BG102948A - Пиразинони като инхибитори на тромбин - Google Patents

Info

Publication number

BG102948A

BG102948A BG102948A BG10294898A BG102948A BG 102948 A BG102948 A BG 102948A BG 102948 A BG102948 A BG 102948A BG 10294898 A BG10294898 A BG 10294898A BG 102948 A BG102948 A BG 102948A

Authority

BG

Bulgaria

Prior art keywords

methyl

mammal

amino

cycloalkyl

alkyl

Prior art date

1996-04-23

Links

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• Global Dossier
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• 229940122388 Thrombin inhibitor Drugs 0.000 title abstract description 26
• 239000003868 thrombin inhibitor Substances 0.000 title abstract description 26
• 150000001875 compounds Chemical class 0.000 claims abstract description 190
• 238000000034 method Methods 0.000 claims description 215
• -1 hydroxy, amino Chemical group 0.000 claims description 116
• HUTNOYOBQPAKIA-UHFFFAOYSA-N 1h-pyrazin-2-one Chemical compound OC1=CN=CC=N1 HUTNOYOBQPAKIA-UHFFFAOYSA-N 0.000 claims description 94
• 238000002360 preparation method Methods 0.000 claims description 90
• 239000000203 mixture Substances 0.000 claims description 88
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 72
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 66
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 45
• 239000001257 hydrogen Substances 0.000 claims description 45
• 229910052739 hydrogen Inorganic materials 0.000 claims description 45
• 241000124008 Mammalia Species 0.000 claims description 41
• 125000000217 alkyl group Chemical group 0.000 claims description 37
• 150000003839 salts Chemical class 0.000 claims description 35
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
• 229910052736 halogen Inorganic materials 0.000 claims description 25
• 125000000623 heterocyclic group Chemical group 0.000 claims description 25
• 125000003118 aryl group Chemical group 0.000 claims description 24
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 24
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 24
• 229910052717 sulfur Inorganic materials 0.000 claims description 23
• 208000007536 Thrombosis Diseases 0.000 claims description 22
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
• 150000002367 halogens Chemical class 0.000 claims description 22
• 229910052760 oxygen Inorganic materials 0.000 claims description 22
• 229920006395 saturated elastomer Polymers 0.000 claims description 22
• 239000000460 chlorine Substances 0.000 claims description 20
• 239000002253 acid Substances 0.000 claims description 19
• 230000015572 biosynthetic process Effects 0.000 claims description 19
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
• 125000005842 heteroatom Chemical group 0.000 claims description 17
• 239000002904 solvent Substances 0.000 claims description 17
• NGQIDWQPIXGRGH-UHFFFAOYSA-N 1h-pyrazin-2-one;dihydrochloride Chemical compound Cl.Cl.O=C1C=NC=CN1 NGQIDWQPIXGRGH-UHFFFAOYSA-N 0.000 claims description 16
• GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 16
• 101150065749 Churc1 gene Proteins 0.000 claims description 16
• 102100038239 Protein Churchill Human genes 0.000 claims description 16
• 230000002401 inhibitory effect Effects 0.000 claims description 16
• 150000004682 monohydrates Chemical class 0.000 claims description 16
• 150000002431 hydrogen Chemical group 0.000 claims description 15
• 125000001072 heteroaryl group Chemical group 0.000 claims description 14
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 13
• 239000004480 active ingredient Substances 0.000 claims description 13
• 210000004369 blood Anatomy 0.000 claims description 13
• 239000008280 blood Substances 0.000 claims description 13
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 13
• 238000001990 intravenous administration Methods 0.000 claims description 13
• 229910052757 nitrogen Inorganic materials 0.000 claims description 13
• 125000003545 alkoxy group Chemical group 0.000 claims description 12
• 239000012458 free base Substances 0.000 claims description 12
• 235000019359 magnesium stearate Nutrition 0.000 claims description 12
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 12
• 108090000190 Thrombin Proteins 0.000 claims description 11
• 150000001602 bicycloalkyls Chemical group 0.000 claims description 11
• 239000003814 drug Substances 0.000 claims description 11
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 10
• 229930195725 Mannitol Natural products 0.000 claims description 10
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
• 239000000594 mannitol Substances 0.000 claims description 10
• 235000010355 mannitol Nutrition 0.000 claims description 10
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
• 208000005189 Embolism Diseases 0.000 claims description 9
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 9
• 208000001435 Thromboembolism Diseases 0.000 claims description 9
• 230000001269 cardiogenic effect Effects 0.000 claims description 9
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
• 229960004072 thrombin Drugs 0.000 claims description 9
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
• IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 claims description 7
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 7
• 229940079593 drug Drugs 0.000 claims description 7
• 239000008187 granular material Substances 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• 239000000843 powder Substances 0.000 claims description 7
• 201000001320 Atherosclerosis Diseases 0.000 claims description 6
• JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 claims description 6
• 125000001624 naphthyl group Chemical group 0.000 claims description 6
