JP2006528214A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2006528214A5 JP2006528214A5 JP2006529743A JP2006529743A JP2006528214A5 JP 2006528214 A5 JP2006528214 A5 JP 2006528214A5 JP 2006529743 A JP2006529743 A JP 2006529743A JP 2006529743 A JP2006529743 A JP 2006529743A JP 2006528214 A5 JP2006528214 A5 JP 2006528214A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- alkylene
- unsubstituted
- independently
- mono
- 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
Links
- -1 phenylpyridyl Chemical group 0.000 claims 179
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 78
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 77
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 69
- 125000000623 heterocyclic group Chemical group 0.000 claims 67
- 125000000217 alkyl group Chemical group 0.000 claims 64
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 53
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 52
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 46
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 44
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 42
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 42
- 229910052736 halogen Inorganic materials 0.000 claims 39
- 150000002367 halogens Chemical class 0.000 claims 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 39
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 32
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 32
- 125000003118 aryl group Chemical group 0.000 claims 25
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims 24
- 229910052731 fluorine Inorganic materials 0.000 claims 23
- 125000004076 pyridyl group Chemical group 0.000 claims 23
- 125000001544 thienyl group Chemical group 0.000 claims 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 22
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 21
- 125000002947 alkylene group Chemical group 0.000 claims 21
- 125000004122 cyclic group Chemical group 0.000 claims 21
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 20
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 19
- 125000004429 atom Chemical group 0.000 claims 19
- 239000011737 fluorine Substances 0.000 claims 19
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims 19
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 18
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 18
- 229910052801 chlorine Inorganic materials 0.000 claims 18
- 239000000460 chlorine Substances 0.000 claims 18
- 125000002950 monocyclic group Chemical group 0.000 claims 18
- 229910052757 nitrogen Inorganic materials 0.000 claims 18
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 18
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 17
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 17
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 17
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 16
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims 16
- LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 claims 16
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims 16
- ZNGWEEUXTBNKFR-UHFFFAOYSA-N 1,4-oxazepane Chemical compound C1CNCCOC1 ZNGWEEUXTBNKFR-UHFFFAOYSA-N 0.000 claims 16
- POXWDTQUDZUOGP-UHFFFAOYSA-N 1h-1,4-diazepine Chemical compound N1C=CC=NC=C1 POXWDTQUDZUOGP-UHFFFAOYSA-N 0.000 claims 16
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-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
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 16
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 16
- 150000003536 tetrazoles Chemical class 0.000 claims 16
- CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 claims 15
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims 15
- 125000001786 isothiazolyl group Chemical group 0.000 claims 15
- 125000000842 isoxazolyl group Chemical group 0.000 claims 15
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 15
- 125000000335 thiazolyl group Chemical group 0.000 claims 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 14
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims 14
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 14
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- 239000001257 hydrogen Substances 0.000 claims 14
