AU2008241091B2 - Quinoline-carboxamide derivatives as P2Y12 antagonists - Google Patents
Quinoline-carboxamide derivatives as P2Y12 antagonists Download PDFInfo
- Publication number
- AU2008241091B2 AU2008241091B2 AU2008241091A AU2008241091A AU2008241091B2 AU 2008241091 B2 AU2008241091 B2 AU 2008241091B2 AU 2008241091 A AU2008241091 A AU 2008241091A AU 2008241091 A AU2008241091 A AU 2008241091A AU 2008241091 B2 AU2008241091 B2 AU 2008241091B2
- Authority
- AU
- Australia
- Prior art keywords
- oxo
- carboxylic acid
- alkylene
- quinoline
- piperazine
- 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.)
- Ceased
Links
- 239000005557 antagonist Substances 0.000 title claims description 13
- 102100026171 P2Y purinoceptor 12 Human genes 0.000 title description 19
- 101710192338 P2Y purinoceptor 12 Proteins 0.000 title description 16
- ZEXKKIXCRDTKBF-UHFFFAOYSA-N quinoline-2-carboxamide Chemical class C1=CC=CC2=NC(C(=O)N)=CC=C21 ZEXKKIXCRDTKBF-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 194
- -1 aza-bicyclohexane Chemical compound 0.000 claims description 526
- 125000000623 heterocyclic group Chemical group 0.000 claims description 117
- 125000000217 alkyl group Chemical group 0.000 claims description 111
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 108
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 99
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 81
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 77
- 229910052736 halogen Inorganic materials 0.000 claims description 76
- 150000002367 halogens Chemical class 0.000 claims description 73
- 125000003118 aryl group Chemical group 0.000 claims description 60
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 54
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 54
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 54
- 238000000034 method Methods 0.000 claims description 53
- 150000003839 salts Chemical class 0.000 claims description 52
- 229910052757 nitrogen Inorganic materials 0.000 claims description 50
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 48
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 47
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 46
- 238000006243 chemical reaction Methods 0.000 claims description 46
- 230000015572 biosynthetic process Effects 0.000 claims description 45
- 239000003112 inhibitor Substances 0.000 claims description 43
- 125000004076 pyridyl group Chemical group 0.000 claims description 39
- 125000002947 alkylene group Chemical group 0.000 claims description 38
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 37
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 37
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 35
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 34
- 239000002253 acid Substances 0.000 claims description 33
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 33
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 33
- 125000001544 thienyl group Chemical group 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 31
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 28
- 239000003795 chemical substances by application Substances 0.000 claims description 28
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 27
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 27
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 26
