DD235872A5 - Verfahren zur herstellung von benzo-(pyrano und thiopyrano)-pyridine - Google Patents

Info

Publication number

DD235872A5

DD235872A5 DD85276081A DD27608185A DD235872A5 DD 235872 A5 DD235872 A5 DD 235872A5 DD 85276081 A DD85276081 A DD 85276081A DD 27608185 A DD27608185 A DD 27608185A DD 235872 A5 DD235872 A5 DD 235872A5

Authority

DD

German Democratic Republic

Prior art keywords

alkyl

hydroxy

formula

ring

compounds

Prior art date

1984-05-10

Links

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• 238000004519 manufacturing process Methods 0.000 title description 2
• RQMWVVBHJMUJNZ-UHFFFAOYSA-N 4-chloropyridin-2-amine Chemical compound NC1=CC(Cl)=CC=N1 RQMWVVBHJMUJNZ-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 176
• 238000000034 method Methods 0.000 claims abstract description 58
• 150000003839 salts Chemical class 0.000 claims abstract description 55
• 239000001257 hydrogen Substances 0.000 claims abstract description 46
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 46
• 125000001424 substituent group Chemical group 0.000 claims abstract description 39
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 28
• 230000008569 process Effects 0.000 claims abstract description 28
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 26
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 26
• 239000001301 oxygen Substances 0.000 claims abstract description 26
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 24
• 125000004423 acyloxy group Chemical group 0.000 claims abstract description 23
• 150000002367 halogens Chemical class 0.000 claims abstract description 23
• 238000002360 preparation method Methods 0.000 claims abstract description 19
• 150000002431 hydrogen Chemical group 0.000 claims abstract description 16
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 15
• 229910052717 sulfur Chemical group 0.000 claims abstract description 15
• 239000011593 sulfur Chemical group 0.000 claims abstract description 15
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 12
• 125000004442 acylamino group Chemical group 0.000 claims abstract description 10
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 9
• 201000010099 disease Diseases 0.000 claims abstract description 5
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 5
• 239000003814 drug Substances 0.000 claims abstract description 3
• 125000005605 benzo group Chemical group 0.000 claims abstract 3
• 150000003222 pyridines Chemical class 0.000 claims abstract 3
• -1 d-7-alkoxycarbonyl Chemical group 0.000 claims description 77
• 239000000203 mixture Substances 0.000 claims description 68
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 28
• 230000002829 reductive effect Effects 0.000 claims description 24
• 239000003638 chemical reducing agent Substances 0.000 claims description 17
• 125000000217 alkyl group Chemical group 0.000 claims description 16
• 125000004432 carbon atom Chemical group C* 0.000 claims description 14
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
• 125000005042 acyloxymethyl group Chemical group 0.000 claims description 9
• 125000005333 aroyloxy group Chemical group 0.000 claims description 9
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 9
• 125000000524 functional group Chemical group 0.000 claims description 8
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 7
• 210000003169 central nervous system Anatomy 0.000 claims description 7
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
• 208000028017 Psychotic disease Diseases 0.000 claims description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
• 208000020401 Depressive disease Diseases 0.000 claims description 5
• 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 5
• 210000004556 brain Anatomy 0.000 claims description 5
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 5
• 230000000701 neuroleptic effect Effects 0.000 claims description 5
• 230000003287 optical effect Effects 0.000 claims description 5
• 150000007524 organic acids Chemical class 0.000 claims description 5
• 239000003153 chemical reaction reagent Substances 0.000 claims description 4
• 230000008030 elimination Effects 0.000 claims description 4
• 238000003379 elimination reaction Methods 0.000 claims description 4
• 150000007522 mineralic acids Chemical class 0.000 claims description 4
• 239000003176 neuroleptic agent Substances 0.000 claims description 4
• 239000004089 psychotropic agent Substances 0.000 claims description 4
• 208000019901 Anxiety disease Diseases 0.000 claims description 3
• 230000001430 anti-depressive effect Effects 0.000 claims description 3
• 239000000935 antidepressant agent Substances 0.000 claims description 3
• 230000036506 anxiety Effects 0.000 claims description 3
• 125000003118 aryl group Chemical group 0.000 claims description 3
• 230000007812 deficiency Effects 0.000 claims description 3
• 229940001470 psychoactive drug Drugs 0.000 claims description 3
• 239000003368 psychostimulant agent Substances 0.000 claims description 3
• GSLWRDKYYIQKIM-TZMCWYRMSA-N (4as,10br)-4-propyl-1,2,3,4a,5,10b-hexahydrochromeno[3,4-b]pyridin-9-ol Chemical compound C1=C(O)C=C2[C@H]3CCCN(CCC)[C@@H]3COC2=C1 GSLWRDKYYIQKIM-TZMCWYRMSA-N 0.000 claims description 2
