DE4124942A1 - 5-gliedrige heterocyclen, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel - Google Patents
5-gliedrige heterocyclen, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittelInfo
- Publication number
- DE4124942A1 DE4124942A1 DE4124942A DE4124942A DE4124942A1 DE 4124942 A1 DE4124942 A1 DE 4124942A1 DE 4124942 A DE4124942 A DE 4124942A DE 4124942 A DE4124942 A DE 4124942A DE 4124942 A1 DE4124942 A1 DE 4124942A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- phenyl
- carbon atoms
- atom
- radicals
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims description 98
- 238000000034 method Methods 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 239000003814 drug Substances 0.000 title claims description 4
- -1 cyclic imine Chemical class 0.000 claims description 202
- 150000003254 radicals Chemical class 0.000 claims description 152
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 116
- 125000004432 carbon atom Chemical group C* 0.000 claims description 109
- 125000000217 alkyl group Chemical group 0.000 claims description 77
- 229910052757 nitrogen Inorganic materials 0.000 claims description 77
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 58
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 54
- 125000003545 alkoxy group Chemical group 0.000 claims description 54
- 239000000203 mixture Substances 0.000 claims description 43
- 239000000460 chlorine Substances 0.000 claims description 37
- 229910052801 chlorine Inorganic materials 0.000 claims description 37
- 229910052717 sulfur Inorganic materials 0.000 claims description 37
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 35
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 34
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
- 125000002947 alkylene group Chemical group 0.000 claims description 31
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 30
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 30
- 229910052760 oxygen Inorganic materials 0.000 claims description 30
- 239000001301 oxygen Substances 0.000 claims description 30
- 238000002360 preparation method Methods 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 30
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 24
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 24
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 24
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 21
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 21
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 20
- 125000004647 alkyl sulfenyl group Chemical group 0.000 claims description 20
- 239000011737 fluorine Substances 0.000 claims description 20
- 229910052731 fluorine Inorganic materials 0.000 claims description 20
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 20
- 239000011593 sulfur Substances 0.000 claims description 20
- 125000004450 alkenylene group Chemical group 0.000 claims description 19
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 19
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 19
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
- 125000001246 bromo group Chemical group Br* 0.000 claims description 18
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 18
- 125000005550 pyrazinylene group Chemical group 0.000 claims description 18
- 125000005576 pyrimidinylene group Chemical group 0.000 claims description 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 16
- 125000005140 aralkylsulfonyl group Chemical group 0.000 claims description 16
- 125000004429 atom Chemical group 0.000 claims description 16
- 125000005551 pyridylene group Chemical group 0.000 claims description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 15
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 14
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 14
- 125000004434 sulfur atom Chemical group 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 12
- 150000001721 carbon Chemical group 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 10
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 10
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 10
- 150000007522 mineralic acids Chemical class 0.000 claims description 9
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 8
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims description 8
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 8
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 150000007524 organic acids Chemical class 0.000 claims description 8
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 8
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 6
- 230000000269 nucleophilic effect Effects 0.000 claims description 6
- 235000005985 organic acids Nutrition 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 6
- 125000005558 triazinylene group Chemical group 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- ARGCQEVBJHPOGB-UHFFFAOYSA-N 2,5-dihydrofuran Chemical compound C1OCC=C1 ARGCQEVBJHPOGB-UHFFFAOYSA-N 0.000 claims description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 4
