IL201620A - Quinoline-carboxamide derivatives as 12 y 2p antagonists - Google Patents

Info

Publication number

IL201620A

IL201620A IL201620A IL20162009A IL201620A IL 201620 A IL201620 A IL 201620A IL 201620 A IL201620 A IL 201620A IL 20162009 A IL20162009 A IL 20162009A IL 201620 A IL201620 A IL 201620A

Authority

IL

Israel

Prior art keywords

oxo

ethoxy

piperazine

carboxylic acid

carbonyl

Prior art date

2007-04-23

Links

• Espacenet
• Global Dossier
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• 239000005557 antagonist Substances 0.000 title claims abstract description 17
• ZEXKKIXCRDTKBF-UHFFFAOYSA-N quinoline-2-carboxamide Chemical class C1=CC=CC2=NC(C(=O)N)=CC=C21 ZEXKKIXCRDTKBF-UHFFFAOYSA-N 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 389
• 238000000034 method Methods 0.000 claims abstract description 260
• 239000003814 drug Substances 0.000 claims abstract description 21
• 239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 14
• 238000002360 preparation method Methods 0.000 claims abstract description 13
• 238000002560 therapeutic procedure Methods 0.000 claims abstract description 13
• 238000011321 prophylaxis Methods 0.000 claims abstract description 12
• 229910052740 iodine Inorganic materials 0.000 claims abstract description 9
• 230000008569 process Effects 0.000 claims abstract description 9
• 208000001435 Thromboembolism Diseases 0.000 claims abstract description 6
• -1 dihydro-oxazepine Chemical compound 0.000 claims description 372
• 239000002253 acid Substances 0.000 claims description 223
• 125000004494 ethyl ester group Chemical group 0.000 claims description 123
• 238000006243 chemical reaction Methods 0.000 claims description 72
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 67
• 125000000623 heterocyclic group Chemical group 0.000 claims description 66
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 65
• 150000003839 salts Chemical class 0.000 claims description 56
• 125000000217 alkyl group Chemical group 0.000 claims description 53
• 239000000203 mixture Substances 0.000 claims description 50
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 45
• 229910052736 halogen Inorganic materials 0.000 claims description 44
• 150000002367 halogens Chemical class 0.000 claims description 44
• 239000003112 inhibitor Substances 0.000 claims description 44
• 229910052757 nitrogen Inorganic materials 0.000 claims description 43
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 38
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 38
• 230000015572 biosynthetic process Effects 0.000 claims description 38
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 34
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 33
• 150000002148 esters Chemical class 0.000 claims description 32
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 30
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
• 239000003795 chemical substances by application Substances 0.000 claims description 27
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 27
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 26
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 25
• 125000004076 pyridyl group Chemical group 0.000 claims description 25
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 24
• UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 20
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
• 125000001544 thienyl group Chemical group 0.000 claims description 20
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 19
• LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 18
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 18
• 208000007536 Thrombosis Diseases 0.000 claims description 18
• 239000001257 hydrogen Substances 0.000 claims description 18
• 229910052739 hydrogen Inorganic materials 0.000 claims description 18
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 16
• 125000004429 atom Chemical group 0.000 claims description 16
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 16
• FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 15
• RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
• MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 15
• USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims description 15
• ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 claims description 15
• XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 14
• HTFFABIIOAKIBH-UHFFFAOYSA-N diazinane Chemical compound C1CCNNC1 HTFFABIIOAKIBH-UHFFFAOYSA-N 0.000 claims description 14
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 14
• 239000002243 precursor Substances 0.000 claims description 14
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
• UZHVXJZEHGSWQV-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydrocyclopenta[c]pyrrole Chemical compound C1NCC2CCCC21 UZHVXJZEHGSWQV-UHFFFAOYSA-N 0.000 claims description 13
• IGERFAHWSHDDHX-UHFFFAOYSA-N 1,3-dioxanyl Chemical group [CH]1OCCCO1 IGERFAHWSHDDHX-UHFFFAOYSA-N 0.000 claims description 13
• NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 13
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 13
• DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 claims description 13
• JZFICWYCTCCINF-UHFFFAOYSA-N Thiadiazin Chemical compound S=C1SC(C)NC(C)N1CCN1C(=S)SC(C)NC1C JZFICWYCTCCINF-UHFFFAOYSA-N 0.000 claims description 13
• 125000002393 azetidinyl group Chemical group 0.000 claims description 13
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 13
• 125000003566 oxetanyl group Chemical group 0.000 claims description 13
• 229910052760 oxygen Inorganic materials 0.000 claims description 13
• 239000001301 oxygen Substances 0.000 claims description 13
• 125000003386 piperidinyl group Chemical group 0.000 claims description 13
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 13
• 229910052717 sulfur Inorganic materials 0.000 claims description 13
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 13
• 150000003536 tetrazoles Chemical class 0.000 claims description 13
• 125000000335 thiazolyl group Chemical group 0.000 claims description 13
• LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 claims description 12
• CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 claims description 12
• JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 claims description 12
• ZNGWEEUXTBNKFR-UHFFFAOYSA-N 1,4-oxazepane Chemical compound C1CNCCOC1 ZNGWEEUXTBNKFR-UHFFFAOYSA-N 0.000 claims description 12
• MSRJJSCOWHWGGX-UHFFFAOYSA-N 2h-1,3-diazepine Chemical compound C1N=CC=CC=N1 MSRJJSCOWHWGGX-UHFFFAOYSA-N 0.000 claims description 12
• WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims description 12
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
• 229910052799 carbon Inorganic materials 0.000 claims description 12
• DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 12
• 125000002541 furyl group Chemical group 0.000 claims description 12
• OXUZCBDDXOMZAM-UHFFFAOYSA-N oxathiepane Chemical compound C1CCOSCC1 OXUZCBDDXOMZAM-UHFFFAOYSA-N 0.000 claims description 12
• DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims description 12
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 12
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
• 239000011593 sulfur Substances 0.000 claims description 12
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 12
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 12
• CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 claims description 12
• CZSRXHJVZUBEGW-UHFFFAOYSA-N 1,2-thiazolidine Chemical compound C1CNSC1 CZSRXHJVZUBEGW-UHFFFAOYSA-N 0.000 claims description 11
• KGWNRZLPXLBMPS-UHFFFAOYSA-N 2h-1,3-oxazine Chemical compound C1OC=CC=N1 KGWNRZLPXLBMPS-UHFFFAOYSA-N 0.000 claims description 11
• NTYABNDBNKVWOO-UHFFFAOYSA-N 2h-1,3-thiazine Chemical compound C1SC=CC=N1 NTYABNDBNKVWOO-UHFFFAOYSA-N 0.000 claims description 11
• BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 11
• AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 claims description 11
• BWCDLEQTELFBAW-UHFFFAOYSA-N 3h-dioxazole Chemical compound N1OOC=C1 BWCDLEQTELFBAW-UHFFFAOYSA-N 0.000 claims description 11
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
• 125000004432 carbon atom Chemical group C* 0.000 claims description 11
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 11
• 125000000160 oxazolidinyl group Chemical group 0.000 claims description 11
• IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims description 11
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 11
• 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 10
• BKWQKVJYXODDAC-UHFFFAOYSA-N 1,2-dihydropyridazine Chemical compound N1NC=CC=C1 BKWQKVJYXODDAC-UHFFFAOYSA-N 0.000 claims description 10
• LKLLNYWECKEQIB-UHFFFAOYSA-N 1,3,5-triazinane Chemical compound C1NCNCN1 LKLLNYWECKEQIB-UHFFFAOYSA-N 0.000 claims description 10
• ZBOWKDHBOFMERX-UHFFFAOYSA-N 1,3-diazepane Chemical compound C1CCNCNC1 ZBOWKDHBOFMERX-UHFFFAOYSA-N 0.000 claims description 10
• POXWDTQUDZUOGP-UHFFFAOYSA-N 1h-1,4-diazepine Chemical compound N1C=CC=NC=C1 POXWDTQUDZUOGP-UHFFFAOYSA-N 0.000 claims description 10
• VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 claims description 10
• YHWMFDLNZGIJSD-UHFFFAOYSA-N 2h-1,4-oxazine Chemical compound C1OC=CN=C1 YHWMFDLNZGIJSD-UHFFFAOYSA-N 0.000 claims description 10
• WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 10
• ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 10
• 229910052794 bromium Inorganic materials 0.000 claims description 10
• IFCOISJMMCWJME-WNJJXGMVSA-N butyl 4-[(2s)-2-[[4-[2-[(2s)-2-(cyclobutylcarbamoyl)pyrrolidin-1-yl]-2-oxoethoxy]-7-methylquinoline-2-carbonyl]amino]-4-hydroxybutanoyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCCCC)CCN1C(=O)[C@H](CCO)NC(=O)C1=CC(OCC(=O)N2[C@@H](CCC2)C(=O)NC2CCC2)=C(C=CC(C)=C2)C2=N1 IFCOISJMMCWJME-WNJJXGMVSA-N 0.000 claims description 10
• VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical group [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 claims description 10
• AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 10
• SFJGCXYXEFWEBK-UHFFFAOYSA-N oxazepine Chemical compound O1C=CC=CC=N1 SFJGCXYXEFWEBK-UHFFFAOYSA-N 0.000 claims description 10
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 10
• 125000002053 thietanyl group Chemical group 0.000 claims description 10
• UOBKULMUFKXXEA-UHFFFAOYSA-N triazepane Chemical compound C1CCNNNC1 UOBKULMUFKXXEA-UHFFFAOYSA-N 0.000 claims description 10
• OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 9
