JP2006528213A5 - - Google Patents
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- Publication number
- JP2006528213A5 JP2006528213A5 JP2006529739A JP2006529739A JP2006528213A5 JP 2006528213 A5 JP2006528213 A5 JP 2006528213A5 JP 2006529739 A JP2006529739 A JP 2006529739A JP 2006529739 A JP2006529739 A JP 2006529739A JP 2006528213 A5 JP2006528213 A5 JP 2006528213A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- unsubstituted
- alkylene
- mono
- chloro
- 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.)
- Granted
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- -1 phenylpyridyl Chemical group 0.000 claims 243
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 66
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 63
- 125000000623 heterocyclic group Chemical group 0.000 claims 63
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 58
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 56
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 48
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 43
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 42
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 42
- 125000000217 alkyl group Chemical group 0.000 claims 42
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 32
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 30
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 30
- 125000001544 thienyl group Chemical group 0.000 claims 30
- 125000003118 aryl group Chemical group 0.000 claims 29
- 229910052736 halogen Inorganic materials 0.000 claims 27
- 150000002367 halogens Chemical class 0.000 claims 27
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 24
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims 23
- 125000004076 pyridyl group Chemical group 0.000 claims 23
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 21
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 20
- 125000004122 cyclic group Chemical group 0.000 claims 20
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 19
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 19
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims 18
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 17
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 17
- 229910052731 fluorine Inorganic materials 0.000 claims 17
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 17
- 125000000842 isoxazolyl group Chemical group 0.000 claims 17
- CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 claims 16
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims 16
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 16
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 16
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 claims 16
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims 16
- 125000001786 isothiazolyl group Chemical group 0.000 claims 16
- 229910052757 nitrogen Inorganic materials 0.000 claims 16
- 125000003373 pyrazinyl group Chemical group 0.000 claims 16
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 16
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 16
- 150000003536 tetrazoles Chemical class 0.000 claims 16
- 125000000335 thiazolyl group Chemical group 0.000 claims 16
- LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 claims 15
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims 15
- ZNGWEEUXTBNKFR-UHFFFAOYSA-N 1,4-oxazepane Chemical compound C1CNCCOC1 ZNGWEEUXTBNKFR-UHFFFAOYSA-N 0.000 claims 15
- MSRJJSCOWHWGGX-UHFFFAOYSA-N 2h-1,3-diazepine Chemical compound C1N=CC=CC=N1 MSRJJSCOWHWGGX-UHFFFAOYSA-N 0.000 claims 15
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 15
- 125000002883 imidazolyl group Chemical group 0.000 claims 15
- 125000003226 pyrazolyl group Chemical group 0.000 claims 15
- 125000002098 pyridazinyl group Chemical group 0.000 claims 15
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 15
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims 14
- 239000011737 fluorine Substances 0.000 claims 14
- 125000002950 monocyclic group Chemical group 0.000 claims 14
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 14
- ABADUMLIAZCWJD-UHFFFAOYSA-N 1,3-dioxole Chemical compound C1OC=CO1 ABADUMLIAZCWJD-UHFFFAOYSA-N 0.000 claims 13
- POXWDTQUDZUOGP-UHFFFAOYSA-N 1h-1,4-diazepine Chemical compound N1C=CC=NC=C1 POXWDTQUDZUOGP-UHFFFAOYSA-N 0.000 claims 13