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 4
- 125000005156 substituted alkylene group Chemical group 0.000 claims description 4
- 125000005717 substituted cycloalkylene group Chemical group 0.000 claims description 4
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 4
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 3
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical class C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- 230000008619 cell matrix interaction Effects 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 claims description 3
- 238000001149 thermolysis Methods 0.000 claims description 3
- XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical class OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 claims description 2
- MUZIZEZCKKMZRT-UHFFFAOYSA-N 1,2-dithiolane Chemical class C1CSSC1 MUZIZEZCKKMZRT-UHFFFAOYSA-N 0.000 claims description 2
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical class C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 2
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical class C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 claims description 2
- IMLSAISZLJGWPP-UHFFFAOYSA-N 1,3-dithiolane Chemical class C1CSCS1 IMLSAISZLJGWPP-UHFFFAOYSA-N 0.000 claims description 2
- DQLOTKZORORBPO-UHFFFAOYSA-N 1,3-dithiolane 1,1,3,3-tetraoxide Chemical class O=S1(=O)CCS(=O)(=O)C1 DQLOTKZORORBPO-UHFFFAOYSA-N 0.000 claims description 2
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical class C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 2
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical class C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical class C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 2
- OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 claims description 2
- KEQTWHPMSVAFDA-UHFFFAOYSA-N 2,3-dihydro-1h-pyrazole Chemical class C1NNC=C1 KEQTWHPMSVAFDA-UHFFFAOYSA-N 0.000 claims description 2
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 claims description 2
- MPTKDOQUXZAHPJ-UHFFFAOYSA-N 2,3-dihydroindazole Chemical class C1=CC=C2CN[N]C2=C1 MPTKDOQUXZAHPJ-UHFFFAOYSA-N 0.000 claims description 2
- WURYWHAKEJHAOV-UHFFFAOYSA-N 2,5-dihydrothiophene Chemical compound C1SCC=C1 WURYWHAKEJHAOV-UHFFFAOYSA-N 0.000 claims description 2
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical class C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims description 2
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical class C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims description 2
- ZBJCVPFNYVAJQS-UHFFFAOYSA-N 3-[1-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]imidazol-4-yl]-2-hydroxypropanoic acid Chemical compound C1=CC(C(=N)N)=CC=C1C1=CC=C(N2C=C(CC(O)C(O)=O)N=C2)N=N1 ZBJCVPFNYVAJQS-UHFFFAOYSA-N 0.000 claims description 2
- ZFJXQZDHZQNHNA-UHFFFAOYSA-N 3-[1-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]imidazol-4-yl]propanoic acid Chemical compound C1=CC(C(=N)N)=CC=C1C1=CC=C(N2C=C(CCC(O)=O)N=C2)N=N1 ZFJXQZDHZQNHNA-UHFFFAOYSA-N 0.000 claims description 2
- LWMBAXOYBMILJM-UHFFFAOYSA-N 3-[1-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]indol-3-yl]propanoic acid Chemical compound C1=CC(C(=N)N)=CC=C1C1=CC=C(N2C3=CC=CC=C3C(CCC(O)=O)=C2)N=N1 LWMBAXOYBMILJM-UHFFFAOYSA-N 0.000 claims description 2
- KPUNZOASCONSFC-UHFFFAOYSA-N 3-[4-[3-(4-carbamimidoylphenyl)-1h-1,2,4-triazol-5-yl]phenyl]propanoic acid Chemical compound C1=CC(C(=N)N)=CC=C1C1=NNC(C=2C=CC(CCC(O)=O)=CC=2)=N1 KPUNZOASCONSFC-UHFFFAOYSA-N 0.000 claims description 2
- AGKMJXCYUQOHIJ-UHFFFAOYSA-N 3-[4-[5-(4-carbamimidoylphenyl)tetrazol-2-yl]phenyl]propanoic acid Chemical compound C1=CC(C(=N)N)=CC=C1C1=NN(C=2C=CC(CCC(O)=O)=CC=2)N=N1 AGKMJXCYUQOHIJ-UHFFFAOYSA-N 0.000 claims description 2
- CJPFYMPKJYWIAA-UHFFFAOYSA-N 3-[5-[4-(4-carbamimidoylphenyl)phenyl]tetrazol-2-yl]propanoic acid Chemical compound C1=CC(C(=N)N)=CC=C1C1=CC=C(C2=NN(CCC(O)=O)N=N2)C=C1 CJPFYMPKJYWIAA-UHFFFAOYSA-N 0.000 claims description 2
- MCGBIXXDQFWVDW-UHFFFAOYSA-N 4,5-dihydro-1h-pyrazole Chemical class C1CC=NN1 MCGBIXXDQFWVDW-UHFFFAOYSA-N 0.000 claims description 2
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 2
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical class C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical class C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical class C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical class C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- 125000003713 acetylimino group Chemical group [H]C([H])([H])C(=O)N=[*] 0.000 claims description 2
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims description 2
- 125000006294 amino alkylene group Chemical group 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
- MXMZCLLIUQEKSN-UHFFFAOYSA-N benzimidazoline Chemical class C1=CC=C2NCNC2=C1 MXMZCLLIUQEKSN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical class C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 2
