SK2652001A3 - 2-oxo-i(2h)-quinoline derivatives - Google Patents

Info

Publication number

SK2652001A3

SK2652001A3 SK265-2001A SK2652001A SK2652001A3 SK 2652001 A3 SK2652001 A3 SK 2652001A3 SK 2652001 A SK2652001 A SK 2652001A SK 2652001 A3 SK2652001 A3 SK 2652001A3

Authority

SK

Slovakia

Prior art keywords

methyl

oxo

quinoline

group

oxadiazol

Prior art date

1998-08-29

Links

• Espacenet
• Global Dossier
• Discuss

• 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 91
• 108010074860 Factor Xa Proteins 0.000 claims abstract description 14
• 208000001435 Thromboembolism Diseases 0.000 claims abstract description 7
• -1 COOA Chemical group 0.000 claims description 170
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 40
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
• 150000003839 salts Chemical class 0.000 claims description 24
• 239000001257 hydrogen Substances 0.000 claims description 14
• 229910052739 hydrogen Inorganic materials 0.000 claims description 14
• 238000000034 method Methods 0.000 claims description 14
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
• 239000002253 acid Substances 0.000 claims description 12
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 12
• 125000001624 naphthyl group Chemical group 0.000 claims description 12
• 208000007536 Thrombosis Diseases 0.000 claims description 11
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 11
• 125000006239 protecting group Chemical group 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 9
• 238000007327 hydrogenolysis reaction Methods 0.000 claims description 9
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
• 125000003277 amino group Chemical group 0.000 claims description 8
• 239000003795 chemical substances by application Substances 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 7
• 238000002360 preparation method Methods 0.000 claims description 7
• 206010002383 Angina Pectoris Diseases 0.000 claims description 6
• 206010008190 Cerebrovascular accident Diseases 0.000 claims description 6
• 206010061218 Inflammation Diseases 0.000 claims description 6
• 208000006011 Stroke Diseases 0.000 claims description 6
• 238000002399 angioplasty Methods 0.000 claims description 6
• 230000004054 inflammatory process Effects 0.000 claims description 6
• 208000010125 myocardial infarction Diseases 0.000 claims description 6
• 239000008194 pharmaceutical composition Substances 0.000 claims description 6
• 230000008569 process Effects 0.000 claims description 6
• 208000037803 restenosis Diseases 0.000 claims description 6
• 238000003797 solvolysis reaction Methods 0.000 claims description 6
• 125000001424 substituent group Chemical group 0.000 claims description 6
• 206010003210 Arteriosclerosis Diseases 0.000 claims description 5
• 208000011775 arteriosclerosis disease Diseases 0.000 claims description 5
• 235000010290 biphenyl Nutrition 0.000 claims description 5
• 239000004305 biphenyl Substances 0.000 claims description 5
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 5
• 150000004866 oxadiazoles Chemical class 0.000 claims description 5
• 230000002265 prevention Effects 0.000 claims description 5
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
• 206010000087 Abdominal pain upper Diseases 0.000 claims description 4
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
• 229910052794 bromium Inorganic materials 0.000 claims description 4
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
• 239000000460 chlorine Substances 0.000 claims description 4
• 229910052801 chlorine Inorganic materials 0.000 claims description 4
• 229910052731 fluorine Inorganic materials 0.000 claims description 4
