KR20060014056A - 인자 Ｘａ 억제제로서의 벤즈이미다졸 유도체 - Google Patents

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Publication number

KR20060014056A

KR20060014056A KR1020057022122A KR20057022122A KR20060014056A KR 20060014056 A KR20060014056 A KR 20060014056A KR 1020057022122 A KR1020057022122 A KR 1020057022122A KR 20057022122 A KR20057022122 A KR 20057022122A KR 20060014056 A KR20060014056 A KR 20060014056A

Authority

KR

South Korea

Prior art keywords

alkyl

substituted

alkylene

independently

unsubstituted

Prior art date

2003-05-19

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.)

Ceased

Links

• Espacenet
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• 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title claims description 43
• 239000003112 inhibitor Substances 0.000 title abstract description 9
• 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title description 3
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 title description 2
• 239000011780 sodium chloride Substances 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 202
• 238000000034 method Methods 0.000 claims abstract description 58
• 108010074860 Factor Xa Proteins 0.000 claims abstract description 29
• 230000008569 process Effects 0.000 claims abstract description 18
• 238000011282 treatment Methods 0.000 claims abstract description 16
• 230000023555 blood coagulation Effects 0.000 claims abstract description 15
• 208000037803 restenosis Diseases 0.000 claims abstract description 11
• 208000001435 Thromboembolism Diseases 0.000 claims abstract description 7
• 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 5
• -1 cynolinyl Chemical group 0.000 claims description 613
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 147
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 147
• 125000000623 heterocyclic group Chemical class 0.000 claims description 132
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 97
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 95
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 94
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 91
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 88
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 87
• 125000003118 aryl group Chemical group 0.000 claims description 85
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 82
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 77
• 125000000217 alkyl group Chemical group 0.000 claims description 76
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 72
• 229910052757 nitrogen Inorganic materials 0.000 claims description 70
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 70
• 125000002950 monocyclic group Chemical class 0.000 claims description 68
• 229910052736 halogen Inorganic materials 0.000 claims description 67
• 150000002367 halogens Chemical class 0.000 claims description 67
• WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims description 58
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 58
• 125000001544 thienyl group Chemical group 0.000 claims description 55
• 125000004076 pyridyl group Chemical group 0.000 claims description 54
• 150000003839 salts Chemical class 0.000 claims description 51
• 125000005842 heteroatom Chemical group 0.000 claims description 50
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 46
• 125000002619 bicyclic group Chemical class 0.000 claims description 46
• 229910052717 sulfur Inorganic materials 0.000 claims description 46
• 239000011593 sulfur Chemical group 0.000 claims description 46
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 45
• 229910052760 oxygen Chemical group 0.000 claims description 45
• 239000001301 oxygen Chemical group 0.000 claims description 45
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 45
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 44
• 125000004122 cyclic group Chemical group 0.000 claims description 43
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 41
• IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims description 41
• 238000006243 chemical reaction Methods 0.000 claims description 40
