HUT61747A - Process for producing 5-member-heterocyclic compounds and pharmaceutical compositions comprising same - Google Patents

Info

Publication number

HUT61747A

HUT61747A HU9202450A HU9202450A HUT61747A HU T61747 A HUT61747 A HU T61747A HU 9202450 A HU9202450 A HU 9202450A HU 9202450 A HU9202450 A HU 9202450A HU T61747 A HUT61747 A HU T61747A

Authority

HU

Hungary

Prior art keywords

group

formula

substituted

ring

alkyl

Prior art date

1991-07-27

Links

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• 238000000034 method Methods 0.000 title claims description 18
• 230000008569 process Effects 0.000 title claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 title claims description 3
• -1 aralkoxycarbonyl Chemical group 0.000 claims description 414
• 150000001875 compounds Chemical class 0.000 claims description 168
• RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 122
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 100
• 229910052757 nitrogen Inorganic materials 0.000 claims description 91
• 125000000217 alkyl group Chemical group 0.000 claims description 79
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 75
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 62
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 58
• 238000006243 chemical reaction Methods 0.000 claims description 55
• 125000003545 alkoxy group Chemical group 0.000 claims description 52
• 125000001072 heteroaryl group Chemical group 0.000 claims description 51
• 125000004432 carbon atom Chemical group C* 0.000 claims description 47
• 229910052717 sulfur Inorganic materials 0.000 claims description 46
• 125000003118 aryl group Chemical group 0.000 claims description 45
• 238000002360 preparation method Methods 0.000 claims description 45
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 44
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 41
• 239000000203 mixture Substances 0.000 claims description 41
• 125000000623 heterocyclic group Chemical group 0.000 claims description 40
• 239000011541 reaction mixture Substances 0.000 claims description 39
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 38
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 34
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 32
• 239000004305 biphenyl Substances 0.000 claims description 32
• 239000011593 sulfur Substances 0.000 claims description 32
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 31
• 150000003839 salts Chemical class 0.000 claims description 31
• 239000001257 hydrogen Substances 0.000 claims description 30
• 229910052739 hydrogen Inorganic materials 0.000 claims description 30
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 30
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 30
• 125000002947 alkylene group Chemical group 0.000 claims description 28
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 28
• 239000000460 chlorine Substances 0.000 claims description 28
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 27
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 27
• 229910052760 oxygen Inorganic materials 0.000 claims description 27
• 239000001301 oxygen Substances 0.000 claims description 27
• 239000000126 substance Substances 0.000 claims description 27
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 26
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 26
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 26
• 229910052801 chlorine Inorganic materials 0.000 claims description 26
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
• 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims description 25
• 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 24
• 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 24
• 239000002253 acid Substances 0.000 claims description 23
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
• 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 23