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims 13
- 125000002947 alkylene group Chemical group 0.000 claims 13
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims 13
- 239000000460 chlorine Chemical group 0.000 claims 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 239000001257 hydrogen Substances 0.000 claims 13
- 125000002971 oxazolyl group Chemical group 0.000 claims 13
- 125000000168 pyrrolyl group Chemical group 0.000 claims 13
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims 13
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims 12
- 229910052801 chlorine Inorganic materials 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 12
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 12
- GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical compound C1CC=NS1 GUUULVAMQJLDSY-UHFFFAOYSA-N 0.000 claims 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 11
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 11
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 11
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 11
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 11
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 11
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims 11
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims 11
- 125000001153 fluoro group Chemical group F* 0.000 claims 11
- 125000002541 furyl group Chemical group 0.000 claims 11
- 125000001041 indolyl group Chemical group 0.000 claims 11
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 11
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 11
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims 11
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims 11
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 11
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 11
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 11
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 11
- CZSRXHJVZUBEGW-UHFFFAOYSA-N 1,2-thiazolidine Chemical compound C1CNSC1 CZSRXHJVZUBEGW-UHFFFAOYSA-N 0.000 claims 10
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 10
- BWCDLEQTELFBAW-UHFFFAOYSA-N 3h-dioxazole Chemical compound N1OOC=C1 BWCDLEQTELFBAW-UHFFFAOYSA-N 0.000 claims 10
- 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims 10
- 125000003831 tetrazolyl group Chemical group 0.000 claims 10
- 125000002053 thietanyl group Chemical group 0.000 claims 10
- 229930192474 thiophene Natural products 0.000 claims 10
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims 9
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 claims 9
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 9
- 125000004429 atom Chemical group 0.000 claims 9
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 9
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 9
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 9
- 125000003386 piperidinyl group Chemical group 0.000 claims 9
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims 9
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims 9
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 claims 9
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 8
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 claims 8
- 125000005842 heteroatom Chemical group 0.000 claims 8
- 125000002757 morpholinyl group Chemical group 0.000 claims 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 8
- 229910052760 oxygen Chemical group 0.000 claims 8
- 239000001301 oxygen Chemical group 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 239000011593 sulfur Chemical group 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 7
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 7
- 125000002785 azepinyl group Chemical group 0.000 claims 7
- 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 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 7
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 7
- 125000004193 piperazinyl group Chemical group 0.000 claims 7
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 7
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 claims 7
- 125000001425 triazolyl group Chemical group 0.000 claims 7
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims 6
