JP2006528942A5 - - Google Patents
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- Publication number
- JP2006528942A5 JP2006528942A5 JP2006529742A JP2006529742A JP2006528942A5 JP 2006528942 A5 JP2006528942 A5 JP 2006528942A5 JP 2006529742 A JP2006529742 A JP 2006529742A JP 2006529742 A JP2006529742 A JP 2006529742A JP 2006528942 A5 JP2006528942 A5 JP 2006528942A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- chloro
- indazole
- alkylene
- unsubstituted
- 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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- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 39
- -1 phenylpyridyl Chemical group 0.000 claims 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 29
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 27
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 24
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 23
- 125000000623 heterocyclic group Chemical group 0.000 claims 23
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 22
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 22
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 20
- 125000000217 alkyl group Chemical group 0.000 claims 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 16
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 14
- VICTXSNYQBQMIN-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]indazole-3,5-dicarboxylic acid Chemical compound C12=CC=C(C(O)=O)C=C2C(C(=O)O)=NN1CC(=NO1)C=C1C1=CC=C(Cl)S1 VICTXSNYQBQMIN-UHFFFAOYSA-N 0.000 claims 13
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 12
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 12
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 10
- 229910052731 fluorine Inorganic materials 0.000 claims 10
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 9
- 125000004076 pyridyl group Chemical group 0.000 claims 9
- LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 claims 8
- ZNGWEEUXTBNKFR-UHFFFAOYSA-N 1,4-oxazepane Chemical compound C1CNCCOC1 ZNGWEEUXTBNKFR-UHFFFAOYSA-N 0.000 claims 8
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims 8
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 8
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 8
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 8
- 229910052801 chlorine Inorganic materials 0.000 claims 8
- 239000000460 chlorine Substances 0.000 claims 8
- 125000004122 cyclic group Chemical group 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 150000002367 halogens Chemical class 0.000 claims 8
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 8
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims 8
- 150000003536 tetrazoles Chemical class 0.000 claims 8
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 7
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims 7
- CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 claims 7
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims 7
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims 7
- MSRJJSCOWHWGGX-UHFFFAOYSA-N 2h-1,3-diazepine Chemical compound C1N=CC=CC=N1 MSRJJSCOWHWGGX-UHFFFAOYSA-N 0.000 claims 7
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 7
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 claims 7
- 125000002947 alkylene group Chemical group 0.000 claims 7
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims 7
- 239000011737 fluorine Substances 0.000 claims 7
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 7
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 7
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims 6
- POXWDTQUDZUOGP-UHFFFAOYSA-N 1h-1,4-diazepine Chemical compound N1C=CC=NC=C1 POXWDTQUDZUOGP-UHFFFAOYSA-N 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 125000002883 imidazolyl group Chemical group 0.000 claims 6