- QNLOWBMKUIXCOW-UHFFFAOYSA-N indol-2-one Chemical class C1=CC=CC2=NC(=O)C=C21 QNLOWBMKUIXCOW-UHFFFAOYSA-N 0.000 claims description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Chemical class CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Chemical class C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 2
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical class C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 claims description 2
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical class C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims description 2
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical class C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical class C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- RGSBMOXJZUGVTG-UHFFFAOYSA-N methyl 3-[1-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]indol-3-yl]propanoate Chemical compound C12=CC=CC=C2C(CCC(=O)OC)=CN1C(N=N1)=CC=C1C1=CC=C(C(N)=N)C=C1 RGSBMOXJZUGVTG-UHFFFAOYSA-N 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 230000001681 protective effect Effects 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 2
- ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 claims description 2
- 150000003536 tetrazoles Chemical class 0.000 claims description 2
- 150000003557 thiazoles Chemical class 0.000 claims description 2
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical class C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- AJENTUFGLPVHNS-UHFFFAOYSA-N 2-amino-3-[1-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(CC(N)C(O)=O)=CN1C1=CC=C(C=2C=CC(=CC=2)C(N)=N)N=N1 AJENTUFGLPVHNS-UHFFFAOYSA-N 0.000 claims 1
- NGWOGPJKZVPROF-UHFFFAOYSA-N 3-[4-[4-(4-carbamimidoylphenyl)-1-methylimidazol-2-yl]phenyl]propanoic acid Chemical compound CN1C=C(C=2C=CC(=CC=2)C(N)=N)N=C1C1=CC=C(CCC(O)=O)C=C1 NGWOGPJKZVPROF-UHFFFAOYSA-N 0.000 claims 1
- NALBLJLOBICXRH-UHFFFAOYSA-N dinitrogen monohydride Chemical compound N=[N] NALBLJLOBICXRH-UHFFFAOYSA-N 0.000 claims 1
- WJJXCNMWZQOQHE-UHFFFAOYSA-N methyl 2-amino-3-[1-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]imidazol-4-yl]propanoate Chemical compound C1=NC(CC(N)C(=O)OC)=CN1C1=CC=C(C=2C=CC(=CC=2)C(N)=N)N=N1 WJJXCNMWZQOQHE-UHFFFAOYSA-N 0.000 claims 1
- JICXRCOSKQBGPZ-UHFFFAOYSA-N methyl 3-[1-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]imidazol-4-yl]propanoate Chemical compound C1=NC(CCC(=O)OC)=CN1C1=CC=C(C=2C=CC(=CC=2)C(N)=N)N=N1 JICXRCOSKQBGPZ-UHFFFAOYSA-N 0.000 claims 1
- VVZOQJQRABDHAS-UHFFFAOYSA-N methyl 3-[4-[3-(4-carbamimidoylphenyl)-1h-1,2,4-triazol-5-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=NC(C=2C=CC(=CC=2)C(N)=N)=NN1 VVZOQJQRABDHAS-UHFFFAOYSA-N 0.000 claims 1
- LIOPJDZQFZLCEL-UHFFFAOYSA-N methyl 3-[4-[4-(4-carbamimidoylphenyl)-1-methylimidazol-2-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=NC(C=2C=CC(=CC=2)C(N)=N)=CN1C LIOPJDZQFZLCEL-UHFFFAOYSA-N 0.000 claims 1
- DPMRPQRAEWNFNG-UHFFFAOYSA-N methyl 3-[4-[5-(4-carbamimidoylphenyl)-1h-imidazol-2-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=NC=C(C=2C=CC(=CC=2)C(N)=N)N1 DPMRPQRAEWNFNG-UHFFFAOYSA-N 0.000 claims 1
- LZCQYQIAQBOLBL-UHFFFAOYSA-N methyl 3-[4-[5-(4-carbamimidoylphenyl)tetrazol-2-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1N1N=C(C=2C=CC(=CC=2)C(N)=N)N=N1 LZCQYQIAQBOLBL-UHFFFAOYSA-N 0.000 claims 1
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- DGESEWLMNFSWOP-UHFFFAOYSA-N methyl 3-[1-[5-(4-carbamimidoylphenyl)-4-methylpyrimidin-2-yl]imidazol-4-yl]propanoate Chemical compound C1=NC(CCC(=O)OC)=CN1C1=NC=C(C=2C=CC(=CC=2)C(N)=N)C(C)=N1 DGESEWLMNFSWOP-UHFFFAOYSA-N 0.000 description 1
- ZDBCCBLYARIRIF-UHFFFAOYSA-N methyl 3-[1-[5-(4-carbamimidoylphenyl)pyridin-2-yl]imidazol-4-yl]propanoate Chemical compound C1=NC(CCC(=O)OC)=CN1C1=CC=C(C=2C=CC(=CC=2)C(N)=N)C=N1 ZDBCCBLYARIRIF-UHFFFAOYSA-N 0.000 description 1
- AXCHKTAPEDJRBF-UHFFFAOYSA-N methyl 3-[1-[5-(4-carbamimidoylphenyl)pyrimidin-2-yl]imidazol-4-yl]propanoate Chemical compound C1=NC(CCC(=O)OC)=CN1C1=NC=C(C=2C=CC(=CC=2)C(N)=N)C=N1 AXCHKTAPEDJRBF-UHFFFAOYSA-N 0.000 description 1
- VJRPRGKRDLXTOS-UHFFFAOYSA-N methyl 3-[1-[6-(4-carbamimidoyl-2-fluorophenyl)pyridazin-3-yl]imidazol-4-yl]propanoate Chemical compound C1=NC(CCC(=O)OC)=CN1C1=CC=C(C=2C(=CC(=CC=2)C(N)=N)F)N=N1 VJRPRGKRDLXTOS-UHFFFAOYSA-N 0.000 description 1
- FGDFTULSMFENJZ-UHFFFAOYSA-N methyl 3-[1-[6-(4-carbamimidoyl-2-methoxyphenyl)pyridazin-3-yl]imidazol-4-yl]propanoate Chemical compound C1=NC(CCC(=O)OC)=CN1C1=CC=C(C=2C(=CC(=CC=2)C(N)=N)OC)N=N1 FGDFTULSMFENJZ-UHFFFAOYSA-N 0.000 description 1
- ZBSFITYNSIZBEO-UHFFFAOYSA-N methyl 3-[1-[6-(4-carbamimidoyl-2-methylphenyl)pyridazin-3-yl]imidazol-4-yl]propanoate Chemical compound C1=NC(CCC(=O)OC)=CN1C1=CC=C(C=2C(=CC(=CC=2)C(N)=N)C)N=N1 ZBSFITYNSIZBEO-UHFFFAOYSA-N 0.000 description 1
- BGYDTPOUGUSODM-UHFFFAOYSA-N methyl 3-[1-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]-2-(2-phenylethyl)imidazol-4-yl]propanoate Chemical compound N=1C(CCC(=O)OC)=CN(C=2N=NC(=CC=2)C=2C=CC(=CC=2)C(N)=N)C=1CCC1=CC=CC=C1 BGYDTPOUGUSODM-UHFFFAOYSA-N 0.000 description 1
