SK74592A3 - Cyclic urea derivatives, their preparation and pharmaceutical agents with their content - Google Patents
Cyclic urea derivatives, their preparation and pharmaceutical agents with their content Download PDFInfo
- Publication number
- SK74592A3 SK74592A3 SK745-92A SK74592A SK74592A3 SK 74592 A3 SK74592 A3 SK 74592A3 SK 74592 A SK74592 A SK 74592A SK 74592 A3 SK74592 A3 SK 74592A3
- Authority
- SK
- Slovakia
- Prior art keywords
- group
- phenyl
- optionally substituted
- groups
- alkyl
- Prior art date
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- ZMGMDXCADSRNCX-UHFFFAOYSA-N 5,6-dihydroxy-1,3-diazepan-2-one Chemical class OC1CNC(=O)NCC1O ZMGMDXCADSRNCX-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 238000002360 preparation method Methods 0.000 title claims description 30
- 239000008177 pharmaceutical agent Substances 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 44
- 230000008569 process Effects 0.000 claims abstract description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- -1 alkyl radical Chemical class 0.000 claims description 645
- 150000001875 compounds Chemical class 0.000 claims description 147
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 138
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 136
- 239000000203 mixture Substances 0.000 claims description 126
- 229910052757 nitrogen Inorganic materials 0.000 claims description 122
- 125000004432 carbon atom Chemical group C* 0.000 claims description 110
- 150000003254 radicals Chemical class 0.000 claims description 93
- 125000000217 alkyl group Chemical group 0.000 claims description 70
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 69
- 239000000126 substance Substances 0.000 claims description 65
- 125000003118 aryl group Chemical group 0.000 claims description 58
- 239000000460 chlorine Substances 0.000 claims description 58
- 125000002947 alkylene group Chemical group 0.000 claims description 57
- 125000003545 alkoxy group Chemical group 0.000 claims description 53
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 53
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims description 48
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 48
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 48
- 229910052801 chlorine Inorganic materials 0.000 claims description 48
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 46
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 44
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 42
- 229910052731 fluorine Inorganic materials 0.000 claims description 41
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 40
- 239000011737 fluorine Substances 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 37
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 36
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 34
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 34
- 125000001072 heteroaryl group Chemical group 0.000 claims description 33
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 30
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 29
- 125000003277 amino group Chemical group 0.000 claims description 28
- 239000004202 carbamide Substances 0.000 claims description 28
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 27
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 27
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 26
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
- 125000005551 pyridylene group Chemical group 0.000 claims description 26
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 24
- 229910052717 sulfur Inorganic materials 0.000 claims description 24
- 125000004450 alkenylene group Chemical group 0.000 claims description 23
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 23
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 23
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
- 125000005550 pyrazinylene group Chemical group 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 23
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 23
- 125000005140 aralkylsulfonyl group Chemical group 0.000 claims description 22
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 21
- 125000005576 pyrimidinylene group Chemical group 0.000 claims description 21
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 20
- 229910052794 bromium Inorganic materials 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 239000001301 oxygen Substances 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 17
- 125000004647 alkyl sulfenyl group Chemical group 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 15
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 15
- 125000004434 sulfur atom Chemical group 0.000 claims description 14
- 125000001246 bromo group Chemical group Br* 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 11
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 9
- 150000001721 carbon Chemical group 0.000 claims description 9
- 125000005835 indanylene group Chemical group 0.000 claims description 9
- 239000011593 sulfur Substances 0.000 claims description 9
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 8
- 150000005840 aryl radicals Chemical class 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 8
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 8
- 125000005558 triazinylene group Chemical group 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 7
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 7
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 6