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 6
- 125000001544 thienyl group Chemical group 0.000 claims 6
- 229930192474 thiophene Natural products 0.000 claims 6
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 5
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 5
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 5
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims 5
- 125000002098 pyridazinyl group Chemical group 0.000 claims 5
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims 5
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 5
- 125000000335 thiazolyl group Chemical group 0.000 claims 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 4
- 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 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 4
- 125000001786 isothiazolyl group Chemical group 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 125000002971 oxazolyl group Chemical group 0.000 claims 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims 4
- 125000001425 triazolyl group Chemical group 0.000 claims 4
- CZSRXHJVZUBEGW-UHFFFAOYSA-N 1,2-thiazolidine Chemical compound C1CNSC1 CZSRXHJVZUBEGW-UHFFFAOYSA-N 0.000 claims 3
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 3
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 3
- GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical compound C1CC=NS1 GUUULVAMQJLDSY-UHFFFAOYSA-N 0.000 claims 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 3
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000002541 furyl group Chemical group 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 125000006565 (C4-C7) cyclic group Chemical group 0.000 claims 2
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims 2
- ABADUMLIAZCWJD-UHFFFAOYSA-N 1,3-dioxole Chemical compound C1OC=CO1 ABADUMLIAZCWJD-UHFFFAOYSA-N 0.000 claims 2
- AXVZCWHJVSLHST-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]indazole-3-carboxylic acid Chemical compound C12=CC=CC=C2C(C(=O)O)=NN1CC(=NO1)C=C1C1=CC=C(Cl)S1 AXVZCWHJVSLHST-UHFFFAOYSA-N 0.000 claims 2
- ZHKJHQBOAJQXQR-UHFFFAOYSA-N 1H-azirine Chemical compound N1C=C1 ZHKJHQBOAJQXQR-UHFFFAOYSA-N 0.000 claims 2
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims 2
- KGWNRZLPXLBMPS-UHFFFAOYSA-N 2h-1,3-oxazine Chemical compound C1OC=CC=N1 KGWNRZLPXLBMPS-UHFFFAOYSA-N 0.000 claims 2
- NTYABNDBNKVWOO-UHFFFAOYSA-N 2h-1,3-thiazine Chemical compound C1SC=CC=N1 NTYABNDBNKVWOO-UHFFFAOYSA-N 0.000 claims 2
- YHWMFDLNZGIJSD-UHFFFAOYSA-N 2h-1,4-oxazine Chemical compound C1OC=CN=C1 YHWMFDLNZGIJSD-UHFFFAOYSA-N 0.000 claims 2
- ZAISDHPZTZIFQF-UHFFFAOYSA-N 2h-1,4-thiazine Chemical compound C1SC=CN=C1 ZAISDHPZTZIFQF-UHFFFAOYSA-N 0.000 claims 2
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims 2
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 claims 2
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims 2
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims 2
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims 2
- JZFICWYCTCCINF-UHFFFAOYSA-N Thiadiazin Chemical compound S=C1SC(C)NC(C)N1CCN1C(=S)SC(C)NC1C JZFICWYCTCCINF-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims 2
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 claims 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims 2
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 2
- 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 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- VSEAAEQOQBMPQF-UHFFFAOYSA-N morpholin-3-one Chemical compound O=C1COCCN1 VSEAAEQOQBMPQF-UHFFFAOYSA-N 0.000 claims 2
- OOFGXDQWDNJDIS-UHFFFAOYSA-N oxathiolane Chemical compound C1COSC1 OOFGXDQWDNJDIS-UHFFFAOYSA-N 0.000 claims 2