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 38
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 38
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 37
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 37
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 37
• 239000000203 mixture Substances 0.000 claims description 37
• FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims description 36
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 36
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 36
• 239000002243 precursor Substances 0.000 claims description 36
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 36
• CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 claims description 35
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 35
• 229910052731 fluorine Inorganic materials 0.000 claims description 34
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 34
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 34
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 34
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 34
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 34
• 150000003536 tetrazoles Chemical class 0.000 claims description 34
• 125000000335 thiazolyl group Chemical group 0.000 claims description 34
• FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 33
• PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 33
• JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 32
• JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 32
• 125000002883 imidazolyl group Chemical group 0.000 claims description 32
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 32
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 32
• VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 32
• DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 claims description 31
• QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 30
• 239000000460 chlorine Substances 0.000 claims description 30
• 239000001257 hydrogen Substances 0.000 claims description 30
• 229910052739 hydrogen Inorganic materials 0.000 claims description 30
• 125000002971 oxazolyl group Chemical group 0.000 claims description 30
• 230000015572 biosynthetic process Effects 0.000 claims description 28
• 229910052801 chlorine Inorganic materials 0.000 claims description 28
• 239000011737 fluorine Substances 0.000 claims description 28
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 28
• OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 27
• MSRJJSCOWHWGGX-UHFFFAOYSA-N 2h-1,3-diazepine Chemical compound C1N=CC=CC=N1 MSRJJSCOWHWGGX-UHFFFAOYSA-N 0.000 claims description 27
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
• WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 27
• LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 claims description 26
• ABADUMLIAZCWJD-UHFFFAOYSA-N 1,3-dioxole Chemical compound C1OC=CO1 ABADUMLIAZCWJD-UHFFFAOYSA-N 0.000 claims description 26
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 26
• POXWDTQUDZUOGP-UHFFFAOYSA-N 1h-1,4-diazepine Chemical group N1C=CC=NC=C1 POXWDTQUDZUOGP-UHFFFAOYSA-N 0.000 claims description 25
• NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 25
• 125000002541 furyl group Chemical group 0.000 claims description 25
• CZSRXHJVZUBEGW-UHFFFAOYSA-N 1,2-thiazolidine Chemical compound C1CNSC1 CZSRXHJVZUBEGW-UHFFFAOYSA-N 0.000 claims description 24
• ZNGWEEUXTBNKFR-UHFFFAOYSA-N 1,4-oxazepane Chemical compound C1CNCCOC1 ZNGWEEUXTBNKFR-UHFFFAOYSA-N 0.000 claims description 24
• BWCDLEQTELFBAW-UHFFFAOYSA-N 3h-dioxazole Chemical compound N1OOC=C1 BWCDLEQTELFBAW-UHFFFAOYSA-N 0.000 claims description 24
• GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical compound C1CC=NS1 GUUULVAMQJLDSY-UHFFFAOYSA-N 0.000 claims description 24
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 24
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 24
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 24
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 24
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
• 125000001041 indolyl group Chemical group 0.000 claims description 24