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 6
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims 6
- KGWNRZLPXLBMPS-UHFFFAOYSA-N 2h-1,3-oxazine Chemical compound C1OC=CC=N1 KGWNRZLPXLBMPS-UHFFFAOYSA-N 0.000 claims 6
- NTYABNDBNKVWOO-UHFFFAOYSA-N 2h-1,3-thiazine Chemical compound C1SC=CC=N1 NTYABNDBNKVWOO-UHFFFAOYSA-N 0.000 claims 6
- ZAISDHPZTZIFQF-UHFFFAOYSA-N 2h-1,4-thiazine Chemical compound C1SC=CN=C1 ZAISDHPZTZIFQF-UHFFFAOYSA-N 0.000 claims 6
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims 6
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 claims 6
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 6
- JZFICWYCTCCINF-UHFFFAOYSA-N Thiadiazin Chemical compound S=C1SC(C)NC(C)N1CCN1C(=S)SC(C)NC1C JZFICWYCTCCINF-UHFFFAOYSA-N 0.000 claims 6
- 150000001408 amides Chemical class 0.000 claims 6
- 125000002619 bicyclic group Chemical group 0.000 claims 6
- 229910052794 bromium Inorganic materials 0.000 claims 6
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 6
- 125000001624 naphthyl group Chemical group 0.000 claims 6
- XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 claims 6
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims 5
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims 5
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims 5
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims 5
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 5
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims 5
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 claims 5
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims 5
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims 5
- JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 claims 5
- 125000000164 1,3-thiazinyl group Chemical group S1C(N=CC=C1)* 0.000 claims 5
- 125000005962 1,4-oxazepanyl group Chemical group 0.000 claims 5
- 125000000183 1,4-thiazinyl group Chemical group S1C(C=NC=C1)* 0.000 claims 5
- 125000005955 1H-indazolyl group Chemical group 0.000 claims 5
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 5
- YHWMFDLNZGIJSD-UHFFFAOYSA-N 2h-1,4-oxazine Chemical compound C1OC=CN=C1 YHWMFDLNZGIJSD-UHFFFAOYSA-N 0.000 claims 5
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 5
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims 5
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 5
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims 5
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims 5
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims 5
- 125000002393 azetidinyl group Chemical group 0.000 claims 5
- 125000004069 aziridinyl group Chemical group 0.000 claims 5
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 5
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 5
- 125000004623 carbolinyl group Chemical group 0.000 claims 5
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims 5
- 125000004856 decahydroquinolinyl group Chemical group N1(CCCC2CCCCC12)* 0.000 claims 5
- 125000003838 furazanyl group Chemical group 0.000 claims 5
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 5
- 125000002636 imidazolinyl group Chemical group 0.000 claims 5
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 5
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims 5
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims 5
- 125000005438 isoindazolyl group Chemical group 0.000 claims 5
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims 5
- 125000003971 isoxazolinyl group Chemical group 0.000 claims 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 5
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims 5
- 125000004930 octahydroisoquinolinyl group Chemical group C1(NCCC2CCCC=C12)* 0.000 claims 5
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 5
- OOFGXDQWDNJDIS-UHFFFAOYSA-N oxathiolane Chemical compound C1COSC1 OOFGXDQWDNJDIS-UHFFFAOYSA-N 0.000 claims 5
- SJGALSBBFTYSBA-UHFFFAOYSA-N oxaziridine Chemical compound C1NO1 SJGALSBBFTYSBA-UHFFFAOYSA-N 0.000 claims 5
- 125000000160 oxazolidinyl group Chemical group 0.000 claims 5
- 125000005968 oxazolinyl group Chemical group 0.000 claims 5
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims 5
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims 5
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims 5