- SJGALSBBFTYSBA-UHFFFAOYSA-N oxaziridine Chemical compound C1NO1 SJGALSBBFTYSBA-UHFFFAOYSA-N 0.000 claims 2
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims 2
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 2
- 125000005494 pyridonyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl 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
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 claims 2
- GBDNNYXQNMLVNK-QFIPXVFZSA-N (2s)-1-[1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-3-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]indazole-5-carbonyl]azetidine-2-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C(C1=CC(=CC=C11)C(=O)N2[C@@H](CC2)C(O)=O)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 GBDNNYXQNMLVNK-QFIPXVFZSA-N 0.000 claims 1
- UMRSURSJLJTZNW-UHFFFAOYSA-N (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-3-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]indazole-5-carboxylate Chemical compound C1CN(C(C)C)CCC1NC(=O)C(C1=CC(=CC=C11)C(=O)OCC2=C(OC(=O)O2)C)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 UMRSURSJLJTZNW-UHFFFAOYSA-N 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- KVGZZAHHUNAVKZ-UHFFFAOYSA-N 1,4-Dioxin Chemical group O1C=COC=C1 KVGZZAHHUNAVKZ-UHFFFAOYSA-N 0.000 claims 1
- JEHPUCTZDWDCOF-UHFFFAOYSA-N 1-[1-[1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]indazole-3-carbonyl]piperidin-4-yl]pyrrolidin-2-one Chemical compound S1C(Cl)=CC=C1C1=CC(CN2C3=CC=CC=C3C(C(=O)N3CCC(CC3)N3C(CCC3)=O)=N2)=NO1 JEHPUCTZDWDCOF-UHFFFAOYSA-N 0.000 claims 1
- IDKVIUACXDFUPI-UHFFFAOYSA-N 1-[1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-3-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]indazole-5-carbonyl]azetidine-3-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C(C1=CC(=CC=C11)C(=O)N2CC(C2)C(O)=O)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 IDKVIUACXDFUPI-UHFFFAOYSA-N 0.000 claims 1
- UCOGQNWNGDHSTR-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-3-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]indazole-5-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C(C1=CC(=CC=C11)C(O)=O)=NN1CC(=O)NC1=CC=C(Cl)C=N1 UCOGQNWNGDHSTR-UHFFFAOYSA-N 0.000 claims 1
- KBFSGLLCTGPIPG-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-n-[4-(2-methylsulfonylphenyl)phenyl]indazole-3-carboxamide Chemical compound CS(=O)(=O)C1=CC=CC=C1C(C=C1)=CC=C1NC(=O)C(C1=CC=CC=C11)=NN1CC(=O)NC1=CC=C(Cl)C=N1 KBFSGLLCTGPIPG-UHFFFAOYSA-N 0.000 claims 1
- WRVRICIVRDTKED-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-n-[4-(2-oxopyrrolidin-1-yl)phenyl]indazole-3-carboxamide Chemical compound N1=CC(Cl)=CC=C1NC(=O)CN1C2=CC=CC=C2C(C(=O)NC=2C=CC(=CC=2)N2C(CCC2)=O)=N1 WRVRICIVRDTKED-UHFFFAOYSA-N 0.000 claims 1
- VVUMSEGSFBTNSX-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-n-[4-(3-oxomorpholin-4-yl)phenyl]indazole-3-carboxamide Chemical compound N1=CC(Cl)=CC=C1NC(=O)CN1C2=CC=CC=C2C(C(=O)NC=2C=CC(=CC=2)N2C(COCC2)=O)=N1 VVUMSEGSFBTNSX-UHFFFAOYSA-N 0.000 claims 1
- QKHCVDDNWPRPKJ-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-n-[4-(4-oxopyridin-1-yl)phenyl]indazole-3-carboxamide Chemical compound N1=CC(Cl)=CC=C1NC(=O)CN1C2=CC=CC=C2C(C(=O)NC=2C=CC(=CC=2)N2C=CC(=O)C=C2)=N1 QKHCVDDNWPRPKJ-UHFFFAOYSA-N 0.000 claims 1
- BXWLNXDYWIALPX-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-n-[4-(morpholine-4-carbonyl)phenyl]indazole-3-carboxamide Chemical compound N1=CC(Cl)=CC=C1NC(=O)CN1C2=CC=CC=C2C(C(=O)NC=2C=CC(=CC=2)C(=O)N2CCOCC2)=N1 BXWLNXDYWIALPX-UHFFFAOYSA-N 0.000 claims 1
- OHBZMRBVWAMLAH-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-n-[4-(piperidine-1-carbonyl)phenyl]indazole-3-carboxamide Chemical compound N1=CC(Cl)=CC=C1NC(=O)CN1C2=CC=CC=C2C(C(=O)NC=2C=CC(=CC=2)C(=O)N2CCCCC2)=N1 OHBZMRBVWAMLAH-UHFFFAOYSA-N 0.000 claims 1