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 22
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 22
• 229910052794 bromium Inorganic materials 0.000 claims description 22
• 229910052731 fluorine Inorganic materials 0.000 claims description 22
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 21
• 150000001721 carbon Chemical group 0.000 claims description 20
• 229910052799 carbon Inorganic materials 0.000 claims description 20
• 125000005576 pyrimidinylene group Chemical group 0.000 claims description 20
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 19
• 125000004647 alkyl sulfenyl group Chemical group 0.000 claims description 19
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 19
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 18
• 125000004450 alkenylene group Chemical group 0.000 claims description 18
• 125000003277 amino group Chemical group 0.000 claims description 18
• 125000005550 pyrazinylene group Chemical group 0.000 claims description 18
• 125000005551 pyridylene group Chemical group 0.000 claims description 18
• 125000001424 substituent group Chemical group 0.000 claims description 18
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
• 239000011737 fluorine Substances 0.000 claims description 16
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 14
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 14
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 13
• 125000005140 aralkylsulfonyl group Chemical group 0.000 claims description 13
• 125000004429 atom Chemical group 0.000 claims description 13
• 125000001246 bromo group Chemical group Br* 0.000 claims description 13
• 125000005842 heteroatom Chemical group 0.000 claims description 13
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 13
• 239000004480 active ingredient Substances 0.000 claims description 12
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 12
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 11
• 125000001589 carboacyl group Chemical group 0.000 claims description 11
• 125000001153 fluoro group Chemical group F* 0.000 claims description 11
• 230000000269 nucleophilic effect Effects 0.000 claims description 11
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
• 150000003254 radicals Chemical class 0.000 claims description 10
• 229920006395 saturated elastomer Polymers 0.000 claims description 10
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 9
• 150000007522 mineralic acids Chemical class 0.000 claims description 9
• 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 8
• KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 claims description 8
• 150000007524 organic acids Chemical class 0.000 claims description 8
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 8
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
• HMXQIFUGFZEJEO-UHFFFAOYSA-N 1,2-dihydropyrrol-3-one Chemical compound O=C1CNC=C1 HMXQIFUGFZEJEO-UHFFFAOYSA-N 0.000 claims description 7
• RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 7
• 125000004956 cyclohexylene group Chemical group 0.000 claims description 7
• 150000002148 esters Chemical class 0.000 claims description 7
• 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims description 7
• ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 claims description 7
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 6
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical class C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 6
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 6
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
• 238000007327 hydrogenolysis reaction Methods 0.000 claims description 6
• 150000002466 imines Chemical class 0.000 claims description 6
• 125000005835 indanylene group Chemical group 0.000 claims description 6
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
• 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 6
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 5