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims 5
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims 5
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 5
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims 5
- 125000002755 pyrazolinyl group Chemical group 0.000 claims 5
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 claims 5
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 5
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 claims 5
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 claims 5
- 125000001984 thiazolidinyl group Chemical group 0.000 claims 5
- 125000002769 thiazolinyl group Chemical group 0.000 claims 5
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- 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 1
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- 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 1
- OITDJYNYPJJPOP-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-n-[4-(2-oxopiperazin-1-yl)phenyl]benzimidazole-2-carboxamide Chemical compound N1=CC(Cl)=CC=C1NC(=O)CN1C2=CC=CC=C2N=C1C(=O)NC1=CC=C(N2C(CNCC2)=O)C=C1 OITDJYNYPJJPOP-UHFFFAOYSA-N 0.000 claims 1
- SAJHUTBIUQGDEN-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-n-[4-(2-oxopyrazin-1-yl)phenyl]benzimidazole-2-carboxamide Chemical compound N1=CC(Cl)=CC=C1NC(=O)CN1C2=CC=CC=C2N=C1C(=O)NC1=CC=C(N2C(C=NC=C2)=O)C=C1 SAJHUTBIUQGDEN-UHFFFAOYSA-N 0.000 claims 1
- FZICQKXJQSAKIP-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]benzimidazole-2-carboxylic acid Chemical compound OC(=O)C1=NC2=CC=CC=C2N1CC(=O)NC1=CC=C(Cl)C=N1 FZICQKXJQSAKIP-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- QQPMMTIDTMKOGP-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-4-(3-hydroxyazetidine-1-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)benzimidazole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=C(C(=O)N3CC(O)C3)C=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 QQPMMTIDTMKOGP-UHFFFAOYSA-N 0.000 claims 1
- JKSNJQFEXNFFFR-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-4-(3-methoxyazetidine-1-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)benzimidazole-2-carboxamide Chemical compound C1C(OC)CN1C(=O)C1=CC=CC2=C1N=C(C(=O)NC1CCN(CC1)C(C)C)N2CC1=NOC(C=2SC(Cl)=CC=2)=C1 JKSNJQFEXNFFFR-UHFFFAOYSA-N 0.000 claims 1
- XBYTVCSWMBIXTL-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-4-(4-hydroxypiperidine-1-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)benzimidazole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=C(C(=O)N3CCC(O)CC3)C=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 XBYTVCSWMBIXTL-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- WXUDBTONNGBUDV-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(3-hydroxyazetidine-1-carbonyl)-n-(1-propan-2-ylpiperidin-4-yl)benzimidazole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=CC(C(=O)N3CC(O)C3)=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 WXUDBTONNGBUDV-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- XGFZEONRZIUFGI-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)benzimidazole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=CC=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 XGFZEONRZIUFGI-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- FZRIRJREMKLKLL-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-[4-(2,4-dioxopyrimidin-1-yl)phenyl]benzimidazole-2-carboxamide Chemical compound S1C(Cl)=CC=C1C1=CC(CN2C3=CC=CC=C3N=C2C(=O)NC=2C=CC(=CC=2)N2C(NC(=O)C=C2)=O)=NO1 FZRIRJREMKLKLL-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- YHWZGFQJFXJTRO-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-[4-(2-oxopiperazin-1-yl)phenyl]benzimidazole-2-carboxamide Chemical compound S1C(Cl)=CC=C1C1=CC(CN2C3=CC=CC=C3N=C2C(=O)NC=2C=CC(=CC=2)N2C(CNCC2)=O)=NO1 YHWZGFQJFXJTRO-UHFFFAOYSA-N 0.000 claims 1
- SRSILFCRRJFGDV-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-[4-(2-oxopyrazin-1-yl)phenyl]benzimidazole-2-carboxamide Chemical compound S1C(Cl)=CC=C1C1=CC(CN2C3=CC=CC=C3N=C2C(=O)NC=2C=CC(=CC=2)N2C(C=NC=C2)=O)=NO1 SRSILFCRRJFGDV-UHFFFAOYSA-N 0.000 claims 1
