TWI241294B - Novel indole derivatives, processes for their preparation, their use and pharmaceutical compositions containing them - Google Patents

Info

Publication number

TWI241294B

TWI241294B TW087121374A TW87121374A TWI241294B TW I241294 B TWI241294 B TW I241294B TW 087121374 A TW087121374 A TW 087121374A TW 87121374 A TW87121374 A TW 87121374A TW I241294 B TWI241294 B TW I241294B

Authority

TW

Taiwan

Prior art keywords

residue

phenyl

residues

compound

group

Prior art date

1997-12-24

Links

• Espacenet
• Global Dossier
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• 238000000034 method Methods 0.000 title claims abstract description 42
• 238000002360 preparation method Methods 0.000 title abstract description 31
• 150000002475 indoles Chemical class 0.000 title abstract description 16
• 239000008194 pharmaceutical composition Substances 0.000 title abstract description 12
• 229940054051 antipsychotic indole derivative Drugs 0.000 title abstract description 8
• 150000001875 compounds Chemical class 0.000 claims abstract description 352
• 239000000203 mixture Substances 0.000 claims abstract description 133
• 108010074860 Factor Xa Proteins 0.000 claims abstract description 48
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 29
• 239000003814 drug Substances 0.000 claims abstract description 21
• 238000011282 treatment Methods 0.000 claims abstract description 21
• 239000003112 inhibitor Substances 0.000 claims abstract description 19
• 230000023555 blood coagulation Effects 0.000 claims abstract description 16
• 229910052740 iodine Inorganic materials 0.000 claims abstract description 12
• 108010055222 clotting enzyme Proteins 0.000 claims abstract description 4
• 208000001435 Thromboembolism Diseases 0.000 claims abstract description 3
• -1 (CrC4) -alkyl Chemical group 0.000 claims description 276
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 107
• 229910052757 nitrogen Inorganic materials 0.000 claims description 90
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 89
• 125000000217 alkyl group Chemical group 0.000 claims description 71
• 229910052739 hydrogen Inorganic materials 0.000 claims description 63
• 239000001257 hydrogen Substances 0.000 claims description 61
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 52
• 238000006243 chemical reaction Methods 0.000 claims description 49
• 150000003839 salts Chemical class 0.000 claims description 48
• 125000001424 substituent group Chemical group 0.000 claims description 46
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 32
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 25
• 125000004076 pyridyl group Chemical group 0.000 claims description 24
• 229910052794 bromium Inorganic materials 0.000 claims description 22
• 229910052731 fluorine Inorganic materials 0.000 claims description 21
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
• 125000001624 naphthyl group Chemical group 0.000 claims description 19
• 125000003545 alkoxy group Chemical group 0.000 claims description 18
• 239000000460 chlorine Substances 0.000 claims description 18
• 125000000623 heterocyclic group Chemical group 0.000 claims description 18
• 229910052801 chlorine Inorganic materials 0.000 claims description 17
• 208000007536 Thrombosis Diseases 0.000 claims description 16
• 150000002431 hydrogen Chemical group 0.000 claims description 16
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
• 229910052799 carbon Inorganic materials 0.000 claims description 13
• 230000002079 cooperative effect Effects 0.000 claims description 12
• 239000007789 gas Substances 0.000 claims description 12
• 150000001450 anions Chemical class 0.000 claims description 9
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• 239000001301 oxygen Substances 0.000 claims description 9
• 230000002265 prevention Effects 0.000 claims description 9
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
• 125000000304 alkynyl group Chemical group 0.000 claims description 8
• 238000006467 substitution reaction Methods 0.000 claims description 8
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
• 150000002500 ions Chemical class 0.000 claims description 7
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
• 229910052717 sulfur Inorganic materials 0.000 claims description 7
• 239000011593 sulfur Substances 0.000 claims description 7
• 229940123583 Factor Xa inhibitor Drugs 0.000 claims description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
• 240000007594 Oryza sativa Species 0.000 claims description 4
• 235000007164 Oryza sativa Nutrition 0.000 claims description 4
• 125000002843 carboxylic acid group Chemical group 0.000 claims description 4
• 239000011737 fluorine Substances 0.000 claims description 4
• 125000005842 heteroatom Chemical group 0.000 claims description 4
• 235000009566 rice Nutrition 0.000 claims description 4
• 206010002383 Angina Pectoris Diseases 0.000 claims description 3
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
• 208000005189 Embolism Diseases 0.000 claims description 3
• 125000001153 fluoro group Chemical group F* 0.000 claims description 3
• 208000010125 myocardial infarction Diseases 0.000 claims description 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
• 229940125898 compound 5 Drugs 0.000 claims description 2
• 230000029087 digestion Effects 0.000 claims description 2
• 239000010977 jade Substances 0.000 claims description 2
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
• PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims 2
• PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims 2
• 235000021286 stilbenes Nutrition 0.000 claims 2
• 230000001079 digestive effect Effects 0.000 claims 1
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
• 208000037803 restenosis Diseases 0.000 claims 1
• 210000003296 saliva Anatomy 0.000 claims 1