- 239000005977 Ethylene Substances 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000000320 amidine group Chemical group 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 150000003951 lactams Chemical group 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 6
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 5
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 5
- 125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 claims description 5
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 5
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 5
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 235000005985 organic acids Nutrition 0.000 claims description 5
- 230000000144 pharmacologic effect Effects 0.000 claims description 5
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims description 5
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 5
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000006356 alkylene carbonyl group Chemical group 0.000 claims description 4
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 4
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 4
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 4
- 238000010306 acid treatment Methods 0.000 claims description 3
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- 125000004980 cyclopropylene group Chemical group 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 3
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 claims description 2
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 claims description 2
- YHIIJNLSGULWAA-UHFFFAOYSA-N 1,4-thiazinane 1-oxide Chemical group O=S1CCNCC1 YHIIJNLSGULWAA-UHFFFAOYSA-N 0.000 claims description 2
- ZUQJRIFSHOJWJR-UHFFFAOYSA-N 3-[4-[3-(4-carbamimidoylphenyl)-2-oxoimidazolidin-1-yl]cyclohexyl]propanoic acid Chemical compound C1=CC(C(=N)N)=CC=C1N1C(=O)N(C2CCC(CCC(O)=O)CC2)CC1 ZUQJRIFSHOJWJR-UHFFFAOYSA-N 0.000 claims description 2
- FCMUCMIRXTVDTH-UHFFFAOYSA-N 3-[4-[3-(4-carbamimidoylphenyl)-2-oxoimidazolidin-1-yl]phenyl]propanoic acid Chemical compound C1=CC(C(=N)N)=CC=C1N1C(=O)N(C=2C=CC(CCC(O)=O)=CC=2)CC1 FCMUCMIRXTVDTH-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000005275 alkylenearyl group Chemical group 0.000 claims description 2
- 230000002744 anti-aggregatory effect Effects 0.000 claims description 2
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
- 125000005111 carboxyalkoxy group Chemical group 0.000 claims description 2
- JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 2
- 125000006357 methylene carbonyl group Chemical group [H]C([H])([*:1])C([*:2])=O 0.000 claims description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 2
- 125000002071 phenylalkoxy group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- PVYPYTKOKJWDHC-UHFFFAOYSA-N methyl 3-[4-[1-(4-carbamimidoylphenyl)-5-oxo-1,2,4-triazol-4-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1N1C(=O)N(C=2C=CC(=CC=2)C(N)=N)N=C1 PVYPYTKOKJWDHC-UHFFFAOYSA-N 0.000 claims 3
- NFBQBHMGHCCKQA-UHFFFAOYSA-N methyl 3-[4-[3-(4-carbamimidoylphenyl)-5-methyl-2-oxoimidazol-1-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1N1C(=O)N(C=2C=CC(=CC=2)C(N)=N)C=C1C NFBQBHMGHCCKQA-UHFFFAOYSA-N 0.000 claims 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 2
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- CCVRPNVTUVTQBT-UHFFFAOYSA-N 2-methylpropyl 3-[4-[1-[4-[(e)-n'-methoxycarbonylcarbamimidoyl]phenyl]-3-methyl-5-oxo-1,2,4-triazol-4-yl]phenyl]propanoate Chemical compound C1=CC(C(=N)NC(=O)OC)=CC=C1N1C(=O)N(C=2C=CC(CCC(=O)OCC(C)C)=CC=2)C(C)=N1 CCVRPNVTUVTQBT-UHFFFAOYSA-N 0.000 claims 1
- QOQPQNXCBCAMCT-UHFFFAOYSA-N 3-[4-[1-(4-carbamimidoylphenyl)-3-ethyl-5-oxo-1,2,4-triazol-4-yl]phenyl]propanoic acid Chemical compound O=C1N(C=2C=CC(CCC(O)=O)=CC=2)C(CC)=NN1C1=CC=C(C(N)=N)C=C1 QOQPQNXCBCAMCT-UHFFFAOYSA-N 0.000 claims 1
- SRJBCDRFXOZHMY-UHFFFAOYSA-N 3-[4-[1-(4-carbamimidoylphenyl)-3-methyl-5-oxo-1,2,4-triazol-4-yl]phenyl]propanoic acid Chemical compound O=C1N(C=2C=CC(CCC(O)=O)=CC=2)C(C)=NN1C1=CC=C(C(N)=N)C=C1 SRJBCDRFXOZHMY-UHFFFAOYSA-N 0.000 claims 1
- CSJCCFVGAIQRTF-UHFFFAOYSA-N 3-[4-[1-(4-carbamimidoylphenyl)-5-oxo-1,2,4-triazol-4-yl]phenyl]propanoic acid Chemical compound C1=CC(C(=N)N)=CC=C1N1C(=O)N(C=2C=CC(CCC(O)=O)=CC=2)C=N1 CSJCCFVGAIQRTF-UHFFFAOYSA-N 0.000 claims 1
- BQUXTYDUWQRCNT-UHFFFAOYSA-N 3-[4-[3-(4-carbamimidoylphenyl)-2,5-dioxoimidazolidin-1-yl]phenyl]propanoic acid Chemical compound C1=CC(C(=N)N)=CC=C1N1C(=O)N(C=2C=CC(CCC(O)=O)=CC=2)C(=O)C1 BQUXTYDUWQRCNT-UHFFFAOYSA-N 0.000 claims 1
- RRKQVQVEOHDDDC-UHFFFAOYSA-N 3-[4-[3-(4-carbamimidoylphenyl)-2-oxoimidazol-1-yl]phenyl]propanoic acid Chemical compound C1=CC(C(=N)N)=CC=C1N1C(=O)N(C=2C=CC(CCC(O)=O)=CC=2)C=C1 RRKQVQVEOHDDDC-UHFFFAOYSA-N 0.000 claims 1
- RNCKAEIHXJHBRQ-UHFFFAOYSA-N 3-[4-[5-(4-carbamimidoylphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-2-yl]phenyl]propanoic acid Chemical compound C1=CC(C(=N)N)=CC=C1N1S(=O)(=O)N(C=2C=CC(CCC(O)=O)=CC=2)CC1 RNCKAEIHXJHBRQ-UHFFFAOYSA-N 0.000 claims 1
- 239000004677 Nylon Substances 0.000 claims 1
- 150000008051 alkyl sulfates Chemical class 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims 1
- 125000005998 bromoethyl group Chemical group 0.000 claims 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- WINNISSSXBRWMA-UHFFFAOYSA-N dinitromethane Chemical group [O-][N+](=O)C[N+]([O-])=O WINNISSSXBRWMA-UHFFFAOYSA-N 0.000 claims 1
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 1