- 125000002883 imidazolyl group Chemical group 0.000 claims 14
- 125000002971 oxazolyl group Chemical group 0.000 claims 14
- 125000003373 pyrazinyl group Chemical group 0.000 claims 14
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 14
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims 13
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 13
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims 13
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 13
- 125000003226 pyrazolyl group Chemical group 0.000 claims 13
- 125000002098 pyridazinyl 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
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 12
- ABADUMLIAZCWJD-UHFFFAOYSA-N 1,3-dioxole Chemical compound C1OC=CO1 ABADUMLIAZCWJD-UHFFFAOYSA-N 0.000 claims 11
- GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical compound C1CC=NS1 GUUULVAMQJLDSY-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
- CZSRXHJVZUBEGW-UHFFFAOYSA-N 1,2-thiazolidine Chemical compound C1CNSC1 CZSRXHJVZUBEGW-UHFFFAOYSA-N 0.000 claims 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 10
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 10
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims 10
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims 10
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 claims 10
- 125000002541 furyl group Chemical group 0.000 claims 10
- 125000005842 heteroatom Chemical group 0.000 claims 10
- 125000001041 indolyl group Chemical group 0.000 claims 10
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 10
- 229910052760 oxygen Chemical group 0.000 claims 10
- 239000001301 oxygen Chemical group 0.000 claims 10
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims 10
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims 10
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 10
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 10
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 10
- 239000011593 sulfur Substances 0.000 claims 10
- 229910052717 sulfur Inorganic materials 0.000 claims 10
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 10
- 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
- BWCDLEQTELFBAW-UHFFFAOYSA-N 3h-dioxazole Chemical compound N1OOC=C1 BWCDLEQTELFBAW-UHFFFAOYSA-N 0.000 claims 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 9
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 9
- 229910052794 bromium Inorganic materials 0.000 claims 9
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims 9
- 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims 9
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 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
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 9
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 claims 9
- 125000003831 tetrazolyl group Chemical group 0.000 claims 9
- 229930192474 thiophene Natural products 0.000 claims 9
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 8
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 8
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 claims 8
- 125000002053 thietanyl group Chemical group 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
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims 7
- YHWMFDLNZGIJSD-UHFFFAOYSA-N 2h-1,4-oxazine Chemical compound C1OC=CN=C1 YHWMFDLNZGIJSD-UHFFFAOYSA-N 0.000 claims 7
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims 7
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 7
- 125000002619 bicyclic 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
- 125000003386 piperidinyl group Chemical group 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
- 125000006565 (C4-C7) cyclic group Chemical group 0.000 claims 6
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 6
- 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
- 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
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 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
- 125000002785 azepinyl group Chemical group 0.000 claims 6
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 6
- 125000001624 naphthyl group Chemical group 0.000 claims 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 6
- XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 claims 6
- ZHKJHQBOAJQXQR-UHFFFAOYSA-N 1H-azirine Chemical compound N1C=C1 ZHKJHQBOAJQXQR-UHFFFAOYSA-N 0.000 claims 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 5
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 5
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims 5
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 5
- 125000002393 azetidinyl group Chemical group 0.000 claims 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 5
- 125000003971 isoxazolinyl group Chemical group 0.000 claims 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 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
- 238000006467 substitution reaction Methods 0.000 claims 5
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims 4
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims 4
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 claims 4
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims 4
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims 4
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims 4
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 claims 4
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims 4
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims 4
- JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 claims 4
- 125000000164 1,3-thiazinyl group Chemical group S1C(N=CC=C1)* 0.000 claims 4
- KVGZZAHHUNAVKZ-UHFFFAOYSA-N 1,4-Dioxin Chemical group O1C=COC=C1 KVGZZAHHUNAVKZ-UHFFFAOYSA-N 0.000 claims 4
- 125000005962 1,4-oxazepanyl group Chemical group 0.000 claims 4
- 125000000183 1,4-thiazinyl group Chemical group S1C(C=NC=C1)* 0.000 claims 4
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 claims 4
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 4
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims 4
- 230000029936 alkylation Effects 0.000 claims 4
- 238000005804 alkylation reaction Methods 0.000 claims 4
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims 4
- 125000005602 azabenzimidazolyl group Chemical group 0.000 claims 4
- 125000004069 aziridinyl group Chemical group 0.000 claims 4
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 4
- 125000004623 carbolinyl group Chemical group 0.000 claims 4
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims 4
- 125000004856 decahydroquinolinyl group Chemical group N1(CCCC2CCCCC12)* 0.000 claims 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 4
- 125000003838 furazanyl group Chemical group 0.000 claims 4
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 4
- 125000002636 imidazolinyl group Chemical group 0.000 claims 4
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 4
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 4
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims 4
- 125000005438 isoindazolyl group Chemical group 0.000 claims 4
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 4
- 125000005969 isothiazolinyl group Chemical group 0.000 claims 4
- 125000002757 morpholinyl group Chemical group 0.000 claims 4
- 125000004930 octahydroisoquinolinyl group Chemical group C1(NCCC2CCCC=C12)* 0.000 claims 4
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 4
- 125000000160 oxazolidinyl group Chemical group 0.000 claims 4
- 125000005968 oxazolinyl group Chemical group 0.000 claims 4
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims 4
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims 4
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims 4
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims 4
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims 4
- 125000004193 piperazinyl group Chemical group 0.000 claims 4
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 4
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims 4
- 125000005493 quinolyl group Chemical group 0.000 claims 4
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 claims 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 4
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 claims 4
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 claims 4
- 125000001984 thiazolidinyl group Chemical group 0.000 claims 4
- 125000002769 thiazolinyl group Chemical group 0.000 claims 4