• 125000003435 aroyl group Chemical group 0.000 claims description 5
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 5
• 235000010290 biphenyl Nutrition 0.000 claims description 5
• 125000004122 cyclic group Chemical group 0.000 claims description 5
• 230000008030 elimination Effects 0.000 claims description 5
• 238000003379 elimination reaction Methods 0.000 claims description 5
• 230000007062 hydrolysis Effects 0.000 claims description 5
• 238000006460 hydrolysis reaction Methods 0.000 claims description 5
• 230000002829 reductive effect Effects 0.000 claims description 5
• 125000004434 sulfur atom Chemical group 0.000 claims description 5
• 150000003536 tetrazoles Chemical class 0.000 claims description 5
• 125000005558 triazinylene group Chemical group 0.000 claims description 5
• 125000006833 (C1-C5) alkylene group Chemical group 0.000 claims description 4
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
• IMLSAISZLJGWPP-UHFFFAOYSA-N 1,3-dithiolane Chemical group C1CSCS1 IMLSAISZLJGWPP-UHFFFAOYSA-N 0.000 claims description 4
• ARGCQEVBJHPOGB-UHFFFAOYSA-N 2,5-dihydrofuran Chemical compound C1OCC=C1 ARGCQEVBJHPOGB-UHFFFAOYSA-N 0.000 claims description 4
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
• 125000002252 acyl group Chemical group 0.000 claims description 4
• 125000003282 alkyl amino group Chemical group 0.000 claims description 4
• 125000004414 alkyl thio group Chemical group 0.000 claims description 4
• 150000001412 amines Chemical class 0.000 claims description 4
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 4
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
• JICXRCOSKQBGPZ-UHFFFAOYSA-N methyl 3-[1-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]imidazol-4-yl]propanoate Chemical compound C1=NC(CCC(=O)OC)=CN1C1=CC=C(C=2C=CC(=CC=2)C(N)=N)N=N1 JICXRCOSKQBGPZ-UHFFFAOYSA-N 0.000 claims description 4
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
• 125000001624 naphthyl group Chemical group 0.000 claims description 4
• 235000005985 organic acids Nutrition 0.000 claims description 4
• 125000002755 pyrazolinyl group Chemical group 0.000 claims description 4
• 125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 claims description 3
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 3
• 150000002391 heterocyclic compounds Chemical class 0.000 claims description 3
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 3
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 3
• 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 3
• 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 3
• 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 3
• MUZIZEZCKKMZRT-UHFFFAOYSA-N 1,2-dithiolane Chemical compound C1CSSC1 MUZIZEZCKKMZRT-UHFFFAOYSA-N 0.000 claims description 2
• FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical class C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 2
• MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical class C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 claims description 2
• OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical class C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 2
• QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical class C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 2
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 2
• OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 claims description 2
• KEQTWHPMSVAFDA-UHFFFAOYSA-N 2,3-dihydro-1h-pyrazole Chemical compound C1NNC=C1 KEQTWHPMSVAFDA-UHFFFAOYSA-N 0.000 claims description 2
• JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 claims description 2
• MPTKDOQUXZAHPJ-UHFFFAOYSA-N 2,3-dihydroindazole Chemical compound C1=CC=C2CN[N]C2=C1 MPTKDOQUXZAHPJ-UHFFFAOYSA-N 0.000 claims description 2
• WURYWHAKEJHAOV-UHFFFAOYSA-N 2,5-dihydrothiophene Chemical compound C1SCC=C1 WURYWHAKEJHAOV-UHFFFAOYSA-N 0.000 claims description 2
• IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims description 2