• 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
• 230000000694 effects Effects 0.000 abstract description 47
• 239000000126 substance Substances 0.000 abstract description 34
• 201000010099 disease Diseases 0.000 abstract description 15
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 15
• 230000005764 inhibitory process Effects 0.000 abstract description 14
• 239000003937 drug carrier Substances 0.000 abstract description 8
• 101000882917 Penaeus paulensis Hemolymph clottable protein Proteins 0.000 abstract description 2
• 238000011321 prophylaxis Methods 0.000 abstract 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 267
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 241
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 174
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 155
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 146
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 144
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 143
• 239000002253 acid Substances 0.000 description 125
• 239000000047 product Substances 0.000 description 121
• 238000002844 melting Methods 0.000 description 120
• 230000008018 melting Effects 0.000 description 120
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 105
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 95
• 239000000243 solution Substances 0.000 description 91
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 87
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 87
• 238000004949 mass spectrometry Methods 0.000 description 77
• 238000011049 filling Methods 0.000 description 73
• 125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 description 63
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 62
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 60
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 58
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 57
• 239000011347 resin Substances 0.000 description 55
• 229920005989 resin Polymers 0.000 description 55
• 235000011054 acetic acid Nutrition 0.000 description 49
• 150000001412 amines Chemical class 0.000 description 49
• 239000002904 solvent Substances 0.000 description 48
• 238000000354 decomposition reaction Methods 0.000 description 47
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 46
• 239000013078 crystal Substances 0.000 description 46
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 42
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 37
• 238000003818 flash chromatography Methods 0.000 description 37
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 33
• 238000004128 high performance liquid chromatography Methods 0.000 description 33
• 239000005695 Ammonium acetate Substances 0.000 description 31
• 229940043376 ammonium acetate Drugs 0.000 description 31
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 30
• 235000019257 ammonium acetate Nutrition 0.000 description 30
• USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 29
• 239000000463 material Substances 0.000 description 29
• 239000011541 reaction mixture Substances 0.000 description 29
• 238000012360 testing method Methods 0.000 description 29
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 28
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 28
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 28
• 239000012044 organic layer Substances 0.000 description 28
• 239000000741 silica gel Substances 0.000 description 28
• 229910002027 silica gel Inorganic materials 0.000 description 28
• 239000013058 crude material Substances 0.000 description 27
• 230000014759 maintenance of location Effects 0.000 description 27
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 26
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 26
• 239000007858 starting material Substances 0.000 description 25
• 238000003756 stirring Methods 0.000 description 24
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 23
• HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 description 22
• 125000003118 aryl group Chemical group 0.000 description 22
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 22
• 238000010998 test method Methods 0.000 description 22
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
• RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 21
• 229910000037 hydrogen sulfide Inorganic materials 0.000 description 21
• 239000007787 solid Substances 0.000 description 21
• 102000004190 Enzymes Human genes 0.000 description 20
• 108090000790 Enzymes Proteins 0.000 description 20
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 20
• 239000003153 chemical reaction reagent Substances 0.000 description 20
• 229940088598 enzyme Drugs 0.000 description 20
• WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 20
• 230000015572 biosynthetic process Effects 0.000 description 19
• 239000003795 chemical substances by application Substances 0.000 description 19
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 19
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 19
• 230000015271 coagulation Effects 0.000 description 18
• 238000005345 coagulation Methods 0.000 description 18
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 18
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 17
• 239000002585 base Substances 0.000 description 17
• 125000004093 cyano group Chemical group *C#N 0.000 description 17
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 17
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 15
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 15
• 108090000190 Thrombin Proteins 0.000 description 15
• 150000002148 esters Chemical class 0.000 description 15
• 239000005457 ice water Substances 0.000 description 15
• 239000011159 matrix material Substances 0.000 description 15
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 15