• JWGMXWNVAYWSNI-UHFFFAOYSA-N 1-cyclohexyldiazinane Chemical compound C1CCCCC1N1NCCCC1 JWGMXWNVAYWSNI-UHFFFAOYSA-N 0.000 claims description 9
• BEWVAZNECYSPMT-UHFFFAOYSA-N 2,3-dihydro-1h-azepine Chemical compound C1CC=CC=CN1 BEWVAZNECYSPMT-UHFFFAOYSA-N 0.000 claims description 9
• GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical compound C1CC=NS1 GUUULVAMQJLDSY-UHFFFAOYSA-N 0.000 claims description 9
• 239000003146 anticoagulant agent Substances 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 229910052731 fluorine Inorganic materials 0.000 claims description 9
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 9
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 9
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 9
• 125000002950 monocyclic group Chemical group 0.000 claims description 9
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 9
• 238000001356 surgical procedure Methods 0.000 claims description 9
• POTIYWUALSJREP-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroquinoline Chemical compound N1CCCC2CCCCC21 POTIYWUALSJREP-UHFFFAOYSA-N 0.000 claims description 8
• OQJVXNHMUWQQEW-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrazine Chemical compound C1CNC=CN1 OQJVXNHMUWQQEW-UHFFFAOYSA-N 0.000 claims description 8
• VWKKSBDTNICZRS-UHFFFAOYSA-N 1,2,4-triazinane Chemical compound C1CNNCN1 VWKKSBDTNICZRS-UHFFFAOYSA-N 0.000 claims description 8
• QQUFDFQHIUKUFP-UHFFFAOYSA-N 1-azaspiro[2.2]pentane Chemical compound C1CC11NC1 QQUFDFQHIUKUFP-UHFFFAOYSA-N 0.000 claims description 8
• VGMJQHONPAXABH-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1h-pyrazolo[4,3-c]pyridine Chemical compound C1NCCC2=C1C=NN2 VGMJQHONPAXABH-UHFFFAOYSA-N 0.000 claims description 8
• YIGDNAMSWMGZNW-UHFFFAOYSA-N 4,5,6,7-tetrahydro-[1,2]oxazolo[4,5-c]pyridine Chemical compound C1NCCC2=C1C=NO2 YIGDNAMSWMGZNW-UHFFFAOYSA-N 0.000 claims description 8
• WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims description 8
• PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 claims description 8
• 230000009977 dual effect Effects 0.000 claims description 8
• LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 claims description 8
• CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 claims description 8
• 125000002757 morpholinyl group Chemical group 0.000 claims description 8
• 125000000183 1,4-thiazinyl group Chemical group S1C(C=NC=C1)* 0.000 claims description 7
• QUIJMHDIAFOPRK-UHFFFAOYSA-N 1-cyclooctylazocane Chemical compound C1CCCCCCC1N1CCCCCCC1 QUIJMHDIAFOPRK-UHFFFAOYSA-N 0.000 claims description 7
• PDELQDSYLBLPQO-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-indole Chemical compound C1CCCC2NCCC21 PDELQDSYLBLPQO-UHFFFAOYSA-N 0.000 claims description 7
• SCEIUGQQBYRBPP-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-azepine Chemical compound C1CCC=CNC1 SCEIUGQQBYRBPP-UHFFFAOYSA-N 0.000 claims description 7
• UKHJNJFJCGBKSF-UHFFFAOYSA-N 2,5-diazabicyclo[2.2.1]heptane Chemical compound C1NC2CNC1C2 UKHJNJFJCGBKSF-UHFFFAOYSA-N 0.000 claims description 7
• HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 claims description 7
• BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims description 7
• 230000001575 pathological effect Effects 0.000 claims description 7
• 229940044551 receptor antagonist Drugs 0.000 claims description 7
• 239000002464 receptor antagonist Substances 0.000 claims description 7
• 208000037803 restenosis Diseases 0.000 claims description 7