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
• VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims description 2
• ZFJXQZDHZQNHNA-UHFFFAOYSA-N 3-[1-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]imidazol-4-yl]propanoic acid Chemical compound C1=CC(C(=N)N)=CC=C1C1=CC=C(N2C=C(CCC(O)=O)N=C2)N=N1 ZFJXQZDHZQNHNA-UHFFFAOYSA-N 0.000 claims description 2
• MCGBIXXDQFWVDW-UHFFFAOYSA-N 4,5-dihydro-1h-pyrazole Chemical compound C1CC=NN1 MCGBIXXDQFWVDW-UHFFFAOYSA-N 0.000 claims description 2
• NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 2
• XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 2
• WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 2
• WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims description 2
• 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
• 238000010306 acid treatment Methods 0.000 claims description 2
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 2
• 108010026152 alpha-amanitinylazobenzoylglycylglycine Proteins 0.000 claims description 2
• 150000001450 anions Chemical class 0.000 claims description 2
• 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 2
• MXMZCLLIUQEKSN-UHFFFAOYSA-N benzimidazoline Chemical compound C1=CC=C2NCNC2=C1 MXMZCLLIUQEKSN-UHFFFAOYSA-N 0.000 claims description 2
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
• 239000003085 diluting agent Substances 0.000 claims description 2
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
• MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 2
• QNLOWBMKUIXCOW-UHFFFAOYSA-N indol-2-one Chemical compound C1=CC=CC2=NC(=O)C=C21 QNLOWBMKUIXCOW-UHFFFAOYSA-N 0.000 claims description 2
• LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 claims description 2
• GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims description 2
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical class C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 2
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
• LIOPJDZQFZLCEL-UHFFFAOYSA-N methyl 3-[4-[4-(4-carbamimidoylphenyl)-1-methylimidazol-2-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=NC(C=2C=CC(=CC=2)C(N)=N)=CN1C LIOPJDZQFZLCEL-UHFFFAOYSA-N 0.000 claims description 2
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 2
• 125000004076 pyridyl group Chemical group 0.000 claims description 2
• 238000006798 ring closing metathesis reaction Methods 0.000 claims description 2
• 125000006633 tert-butoxycarbonylamino group Chemical group 0.000 claims description 2
• RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 claims description 2
• ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 claims description 2
• 150000003557 thiazoles Chemical class 0.000 claims description 2
• CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical class C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 claims description 2
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 2
• 229930192474 thiophene Natural products 0.000 claims description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
• 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 1
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
• XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical compound OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 claims 1
• XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 1
• XYTYTWRQDLUKCF-UHFFFAOYSA-N 2-[[5-[4-(4-carbamimidoylphenyl)phenyl]-1h-1,2,4-triazol-3-yl]sulfanyl]acetic acid Chemical compound C1=CC(C(=N)N)=CC=C1C1=CC=C(C=2N=C(SCC(O)=O)NN=2)C=C1 XYTYTWRQDLUKCF-UHFFFAOYSA-N 0.000 claims 1
• MYFWUKZYURBPHI-UHFFFAOYSA-N 2-amino-3-(1h-imidazol-2-yl)propanoic acid Chemical compound OC(=O)C(N)CC1=NC=CN1 MYFWUKZYURBPHI-UHFFFAOYSA-N 0.000 claims 1
• GBMWIUZJSVRMCJ-UHFFFAOYSA-N 3-(2-phenyl-1h-imidazol-5-yl)propanoic acid Chemical compound OC(=O)CCC1=CNC(C=2C=CC=CC=2)=N1 GBMWIUZJSVRMCJ-UHFFFAOYSA-N 0.000 claims 1