- NFAXNLHCRMFJFB-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-3-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]indazole-5-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C(C1=CC(=CC=C11)C(O)=O)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 NFAXNLHCRMFJFB-UHFFFAOYSA-N 0.000 claims 1
- NNSKVZFGFBNHIL-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-3-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]indazole-6-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C(C1=CC=C(C=C11)C(O)=O)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 NNSKVZFGFBNHIL-UHFFFAOYSA-N 0.000 claims 1
- DQWRXNZSNWQYIT-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-3-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]indazole-7-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C(C1=CC=CC(=C11)C(O)=O)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 DQWRXNZSNWQYIT-UHFFFAOYSA-N 0.000 claims 1
- PXFNXCTWIJPKSS-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-4-(5-oxo-2h-1,2,4-oxadiazol-3-yl)-n-(1-propan-2-ylpiperidin-4-yl)indazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C(C1=C(C=2NC(=O)ON=2)C=CC=C11)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 PXFNXCTWIJPKSS-UHFFFAOYSA-N 0.000 claims 1
- IXVPVCVAEBQNBZ-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-4-cyano-n-(1-propan-2-ylpiperidin-4-yl)indazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C(C1=C(C#N)C=CC=C11)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 IXVPVCVAEBQNBZ-UHFFFAOYSA-N 0.000 claims 1
- RVTLPOZFTSUXFH-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)indazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C(C1=CC(=CC=C11)C(=O)N2CC(O)C2)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 RVTLPOZFTSUXFH-UHFFFAOYSA-N 0.000 claims 1
- PMGDUXTYSDBGSY-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)indazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C(C1=CC=CC=C11)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 PMGDUXTYSDBGSY-UHFFFAOYSA-N 0.000 claims 1
- BVXWYEPYDRNSQL-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(4-morpholin-4-ylphenyl)indazole-3-carboxamide Chemical compound S1C(Cl)=CC=C1C1=CC(CN2C3=CC=CC=C3C(C(=O)NC=3C=CC(=CC=3)N3CCOCC3)=N2)=NO1 BVXWYEPYDRNSQL-UHFFFAOYSA-N 0.000 claims 1
- VXQWAGJTWLIFDH-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(4-piperidin-1-ylphenyl)indazole-3-carboxamide Chemical compound S1C(Cl)=CC=C1C1=CC(CN2C3=CC=CC=C3C(C(=O)NC=3C=CC(=CC=3)N3CCCCC3)=N2)=NO1 VXQWAGJTWLIFDH-UHFFFAOYSA-N 0.000 claims 1
- QKAGFEIWMYZLMO-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-[4-(1h-imidazol-5-yl)phenyl]indazole-3-carboxamide Chemical compound S1C(Cl)=CC=C1C1=CC(CN2C3=CC=CC=C3C(C(=O)NC=3C=CC(=CC=3)C=3N=CNC=3)=N2)=NO1 QKAGFEIWMYZLMO-UHFFFAOYSA-N 0.000 claims 1
- UGIPZOXAEKRKFK-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-[4-(2-methylsulfonylphenyl)phenyl]indazole-3-carboxamide Chemical compound CS(=O)(=O)C1=CC=CC=C1C(C=C1)=CC=C1NC(=O)C(C1=CC=CC=C11)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 UGIPZOXAEKRKFK-UHFFFAOYSA-N 0.000 claims 1
- SOCAHGTXRMOISC-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-[4-(4-oxopyridin-1-yl)phenyl]indazole-3-carboxamide Chemical compound S1C(Cl)=CC=C1C1=CC(CN2C3=CC=CC=C3C(C(=O)NC=3C=CC(=CC=3)N3C=CC(=O)C=C3)=N2)=NO1 SOCAHGTXRMOISC-UHFFFAOYSA-N 0.000 claims 1
- QSYXCUFSJVNLAY-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-[4-(morpholine-4-carbonyl)phenyl]indazole-3-carboxamide Chemical compound S1C(Cl)=CC=C1C1=CC(CN2C3=CC=CC=C3C(C(=O)NC=3C=CC(=CC=3)C(=O)N3CCOCC3)=N2)=NO1 QSYXCUFSJVNLAY-UHFFFAOYSA-N 0.000 claims 1