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 25
- 125000000335 thiazolyl group Chemical group 0.000 claims description 25
- UZHVXJZEHGSWQV-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydrocyclopenta[c]pyrrole Chemical compound C1NCC2CCCC21 UZHVXJZEHGSWQV-UHFFFAOYSA-N 0.000 claims description 24
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 24
- 208000007536 Thrombosis Diseases 0.000 claims description 24
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims description 24
- 125000004429 atom Chemical group 0.000 claims description 23
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 23
- 150000002148 esters Chemical class 0.000 claims description 23
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 23
- 125000003386 piperidinyl group Chemical group 0.000 claims description 23
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 22
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 22
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 22
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 22
- LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 claims description 21
- CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 claims description 21
- CZSRXHJVZUBEGW-UHFFFAOYSA-N 1,2-thiazolidine Chemical compound C1CNSC1 CZSRXHJVZUBEGW-UHFFFAOYSA-N 0.000 claims description 21
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 21
- POXWDTQUDZUOGP-UHFFFAOYSA-N 1h-1,4-diazepine Chemical compound N1C=CC=NC=C1 POXWDTQUDZUOGP-UHFFFAOYSA-N 0.000 claims description 21
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 claims description 21
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims description 21
- MSRJJSCOWHWGGX-UHFFFAOYSA-N 2h-1,3-diazepine Chemical compound C1N=CC=CC=N1 MSRJJSCOWHWGGX-UHFFFAOYSA-N 0.000 claims description 21
- KGWNRZLPXLBMPS-UHFFFAOYSA-N 2h-1,3-oxazine Chemical compound C1OC=CC=N1 KGWNRZLPXLBMPS-UHFFFAOYSA-N 0.000 claims description 21
- NTYABNDBNKVWOO-UHFFFAOYSA-N 2h-1,3-thiazine Chemical compound C1SC=CC=N1 NTYABNDBNKVWOO-UHFFFAOYSA-N 0.000 claims description 21
- YHWMFDLNZGIJSD-UHFFFAOYSA-N 2h-1,4-oxazine Chemical compound C1OC=CN=C1 YHWMFDLNZGIJSD-UHFFFAOYSA-N 0.000 claims description 21
- ZAISDHPZTZIFQF-UHFFFAOYSA-N 2h-1,4-thiazine Chemical compound C1SC=CN=C1 ZAISDHPZTZIFQF-UHFFFAOYSA-N 0.000 claims description 21
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 21
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 claims description 21
- BWCDLEQTELFBAW-UHFFFAOYSA-N 3h-dioxazole Chemical compound N1OOC=C1 BWCDLEQTELFBAW-UHFFFAOYSA-N 0.000 claims description 21
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims description 21
- GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical compound C1CC=NS1 GUUULVAMQJLDSY-UHFFFAOYSA-N 0.000 claims description 21
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 21
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 21
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 claims description 21
- JZFICWYCTCCINF-UHFFFAOYSA-N Thiadiazin Chemical compound S=C1SC(C)NC(C)N1CCN1C(=S)SC(C)NC1C JZFICWYCTCCINF-UHFFFAOYSA-N 0.000 claims description 21
- 125000002393 azetidinyl group Chemical group 0.000 claims description 21
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 21
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 21