• 230000002792 vascular Effects 0.000 claims description 7
• OPBSNAYKUYMJDO-UHFFFAOYSA-N 1,2,3,4,6,7-hexahydropyrrolo[1,2-a]pyrazine Chemical compound C1CNCC2=CCCN21 OPBSNAYKUYMJDO-UHFFFAOYSA-N 0.000 claims description 6
• 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 claims description 6
• 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims description 6
• LLSRLLPHUVVLQJ-UHFFFAOYSA-N 1-cycloheptyldiazepane Chemical compound C1CCCCCC1N1NCCCCC1 LLSRLLPHUVVLQJ-UHFFFAOYSA-N 0.000 claims description 6
• JMWPSCUIQIMVQH-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-pyrrolo[3,4-c]pyridine Chemical compound C1NCCC2CNCC21 JMWPSCUIQIMVQH-UHFFFAOYSA-N 0.000 claims description 6
• QSLDIPUHQBHQGY-UHFFFAOYSA-N 4,5,6,7-tetrahydro-[1,3]thiazolo[5,4-c]pyridine Chemical compound C1NCCC2=C1SC=N2 QSLDIPUHQBHQGY-UHFFFAOYSA-N 0.000 claims description 6
• HXNOEHIMWZDRTK-UHFFFAOYSA-N 4,5,6,7-tetrahydrothieno[2,3-c]pyridine Chemical compound C1NCCC2=C1SC=C2 HXNOEHIMWZDRTK-UHFFFAOYSA-N 0.000 claims description 6
• 108010058207 Anistreplase Proteins 0.000 claims description 6
• BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 6
• JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 claims description 6
• 102000007625 Hirudins Human genes 0.000 claims description 6
• 108010007267 Hirudins Proteins 0.000 claims description 6
• 108090000435 Urokinase-type plasminogen activator Proteins 0.000 claims description 6
• 102000003990 Urokinase-type plasminogen activator Human genes 0.000 claims description 6
• 239000000556 agonist Substances 0.000 claims description 6
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
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• XSNMGLZVFNDDPW-ZWKOTPCHSA-N (2s)-1-[(2r)-2-[3-chloro-5-(difluoromethoxy)phenyl]-2-hydroxyacetyl]-n-[[4-(n'-methoxycarbamimidoyl)phenyl]methyl]azetidine-2-carboxamide Chemical compound C1=CC(C(/N)=N/OC)=CC=C1CNC(=O)[C@H]1N(C(=O)[C@H](O)C=2C=C(OC(F)F)C=C(Cl)C=2)CC1 XSNMGLZVFNDDPW-ZWKOTPCHSA-N 0.000 claims 1
• PUNVVUBNSWNROR-OZXSUGGESA-N (2s)-1-[2-[2-[[(2s)-4-carboxy-1-(4-ethoxycarbonylpiperazin-1-yl)-1-oxobutan-2-yl]carbamoyl]quinolin-4-yl]oxyacetyl]-2,3-dihydroindole-2-carboxylic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2C3=CC=CC=C3C[C@H]2C(O)=O)=C(C=CC=C2)C2=N1 PUNVVUBNSWNROR-OZXSUGGESA-N 0.000 claims 1
• FMCAFXHLMUOIGG-IWFBPKFRSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-IWFBPKFRSA-N 0.000 claims 1
• PQLBJVPZXNPVOS-HLBWOJLBSA-N (3r,3as,4s,4ar,8as,9ar)-3-methyl-4-[(e)-2-[5-[3-(trifluoromethyl)phenyl]pyridin-2-yl]ethenyl]-3a,4,4a,5,6,7,8,8a,9,9a-decahydro-3h-benzo[f][2]benzofuran-1-one Chemical compound C(/[C@H]1[C@@H]2CCCC[C@H]2C[C@H]2C(=O)O[C@@H]([C@@H]12)C)=C\C(N=C1)=CC=C1C1=CC=CC(C(F)(F)F)=C1 PQLBJVPZXNPVOS-HLBWOJLBSA-N 0.000 claims 1
• IBDOHNFYTPIZBQ-SVBPBHIXSA-N (3s)-3-[[4-[2-[(2s)-2-(cyclopentylcarbamoyl)pyrrolidin-1-yl]-2-oxoethoxy]-7-methylquinoline-2-carbonyl]amino]-4-(4-ethoxycarbonylpiperazin-1-yl)-4-oxobutanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CC(O)=O)NC(=O)C1=CC(OCC(=O)N2[C@@H](CCC2)C(=O)NC2CCCC2)=C(C=CC(C)=C2)C2=N1 IBDOHNFYTPIZBQ-SVBPBHIXSA-N 0.000 claims 1
• JVFUGHOEIPXCIB-UIOOFZCWSA-N (3s)-3-[[4-[2-[(2s)-2-(cyclopentylcarbamoyl)pyrrolidin-1-yl]-2-oxoethoxy]quinoline-2-carbonyl]amino]-4-(4-ethoxycarbonylpiperazin-1-yl)-4-oxobutanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CC(O)=O)NC(=O)C1=CC(OCC(=O)N2[C@@H](CCC2)C(=O)NC2CCCC2)=C(C=CC=C2)C2=N1 JVFUGHOEIPXCIB-UIOOFZCWSA-N 0.000 claims 1