- AQXVBKKENCHPEZ-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-[4-(pyrrolidine-1-carbonyl)phenyl]indazole-3-carboxamide Chemical compound S1C(Cl)=CC=C1C1=CC(CN2C3=CC=CC=C3C(C(=O)NC=3C=CC(=CC=3)C(=O)N3CCCC3)=N2)=NO1 AQXVBKKENCHPEZ-UHFFFAOYSA-N 0.000 claims 1
- QCYKPTBHTPMQQT-UHFFFAOYSA-N 1-ethoxycarbonyloxyethyl 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-3-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]indazole-5-carboxylate Chemical compound N1=C(C(=O)NC2CCN(CC2)C(C)C)C2=CC(C(=O)OC(C)OC(=O)OCC)=CC=C2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 QCYKPTBHTPMQQT-UHFFFAOYSA-N 0.000 claims 1
- ZRQQXFMGYSOKDF-UHFFFAOYSA-N 1-propan-2-ylpiperidin-4-amine Chemical compound CC(C)N1CCC(N)CC1 ZRQQXFMGYSOKDF-UHFFFAOYSA-N 0.000 claims 1
- OIWIYLWZIIJNHU-UHFFFAOYSA-N 1-sulfanylpyrazole Chemical compound SN1C=CC=N1 OIWIYLWZIIJNHU-UHFFFAOYSA-N 0.000 claims 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 1
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims 1
- XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 claims 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims 1
- HBJUQLMVCIEESP-UHFFFAOYSA-N 2,5-dihydro-1,2,4-oxadiazole Chemical compound C1NC=NO1 HBJUQLMVCIEESP-UHFFFAOYSA-N 0.000 claims 1
- SYOANZBNGDEJFH-UHFFFAOYSA-N 2,5-dihydro-1h-triazole Chemical compound C1NNN=C1 SYOANZBNGDEJFH-UHFFFAOYSA-N 0.000 claims 1
- ARGCQEVBJHPOGB-UHFFFAOYSA-N 2,5-dihydrofuran Chemical compound C1OCC=C1 ARGCQEVBJHPOGB-UHFFFAOYSA-N 0.000 claims 1
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 claims 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims 1
- PHMDCGHHYTWDCV-UHFFFAOYSA-N 2-[[1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-3-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]indazole-5-carbonyl]-methylamino]acetic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C(C1=CC(=CC=C11)C(=O)N(C)CC(O)=O)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 PHMDCGHHYTWDCV-UHFFFAOYSA-N 0.000 claims 1
- RELQLMDGQBZGEG-UHFFFAOYSA-N 2-[[1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-3-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]indazole-5-carbonyl]amino]acetic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C(C1=CC(=CC=C11)C(=O)NCC(O)=O)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 RELQLMDGQBZGEG-UHFFFAOYSA-N 0.000 claims 1
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- UVTYAMNNFOFWGD-UHFFFAOYSA-N 2-hydroxyethyl 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-3-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]indazole-5-carboxylate Chemical compound C1CN(C(C)C)CCC1NC(=O)C(C1=CC(=CC=C11)C(=O)OCCO)=NN1CC(=O)NC1=CC=C(Cl)C=N1 UVTYAMNNFOFWGD-UHFFFAOYSA-N 0.000 claims 1
- WGIVEWUYIRVGQS-UHFFFAOYSA-N 2-hydroxyethyl 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-3-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]indazole-5-carboxylate Chemical compound C1CN(C(C)C)CCC1NC(=O)C(C1=CC(=CC=C11)C(=O)OCCO)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 WGIVEWUYIRVGQS-UHFFFAOYSA-N 0.000 claims 1
- MKYYTDKGUURLQD-UHFFFAOYSA-N 2-methoxyethyl 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-3-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]indazole-5-carboxylate Chemical compound N1=C(C(=O)NC2CCN(CC2)C(C)C)C2=CC(C(=O)OCCOC)=CC=C2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 MKYYTDKGUURLQD-UHFFFAOYSA-N 0.000 claims 1
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 claims 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims 1
- BWCDLEQTELFBAW-UHFFFAOYSA-N 3h-dioxazole Chemical compound N1OOC=C1 BWCDLEQTELFBAW-UHFFFAOYSA-N 0.000 claims 1
- XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 claims 1