- JZYDTVLYISBCTB-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-[4-(4-oxopiperidin-1-yl)phenyl]benzimidazole-2-carboxamide Chemical compound S1C(Cl)=CC=C1C1=CC(CN2C3=CC=CC=C3N=C2C(=O)NC=2C=CC(=CC=2)N2CCC(=O)CC2)=NO1 JZYDTVLYISBCTB-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- JECVXIDQIMIPQP-UHFFFAOYSA-N 1-cyclohexyloxycarbonyloxyethyl 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-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=C2N1CC(=O)NC1=CC=C(Cl)C=N1 JECVXIDQIMIPQP-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- BUFYJWWMKGFPHO-UHFFFAOYSA-N 1-cyclohexyloxycarbonyloxyethyl 3-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-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)OC(C)OC(=O)OC3CCCCC3)C=C2N1CC(=O)NC1=CC=C(Cl)C=N1 BUFYJWWMKGFPHO-UHFFFAOYSA-N 0.000 claims 1
- QMPALEKIVDLPQK-UHFFFAOYSA-N 1-ethoxycarbonyloxyethyl 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-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(=O)NC1=CC=C(Cl)C=N1 QMPALEKIVDLPQK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- OMERXXSQPSTCGL-UHFFFAOYSA-N 1-ethoxycarbonyloxyethyl 3-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-5-carboxylate Chemical compound C=1C=C(Cl)C=NC=1NC(=O)CN1C2=CC(C(=O)OC(C)OC(=O)OCC)=CC=C2N=C1C(=O)NC1CCN(C(C)C)CC1 OMERXXSQPSTCGL-UHFFFAOYSA-N 0.000 claims 1
- OIWIYLWZIIJNHU-UHFFFAOYSA-N 1-sulfanylpyrazole Chemical compound SN1C=CC=N1 OIWIYLWZIIJNHU-UHFFFAOYSA-N 0.000 claims 1
- VKJBICQSBBONRC-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-azocin-8-one Chemical compound O=C1NCCCCC=C1 VKJBICQSBBONRC-UHFFFAOYSA-N 0.000 claims 1
- ONOBXDPYDHTSBQ-UHFFFAOYSA-N 2,3,4,7-tetrahydro-1h-diazepine Chemical compound C1CC=CCNN1 ONOBXDPYDHTSBQ-UHFFFAOYSA-N 0.000 claims 1
- PTLWKRLAWHBMLM-UHFFFAOYSA-N 2,3-dihydroazete Chemical compound C1CN=C1 PTLWKRLAWHBMLM-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- HNFHOEMEVXNPFO-UHFFFAOYSA-N 2-methoxyethyl 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-4-carboxylate Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC=2C(C(=O)OCCOC)=CC=CC=2N1CC(=O)NC1=CC=C(Cl)C=N1 HNFHOEMEVXNPFO-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- ZVQYJXQMUCYMIH-UHFFFAOYSA-N 3-[[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=CC=CC(C(O)=O)=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 ZVQYJXQMUCYMIH-UHFFFAOYSA-N 0.000 claims 1
- JWRBFKWKCPLVAN-UHFFFAOYSA-N 3-[[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(C(O)=O)C=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 JWRBFKWKCPLVAN-UHFFFAOYSA-N 0.000 claims 1
- XPBPVMGKFXTAFJ-UHFFFAOYSA-N 3-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-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)=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 XPBPVMGKFXTAFJ-UHFFFAOYSA-N 0.000 claims 1
- SNZDWDLKATZKEQ-UHFFFAOYSA-N 3-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-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=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 SNZDWDLKATZKEQ-UHFFFAOYSA-N 0.000 claims 1
- SVYISQCXXAWMJM-UHFFFAOYSA-N 3-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)imidazo[4,5-b]pyridine-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=CC=CN=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 SVYISQCXXAWMJM-UHFFFAOYSA-N 0.000 claims 1
- BMSWTWHMUPZQBF-UHFFFAOYSA-N 3-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]thieno[3,4-d]imidazole-2,6-dicarboxylic acid Chemical compound OC(=O)C1=NC2=C(C(O)=O)SC=C2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 BMSWTWHMUPZQBF-UHFFFAOYSA-N 0.000 claims 1
- NGGGPXFNJGXFSE-UHFFFAOYSA-N 3-[[5-(5-chlorothiophen-2-yl)-1,3,4-thiadiazol-2-yl]methyl]-2-[(1-cyclopropylpiperidin-4-yl)carbamoyl]benzimidazole-5-carboxylic acid Chemical compound N=1N=C(C=2SC(Cl)=CC=2)SC=1CN1C2=CC(C(=O)O)=CC=C2N=C1C(=O)NC(CC1)CCN1C1CC1 NGGGPXFNJGXFSE-UHFFFAOYSA-N 0.000 claims 1
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims 1
- VUZNIZPQSKVIOP-UHFFFAOYSA-N 4-(3-hydroxyazetidine-1-carbonyl)-1-[(3-methoxyphenyl)methyl]-n-(1-propan-2-ylpiperidin-4-yl)benzimidazole-2-carboxamide Chemical compound COC1=CC=CC(CN2C3=CC=CC(=C3N=C2C(=O)NC2CCN(CC2)C(C)C)C(=O)N2CC(O)C2)=C1 VUZNIZPQSKVIOP-UHFFFAOYSA-N 0.000 claims 1
- MQTWXMJJRQOIRA-UHFFFAOYSA-N 7-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-1,3-dimethyl-2,6-dioxo-n-(1-propan-2-ylpiperidin-4-yl)purine-8-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C(N1CC2=NOC(=C2)C=2SC(Cl)=CC=2)=NC2=C1C(=O)N(C)C(=O)N2C MQTWXMJJRQOIRA-UHFFFAOYSA-N 0.000 claims 1