- OXUZCBDDXOMZAM-UHFFFAOYSA-N oxathiepane Chemical compound C1CCOSCC1 OXUZCBDDXOMZAM-UHFFFAOYSA-N 0.000 claims description 21
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims description 21
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 21
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 21
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 claims description 21
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 21
- 150000003536 tetrazoles Chemical class 0.000 claims description 21
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 claims description 21
- ZNGWEEUXTBNKFR-UHFFFAOYSA-N 1,4-oxazepane Chemical compound C1CNCCOC1 ZNGWEEUXTBNKFR-UHFFFAOYSA-N 0.000 claims description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 20
- HTFFABIIOAKIBH-UHFFFAOYSA-N diazinane Chemical compound C1CCNNC1 HTFFABIIOAKIBH-UHFFFAOYSA-N 0.000 claims description 20
- 239000003814 drug Substances 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 125000000160 oxazolidinyl group Chemical group 0.000 claims description 19
- 125000003566 oxetanyl group Chemical group 0.000 claims description 19
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 19
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 19
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 19
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 18
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 18
- 125000002541 furyl group Chemical group 0.000 claims description 18
- 125000002757 morpholinyl group Chemical group 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 239000001301 oxygen Substances 0.000 claims description 18
- 239000011593 sulfur Substances 0.000 claims description 18
- IGERFAHWSHDDHX-UHFFFAOYSA-N 1,3-dioxanyl Chemical group [CH]1OCCCO1 IGERFAHWSHDDHX-UHFFFAOYSA-N 0.000 claims description 17
- JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 claims description 17
- 229910052794 bromium Inorganic materials 0.000 claims description 17
- IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims description 16
- 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 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 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 description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 15
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 15
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 125000002950 monocyclic group Chemical group 0.000 claims description 15
- 125000001624 naphthyl group Chemical group 0.000 claims description 15
- 238000001356 surgical procedure Methods 0.000 claims description 15
- 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 14
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 14
- BKWQKVJYXODDAC-UHFFFAOYSA-N 1,2-dihydropyridazine Chemical compound N1NC=CC=C1 BKWQKVJYXODDAC-UHFFFAOYSA-N 0.000 claims description 14
- LKLLNYWECKEQIB-UHFFFAOYSA-N 1,3,5-triazinane Chemical compound C1NCNCN1 LKLLNYWECKEQIB-UHFFFAOYSA-N 0.000 claims description 14
- ZBOWKDHBOFMERX-UHFFFAOYSA-N 1,3-diazepane Chemical compound C1CCNCNC1 ZBOWKDHBOFMERX-UHFFFAOYSA-N 0.000 claims description 14
- ABADUMLIAZCWJD-UHFFFAOYSA-N 1,3-dioxole Chemical compound C1OC=CO1 ABADUMLIAZCWJD-UHFFFAOYSA-N 0.000 claims description 14
- UUAVYXKRUSVCDJ-UHFFFAOYSA-N 1-cycloheptylazepane Chemical compound C1CCCCCC1N1CCCCCC1 UUAVYXKRUSVCDJ-UHFFFAOYSA-N 0.000 claims description 14