• RFSXIEAYLUHQNY-UHFFFAOYSA-N 3-[4-[4-(4-carbamimidoylphenyl)-1,3-thiazol-2-yl]phenyl]propanoic acid Chemical compound C1=CC(C(=N)N)=CC=C1C1=CSC(C=2C=CC(CCC(O)=O)=CC=2)=N1 RFSXIEAYLUHQNY-UHFFFAOYSA-N 0.000 claims 1
• NGWOGPJKZVPROF-UHFFFAOYSA-N 3-[4-[4-(4-carbamimidoylphenyl)-1-methylimidazol-2-yl]phenyl]propanoic acid Chemical compound CN1C=C(C=2C=CC(=CC=2)C(N)=N)N=C1C1=CC=C(CCC(O)=O)C=C1 NGWOGPJKZVPROF-UHFFFAOYSA-N 0.000 claims 1
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• 239000003153 chemical reaction reagent Substances 0.000 description 3
• 235000019253 formic acid Nutrition 0.000 description 3
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
• 238000005984 hydrogenation reaction Methods 0.000 description 3
• 239000005457 ice water Substances 0.000 description 3
• 229910052740 iodine Inorganic materials 0.000 description 3
• NUNUHAQUDHGXRJ-UHFFFAOYSA-N methyl 2-[4-[5-(4-carbamimidoylphenyl)-1h-imidazol-2-yl]-2-methylphenoxy]acetate Chemical compound C1=C(C)C(OCC(=O)OC)=CC=C1C1=NC=C(C=2C=CC(=CC=2)C(N)=N)N1 NUNUHAQUDHGXRJ-UHFFFAOYSA-N 0.000 description 3
• CWQBZDBQIVZBKN-UHFFFAOYSA-N methyl 2-[[4-[4-(4-carbamimidoylphenyl)phenyl]-1,3-thiazol-2-yl]amino]acetate Chemical compound S1C(NCC(=O)OC)=NC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C(N)=N)=C1 CWQBZDBQIVZBKN-UHFFFAOYSA-N 0.000 description 3
• ZMUIPHXGVPBFTD-UHFFFAOYSA-N methyl 2-[n-acetyl-4-[5-(4-carbamimidoylphenyl)-1h-imidazol-2-yl]-2-fluoroanilino]acetate Chemical compound C1=C(F)C(N(C(C)=O)CC(=O)OC)=CC=C1C1=NC(C=2C=CC(=CC=2)C(N)=N)=CN1 ZMUIPHXGVPBFTD-UHFFFAOYSA-N 0.000 description 3
• VLUGYNBUMWNJHC-UHFFFAOYSA-N methyl 2-[n-acetyl-4-[5-(4-carbamimidoylphenyl)-1h-imidazol-2-yl]anilino]acetate Chemical compound C1=CC(N(C(C)=O)CC(=O)OC)=CC=C1C1=NC(C=2C=CC(=CC=2)C(N)=N)=CN1 VLUGYNBUMWNJHC-UHFFFAOYSA-N 0.000 description 3
• ZMJWUNIOVFDWGR-UHFFFAOYSA-N methyl 2-amino-3-[1-[5-(4-carbamimidoylphenyl)pyrazin-2-yl]imidazol-4-yl]propanoate Chemical compound C1=NC(CC(N)C(=O)OC)=CN1C1=CN=C(C=2C=CC(=CC=2)C(N)=N)C=N1 ZMJWUNIOVFDWGR-UHFFFAOYSA-N 0.000 description 3
• YNUXGCGYBGNJOU-UHFFFAOYSA-N methyl 3-[1-[4-(4-carbamimidoylphenyl)-2-methylsulfonylphenyl]imidazol-4-yl]propanoate Chemical compound C1=NC(CCC(=O)OC)=CN1C1=CC=C(C=2C=CC(=CC=2)C(N)=N)C=C1S(C)(=O)=O YNUXGCGYBGNJOU-UHFFFAOYSA-N 0.000 description 3
• DGESEWLMNFSWOP-UHFFFAOYSA-N methyl 3-[1-[5-(4-carbamimidoylphenyl)-4-methylpyrimidin-2-yl]imidazol-4-yl]propanoate Chemical compound C1=NC(CCC(=O)OC)=CN1C1=NC=C(C=2C=CC(=CC=2)C(N)=N)C(C)=N1 DGESEWLMNFSWOP-UHFFFAOYSA-N 0.000 description 3
• RQMGNEPRHUBXQT-UHFFFAOYSA-N methyl 3-[1-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]-2-phenylimidazol-4-yl]propanoate Chemical compound N=1C(CCC(=O)OC)=CN(C=2N=NC(=CC=2)C=2C=CC(=CC=2)C(N)=N)C=1C1=CC=CC=C1 RQMGNEPRHUBXQT-UHFFFAOYSA-N 0.000 description 3
• HEXKJCRVNQAKFE-UHFFFAOYSA-N methyl 3-[1-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]-2-propan-2-ylimidazol-4-yl]propanoate Chemical compound CC(C)C1=NC(CCC(=O)OC)=CN1C1=CC=C(C=2C=CC(=CC=2)C(N)=N)N=N1 HEXKJCRVNQAKFE-UHFFFAOYSA-N 0.000 description 3
• BHGDICNLDQLIAJ-UHFFFAOYSA-N methyl 3-[1-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]imidazol-4-yl]-2-methoxypropanoate Chemical compound C1=NC(CC(OC)C(=O)OC)=CN1C1=CC=C(C=2C=CC(=CC=2)C(N)=N)N=N1 BHGDICNLDQLIAJ-UHFFFAOYSA-N 0.000 description 3
• ZOKPPMPQGBKEAZ-UHFFFAOYSA-N methyl 3-[1-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]triazol-4-yl]propanoate Chemical compound N1=NC(CCC(=O)OC)=CN1C1=CC=C(C=2C=CC(=CC=2)C(N)=N)N=N1 ZOKPPMPQGBKEAZ-UHFFFAOYSA-N 0.000 description 3
• JWENNAYCOQMQMG-UHFFFAOYSA-N methyl 3-[2-[1-(5-carbamimidoylpyridin-2-yl)piperidin-4-yl]-1,3-thiazol-4-yl]propanoate Chemical compound COC(=O)CCC1=CSC(C2CCN(CC2)C=2N=CC(=CC=2)C(N)=N)=N1 JWENNAYCOQMQMG-UHFFFAOYSA-N 0.000 description 3
• VFBXSNNRZAGJDU-UHFFFAOYSA-N methyl 3-[4-[1-(4-carbamimidoylphenyl)-2-methylimidazol-4-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=CN(C=2C=CC(=CC=2)C(N)=N)C(C)=N1 VFBXSNNRZAGJDU-UHFFFAOYSA-N 0.000 description 3