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 24
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 24
• VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 claims description 23
• RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims description 23
• XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 23
• PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 claims description 23
• MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 23
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 23
• ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 claims description 23
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 22
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 22
• 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 22
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 22
• USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims description 22
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 22
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 22
• 125000004429 atom Chemical group 0.000 claims description 21
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 21
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 20
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 20
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 20
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 20
• DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims description 20
• 239000000126 substance Substances 0.000 claims description 20
• 229930192474 thiophene Natural products 0.000 claims description 19
• 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 18
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 18
• 239000002253 acid Substances 0.000 claims description 18
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 18
• 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 17
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 17
• 125000004193 piperazinyl group Chemical group 0.000 claims description 17
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 17
• IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 claims description 17
• WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 16
• MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims description 16
• KGWNRZLPXLBMPS-UHFFFAOYSA-N 2h-1,3-oxazine Chemical compound C1OC=CC=N1 KGWNRZLPXLBMPS-UHFFFAOYSA-N 0.000 claims description 16
• 229910052794 bromium Inorganic materials 0.000 claims description 16
• 125000001153 fluoro group Chemical group F* 0.000 claims description 16
• 125000000524 functional group Chemical group 0.000 claims description 16
• 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 16
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 16
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 15
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 15
• ZAISDHPZTZIFQF-UHFFFAOYSA-N 2h-1,4-thiazine Chemical compound C1SC=CN=C1 ZAISDHPZTZIFQF-UHFFFAOYSA-N 0.000 claims description 15
• BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 15
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 15
• JZFICWYCTCCINF-UHFFFAOYSA-N Thiadiazin Chemical compound S=C1SC(C)NC(C)N1CCN1C(=S)SC(C)NC1C JZFICWYCTCCINF-UHFFFAOYSA-N 0.000 claims description 15
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 15
• 125000002757 morpholinyl group Chemical group 0.000 claims description 15
• OOFGXDQWDNJDIS-UHFFFAOYSA-N oxathiolane Chemical compound C1COSC1 OOFGXDQWDNJDIS-UHFFFAOYSA-N 0.000 claims description 15
• 125000003386 piperidinyl group Chemical group 0.000 claims description 15
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 15
• 125000001425 triazolyl group Chemical group 0.000 claims description 15
• YHWMFDLNZGIJSD-UHFFFAOYSA-N 2h-1,4-oxazine Chemical compound C1OC=CN=C1 YHWMFDLNZGIJSD-UHFFFAOYSA-N 0.000 claims description 14
• AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 claims description 14
• 229920006395 saturated elastomer Polymers 0.000 claims description 14
• 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 13
• 125000005955 1H-indazolyl group Chemical group 0.000 claims description 13