- IMISRHJROSMTLK-UHFFFAOYSA-N 5-(azetidine-1-carbonyl)-1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-n-(1-propan-2-ylpiperidin-4-yl)indazole-3-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C(C1=CC(=CC=C11)C(=O)N2CCC2)=NN1CC1=NOC(C=2SC(Cl)=CC=2)=C1 IMISRHJROSMTLK-UHFFFAOYSA-N 0.000 claims 1
- MMXPAXMXNNDEGC-UHFFFAOYSA-N COC(=O)C=1C=C2C=NN(C2=CC1)C(NC1CCN(CC1)C(C)C)=O Chemical compound COC(=O)C=1C=C2C=NN(C2=CC1)C(NC1CCN(CC1)C(C)C)=O MMXPAXMXNNDEGC-UHFFFAOYSA-N 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
- GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 claims 1
- 241000534944 Thia Species 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims 1
- 125000003725 azepanyl group Chemical group 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- FLKYBGKDCCEQQM-WYUVZMMLSA-M cefazolin sodium Chemical compound [Na+].S1C(C)=NN=C1SCC1=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)CN3N=NN=C3)[C@H]2SC1 FLKYBGKDCCEQQM-WYUVZMMLSA-M 0.000 claims 1
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 claims 1
- PDQJSKSWEAXWFV-UHFFFAOYSA-N ethyl 2-[[1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-3-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]indazole-5-carbonyl]amino]acetate Chemical compound N1=C(C(=O)NC2CCN(CC2)C(C)C)C2=CC(C(=O)NCC(=O)OCC)=CC=C2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 PDQJSKSWEAXWFV-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims 1
- KICHBBHPMUTAPL-UHFFFAOYSA-N indazole-1,3-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=NN(C(O)=O)C2=C1 KICHBBHPMUTAPL-UHFFFAOYSA-N 0.000 claims 1
- WTPIKKIAGARZPK-UHFFFAOYSA-N methyl 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-3-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]indazole-5-carboxylate Chemical compound N1=C(C(=O)NC2CCN(CC2)C(C)C)C2=CC(C(=O)OC)=CC=C2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 WTPIKKIAGARZPK-UHFFFAOYSA-N 0.000 claims 1
- PQWSKBKUYKURLY-UHFFFAOYSA-N methyl 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-3-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]indazole-6-carboxylate Chemical compound C12=CC(C(=O)OC)=CC=C2C(C(=O)NC2CCN(CC2)C(C)C)=NN1CC(=NO1)C=C1C1=CC=C(Cl)S1 PQWSKBKUYKURLY-UHFFFAOYSA-N 0.000 claims 1
- OCZKXMRENZSHEY-UHFFFAOYSA-N methyl 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-3-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]indazole-7-carboxylate Chemical compound C1=2C(C(=O)OC)=CC=CC=2C(C(=O)NC2CCN(CC2)C(C)C)=NN1CC(=NO1)C=C1C1=CC=C(Cl)S1 OCZKXMRENZSHEY-UHFFFAOYSA-N 0.000 claims 1
- XVNCDIZCJCFERZ-UHFFFAOYSA-N methyl 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-3-[[4-(3-oxomorpholin-4-yl)phenyl]carbamoyl]indazole-5-carboxylate Chemical compound N1=C(C(=O)NC=2C=CC(=CC=2)N2C(COCC2)=O)C2=CC(C(=O)OC)=CC=C2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 XVNCDIZCJCFERZ-UHFFFAOYSA-N 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- DSKAJRRQPFGCBH-UHFFFAOYSA-N n-(5-chloropyridin-2-yl)-2-[3-[4-(2-oxopyrrolidin-1-yl)piperidine-1-carbonyl]indazol-1-yl]acetamide Chemical compound N1=CC(Cl)=CC=C1NC(=O)CN1C2=CC=CC=C2C(C(=O)N2CCC(CC2)N2C(CCC2)=O)=N1 DSKAJRRQPFGCBH-UHFFFAOYSA-N 0.000 claims 1
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- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims 1
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| EP03011303.9 | 2003-05-19 | ||
| EP03011303A EP1479675A1 (en) | 2003-05-19 | 2003-05-19 | Indazole-derivatives as factor Xa inhibitors |
| PCT/EP2004/004753 WO2004101556A1 (en) | 2003-05-19 | 2004-05-05 | INDAZOLE-DERIVATIVES AS FACTOR Xa INHIBITORS |
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| WO (1) | WO2004101556A1 (enExample) |
Families Citing this family (28)
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|---|---|---|---|---|