• 229910000029 sodium carbonate Inorganic materials 0.000 description 15
• 238000003786 synthesis reaction Methods 0.000 description 15
• 229960004072 thrombin Drugs 0.000 description 15
• CVKOOKPNCVYHNY-UHFFFAOYSA-N 3-(bromomethyl)benzonitrile Chemical compound BrCC1=CC=CC(C#N)=C1 CVKOOKPNCVYHNY-UHFFFAOYSA-N 0.000 description 14
• HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 14
• 239000007788 liquid Substances 0.000 description 14
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 13
• 125000002946 cyanobenzyl group Chemical group 0.000 description 13
• 238000010494 dissociation reaction Methods 0.000 description 13
• 230000005593 dissociations Effects 0.000 description 13
• 229960002897 heparin Drugs 0.000 description 13
• 229920000669 heparin Polymers 0.000 description 13
• 150000003254 radicals Chemical class 0.000 description 13
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 12
• 239000007864 aqueous solution Substances 0.000 description 12
• 125000000524 functional group Chemical group 0.000 description 12
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 11
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
• 125000003342 alkenyl group Chemical group 0.000 description 11
• 239000000543 intermediate Substances 0.000 description 11
• 239000010410 layer Substances 0.000 description 11
• 238000004366 reverse phase liquid chromatography Methods 0.000 description 11
• 229920006395 saturated elastomer Polymers 0.000 description 11
• 238000001308 synthesis method Methods 0.000 description 11
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 10
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
• 125000003277 amino group Chemical group 0.000 description 10
• 150000001540 azides Chemical class 0.000 description 10
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 10
• DXPIZCZNFUTPEI-UHFFFAOYSA-O diphenylphosphanium;azide Chemical compound [N-]=[N+]=[N-].C=1C=CC=CC=1[PH2+]C1=CC=CC=C1 DXPIZCZNFUTPEI-UHFFFAOYSA-O 0.000 description 10
• 229940079593 drug Drugs 0.000 description 10
• 229920001223 polyethylene glycol Polymers 0.000 description 10
• 239000002244 precipitate Substances 0.000 description 10
• 239000002243 precursor Substances 0.000 description 10
• 238000002953 preparative HPLC Methods 0.000 description 10
• 238000000746 purification Methods 0.000 description 10
• 238000010992 reflux Methods 0.000 description 10
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 9
• 108010094028 Prothrombin Proteins 0.000 description 9
• 102100027378 Prothrombin Human genes 0.000 description 9
• 239000012043 crude product Substances 0.000 description 9
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 9
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 9
• 229940039716 prothrombin Drugs 0.000 description 9
• 239000011721 thiamine Substances 0.000 description 9
• ZZAVIQXQBBOHBB-UHFFFAOYSA-N 4-methoxy-1h-indole-2-carboxylic acid Chemical compound COC1=CC=CC2=C1C=C(C(O)=O)N2 ZZAVIQXQBBOHBB-UHFFFAOYSA-N 0.000 description 8
• ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
• 108010000499 Thromboplastin Proteins 0.000 description 8
• 102000002262 Thromboplastin Human genes 0.000 description 8
• 210000004369 blood Anatomy 0.000 description 8
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• 238000004587 chromatography analysis Methods 0.000 description 8
• 238000002425 crystallisation Methods 0.000 description 8
• 230000008025 crystallization Effects 0.000 description 8
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 8
• 238000001035 drying Methods 0.000 description 8
• 239000012312 sodium hydride Substances 0.000 description 8
• 229910000104 sodium hydride Inorganic materials 0.000 description 8
• 238000010561 standard procedure Methods 0.000 description 8
• 229960003495 thiamine Drugs 0.000 description 8
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
• LRXFKKPEBXIPMW-UHFFFAOYSA-N 2-(9h-fluoren-2-yl)propanoic acid Chemical compound C1=CC=C2C3=CC=C(C(C(O)=O)C)C=C3CC2=C1 LRXFKKPEBXIPMW-UHFFFAOYSA-N 0.000 description 7
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 7
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 7
• PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 7
• 241000282414 Homo sapiens Species 0.000 description 7
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 7
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 7
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
• 125000004432 carbon atom Chemical group C* 0.000 description 7
• 238000001816 cooling Methods 0.000 description 7
• 238000010790 dilution Methods 0.000 description 7
• 239000012895 dilution Substances 0.000 description 7
• 125000004185 ester group Chemical group 0.000 description 7
• 125000001041 indolyl group Chemical group 0.000 description 7
• 238000002347 injection Methods 0.000 description 7
• 239000007924 injection Substances 0.000 description 7
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
• 230000037361 pathway Effects 0.000 description 7
• 125000006239 protecting group Chemical group 0.000 description 7
• 238000006722 reduction reaction Methods 0.000 description 7
• 239000011780 sodium chloride Substances 0.000 description 7
• 239000003826 tablet Substances 0.000 description 7
• 239000000052 vinegar Substances 0.000 description 7
• 235000021419 vinegar Nutrition 0.000 description 7
• VFHUJFBEFDVZPJ-UHFFFAOYSA-N 1h-indole-2-carboxamide Chemical compound C1=CC=C2NC(C(=O)N)=CC2=C1 VFHUJFBEFDVZPJ-UHFFFAOYSA-N 0.000 description 6
• JZRWCGZRTZMZEH-UHFFFAOYSA-N Thiamine Natural products CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 description 6
• 150000007513 acids Chemical class 0.000 description 6
• 230000004913 activation Effects 0.000 description 6
• 230000033228 biological regulation Effects 0.000 description 6
• 239000000872 buffer Substances 0.000 description 6
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