- NERXUWHQJQDKDD-UHFFFAOYSA-N methyl 3-[4-[1-(4-carbamimidoylphenyl)-3-ethyl-5-oxo-1,2,4-triazol-4-yl]phenyl]propanoate Chemical compound O=C1N(C=2C=CC(CCC(=O)OC)=CC=2)C(CC)=NN1C1=CC=C(C(N)=N)C=C1 NERXUWHQJQDKDD-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 229920001778 nylon Polymers 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 150000003216 pyrazines Chemical class 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 238000001149 thermolysis Methods 0.000 claims 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 522
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 312
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 273
- 238000002844 melting Methods 0.000 description 138
- 230000008018 melting Effects 0.000 description 138
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 133
- 239000000741 silica gel Substances 0.000 description 133
- 229910002027 silica gel Inorganic materials 0.000 description 133
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 109
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 108
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 99
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 86
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 83
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 75
- 239000012071 phase Substances 0.000 description 73
- 239000002904 solvent Substances 0.000 description 72
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 66
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 62
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 58
- 239000000243 solution Substances 0.000 description 55
- 230000002441 reversible effect Effects 0.000 description 52
- 238000006243 chemical reaction Methods 0.000 description 51
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 49
- 239000011780 sodium chloride Substances 0.000 description 49
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 48
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 41
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 39
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
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- 230000002427 irreversible effect Effects 0.000 description 1
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- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- PMRYVIKBURPHAH-UHFFFAOYSA-N methimazole Chemical compound CN1C=CNC1=S PMRYVIKBURPHAH-UHFFFAOYSA-N 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- CNJDPWLVWYWNQP-UHFFFAOYSA-N methyl 2-[2-[3-(4-carbamimidoylphenyl)-2-oxoimidazolidin-1-yl]ethylsulfonyl]acetate;hydrochloride Chemical compound Cl.O=C1N(CCS(=O)(=O)CC(=O)OC)CCN1C1=CC=C(C(N)=N)C=C1 CNJDPWLVWYWNQP-UHFFFAOYSA-N 0.000 description 1
- IGYPJYGCODLPEK-UHFFFAOYSA-N methyl 2-[2-[3-(4-carbamimidoylphenyl)-2-oxoimidazolidin-1-yl]phenyl]sulfonylacetate Chemical compound COC(=O)CS(=O)(=O)C1=CC=CC=C1N1C(=O)N(C=2C=CC(=CC=2)C(N)=N)CC1 IGYPJYGCODLPEK-UHFFFAOYSA-N 0.000 description 1
- XNIRZBLOHROVAT-UHFFFAOYSA-N methyl 2-[3-(4-carbamimidoylphenyl)-2-oxoimidazolidin-1-yl]ethylsulfanylformate;hydrochloride Chemical compound Cl.O=C1N(CCSC(=O)OC)CCN1C1=CC=C(C(N)=N)C=C1 XNIRZBLOHROVAT-UHFFFAOYSA-N 0.000 description 1
- BLIQFLLZYMUBGE-UHFFFAOYSA-N methyl 2-[4-[3-(4-carbamimidoylphenyl)-2-oxoimidazolidin-1-yl]-2-(2-methoxy-2-oxoethoxy)phenoxy]acetate Chemical compound C1=C(OCC(=O)OC)C(OCC(=O)OC)=CC=C1N1C(=O)N(C=2C=CC(=CC=2)C(N)=N)CC1 BLIQFLLZYMUBGE-UHFFFAOYSA-N 0.000 description 1
- DAEJFNAWZPAUSZ-UHFFFAOYSA-N methyl 2-[4-[3-(4-carbamimidoylphenyl)-2-oxoimidazolidin-1-yl]phenoxy]acetate;hydrochloride Chemical compound Cl.C1=CC(OCC(=O)OC)=CC=C1N1C(=O)N(C=2C=CC(=CC=2)C(N)=N)CC1 DAEJFNAWZPAUSZ-UHFFFAOYSA-N 0.000 description 1
- WOSLLPGEPVRPDH-UHFFFAOYSA-N methyl 2-[4-[3-(4-carbamimidoylphenyl)-2-oxoimidazolidin-1-yl]phenyl]sulfonylacetate;hydrochloride Chemical compound Cl.C1=CC(S(=O)(=O)CC(=O)OC)=CC=C1N1C(=O)N(C=2C=CC(=CC=2)C(N)=N)CC1 WOSLLPGEPVRPDH-UHFFFAOYSA-N 0.000 description 1
- VNIYZHUJGFTWIR-UHFFFAOYSA-N methyl 2-[4-[3-(4-cyanophenyl)-2-oxoimidazolidin-1-yl]phenyl]sulfonylacetate Chemical compound C1=CC(S(=O)(=O)CC(=O)OC)=CC=C1N1C(=O)N(C=2C=CC(=CC=2)C#N)CC1 VNIYZHUJGFTWIR-UHFFFAOYSA-N 0.000 description 1
- UTRLIWAPLSTPES-UHFFFAOYSA-N methyl 2-amino-3-[4-[3-(4-carbamimidoylphenyl)-2-oxoimidazol-1-yl]phenyl]propanoate;dihydrochloride Chemical compound Cl.Cl.C1=CC(CC(N)C(=O)OC)=CC=C1N1C(=O)N(C=2C=CC(=CC=2)C(N)=N)C=C1 UTRLIWAPLSTPES-UHFFFAOYSA-N 0.000 description 1
- ULZRKRFMYFKSSN-UHFFFAOYSA-N methyl 2-amino-3-[4-[3-(4-cyanophenyl)-2-oxoimidazol-1-yl]phenyl]propanoate;hydrochloride Chemical compound Cl.C1=CC(CC(N)C(=O)OC)=CC=C1N1C(=O)N(C=2C=CC(=CC=2)C#N)C=C1 ULZRKRFMYFKSSN-UHFFFAOYSA-N 0.000 description 1
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
- FOYOOILINPEMPI-UHFFFAOYSA-N methyl 3-(4-amino-3-methoxyphenyl)propanoate Chemical compound COC(=O)CCC1=CC=C(N)C(OC)=C1 FOYOOILINPEMPI-UHFFFAOYSA-N 0.000 description 1
- 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
- NFFOXPLOXZDPPD-UHFFFAOYSA-N methyl 3-(4-aminophenyl)propanoate;hydrochloride Chemical compound Cl.COC(=O)CCC1=CC=C(N)C=C1 NFFOXPLOXZDPPD-UHFFFAOYSA-N 0.000 description 1
- UJYCDXGGEJSYQG-UHFFFAOYSA-N methyl 3-[3-[1-(4-carbamimidoylphenyl)piperidin-4-yl]-2-oxoimidazol-1-yl]propanoate;hydrochloride Chemical compound Cl.O=C1N(CCC(=O)OC)C=CN1C1CCN(C=2C=CC(=CC=2)C(N)=N)CC1 UJYCDXGGEJSYQG-UHFFFAOYSA-N 0.000 description 1
- KPVLDQQTTZSIBX-UHFFFAOYSA-N methyl 3-[3-[1-(4-carbamimidoylphenyl)piperidin-4-yl]-2-oxoimidazolidin-1-yl]propanoate;hydrochloride Chemical compound Cl.O=C1N(CCC(=O)OC)CCN1C1CCN(C=2C=CC(=CC=2)C(N)=N)CC1 KPVLDQQTTZSIBX-UHFFFAOYSA-N 0.000 description 1