• 239000011737 fluorine Substances 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
• 229940123583 Factor Xa inhibitor Drugs 0.000 claims description 3
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
• 229910052740 iodine Inorganic materials 0.000 claims description 3
• 239000007788 liquid Substances 0.000 claims description 3
• 239000007787 solid Substances 0.000 claims description 3
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
• GLCWMNBUQIWUNH-UHFFFAOYSA-N 3-[[6-(3-carbamimidoylphenoxy)-4-methyl-2-oxoquinolin-1-yl]methyl]benzenecarboximidamide Chemical compound C12=CC=C(OC=3C=C(C=CC=3)C(N)=N)C=C2C(C)=CC(=O)N1CC1=CC=CC(C(N)=N)=C1 GLCWMNBUQIWUNH-UHFFFAOYSA-N 0.000 claims description 2
• NGWIOCRFKUBPBG-UHFFFAOYSA-N 7-[[6-(3-carbamimidoylphenoxy)-4-methyl-2-oxoquinolin-1-yl]methyl]naphthalene-2-carboximidamide Chemical compound C1=C2C(C)=CC(=O)N(CC=3C=C4C=C(C=CC4=CC=3)C(N)=N)C2=CC=C1OC1=CC=CC(C(N)=N)=C1 NGWIOCRFKUBPBG-UHFFFAOYSA-N 0.000 claims description 2
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
• 239000002552 dosage form Substances 0.000 claims description 2
• 125000004185 ester group Chemical group 0.000 claims description 2
• 150000002917 oxazolidines Chemical class 0.000 claims description 2
• 229910052760 oxygen Inorganic materials 0.000 claims description 2
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
• 239000012453 solvate Substances 0.000 claims description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
• 229940079593 drug Drugs 0.000 claims 1
• 239000003112 inhibitor Substances 0.000 abstract description 2
• 238000011321 prophylaxis Methods 0.000 abstract 1
• 238000002560 therapeutic procedure Methods 0.000 abstract 1
• 238000006243 chemical reaction Methods 0.000 description 47
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
• 239000000203 mixture Substances 0.000 description 27
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 17
• 239000000243 solution Substances 0.000 description 17
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
• 238000005984 hydrogenation reaction Methods 0.000 description 15
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 15
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 15
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
• 230000009467 reduction Effects 0.000 description 11
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
• 239000007868 Raney catalyst Substances 0.000 description 10
• 229910000564 Raney nickel Inorganic materials 0.000 description 10
• NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 10
• 230000015572 biosynthetic process Effects 0.000 description 10
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
• 108090000190 Thrombin Proteins 0.000 description 9
• 239000002168 alkylating agent Substances 0.000 description 9
• 229940100198 alkylating agent Drugs 0.000 description 9
• 230000005764 inhibitory process Effects 0.000 description 9
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 9
• QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
• 229960004072 thrombin Drugs 0.000 description 9
• 150000001409 amidines Chemical class 0.000 description 8
• 238000010265 fast atom bombardment Methods 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
• 239000002904 solvent Substances 0.000 description 8
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
• 239000004480 active ingredient Substances 0.000 description 7
• 125000002252 acyl group Chemical group 0.000 description 7
• 125000004432 carbon atom Chemical group C* 0.000 description 7
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
• WTDHULULXKLSOZ-UHFFFAOYSA-N hydroxylamine hydrochloride Substances Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 7