• 238000003756 stirring Methods 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• 206010002388 Angina unstable Diseases 0.000 claims description 5
• 208000007814 Unstable Angina Diseases 0.000 claims description 5
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 5
• 239000004305 biphenyl Substances 0.000 claims description 5
• 235000010290 biphenyl Nutrition 0.000 claims description 5
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
• 239000006185 dispersion Substances 0.000 claims description 5
• 125000001153 fluoro group Chemical group F* 0.000 claims description 5
• 201000004332 intermediate coronary syndrome Diseases 0.000 claims description 5
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 5
• RGICCULPCWNRAB-UHFFFAOYSA-N 2-[2-(2-hexoxyethoxy)ethoxy]ethanol Chemical compound CCCCCCOCCOCCOCCO RGICCULPCWNRAB-UHFFFAOYSA-N 0.000 claims description 4
• 206010014498 Embolic stroke Diseases 0.000 claims description 4
• 206010014522 Embolism venous Diseases 0.000 claims description 4
• 229920000168 Microcrystalline cellulose Polymers 0.000 claims description 4
• 206010028980 Neoplasm Diseases 0.000 claims description 4
• GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
• AEMOLEFTQBMNLQ-WAXACMCWSA-N alpha-D-glucuronic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-WAXACMCWSA-N 0.000 claims description 4
• 210000001367 artery Anatomy 0.000 claims description 4
• 239000002585 base Substances 0.000 claims description 4
• 230000023555 blood coagulation Effects 0.000 claims description 4
• 239000000872 buffer Substances 0.000 claims description 4
• 201000011510 cancer Diseases 0.000 claims description 4
• 235000010980 cellulose Nutrition 0.000 claims description 4
• 239000001913 cellulose Substances 0.000 claims description 4
• 229920002678 cellulose Polymers 0.000 claims description 4
• 238000007887 coronary angioplasty Methods 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 238000002347 injection Methods 0.000 claims description 4
• 239000007924 injection Substances 0.000 claims description 4
• 239000008108 microcrystalline cellulose Substances 0.000 claims description 4
• 229940016286 microcrystalline cellulose Drugs 0.000 claims description 4
• 235000019813 microcrystalline cellulose Nutrition 0.000 claims description 4
• 208000010125 myocardial infarction Diseases 0.000 claims description 4
• 230000008569 process Effects 0.000 claims description 4
• 239000007790 solid phase Substances 0.000 claims description 4
• 230000003558 thrombophilic effect Effects 0.000 claims description 4
• 208000004043 venous thromboembolism Diseases 0.000 claims description 4
• 206010038563 Reocclusion Diseases 0.000 claims description 3
• IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 claims description 3
• 201000010099 disease Diseases 0.000 claims description 3
• 239000002319 fibrinogen receptor antagonist Substances 0.000 claims description 3
• 229940097043 glucuronic acid Drugs 0.000 claims description 3
• 210000003709 heart valve Anatomy 0.000 claims description 3
• 125000002950 monocyclic group Chemical group 0.000 claims description 3
• 239000002245 particle Substances 0.000 claims description 3
• 238000000634 powder X-ray diffraction Methods 0.000 claims description 3
• 238000000926 separation method Methods 0.000 claims description 3
• 241001631457 Cannula Species 0.000 claims description 2
• 229940126062 Compound A Drugs 0.000 claims description 2
• NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 2
• 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 2
• 235000004431 Linum usitatissimum Nutrition 0.000 claims description 2
• 201000005660 Protein C Deficiency Diseases 0.000 claims description 2
• 208000010378 Pulmonary Embolism Diseases 0.000 claims description 2
• 150000007513 acids Chemical class 0.000 claims description 2
• 230000000747 cardiac effect Effects 0.000 claims description 2
• 206010061592 cardiac fibrillation Diseases 0.000 claims description 2
• 238000002512 chemotherapy Methods 0.000 claims description 2
• 208000035475 disorder Diseases 0.000 claims description 2
• 238000007908 dry granulation Methods 0.000 claims description 2
• 108010091897 factor V Leiden Proteins 0.000 claims description 2
• 238000007429 general method Methods 0.000 claims description 2
• 208000013746 hereditary thrombophilia due to congenital protein C deficiency Diseases 0.000 claims description 2
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
• 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 2
• 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 2
• 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 2
• 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 2
• 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 2
• 208000031225 myocardial ischemia Diseases 0.000 claims description 2
• 239000000049 pigment Substances 0.000 claims description 2
• 239000004408 titanium dioxide Substances 0.000 claims description 2
• 235000010215 titanium dioxide Nutrition 0.000 claims description 2
• 239000008215 water for injection Substances 0.000 claims description 2
• 229920003169 water-soluble polymer Polymers 0.000 claims description 2
• 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims 4
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 3
• 125000005843 halogen group Chemical group 0.000 claims 3
• 230000003595 spectral effect Effects 0.000 claims 2
• 102000004411 Antithrombin III Human genes 0.000 claims 1
• 108090000935 Antithrombin III Proteins 0.000 claims 1
• 206010010774 Constipation Diseases 0.000 claims 1
• 241000208202 Linaceae Species 0.000 claims 1
• 206010051292 Protein S Deficiency Diseases 0.000 claims 1
• 229960005348 antithrombin iii Drugs 0.000 claims 1