| EP1581503A4 (en) * | 2002-11-08 | 2007-07-25 | Merck & Co Inc | OPHTHALMIC COMPOSITIONS FOR THE TREATMENT OF OCCULAR HYPERTONIA |
| US7358268B2 (en) * | 2002-12-04 | 2008-04-15 | Sanofi-Aventis Deutschland Gmbh | Imidazole derivatives as factor Xa inhibitors |
| US7429581B2 (en) * | 2002-12-23 | 2008-09-30 | Sanofi-Aventis Deutschland Gmbh | Pyrazole-derivatives as factor Xa inhibitors |
| US7223780B2 (en) * | 2003-05-19 | 2007-05-29 | Sanofi-Aventis Deutschland Gmbh | Triazole-derivatives as blood clotting enzyme factor Xa inhibitors |
| US7317027B2 (en) * | 2003-05-19 | 2008-01-08 | Sanofi-Aventis Deutschland Gmbh | Azaindole-derivatives as factor Xa inhibitors |
| EP1479677A1 (en) * | 2003-05-19 | 2004-11-24 | Aventis Pharma Deutschland GmbH | New indole derivatives as factor xa inhibitors |
| US7741341B2 (en) | 2003-05-19 | 2010-06-22 | Sanofi-Aventis Deutschland Gmbh | Benzimidazole-derivatives as factor Xa inhibitors |
| AU2004271978B2 (en) * | 2003-09-04 | 2009-02-05 | Merck & Co., Inc. | Ophthalmic compositions for treating ocular hypertension |
| DE10342570A1 (de) * | 2003-09-15 | 2005-04-14 | Bayer Healthcare Ag | Verfahren zur Herstellung von 4-(4-Aminophenyl)-3-morpholinon |
| EP1568698A1 (en) | 2004-02-27 | 2005-08-31 | Aventis Pharma Deutschland GmbH | Pyrrole-derivatives as factor Xa inhibitors |
| EP1571154A1 (en) * | 2004-03-03 | 2005-09-07 | Aventis Pharma Deutschland GmbH | Beta-aminoacid-derivatives as factor Xa inhibitors |
| CA2563617A1 (en) * | 2004-04-20 | 2005-11-03 | Rnd Pharmaceuticals | Pharmaceutical compositions and methods of use of lipophilic, silicon-substituted, cyclooxygenase-2 selective non-steroidal anti-inflammatory drugs and derivatives |
| DE102006030479A1 (de) * | 2006-07-01 | 2008-03-20 | Merck Patent Gmbh | Indazolderivate |
| DE102006032824A1 (de) * | 2006-07-14 | 2008-01-17 | Bayer Healthcare Ag | Substituierte Indazole |
| JO2701B1 (en) | 2006-12-21 | 2013-03-03 | جلاكسو جروب ليميتد | Vehicles |
| CN101821260B (zh) | 2007-08-14 | 2013-07-31 | 康塞特医药品有限公司 | 取代的噁唑烷酮衍生物 |
| MX358640B (es) | 2008-01-04 | 2018-08-29 | Intellikine Llc | Isoquinolin-1 (2h) -onas y tieno [2,3-d]pirimidin-4(3h) -onas substituidas, y metodos de uso de las mismas. |
| US8193182B2 (en) | 2008-01-04 | 2012-06-05 | Intellikine, Inc. | Substituted isoquinolin-1(2H)-ones, and methods of use thereof |
| DE102008022221A1 (de) * | 2008-05-06 | 2009-11-12 | Universität des Saarlandes | Inhibitoren der humanen Aldosteronsynthase CYP11B2 |
| US8541404B2 (en) * | 2009-11-09 | 2013-09-24 | Elexopharm Gmbh | Inhibitors of the human aldosterone synthase CYP11B2 |
| DE102010018299A1 (de) | 2010-04-23 | 2011-10-27 | Archimica Gmbh | Verfahren zur Herstellung von 4-(4-Aminophenyl)-morpholin-3-on |
| TWI546305B (zh) | 2011-01-10 | 2016-08-21 | 英菲尼提製藥股份有限公司 | 製備異喹啉酮之方法及異喹啉酮之固體形式 |
| EP2705028B1 (en) | 2011-05-06 | 2019-08-21 | Egis Gyógyszergyár Zrt. | Process for the preparation of a rivaroxaban and intermediates formed in said process |
| US8828998B2 (en) | 2012-06-25 | 2014-09-09 | Infinity Pharmaceuticals, Inc. | Treatment of lupus, fibrotic conditions, and inflammatory myopathies and other disorders using PI3 kinase inhibitors |
| CN105102000B (zh) | 2012-11-01 | 2021-10-22 | 无限药品公司 | 使用pi3激酶亚型调节剂的癌症疗法 |
| WO2015160975A2 (en) | 2014-04-16 | 2015-10-22 | Infinity Pharmaceuticals, Inc. | Combination therapies |
| EP3474856B1 (en) | 2016-06-24 | 2022-09-14 | Infinity Pharmaceuticals, Inc. | Combination therapies |
| CN109456205B (zh) * | 2018-12-17 | 2021-09-21 | 石河子大学 | 以取代喹啉或异喹啉酰肼吡啶-n-氧化物为配体的水相体系中的n-芳基化方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5506134A (en) | 1990-10-22 | 1996-04-09 | Corvas International, Inc. | Hypridoma and monoclonal antibody which inhibits blood coagulation tissue factor/factor VIIa complex |