- LLSRLLPHUVVLQJ-UHFFFAOYSA-N 1-cycloheptyldiazepane Chemical compound C1CCCCCC1N1NCCCCC1 LLSRLLPHUVVLQJ-UHFFFAOYSA-N 0.000 claims description 14
- JWGMXWNVAYWSNI-UHFFFAOYSA-N 1-cyclohexyldiazinane Chemical compound C1CCCCC1N1NCCCC1 JWGMXWNVAYWSNI-UHFFFAOYSA-N 0.000 claims description 14
- BEWVAZNECYSPMT-UHFFFAOYSA-N 2,3-dihydro-1h-azepine Chemical compound C1CC=CC=CN1 BEWVAZNECYSPMT-UHFFFAOYSA-N 0.000 claims description 14
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 14
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 14
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 14
- SFJGCXYXEFWEBK-UHFFFAOYSA-N oxazepine Chemical compound O1C=CC=CC=N1 SFJGCXYXEFWEBK-UHFFFAOYSA-N 0.000 claims description 14
- 239000002243 precursor Substances 0.000 claims description 14
- 238000011321 prophylaxis Methods 0.000 claims description 14
- 238000002560 therapeutic procedure Methods 0.000 claims description 14
- 125000002053 thietanyl group Chemical group 0.000 claims description 14
- UOBKULMUFKXXEA-UHFFFAOYSA-N triazepane Chemical compound C1CCNNNC1 UOBKULMUFKXXEA-UHFFFAOYSA-N 0.000 claims description 14
- OQJVXNHMUWQQEW-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrazine Chemical compound C1CNC=CN1 OQJVXNHMUWQQEW-UHFFFAOYSA-N 0.000 claims description 13
- QQUFDFQHIUKUFP-UHFFFAOYSA-N 1-azaspiro[2.2]pentane Chemical compound C1CC11NC1 QQUFDFQHIUKUFP-UHFFFAOYSA-N 0.000 claims description 13
- HXNOEHIMWZDRTK-UHFFFAOYSA-N 4,5,6,7-tetrahydrothieno[2,3-c]pyridine Chemical compound C1NCCC2=C1SC=C2 HXNOEHIMWZDRTK-UHFFFAOYSA-N 0.000 claims description 13
- 239000000460 chlorine Substances 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 13
- 230000002792 vascular Effects 0.000 claims description 13
- 210000003462 vein Anatomy 0.000 claims description 13
- VWKKSBDTNICZRS-UHFFFAOYSA-N 1,2,4-triazinane Chemical compound C1CNNCN1 VWKKSBDTNICZRS-UHFFFAOYSA-N 0.000 claims description 12
- 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 12
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical group [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 claims description 12
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 12
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 12
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- POTIYWUALSJREP-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroquinoline Chemical compound N1CCCC2CCCCC21 POTIYWUALSJREP-UHFFFAOYSA-N 0.000 claims description 11
- QMWYDZLBWGJQOY-UHFFFAOYSA-N 1,3,8-triazaspiro[4.5]decane Chemical compound N1CNCC11CCNCC1 QMWYDZLBWGJQOY-UHFFFAOYSA-N 0.000 claims description 11
- QUIJMHDIAFOPRK-UHFFFAOYSA-N 1-cyclooctylazocane Chemical compound C1CCCCCCC1N1CCCCCCC1 QUIJMHDIAFOPRK-UHFFFAOYSA-N 0.000 claims description 11
- PDELQDSYLBLPQO-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-indole Chemical compound C1CCCC2NCCC21 PDELQDSYLBLPQO-UHFFFAOYSA-N 0.000 claims description 11
- SCEIUGQQBYRBPP-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-azepine Chemical compound C1CCC=CNC1 SCEIUGQQBYRBPP-UHFFFAOYSA-N 0.000 claims description 11
- UKHJNJFJCGBKSF-UHFFFAOYSA-N 2,5-diazabicyclo[2.2.1]heptane Chemical compound C1NC2CNC1C2 UKHJNJFJCGBKSF-UHFFFAOYSA-N 0.000 claims description 11
- WYZZNMWIWHRXRM-UHFFFAOYSA-N 2,8-diazaspiro[4.5]decane Chemical compound C1NCCC21CCNCC2 WYZZNMWIWHRXRM-UHFFFAOYSA-N 0.000 claims description 11