• 125000005602 azabenzimidazolyl group Chemical group 0.000 claims description 13
• 125000002785 azepinyl group Chemical group 0.000 claims description 13
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 13
• 125000001624 naphthyl group Chemical group 0.000 claims description 13
• CZFJTEPZQBTQPQ-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]benzimidazole-2-carboxylic acid Chemical compound OC(=O)C1=NC2=CC=CC=C2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 CZFJTEPZQBTQPQ-UHFFFAOYSA-N 0.000 claims description 12
• NTYABNDBNKVWOO-UHFFFAOYSA-N 2h-1,3-thiazine Chemical compound C1SC=CC=N1 NTYABNDBNKVWOO-UHFFFAOYSA-N 0.000 claims description 12
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 12
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 12
• 125000002393 azetidinyl group Chemical group 0.000 claims description 12
• 239000002585 base Substances 0.000 claims description 12
• 239000003814 drug Substances 0.000 claims description 12
• 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 12
• 239000003960 organic solvent Substances 0.000 claims description 12
• 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims description 11
• 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims description 11
• 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 11
• 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims description 11
• 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims description 11
• 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 claims description 11
• 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 11
• 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims description 11
• JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 claims description 11
• 125000000164 1,3-thiazinyl group Chemical group S1C(N=CC=C1)* 0.000 claims description 11
• 150000004911 1,4-diazepines Chemical class 0.000 claims description 11
• 125000005962 1,4-oxazepanyl group Chemical group 0.000 claims description 11
• 125000000183 1,4-thiazinyl group Chemical group S1C(C=NC=C1)* 0.000 claims description 11
• ZHKJHQBOAJQXQR-UHFFFAOYSA-N 1H-azirine Chemical compound N1C=C1 ZHKJHQBOAJQXQR-UHFFFAOYSA-N 0.000 claims description 11
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 11
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
• 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 11
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 11
• NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 11
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 11
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• HRUDXLCXQVUPOK-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-4-(2-hydroxyethoxy)-n-(1-propan-2-ylpiperidin-4-yl)benzimidazole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=C(OCCO)C=CC=C2N1CC(=O)NC1=CC=C(Cl)C=N1 HRUDXLCXQVUPOK-UHFFFAOYSA-N 0.000 claims description 2
• SBYMGTMVNILPJE-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-4-(2-methoxyethoxy)-n-[4-(3-oxomorpholin-4-yl)phenyl]benzimidazole-2-carboxamide Chemical compound C=1C=C(N2C(COCC2)=O)C=CC=1NC(=O)C1=NC=2C(OCCOC)=CC=CC=2N1CC(=O)NC1=CC=C(Cl)C=N1 SBYMGTMVNILPJE-UHFFFAOYSA-N 0.000 claims description 2
• KYPNRPLNEPHREZ-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-4-(2-methoxyethoxymethyl)-n-(1-propan-2-ylpiperidin-4-yl)benzimidazole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC=2C(COCCOC)=CC=CC=2N1CC(=O)NC1=CC=C(Cl)C=N1 KYPNRPLNEPHREZ-UHFFFAOYSA-N 0.000 claims description 2
• OXFDZKIALNMXDU-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-4-(hydroxymethyl)-n-(1-propan-2-ylpiperidin-4-yl)benzimidazole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=C(CO)C=CC=C2N1CC(=O)NC1=CC=C(Cl)C=N1 OXFDZKIALNMXDU-UHFFFAOYSA-N 0.000 claims description 2
• SHSFYELBNQGYAC-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-4-(morpholine-4-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)benzimidazole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=C(C(=O)N3CCOCC3)C=CC=C2N1CC(=O)NC1=CC=C(Cl)C=N1 SHSFYELBNQGYAC-UHFFFAOYSA-N 0.000 claims description 2