- NWFWPZGVFVOQDP-UHFFFAOYSA-N methyl 3-[1-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]-2-hexylimidazol-4-yl]propanoate Chemical compound CCCCCCC1=NC(CCC(=O)OC)=CN1C1=CC=C(C=2C=CC(=CC=2)C(N)=N)N=N1 NWFWPZGVFVOQDP-UHFFFAOYSA-N 0.000 description 1
- BWQYXMCLBNAQNM-UHFFFAOYSA-N methyl 3-[1-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]-2-methylimidazol-4-yl]propanoate Chemical compound CC1=NC(CCC(=O)OC)=CN1C1=CC=C(C=2C=CC(=CC=2)C(N)=N)N=N1 BWQYXMCLBNAQNM-UHFFFAOYSA-N 0.000 description 1
- RQMGNEPRHUBXQT-UHFFFAOYSA-N methyl 3-[1-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]-2-phenylimidazol-4-yl]propanoate Chemical compound N=1C(CCC(=O)OC)=CN(C=2N=NC(=CC=2)C=2C=CC(=CC=2)C(N)=N)C=1C1=CC=CC=C1 RQMGNEPRHUBXQT-UHFFFAOYSA-N 0.000 description 1
- HEXKJCRVNQAKFE-UHFFFAOYSA-N methyl 3-[1-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]-2-propan-2-ylimidazol-4-yl]propanoate Chemical compound CC(C)C1=NC(CCC(=O)OC)=CN1C1=CC=C(C=2C=CC(=CC=2)C(N)=N)N=N1 HEXKJCRVNQAKFE-UHFFFAOYSA-N 0.000 description 1
- MKSDBHPZYTZLRM-UHFFFAOYSA-N methyl 3-[1-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]-2-pyridin-3-ylimidazol-4-yl]propanoate Chemical compound N=1C(CCC(=O)OC)=CN(C=2N=NC(=CC=2)C=2C=CC(=CC=2)C(N)=N)C=1C1=CC=CN=C1 MKSDBHPZYTZLRM-UHFFFAOYSA-N 0.000 description 1
- KIRBOPLKTFIWRM-UHFFFAOYSA-N methyl 3-[1-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]imidazol-2-yl]-2-(dimethylamino)propanoate Chemical compound COC(=O)C(N(C)C)CC1=NC=CN1C1=CC=C(C=2C=CC(=CC=2)C(N)=N)N=N1 KIRBOPLKTFIWRM-UHFFFAOYSA-N 0.000 description 1
- HZVDGRHGPQHUDI-UHFFFAOYSA-N methyl 3-[1-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]imidazol-4-yl]-2-hydroxypropanoate Chemical compound C1=NC(CC(O)C(=O)OC)=CN1C1=CC=C(C=2C=CC(=CC=2)C(N)=N)N=N1 HZVDGRHGPQHUDI-UHFFFAOYSA-N 0.000 description 1
- YDDHVOUMXQBYCI-UHFFFAOYSA-N methyl 3-[1-[6-(4-cyanophenyl)pyridazin-3-yl]imidazol-4-yl]-2-hydroxypropanoate Chemical compound C1=NC(CC(O)C(=O)OC)=CN1C1=CC=C(C=2C=CC(=CC=2)C#N)N=N1 YDDHVOUMXQBYCI-UHFFFAOYSA-N 0.000 description 1
- ISQRIQNTUJONOW-UHFFFAOYSA-N methyl 3-[1-[6-[4-(n'-butylcarbamimidoyl)phenyl]pyridazin-3-yl]imidazol-4-yl]propanoate Chemical compound C1=CC(C(=N)NCCCC)=CC=C1C1=CC=C(N2C=C(CCC(=O)OC)N=C2)N=N1 ISQRIQNTUJONOW-UHFFFAOYSA-N 0.000 description 1
- JWENNAYCOQMQMG-UHFFFAOYSA-N methyl 3-[2-[1-(5-carbamimidoylpyridin-2-yl)piperidin-4-yl]-1,3-thiazol-4-yl]propanoate Chemical compound COC(=O)CCC1=CSC(C2CCN(CC2)C=2N=CC(=CC=2)C(N)=N)=N1 JWENNAYCOQMQMG-UHFFFAOYSA-N 0.000 description 1
- WJJGSDJSRUTBTH-UHFFFAOYSA-N methyl 3-[2-[4-(4-carbamimidoylphenyl)phenyl]-1,3-thiazol-4-yl]propanoate Chemical compound COC(=O)CCC1=CSC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C(N)=N)=N1 WJJGSDJSRUTBTH-UHFFFAOYSA-N 0.000 description 1
- OYRCTCANAZVVPT-UHFFFAOYSA-N methyl 3-[2-amino-4-[5-(4-carbamimidoylphenyl)-1h-imidazol-2-yl]phenyl]propanoate Chemical compound C1=C(N)C(CCC(=O)OC)=CC=C1C1=NC=C(C=2C=CC(=CC=2)C(N)=N)N1 OYRCTCANAZVVPT-UHFFFAOYSA-N 0.000 description 1
- YKNJPOURDFOCHT-UHFFFAOYSA-N methyl 3-[2-benzamido-4-[5-(4-carbamimidoylphenyl)-1h-imidazol-2-yl]phenyl]propanoate Chemical compound COC(=O)CCC1=CC=C(C=2NC=C(N=2)C=2C=CC(=CC=2)C(N)=N)C=C1NC(=O)C1=CC=CC=C1 YKNJPOURDFOCHT-UHFFFAOYSA-N 0.000 description 1
- WCQSAHGERVPZGV-UHFFFAOYSA-N methyl 3-[3-[4-(4-carbamimidoylphenyl)phenyl]-1h-pyrazol-5-yl]propanoate Chemical compound N1C(CCC(=O)OC)=CC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C(N)=N)=N1 WCQSAHGERVPZGV-UHFFFAOYSA-N 0.000 description 1
- QMVVEEGSRCWWLT-UHFFFAOYSA-N methyl 3-[4-(4-piperidin-4-ylphenyl)-1,3-thiazol-2-yl]propanoate Chemical compound S1C(CCC(=O)OC)=NC(C=2C=CC(=CC=2)C2CCNCC2)=C1 QMVVEEGSRCWWLT-UHFFFAOYSA-N 0.000 description 1
- CARMIYCQNMUOOR-UHFFFAOYSA-N methyl 3-[4-[1-(4-carbamimidoylphenyl)-2-methyl-5-oxopyrazol-3-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C(N1C)=CC(=O)N1C1=CC=C(C(N)=N)C=C1 CARMIYCQNMUOOR-UHFFFAOYSA-N 0.000 description 1
- VFBXSNNRZAGJDU-UHFFFAOYSA-N methyl 3-[4-[1-(4-carbamimidoylphenyl)-2-methylimidazol-4-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=CN(C=2C=CC(=CC=2)C(N)=N)C(C)=N1 VFBXSNNRZAGJDU-UHFFFAOYSA-N 0.000 description 1
- HGZNQQRPRPNKBO-UHFFFAOYSA-N methyl 3-[4-[1-(4-carbamimidoylphenyl)-2-phenylimidazol-4-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=CN(C=2C=CC(=CC=2)C(N)=N)C(C=2C=CC=CC=2)=N1 HGZNQQRPRPNKBO-UHFFFAOYSA-N 0.000 description 1
- VTRIWYMWPHSHMG-UHFFFAOYSA-N methyl 3-[4-[1-(4-carbamimidoylphenyl)-5-methyl-1,2,4-triazol-3-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=NN(C=2C=CC(=CC=2)C(N)=N)C(C)=N1 VTRIWYMWPHSHMG-UHFFFAOYSA-N 0.000 description 1
- NPLVTEVOMNWDAR-UHFFFAOYSA-N methyl 3-[4-[1-(4-carbamimidoylphenyl)-5-methylpyrazol-3-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=NN(C=2C=CC(=CC=2)C(N)=N)C(C)=C1 NPLVTEVOMNWDAR-UHFFFAOYSA-N 0.000 description 1
- KGPLTYPKFUTMSK-UHFFFAOYSA-N methyl 3-[4-[1-(4-carbamimidoylphenyl)pyrazol-3-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=NN(C=2C=CC(=CC=2)C(N)=N)C=C1 KGPLTYPKFUTMSK-UHFFFAOYSA-N 0.000 description 1