- 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 11
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims description 11
- 239000003146 anticoagulant agent Substances 0.000 claims description 11
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 11
- 125000004193 piperazinyl group Chemical group 0.000 claims description 11
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 11
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 10
- FTUSZJTUFHXUPG-UHFFFAOYSA-N 1,2,3,3a,4,5-hexahydropyrrolo[2,3-c]pyrrole Chemical compound C1NC=C2NCCC21 FTUSZJTUFHXUPG-UHFFFAOYSA-N 0.000 claims description 10
- 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 10
- BFFIACPYUHJBDJ-UHFFFAOYSA-N 4,5,6,7-tetrahydro-[1,2]oxazolo[5,4-c]pyridine Chemical compound C1NCCC2=C1ON=C2 BFFIACPYUHJBDJ-UHFFFAOYSA-N 0.000 claims description 10
- UMEIYBJBGZKZOS-UHFFFAOYSA-N 5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a]pyrazine Chemical compound C1NCCN2C=NN=C21 UMEIYBJBGZKZOS-UHFFFAOYSA-N 0.000 claims description 10
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 10
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- XDIQAUUEADQJGW-NRFANRHFSA-N (4s)-4-[[4-[2-(2,4-dioxo-1,3,8-triazaspiro[4.5]decan-8-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)N2CCC3(CC2)C(NC(=O)N3)=O)=C(C=CC=C2)C2=N1 XDIQAUUEADQJGW-NRFANRHFSA-N 0.000 claims 1
- IDAKBQHMRQBVDL-AKRCKQFNSA-N (4s)-4-[[4-[2-(3-acetamidopyrrolidin-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(C)=O)=C(C=CC=C2)C2=N1 IDAKBQHMRQBVDL-AKRCKQFNSA-N 0.000 claims 1
- NDKWKNXODIKNRU-NRFANRHFSA-N (4s)-4-[[4-[2-(4,4-difluoropiperidin-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)N2CCC(F)(F)CC2)=C(C=CC=C2)C2=N1 NDKWKNXODIKNRU-NRFANRHFSA-N 0.000 claims 1
- ZWWTZPNSAVBXIC-NRFANRHFSA-N (4s)-4-[[4-[2-(4,4-dimethyl-1,3-oxazolidin-3-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(COC2)(C)C)=C(C=CC=C2)C2=N1 ZWWTZPNSAVBXIC-NRFANRHFSA-N 0.000 claims 1
- LMGHGKKRHGIHHI-XEBLAHISSA-N (4s)-4-[[4-[2-(6-ethoxycarbonyl-3-azabicyclo[3.1.0]hexan-3-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)N1CC2C(C2C1)C(=O)OCC)N1CCN(C(=O)OCC)CC1 LMGHGKKRHGIHHI-XEBLAHISSA-N 0.000 claims 1
- QWTRIGZHEZSJTM-UKILVPOCSA-N (4s)-4-[[4-[2-[(2r)-2-(cyclopropylcarbamoyl)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)N2[C@H](CCC2)C(=O)NC2CC2)=C(C=CC=C2)C2=N1 QWTRIGZHEZSJTM-UKILVPOCSA-N 0.000 claims 1
- BUHZSFLIKHNJNH-RBBKRZOGSA-N (4s)-4-[[4-[2-[(2r)-2-carbamoylpyrrolidin-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)=O)=C(C=CC=C2)C2=N1 BUHZSFLIKHNJNH-RBBKRZOGSA-N 0.000 claims 1
- PCZSPQLYXNTLJU-KNQAVFIVSA-N (4s)-4-[[4-[2-[(2r)-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-KNQAVFIVSA-N 0.000 claims 1
- ISGBGWFYLKOGAR-UPVQGACJSA-N (4s)-4-[[4-[2-[(2s)-2-(cyclobutylcarbamoyl)azetidin-1-yl]-2-oxoethoxy]-5-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(F)=CC=C2)C2=N1 ISGBGWFYLKOGAR-UPVQGACJSA-N 0.000 claims 1
- NVBCSDHRQNNESS-ZCYQVOJMSA-N (4s)-4-[[4-[2-[(2s)-2-(cyclobutylcarbamoyl)pyrrolidin-1-yl]-2-oxoethoxy]-5-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](CCC2)C(=O)NC2CCC2)=C(C(F)=CC=C2)C2=N1 NVBCSDHRQNNESS-ZCYQVOJMSA-N 0.000 claims 1
- GOLKNVMEHQAXJU-XCZPVHLTSA-N (4s)-4-[[4-[2-[(2s)-2-(cyclobutylcarbamoyl)pyrrolidin-1-yl]-2-oxoethoxy]-6-ethoxyquinoline-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(OCC)C=C2)C2=N1 GOLKNVMEHQAXJU-XCZPVHLTSA-N 0.000 claims 1
