920006395 saturated elastomer Polymers 0.000 description 51
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 51
239000000460 chlorine Substances 0.000 description 50
230000002829 reductive effect Effects 0.000 description 50
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 47
125000004433 nitrogen atom Chemical group N* 0.000 description 47
238000000746 purification Methods 0.000 description 47
239000011734 sodium Substances 0.000 description 47
239000003153 chemical reaction reagent Substances 0.000 description 43
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 41
229910000041 hydrogen chloride Inorganic materials 0.000 description 41
238000003818 flash chromatography Methods 0.000 description 39
BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 37
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 37
229910000027 potassium carbonate Inorganic materials 0.000 description 36
239000000725 suspension Substances 0.000 description 36
239000008346 aqueous phase Substances 0.000 description 35
239000002585 base Substances 0.000 description 34
239000003921 oil Substances 0.000 description 33
235000019198 oils Nutrition 0.000 description 33
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
238000004587 chromatography analysis Methods 0.000 description 32
238000010511 deprotection reaction Methods 0.000 description 32
125000003545 alkoxy group Chemical group 0.000 description 31
238000000034 method Methods 0.000 description 30
125000002887 hydroxy group Chemical group [H]O* 0.000 description 28
229910052736 halogen Inorganic materials 0.000 description 27
150000002367 halogens Chemical class 0.000 description 27
239000007864 aqueous solution Substances 0.000 description 26
239000008186 active pharmaceutical agent Substances 0.000 description 25
239000012071 phase Substances 0.000 description 24
239000012267 brine Substances 0.000 description 23
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 23
238000004458 analytical method Methods 0.000 description 22
CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 22
229910052763 palladium Inorganic materials 0.000 description 22
229910052739 hydrogen Inorganic materials 0.000 description 21
239000013058 crude material Substances 0.000 description 20
239000001257 hydrogen Substances 0.000 description 20
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 20
239000012074 organic phase Substances 0.000 description 20
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
239000000284 extract Substances 0.000 description 19
125000006239 protecting group Chemical group 0.000 description 19
238000003756 stirring Methods 0.000 description 19
239000002249 anxiolytic agent Substances 0.000 description 18
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 18
208000019901 Anxiety disease Diseases 0.000 description 17
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
239000002253 acid Substances 0.000 description 17
208000019116 sleep disease Diseases 0.000 description 17
BWHDROKFUHTORW-UHFFFAOYSA-N tri-tert-butylphosphine Substances CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 17
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
230000000949 anxiolytic effect Effects 0.000 description 16
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 16
WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 16
238000010992 reflux Methods 0.000 description 16
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 16
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 15
125000002091 cationic group Chemical group 0.000 description 15
238000004128 high performance liquid chromatography Methods 0.000 description 15
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 15
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 15
239000007858 starting material Substances 0.000 description 15
TYRNNGZQKUKQJV-UHFFFAOYSA-N 1,3,4,6,7,8,9,9a-octahydropyrazino[2,1-c][1,4]thiazine 2,2-dioxide Chemical compound C1CNCC2CS(=O)(=O)CCN21 TYRNNGZQKUKQJV-UHFFFAOYSA-N 0.000 description 14
238000002360 preparation method Methods 0.000 description 14
239000012321 sodium triacetoxyborohydride Substances 0.000 description 14
239000000126 substance Substances 0.000 description 14
208000019022 Mood disease Diseases 0.000 description 13
IRLPJUXYSAAKGO-STQMWFEESA-N [(7s,9as)-1,3,4,6,7,8,9,9a-octahydropyrazino[2,1-c][1,4]oxazin-7-yl]methoxy-tert-butyl-dimethylsilane Chemical compound C1COC[C@@H]2CN[C@H](CO[Si](C)(C)C(C)(C)C)CN21 IRLPJUXYSAAKGO-STQMWFEESA-N 0.000 description 13
ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 13
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 13
239000002244 precipitate Substances 0.000 description 13
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
206010012218 Delirium Diseases 0.000 description 12
125000002619 bicyclic group Chemical group 0.000 description 12
239000000706 filtrate Substances 0.000 description 12
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
239000000523 sample Substances 0.000 description 12
CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 11
239000000935 antidepressant agent Substances 0.000 description 11
229940005513 antidepressants Drugs 0.000 description 11
229910052799 carbon Inorganic materials 0.000 description 11
239000003054 catalyst Substances 0.000 description 11
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 11
238000001914 filtration Methods 0.000 description 11
239000012299 nitrogen atmosphere Substances 0.000 description 11