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 4
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 claims 4
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims 3
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 3
- 125000005955 1H-indazolyl group Chemical group 0.000 claims 3
- XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 claims 3
- SYOANZBNGDEJFH-UHFFFAOYSA-N 2,5-dihydro-1h-triazole Chemical compound C1NNN=C1 SYOANZBNGDEJFH-UHFFFAOYSA-N 0.000 claims 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims 3
- DIXBSCZRIZDQGC-UHFFFAOYSA-N diaziridine Chemical compound C1NN1 DIXBSCZRIZDQGC-UHFFFAOYSA-N 0.000 claims 3
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 claims 3
- 125000003965 isoxazolidinyl group Chemical group 0.000 claims 3
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 3
- VSEAAEQOQBMPQF-UHFFFAOYSA-N morpholin-3-one Chemical compound O=C1COCCN1 VSEAAEQOQBMPQF-UHFFFAOYSA-N 0.000 claims 3
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims 3
- 125000002755 pyrazolinyl group Chemical group 0.000 claims 3
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims 3
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 3
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims 2
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims 2
- RFOHSZFQYMEWMH-UHFFFAOYSA-N 1,3-diazocan-2-one Chemical compound O=C1NCCCCCN1 RFOHSZFQYMEWMH-UHFFFAOYSA-N 0.000 claims 2
- CXPUAWQOXQINEX-UHFFFAOYSA-N 1,4-diazocane Chemical compound C1CCNCCNC1 CXPUAWQOXQINEX-UHFFFAOYSA-N 0.000 claims 2
- HIZVCIIORGCREW-UHFFFAOYSA-N 1,4-dioxene Chemical group C1COC=CO1 HIZVCIIORGCREW-UHFFFAOYSA-N 0.000 claims 2
- ZRQQXFMGYSOKDF-UHFFFAOYSA-N 1-propan-2-ylpiperidin-4-amine Chemical compound CC(C)N1CCC(N)CC1 ZRQQXFMGYSOKDF-UHFFFAOYSA-N 0.000 claims 2
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims 2
- VKJBICQSBBONRC-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-azocin-8-one Chemical compound O=C1NCCCCC=C1 VKJBICQSBBONRC-UHFFFAOYSA-N 0.000 claims 2
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims 2
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims 2
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical group O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 claims 2
- CJYXCQLOZNIMFP-UHFFFAOYSA-N azocan-2-one Chemical compound O=C1CCCCCCN1 CJYXCQLOZNIMFP-UHFFFAOYSA-N 0.000 claims 2
- QXNDZONIWRINJR-UHFFFAOYSA-N azocane Chemical compound C1CCCNCCC1 QXNDZONIWRINJR-UHFFFAOYSA-N 0.000 claims 2
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- WZVHPXGAWGWKTL-UHFFFAOYSA-N diazocan-3-one Chemical compound O=C1CCCCCNN1 WZVHPXGAWGWKTL-UHFFFAOYSA-N 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- OXUZCBDDXOMZAM-UHFFFAOYSA-N oxathiepane Chemical compound C1CCOSCC1 OXUZCBDDXOMZAM-UHFFFAOYSA-N 0.000 claims 2
- BTLSLHNLDQCWKS-UHFFFAOYSA-N oxocan-2-one Chemical compound O=C1CCCCCCO1 BTLSLHNLDQCWKS-UHFFFAOYSA-N 0.000 claims 2
- 125000004932 phenoxathinyl group Chemical group 0.000 claims 2
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims 2
- 125000005494 pyridonyl group Chemical group 0.000 claims 2
- 125000001422 pyrrolinyl group Chemical group 0.000 claims 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- TXLLFXVNIJXUQJ-UHFFFAOYSA-N 1,3-oxazocan-2-one Chemical compound O=C1NCCCCCO1 TXLLFXVNIJXUQJ-UHFFFAOYSA-N 0.000 claims 1
- GYZMNNQUSLUCLP-UHFFFAOYSA-N 1,4-dioxocane Chemical compound C1CCOCCOC1 GYZMNNQUSLUCLP-UHFFFAOYSA-N 0.000 claims 1
- NZBVQPIZDGSDNN-UHFFFAOYSA-N 1,4-oxazocane Chemical compound C1CCOCCNC1 NZBVQPIZDGSDNN-UHFFFAOYSA-N 0.000 claims 1
- BGJDEGLGOREKMO-UHFFFAOYSA-N 1-[(6-chloro-1-benzothiophen-2-yl)methyl]-5-(2-methoxyethoxy)-n-(1-propan-2-ylpiperidin-4-yl)pyrrolo[2,3-c]pyridine-2-carboxamide Chemical compound C=1C2=CC=C(Cl)C=C2SC=1CN1C=2C=NC(OCCOC)=CC=2C=C1C(=O)NC1CCN(C(C)C)CC1 BGJDEGLGOREKMO-UHFFFAOYSA-N 0.000 claims 1
- KYDFCAGYEWMXJD-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-5-(2-hydroxyethoxy)-n-(1-propan-2-ylpiperidin-4-yl)pyrrolo[2,3-c]pyridine-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC2=CC(OCCO)=NC=C2N1CC(=O)NC1=CC=C(Cl)C=N1 KYDFCAGYEWMXJD-UHFFFAOYSA-N 0.000 claims 1