• XMDPGROZTHLZRF-UHFFFAOYSA-N methyl 3-[4-[3-(4-carbamimidoylphenyl)-1,2-oxazol-5-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=CC(C=2C=CC(=CC=2)C(N)=N)=NO1 XMDPGROZTHLZRF-UHFFFAOYSA-N 0.000 description 3
• CAVCLMDPFVMTFU-UHFFFAOYSA-N methyl 3-[4-[3-(4-carbamimidoylphenyl)-1h-pyrazol-5-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=CC(C=2C=CC(=CC=2)C(N)=N)=NN1 CAVCLMDPFVMTFU-UHFFFAOYSA-N 0.000 description 3
• AERFQHDCHLMWNO-UHFFFAOYSA-N methyl 3-[4-[4-(4-carbamimidoylphenyl)-1-methylimidazol-2-yl]phenyl]-2,2-dimethylpropanoate Chemical compound C1=CC(CC(C)(C)C(=O)OC)=CC=C1C1=NC(C=2C=CC(=CC=2)C(N)=N)=CN1C AERFQHDCHLMWNO-UHFFFAOYSA-N 0.000 description 3
• KYRQDBIFUMWWCQ-UHFFFAOYSA-N methyl 3-[4-[5-(4-carbamimidoylphenyl)-1h-imidazol-2-yl]-2-nitrophenyl]propanoate Chemical compound C1=C([N+]([O-])=O)C(CCC(=O)OC)=CC=C1C1=NC=C(C=2C=CC(=CC=2)C(N)=N)N1 KYRQDBIFUMWWCQ-UHFFFAOYSA-N 0.000 description 3
• YLPJYUDCPVBSOM-UHFFFAOYSA-N methyl 3-[4-[5-(4-carbamimidoylphenyl)-1h-imidazol-2-yl]cyclohexyl]propanoate Chemical compound C1CC(CCC(=O)OC)CCC1C1=NC(C=2C=CC(=CC=2)C(N)=N)=CN1 YLPJYUDCPVBSOM-UHFFFAOYSA-N 0.000 description 3
• FRPLAZNUFADXJC-UHFFFAOYSA-N methyl 3-[5-[4-(4-carbamimidoylphenyl)phenyl]furan-2-yl]propanoate Chemical compound O1C(CCC(=O)OC)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(N)=N)C=C1 FRPLAZNUFADXJC-UHFFFAOYSA-N 0.000 description 3
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• MMMXVKHYDDTHRV-UHFFFAOYSA-N methyl 2-[4-[5-(4-carbamimidoylphenyl)-1h-imidazol-2-yl]phenyl]sulfanylacetate Chemical compound C1=CC(SCC(=O)OC)=CC=C1C1=NC=C(C=2C=CC(=CC=2)C(N)=N)N1 MMMXVKHYDDTHRV-UHFFFAOYSA-N 0.000 description 2
• KNTRYSPLERGLPO-UHFFFAOYSA-N methyl 2-[4-[5-(4-carbamimidoylphenyl)-1h-imidazol-2-yl]phenyl]sulfonylacetate Chemical compound C1=CC(S(=O)(=O)CC(=O)OC)=CC=C1C1=NC=C(C=2C=CC(=CC=2)C(N)=N)N1 KNTRYSPLERGLPO-UHFFFAOYSA-N 0.000 description 2
• FICYUQITALPJTI-UHFFFAOYSA-N methyl 3-(4-carbamimidoylphenyl)-5-[4-(3-methoxy-3-oxopropyl)phenyl]-1h-pyrazole-4-carboxylate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=C(C(=O)OC)C(C=2C=CC(=CC=2)C(N)=N)=NN1 FICYUQITALPJTI-UHFFFAOYSA-N 0.000 description 2
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• MKSDBHPZYTZLRM-UHFFFAOYSA-N methyl 3-[1-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]-2-pyridin-3-ylimidazol-4-yl]propanoate Chemical compound N=1C(CCC(=O)OC)=CN(C=2N=NC(=CC=2)C=2C=CC(=CC=2)C(N)=N)C=1C1=CC=CN=C1 MKSDBHPZYTZLRM-UHFFFAOYSA-N 0.000 description 2
• NHEYGUFXBBKISU-UHFFFAOYSA-N methyl 3-[1-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]imidazol-4-yl]prop-2-enoate Chemical compound C1=NC(C=CC(=O)OC)=CN1C1=CC=C(C=2C=CC(=CC=2)C(N)=N)N=N1 NHEYGUFXBBKISU-UHFFFAOYSA-N 0.000 description 2
• FERQJQWVMZAZDM-UHFFFAOYSA-N methyl 3-[1-[6-(4-cyanophenyl)pyridazin-3-yl]imidazol-4-yl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate Chemical compound C1=NC(CC(C(=O)OC)NC(=O)OC(C)(C)C)=CN1C1=CC=C(C=2C=CC(=CC=2)C#N)N=N1 FERQJQWVMZAZDM-UHFFFAOYSA-N 0.000 description 2
• HEWHDSSMJLPOJI-UHFFFAOYSA-N methyl 3-[2-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]triazol-4-yl]propanoate Chemical compound N1=C(CCC(=O)OC)C=NN1C1=CC=C(C=2C=CC(=CC=2)C(N)=N)N=N1 HEWHDSSMJLPOJI-UHFFFAOYSA-N 0.000 description 2
• OYRCTCANAZVVPT-UHFFFAOYSA-N methyl 3-[2-amino-4-[5-(4-carbamimidoylphenyl)-1h-imidazol-2-yl]phenyl]propanoate Chemical compound C1=C(N)C(CCC(=O)OC)=CC=C1C1=NC=C(C=2C=CC(=CC=2)C(N)=N)N1 OYRCTCANAZVVPT-UHFFFAOYSA-N 0.000 description 2
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• LXHNQRGWWMORLQ-UHFFFAOYSA-N methyl 3-(4-aminophenyl)propanoate Chemical compound COC(=O)CCC1=CC=C(N)C=C1 LXHNQRGWWMORLQ-UHFFFAOYSA-N 0.000 description 1
• CIKIQYAEIGAWPF-UHFFFAOYSA-N methyl 3-(4-carbonochloridoylphenyl)propanoate Chemical compound COC(=O)CCC1=CC=C(C(Cl)=O)C=C1 CIKIQYAEIGAWPF-UHFFFAOYSA-N 0.000 description 1