125000004430 oxygen atom Chemical group O* 0.000 description 11
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 10
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 10
239000012317 TBTU Substances 0.000 description 10
150000002431 hydrogen Chemical class 0.000 description 10
230000014759 maintenance of location Effects 0.000 description 10
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 10
229910052760 oxygen Inorganic materials 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 10
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 9
AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 9
208000022821 personality disease Diseases 0.000 description 9
239000012047 saturated solution Substances 0.000 description 9
ACNRTYKOPZDRCO-UHFFFAOYSA-N tert-butyl n-(2-oxoethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCC=O ACNRTYKOPZDRCO-UHFFFAOYSA-N 0.000 description 9
KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
OPEBSOKNWMAPLB-YUMQZZPRSA-N [(7s,9as)-1,3,4,6,7,8,9,9a-octahydropyrazino[2,1-c][1,4]oxazin-7-yl]methanol Chemical compound C1COC[C@@H]2CN[C@H](CO)CN21 OPEBSOKNWMAPLB-YUMQZZPRSA-N 0.000 description 8
229940025084 amphetamine Drugs 0.000 description 8
UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 8
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 8
229910000024 caesium carbonate Inorganic materials 0.000 description 8
RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 8
CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 8
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 8
230000009467 reduction Effects 0.000 description 8
238000006722 reduction reaction Methods 0.000 description 8
239000000932 sedative agent Substances 0.000 description 8
230000001568 sexual effect Effects 0.000 description 8
229910000029 sodium carbonate Inorganic materials 0.000 description 8
YHWMFDLNZGIJSD-UHFFFAOYSA-N 2h-1,4-oxazine Chemical compound C1OC=CN=C1 YHWMFDLNZGIJSD-UHFFFAOYSA-N 0.000 description 7
208000028810 Shared psychotic disease Diseases 0.000 description 7
239000000164 antipsychotic agent Substances 0.000 description 7
229940005529 antipsychotics Drugs 0.000 description 7
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 7
239000006260 foam Substances 0.000 description 7
238000010438 heat treatment Methods 0.000 description 7
229910052717 sulfur Chemical group 0.000 description 7
239000003981 vehicle Substances 0.000 description 7
SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 6
PJJLVZOKOWVMLN-LWOQYNTDSA-N (3r)-3-methyl-3,6,7,8,9,9a-hexahydro-2h-pyrazino[1,2-a]pyrazine-1,4-dione Chemical compound C1NCCN2C(=O)[C@@H](C)NC(=O)C21 PJJLVZOKOWVMLN-LWOQYNTDSA-N 0.000 description 6
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
208000036864 Attention deficit/hyperactivity disease Diseases 0.000 description 6
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 6
208000022497 Cocaine-Related disease Diseases 0.000 description 6
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
208000026251 Opioid-Related disease Diseases 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 6
239000012298 atmosphere Substances 0.000 description 6
239000003638 chemical reducing agent Substances 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
238000005859 coupling reaction Methods 0.000 description 6
229940079593 drug Drugs 0.000 description 6
229910052731 fluorine Inorganic materials 0.000 description 6
239000011737 fluorine Substances 0.000 description 6
QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 description 6
235000019253 formic acid Nutrition 0.000 description 6
239000000380 hallucinogen Substances 0.000 description 6
229960002715 nicotine Drugs 0.000 description 6
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 6
FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 6
239000001301 oxygen Substances 0.000 description 6
230000001624 sedative effect Effects 0.000 description 6
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
208000011117 substance-related disease Diseases 0.000 description 6
208000024891 symptom Diseases 0.000 description 6
238000004704 ultra performance liquid chromatography Methods 0.000 description 6
ZEKMVSOHQJAAHS-PHDIDXHHSA-N (7r,9as)-7-(hydroxymethyl)-2,2-dioxo-1,3,4,7,8,9a-hexahydropyrazino[2,1-c][1,4]thiazine-6,9-dione Chemical compound C1S(=O)(=O)CCN2C(=O)[C@@H](CO)NC(=O)[C@H]21 ZEKMVSOHQJAAHS-PHDIDXHHSA-N 0.000 description 5
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 5
XAUDKMAEBCEBDJ-UHFFFAOYSA-N 1-[3,5-bis(trifluoromethyl)phenyl]-n-[6-chloro-4-(4-fluoro-2-methylphenyl)pyridin-3-yl]cyclopropane-1-carboxamide Chemical compound CC1=CC(F)=CC=C1C1=CC(Cl)=NC=C1NC(=O)C1(C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)CC1 XAUDKMAEBCEBDJ-UHFFFAOYSA-N 0.000 description 5
ZEMZPXWZVTUONV-UHFFFAOYSA-N 2-(2-dicyclohexylphosphanylphenyl)-n,n-dimethylaniline Chemical group CN(C)C1=CC=CC=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 ZEMZPXWZVTUONV-UHFFFAOYSA-N 0.000 description 5
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
208000029197 Amphetamine-Related disease Diseases 0.000 description 5
206010012289 Dementia Diseases 0.000 description 5
206010013654 Drug abuse Diseases 0.000 description 5
208000030814 Eating disease Diseases 0.000 description 5
208000019454 Feeding and Eating disease Diseases 0.000 description 5
206010026749 Mania Diseases 0.000 description 5
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JP2008529564A 2005-09-09 2006-09-07 ピリジン誘導体および精神異常の処置におけるそれらの使用 Active JP5121716B2 (ja)