- YREBJGUGKMXPGE-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-5-(2-methoxyethoxy)-n-(1-propan-2-ylpiperidin-4-yl)pyrrolo[2,3-c]pyridine-2-carboxamide Chemical compound C=1C=C(Cl)C=NC=1NC(=O)CN1C=2C=NC(OCCOC)=CC=2C=C1C(=O)NC1CCN(C(C)C)CC1 YREBJGUGKMXPGE-UHFFFAOYSA-N 0.000 claims 1
- PFXRYXPRYTZFLP-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrrolo[2,3-b]pyridine-5-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC2=CC(C(O)=O)=CN=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 PFXRYXPRYTZFLP-UHFFFAOYSA-N 0.000 claims 1
- JHSBJRHKOOHXDT-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrrolo[3,2-b]pyridine-5-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC2=NC(C(O)=O)=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 JHSBJRHKOOHXDT-UHFFFAOYSA-N 0.000 claims 1
- COWWBSWHWVBSOT-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(2-hydroxyethoxy)-n-(1-propan-2-ylpiperidin-4-yl)pyrrolo[2,3-c]pyridine-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC2=CC(OCCO)=NC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 COWWBSWHWVBSOT-UHFFFAOYSA-N 0.000 claims 1
- RPTIUTLKYGQUBB-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-(2-methoxyethoxy)pyrrolo[2,3-c]pyridine-2-carboxylic acid Chemical compound C1=2C=NC(OCCOC)=CC=2C=C(C(O)=O)N1CC(=NO1)C=C1C1=CC=C(Cl)S1 RPTIUTLKYGQUBB-UHFFFAOYSA-N 0.000 claims 1
- GVMZQRLWMXLXGW-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-5-oxo-4h-pyrrolo[3,2-b]pyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=2NC(=O)C=CC=2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 GVMZQRLWMXLXGW-UHFFFAOYSA-N 0.000 claims 1
- ZRKRAKQLRZOXQY-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)pyrrolo[2,3-b]pyridine-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC2=CC=CN=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 ZRKRAKQLRZOXQY-UHFFFAOYSA-N 0.000 claims 1
- QOXOXCCRKJVYCD-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)pyrrolo[3,2-b]pyridine-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC2=NC=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 QOXOXCCRKJVYCD-UHFFFAOYSA-N 0.000 claims 1
- RUCNAUQKBZWKMU-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]pyrrolo[2,3-b]pyridine-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC2=CC(C(O)=O)=CN=C2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 RUCNAUQKBZWKMU-UHFFFAOYSA-N 0.000 claims 1
- OIWIYLWZIIJNHU-UHFFFAOYSA-N 1-sulfanylpyrazole Chemical compound SN1C=CC=N1 OIWIYLWZIIJNHU-UHFFFAOYSA-N 0.000 claims 1
- JPPREFOETTUXDK-UHFFFAOYSA-N 1h-1,3-diazepine Chemical group N1C=CC=CN=C1 JPPREFOETTUXDK-UHFFFAOYSA-N 0.000 claims 1
- PTLWKRLAWHBMLM-UHFFFAOYSA-N 2,3-dihydroazete Chemical compound C1CN=C1 PTLWKRLAWHBMLM-UHFFFAOYSA-N 0.000 claims 1
- ARGCQEVBJHPOGB-UHFFFAOYSA-N 2,5-dihydrofuran Chemical compound C1OCC=C1 ARGCQEVBJHPOGB-UHFFFAOYSA-N 0.000 claims 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims 1
- ISJFZBDPJYEBEU-UHFFFAOYSA-N 2-cyclobutyl-4,5-dihydro-1,3-oxazole Chemical compound C1CCC1C1=NCCO1 ISJFZBDPJYEBEU-UHFFFAOYSA-N 0.000 claims 1
- XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 claims 1
- GSODHWYZNHBOHR-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1h-diazepine Chemical compound C1CCC=NNC1 GSODHWYZNHBOHR-UHFFFAOYSA-N 0.000 claims 1
- 125000002471 4H-quinolizinyl group Chemical group C=1(C=CCN2C=CC=CC12)* 0.000 claims 1
- BYVSMDBDTBXASR-UHFFFAOYSA-N 5,6-dihydro-4h-oxazine Chemical compound C1CON=CC1 BYVSMDBDTBXASR-UHFFFAOYSA-N 0.000 claims 1
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 1
- 239000004472 Lysine Substances 0.000 claims 1
- PNUZXRZOCDVTNP-UHFFFAOYSA-N O1COC=C1.O1COCC1 Chemical compound O1COC=C1.O1COCC1 PNUZXRZOCDVTNP-UHFFFAOYSA-N 0.000 claims 1
- UDZATVXMXQKDRB-UHFFFAOYSA-N O1NCCC1.O1N=CCC1 Chemical compound O1NCCC1.O1N=CCC1 UDZATVXMXQKDRB-UHFFFAOYSA-N 0.000 claims 1
- JUKCIOQPGPGTRA-UHFFFAOYSA-N O1SCCC1.O1SCCCCC1 Chemical compound O1SCCC1.O1SCCCCC1 JUKCIOQPGPGTRA-UHFFFAOYSA-N 0.000 claims 1
- AEKNYBWUEYNWMJ-QWOOXDRHSA-N Pramiconazole Chemical compound O=C1N(C(C)C)CCN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@@H]3O[C@](CN4N=CN=C4)(CO3)C=3C(=CC(F)=CC=3)F)=CC=2)C=C1 AEKNYBWUEYNWMJ-QWOOXDRHSA-N 0.000 claims 1
- 125000000477 aza group Chemical group 0.000 claims 1
- 125000003725 azepanyl group Chemical group 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