• 210000004556 brain Anatomy 0.000 claims 1
• 230000002600 fibrillogenic effect Effects 0.000 claims 1
• 208000019622 heart disease Diseases 0.000 claims 1
• UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims 1
• 230000001732 thrombotic effect Effects 0.000 abstract description 7
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 140
• 239000000243 solution Substances 0.000 description 83
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 75
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 67
• 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 65
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
• 235000019439 ethyl acetate Nutrition 0.000 description 51
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• 239000007787 solid Substances 0.000 description 46
• 235000002639 sodium chloride Nutrition 0.000 description 40
• 150000003840 hydrochlorides Chemical class 0.000 description 36
• VTRSQUIXGXUANF-UHFFFAOYSA-N benzyl 2-(3,5-dichloro-2-methyl-6-oxopyrazin-1-yl)acetate Chemical compound CC1=C(Cl)N=C(Cl)C(=O)N1CC(=O)OCC1=CC=CC=C1 VTRSQUIXGXUANF-UHFFFAOYSA-N 0.000 description 35
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 33
• 239000011734 sodium Substances 0.000 description 32
• 239000011541 reaction mixture Substances 0.000 description 26
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 25
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• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 20
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 18
• 150000001412 amines Chemical class 0.000 description 18
• NRHHSELWZLPJTA-UHFFFAOYSA-N 2-(3,5-dichloro-2-methyl-6-oxopyrazin-1-yl)acetic acid Chemical compound CC1=C(Cl)N=C(Cl)C(=O)N1CC(O)=O NRHHSELWZLPJTA-UHFFFAOYSA-N 0.000 description 17
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 17
• 239000011780 sodium chloride Substances 0.000 description 17
• 239000012044 organic layer Substances 0.000 description 16
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 15
• 238000003818 flash chromatography Methods 0.000 description 15
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• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
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• 238000004458 analytical method Methods 0.000 description 13
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 12
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• 238000001914 filtration Methods 0.000 description 12
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• 230000004048 modification Effects 0.000 description 12
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• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
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• 229960000583 acetic acid Drugs 0.000 description 11
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 10
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• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
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• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 8
• VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 8
• BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 8
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
• 239000000706 filtrate Substances 0.000 description 8
• UKAMHSXPNLVLDB-UHFFFAOYSA-N 2-[6-methyl-2-oxo-3-(2-phenylethylamino)pyrazin-1-yl]acetic acid Chemical compound O=C1N(CC(O)=O)C(C)=CN=C1NCCC1=CC=CC=C1 UKAMHSXPNLVLDB-UHFFFAOYSA-N 0.000 description 7
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• 125000003395 phenylethylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 7
• 229960000103 thrombolytic agent Drugs 0.000 description 7
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• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
• 150000001299 aldehydes Chemical class 0.000 description 6
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• 229940127218 antiplatelet drug Drugs 0.000 description 6
• 229910052786 argon Inorganic materials 0.000 description 6
• 238000003556 assay Methods 0.000 description 6
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• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
• 238000001035 drying Methods 0.000 description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
• 239000012467 final product Substances 0.000 description 6
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 6
• 229910052763 palladium Inorganic materials 0.000 description 6
• 239000000106 platelet aggregation inhibitor Substances 0.000 description 6
• 239000002244 precipitate Substances 0.000 description 6
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
• 239000007858 starting material Substances 0.000 description 6
• 238000003786 synthesis reaction Methods 0.000 description 6
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
• 239000003039 volatile agent Substances 0.000 description 6
• RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 5
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• 108090000790 Enzymes Proteins 0.000 description 5
• XMIIGOLPHOKFCH-UHFFFAOYSA-N beta-phenylpropanoic acid Natural products OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 5
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• 230000005764 inhibitory process Effects 0.000 description 5
• NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 5
• 229910052708 sodium Inorganic materials 0.000 description 5
• 239000000758 substrate Substances 0.000 description 5
• SYJCYUZKILRBSA-UHFFFAOYSA-N tert-butyl n-[5-(aminomethyl)-6-methylpyridin-2-yl]carbamate Chemical compound CC1=NC(NC(=O)OC(C)(C)C)=CC=C1CN SYJCYUZKILRBSA-UHFFFAOYSA-N 0.000 description 5
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