• BWQYXMCLBNAQNM-UHFFFAOYSA-N methyl 3-[1-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]-2-methylimidazol-4-yl]propanoate Chemical compound CC1=NC(CCC(=O)OC)=CN1C1=CC=C(C=2C=CC(=CC=2)C(N)=N)N=N1 BWQYXMCLBNAQNM-UHFFFAOYSA-N 0.000 description 1
• HZVDGRHGPQHUDI-UHFFFAOYSA-N methyl 3-[1-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]imidazol-4-yl]-2-hydroxypropanoate Chemical compound C1=NC(CC(O)C(=O)OC)=CN1C1=CC=C(C=2C=CC(=CC=2)C(N)=N)N=N1 HZVDGRHGPQHUDI-UHFFFAOYSA-N 0.000 description 1
• RGSBMOXJZUGVTG-UHFFFAOYSA-N methyl 3-[1-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]indol-3-yl]propanoate Chemical compound C12=CC=CC=C2C(CCC(=O)OC)=CN1C(N=N1)=CC=C1C1=CC=C(C(N)=N)C=C1 RGSBMOXJZUGVTG-UHFFFAOYSA-N 0.000 description 1
• YDDHVOUMXQBYCI-UHFFFAOYSA-N methyl 3-[1-[6-(4-cyanophenyl)pyridazin-3-yl]imidazol-4-yl]-2-hydroxypropanoate Chemical compound C1=NC(CC(O)C(=O)OC)=CN1C1=CC=C(C=2C=CC(=CC=2)C#N)N=N1 YDDHVOUMXQBYCI-UHFFFAOYSA-N 0.000 description 1
• SOFANCSTPAYUCT-UHFFFAOYSA-N methyl 3-[1-[6-(4-cyanophenyl)pyridazin-3-yl]imidazol-4-yl]propanoate Chemical compound C1=NC(CCC(=O)OC)=CN1C1=CC=C(C=2C=CC(=CC=2)C#N)N=N1 SOFANCSTPAYUCT-UHFFFAOYSA-N 0.000 description 1
• QMVVEEGSRCWWLT-UHFFFAOYSA-N methyl 3-[4-(4-piperidin-4-ylphenyl)-1,3-thiazol-2-yl]propanoate Chemical compound S1C(CCC(=O)OC)=NC(C=2C=CC(=CC=2)C2CCNCC2)=C1 QMVVEEGSRCWWLT-UHFFFAOYSA-N 0.000 description 1
• NPLVTEVOMNWDAR-UHFFFAOYSA-N methyl 3-[4-[1-(4-carbamimidoylphenyl)-5-methylpyrazol-3-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=NN(C=2C=CC(=CC=2)C(N)=N)C(C)=C1 NPLVTEVOMNWDAR-UHFFFAOYSA-N 0.000 description 1
• BKCPBRVAPUZLER-UHFFFAOYSA-N methyl 3-[4-[2-(4-carbamimidoylphenyl)-1-methylimidazol-4-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=CN(C)C(C=2C=CC(=CC=2)C(N)=N)=N1 BKCPBRVAPUZLER-UHFFFAOYSA-N 0.000 description 1
• LAYOVWSLEFNBRE-UHFFFAOYSA-N methyl 3-[4-[3-(4-carbamimidoylphenyl)-1,2,4-triazol-1-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1N1N=C(C=2C=CC(=CC=2)C(N)=N)N=C1 LAYOVWSLEFNBRE-UHFFFAOYSA-N 0.000 description 1
• WWEPZOABFKHVSN-UHFFFAOYSA-N methyl 3-[4-[3-(4-carbamimidoylphenyl)-2-methyl-5-oxopyrazol-1-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1N1C(=O)C=C(C=2C=CC(=CC=2)C(N)=N)N1C WWEPZOABFKHVSN-UHFFFAOYSA-N 0.000 description 1
• VRLNFKLZGSLNOG-UHFFFAOYSA-N methyl 3-[4-[3-(4-carbamimidoylphenyl)pyrazol-1-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1N1N=C(C=2C=CC(=CC=2)C(N)=N)C=C1 VRLNFKLZGSLNOG-UHFFFAOYSA-N 0.000 description 1
• UVEYUWMSWYJADL-UHFFFAOYSA-N methyl 3-[4-[3-(4-cyanophenyl)-1h-1,2,4-triazol-5-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=NC(C=2C=CC(=CC=2)C#N)=NN1 UVEYUWMSWYJADL-UHFFFAOYSA-N 0.000 description 1
• SYQQYFHIJSNMDJ-UHFFFAOYSA-N methyl 3-[4-[4-(1-amino-2,3-dihydro-1h-inden-5-yl)-1-methylimidazol-2-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=NC(C=2C=C3CCC(N)C3=CC=2)=CN1C SYQQYFHIJSNMDJ-UHFFFAOYSA-N 0.000 description 1
• BEOINUSYOWCGCM-UHFFFAOYSA-N methyl 3-[4-[4-(1-carbamimidoylpiperidin-4-yl)phenyl]-1,3-thiazol-2-yl]propanoate Chemical compound S1C(CCC(=O)OC)=NC(C=2C=CC(=CC=2)C2CCN(CC2)C(N)=N)=C1 BEOINUSYOWCGCM-UHFFFAOYSA-N 0.000 description 1
• BIYDGKSIECNSGI-UHFFFAOYSA-N methyl 3-[4-[4-(4-carbamimidoylphenyl)-1,3-oxazol-2-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=NC(C=2C=CC(=CC=2)C(N)=N)=CO1 BIYDGKSIECNSGI-UHFFFAOYSA-N 0.000 description 1
• PTYPXXNAELWJRX-UHFFFAOYSA-N methyl 3-[4-[4-(4-carbamimidoylphenyl)-1-(2-phenylethyl)imidazol-2-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=NC(C=2C=CC(=CC=2)C(N)=N)=CN1CCC1=CC=CC=C1 PTYPXXNAELWJRX-UHFFFAOYSA-N 0.000 description 1
• LSIUJYJVIWOPOY-UHFFFAOYSA-N methyl 3-[4-[4-(4-carbamimidoylphenyl)-1-phenylimidazol-2-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=NC(C=2C=CC(=CC=2)C(N)=N)=CN1C1=CC=CC=C1 LSIUJYJVIWOPOY-UHFFFAOYSA-N 0.000 description 1
• JKBNGXHDWQOQDM-UHFFFAOYSA-N methyl 3-[4-[4-[4-(2-aminoethyl)phenyl]-1-methylimidazol-2-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=NC(C=2C=CC(CCN)=CC=2)=CN1C JKBNGXHDWQOQDM-UHFFFAOYSA-N 0.000 description 1