- IEONECUSOOYOKR-UHFFFAOYSA-N methyl 3-[3-[2-(4-cyanophenyl)pyrimidin-5-yl]-2-oxoimidazolidin-1-yl]propanoate Chemical compound O=C1N(CCC(=O)OC)CCN1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 IEONECUSOOYOKR-UHFFFAOYSA-N 0.000 description 1
- ODIZNVSQTXWDMZ-UHFFFAOYSA-N methyl 3-[3-[2-acetamido-4-(4-cyanophenyl)phenyl]-2-oxoimidazolidin-1-yl]propanoate Chemical compound O=C1N(CCC(=O)OC)CCN1C1=CC=C(C=2C=CC(=CC=2)C#N)C=C1NC(C)=O ODIZNVSQTXWDMZ-UHFFFAOYSA-N 0.000 description 1
- OJZWTBYOJCSJDT-UHFFFAOYSA-N methyl 3-[3-[2-amino-4-(4-cyanophenyl)phenyl]-2-oxoimidazolidin-1-yl]propanoate Chemical compound O=C1N(CCC(=O)OC)CCN1C1=CC=C(C=2C=CC(=CC=2)C#N)C=C1N OJZWTBYOJCSJDT-UHFFFAOYSA-N 0.000 description 1
- FGZJGERUKIFNLB-UHFFFAOYSA-N methyl 3-[3-[4-(4-carbamimidoylphenyl)cyclohexyl]-2-oxoimidazolidin-1-yl]propanoate Chemical compound O=C1N(CCC(=O)OC)CCN1C1CCC(C=2C=CC(=CC=2)C(N)=N)CC1 FGZJGERUKIFNLB-UHFFFAOYSA-N 0.000 description 1
- VZXUBGHJXSLTOQ-UHFFFAOYSA-N methyl 3-[3-[4-(4-carbamimidoylphenyl)cyclohexyl]-2-oxoimidazolidin-1-yl]propanoate;hydrochloride Chemical compound Cl.O=C1N(CCC(=O)OC)CCN1C1CCC(C=2C=CC(=CC=2)C(N)=N)CC1 VZXUBGHJXSLTOQ-UHFFFAOYSA-N 0.000 description 1
- WEUZQXHXLACKJP-UHFFFAOYSA-N methyl 3-[3-[4-(4-cyanophenyl)phenyl]-2-oxoimidazolidin-1-yl]propanoate Chemical compound O=C1N(CCC(=O)OC)CCN1C1=CC=C(C=2C=CC(=CC=2)C#N)C=C1 WEUZQXHXLACKJP-UHFFFAOYSA-N 0.000 description 1
- IVJHIYDBZMCILJ-UHFFFAOYSA-N methyl 3-[3-[4-(5-cyanopyrazin-2-yl)phenyl]-2-oxoimidazolidin-1-yl]propanoate Chemical compound O=C1N(CCC(=O)OC)CCN1C1=CC=C(C=2N=CC(=NC=2)C#N)C=C1 IVJHIYDBZMCILJ-UHFFFAOYSA-N 0.000 description 1
- LIBRJDRFLWPRAU-UHFFFAOYSA-N methyl 3-[3-[4-(5-cyanopyridin-2-yl)phenyl]-2-oxoimidazolidin-1-yl]propanoate Chemical compound O=C1N(CCC(=O)OC)CCN1C1=CC=C(C=2N=CC(=CC=2)C#N)C=C1 LIBRJDRFLWPRAU-UHFFFAOYSA-N 0.000 description 1
- XIXMSIGFHDRZRE-UHFFFAOYSA-N methyl 3-[3-[4-(5-cyanopyrimidin-2-yl)phenyl]-2-oxoimidazolidin-1-yl]propanoate Chemical compound O=C1N(CCC(=O)OC)CCN1C1=CC=C(C=2N=CC(=CN=2)C#N)C=C1 XIXMSIGFHDRZRE-UHFFFAOYSA-N 0.000 description 1
- QLBBAXIYKORRCY-UHFFFAOYSA-N methyl 3-[4-(2,2-diethoxyethylamino)phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate Chemical compound CCOC(OCC)CNC1=CC=C(CC(NC(=O)OC(C)(C)C)C(=O)OC)C=C1 QLBBAXIYKORRCY-UHFFFAOYSA-N 0.000 description 1
- VEYGATDBLJOZCF-UHFFFAOYSA-N methyl 3-[4-(2-hydroxyethylamino)phenyl]-3-methylbutanoate Chemical compound COC(=O)CC(C)(C)C1=CC=C(NCCO)C=C1 VEYGATDBLJOZCF-UHFFFAOYSA-N 0.000 description 1
- MFUGAFAMXDNYLY-UHFFFAOYSA-N methyl 3-[4-(2-hydroxypropylamino)phenyl]propanoate Chemical compound COC(=O)CCC1=CC=C(NCC(C)O)C=C1 MFUGAFAMXDNYLY-UHFFFAOYSA-N 0.000 description 1
- UZBPVMUYVNDCBO-UHFFFAOYSA-N methyl 3-[4-(2-oxo-1H-imidazol-3-yl)phenyl]propanoate Chemical compound COC(=O)CCC1=CC=C(C=C1)N1C(NC=C1)=O UZBPVMUYVNDCBO-UHFFFAOYSA-N 0.000 description 1
- UWTVTWIXUYDNLT-UHFFFAOYSA-N methyl 3-[4-(2-oxoimidazolidin-1-yl)cyclohexyl]propanoate Chemical compound C1CC(CCC(=O)OC)CCC1N1C(=O)NCC1 UWTVTWIXUYDNLT-UHFFFAOYSA-N 0.000 description 1
- AIKFEGLHBMSRRS-UHFFFAOYSA-N methyl 3-[4-[1-(4-carbamimidoylphenyl)-3-ethyl-5-oxo-1,2,4-triazol-4-yl]phenyl]propanoate;hydrochloride Chemical compound Cl.O=C1N(C=2C=CC(CCC(=O)OC)=CC=2)C(CC)=NN1C1=CC=C(C(N)=N)C=C1 AIKFEGLHBMSRRS-UHFFFAOYSA-N 0.000 description 1
- ZKNCETGPAUFSCO-UHFFFAOYSA-N methyl 3-[4-[1-(4-carbamimidoylphenyl)-3-methyl-2-oxoimidazol-4-yl]phenyl]propanoate;hydrochloride Chemical compound Cl.C1=CC(CCC(=O)OC)=CC=C1C(N(C1=O)C)=CN1C1=CC=C(C(N)=N)C=C1 ZKNCETGPAUFSCO-UHFFFAOYSA-N 0.000 description 1
- ZZFWUEICLGPEIY-UHFFFAOYSA-N methyl 3-[4-[1-(4-carbamimidoylphenyl)-3-methyl-2-oxoimidazolidin-4-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1N(C)C(=O)N(C=2C=CC(=CC=2)C(N)=N)C1 ZZFWUEICLGPEIY-UHFFFAOYSA-N 0.000 description 1
- XJUCHYURLOBKJW-UHFFFAOYSA-N methyl 3-[4-[1-(4-carbamimidoylphenyl)-5-oxo-3-(trifluoromethyl)-1,2,4-triazol-4-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1N1C(=O)N(C=2C=CC(=CC=2)C(N)=N)N=C1C(F)(F)F XJUCHYURLOBKJW-UHFFFAOYSA-N 0.000 description 1
- IIYXOHUCYGPDJP-UHFFFAOYSA-N methyl 3-[4-[1-(4-carbamimidoylphenyl)-5-oxo-3-phenyl-1,2,4-triazol-4-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1N1C(=O)N(C=2C=CC(=CC=2)C(N)=N)N=C1C1=CC=CC=C1 IIYXOHUCYGPDJP-UHFFFAOYSA-N 0.000 description 1
- BBHBJDHRIAGIEF-UHFFFAOYSA-N methyl 3-[4-[1-(4-cyanophenyl)-2-oxo-3-phenylimidazol-4-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C(N(C1=O)C=2C=CC=CC=2)=CN1C1=CC=C(C#N)C=C1 BBHBJDHRIAGIEF-UHFFFAOYSA-N 0.000 description 1
- JNYVPQWTJZBEQJ-UHFFFAOYSA-N methyl 3-[4-[1-(4-cyanophenyl)-3,5-dimethyl-2-oxoimidazol-4-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C(N(C1=O)C)=C(C)N1C1=CC=C(C#N)C=C1 JNYVPQWTJZBEQJ-UHFFFAOYSA-N 0.000 description 1
- QIJYIKYSGQORDP-UHFFFAOYSA-N methyl 3-[4-[1-(4-cyanophenyl)-3-methyl-2-oxoimidazol-4-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C(N(C1=O)C)=CN1C1=CC=C(C#N)C=C1 QIJYIKYSGQORDP-UHFFFAOYSA-N 0.000 description 1
- GDELHSFCSFMQNO-UHFFFAOYSA-N methyl 3-[4-[1-(4-cyanophenyl)-3-phenyl-2-sulfanylideneimidazol-4-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C(N(C1=S)C=2C=CC=CC=2)=CN1C1=CC=C(C#N)C=C1 GDELHSFCSFMQNO-UHFFFAOYSA-N 0.000 description 1
- GVGFPOVMXHXXTE-UHFFFAOYSA-N methyl 3-[4-[1-(4-cyanophenyl)-5-methyl-2-oxo-3-phenylimidazol-4-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C(N(C1=O)C=2C=CC=CC=2)=C(C)N1C1=CC=C(C#N)C=C1 GVGFPOVMXHXXTE-UHFFFAOYSA-N 0.000 description 1