- NIFBNIANYCOETB-UHFFFAOYSA-N 8-methyl-n-(2-phenylethyl)-8-azabicyclo[3.2.1]octan-3-amine Chemical compound CN1C(C2)CCC1CC2NCCC1=CC=CC=C1 NIFBNIANYCOETB-UHFFFAOYSA-N 0.000 claims 1
- GBROLHHONHQRCM-UHFFFAOYSA-N N1C=NC=CC=C1.N1N=CC=CC=C1 Chemical compound N1C=NC=CC=C1.N1N=CC=CC=C1 GBROLHHONHQRCM-UHFFFAOYSA-N 0.000 claims 1
- 241000269821 Scombridae Species 0.000 claims 1
- 125000003725 azepanyl group Chemical group 0.000 claims 1
- CJYXCQLOZNIMFP-UHFFFAOYSA-N azocan-2-one Chemical compound O=C1CCCCCCN1 CJYXCQLOZNIMFP-UHFFFAOYSA-N 0.000 claims 1
- QXNDZONIWRINJR-UHFFFAOYSA-N azocane Chemical compound C1CCCNCCC1 QXNDZONIWRINJR-UHFFFAOYSA-N 0.000 claims 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 claims 1
- 239000004914 cyclooctane Substances 0.000 claims 1
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 claims 1
- 239000004913 cyclooctene Substances 0.000 claims 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- GKGOOVHEBPENJV-UHFFFAOYSA-N cyclopropylmethyl 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-2-[(1-cyclopropylpiperidin-4-yl)carbamoyl]benzimidazole-4-carboxylate Chemical compound N1=CC(Cl)=CC=C1NC(=O)CN1C2=CC=CC(C(=O)OCC3CC3)=C2N=C1C(=O)NC1CCN(C2CC2)CC1 GKGOOVHEBPENJV-UHFFFAOYSA-N 0.000 claims 1
- YRXWWXXMPMFNIQ-UHFFFAOYSA-N cyclopropylmethyl 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-4-carboxylate Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC2=C(C(=O)OCC3CC3)C=CC=C2N1CC(=O)NC1=CC=C(Cl)C=N1 YRXWWXXMPMFNIQ-UHFFFAOYSA-N 0.000 claims 1
- WZVHPXGAWGWKTL-UHFFFAOYSA-N diazocan-3-one Chemical compound O=C1CCCCCNN1 WZVHPXGAWGWKTL-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- UOHSQQPZJHQLIC-UHFFFAOYSA-N furan;1h-imidazole Chemical compound C=1C=COC=1.C1=CNC=N1 UOHSQQPZJHQLIC-UHFFFAOYSA-N 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 235000020640 mackerel Nutrition 0.000 claims 1
- PLYGXQOAGONSTM-UHFFFAOYSA-N methyl 1-[(3-methoxyphenyl)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)=CC=C2N1CC1=CC=CC(OC)=C1 PLYGXQOAGONSTM-UHFFFAOYSA-N 0.000 claims 1
- KKWZKPCBVMEYNG-UHFFFAOYSA-N methyl 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-2-[(1-cyclopropylpiperidin-4-yl)carbamoyl]benzimidazole-4-carboxylate Chemical compound C1CN(C2CC2)CCC1NC(=O)C1=NC=2C(C(=O)OC)=CC=CC=2N1CC(=O)NC1=CC=C(Cl)C=N1 KKWZKPCBVMEYNG-UHFFFAOYSA-N 0.000 claims 1
- HUXHMUUXTATWJQ-UHFFFAOYSA-N methyl 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-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)=CC=CC=2N1CC(=O)NC1=CC=C(Cl)C=N1 HUXHMUUXTATWJQ-UHFFFAOYSA-N 0.000 claims 1
- ZBZGBPFTYUQMBN-UHFFFAOYSA-N methyl 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-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)=CC=C2N1CC(=O)NC1=CC=C(Cl)C=N1 ZBZGBPFTYUQMBN-UHFFFAOYSA-N 0.000 claims 1
- ITMWBKLDVSTUHR-UHFFFAOYSA-N methyl 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-2-[[2-fluoro-4-(pyrrolidine-1-carbonyl)phenyl]carbamoyl]benzimidazole-4-carboxylate Chemical compound C=1C=C(C(=O)N2CCCC2)C=C(F)C=1NC(=O)C1=NC=2C(C(=O)OC)=CC=CC=2N1CC(=O)NC1=CC=C(Cl)C=N1 ITMWBKLDVSTUHR-UHFFFAOYSA-N 0.000 claims 1
- CGDPDGHSZPKHCR-UHFFFAOYSA-N methyl 1-[[2-(5-chlorothiophen-2-yl)-1,3-thiazol-5-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)=CC=C2N1CC(S1)=CN=C1C1=CC=C(Cl)S1 CGDPDGHSZPKHCR-UHFFFAOYSA-N 0.000 claims 1
- MQDJLSCBTJGRKB-UHFFFAOYSA-N methyl 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-cyclopropylpiperidin-4-yl)carbamoyl]benzimidazole-5-carboxylate Chemical compound C1CN(C2CC2)CCC1NC(=O)C1=NC2=CC(C(=O)OC)=CC=C2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 MQDJLSCBTJGRKB-UHFFFAOYSA-N 0.000 claims 1
- WWAGMZQRSHCKNM-UHFFFAOYSA-N methyl 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)=CC=CC=2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 WWAGMZQRSHCKNM-UHFFFAOYSA-N 0.000 claims 1
- RDTIVMPSPJZONT-UHFFFAOYSA-N methyl 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)=CC=C2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 RDTIVMPSPJZONT-UHFFFAOYSA-N 0.000 claims 1
- DCKOQKVFZHXGHJ-UHFFFAOYSA-N methyl 3-[(3-methoxyphenyl)methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-5-carboxylate Chemical compound C=1C=CC(OC)=CC=1CN1C2=CC(C(=O)OC)=CC=C2N=C1C(=O)NC1CCN(C(C)C)CC1 DCKOQKVFZHXGHJ-UHFFFAOYSA-N 0.000 claims 1