- 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
- VDTNNGKXZGSZIP-UHFFFAOYSA-N carbutamide Chemical group CCCCNC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 VDTNNGKXZGSZIP-UHFFFAOYSA-N 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- IFFHYPWKJWLMRH-UHFFFAOYSA-N methyl 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]pyrrolo[2,3-b]pyridine-5-carboxylate Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC2=CC(C(=O)OC)=CN=C2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 IFFHYPWKJWLMRH-UHFFFAOYSA-N 0.000 claims 1
- 125000005880 oxathiolanyl group Chemical group 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
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000005954 phenoxathiinyl group Chemical group 0.000 claims 1
- DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 claims 1
- 125000004928 piperidonyl group Chemical group 0.000 claims 1
- DDWJFSYHYPDQEL-UHFFFAOYSA-N pyrimidine;1h-pyrrole Chemical compound C=1C=CNC=1.C1=CN=CN=C1 DDWJFSYHYPDQEL-UHFFFAOYSA-N 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 claims 1
- AMIGYDGSJCJWSD-UHFFFAOYSA-N thiocane Chemical compound C1CCCSCCC1 AMIGYDGSJCJWSD-UHFFFAOYSA-N 0.000 claims 1
- WWDVSDDDSOGBOK-UHFFFAOYSA-N thiocane 1,1-dioxide Chemical compound O=S1(=O)CCCCCCC1 WWDVSDDDSOGBOK-UHFFFAOYSA-N 0.000 claims 1
- GGBSCFSQYZXHCM-UHFFFAOYSA-N thiocane 1-oxide Chemical compound O=S1CCCCCCC1 GGBSCFSQYZXHCM-UHFFFAOYSA-N 0.000 claims 1
- 150000004886 thiomorpholines Chemical class 0.000 claims 1
- 150000003852 triazoles Chemical class 0.000 claims 1
- 0 CC(NS(*)(=O)=O)=O Chemical compound CC(NS(*)(=O)=O)=O 0.000 description 27
- VVCKHHJMPOIXAQ-UHFFFAOYSA-N CC(N1)=NSC1=O Chemical compound CC(N1)=NSC1=O VVCKHHJMPOIXAQ-UHFFFAOYSA-N 0.000 description 21
- BNZBMEIFAOYZEA-UHFFFAOYSA-N CC(NC#N)=O Chemical compound CC(NC#N)=O BNZBMEIFAOYZEA-UHFFFAOYSA-N 0.000 description 16
- WGVHNCAJPFIFCR-UHFFFAOYSA-N CC(NN1)=CC1=O Chemical compound CC(NN1)=CC1=O WGVHNCAJPFIFCR-UHFFFAOYSA-N 0.000 description 16
- KGVPNLBXJKTABS-UHFFFAOYSA-N CC(ON1)=CC1=O Chemical compound CC(ON1)=CC1=O KGVPNLBXJKTABS-UHFFFAOYSA-N 0.000 description 16
- XLSXXXARCKJHOR-UHFFFAOYSA-N CC(NN1)=NC1=O Chemical compound CC(NN1)=NC1=O XLSXXXARCKJHOR-UHFFFAOYSA-N 0.000 description 15
- RKRLQDJTVWZXMM-UHFFFAOYSA-N CC(N1)=NOC1=O Chemical compound CC(N1)=NOC1=O RKRLQDJTVWZXMM-UHFFFAOYSA-N 0.000 description 14
- RAMIDNIJQHHESE-UHFFFAOYSA-N CC(N1)=NOS1=O Chemical compound CC(N1)=NOS1=O RAMIDNIJQHHESE-UHFFFAOYSA-N 0.000 description 13
- AOKKGXXYBPBKDR-UHFFFAOYSA-N CN1N=NNC1=O Chemical compound CN1N=NNC1=O AOKKGXXYBPBKDR-UHFFFAOYSA-N 0.000 description 13
- XZGLNCKSNVGDNX-UHFFFAOYSA-N Cc1nnn[nH]1 Chemical compound Cc1nnn[nH]1 XZGLNCKSNVGDNX-UHFFFAOYSA-N 0.000 description 13
- SHCJTIUGKXHXGW-UHFFFAOYSA-N CN(C(N1)=O)OC1=O Chemical compound CN(C(N1)=O)OC1=O SHCJTIUGKXHXGW-UHFFFAOYSA-N 0.000 description 12
- PYUQCOIVVOLGJK-UHFFFAOYSA-N CC(C1)=NOC1=O Chemical compound CC(C1)=NOC1=O PYUQCOIVVOLGJK-UHFFFAOYSA-N 0.000 description 9
- UHZFGTXFKBGFMX-UHFFFAOYSA-N CC(OCC(O1)=C(C)OC1=O)=O Chemical compound CC(OCC(O1)=C(C)OC1=O)=O UHZFGTXFKBGFMX-UHFFFAOYSA-N 0.000 description 9
- NNXROHRFMWHXNH-UHFFFAOYSA-N CC(O1)=NNC1=O Chemical compound CC(O1)=NNC1=O NNXROHRFMWHXNH-UHFFFAOYSA-N 0.000 description 8
- QURXGNRIOBJXHY-UHFFFAOYSA-N CC(OC(N)=O)=N Chemical compound CC(OC(N)=O)=N QURXGNRIOBJXHY-UHFFFAOYSA-N 0.000 description 8
- QMDQWTMVQROPFX-UHFFFAOYSA-N CC(NS(C(F)(F)F)(=O)=O)=O Chemical compound CC(NS(C(F)(F)F)(=O)=O)=O QMDQWTMVQROPFX-UHFFFAOYSA-N 0.000 description 7
- DLSQLKNCUGSQGW-UHFFFAOYSA-N CC(C1)=NO/C1=[O]\CC(NO)=O Chemical compound CC(C1)=NO/C1=[O]\CC(NO)=O DLSQLKNCUGSQGW-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N CN(CCC1)C1=O Chemical compound CN(CCC1)C1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- QRHZUNBGGBTEBL-UHFFFAOYSA-N CC(NS(C)(=O)=O)=O Chemical compound CC(NS(C)(=O)=O)=O QRHZUNBGGBTEBL-UHFFFAOYSA-N 0.000 description 5
- ZBVMJNCECMVCJW-UHFFFAOYSA-N CC(C1)=NOC1O Chemical compound CC(C1)=NOC1O ZBVMJNCECMVCJW-UHFFFAOYSA-N 0.000 description 2
- QURXGNRIOBJXHY-UHFFFAOYSA-O CC(OC(N)=O)=[NH2+] Chemical compound CC(OC(N)=O)=[NH2+] QURXGNRIOBJXHY-UHFFFAOYSA-O 0.000 description 2