• GHGYQLLPFTXBIX-CYFREDJKSA-N (3s)-4-(4-ethoxycarbonylpiperazin-1-yl)-3-[[4-[(2s)-1-(4-hydroxypiperidin-1-yl)-1-oxopropan-2-yl]oxy-7-methylquinoline-2-carbonyl]amino]-4-oxobutanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CC(O)=O)NC(=O)C1=CC(O[C@@H](C)C(=O)N2CCC(O)CC2)=C(C=CC(C)=C2)C2=N1 GHGYQLLPFTXBIX-CYFREDJKSA-N 0.000 claims 1
• BAXMDRUAWNAPDT-NRFANRHFSA-N (4s)-4-[[4-[2-(2,2-dimethyl-3-oxopiperazin-1-yl)-2-oxoethoxy]-7-methylquinoline-2-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2C(C(=O)NCC2)(C)C)=C(C=CC(C)=C2)C2=N1 BAXMDRUAWNAPDT-NRFANRHFSA-N 0.000 claims 1
• HUKZEZJZIQILFF-FQEVSTJZSA-N (4s)-4-[[4-[2-(3,3-difluoropyrrolidin-1-yl)-2-oxoethoxy]quinoline-2-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2CC(F)(F)CC2)=C(C=CC=C2)C2=N1 HUKZEZJZIQILFF-FQEVSTJZSA-N 0.000 claims 1
• MCHVZVPYMUJHFX-WKDCXCOVSA-N (4s)-4-[[4-[2-(3-anilinopyrrolidin-1-yl)-2-oxoethoxy]quinoline-2-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2CC(CC2)NC=2C=CC=CC=2)=C(C=CC=C2)C2=N1 MCHVZVPYMUJHFX-WKDCXCOVSA-N 0.000 claims 1
• FRWIVCYVPUGUBH-IPJJNNNSSA-N (4s)-4-[[4-[2-[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]-2-oxoethoxy]quinoline-2-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound O=C([C@H](CCC(O)=O)NC(=O)C=1C=C(C2=CC=CC=C2N=1)OCC(=O)N1C[C@]2(NC[C@]1([H])C2)[H])N1CCN(C(=O)OCC)CC1 FRWIVCYVPUGUBH-IPJJNNNSSA-N 0.000 claims 1
• PHQIJAPXDTWPPC-UPVQGACJSA-N (4s)-4-[[4-[2-[(2s)-2-(cyclobutylcarbamoyl)azetidin-1-yl]-2-oxoethoxy]-8-fluoroquinoline-2-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2[C@@H](CC2)C(=O)NC2CCC2)=C(C=CC=C2F)C2=N1 PHQIJAPXDTWPPC-UPVQGACJSA-N 0.000 claims 1
• LRRIYCMIYCBBHV-OZXSUGGESA-N (4s)-4-[[4-[2-[(2s)-2-(cyclobutylcarbamoyl)pyrrolidin-1-yl]-2-oxoethoxy]-5-fluoro-7-methylquinoline-2-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2[C@@H](CCC2)C(=O)NC2CCC2)=C(C(F)=CC(C)=C2)C2=N1 LRRIYCMIYCBBHV-OZXSUGGESA-N 0.000 claims 1
• NGKQQHMHKYZOHJ-OZXSUGGESA-N (4s)-4-[[4-[2-[(2s)-2-(cyclobutylcarbamoyl)pyrrolidin-1-yl]-2-oxoethoxy]-6,7-difluoroquinoline-2-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2[C@@H](CCC2)C(=O)NC2CCC2)=C(C=C(F)C(F)=C2)C2=N1 NGKQQHMHKYZOHJ-OZXSUGGESA-N 0.000 claims 1
• DJKFOXMNBDSOFN-LSYYVWMOSA-N (4s)-4-[[4-[2-[(2s)-2-(cyclopentylcarbamoyl)pyrrolidin-1-yl]-2-oxoethoxy]-7-methylquinoline-2-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2[C@@H](CCC2)C(=O)NC2CCCC2)=C(C=CC(C)=C2)C2=N1 DJKFOXMNBDSOFN-LSYYVWMOSA-N 0.000 claims 1
• AKGFUGJUVBBHIO-UIOOFZCWSA-N (4s)-4-[[4-[2-[(2s)-2-(cyclopropylcarbamoyl)pyrrolidin-1-yl]-2-oxoethoxy]naphthalene-2-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2[C@@H](CCC2)C(=O)NC2CC2)=C(C=CC=C2)C2=C1 AKGFUGJUVBBHIO-UIOOFZCWSA-N 0.000 claims 1
• PCZSPQLYXNTLJU-UGKGYDQZSA-N (4s)-4-[[4-[2-[(2s)-2-cyanopyrrolidin-1-yl]-2-oxoethoxy]quinoline-2-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2[C@@H](CCC2)C#N)=C(C=CC=C2)C2=N1 PCZSPQLYXNTLJU-UGKGYDQZSA-N 0.000 claims 1
• ORGOMJIJRSSPSU-URXFXBBRSA-N (4s)-4-[[4-[2-[(3s)-3-(cyclopropylcarbamoyl)pyrrolidin-1-yl]-2-oxoethoxy]-7-methylquinoline-2-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2C[C@H](CC2)C(=O)NC2CC2)=C(C=CC(C)=C2)C2=N1 ORGOMJIJRSSPSU-URXFXBBRSA-N 0.000 claims 1
• RFRZNNMYPZSECH-MBCWZBCWSA-N (4s)-4-[[4-[2-[2-(2,5-dimethylphenyl)pyrrolidin-1-yl]-2-oxoethoxy]quinoline-2-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2C(CCC2)C=2C(=CC=C(C)C=2)C)=C(C=CC=C2)C2=N1 RFRZNNMYPZSECH-MBCWZBCWSA-N 0.000 claims 1
• BPPSIEAFPCIROQ-TUXUZCGSSA-N (4s)-4-[[4-[2-[3-(diethylamino)pyrrolidin-1-yl]-2-oxoethoxy]quinoline-2-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2CC(CC2)N(CC)CC)=C(C=CC=C2)C2=N1 BPPSIEAFPCIROQ-TUXUZCGSSA-N 0.000 claims 1