- NWCKVADLBCFKDG-UHFFFAOYSA-N methyl 3-[2-(4-chlorophenyl)ethyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-5-carboxylate Chemical compound C=1C=C(Cl)C=CC=1CCN1C2=CC(C(=O)OC)=CC=C2N=C1C(=O)NC1CCN(C(C)C)CC1 NWCKVADLBCFKDG-UHFFFAOYSA-N 0.000 claims 1
- XGKNSCVXIMCTPQ-UHFFFAOYSA-N methyl 3-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-5-carboxylate Chemical compound C=1C=C(Cl)C=NC=1NC(=O)CN1C2=CC(C(=O)OC)=CC=C2N=C1C(=O)NC1CCN(C(C)C)CC1 XGKNSCVXIMCTPQ-UHFFFAOYSA-N 0.000 claims 1
- SDNRWJHURGVZEU-UHFFFAOYSA-N methyl 3-[[2-(5-chlorothiophen-2-yl)-1,3-thiazol-5-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-5-carboxylate Chemical compound C=1N=C(C=2SC(Cl)=CC=2)SC=1CN1C2=CC(C(=O)OC)=CC=C2N=C1C(=O)NC1CCN(C(C)C)CC1 SDNRWJHURGVZEU-UHFFFAOYSA-N 0.000 claims 1
- WUCLQLJFXXYPSN-UHFFFAOYSA-N methyl 3-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-cyclopropylpiperidin-4-yl)carbamoyl]benzimidazole-5-carboxylate Chemical compound C1=C(C=2SC(Cl)=CC=2)ON=C1CN1C2=CC(C(=O)OC)=CC=C2N=C1C(=O)NC(CC1)CCN1C1CC1 WUCLQLJFXXYPSN-UHFFFAOYSA-N 0.000 claims 1
- FGSITYJTOINIBZ-UHFFFAOYSA-N methyl 3-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]-6-(2,2,2-trifluoroethoxy)thieno[3,4-d]imidazole-4-carboxylate Chemical compound C1=C(C=2SC(Cl)=CC=2)ON=C1CN1C2=C(C(=O)OC)SC(OCC(F)(F)F)=C2N=C1C(=O)NC1CCN(C(C)C)CC1 FGSITYJTOINIBZ-UHFFFAOYSA-N 0.000 claims 1
- QUMVGVQEGRHYJL-UHFFFAOYSA-N methyl 3-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]benzimidazole-4-carboxylate Chemical compound C1=C(C=2SC(Cl)=CC=2)ON=C1CN1C=2C(C(=O)OC)=CC=CC=2N=C1C(=O)NC1CCN(C(C)C)CC1 QUMVGVQEGRHYJL-UHFFFAOYSA-N 0.000 claims 1
- NBTUSWGFIAOXSE-UHFFFAOYSA-N methyl 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 C1=C(C=2SC(Cl)=CC=2)ON=C1CN1C2=CC(C(=O)OC)=CC=C2N=C1C(=O)NC1CCN(C(C)C)CC1 NBTUSWGFIAOXSE-UHFFFAOYSA-N 0.000 claims 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 1
- CZDAUXGTCCOVHY-UHFFFAOYSA-N n-(1-propan-2-ylpiperidin-4-yl)-1h-imidazole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=NC=CN1 CZDAUXGTCCOVHY-UHFFFAOYSA-N 0.000 claims 1
- AQNQGBUEVCAVML-UHFFFAOYSA-N oxazepane Chemical compound C1CCNOCC1 AQNQGBUEVCAVML-UHFFFAOYSA-N 0.000 claims 1
- 125000005961 oxazepanyl group Chemical group 0.000 claims 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims 1
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- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
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- VVGBVIKEALGJBR-UHFFFAOYSA-N thiocan-2-one Chemical compound O=C1CCCCCCS1 VVGBVIKEALGJBR-UHFFFAOYSA-N 0.000 claims 1
- AMIGYDGSJCJWSD-UHFFFAOYSA-N thiocane Chemical compound C1CCCSCCC1 AMIGYDGSJCJWSD-UHFFFAOYSA-N 0.000 claims 1
- GGBSCFSQYZXHCM-UHFFFAOYSA-N thiocane 1-oxide Chemical compound O=S1CCCCCCC1 GGBSCFSQYZXHCM-UHFFFAOYSA-N 0.000 claims 1
- XSPDXZISEYDDMJ-UHFFFAOYSA-N triazine;1,2,4-triazine Chemical compound C1=CN=NN=C1.C1=CN=NC=N1 XSPDXZISEYDDMJ-UHFFFAOYSA-N 0.000 claims 1
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| SA (1) | SA04250196B1 (enExample) |
| TN (1) | TNSN05297A1 (enExample) |
| TW (1) | TW200503696A (enExample) |
| UA (1) | UA82100C2 (enExample) |
| UY (1) | UY28324A1 (enExample) |
| WO (1) | WO2004101553A1 (enExample) |
| ZA (1) | ZA200508151B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10342570A1 (de) * | 2003-09-15 | 2005-04-14 | Bayer Healthcare Ag | Verfahren zur Herstellung von 4-(4-Aminophenyl)-3-morpholinon |
| US20060160799A1 (en) | 2004-04-23 | 2006-07-20 | Alekshun Michael N | Transcription factor modulating compounds and methods of use thereof |
| WO2008033739A2 (en) * | 2006-09-12 | 2008-03-20 | Neurogen Corporation | Benzimidazole carboxamide derivatives |
| DE102010018299A1 (de) | 2010-04-23 | 2011-10-27 | Archimica Gmbh | Verfahren zur Herstellung von 4-(4-Aminophenyl)-morpholin-3-on |
| CN105829293B (zh) * | 2013-12-20 | 2018-11-09 | 中国人民解放军军事医学科学院毒物药物研究所 | 新型哌啶氨甲酰类化合物、制备方法及其用途 |
| JOP20190024A1 (ar) | 2016-08-26 | 2019-02-19 | Gilead Sciences Inc | مركبات بيروليزين بها استبدال واستخداماتها |
| WO2019165374A1 (en) | 2018-02-26 | 2019-08-29 | Gilead Sciences, Inc. | Substituted pyrrolizine compounds as hbv replication inhibitors |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1377642A (en) * | 1971-01-14 | 1974-12-18 | Koninklijke Gist Spiritus | Penicillanic and cephalosporanic acid derivatives |