| US5833982A (en) | 1991-02-28 | 1998-11-10 | Zymogenetics, Inc. | Modified factor VII |
| US5788965A (en) | 1991-02-28 | 1998-08-04 | Novo Nordisk A/S | Modified factor VII |
| CA2186497C (en) | 1994-04-26 | 2008-06-17 | Fahad Al-Obeidi | Factor xa inhibitors |
| US5998424A (en) * | 1997-06-19 | 1999-12-07 | Dupont Pharmaceuticals Company | Inhibitors of factor Xa with a neutral P1 specificity group |
| US6339099B1 (en) * | 1997-06-20 | 2002-01-15 | Dupont Pharmaceuticals Company | Guanidine mimics as factor Xa inhibitors |
| EP0987274A1 (en) | 1998-09-15 | 2000-03-22 | Hoechst Marion Roussel Deutschland GmbH | Factor VIIa Inhibitors |
| WO2000039131A1 (en) * | 1998-12-23 | 2000-07-06 | Du Pont Pharmaceuticals Company | Nitrogen containing heterobicycles as factor xa inhibitors |
| HUP0203375A3 (en) | 1999-07-28 | 2005-03-29 | Aventis Pharm Prod Inc | Substituted oxoazaheterocyclyl compounds |
| DE10014645A1 (de) | 2000-03-24 | 2001-09-27 | Merck Patent Gmbh | Substituierte Biphenylderivate |
| CA2409762A1 (en) * | 2000-06-23 | 2002-01-03 | Donald J.P. Pinto | Heteroaryl-phenyl substituted factor xa inhibitors |
| EP1217000A1 (en) | 2000-12-23 | 2002-06-26 | Aventis Pharma Deutschland GmbH | Inhibitors of factor Xa and factor VIIa |
| US7157487B2 (en) * | 2000-12-28 | 2007-01-02 | Daiichi Pharmaceutical Co., Ltd. | Vla-4 inhibitors |
| EP1314733A1 (en) | 2001-11-22 | 2003-05-28 | Aventis Pharma Deutschland GmbH | Indole-2-carboxamides as factor Xa inhibitors |
| US7358268B2 (en) | 2002-12-04 | 2008-04-15 | Sanofi-Aventis Deutschland Gmbh | Imidazole derivatives as factor Xa inhibitors |
| US7429581B2 (en) | 2002-12-23 | 2008-09-30 | Sanofi-Aventis Deutschland Gmbh | Pyrazole-derivatives as factor Xa inhibitors |
| US7741341B2 (en) | 2003-05-19 | 2010-06-22 | Sanofi-Aventis Deutschland Gmbh | Benzimidazole-derivatives as factor Xa inhibitors |
| EP1479677A1 (en) | 2003-05-19 | 2004-11-24 | Aventis Pharma Deutschland GmbH | New indole derivatives as factor xa inhibitors |
| US7223780B2 (en) | 2003-05-19 | 2007-05-29 | Sanofi-Aventis Deutschland Gmbh | Triazole-derivatives as blood clotting enzyme factor Xa inhibitors |
| US7317027B2 (en) | 2003-05-19 | 2008-01-08 | Sanofi-Aventis Deutschland Gmbh | Azaindole-derivatives as factor Xa inhibitors |
| EP1568698A1 (en) | 2004-02-27 | 2005-08-31 | Aventis Pharma Deutschland GmbH | Pyrrole-derivatives as factor Xa inhibitors |
| EP1571154A1 (en) | 2004-03-03 | 2005-09-07 | Aventis Pharma Deutschland GmbH | Beta-aminoacid-derivatives as factor Xa inhibitors |
-
2003
- 2003-05-19 EP EP03011303A patent/EP1479675A1/en not_active Withdrawn
-
2004
- 2004-05-05 EP EP04731155A patent/EP1628972B1/en not_active Expired - Lifetime
- 2004-05-05 BR BRPI0410430-7A patent/BRPI0410430A/pt not_active IP Right Cessation
- 2004-05-05 MX MXPA05012346A patent/MXPA05012346A/es active IP Right Grant
- 2004-05-05 AU AU2004238499A patent/AU2004238499A1/en not_active Abandoned
- 2004-05-05 DE DE602004020761T patent/DE602004020761D1/de not_active Expired - Lifetime
- 2004-05-05 CA CA002528220A patent/CA2528220A1/en not_active Abandoned
- 2004-05-05 AT AT04731155T patent/ATE429432T1/de not_active IP Right Cessation
- 2004-05-05 JP JP2006529742A patent/JP4709763B2/ja not_active Expired - Fee Related
- 2004-05-05 WO PCT/EP2004/004753 patent/WO2004101556A1/en not_active Ceased
- 2004-05-07 PE PE2004000474A patent/PE20050153A1/es not_active Application Discontinuation
- 2004-05-17 TW TW093113796A patent/TW200510400A/zh unknown
- 2004-05-17 CL CL200401080A patent/CL2004001080A1/es unknown
- 2004-05-19 US US10/849,088 patent/US7365088B2/en not_active Expired - Fee Related
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