- MURBZYAPDVDFSX-UHFFFAOYSA-N methyl 3-[4-[2-oxo-3-[4-[(e)-n'-phenylmethoxycarbonylcarbamimidoyl]phenyl]imidazolidin-1-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1N1C(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)OCC=2C=CC=CC=2)CC1 MURBZYAPDVDFSX-UHFFFAOYSA-N 0.000 description 1
- NCDXZSRKGRNWBW-UHFFFAOYSA-N methyl 3-[4-[2-oxo-3-[4-[(e)-n'-propan-2-yloxycarbonylcarbamimidoyl]phenyl]imidazolidin-1-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1N1C(=O)N(C=2C=CC(=CC=2)C(N)=NC(=O)OC(C)C)CC1 NCDXZSRKGRNWBW-UHFFFAOYSA-N 0.000 description 1
- DJRDLVHMCPGGID-UHFFFAOYSA-N methyl 3-[4-[3-(1-carbamimidoylpiperidin-4-yl)-2-oxoimidazolidin-1-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1N1C(=O)N(C2CCN(CC2)C(N)=N)CC1 DJRDLVHMCPGGID-UHFFFAOYSA-N 0.000 description 1
- RYRVYDAFILQQOA-UHFFFAOYSA-N methyl 3-[4-[3-(1-hydroxyimino-2,3-dihydroinden-5-yl)-2-oxoimidazolidin-1-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1N1C(=O)N(C=2C=C3CCC(C3=CC=2)=NO)CC1 RYRVYDAFILQQOA-UHFFFAOYSA-N 0.000 description 1
- CNVQAJHCECCBPN-UHFFFAOYSA-N methyl 3-[4-[3-(3-aminophenyl)-2-oxoimidazolidin-1-yl]phenyl]propanoate;hydrochloride Chemical compound Cl.C1=CC(CCC(=O)OC)=CC=C1N1C(=O)N(C=2C=C(N)C=CC=2)CC1 CNVQAJHCECCBPN-UHFFFAOYSA-N 0.000 description 1
- KOMMTHLOMGQEBV-UHFFFAOYSA-N methyl 3-[4-[3-(4-acetylphenyl)-2-oxoimidazolidin-1-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1N1C(=O)N(C=2C=CC(=CC=2)C(C)=O)CC1 KOMMTHLOMGQEBV-UHFFFAOYSA-N 0.000 description 1
- QKFJBLNKZTZBAH-UHFFFAOYSA-N methyl 3-[4-[3-(4-carbamimidoyl-2-methylsulfinylphenyl)-2-oxoimidazolidin-1-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1N1C(=O)N(C=2C(=CC(=CC=2)C(N)=N)S(C)=O)CC1 QKFJBLNKZTZBAH-UHFFFAOYSA-N 0.000 description 1
- BZOFWFSMICOVBQ-UHFFFAOYSA-N methyl 3-[4-[3-(4-carbamimidoyl-2-methylsulfonylphenyl)-2-oxoimidazolidin-1-yl]phenyl]propanoate;hydrochloride Chemical compound Cl.C1=CC(CCC(=O)OC)=CC=C1N1C(=O)N(C=2C(=CC(=CC=2)C(N)=N)S(C)(=O)=O)CC1 BZOFWFSMICOVBQ-UHFFFAOYSA-N 0.000 description 1
- QRIFVBJFOQQGQU-UHFFFAOYSA-N methyl 3-[4-[3-(4-carbamimidoylphenyl)-2-oxoimidazol-1-yl]phenyl]-2-(dibenzylamino)propanoate;hydrochloride Chemical compound Cl.C=1C=CC=CC=1CN(CC=1C=CC=CC=1)C(C(=O)OC)CC(C=C1)=CC=C1N(C1=O)C=CN1C1=CC=C(C(N)=N)C=C1 QRIFVBJFOQQGQU-UHFFFAOYSA-N 0.000 description 1
- UNGYTLCOVTUWOC-UHFFFAOYSA-N methyl 3-[4-[3-(4-carbamimidoylphenyl)-2-oxoimidazol-1-yl]phenyl]-2-(dimethylamino)propanoate Chemical compound C1=CC(CC(C(=O)OC)N(C)C)=CC=C1N1C(=O)N(C=2C=CC(=CC=2)C(N)=N)C=C1 UNGYTLCOVTUWOC-UHFFFAOYSA-N 0.000 description 1
- LTCDFPGGTRNWMZ-UHFFFAOYSA-N methyl 3-[4-[3-(4-carbamimidoylphenyl)-2-oxoimidazol-1-yl]phenyl]-2-hydroxypropanoate Chemical compound C1=CC(CC(O)C(=O)OC)=CC=C1N1C(=O)N(C=2C=CC(=CC=2)C(N)=N)C=C1 LTCDFPGGTRNWMZ-UHFFFAOYSA-N 0.000 description 1
- BRFJDDBHWLSYBC-UHFFFAOYSA-N methyl 3-[4-[3-(4-carbamimidoylphenyl)-2-oxoimidazolidin-1-yl]-3-methylphenyl]propanoate;hydrochloride Chemical compound Cl.CC1=CC(CCC(=O)OC)=CC=C1N1C(=O)N(C=2C=CC(=CC=2)C(N)=N)CC1 BRFJDDBHWLSYBC-UHFFFAOYSA-N 0.000 description 1
- BMEKBURGTHNGHC-UHFFFAOYSA-N methyl 3-[4-[3-(4-carbamimidoylphenyl)-2-oxoimidazolidin-1-yl]-3-methylsulfinylphenyl]propanoate Chemical compound CS(=O)C1=CC(CCC(=O)OC)=CC=C1N1C(=O)N(C=2C=CC(=CC=2)C(N)=N)CC1 BMEKBURGTHNGHC-UHFFFAOYSA-N 0.000 description 1
- YMORAFMLBCVHCH-UHFFFAOYSA-N methyl 3-[4-[3-(4-carbamimidoylphenyl)-4-methyl-5-oxo-1,2,4-triazol-1-yl]phenyl]propanoate;hydrochloride Chemical compound Cl.C1=CC(CCC(=O)OC)=CC=C1N1C(=O)N(C)C(C=2C=CC(=CC=2)C(N)=N)=N1 YMORAFMLBCVHCH-UHFFFAOYSA-N 0.000 description 1
- JMBKDBOJXOIYAQ-UHFFFAOYSA-N methyl 3-[4-[3-(4-cyanophenyl)-2-oxo-1,3-diazinan-1-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1N1C(=O)N(C=2C=CC(=CC=2)C#N)CCC1 JMBKDBOJXOIYAQ-UHFFFAOYSA-N 0.000 description 1
- HQGQVAPEOVNTFY-UHFFFAOYSA-N methyl 3-[4-[3-(4-cyanophenyl)-2-oxoimidazol-1-yl]phenyl]-2-(dibenzylamino)propanoate Chemical compound C=1C=CC=CC=1CN(CC=1C=CC=CC=1)C(C(=O)OC)CC(C=C1)=CC=C1N(C1=O)C=CN1C1=CC=C(C#N)C=C1 HQGQVAPEOVNTFY-UHFFFAOYSA-N 0.000 description 1
- ZRCURHOYKZUOOC-UHFFFAOYSA-N methyl 3-[4-[3-(4-cyanophenyl)-2-oxoimidazolidin-1-yl]-3-methylsulfonylphenyl]propanoate Chemical compound CS(=O)(=O)C1=CC(CCC(=O)OC)=CC=C1N1C(=O)N(C=2C=CC(=CC=2)C#N)CC1 ZRCURHOYKZUOOC-UHFFFAOYSA-N 0.000 description 1
- DCXICDWGXYOAPE-UHFFFAOYSA-N methyl 3-[4-[3-(4-cyanophenyl)-2-oxoimidazolidin-1-yl]phenyl]-3-methylbutanoate Chemical compound C1=CC(C(C)(C)CC(=O)OC)=CC=C1N1C(=O)N(C=2C=CC(=CC=2)C#N)CC1 DCXICDWGXYOAPE-UHFFFAOYSA-N 0.000 description 1
- DSXVQZGHAIQKNT-UHFFFAOYSA-N methyl 3-[4-[3-(4-cyanophenyl)-2-oxoimidazolidin-1-yl]phenyl]propanoate;hydrochloride Chemical compound Cl.C1=CC(CCC(=O)OC)=CC=C1N1C(=O)N(C=2C=CC(=CC=2)C#N)CC1 DSXVQZGHAIQKNT-UHFFFAOYSA-N 0.000 description 1
- JESIWTBEAMFGEY-UHFFFAOYSA-N methyl 3-[4-[3-(4-cyanophenyl)-2-sulfanylideneimidazolidin-1-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1N1C(=S)N(C=2C=CC(=CC=2)C#N)CC1 JESIWTBEAMFGEY-UHFFFAOYSA-N 0.000 description 1
- VMRPXWFNMVZXHC-UHFFFAOYSA-N methyl 3-[4-[3-(4-cyanophenyl)-4-methyl-2-oxo-1h-imidazol-5-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=C(C)N(C=2C=CC(=CC=2)C#N)C(=O)N1 VMRPXWFNMVZXHC-UHFFFAOYSA-N 0.000 description 1
- YXFPXBWQRDXOLA-UHFFFAOYSA-N methyl 3-[4-[3-[3-(2-aminoethyl)phenyl]-2-oxoimidazolidin-1-yl]phenyl]propanoate hydrochloride Chemical compound Cl.C1=CC(CCC(=O)OC)=CC=C1N1C(=O)N(C=2C=C(CCN)C=CC=2)CC1 YXFPXBWQRDXOLA-UHFFFAOYSA-N 0.000 description 1