| US4269846A (en) * | 1979-10-29 | 1981-05-26 | Usv Pharmaceutical Corporation | Heterocyclic compounds useful as anti-allergy agents |
| JPH0784462B2 (ja) * | 1986-07-25 | 1995-09-13 | 日清製粉株式会社 | ベンゾイミダゾ−ル誘導体 |
| US4897401A (en) * | 1987-06-19 | 1990-01-30 | Janssen Pharmaceutical N.V. | N-(4-piperidinyl) bicyclic condensed 2-imidazolamine derivatives useful in treating allergic diseases |
| DE3828537A1 (de) * | 1988-08-23 | 1990-03-01 | Basf Ag | Neue n-substituierte benzimidazol-2-carbonsaeureanilide, deren verwendung als lichtschutzmittel, insbesondere polymere und diese anilide enthaltendes organisches material |
| JPH0324609A (ja) * | 1989-06-21 | 1991-02-01 | Mitsuba Electric Mfg Co Ltd | Ｉ／ｏ用バッファｉｃ |
| JPH03184043A (ja) * | 1989-12-14 | 1991-08-12 | Fuji Photo Film Co Ltd | ハロゲン化銀カラー写真感光材料 |
| KR100190299B1 (ko) * | 1990-07-19 | 1999-06-01 | 디르크 반테 | 신규한 옥사졸릴 유도체 |
| DE4304650A1 (de) * | 1993-02-16 | 1994-08-18 | Thomae Gmbh Dr K | Kondensierte 5-gliedrige Heterocyclen, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| SI9520096A (sl) * | 1994-09-30 | 1998-04-30 | Pfizer Inc. | Derivati 2,7-substituiranega oktahidro-1H-pirido /1,2-a/ pirazina |
| JPH08208640A (ja) * | 1995-02-06 | 1996-08-13 | Nisshin Flour Milling Co Ltd | ベンズイミダゾール誘導体およびそれを含有する心不全治療薬 |
| JPH08295667A (ja) * | 1995-04-27 | 1996-11-12 | Takeda Chem Ind Ltd | 複素環化合物、その製造法および剤 |
| JPH09124609A (ja) * | 1995-11-07 | 1997-05-13 | Nissan Chem Ind Ltd | ベンズイミダゾール誘導体 |
| JPH10182459A (ja) * | 1996-12-26 | 1998-07-07 | Otsuka Pharmaceut Co Ltd | ｃＧＭＰ分解酵素阻害剤 |
| UA62972C2 (en) * | 1997-07-03 | 2004-01-15 | Application of imidazopyrimidins and imidazopyridins for the treatment of neural disorders | |
| TR200002904T2 (tr) * | 1998-04-10 | 2001-02-21 | Japan Tobacco Inc. | Amidin bileşikleri |
| RS20050201A (sr) * | 2002-09-06 | 2007-06-04 | Janssen Pharmaceutica N.V., | Heterociklična jedinjenja |
-
2003
- 2003-05-19 EP EP03011305A patent/EP1479676A1/en not_active Withdrawn
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2004
- 2004-05-03 PE PE2004000446A patent/PE20050198A1/es not_active Application Discontinuation
- 2004-05-05 RS YUP-2005/0856A patent/RS20050856A/sr unknown
- 2004-05-05 AU AU2004238497A patent/AU2004238497B2/en not_active Expired - Fee Related
- 2004-05-05 DE DE602004028240T patent/DE602004028240D1/de not_active Expired - Lifetime
- 2004-05-05 EP EP04731162A patent/EP1636216B1/en not_active Expired - Lifetime
- 2004-05-05 CA CA002526065A patent/CA2526065A1/en not_active Abandoned
- 2004-05-05 MX MXPA05012231A patent/MXPA05012231A/es active IP Right Grant
- 2004-05-05 AT AT04731162T patent/ATE474838T1/de not_active IP Right Cessation
- 2004-05-05 OA OA1200500322A patent/OA13168A/en unknown
- 2004-05-05 KR KR1020057022122A patent/KR20060014056A/ko not_active Ceased
- 2004-05-05 CN CNA2007101491602A patent/CN101139346A/zh active Pending
- 2004-05-05 BR BRPI0410446-3A patent/BRPI0410446A/pt not_active IP Right Cessation
- 2004-05-05 CN CNB2004800139377A patent/CN100484935C/zh not_active Expired - Fee Related
- 2004-05-05 WO PCT/EP2004/004750 patent/WO2004101553A1/en not_active Ceased
- 2004-05-05 JP JP2006529739A patent/JP4658940B2/ja not_active Expired - Fee Related
- 2004-05-05 RU RU2005139555/04A patent/RU2346944C2/ru not_active IP Right Cessation
- 2004-05-05 UA UAA200512138A patent/UA82100C2/uk unknown
- 2004-05-05 NZ NZ543670A patent/NZ543670A/en unknown
- 2004-05-17 TW TW093113795A patent/TW200503696A/zh unknown
- 2004-05-17 AR ARP040101695A patent/AR045683A1/es not_active Application Discontinuation
- 2004-05-17 CL CL200401078A patent/CL2004001078A1/es unknown
- 2004-05-19 UY UY28324A patent/UY28324A1/es unknown
- 2004-05-19 PA PA20048603501A patent/PA8603501A1/es unknown
- 2004-06-30 SA SA04250196A patent/SA04250196B1/ar unknown
-
2005
- 2005-10-10 ZA ZA200508151A patent/ZA200508151B/xx unknown
- 2005-11-08 MA MA28587A patent/MA27798A1/fr unknown
- 2005-11-11 CR CR8087A patent/CR8087A/es not_active Application Discontinuation
- 2005-11-18 EC EC2005006178A patent/ECSP056178A/es unknown
- 2005-11-18 TN TNP2005000297A patent/TNSN05297A1/en unknown
- 2005-12-13 NO NO20055910A patent/NO20055910L/no not_active Application Discontinuation
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