• YCMIKXOUACICIK-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-5-(2-hydroxyethylsulfonyl)-n-(1-propan-2-ylpiperidin-4-yl)benzimidazole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=CC(S(=O)(=O)CCO)=CC=C2N1CC(=O)NC1=CC=C(Cl)C=N1 YCMIKXOUACICIK-UHFFFAOYSA-N 0.000 claims description 2
• ALNMAWGOKNHARU-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-6-(2-hydroxyethylsulfonyl)-n-(1-propan-2-ylpiperidin-4-yl)benzimidazole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=CC=C(S(=O)(=O)CCO)C=C2N1CC(=O)NC1=CC=C(Cl)C=N1 ALNMAWGOKNHARU-UHFFFAOYSA-N 0.000 claims description 2
• CAUXGUYOENLZLR-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-n-(1-propan-2-ylpiperidin-4-yl)benzimidazole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=CC=CC=C2N1CC(=O)NC1=CC=C(Cl)C=N1 CAUXGUYOENLZLR-UHFFFAOYSA-N 0.000 claims description 2
• RCEOVQCHHBTMGR-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-n-[4-(1,1-dioxo-1,4-thiazinan-4-yl)phenyl]benzimidazole-2-carboxamide Chemical compound N1=CC(Cl)=CC=C1NC(=O)CN1C2=CC=CC=C2N=C1C(=O)NC1=CC=C(N2CCS(=O)(=O)CC2)C=C1 RCEOVQCHHBTMGR-UHFFFAOYSA-N 0.000 claims description 2
• XQWUKSUHEOQEJF-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-n-[4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]benzimidazole-2-carboxamide Chemical compound N1=CC(Cl)=CC=C1NC(=O)CN1C2=CC=CC=C2N=C1C(=O)NC1=CC=C(N2C(OCC2)=O)C=C1 XQWUKSUHEOQEJF-UHFFFAOYSA-N 0.000 claims description 2
• PTBORCNMYIGGQP-UHFFFAOYSA-N 1-[[2-(5-chlorothiophen-2-yl)-1,3-thiazol-5-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-5-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=CC(C(O)=O)=CC=C2N1CC1=CN=C(C=2SC(Cl)=CC=2)S1 PTBORCNMYIGGQP-UHFFFAOYSA-N 0.000 claims description 2
• SGAACRXHZFFCTC-UHFFFAOYSA-N 1-[[3-(5-chlorothiophen-2-yl)-1,2-oxazol-5-yl]methyl]-2-[(1-cyclopropylpiperidin-4-yl)carbamoyl]benzimidazole-5-carboxylic acid Chemical compound C1CN(C2CC2)CCC1NC(=O)C1=NC2=CC(C(=O)O)=CC=C2N1CC(ON=1)=CC=1C1=CC=C(Cl)S1 SGAACRXHZFFCTC-UHFFFAOYSA-N 0.000 claims description 2
• YAXPKVALIBHNPL-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-cyclopropylpiperidin-4-yl)carbamoyl]-7-methylbenzimidazole-5-carboxylic acid Chemical compound C1=C(C=2SC(Cl)=CC=2)ON=C1CN1C=2C(C)=CC(C(O)=O)=CC=2N=C1C(=O)NC(CC1)CCN1C1CC1 YAXPKVALIBHNPL-UHFFFAOYSA-N 0.000 claims description 2
• YLVDHNSFFZKYPB-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-cyclopropylpiperidin-4-yl)carbamoyl]benzimidazole-4-carboxylic acid Chemical compound C1CN(C2CC2)CCC1NC(=O)C1=NC=2C(C(=O)O)=CC=CC=2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 YLVDHNSFFZKYPB-UHFFFAOYSA-N 0.000 claims description 2
• PQDRCVHHJPMGKO-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-cyclopropylpiperidin-4-yl)carbamoyl]benzimidazole-5-carboxylic acid Chemical compound C1CN(C2CC2)CCC1NC(=O)C1=NC2=CC(C(=O)O)=CC=C2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 PQDRCVHHJPMGKO-UHFFFAOYSA-N 0.000 claims description 2
• LGGPKSYWUCRBFX-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]-5-(2,2,2-trifluoroethoxy)benzimidazole-4-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=C(C(O)=O)C(OCC(F)(F)F)=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 LGGPKSYWUCRBFX-UHFFFAOYSA-N 0.000 claims description 2
• OKUVXXZKJBEARR-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-4-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=C(C(O)=O)C=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 OKUVXXZKJBEARR-UHFFFAOYSA-N 0.000 claims description 2
• IMFFMUPJZJSIAL-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-5-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=CC(C(O)=O)=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 IMFFMUPJZJSIAL-UHFFFAOYSA-N 0.000 claims description 2
• RZZFNZGQZVFPMS-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(2-hydroxyethylsulfonyl)-n-(1-propan-2-ylpiperidin-4-yl)benzimidazole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=CC(S(=O)(=O)CCO)=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 RZZFNZGQZVFPMS-UHFFFAOYSA-N 0.000 claims description 2