- OLOREBVVCPCAQQ-UHFFFAOYSA-N methyl 3-[4-[3-[3-(cyanomethyl)phenyl]-2-oxoimidazol-1-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1N1C(=O)N(C=2C=C(CC#N)C=CC=2)C=C1 OLOREBVVCPCAQQ-UHFFFAOYSA-N 0.000 description 1
- MQTSMTBTLRQOCO-UHFFFAOYSA-N methyl 3-[4-[3-[3-(diaminomethylideneamino)phenyl]-2-oxoimidazolidin-1-yl]phenyl]propanoate;hydrochloride Chemical compound Cl.C1=CC(CCC(=O)OC)=CC=C1N1C(=O)N(C=2C=C(NC(N)=N)C=CC=2)CC1 MQTSMTBTLRQOCO-UHFFFAOYSA-N 0.000 description 1
- PHQKUVURNFKCFM-UHFFFAOYSA-N methyl 3-[4-[3-[4-(1-amino-2-methylpropan-2-yl)phenyl]-2-oxoimidazolidin-1-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1N1C(=O)N(C=2C=CC(=CC=2)C(C)(C)CN)CC1 PHQKUVURNFKCFM-UHFFFAOYSA-N 0.000 description 1
- CIEUWBIKYJGUKG-UHFFFAOYSA-N methyl 3-[4-[3-[4-(aminomethyl)-2-methylphenyl]-2-oxoimidazolidin-1-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1N1C(=O)N(C=2C(=CC(CN)=CC=2)C)CC1 CIEUWBIKYJGUKG-UHFFFAOYSA-N 0.000 description 1
- CQKLTVWKKQTEPY-UHFFFAOYSA-N methyl 3-[4-[3-[4-(aminomethyl)-3-fluorophenyl]-2-oxoimidazolidin-1-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1N1C(=O)N(C=2C=C(F)C(CN)=CC=2)CC1 CQKLTVWKKQTEPY-UHFFFAOYSA-N 0.000 description 1
- OHZWKSKHNUWKAB-UHFFFAOYSA-N methyl 3-[4-[3-[4-(aminomethyl)cyclohexyl]-2-oxoimidazolidin-1-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1N1C(=O)N(C2CCC(CN)CC2)CC1 OHZWKSKHNUWKAB-UHFFFAOYSA-N 0.000 description 1
- FAHYATPERKRMMU-UHFFFAOYSA-N methyl 3-[4-[3-[4-(aminomethyl)phenyl]-2-oxo-1,3-diazinan-1-yl]phenyl]propanoate;hydrochloride Chemical compound Cl.C1=CC(CCC(=O)OC)=CC=C1N1C(=O)N(C=2C=CC(CN)=CC=2)CCC1 FAHYATPERKRMMU-UHFFFAOYSA-N 0.000 description 1
- RZWURFZEJVZZHF-UHFFFAOYSA-N methyl 3-[4-[3-[4-(aminomethyl)phenyl]-2-oxoimidazolidin-1-yl]phenyl]propanoate;hydrochloride Chemical compound Cl.C1=CC(CCC(=O)OC)=CC=C1N1C(=O)N(C=2C=CC(CN)=CC=2)CC1 RZWURFZEJVZZHF-UHFFFAOYSA-N 0.000 description 1
- DDKYUGGOKOQQSK-UHFFFAOYSA-N methyl 3-[4-[3-[4-(aminomethyl)phenyl]-4-methyl-2-oxoimidazol-1-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1N1C(=O)N(C=2C=CC(CN)=CC=2)C(C)=C1 DDKYUGGOKOQQSK-UHFFFAOYSA-N 0.000 description 1
- JIYIZJBDJCILGC-UHFFFAOYSA-N methyl 3-[4-[3-[4-(n'-methylcarbamimidoyl)phenyl]-2-oxoimidazolidin-1-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1N1C(=O)N(C=2C=CC(=CC=2)C(N)=NC)CC1 JIYIZJBDJCILGC-UHFFFAOYSA-N 0.000 description 1
- VEXYKSXSOGOJAO-UHFFFAOYSA-N methyl 3-[4-[3-[4-(n-hydroxy-c-methylcarbonimidoyl)phenyl]-2-oxoimidazolidin-1-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1N1C(=O)N(C=2C=CC(=CC=2)C(C)=NO)CC1 VEXYKSXSOGOJAO-UHFFFAOYSA-N 0.000 description 1
- OVHDVVYBQZFGIK-UHFFFAOYSA-N methyl 3-[4-[3-[4-[(e)-n'-ethoxycarbonylcarbamimidoyl]phenyl]-2-oxoimidazolidin-1-yl]phenyl]propanoate Chemical compound C1=CC(C(=N)NC(=O)OCC)=CC=C1N1C(=O)N(C=2C=CC(CCC(=O)OC)=CC=2)CC1 OVHDVVYBQZFGIK-UHFFFAOYSA-N 0.000 description 1
- DABKQVZTPWHWLP-UHFFFAOYSA-N methyl 3-[4-[3-[4-[(e)-n'-methoxycarbonylcarbamimidoyl]phenyl]-2-oxoimidazolidin-1-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1N1C(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)OC)CC1 DABKQVZTPWHWLP-UHFFFAOYSA-N 0.000 description 1
- DVHJTUASDFOWQW-UHFFFAOYSA-N methyl 3-[4-[4-(4-carbamimidoylphenyl)-3-methyl-2-oxoimidazolidin-1-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1N1C(=O)N(C)C(C=2C=CC(=CC=2)C(N)=N)C1 DVHJTUASDFOWQW-UHFFFAOYSA-N 0.000 description 1
- IZEYNAMVXOGIDM-UHFFFAOYSA-N methyl 3-[4-[4-(4-carbamimidoylphenyl)-5-methyl-2-oxo-3-phenylimidazol-1-yl]phenyl]propanoate;hydrochloride Chemical compound Cl.C1=CC(CCC(=O)OC)=CC=C1N1C(=O)N(C=2C=CC=CC=2)C(C=2C=CC(=CC=2)C(N)=N)=C1C IZEYNAMVXOGIDM-UHFFFAOYSA-N 0.000 description 1
- DBDBFSXRNMUGBN-UHFFFAOYSA-N methyl 3-[4-[4-(4-cyanophenyl)-3-methyl-2-oxoimidazol-1-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1N1C(=O)N(C)C(C=2C=CC(=CC=2)C#N)=C1 DBDBFSXRNMUGBN-UHFFFAOYSA-N 0.000 description 1
- QBEANVPHYOGWIN-UHFFFAOYSA-N methyl 3-[4-[4-(4-cyanophenyl)-5-methyl-2-oxo-3-phenylimidazol-1-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1N1C(=O)N(C=2C=CC=CC=2)C(C=2C=CC(=CC=2)C#N)=C1C QBEANVPHYOGWIN-UHFFFAOYSA-N 0.000 description 1
- AJWAGQBXJAYTLF-UHFFFAOYSA-N methyl 3-[4-[5-(4-carbamimidoylphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-2-yl]phenyl]propanoate;hydrochloride Chemical compound Cl.C1=CC(CCC(=O)OC)=CC=C1N1S(=O)(=O)N(C=2C=CC(=CC=2)C(N)=N)CC1 AJWAGQBXJAYTLF-UHFFFAOYSA-N 0.000 description 1
- GABGNSIVIULHFN-UHFFFAOYSA-N methyl 3-[4-[5-(4-carbamimidoylphenyl)-2-oxo-1h-imidazol-3-yl]phenyl]propanoate;hydrochloride Chemical compound Cl.C1=CC(CCC(=O)OC)=CC=C1N1C(=O)NC(C=2C=CC(=CC=2)C(N)=N)=C1 GABGNSIVIULHFN-UHFFFAOYSA-N 0.000 description 1
- QIHIJLVCTHRYOT-UHFFFAOYSA-N methyl 3-[4-[5-(4-carbamimidoylphenyl)-3-oxo-1h-1,2,4-triazol-2-yl]phenyl]propanoate;hydrochloride Chemical compound Cl.C1=CC(CCC(=O)OC)=CC=C1N1C(=O)N=C(C=2C=CC(=CC=2)C(N)=N)N1 QIHIJLVCTHRYOT-UHFFFAOYSA-N 0.000 description 1
- XIMFDTVVYSGSEJ-UHFFFAOYSA-N methyl 3-[4-[5-[4-[(e)-n'-methoxycarbonylcarbamimidoyl]phenyl]-1,1-dioxo-1,2,5-thiadiazolidin-2-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1N1S(=O)(=O)N(C=2C=CC(=CC=2)C(=N)NC(=O)OC)CC1 XIMFDTVVYSGSEJ-UHFFFAOYSA-N 0.000 description 1
- QLQQNCXSHOKPKN-UHFFFAOYSA-N methyl 3-[4-[[2-(4-cyanophenyl)-2-oxoethyl]amino]phenyl]prop-2-enoate Chemical compound C1=CC(C=CC(=O)OC)=CC=C1NCC(=O)C1=CC=C(C#N)C=C1 QLQQNCXSHOKPKN-UHFFFAOYSA-N 0.000 description 1
- KOLIWBZDVYITNS-UHFFFAOYSA-N methyl 4-(2-chloroethyl)benzoate Chemical compound COC(=O)C1=CC=C(CCCl)C=C1 KOLIWBZDVYITNS-UHFFFAOYSA-N 0.000 description 1