- XGYNMPAYCGBJLM-UHFFFAOYSA-N methyl 3-[4-[2-(4-carbamimidoyl-2-fluorophenyl)-3-oxo-1h-pyrazol-5-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=CC(=O)N(C=2C(=CC(=CC=2)C(N)=N)F)N1 XGYNMPAYCGBJLM-UHFFFAOYSA-N 0.000 description 1
- MZLFOQJAVXZOSA-UHFFFAOYSA-N methyl 3-[4-[2-(4-carbamimidoylphenyl)-1,3-thiazol-4-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=CSC(C=2C=CC(=CC=2)C(N)=N)=N1 MZLFOQJAVXZOSA-UHFFFAOYSA-N 0.000 description 1
- BKCPBRVAPUZLER-UHFFFAOYSA-N methyl 3-[4-[2-(4-carbamimidoylphenyl)-1-methylimidazol-4-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=CN(C)C(C=2C=CC(=CC=2)C(N)=N)=N1 BKCPBRVAPUZLER-UHFFFAOYSA-N 0.000 description 1
- SZVBUBFSIMWXLH-UHFFFAOYSA-N methyl 3-[4-[2-(4-carbamimidoylphenyl)-1h-imidazol-5-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=CNC(C=2C=CC(=CC=2)C(N)=N)=N1 SZVBUBFSIMWXLH-UHFFFAOYSA-N 0.000 description 1
- AKLLTDHGUFJULN-UHFFFAOYSA-N methyl 3-[4-[2-(4-carbamimidoylphenyl)-3-oxo-1h-pyrazol-5-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=CC(=O)N(C=2C=CC(=CC=2)C(N)=N)N1 AKLLTDHGUFJULN-UHFFFAOYSA-N 0.000 description 1
- XMDPGROZTHLZRF-UHFFFAOYSA-N methyl 3-[4-[3-(4-carbamimidoylphenyl)-1,2-oxazol-5-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=CC(C=2C=CC(=CC=2)C(N)=N)=NO1 XMDPGROZTHLZRF-UHFFFAOYSA-N 0.000 description 1
- CAVCLMDPFVMTFU-UHFFFAOYSA-N methyl 3-[4-[3-(4-carbamimidoylphenyl)-1h-pyrazol-5-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=CC(C=2C=CC(=CC=2)C(N)=N)=NN1 CAVCLMDPFVMTFU-UHFFFAOYSA-N 0.000 description 1
- WWEPZOABFKHVSN-UHFFFAOYSA-N methyl 3-[4-[3-(4-carbamimidoylphenyl)-2-methyl-5-oxopyrazol-1-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1N1C(=O)C=C(C=2C=CC(=CC=2)C(N)=N)N1C WWEPZOABFKHVSN-UHFFFAOYSA-N 0.000 description 1
- FCEJKRSUEBAJAD-UHFFFAOYSA-N methyl 3-[4-[3-(4-carbamimidoylphenyl)-4-carbamoyl-1h-pyrazol-5-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=C(C(N)=O)C(C=2C=CC(=CC=2)C(N)=N)=NN1 FCEJKRSUEBAJAD-UHFFFAOYSA-N 0.000 description 1
- YIOCRXIBQVZUCQ-UHFFFAOYSA-N methyl 3-[4-[3-(4-carbamimidoylphenyl)-5-methylpyrazol-1-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1N1C(C)=CC(C=2C=CC(=CC=2)C(N)=N)=N1 YIOCRXIBQVZUCQ-UHFFFAOYSA-N 0.000 description 1
- VRLNFKLZGSLNOG-UHFFFAOYSA-N methyl 3-[4-[3-(4-carbamimidoylphenyl)pyrazol-1-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1N1N=C(C=2C=CC(=CC=2)C(N)=N)C=C1 VRLNFKLZGSLNOG-UHFFFAOYSA-N 0.000 description 1
- BIYDGKSIECNSGI-UHFFFAOYSA-N methyl 3-[4-[4-(4-carbamimidoylphenyl)-1,3-oxazol-2-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=NC(C=2C=CC(=CC=2)C(N)=N)=CO1 BIYDGKSIECNSGI-UHFFFAOYSA-N 0.000 description 1
- IDBWDBZAKIHIKC-UHFFFAOYSA-N methyl 3-[4-[4-(4-carbamimidoylphenyl)-1,3-thiazol-2-yl]phenyl]propanoate;hydrochloride Chemical compound Cl.C1=CC(CCC(=O)OC)=CC=C1C1=NC(C=2C=CC(=CC=2)C(N)=N)=CS1 IDBWDBZAKIHIKC-UHFFFAOYSA-N 0.000 description 1
- KRKDXZPMUGCWAU-UHFFFAOYSA-N methyl 3-[4-[4-(4-carbamimidoylphenyl)-1-methylimidazol-2-yl]phenyl]propanoate;hydrochloride Chemical compound Cl.C1=CC(CCC(=O)OC)=CC=C1C1=NC(C=2C=CC(=CC=2)C(N)=N)=CN1C KRKDXZPMUGCWAU-UHFFFAOYSA-N 0.000 description 1
- LSIUJYJVIWOPOY-UHFFFAOYSA-N methyl 3-[4-[4-(4-carbamimidoylphenyl)-1-phenylimidazol-2-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=NC(C=2C=CC(=CC=2)C(N)=N)=CN1C1=CC=CC=C1 LSIUJYJVIWOPOY-UHFFFAOYSA-N 0.000 description 1
- VZZCNGTZJHUOJQ-UHFFFAOYSA-N methyl 3-[4-[4-(4-carbamimidoylphenyl)-5-methyl-1h-imidazol-2-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=NC(C=2C=CC(=CC=2)C(N)=N)=C(C)N1 VZZCNGTZJHUOJQ-UHFFFAOYSA-N 0.000 description 1
- HLKQNLRXWCLGMA-UHFFFAOYSA-N methyl 3-[4-[4-(4-carbamimidoylphenyl)imidazol-1-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1N1C=C(C=2C=CC(=CC=2)C(N)=N)N=C1 HLKQNLRXWCLGMA-UHFFFAOYSA-N 0.000 description 1
- WLCUXJVURVNUEX-UHFFFAOYSA-N methyl 3-[4-[4-(4-carbamimidoylphenyl)phenyl]-1,3-thiazol-2-yl]propanoate Chemical compound S1C(CCC(=O)OC)=NC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C(N)=N)=C1 WLCUXJVURVNUEX-UHFFFAOYSA-N 0.000 description 1
- WFQZPLPLIDBFMJ-UHFFFAOYSA-N methyl 3-[4-[4-(4-carbamimidoylphenyl)phenyl]-1-methylimidazol-2-yl]propanoate Chemical compound CN1C(CCC(=O)OC)=NC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C(N)=N)=C1 WFQZPLPLIDBFMJ-UHFFFAOYSA-N 0.000 description 1
- XRTSYEDSVPUQQV-UHFFFAOYSA-N methyl 3-[4-[4-(4-cyanophenyl)-1,3-thiazol-2-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=NC(C=2C=CC(=CC=2)C#N)=CS1 XRTSYEDSVPUQQV-UHFFFAOYSA-N 0.000 description 1
- HAOIGRDDOYNSSU-UHFFFAOYSA-N methyl 3-[4-[4-[4-[(e)-n'-methoxycarbonylcarbamimidoyl]phenyl]-1-methylimidazol-2-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=NC(C=2C=CC(=CC=2)C(=N)NC(=O)OC)=CN1C HAOIGRDDOYNSSU-UHFFFAOYSA-N 0.000 description 1
- OACRHJVUHRJXLW-UHFFFAOYSA-N methyl 3-[4-[5-(3-aminophenyl)-1h-imidazol-2-yl]phenyl]propanoate;hydrochloride Chemical compound Cl.C1=CC(CCC(=O)OC)=CC=C1C1=NC=C(C=2C=C(N)C=CC=2)N1 OACRHJVUHRJXLW-UHFFFAOYSA-N 0.000 description 1
- UEPYYUBPUNSNMJ-UHFFFAOYSA-N methyl 3-[4-[5-(4-carbamimidoylphenyl)-1,3-thiazol-2-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=NC=C(C=2C=CC(=CC=2)C(N)=N)S1 UEPYYUBPUNSNMJ-UHFFFAOYSA-N 0.000 description 1