• WCYJQVALWQMJGE-UHFFFAOYSA-M hydroxylammonium chloride Chemical compound [Cl-].O[NH3+] WCYJQVALWQMJGE-UHFFFAOYSA-M 0.000 description 7
• CERZNQPNTHWEAD-UHFFFAOYSA-N 3-[3-(bromomethyl)phenyl]-5-methyl-1,2,4-oxadiazole Chemical compound O1C(C)=NC(C=2C=C(CBr)C=CC=2)=N1 CERZNQPNTHWEAD-UHFFFAOYSA-N 0.000 description 6
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
• 150000002148 esters Chemical class 0.000 description 6
• 230000007062 hydrolysis Effects 0.000 description 6
• 238000006460 hydrolysis reaction Methods 0.000 description 6
• 239000012442 inert solvent Substances 0.000 description 6
• 230000002401 inhibitory effect Effects 0.000 description 6
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
• VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
• 238000010992 reflux Methods 0.000 description 6
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
• STXAVEHFKAXGOX-UHFFFAOYSA-N 3-bromobenzonitrile Chemical compound BrC1=CC=CC(C#N)=C1 STXAVEHFKAXGOX-UHFFFAOYSA-N 0.000 description 5
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
• 150000007513 acids Chemical class 0.000 description 5
• 125000002947 alkylene group Chemical group 0.000 description 5
• 239000002585 base Substances 0.000 description 5
• 239000003054 catalyst Substances 0.000 description 5
• 229940012414 factor viia Drugs 0.000 description 5
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
• LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 5
• 239000007858 starting material Substances 0.000 description 5
• 239000000725 suspension Substances 0.000 description 5
• 239000003826 tablet Substances 0.000 description 5
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
• 108010014173 Factor X Proteins 0.000 description 4
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
• 150000001298 alcohols Chemical class 0.000 description 4
• 125000000217 alkyl group Chemical group 0.000 description 4
• 230000002785 anti-thrombosis Effects 0.000 description 4
• 239000003146 anticoagulant agent Substances 0.000 description 4
• 230000023555 blood coagulation Effects 0.000 description 4
• 238000003776 cleavage reaction Methods 0.000 description 4
• 238000001816 cooling Methods 0.000 description 4
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
• 238000005259 measurement Methods 0.000 description 4
• 150000002825 nitriles Chemical class 0.000 description 4
• 229910000027 potassium carbonate Inorganic materials 0.000 description 4
• 239000000047 product Substances 0.000 description 4
• 239000011541 reaction mixture Substances 0.000 description 4
• 230000007017 scission Effects 0.000 description 4
• 238000010626 work up procedure Methods 0.000 description 4
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
• 108010048049 Factor IXa Proteins 0.000 description 3
• 108010054265 Factor VIIa Proteins 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
• 230000004913 activation Effects 0.000 description 3
• 150000001408 amides Chemical class 0.000 description 3
• 229910021529 ammonia Inorganic materials 0.000 description 3
• 125000003118 aryl group Chemical group 0.000 description 3
• 125000006267 biphenyl group Chemical group 0.000 description 3
• 239000003114 blood coagulation factor Substances 0.000 description 3
• 239000002775 capsule Substances 0.000 description 3
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
• 150000001735 carboxylic acids Chemical class 0.000 description 3
• 125000000753 cycloalkyl group Chemical group 0.000 description 3
• 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
• 239000012154 double-distilled water Substances 0.000 description 3
• 238000010931 ester hydrolysis Methods 0.000 description 3