- DRGJKGKELPYLBI-UHFFFAOYSA-N methyl 4-[2-[3-(4-carbamimidoylphenyl)-2-oxoimidazolidin-1-yl]ethyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CCN1C(=O)N(C=2C=CC(=CC=2)C(N)=N)CC1 DRGJKGKELPYLBI-UHFFFAOYSA-N 0.000 description 1
- FCAAMTWLXPCNIV-UHFFFAOYSA-N methyl 4-[2-[3-(4-cyanophenyl)-2-oxoimidazol-1-yl]ethyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CCN1C(=O)N(C=2C=CC(=CC=2)C#N)C=C1 FCAAMTWLXPCNIV-UHFFFAOYSA-N 0.000 description 1
- JABREZMUNKSPLP-UHFFFAOYSA-N methyl 4-[2-[3-(4-cyanophenyl)-2-oxoimidazolidin-1-yl]ethyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CCN1C(=O)N(C=2C=CC(=CC=2)C#N)CC1 JABREZMUNKSPLP-UHFFFAOYSA-N 0.000 description 1
- PWGQCXXISMCRCA-UHFFFAOYSA-N methyl 4-[3-[2-(4-carbamimidoylphenyl)-2-hydroxyethyl]-2-oxoimidazolidin-1-yl]butanoate Chemical compound O=C1N(CCCC(=O)OC)CCN1CC(O)C1=CC=C(C(N)=N)C=C1 PWGQCXXISMCRCA-UHFFFAOYSA-N 0.000 description 1
- HOGNLOLTADBVKW-UHFFFAOYSA-N methyl 4-[3-[2-(4-carbamimidoylphenyl)-2-oxoethyl]-2-oxoimidazolidin-1-yl]butanoate;hydrochloride Chemical compound Cl.O=C1N(CCCC(=O)OC)CCN1CC(=O)C1=CC=C(C(N)=N)C=C1 HOGNLOLTADBVKW-UHFFFAOYSA-N 0.000 description 1
- JTKCMVJCBSWTPK-UHFFFAOYSA-N methyl 4-[4-[(4-cyanophenyl)carbamoyl-(2-hydroxyethyl)amino]phenyl]butanoate Chemical compound C1=CC(CCCC(=O)OC)=CC=C1N(CCO)C(=O)NC1=CC=C(C#N)C=C1 JTKCMVJCBSWTPK-UHFFFAOYSA-N 0.000 description 1
- MSMMASUSFGXPFQ-UHFFFAOYSA-N methyl 4-[4-[3-(4-carbamimidoylphenyl)-2-oxoimidazolidin-1-yl]phenyl]butanoate;hydrochloride Chemical compound Cl.C1=CC(CCCC(=O)OC)=CC=C1N1C(=O)N(C=2C=CC(=CC=2)C(N)=N)CC1 MSMMASUSFGXPFQ-UHFFFAOYSA-N 0.000 description 1
- MWDBYVVVKMBTLI-UHFFFAOYSA-N methyl 5-[3-(4-carbamimidoylphenyl)-2-oxoimidazolidin-1-yl]pentanoate;hydrochloride Chemical compound Cl.O=C1N(CCCCC(=O)OC)CCN1C1=CC=C(C(N)=N)C=C1 MWDBYVVVKMBTLI-UHFFFAOYSA-N 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- CCRCUPLGCSFEDV-BQYQJAHWSA-N methyl trans-cinnamate Chemical compound COC(=O)\C=C\C1=CC=CC=C1 CCRCUPLGCSFEDV-BQYQJAHWSA-N 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229940117953 phenylisothiocyanate Drugs 0.000 description 1
- ZAEQTGTVGUJEFV-UHFFFAOYSA-N phenylmethanesulfonate;pyridin-1-ium Chemical compound C1=CC=[NH+]C=C1.[O-]S(=O)(=O)CC1=CC=CC=C1 ZAEQTGTVGUJEFV-UHFFFAOYSA-N 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 210000004623 platelet-rich plasma Anatomy 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- QETSJDXFTIVELG-UHFFFAOYSA-N propan-2-yl 3-[4-[3-(4-carbamimidoylphenyl)-2-oxoimidazol-1-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC(C)C)=CC=C1N1C(=O)N(C=2C=CC(=CC=2)C(N)=N)C=C1 QETSJDXFTIVELG-UHFFFAOYSA-N 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 150000003303 ruthenium Chemical class 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 150000003459 sulfonic acid esters Chemical group 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- 235000015523 tannic acid Nutrition 0.000 description 1
- SJMDMGHPMLKLHQ-UHFFFAOYSA-N tert-butyl 2-aminoacetate Chemical compound CC(C)(C)OC(=O)CN SJMDMGHPMLKLHQ-UHFFFAOYSA-N 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- LLZRNZOLAXHGLL-UHFFFAOYSA-J titanic acid Chemical compound O[Ti](O)(O)O LLZRNZOLAXHGLL-UHFFFAOYSA-J 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- ZTWIEIFKPFJRLV-UHFFFAOYSA-K trichlororuthenium;trihydrate Chemical compound O.O.O.Cl[Ru](Cl)Cl ZTWIEIFKPFJRLV-UHFFFAOYSA-K 0.000 description 1
- 238000005583 trifluoroacetylation reaction Methods 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 229910009112 xH2O Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/10—1,2,5-Thiadiazoles; Hydrogenated 1,2,5-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/70—One oxygen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/26—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
- C07D239/10—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
- C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Vascular Medicine (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Hydrogenated Pyridines (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Silicon Polymers (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4107857A DE4107857A1 (de) | 1991-03-12 | 1991-03-12 | Cyclische harnstoffderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
Publications (1)
Publication Number | Publication Date |
---|---|
SK74592A3 true SK74592A3 (en) | 1993-12-08 |
Family
ID=6427033
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SK745-92A SK74592A3 (en) | 1991-03-12 | 1992-03-12 | Cyclic urea derivatives, their preparation and pharmaceutical agents with their content |
Country Status (23)
Country | Link |
---|---|
US (3) | US5276049A (no) |
EP (1) | EP0503548B1 (no) |
JP (1) | JPH04368372A (no) |
KR (1) | KR920018031A (no) |
AT (1) | ATE154013T1 (no) |
AU (1) | AU654340B2 (no) |
CA (1) | CA2062655A1 (no) |
CZ (1) | CZ74592A3 (no) |
DE (2) | DE4107857A1 (no) |
DK (1) | DK0503548T3 (no) |
ES (1) | ES2104754T3 (no) |
FI (1) | FI921030A (no) |
GR (1) | GR3024504T3 (no) |
HU (1) | HUT60722A (no) |
IE (1) | IE920781A1 (no) |
IL (1) | IL101203A (no) |
MX (1) | MX9201068A (no) |
NO (1) | NO920957L (no) |
NZ (1) | NZ241928A (no) |
PL (1) | PL293795A1 (no) |
SK (1) | SK74592A3 (no) |
TW (1) | TW221811B (no) |
ZA (1) | ZA921804B (no) |
Families Citing this family (65)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4134467A1 (de) * | 1991-10-18 | 1993-04-22 | Thomae Gmbh Dr K | Heterobiarylderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
DE4124942A1 (de) * | 1991-07-27 | 1993-01-28 | Thomae Gmbh Dr K | 5-gliedrige heterocyclen, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