• SHZZLDXPERQEQA-SMCANUKXSA-N (4s)-5-(4-benzoylpiperidin-1-yl)-4-[[4-[2-[(2s)-2-(cyclobutylcarbamoyl)pyrrolidin-1-yl]-2-oxoethoxy]quinoline-2-carbonyl]amino]-5-oxopentanoic acid Chemical compound O=C([C@@H]1CCCN1C(=O)COC=1C=C(N=C2C=CC=CC2=1)C(=O)N[C@@H](CCC(=O)O)C(=O)N1CCC(CC1)C(=O)C=1C=CC=CC=1)NC1CCC1 SHZZLDXPERQEQA-SMCANUKXSA-N 0.000 claims 1
• XUMZXCKWTGAWKQ-KXGYFKBOSA-N (4s)-5-(4-butoxycarbonylpiperazin-1-yl)-4-[[4-[2-[(2s)-2-[(2,2-difluorocyclopropyl)carbamoyl]pyrrolidin-1-yl]-2-oxoethoxy]-7-methylquinoline-2-carbonyl]amino]-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCCCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2[C@@H](CCC2)C(=O)NC2C(C2)(F)F)=C(C=CC(C)=C2)C2=N1 XUMZXCKWTGAWKQ-KXGYFKBOSA-N 0.000 claims 1
• AGJYSUZQWQLDRM-IAXKEJLGSA-N (4s)-5-(4-butoxycarbonylpiperazin-1-yl)-4-[[7-methyl-4-[2-(5-methyl-3-oxopyrazolidin-1-yl)-2-oxoethoxy]quinoline-2-carbonyl]amino]-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCCCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2C(CC(=O)N2)C)=C(C=CC(C)=C2)C2=N1 AGJYSUZQWQLDRM-IAXKEJLGSA-N 0.000 claims 1
• ZMJAKOLRTWRHLU-NRFANRHFSA-N (4s)-5-(4-butoxycarbonylpiperazin-1-yl)-4-[[7-methyl-4-[2-oxo-2-(3-oxopyrazolidin-1-yl)ethoxy]quinoline-2-carbonyl]amino]-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCCCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2NC(=O)CC2)=C(C=CC(C)=C2)C2=N1 ZMJAKOLRTWRHLU-NRFANRHFSA-N 0.000 claims 1
• NFYVXHZMNXTJGN-BBQAJUCSSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-(2-ethyl-3-oxopiperazin-1-yl)-2-oxoethoxy]quinoline-2-carbonyl]amino]-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2C(C(=O)NCC2)CC)=C(C=CC=C2)C2=N1 NFYVXHZMNXTJGN-BBQAJUCSSA-N 0.000 claims 1
• PBEQIJHJYIOEHU-QBGQUKIHSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-(2-methyl-2,3-dihydroindol-1-yl)-2-oxoethoxy]quinoline-2-carbonyl]amino]-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2C3=CC=CC=C3CC2C)=C(C=CC=C2)C2=N1 PBEQIJHJYIOEHU-QBGQUKIHSA-N 0.000 claims 1
• JSCCGNBSGGRWLE-ZYZRXSCRSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-(2-methyl-3-oxopiperazin-1-yl)-2-oxoethoxy]quinoline-2-carbonyl]amino]-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2C(C(=O)NCC2)C)=C(C=CC=C2)C2=N1 JSCCGNBSGGRWLE-ZYZRXSCRSA-N 0.000 claims 1
• DKTGDAXKLVMTEP-NRFANRHFSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-(2-methyl-4,6-dihydropyrrolo[3,4-d][1,3]thiazol-5-yl)-2-oxoethoxy]quinoline-2-carbonyl]amino]-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2CC=3SC(C)=NC=3C2)=C(C=CC=C2)C2=N1 DKTGDAXKLVMTEP-NRFANRHFSA-N 0.000 claims 1
• WQHIUFKVRXWOIV-JWIMYKKASA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-(4-methyl-6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)-2-oxoethoxy]quinoline-2-carbonyl]amino]-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2C(C=3C=CSC=3CC2)C)=C(C=CC=C2)C2=N1 WQHIUFKVRXWOIV-JWIMYKKASA-N 0.000 claims 1
• KMCOVAYCTWUHMM-XCZPVHLTSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-[(2s)-2-(5-methylpyridin-3-yl)pyrrolidin-1-yl]-2-oxoethoxy]quinoline-2-carbonyl]amino]-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2[C@@H](CCC2)C=2C=C(C)C=NC=2)=C(C=CC=C2)C2=N1 KMCOVAYCTWUHMM-XCZPVHLTSA-N 0.000 claims 1
• JSCCGNBSGGRWLE-RXVVDRJESA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-[(2s)-2-methyl-3-oxopiperazin-1-yl]-2-oxoethoxy]quinoline-2-carbonyl]amino]-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2[C@H](C(=O)NCC2)C)=C(C=CC=C2)C2=N1 JSCCGNBSGGRWLE-RXVVDRJESA-N 0.000 claims 1