- YKIUMSABOKKXRL-UHFFFAOYSA-N methyl 3-[4-[5-(4-carbamimidoylphenyl)-1-methylpyrazol-3-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=NN(C)C(C=2C=CC(=CC=2)C(N)=N)=C1 YKIUMSABOKKXRL-UHFFFAOYSA-N 0.000 description 1
- HSGZBOLTQGKAMO-UHFFFAOYSA-N methyl 3-[4-[5-(4-carbamimidoylphenyl)-1h-imidazol-2-yl]-2-(methanesulfonamido)phenyl]propanoate Chemical compound C1=C(NS(C)(=O)=O)C(CCC(=O)OC)=CC=C1C1=NC(C=2C=CC(=CC=2)C(N)=N)=CN1 HSGZBOLTQGKAMO-UHFFFAOYSA-N 0.000 description 1
- JWYCNDPVLDTCMI-UHFFFAOYSA-N methyl 3-[4-[5-(4-carbamimidoylphenyl)-1h-imidazol-2-yl]-2-hydroxyphenyl]propanoate Chemical compound C1=C(O)C(CCC(=O)OC)=CC=C1C1=NC=C(C=2C=CC(=CC=2)C(N)=N)N1 JWYCNDPVLDTCMI-UHFFFAOYSA-N 0.000 description 1
- NZRPAOAYBUVKGJ-UHFFFAOYSA-N methyl 3-[4-[5-(4-carbamimidoylphenyl)-1h-imidazol-2-yl]-2-methoxyphenyl]propanoate Chemical compound C1=C(OC)C(CCC(=O)OC)=CC=C1C1=NC=C(C=2C=CC(=CC=2)C(N)=N)N1 NZRPAOAYBUVKGJ-UHFFFAOYSA-N 0.000 description 1
- KYRQDBIFUMWWCQ-UHFFFAOYSA-N methyl 3-[4-[5-(4-carbamimidoylphenyl)-1h-imidazol-2-yl]-2-nitrophenyl]propanoate Chemical compound C1=C([N+]([O-])=O)C(CCC(=O)OC)=CC=C1C1=NC=C(C=2C=CC(=CC=2)C(N)=N)N1 KYRQDBIFUMWWCQ-UHFFFAOYSA-N 0.000 description 1
- AOBXOPHEMAPJMT-UHFFFAOYSA-N methyl 3-[4-[5-(4-carbamimidoylphenyl)-1h-imidazol-2-yl]-2-oxopyridin-1-yl]propanoate Chemical compound O=C1N(CCC(=O)OC)C=CC(C=2NC(=CN=2)C=2C=CC(=CC=2)C(N)=N)=C1 AOBXOPHEMAPJMT-UHFFFAOYSA-N 0.000 description 1
- YLPJYUDCPVBSOM-UHFFFAOYSA-N methyl 3-[4-[5-(4-carbamimidoylphenyl)-1h-imidazol-2-yl]cyclohexyl]propanoate Chemical compound C1CC(CCC(=O)OC)CCC1C1=NC(C=2C=CC(=CC=2)C(N)=N)=CN1 YLPJYUDCPVBSOM-UHFFFAOYSA-N 0.000 description 1
- PIZHQYZBJZNFBV-UHFFFAOYSA-N methyl 3-[4-[5-(4-carbamimidoylphenyl)-1h-imidazol-2-yl]phenyl]prop-2-enoate Chemical compound C1=CC(C=CC(=O)OC)=CC=C1C1=NC(C=2C=CC(=CC=2)C(N)=N)=CN1 PIZHQYZBJZNFBV-UHFFFAOYSA-N 0.000 description 1
- PZHXKCQUGOVVSQ-UHFFFAOYSA-N methyl 3-[4-[5-(4-carbamimidoylphenyl)-1h-imidazol-2-yl]phenyl]propanoate;hydrochloride Chemical compound Cl.C1=CC(CCC(=O)OC)=CC=C1C1=NC=C(C=2C=CC(=CC=2)C(N)=N)N1 PZHXKCQUGOVVSQ-UHFFFAOYSA-N 0.000 description 1
- FMJXYODHBYSVPK-UHFFFAOYSA-N methyl 3-[4-[5-(4-carbamimidoylphenyl)-2-phenylpyrazol-3-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=CC(C=2C=CC(=CC=2)C(N)=N)=NN1C1=CC=CC=C1 FMJXYODHBYSVPK-UHFFFAOYSA-N 0.000 description 1
- OJHPXGPGKRYCSH-UHFFFAOYSA-N methyl 3-[4-[5-(4-carbamimidoylphenyl)-3-oxo-1h-pyrazol-2-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1N1C(=O)C=C(C=2C=CC(=CC=2)C(N)=N)N1 OJHPXGPGKRYCSH-UHFFFAOYSA-N 0.000 description 1
- MSYQAFYLEIYAPM-UHFFFAOYSA-N methyl 3-[4-[5-(4-carbamimidoylphenyl)furan-2-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(N)=N)O1 MSYQAFYLEIYAPM-UHFFFAOYSA-N 0.000 description 1
- WJXPUZUPTZVAKG-UHFFFAOYSA-N methyl 3-[4-[5-(4-carbamimidoylphenyl)oxolan-2-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1OC(C=2C=CC(=CC=2)C(N)=N)CC1 WJXPUZUPTZVAKG-UHFFFAOYSA-N 0.000 description 1
- HJASVRNQECERTF-UHFFFAOYSA-N methyl 3-[4-[5-(4-carbamimidoylphenyl)tetrazol-2-yl]phenyl]propanoate;hydrochloride Chemical compound Cl.C1=CC(CCC(=O)OC)=CC=C1N1N=C(C=2C=CC(=CC=2)C(N)=N)N=N1 HJASVRNQECERTF-UHFFFAOYSA-N 0.000 description 1
- AEFWXMMJFUSQLE-UHFFFAOYSA-N methyl 3-[4-[5-(4-carbamimidoylphenyl)thiophen-2-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(N)=N)S1 AEFWXMMJFUSQLE-UHFFFAOYSA-N 0.000 description 1
- FGIXFUJXRLAKSP-UHFFFAOYSA-N methyl 3-[4-[5-(4-cyanophenyl)-1h-imidazol-2-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=NC(C=2C=CC(=CC=2)C#N)=CN1 FGIXFUJXRLAKSP-UHFFFAOYSA-N 0.000 description 1
- BXQQIWFVCMDVEZ-UHFFFAOYSA-N methyl 3-[4-[5-(4-cyanophenyl)tetrazol-2-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1N1N=C(C=2C=CC(=CC=2)C#N)N=N1 BXQQIWFVCMDVEZ-UHFFFAOYSA-N 0.000 description 1
- DRSQZDRUAIXBKW-UHFFFAOYSA-N methyl 3-[4-[5-[3-(diaminomethylideneamino)phenyl]-1h-imidazol-2-yl]phenyl]propanoate;hydrochloride Chemical compound Cl.C1=CC(CCC(=O)OC)=CC=C1C1=NC(C=2C=C(NC(N)=N)C=CC=2)=CN1 DRSQZDRUAIXBKW-UHFFFAOYSA-N 0.000 description 1
- RVXJAMLNAPHQKI-UHFFFAOYSA-N methyl 3-[4-[5-[4-(n'-methoxycarbonylcarbamimidoyl)phenyl]-1h-imidazol-2-yl]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1C1=NC(C=2C=CC(=CC=2)C(=N)NC(=O)OC)=CN1 RVXJAMLNAPHQKI-UHFFFAOYSA-N 0.000 description 1
- JYPAYQKQOTYKAG-UHFFFAOYSA-N methyl 3-[5-[1-(5-carbamimidoylpyridin-2-yl)piperidin-4-yl]tetrazol-2-yl]propanoate Chemical compound COC(=O)CCN1N=NC(C2CCN(CC2)C=2N=CC(=CC=2)C(N)=N)=N1 JYPAYQKQOTYKAG-UHFFFAOYSA-N 0.000 description 1
- CAHSPXNYLDUFGB-UHFFFAOYSA-N methyl 3-[5-[4-(4-carbamimidoylphenyl)phenyl]-1,3,4-oxadiazol-2-yl]propanoate Chemical compound O1C(CCC(=O)OC)=NN=C1C1=CC=C(C=2C=CC(=CC=2)C(N)=N)C=C1 CAHSPXNYLDUFGB-UHFFFAOYSA-N 0.000 description 1
- YXHRKKMNZDFQSK-UHFFFAOYSA-N methyl 3-[5-[4-(4-carbamimidoylphenyl)phenyl]-1,3,4-thiadiazol-2-yl]propanoate Chemical compound S1C(CCC(=O)OC)=NN=C1C1=CC=C(C=2C=CC(=CC=2)C(N)=N)C=C1 YXHRKKMNZDFQSK-UHFFFAOYSA-N 0.000 description 1