USRE37781E1 (en) | 1991-10-11 | 2002-07-02 | Dupont Pharmaceuticals Company | Substituted cyclic carbonyls and derivatives thereof useful as retroviral protease inhibitors |
WO1993018058A1 (en) * | 1992-03-06 | 1993-09-16 | G.D. Searle & Co. | Peptides mimics useful as platelet aggregation inhibitors |
DE4213931A1 (de) * | 1992-04-28 | 1993-11-04 | Thomae Gmbh Dr K | Cyclische iminoderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
DE4213919A1 (de) * | 1992-04-28 | 1993-11-04 | Thomae Gmbh Dr K | Cyclische iminoderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
ATE140225T1 (de) * | 1992-04-28 | 1996-07-15 | Thomae Gmbh Dr K | Tritiumarkierte fibrinogen-rezeptor-antagonisten, deren verwendung und verfahren zur ihrer herstellung |
SK94393A3 (en) * | 1992-09-11 | 1994-08-10 | Thomae Gmbh Dr K | Cyclic derivatives of urea, process for their production and their pharmaceutical agents with the content of those |
FR2700337B1 (fr) * | 1993-01-11 | 1995-04-14 | Lafon Labor | Dérivés d'imidazopyridine-2-one, leur procédé de préparation et leur utilisation en thérapeutique. |
DE4332168A1 (de) * | 1993-02-22 | 1995-03-23 | Thomae Gmbh Dr K | Cyclische Derivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
US5753659A (en) * | 1993-03-29 | 1998-05-19 | Zeneca Limited | Heterocyclic compouds |
US5750754A (en) * | 1993-03-29 | 1998-05-12 | Zeneca Limited | Heterocyclic compounds |
US5652242A (en) * | 1993-03-29 | 1997-07-29 | Zeneca Limited | Heterocyclic derivatives |
CA2155307A1 (en) * | 1993-03-29 | 1994-10-13 | Michael Garth Wayne | Heterocyclic compounds as platelet aggregation inhibitors |
GB9406143D0 (en) * | 1993-03-29 | 1994-05-18 | Zeneca Ltd | Heterocyclic derivatives |
GB9313268D0 (en) * | 1993-06-28 | 1993-08-11 | Zeneca Ltd | Chemical compounds |
US5463011A (en) * | 1993-06-28 | 1995-10-31 | Zeneca Limited | Acid derivatives |
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CA697572A (en) * | 1964-11-10 | W. Luckenbaugh Raymond | Substituted imidazolinones | |
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DE2724819A1 (de) * | 1977-06-02 | 1978-12-07 | Hoechst Ag | Bis-phenyl-triazolone und verfahren zu ihrer herstellung |
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DE3604040A1 (de) * | 1986-02-08 | 1987-08-13 | Hoechst Ag | 1-aryl-imidazolin-2-thione, verfahren zu ihrer herstellung sowie ihre verwendung im pflanzenschutz |
US4724261A (en) * | 1986-11-24 | 1988-02-09 | Stauffer Chemical Company | Cyclic ureas |
FR2618779B1 (fr) * | 1987-07-31 | 1991-01-04 | Poudres & Explosifs Ste Nale | Nouveau procede de preparation des 1,2,4-triazol-3-ones |
-
1991
- 1991-03-12 DE DE4107857A patent/DE4107857A1/de not_active Withdrawn
-
1992
- 1992-03-10 DE DE59208559T patent/DE59208559D1/de not_active Expired - Fee Related
- 1992-03-10 EP EP92104045A patent/EP0503548B1/de not_active Expired - Lifetime
- 1992-03-10 DK DK92104045.7T patent/DK0503548T3/da active
- 1992-03-10 FI FI921030A patent/FI921030A/fi unknown
- 1992-03-10 AT AT92104045T patent/ATE154013T1/de not_active IP Right Cessation
- 1992-03-10 ES ES92104045T patent/ES2104754T3/es not_active Expired - Lifetime
- 1992-03-11 HU HU9200823A patent/HUT60722A/hu unknown
- 1992-03-11 NZ NZ241928A patent/NZ241928A/en unknown
- 1992-03-11 PL PL29379592A patent/PL293795A1/xx unknown
- 1992-03-11 CA CA002062655A patent/CA2062655A1/en not_active Abandoned
- 1992-03-11 NO NO92920957A patent/NO920957L/no unknown
- 1992-03-11 US US07/849,557 patent/US5276049A/en not_active Expired - Fee Related
- 1992-03-11 IL IL10120392A patent/IL101203A/en not_active IP Right Cessation
- 1992-03-11 KR KR1019920003953A patent/KR920018031A/ko not_active Application Discontinuation
- 1992-03-11 AU AU12803/92A patent/AU654340B2/en not_active Ceased
- 1992-03-11 MX MX9201068A patent/MX9201068A/es unknown
- 1992-03-11 ZA ZA921804A patent/ZA921804B/xx unknown
- 1992-03-11 IE IE078192A patent/IE920781A1/en not_active Application Discontinuation
- 1992-03-12 JP JP4053171A patent/JPH04368372A/ja active Pending
- 1992-03-12 SK SK745-92A patent/SK74592A3/sk unknown
- 1992-03-12 CZ CS92745A patent/CZ74592A3/cs unknown
- 1992-03-12 TW TW081101892A patent/TW221811B/zh active
-
1993
- 1993-10-28 US US08/144,909 patent/US5478942A/en not_active Expired - Fee Related
-
1995
- 1995-08-29 US US08/521,338 patent/US5650424A/en not_active Expired - Fee Related
-
1997
- 1997-08-21 GR GR970402143T patent/GR3024504T3/el unknown
Also Published As
Publication number | Publication date |
---|---|
PL293795A1 (en) | 1993-03-08 |
GR3024504T3 (en) | 1997-11-28 |
NO920957L (no) | 1992-09-14 |
JPH04368372A (ja) | 1992-12-21 |
US5276049A (en) | 1994-01-04 |
US5478942A (en) | 1995-12-26 |
DK0503548T3 (da) | 1997-11-03 |
NO920957D0 (no) | 1992-03-11 |
NZ241928A (en) | 1994-06-27 |
CA2062655A1 (en) | 1992-09-13 |
DE59208559D1 (de) | 1997-07-10 |
US5650424A (en) | 1997-07-22 |
ES2104754T3 (es) | 1997-10-16 |
IL101203A (en) | 1995-12-31 |
DE4107857A1 (de) | 1992-09-17 |
MX9201068A (es) | 1992-09-01 |
AU654340B2 (en) | 1994-11-03 |
HUT60722A (en) | 1992-10-28 |
FI921030A0 (fi) | 1992-03-10 |
AU1280392A (en) | 1992-09-17 |
ATE154013T1 (de) | 1997-06-15 |
HU9200823D0 (en) | 1992-05-28 |
ZA921804B (en) | 1993-09-13 |
IL101203A0 (en) | 1992-11-15 |
IE920781A1 (en) | 1992-09-23 |
TW221811B (no) | 1994-03-21 |
FI921030A (fi) | 1992-09-13 |
CZ74592A3 (en) | 1993-03-17 |
EP0503548B1 (de) | 1997-06-04 |
EP0503548A1 (de) | 1992-09-16 |
KR920018031A (ko) | 1992-10-21 |
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