• 208000008589 Obesity Diseases 0.000 claims description 2
• 150000001450 anions Chemical class 0.000 claims description 2
• 229940005513 antidepressants Drugs 0.000 claims description 2
• 230000007278 cognition impairment Effects 0.000 claims description 2
• 238000010511 deprotection reaction Methods 0.000 claims description 2
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 235000020824 obesity Nutrition 0.000 claims description 2
• 230000000144 pharmacologic effect Effects 0.000 claims description 2
• 230000001003 psychopharmacologic effect Effects 0.000 claims description 2
• 230000009257 reactivity Effects 0.000 claims description 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 13
• KNTIRDWFHBETOO-UHFFFAOYSA-N 4h-chromeno[3,4-b]pyridine Chemical compound C1=CC=C2C3=CC=CNC3=COC2=C1 KNTIRDWFHBETOO-UHFFFAOYSA-N 0.000 claims 2
• YPJUXORKYFQSQP-UONOGXRCSA-N (4aS,10bR)-10-ethoxy-4-propyl-1,2,3,4a,5,10b-hexahydrochromeno[3,4-b]pyridine Chemical compound C(C)OC1=CC=CC2=C1[C@@H]1[C@H](N(CCC1)CCC)CO2 YPJUXORKYFQSQP-UONOGXRCSA-N 0.000 claims 1
• HVJVYKLJJCMEFE-TZMCWYRMSA-N (4aS,10bR)-7-ethoxy-4,8-dimethyl-1,2,3,4a,5,10b-hexahydrochromeno[3,4-b]pyridine Chemical compound C(C)OC1=C(C=CC2=C1OC[C@H]1N(CCC[C@@H]12)C)C HVJVYKLJJCMEFE-TZMCWYRMSA-N 0.000 claims 1
• RVISITFMLATVSR-DGCLKSJQSA-N (4aS,10bR)-7-methoxy-4,8-dimethyl-1,2,3,4a,5,10b-hexahydrochromeno[3,4-b]pyridine Chemical compound C([C@@H]12)CCN(C)[C@@H]1COC1=C2C=CC(C)=C1OC RVISITFMLATVSR-DGCLKSJQSA-N 0.000 claims 1
• 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 1
• BXSPQBOQCWIFMX-UHFFFAOYSA-N 4h-thiochromeno[3,4-b]pyridine Chemical class C1=CC=C2C3=CC=CNC3=CSC2=C1 BXSPQBOQCWIFMX-UHFFFAOYSA-N 0.000 claims 1
• 125000005530 alkylenedioxy group Chemical group 0.000 claims 1
• 230000036528 appetite Effects 0.000 claims 1
• 235000019789 appetite Nutrition 0.000 claims 1
• 230000001149 cognitive effect Effects 0.000 claims 1
• 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 43
• 125000006701 (C1-C7) alkyl group Chemical group 0.000 abstract 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 91
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 87
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 82
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 56
• 239000000243 solution Substances 0.000 description 55
• 239000002904 solvent Substances 0.000 description 52
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 47
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 46
• 239000000047 product Substances 0.000 description 42
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
• 239000007858 starting material Substances 0.000 description 36
• 238000006243 chemical reaction Methods 0.000 description 35
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 32
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 28
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 22
• AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 22
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
• 150000003254 radicals Chemical class 0.000 description 20
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 19
• 238000001035 drying Methods 0.000 description 18
• 239000002253 acid Substances 0.000 description 17
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 17
• 230000009467 reduction Effects 0.000 description 17
• 238000006722 reduction reaction Methods 0.000 description 17
• 239000002585 base Substances 0.000 description 16
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 16
• 235000019341 magnesium sulphate Nutrition 0.000 description 16
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
• 229910052740 iodine Inorganic materials 0.000 description 14
• 230000003518 presynaptic effect Effects 0.000 description 14
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
• 239000003054 catalyst Substances 0.000 description 12
• 230000000694 effects Effects 0.000 description 12
• 239000000725 suspension Substances 0.000 description 12
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 11
• 238000009833 condensation Methods 0.000 description 11
• 230000005494 condensation Effects 0.000 description 11
• 239000012280 lithium aluminium hydride Substances 0.000 description 11
• 125000006239 protecting group Chemical group 0.000 description 11
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
• 102000015554 Dopamine receptor Human genes 0.000 description 10
• 108050004812 Dopamine receptor Proteins 0.000 description 10
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
• 239000000741 silica gel Substances 0.000 description 9
• 229910002027 silica gel Inorganic materials 0.000 description 9
• RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 9
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
• 241000124008 Mammalia Species 0.000 description 8
• 238000010790 dilution Methods 0.000 description 8
• 239000012895 dilution Substances 0.000 description 8
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
• SHHLMGCHMMCOOS-UHFFFAOYSA-N 4h-chromen-3-one Chemical class C1=CC=C2CC(=O)COC2=C1 SHHLMGCHMMCOOS-UHFFFAOYSA-N 0.000 description 7