- JVWYMTPIEVTRDL-UHFFFAOYSA-N CC(C1)=NOC1OCC(NO)=O Chemical compound CC(C1)=NOC1OCC(NO)=O JVWYMTPIEVTRDL-UHFFFAOYSA-N 0.000 description 1
- LANXHYWCYKNOOS-UHFFFAOYSA-N CC(NC(O)=O)=N Chemical compound CC(NC(O)=O)=N LANXHYWCYKNOOS-UHFFFAOYSA-N 0.000 description 1
- BVUURVAJWXFSQN-UHFFFAOYSA-N CC1=NNC2OC2O1 Chemical compound CC1=NNC2OC2O1 BVUURVAJWXFSQN-UHFFFAOYSA-N 0.000 description 1
- JHCKZGSCVJRFHY-UHFFFAOYSA-N CC1=NOCC1 Chemical compound CC1=NOCC1 JHCKZGSCVJRFHY-UHFFFAOYSA-N 0.000 description 1
- QYRJFXJUVPPOBD-UHFFFAOYSA-N CC1=NSCOCN1 Chemical compound CC1=NSCOCN1 QYRJFXJUVPPOBD-UHFFFAOYSA-N 0.000 description 1
- HOHQCLFICSFPHL-UHFFFAOYSA-N CN(C(N1)=O)OC1O Chemical compound CN(C(N1)=O)OC1O HOHQCLFICSFPHL-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03011304.7 | 2003-05-19 | ||
| EP03011304A EP1479680A1 (en) | 2003-05-19 | 2003-05-19 | Azaindole derivatives as Factor Xa inhibitors |
| PCT/EP2004/004754 WO2004101563A1 (en) | 2003-05-19 | 2004-05-05 | AZAINDOLE-DERIVATIVES AS FACTOR Xa INHIBITORS |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006528214A JP2006528214A (ja) | 2006-12-14 |
| JP2006528214A5 true JP2006528214A5 (https=) | 2007-05-17 |
| JP4733642B2 JP4733642B2 (ja) | 2011-07-27 |
Family
ID=33040951
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006529743A Expired - Fee Related JP4733642B2 (ja) | 2003-05-19 | 2004-05-05 | 第Ｘａ因子阻害剤としてのアザインドール−誘導体 |
Country Status (24)
| Country | Link |
|---|---|
| EP (2) | EP1479680A1 (https=) |
| JP (1) | JP4733642B2 (https=) |
| KR (1) | KR20060012636A (https=) |
| CN (1) | CN100347172C (https=) |
| AR (1) | AR045682A1 (https=) |
| AU (1) | AU2004238500B2 (https=) |
| BR (1) | BRPI0410429A (https=) |
| CA (1) | CA2526084A1 (https=) |
| CL (1) | CL2004001079A1 (https=) |
| CR (1) | CR8088A (https=) |
| EC (1) | ECSP056179A (https=) |
| MA (1) | MA27799A1 (https=) |
| MX (1) | MXPA05012156A (https=) |
| NO (1) | NO20055911L (https=) |
| NZ (1) | NZ543669A (https=) |
| OA (1) | OA13169A (https=) |
| PE (1) | PE20050554A1 (https=) |
| RS (1) | RS20050857A (https=) |
| RU (1) | RU2330853C2 (https=) |
| TN (1) | TNSN05296A1 (https=) |
| TW (1) | TW200510411A (https=) |
| UA (1) | UA86767C2 (https=) |
| WO (1) | WO2004101563A1 (https=) |
| ZA (1) | ZA200508150B (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2351940T3 (es) * | 2005-11-18 | 2011-02-14 | F. Hoffmann-La Roche Ag | Derivados de azaindol-2-carboxamida. |
| US8883819B2 (en) | 2011-09-01 | 2014-11-11 | Irm Llc | Bicyclic heterocycle derivatives for the treatment of pulmonary arterial hypertension |
| IN2015DN01061A (https=) | 2012-08-17 | 2015-06-26 | Bayer Cropscience Ag | |
| US9073921B2 (en) | 2013-03-01 | 2015-07-07 | Novartis Ag | Salt forms of bicyclic heterocyclic derivatives |
| CN111834531B (zh) * | 2019-04-15 | 2022-04-19 | 天津大学 | 一种有机半导体材料、制备方法及应用 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1241472B (it) | 1990-07-06 | 1994-01-17 | Olivier Linda | Dispositivo elettromeccanico per la cattura continua in particolare di topi e ratti. |
| US5788965A (en) | 1991-02-28 | 1998-08-04 | Novo Nordisk A/S | Modified factor VII |
| US5833982A (en) | 1991-02-28 | 1998-11-10 | Zymogenetics, Inc. | Modified factor VII |
| SI9520044B (sl) | 1994-04-26 | 2004-08-31 | Aventis Pharmaceuticals Inc. | Inhibitorji Xa faktorja |
| ZA964008B (en) * | 1995-06-02 | 1997-07-11 | Akzo Nobel Nv | Imidazo[1,5a]pyridine derived serine protease inhibitors |
| EP1040108B1 (en) * | 1997-12-19 | 2004-02-25 | Schering Aktiengesellschaft | Ortho-anthranilamide derivatives as anti-coagulants |
| HU227568B1 (en) * | 1997-12-24 | 2011-08-29 | Sanofi Aventis Deutschland | Indole derivatives, as inhibitors os factor xa |
| EP0987274A1 (en) | 1998-09-15 | 2000-03-22 | Hoechst Marion Roussel Deutschland GmbH | Factor VIIa Inhibitors |
| JP4241970B2 (ja) * | 1998-10-30 | 2009-03-18 | 中外製薬株式会社 | アミド結合を有するインドール誘導体、及びモノ又はジアザインドール誘導体 |
| US6632815B2 (en) * | 1999-09-17 | 2003-10-14 | Millennium Pharmaceuticals, Inc. | Inhibitors of factor Xa |
| DE60040676D1 (de) * | 1999-09-17 | 2008-12-11 | Millennium Pharm Inc | BENZAMIDE UND ÄHNLICHE INHIBITOREN VON FAKTOR Xa |
| JP2001294572A (ja) * | 2000-02-09 | 2001-10-23 | Dai Ichi Seiyaku Co Ltd | 新規スルホニル誘導体 |
| US6436965B1 (en) * | 2000-03-02 | 2002-08-20 | Merck Frosst Canada & Co. | PDE IV inhibiting amides, compositions and methods of treatment |