- GVNXSXHGRBCGSM-AHWVRZQESA-N (4s)-4-[[4-[2-[(2s)-2-(cyclobutylcarbamoyl)pyrrolidin-1-yl]-2-oxoethoxy]-6-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](CCC2)C(=O)NC2CCC2)=C(C=C(F)C=C2)C2=N1 GVNXSXHGRBCGSM-AHWVRZQESA-N 0.000 claims 1
- KVMUNAHYOZIYAO-OZXSUGGESA-N (4s)-4-[[4-[2-[(2s)-2-(cyclobutylcarbamoyl)pyrrolidin-1-yl]-2-oxoethoxy]-7-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](CCC2)C(=O)NC2CCC2)=C(C=CC(F)=C2)C2=N1 KVMUNAHYOZIYAO-OZXSUGGESA-N 0.000 claims 1
- DJHDSZCQRXUVML-IGKIAQTJSA-N (4s)-4-[[4-[2-[(2s)-2-(cyclobutylcarbamoyl)pyrrolidin-1-yl]-2-oxoethoxy]-7-methoxyquinoline-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=CC(OC)=C2)C2=N1 DJHDSZCQRXUVML-IGKIAQTJSA-N 0.000 claims 1
- TUOKTRFZGQCHJM-ZCYQVOJMSA-N (4s)-4-[[4-[2-[(2s)-2-(cyclobutylcarbamoyl)pyrrolidin-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](CCC2)C(=O)NC2CCC2)=C(C=CC=C2F)C2=N1 TUOKTRFZGQCHJM-ZCYQVOJMSA-N 0.000 claims 1
- QWJCYPMQQXRNIQ-AHWVRZQESA-N (4s)-4-[[4-[2-[(2s)-2-(cyclopropylcarbamoyl)piperidin-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](CCCC2)C(=O)NC2CC2)=C(C=CC=C2)C2=N1 QWJCYPMQQXRNIQ-AHWVRZQESA-N 0.000 claims 1
- XJLZOFFMDVCWHS-UPVQGACJSA-N (4s)-4-[[4-[2-[(2s)-2-(cyclopropylcarbamoyl)pyrrolidin-1-yl]-2-oxoethoxy]-5-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](CCC2)C(=O)NC2CC2)=C(C(F)=CC=C2)C2=N1 XJLZOFFMDVCWHS-UPVQGACJSA-N 0.000 claims 1
- CFWNWQFMDZEICH-ZCYQVOJMSA-N (4s)-4-[[4-[2-[(2s)-2-(cyclopropylcarbamoyl)pyrrolidin-1-yl]-2-oxoethoxy]-5-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)NC2CC2)=C(C(C)=CC=C2)C2=N1 CFWNWQFMDZEICH-ZCYQVOJMSA-N 0.000 claims 1
- SLGIRMNDRINGOT-BDYUSTAISA-N (4s)-4-[[4-[2-[(2s)-2-(cyclopropylcarbamoyl)pyrrolidin-1-yl]-2-oxoethoxy]-6-ethoxyquinoline-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=C(OCC)C=C2)C2=N1 SLGIRMNDRINGOT-BDYUSTAISA-N 0.000 claims 1
- PEVUZHQQADHQEF-ZCYQVOJMSA-N (4s)-4-[[4-[2-[(2s)-2-(cyclopropylcarbamoyl)pyrrolidin-1-yl]-2-oxoethoxy]-6-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](CCC2)C(=O)NC2CC2)=C(C=C(F)C=C2)C2=N1 PEVUZHQQADHQEF-ZCYQVOJMSA-N 0.000 claims 1
- UULPBIVEANDVLT-AHWVRZQESA-N (4s)-4-[[4-[2-[(2s)-2-(cyclopropylcarbamoyl)pyrrolidin-1-yl]-2-oxoethoxy]-6-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)NC2CC2)=C(C=C(C)C=C2)C2=N1 UULPBIVEANDVLT-AHWVRZQESA-N 0.000 claims 1
- JXCDZEGIKZWBAS-UPVQGACJSA-N (4s)-4-[[4-[2-[(2s)-2-(cyclopropylcarbamoyl)pyrrolidin-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](CCC2)C(=O)NC2CC2)=C(C=CC=C2F)C2=N1 JXCDZEGIKZWBAS-UPVQGACJSA-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
- QWTRIGZHEZSJTM-ZCYQVOJMSA-N (4s)-4-[[4-[2-[(2s)-2-(cyclopropylcarbamoyl)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)N2[C@@H](CCC2)C(=O)NC2CC2)=C(C=CC=C2)C2=N1 QWTRIGZHEZSJTM-ZCYQVOJMSA-N 0.000 claims 1
- AASPONPONQMDEK-UPVQGACJSA-N (4s)-4-[[4-[2-[(2s)-2-(dimethylcarbamoyl)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)N2[C@@H](CCC2)C(=O)N(C)C)=C(C=CC=C2)C2=N1 AASPONPONQMDEK-UPVQGACJSA-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
- UVCDGAJHHOUUDW-KJWPAHLWSA-N (4s)-4-[[4-[2-[(2s,4r)-2-ethoxycarbonyl-4-hydroxypyrrolidin-1-yl]-2-oxoethoxy]-7-methylquinoline-2-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound CCOC(=O)[C@@H]1C[C@@H](O)CN1C(=O)COC1=CC(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCN(CC2)C(=O)OCC)=NC2=CC(C)=CC=C12 UVCDGAJHHOUUDW-KJWPAHLWSA-N 0.000 claims 1