• VIHISSHFIYSNCS-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-fluoro-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-4-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=C(C(O)=O)C(F)=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 VIHISSHFIYSNCS-UHFFFAOYSA-N 0.000 claims description 2
• GKIQAGSKHLTNDY-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-6-(2-hydroxyethylsulfonyl)-n-(1-propan-2-ylpiperidin-4-yl)benzimidazole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=CC=C(S(=O)(=O)CCO)C=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 GKIQAGSKHLTNDY-UHFFFAOYSA-N 0.000 claims description 2
• SIHSPDKPDZJEHR-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-pyrimidin-4-ylpiperidin-4-yl)benzimidazole-2-carboxamide Chemical compound S1C(Cl)=CC=C1C1=CC(CN2C3=CC=CC=C3N=C2C(=O)NC2CCN(CC2)C=2N=CN=CC=2)=NO1 SIHSPDKPDZJEHR-UHFFFAOYSA-N 0.000 claims description 2
• KTDABUFXFIPFOK-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-[4-(2-oxo-1,3-oxazolidin-3-yl)phenyl]benzimidazole-2-carboxamide Chemical compound S1C(Cl)=CC=C1C1=CC(CN2C3=CC=CC=C3N=C2C(=O)NC=2C=CC(=CC=2)N2C(OCC2)=O)=NO1 KTDABUFXFIPFOK-UHFFFAOYSA-N 0.000 claims description 2
• AWAFQKCSARQPCL-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]benzimidazole-2,5-dicarboxylic acid Chemical compound OC(=O)C1=NC2=CC(C(O)=O)=CC=C2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 AWAFQKCSARQPCL-UHFFFAOYSA-N 0.000 claims description 2
• ADTRLMBWHNHJAQ-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,3,4-thiadiazol-2-yl]methyl]-2-[(1-cyclopropylpiperidin-4-yl)carbamoyl]benzimidazole-5-carboxylic acid Chemical compound C1CN(C2CC2)CCC1NC(=O)C1=NC2=CC(C(=O)O)=CC=C2N1CC(S1)=NN=C1C1=CC=C(Cl)S1 ADTRLMBWHNHJAQ-UHFFFAOYSA-N 0.000 claims description 2
• GMWUQUUXTJALTM-UHFFFAOYSA-N 1-cyclohexyloxycarbonyloxyethyl 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-4-carboxylate Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=C(C(=O)OC(C)OC(=O)OC3CCCCC3)C=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 GMWUQUUXTJALTM-UHFFFAOYSA-N 0.000 claims description 2
• IYQORANSUXUJPK-UHFFFAOYSA-N 1-cyclohexyloxycarbonyloxyethyl 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-5-carboxylate Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=CC(C(=O)OC(C)OC(=O)OC3CCCCC3)=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 IYQORANSUXUJPK-UHFFFAOYSA-N 0.000 claims description 2
• VQUJOKUVUBVTIG-UHFFFAOYSA-N 1-ethoxycarbonyloxyethyl 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-4-carboxylate Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC=2C(C(=O)OC(C)OC(=O)OCC)=CC=CC=2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 VQUJOKUVUBVTIG-UHFFFAOYSA-N 0.000 claims description 2
• NWTOSLQPJJYUHS-UHFFFAOYSA-N 1-ethoxycarbonyloxyethyl 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-5-carboxylate Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=CC(C(=O)OC(C)OC(=O)OCC)=CC=C2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 NWTOSLQPJJYUHS-UHFFFAOYSA-N 0.000 claims description 2
• OIWIYLWZIIJNHU-UHFFFAOYSA-N 1-sulfanylpyrazole Chemical compound SN1C=CC=N1 OIWIYLWZIIJNHU-UHFFFAOYSA-N 0.000 claims description 2
• POWXDMSNMAUQAD-UHFFFAOYSA-N 2-[1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-4-carbonyl]oxyacetic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=C(C(=O)OCC(O)=O)C=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 POWXDMSNMAUQAD-UHFFFAOYSA-N 0.000 claims description 2
• ZQGHAFXNATWNHY-UHFFFAOYSA-N 2-[1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-5-carbonyl]oxyacetic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=CC(C(=O)OCC(O)=O)=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 ZQGHAFXNATWNHY-UHFFFAOYSA-N 0.000 claims description 2
• HBCVCIQWVHKFPM-UHFFFAOYSA-N 2-hydroxyethyl 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-4-carboxylate Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=C(C(=O)OCCO)C=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 HBCVCIQWVHKFPM-UHFFFAOYSA-N 0.000 claims description 2
• WTKOVCWQLFBVPI-UHFFFAOYSA-N 2-hydroxyethyl 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-5-carboxylate Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=CC(C(=O)OCCO)=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 WTKOVCWQLFBVPI-UHFFFAOYSA-N 0.000 claims description 2