• CBFDBLMRBKGWCG-IRLDBZIGSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-[(3r)-3-(hydroxymethyl)pyrrolidin-1-yl]-2-oxoethoxy]-7-methylquinoline-2-carbonyl]amino]-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2C[C@H](CO)CC2)=C(C=CC(C)=C2)C2=N1 CBFDBLMRBKGWCG-IRLDBZIGSA-N 0.000 claims 1
• CBFDBLMRBKGWCG-UNMCSNQZSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-[(3s)-3-(hydroxymethyl)pyrrolidin-1-yl]-2-oxoethoxy]-7-methylquinoline-2-carbonyl]amino]-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2C[C@@H](CO)CC2)=C(C=CC(C)=C2)C2=N1 CBFDBLMRBKGWCG-UNMCSNQZSA-N 0.000 claims 1
• RTLWCRFOOBIDDS-QODXOHEASA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-[2-(2-fluorophenyl)pyrrolidin-1-yl]-2-oxoethoxy]quinoline-2-carbonyl]amino]-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2C(CCC2)C=2C(=CC=CC=2)F)=C(C=CC=C2)C2=N1 RTLWCRFOOBIDDS-QODXOHEASA-N 0.000 claims 1
• CDTPDTWNWSCXHO-QODXOHEASA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-[2-(3-fluorophenyl)pyrrolidin-1-yl]-2-oxoethoxy]quinoline-2-carbonyl]amino]-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2C(CCC2)C=2C=C(F)C=CC=2)=C(C=CC=C2)C2=N1 CDTPDTWNWSCXHO-QODXOHEASA-N 0.000 claims 1
• YCLSLGLUVAOAGF-IAXKEJLGSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-[2-(hydroxymethyl)morpholin-4-yl]-2-oxoethoxy]-7-methylquinoline-2-carbonyl]amino]-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2CC(CO)OCC2)=C(C=CC(C)=C2)C2=N1 YCLSLGLUVAOAGF-IAXKEJLGSA-N 0.000 claims 1
• QGTKMBZFJYYQKJ-FHZUCYEKSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-[2-(methoxymethyl)piperidin-1-yl]-2-oxoethoxy]quinoline-2-carbonyl]amino]-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2C(CCCC2)COC)=C(C=CC=C2)C2=N1 QGTKMBZFJYYQKJ-FHZUCYEKSA-N 0.000 claims 1
• YYWWHLYIKLEEDQ-OZXSUGGESA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[7-ethyl-4-[2-[(2s)-2-(ethylcarbamoyl)pyrrolidin-1-yl]-2-oxoethoxy]quinoline-2-carbonyl]amino]-5-oxopentanoic acid Chemical compound CCNC(=O)[C@@H]1CCCN1C(=O)COC1=CC(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCN(CC2)C(=O)OCC)=NC2=CC(CC)=CC=C12 YYWWHLYIKLEEDQ-OZXSUGGESA-N 0.000 claims 1
• RKEMPOZEHLRMRV-DHLKQENFSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[7-fluoro-4-[2-oxo-2-[(2s)-2-(propylcarbamoyl)pyrrolidin-1-yl]ethoxy]quinoline-2-carbonyl]amino]-5-oxopentanoic acid Chemical compound CCCNC(=O)[C@@H]1CCCN1C(=O)COC1=CC(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCN(CC2)C(=O)OCC)=NC2=CC(F)=CC=C12 RKEMPOZEHLRMRV-DHLKQENFSA-N 0.000 claims 1
• KEOMFMNNZPCAND-IAXKEJLGSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[7-methyl-4-[2-(3-methylsulfonylpyrrolidin-1-yl)-2-oxoethoxy]quinoline-2-carbonyl]amino]-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2CC(CC2)S(C)(=O)=O)=C(C=CC(C)=C2)C2=N1 KEOMFMNNZPCAND-IAXKEJLGSA-N 0.000 claims 1
• JAGSCRDJOVKZTL-FQEVSTJZSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[7-methyl-4-[2-oxo-2-(2-oxopyrrolidin-1-yl)ethoxy]quinoline-2-carbonyl]amino]-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2C(CCC2)=O)=C(C=CC(C)=C2)C2=N1 JAGSCRDJOVKZTL-FQEVSTJZSA-N 0.000 claims 1
• UDGVEEXJOWTXQU-IBGZPJMESA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[7-methyl-4-[2-oxo-2-(3-oxopyrazolidin-1-yl)ethoxy]quinoline-2-carbonyl]amino]-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2NC(=O)CC2)=C(C=CC(C)=C2)C2=N1 UDGVEEXJOWTXQU-IBGZPJMESA-N 0.000 claims 1
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