- QSQJMQCABJKPAS-UHFFFAOYSA-N methyl 3-[5-[4-(4-carbamimidoylphenyl)phenyl]-1,3-oxazol-2-yl]propanoate Chemical compound O1C(CCC(=O)OC)=NC=C1C1=CC=C(C=2C=CC(=CC=2)C(N)=N)C=C1 QSQJMQCABJKPAS-UHFFFAOYSA-N 0.000 description 1
- HVSYOBVZIMDLEZ-UHFFFAOYSA-N methyl 3-[5-[4-(4-carbamimidoylphenyl)phenyl]-1h-imidazol-2-yl]propanoate Chemical compound N1C(CCC(=O)OC)=NC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C(N)=N)=C1 HVSYOBVZIMDLEZ-UHFFFAOYSA-N 0.000 description 1
- FRPLAZNUFADXJC-UHFFFAOYSA-N methyl 3-[5-[4-(4-carbamimidoylphenyl)phenyl]furan-2-yl]propanoate Chemical compound O1C(CCC(=O)OC)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(N)=N)C=C1 FRPLAZNUFADXJC-UHFFFAOYSA-N 0.000 description 1
- MRWJUKKTPPGOCB-UHFFFAOYSA-N methyl 3-[5-[4-(4-carbamimidoylphenyl)phenyl]thiophen-2-yl]propanoate Chemical compound S1C(CCC(=O)OC)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(N)=N)C=C1 MRWJUKKTPPGOCB-UHFFFAOYSA-N 0.000 description 1
- CMYFSAUKCKWDHP-UHFFFAOYSA-N methyl 3-[5-[4-(4-cyanophenyl)phenyl]tetrazol-2-yl]propanoate Chemical compound COC(=O)CCN1N=NC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C#N)=N1 CMYFSAUKCKWDHP-UHFFFAOYSA-N 0.000 description 1
- LESQERXXIMHSRE-UHFFFAOYSA-N methyl 3-[5-[5-(4-carbamimidoylphenyl)-1h-imidazol-2-yl]pyridin-2-yl]propanoate Chemical compound C1=NC(CCC(=O)OC)=CC=C1C1=NC(C=2C=CC(=CC=2)C(N)=N)=CN1 LESQERXXIMHSRE-UHFFFAOYSA-N 0.000 description 1
- KQEVIFKPZOGBMZ-UHFFFAOYSA-N methyl 3-bromopropanoate Chemical compound COC(=O)CCBr KQEVIFKPZOGBMZ-UHFFFAOYSA-N 0.000 description 1
- QMLZGMGKMMBVKG-UHFFFAOYSA-N methyl 4-[1-[6-(4-carbamimidoylphenyl)pyridazin-3-yl]imidazol-4-yl]butanoate Chemical compound C1=NC(CCCC(=O)OC)=CN1C1=CC=C(C=2C=CC(=CC=2)C(N)=N)N=N1 QMLZGMGKMMBVKG-UHFFFAOYSA-N 0.000 description 1
- KKZMIDYKRKGJHG-UHFFFAOYSA-N methyl 4-cyanobenzoate Chemical compound COC(=O)C1=CC=C(C#N)C=C1 KKZMIDYKRKGJHG-UHFFFAOYSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 229940073584 methylene chloride Drugs 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- FWANZNVPCBFZLT-UHFFFAOYSA-N n-[(4-cyanophenyl)methylideneamino]benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NN=CC1=CC=C(C#N)C=C1 FWANZNVPCBFZLT-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 125000001557 phthalyl group Chemical group C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000047 product Substances 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
- 239000011833 salt mixture Substances 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229960004793 sucrose Drugs 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
- 239000000829 suppository Substances 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 230000002537 thrombolytic effect Effects 0.000 description 1
- XCAOVNOHVSHZTL-UHFFFAOYSA-N triethyl 2-(4-cyanophenyl)ethane-1,1,1-tricarboxylate Chemical compound CCOC(=O)C(C(=O)OCC)(C(=O)OCC)CC1=CC=C(C#N)C=C1 XCAOVNOHVSHZTL-UHFFFAOYSA-N 0.000 description 1
- AGZPNUZBDCYTBB-UHFFFAOYSA-N triethyl methanetricarboxylate Chemical compound CCOC(=O)C(C(=O)OCC)C(=O)OCC AGZPNUZBDCYTBB-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 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
- 210000003462 vein Anatomy 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- C07D403/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
- C07D233/64—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 substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- 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)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Molecular Biology (AREA)
- Animal Behavior & Ethology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Priority Applications (16)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4124942A DE4124942A1 (de) | 1991-07-27 | 1991-07-27 | 5-gliedrige heterocyclen, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
TW081104702A TW225537B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-07-27 | 1992-06-16 | |
EP92112568A EP0525629A3 (en) | 1991-07-27 | 1992-07-22 | 5-membered heterocycles, process for their preparation and medicaments containing them |
HU9202450A HUT61747A (en) | 1991-07-27 | 1992-07-24 | Process for producing 5-member-heterocyclic compounds and pharmaceutical compositions comprising same |
IL10263892A IL102638A (en) | 1991-07-27 | 1992-07-24 | Heterocyclic compounds their preparation and pharmaceutical compositions containing them |
FI923366A FI923366A7 (fi) | 1991-07-27 | 1992-07-24 | 5-jäseniset heterosyklit, menetelmä niiden valmistamiseksi ja näitä yhdisteitä sisältävät lääkeaineet |
ZA925573A ZA925573B (en) | 1991-07-27 | 1992-07-24 | 5-membered heterocyclic compounds processes for preparing them and pharmaceutical compositions containing these compounds |
IE242092A IE922420A1 (en) | 1991-07-27 | 1992-07-24 | Heterocyclic compounds |
NZ243713A NZ243713A (en) | 1991-07-27 | 1992-07-24 | Amidine, amino and cyano group-containing pyridazine, azole, furan, and thiophene derivatives; preparatory processes and pharmaceutical compositions |