• NONCMHXGFBXCSL-UHFFFAOYSA-N 2-hydroxyethyl 3-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-5-carboxylate Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=CC=C(C(=O)OCCO)C=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 NONCMHXGFBXCSL-UHFFFAOYSA-N 0.000 claims description 2
• RLLKIPVOALIVME-UHFFFAOYSA-N 3-[(3-methoxyphenyl)methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-4-carboxylic acid Chemical compound COC1=CC=CC(CN2C3=C(C(O)=O)C=CC=C3N=C2C(=O)NC2CCN(CC2)C(C)C)=C1 RLLKIPVOALIVME-UHFFFAOYSA-N 0.000 claims description 2
• VUIMQNRGJHYQRY-UHFFFAOYSA-N 3-[(5-chloro-1-benzothiophen-2-yl)methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-4-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=CC=CC(C(O)=O)=C2N1CC1=CC2=CC(Cl)=CC=C2S1 VUIMQNRGJHYQRY-UHFFFAOYSA-N 0.000 claims description 2
• VCIMHDXLNJYZIW-UHFFFAOYSA-N 3-[2-(4-chlorophenyl)ethyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-4-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=CC=CC(C(O)=O)=C2N1CCC1=CC=C(Cl)C=C1 VCIMHDXLNJYZIW-UHFFFAOYSA-N 0.000 claims description 2
• NVKJJNQVQGPXLK-UHFFFAOYSA-N 3-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-5-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=CC=C(C(O)=O)C=C2N1CC(=O)NC1=CC=C(Cl)C=N1 NVKJJNQVQGPXLK-UHFFFAOYSA-N 0.000 claims description 2
• WLSXXQHRDUZVRE-UHFFFAOYSA-N 3-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]thieno[3,4-d]imidazole-4-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=CSC(C(O)=O)=C2N1CC(=O)NC1=CC=C(Cl)C=N1 WLSXXQHRDUZVRE-UHFFFAOYSA-N 0.000 claims description 2
• SAOQNEOWEHJDPE-UHFFFAOYSA-N 3-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]thieno[3,4-d]imidazole-6-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=C(C(O)=O)SC=C2N1CC(=O)NC1=CC=C(Cl)C=N1 SAOQNEOWEHJDPE-UHFFFAOYSA-N 0.000 claims description 2
• JWSARPZNUXBSJP-UHFFFAOYSA-N 3-[[2-(5-chlorothiophen-2-yl)-1,3-thiazol-5-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-5-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=CC=C(C(O)=O)C=C2N1CC1=CN=C(C=2SC(Cl)=CC=2)S1 JWSARPZNUXBSJP-UHFFFAOYSA-N 0.000 claims description 2
• UWZJASBOGIDCPX-UHFFFAOYSA-N 3-[[3-(5-chlorothiophen-2-yl)-1,2-oxazol-5-yl]methyl]-2-[(1-cyclopropylpiperidin-4-yl)carbamoyl]benzimidazole-5-carboxylic acid Chemical compound C=1C(C=2SC(Cl)=CC=2)=NOC=1CN1C2=CC(C(=O)O)=CC=C2N=C1C(=O)NC(CC1)CCN1C1CC1 UWZJASBOGIDCPX-UHFFFAOYSA-N 0.000 claims description 2
• OWMJNRDDIWQBQB-UHFFFAOYSA-N 3-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-cyclopropylpiperidin-4-yl)carbamoyl]-7-methylbenzimidazole-5-carboxylic acid Chemical compound C1CN(C2CC2)CCC1NC(=O)C1=NC=2C(C)=CC(C(O)=O)=CC=2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 OWMJNRDDIWQBQB-UHFFFAOYSA-N 0.000 claims description 2
• RPCCVIYJCAANPN-UHFFFAOYSA-N 3-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-cyclopropylpiperidin-4-yl)carbamoyl]benzimidazole-4-carboxylic acid Chemical compound C1=C(C=2SC(Cl)=CC=2)ON=C1CN1C=2C(C(=O)O)=CC=CC=2N=C1C(=O)NC(CC1)CCN1C1CC1 RPCCVIYJCAANPN-UHFFFAOYSA-N 0.000 claims description 2
• OQKCDMANESWBJR-UHFFFAOYSA-N 3-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-cyclopropylpiperidin-4-yl)carbamoyl]benzimidazole-5-carboxylic acid Chemical compound C1=C(C=2SC(Cl)=CC=2)ON=C1CN1C2=CC(C(=O)O)=CC=C2N=C1C(=O)NC(CC1)CCN1C1CC1 OQKCDMANESWBJR-UHFFFAOYSA-N 0.000 claims description 2
• JZVCZVTVKDLABR-UHFFFAOYSA-N 3-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-cyclopropylpiperidin-4-yl)carbamoyl]thieno[3,4-d]imidazole-4-carboxylic acid Chemical compound C1=C(C=2SC(Cl)=CC=2)ON=C1CN1C2=C(C(=O)O)SC=C2N=C1C(=O)NC(CC1)CCN1C1CC1 JZVCZVTVKDLABR-UHFFFAOYSA-N 0.000 claims description 2
• ARQAABBCGAVNQJ-UHFFFAOYSA-N 3-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-cyclopropylpiperidin-4-yl)carbamoyl]thieno[3,4-d]imidazole-6-carboxylic acid Chemical compound C1CN(C2CC2)CCC1NC(=O)C1=NC2=C(C(=O)O)SC=C2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 ARQAABBCGAVNQJ-UHFFFAOYSA-N 0.000 claims description 2
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