• 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 7
• 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 7
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 7
• 125000002252 acyl group Chemical group 0.000 description 7
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
• 229910052794 bromium Inorganic materials 0.000 description 7
• 230000008025 crystallization Effects 0.000 description 7
• 150000002148 esters Chemical class 0.000 description 7
• 239000000543 intermediate Substances 0.000 description 7
• 229910052987 metal hydride Inorganic materials 0.000 description 7
• 150000004681 metal hydrides Chemical class 0.000 description 7
• 229960003742 phenol Drugs 0.000 description 7
• 238000003756 stirring Methods 0.000 description 7
• KLYMTKVJYHTFIA-UHFFFAOYSA-N 4h-thiochromen-3-one Chemical class C1=CC=C2CC(=O)CSC2=C1 KLYMTKVJYHTFIA-UHFFFAOYSA-N 0.000 description 6
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• 229920002472 Starch Polymers 0.000 description 6
• 229960000583 acetic acid Drugs 0.000 description 6
• 239000004480 active ingredient Substances 0.000 description 6
• 229910052783 alkali metal Inorganic materials 0.000 description 6
• 238000001816 cooling Methods 0.000 description 6
• 238000002425 crystallisation Methods 0.000 description 6
• VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 6
• 239000000706 filtrate Substances 0.000 description 6
• 239000012458 free base Substances 0.000 description 6
• 238000005984 hydrogenation reaction Methods 0.000 description 6
• 239000012442 inert solvent Substances 0.000 description 6
• 239000002798 polar solvent Substances 0.000 description 6
• 102000005962 receptors Human genes 0.000 description 6
• 108020003175 receptors Proteins 0.000 description 6
• 238000010992 reflux Methods 0.000 description 6
• 235000019698 starch Nutrition 0.000 description 6
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 5
• YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 5
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
• 229910021529 ammonia Inorganic materials 0.000 description 5
• 239000008346 aqueous phase Substances 0.000 description 5
• 239000003136 dopamine receptor stimulating agent Substances 0.000 description 5
• 150000002081 enamines Chemical class 0.000 description 5
• 239000000284 extract Substances 0.000 description 5
• 238000010438 heat treatment Methods 0.000 description 5
• 238000000338 in vitro Methods 0.000 description 5
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
• 239000003921 oil Substances 0.000 description 5
• 239000012074 organic phase Substances 0.000 description 5
• 230000020477 pH reduction Effects 0.000 description 5
• 239000000825 pharmaceutical preparation Substances 0.000 description 5
• 239000011734 sodium Substances 0.000 description 5
• 229910052708 sodium Inorganic materials 0.000 description 5
• 235000015424 sodium Nutrition 0.000 description 5
• 229910000029 sodium carbonate Inorganic materials 0.000 description 5
• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 5
• 239000012312 sodium hydride Substances 0.000 description 5
• 229910000104 sodium hydride Inorganic materials 0.000 description 5
• 239000008107 starch Substances 0.000 description 5
• 230000000638 stimulation Effects 0.000 description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
• NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical class CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
• 241000700159 Rattus Species 0.000 description 4
• 239000013543 active substance Substances 0.000 description 4
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
• UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical class NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 4
• WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
• 238000009903 catalytic hydrogenation reaction Methods 0.000 description 4
• FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 4
• 238000000354 decomposition reaction Methods 0.000 description 4
• GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 4
• 238000001914 filtration Methods 0.000 description 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
• 238000001727 in vivo Methods 0.000 description 4
• 235000019359 magnesium stearate Nutrition 0.000 description 4
• 229910052763 palladium Inorganic materials 0.000 description 4
• 150000002989 phenols Chemical class 0.000 description 4
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
• 230000000506 psychotropic effect Effects 0.000 description 4
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
• 235000017557 sodium bicarbonate Nutrition 0.000 description 4
• 239000012279 sodium borohydride Substances 0.000 description 4
• 229910000033 sodium borohydride Inorganic materials 0.000 description 4
• 239000000126 substance Substances 0.000 description 4
• OCQAXYHNMWVLRH-UHFFFAOYSA-N 2,3-dibenzoyl-2,3-dihydroxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)C(O)(C(O)=O)C(O)(C(=O)O)C(=O)C1=CC=CC=C1 OCQAXYHNMWVLRH-UHFFFAOYSA-N 0.000 description 3
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