• 150000002170 ethers Chemical class 0.000 description 3
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
• 238000000338 in vitro Methods 0.000 description 3
• 238000001727 in vivo Methods 0.000 description 3
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
• 230000014508 negative regulation of coagulation Effects 0.000 description 3
• 125000004430 oxygen atom Chemical group O* 0.000 description 3
• AQLYZDRHNHZHIS-UHFFFAOYSA-N quinoline-2,6-diol Chemical compound N1C(=O)C=CC2=CC(O)=CC=C21 AQLYZDRHNHZHIS-UHFFFAOYSA-N 0.000 description 3
• 239000000741 silica gel Substances 0.000 description 3
• 229910002027 silica gel Inorganic materials 0.000 description 3
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
• 235000017557 sodium bicarbonate Nutrition 0.000 description 3
• 239000000126 substance Substances 0.000 description 3
• 239000000829 suppository Substances 0.000 description 3
• 239000000454 talc Substances 0.000 description 3
• 235000012222 talc Nutrition 0.000 description 3
• 229910052623 talc Inorganic materials 0.000 description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
• 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 2
• FWIROFMBWVMWLB-UHFFFAOYSA-N 1-bromo-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Br)=C1 FWIROFMBWVMWLB-UHFFFAOYSA-N 0.000 description 2
• XFRBXZCBOYNMJP-UHFFFAOYSA-N 2,2,6-trimethyl-1,3-dioxin-4-one Chemical compound CC1=CC(=O)OC(C)(C)O1 XFRBXZCBOYNMJP-UHFFFAOYSA-N 0.000 description 2
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
• XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
• ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
• PRNMVFNRQVCJSP-UHFFFAOYSA-N 3-(3-nitrophenoxy)benzonitrile Chemical compound [O-][N+](=O)C1=CC=CC(OC=2C=C(C=CC=2)C#N)=C1 PRNMVFNRQVCJSP-UHFFFAOYSA-N 0.000 description 2
• ICUJVTKZUNIFAB-UHFFFAOYSA-N 3-(4-nitrophenoxy)benzonitrile Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=CC(C#N)=C1 ICUJVTKZUNIFAB-UHFFFAOYSA-N 0.000 description 2
• BMXSEDLZMUPKSH-UHFFFAOYSA-N 3-[4-(bromomethyl)phenyl]-5-methyl-1,2,4-oxadiazole Chemical compound O1C(C)=NC(C=2C=CC(CBr)=CC=2)=N1 BMXSEDLZMUPKSH-UHFFFAOYSA-N 0.000 description 2
• FNGJXGVNJSUYIM-UHFFFAOYSA-N 3-[6-[[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]methoxy]-2-oxoquinolin-1-yl]benzonitrile Chemical compound O1C(C)=NC(C=2C=C(COC=3C=C4C=CC(=O)N(C=5C=C(C=CC=5)C#N)C4=CC=3)C=CC=2)=N1 FNGJXGVNJSUYIM-UHFFFAOYSA-N 0.000 description 2
• ZGQGRPYHCXFMBH-UHFFFAOYSA-N 3-[[1-(3-carbamimidoylphenyl)-2-oxoquinolin-6-yl]oxymethyl]benzenecarboximidamide Chemical compound NC(=N)C1=CC=CC(COC=2C=C3C=CC(=O)N(C=4C=C(C=CC=4)C(N)=N)C3=CC=2)=C1 ZGQGRPYHCXFMBH-UHFFFAOYSA-N 0.000 description 2
• RMVVDYJWOJJHBI-UHFFFAOYSA-N 3-[[6-[(3-carbamimidoylphenyl)methoxy]-2-oxoquinolin-1-yl]methyl]benzenecarboximidamide Chemical compound NC(=N)C1=CC=CC(COC=2C=C3C=CC(=O)N(CC=4C=C(C=CC=4)C(N)=N)C3=CC=2)=C1 RMVVDYJWOJJHBI-UHFFFAOYSA-N 0.000 description 2
• LLKLUTPIPLGLSW-UHFFFAOYSA-N 3-[[7-[(3-carbamimidoylphenyl)methoxy]-2-oxoquinolin-1-yl]methyl]benzenecarboximidamide Chemical compound NC(=N)C1=CC=CC(COC=2C=C3N(CC=4C=C(C=CC=4)C(N)=N)C(=O)C=CC3=CC=2)=C1 LLKLUTPIPLGLSW-UHFFFAOYSA-N 0.000 description 2
• JLTDKTOZEMXZFO-UHFFFAOYSA-N 3-ethyl-4-methyl-1h-quinolin-2-one Chemical compound C1=CC=C2NC(=O)C(CC)=C(C)C2=C1 JLTDKTOZEMXZFO-UHFFFAOYSA-N 0.000 description 2
• SGHBRHKBCLLVCI-UHFFFAOYSA-N 3-hydroxybenzonitrile Chemical compound OC1=CC=CC(C#N)=C1 SGHBRHKBCLLVCI-UHFFFAOYSA-N 0.000 description 2
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
• BQEXDUKMTVYBRK-UHFFFAOYSA-N 4-methyl-3-nitrophenol Chemical compound CC1=CC=C(O)C=C1[N+]([O-])=O BQEXDUKMTVYBRK-UHFFFAOYSA-N 0.000 description 2
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