| WO2002000651A2 (en) * | 2000-06-27 | 2002-01-03 | Bristol-Myers Squibb Pharma Company | Factor xa inhibitors |
| CA2440803A1 (en) * | 2001-03-07 | 2002-09-12 | Pfizer Products Inc. | Modulators of chemokine receptor activity |
| US6790845B2 (en) * | 2001-04-09 | 2004-09-14 | Bristol-Myers Squibb Pharma Company | Fused heterocyclic inhibitors of factor Xa |
| EP1314733A1 (en) * | 2001-11-22 | 2003-05-28 | Aventis Pharma Deutschland GmbH | Indole-2-carboxamides as factor Xa inhibitors |
| KR100960827B1 (ko) * | 2001-12-20 | 2010-06-08 | 오에스아이 파마슈티컬스, 인코포레이티드 | 피롤로피리미딘 Ａ₂ｂ 선택성 길항 화합물, 그의 합성방법 및 용도 |
| DE10214832A1 (de) * | 2002-04-04 | 2003-10-16 | Merck Patent Gmbh | Phenylderivate 4 |
| JP2004203791A (ja) * | 2002-12-25 | 2004-07-22 | Dai Ichi Seiyaku Co Ltd | 芳香族化合物 |
| JP2004210716A (ja) * | 2002-12-27 | 2004-07-29 | Dai Ichi Seiyaku Co Ltd | ジアミド誘導体 |
| US7135469B2 (en) * | 2003-03-18 | 2006-11-14 | Bristol Myers Squibb, Co. | Linear chain substituted monocyclic and bicyclic derivatives as factor Xa inhibitors |
-
2003
- 2003-05-19 EP EP03011304A patent/EP1479680A1/en not_active Withdrawn
-
2004
- 2004-05-05 WO PCT/EP2004/004754 patent/WO2004101563A1/en not_active Ceased
- 2004-05-05 BR BRPI0410429-3A patent/BRPI0410429A/pt not_active IP Right Cessation
- 2004-05-05 AU AU2004238500A patent/AU2004238500B2/en not_active Expired - Fee Related
- 2004-05-05 CA CA002526084A patent/CA2526084A1/en not_active Abandoned
- 2004-05-05 EP EP04731161.8A patent/EP1636226B1/en not_active Expired - Lifetime
- 2004-05-05 RS YUP-2005/0857A patent/RS20050857A/sr unknown
- 2004-05-05 NZ NZ543669A patent/NZ543669A/en unknown
- 2004-05-05 JP JP2006529743A patent/JP4733642B2/ja not_active Expired - Fee Related
- 2004-05-05 MX MXPA05012156A patent/MXPA05012156A/es active IP Right Grant
- 2004-05-05 OA OA1200500323A patent/OA13169A/en unknown
- 2004-05-05 UA UAA200512133A patent/UA86767C2/ru unknown
- 2004-05-05 RU RU2005139557/04A patent/RU2330853C2/ru not_active IP Right Cessation
- 2004-05-05 KR KR1020057022131A patent/KR20060012636A/ko not_active Ceased
- 2004-05-05 CN CNB2004800139362A patent/CN100347172C/zh not_active Expired - Fee Related
- 2004-05-11 PE PE2004000481A patent/PE20050554A1/es not_active Application Discontinuation
- 2004-05-17 CL CL200401079A patent/CL2004001079A1/es unknown
- 2004-05-17 TW TW093113797A patent/TW200510411A/zh unknown
- 2004-05-17 AR ARP040101694A patent/AR045682A1/es unknown
-
2005
- 2005-10-10 ZA ZA200508150A patent/ZA200508150B/en unknown
- 2005-11-08 MA MA28588A patent/MA27799A1/fr unknown
- 2005-11-11 CR CR8088A patent/CR8088A/es not_active Application Discontinuation
- 2005-11-18 EC EC2005006179A patent/ECSP056179A/es unknown
- 2005-11-18 TN TNP2005000296A patent/TNSN05296A1/en unknown
- 2005-12-13 NO NO20055911A patent/NO20055911L/no not_active Application Discontinuation
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2010523605A5 (https=) | ||
| AU2008241091B2 (en) | Quinoline-carboxamide derivatives as P2Y12 antagonists | |
| JP2011507916A5 (https=) | ||
| CA2777632C (en) | Imidazole derivatives as casein kinase inhibitors | |
| JP2006528942A5 (https=) | ||
| JP2009509989A5 (https=) | ||
| CA2709202A1 (en) | Fused pyridine, pyrimidine and triazine compounds as cell cycle inhibitors | |
| MXPA05006200A (es) | Derivados de pirazol como inhibidores del factor xa. | |
| AU2004238499A1 (en) | Indazole-derivatives as factor Xa inhibitors | |
| JP2011512368A5 (https=) | ||
| AU2005219507A1 (en) | Pyrrole-derivatives as factor Xa inhibitors | |
| JP2006528214A5 (https=) | ||
| PT2254881E (pt) | Clorotiofeno-amidas como inibidores de factores de coagulação xa e da trombina | |
| JP2006528213A5 (https=) | ||
| CA2526082A1 (en) | Triazole-derivatives as factor xa inhibitors | |
| RU2005139555A (ru) | Производные бензимидазола в качестве ингибиторов фактора ха | |
| JP2011512367A5 (https=) | ||
| RU2005139557A (ru) | Азаиндольные производные в качестве ингибиторов фактора ха | |
| JP2008540589A5 (https=) | ||
| MXPA05005498A (es) | Derivados de imidazol como inhibidores del factor xa. | |
| JP2010532769A5 (https=) | ||
| HK1089174B (en) | Benzimidazole-derivatives as factor xa inhibitors |