• ZQAUMVXXCPVOHJ-UHFFFAOYSA-N methyl 3-[4-[4-[4-(N-hydroxy-C-methylcarbonimidoyl)phenyl]-1-methylimidazol-2-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=NC(C=2C=CC(=CC=2)C(C)=NO)=CN1C ZQAUMVXXCPVOHJ-UHFFFAOYSA-N 0.000 description 1
• OACRHJVUHRJXLW-UHFFFAOYSA-N methyl 3-[4-[5-(3-aminophenyl)-1h-imidazol-2-yl]phenyl]propanoate;hydrochloride Chemical compound Cl.C1=CC(CCC(=O)OC)=CC=C1C1=NC=C(C=2C=C(N)C=CC=2)N1 OACRHJVUHRJXLW-UHFFFAOYSA-N 0.000 description 1
• CTAIBRDTLFWJHK-UHFFFAOYSA-N methyl 3-[4-[5-(4-cyanophenyl)-1,3,4-thiadiazol-2-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C#N)S1 CTAIBRDTLFWJHK-UHFFFAOYSA-N 0.000 description 1
• FGIXFUJXRLAKSP-UHFFFAOYSA-N methyl 3-[4-[5-(4-cyanophenyl)-1h-imidazol-2-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=NC(C=2C=CC(=CC=2)C#N)=CN1 FGIXFUJXRLAKSP-UHFFFAOYSA-N 0.000 description 1
• ASZVXKAPTCWCPT-UHFFFAOYSA-N methyl 3-[4-[[(4-cyanobenzoyl)amino]carbamoyl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C(=O)NNC(=O)C1=CC=C(C#N)C=C1 ASZVXKAPTCWCPT-UHFFFAOYSA-N 0.000 description 1
• IOZKWIIBOBSGRH-UHFFFAOYSA-N methyl 3-[5-[1-(4-carbamimidoylphenyl)piperidin-4-yl]tetrazol-2-yl]propanoate Chemical compound COC(=O)CCN1N=NC(C2CCN(CC2)C=2C=CC(=CC=2)C(N)=N)=N1 IOZKWIIBOBSGRH-UHFFFAOYSA-N 0.000 description 1
• HJXVAPKPZLSZSV-UHFFFAOYSA-N methyl 3-[[4-[1-methyl-4-(1-methylpiperidin-4-yl)imidazol-2-yl]benzoyl]amino]propanoate Chemical compound C1=CC(C(=O)NCCC(=O)OC)=CC=C1C1=NC(C2CCN(C)CC2)=CN1C HJXVAPKPZLSZSV-UHFFFAOYSA-N 0.000 description 1
• KQEVIFKPZOGBMZ-UHFFFAOYSA-N methyl 3-bromopropanoate Chemical compound COC(=O)CCBr KQEVIFKPZOGBMZ-UHFFFAOYSA-N 0.000 description 1
• KKZMIDYKRKGJHG-UHFFFAOYSA-N methyl 4-cyanobenzoate Chemical compound COC(=O)C1=CC=C(C#N)C=C1 KKZMIDYKRKGJHG-UHFFFAOYSA-N 0.000 description 1
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• 208000010125 myocardial infarction Diseases 0.000 description 1
• FWANZNVPCBFZLT-UHFFFAOYSA-N n-[(4-cyanophenyl)methylideneamino]benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NN=CC1=CC=C(C#N)C=C1 FWANZNVPCBFZLT-UHFFFAOYSA-N 0.000 description 1
• VZUGBLTVBZJZOE-KRWDZBQOSA-N n-[3-[(4s)-2-amino-1,4-dimethyl-6-oxo-5h-pyrimidin-4-yl]phenyl]-5-chloropyrimidine-2-carboxamide Chemical compound N1=C(N)N(C)C(=O)C[C@@]1(C)C1=CC=CC(NC(=O)C=2N=CC(Cl)=CN=2)=C1 VZUGBLTVBZJZOE-KRWDZBQOSA-N 0.000 description 1
• GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
• CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
• 125000002560 nitrile group Chemical group 0.000 description 1
• 230000009871 nonspecific binding Effects 0.000 description 1
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• 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
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• 239000011591 potassium Substances 0.000 description 1
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• 150000003141 primary amines Chemical class 0.000 description 1
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• ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
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• IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
• 150000004685 tetrahydrates Chemical group 0.000 description 1
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• RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 1
• 238000005809 transesterification reaction Methods 0.000 description 1
• YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
• XCAOVNOHVSHZTL-UHFFFAOYSA-N triethyl 2-(4-cyanophenyl)ethane-1,1,1-tricarboxylate Chemical compound CCOC(=O)C(C(=O)OCC)(C(=O)OCC)CC1=CC=C(C#N)C=C1 XCAOVNOHVSHZTL-UHFFFAOYSA-N 0.000 description 1
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• 239000005051 trimethylchlorosilane Substances 0.000 description 1
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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