MX9204354A MX9204354A (es) | 1991-07-27 | 1992-07-24 | Compuestos heterociclicos de 5 miembros, procedimiento para prepararlos y composiciones farmaceuticas que los contienen. |
JP4198359A JPH05221999A (ja) | 1991-07-27 | 1992-07-24 | 5員複素環化合物、それらの調製法及びこれらの化合物を含む製薬組成物 |
NO92922940A NO922940L (no) | 1991-07-27 | 1992-07-24 | Fem-leddete heterocykliske forbindelser, fremgangsmaate for deres fremstilling og legemidler inneholdende dem |
CA002074685A CA2074685A1 (en) | 1991-07-27 | 1992-07-24 | 5-membered heterocyclic compounds, processes for preparing them and pharmaceutical compositions containing these compounds |
AU20569/92A AU652064B2 (en) | 1991-07-27 | 1992-07-27 | Heterocyclic compounds |
KR1019920013494A KR930002344A (ko) | 1991-07-27 | 1992-07-27 | 5-원 헤테로사이클릭 화합물, 이의 제조방법 및 이를 함유하는 약제학적 조성물 |
US08/148,724 US5463071A (en) | 1991-07-27 | 1993-11-08 | 5-membered heterocyclic compounds, processes for preparing them and pharmaceutical compositions containing these compounds |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4124942A DE4124942A1 (de) | 1991-07-27 | 1991-07-27 | 5-gliedrige heterocyclen, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
Publications (1)
Publication Number | Publication Date |
---|---|
DE4124942A1 true DE4124942A1 (de) | 1993-01-28 |
Family
ID=6437152
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE4124942A Withdrawn DE4124942A1 (de) | 1991-07-27 | 1991-07-27 | 5-gliedrige heterocyclen, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
Country Status (16)
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DE4107857A1 (de) * | 1991-03-12 | 1992-09-17 | Thomae Gmbh Dr K | Cyclische harnstoffderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
-
1991
- 1991-07-27 DE DE4124942A patent/DE4124942A1/de not_active Withdrawn
-
1992
- 1992-06-16 TW TW081104702A patent/TW225537B/zh active
- 1992-07-22 EP EP92112568A patent/EP0525629A3/de not_active Withdrawn
- 1992-07-24 NZ NZ243713A patent/NZ243713A/en unknown
- 1992-07-24 ZA ZA925573A patent/ZA925573B/xx unknown
- 1992-07-24 JP JP4198359A patent/JPH05221999A/ja active Pending
- 1992-07-24 FI FI923366A patent/FI923366A7/fi not_active Application Discontinuation
- 1992-07-24 CA CA002074685A patent/CA2074685A1/en not_active Abandoned
- 1992-07-24 NO NO92922940A patent/NO922940L/no unknown
- 1992-07-24 MX MX9204354A patent/MX9204354A/es not_active IP Right Cessation
- 1992-07-24 HU HU9202450A patent/HUT61747A/hu unknown
- 1992-07-24 IE IE242092A patent/IE922420A1/en not_active Application Discontinuation
- 1992-07-24 IL IL10263892A patent/IL102638A/en not_active IP Right Cessation
- 1992-07-27 AU AU20569/92A patent/AU652064B2/en not_active Ceased
- 1992-07-27 KR KR1019920013494A patent/KR930002344A/ko not_active Withdrawn
-
1993
- 1993-11-08 US US08/148,724 patent/US5463071A/en not_active Expired - Fee Related
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
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US9023872B2 (en) | 2005-01-20 | 2015-05-05 | Ixchelsis Limited | Substituted triazole derivatives as oxytocin antagonists |
US9394278B2 (en) | 2005-01-20 | 2016-07-19 | Ixchelsis Limited | Substituted triazole derivatives as oxytocin antagonists |
US10150752B2 (en) | 2005-01-20 | 2018-12-11 | Ixchelsis Limited | Substituted triazole derivatives as oxytocin antagonists |
US10683293B2 (en) | 2014-08-04 | 2020-06-16 | Nuevolution A/S | Optionally fused heterocyclyl-substituted derivatives of pyrimidine useful for the treatment of inflammatory, metabolic, oncologic and autoimmune diseases |
US10689383B2 (en) | 2014-08-04 | 2020-06-23 | Nuevolution A/S | Optionally fused heterocyclyl-substituted derivatives of pyrimidine useful for the treatment of inflammatory, metabolic, oncologic and autoimmune diseases |
US11254681B2 (en) | 2014-08-04 | 2022-02-22 | Nuevolution A/S | Optionally fused heterocyclyl-substituted derivatives of pyrimidine useful for the treatment of inflammatory, metabolic, oncologic and autoimmune diseases |
US11447479B2 (en) | 2019-12-20 | 2022-09-20 | Nuevolution A/S | Compounds active towards nuclear receptors |
US11613532B2 (en) | 2020-03-31 | 2023-03-28 | Nuevolution A/S | Compounds active towards nuclear receptors |
US11780843B2 (en) | 2020-03-31 | 2023-10-10 | Nuevolution A/S | Compounds active towards nuclear receptors |
Also Published As
Publication number | Publication date |
---|---|
IL102638A0 (en) | 1993-01-14 |
TW225537B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1994-06-21 |
CA2074685A1 (en) | 1993-01-28 |
NO922940L (no) | 1993-01-28 |
NZ243713A (en) | 1995-06-27 |
NO922940D0 (no) | 1992-07-24 |
MX9204354A (es) | 1993-01-01 |
EP0525629A2 (de) | 1993-02-03 |
HU9202450D0 (en) | 1992-10-28 |
FI923366L (fi) | 1993-01-28 |
KR930002344A (ko) | 1993-02-23 |
AU652064B2 (en) | 1994-08-11 |
ZA925573B (en) | 1994-01-24 |
HUT61747A (en) | 1993-03-01 |
IL102638A (en) | 1996-10-16 |
EP0525629A3 (en) | 1997-03-19 |
IE922420A1 (en) | 1993-01-27 |
FI923366A0 (fi) | 1992-07-24 |
JPH05221999A (ja) | 1993-08-31 |
US5463071A (en) | 1995-10-31 |
FI923366A7 (fi) | 1993-01-28 |
AU2056992A (en) | 1993-01-28 |
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