- CRKSPAUKYIMAMA-UCFCWBNQSA-N (4s)-4-[[4-[2-[(2s,4r)-2-ethoxycarbonyl-4-hydroxypyrrolidin-1-yl]-2-oxoethoxy]quinoline-2-carbonyl]amino]-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxopentanoic acid Chemical compound CCOC(=O)[C@@H]1C[C@@H](O)CN1C(=O)COC1=CC(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCN(CC2)C(=O)OCC)=NC2=CC=CC=C12 CRKSPAUKYIMAMA-UCFCWBNQSA-N 0.000 claims 1
- BBGZHTRDYCYIFN-YKSBVNFPSA-N (4s)-4-[[4-[2-[(3r)-3-(cyclopropylcarbamoyl)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[C@@H](CC2)C(=O)NC2CC2)=C(C=CC=C2)C2=N1 BBGZHTRDYCYIFN-YKSBVNFPSA-N 0.000 claims 1
- BBGZHTRDYCYIFN-RDPSFJRHSA-N (4s)-4-[[4-[2-[(3s)-3-(cyclopropylcarbamoyl)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[C@H](CC2)C(=O)NC2CC2)=C(C=CC=C2)C2=N1 BBGZHTRDYCYIFN-RDPSFJRHSA-N 0.000 claims 1
- PEDZAFWAPUAMSC-VJBMBRPKSA-N (4s)-4-[[4-[2-[(3s,4s)-3,4-dihydroxypyrrolidin-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](O)[C@@H](O)C2)=C(C=CC(C)=C2)C2=N1 PEDZAFWAPUAMSC-VJBMBRPKSA-N 0.000 claims 1
- NJQSBHBPWHLNRT-BVSLBCMMSA-N (4s)-4-[[4-[2-[(3s,4s)-3,4-dihydroxypyrrolidin-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[C@H](O)[C@@H](O)C2)=C(C=CC=C2)C2=N1 NJQSBHBPWHLNRT-BVSLBCMMSA-N 0.000 claims 1
- AIGUHNCJOSHREQ-QODXOHEASA-N (4s)-4-[[4-[2-[2-(2-chlorophenyl)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=CC=2)Cl)=C(C=CC=C2)C2=N1 AIGUHNCJOSHREQ-QODXOHEASA-N 0.000 claims 1
- GMFRNQBAVURUGE-MBCWZBCWSA-N (4s)-4-[[4-[2-[2-(3,4-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=C(C)C(C)=CC=2)=C(C=CC=C2)C2=N1 GMFRNQBAVURUGE-MBCWZBCWSA-N 0.000 claims 1
- LZFMYRVCOBTGKF-QODXOHEASA-N (4s)-4-[[4-[2-[2-(3-chlorophenyl)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=C(Cl)C=CC=2)=C(C=CC=C2)C2=N1 LZFMYRVCOBTGKF-QODXOHEASA-N 0.000 claims 1
- OGLIHWSOSRCEQN-PVCWFJFTSA-N (4s)-4-[[4-[2-[2-(5-bromopyridin-3-yl)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=C(Br)C=NC=2)=C(C=CC=C2)C2=N1 OGLIHWSOSRCEQN-PVCWFJFTSA-N 0.000 claims 1
- DLBQUTLIDWHADS-QHCPKHFHSA-N (4s)-4-[[4-[2-[3-(cyclopropylcarbamoyl)azetidin-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(C2)C(=O)NC2CC2)=C(C=CC=C2)C2=N1 DLBQUTLIDWHADS-QHCPKHFHSA-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
- FHQHXCZPTNMDDB-QFIPXVFZSA-N (4s)-4-[[4-[2-[4-(carboxymethyl)piperazin-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)N2CCN(CC(O)=O)CC2)=C(C=CC=C2)C2=N1 FHQHXCZPTNMDDB-QFIPXVFZSA-N 0.000 claims 1
- VGFIWKGTJRPHAU-VWLOTQADSA-N (4s)-4-[[4-[2-[4-(cyclopropylcarbamoyl)piperidin-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)N2CCC(CC2)C(=O)NC2CC2)=C(C=CC(C)=C2)C2=N1 VGFIWKGTJRPHAU-VWLOTQADSA-N 0.000 claims 1
- BXFSYUJHTGHISH-VWLOTQADSA-N (4s)-4-[[4-[2-[4-(cyclopropylcarbamoyl)piperidin-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)N2CCC(CC2)C(=O)NC2CC2)=C(C=CC=C2)C2=N1 BXFSYUJHTGHISH-VWLOTQADSA-N 0.000 claims 1
- NGOPFUDJOXHSMN-ZCYQVOJMSA-N (4s)-4-[[6-chloro-4-[2-[(2s)-2-(cyclopropylcarbamoyl)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)N2[C@@H](CCC2)C(=O)NC2CC2)=C(C=C(Cl)C=C2)C2=N1 NGOPFUDJOXHSMN-ZCYQVOJMSA-N 0.000 claims 1
- QQGVXMZVCBOBCV-NPHAVVRNSA-N (4s)-5-(4-butoxycarbonylpiperazin-1-yl)-4-[[4-[2-[2-(2,4-difluorophenyl)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)N2C(CCC2)C=2C(=CC(F)=CC=2)F)=C(C=CC(C)=C2)C2=N1 QQGVXMZVCBOBCV-NPHAVVRNSA-N 0.000 claims 1
- IZHUODXODWEHRA-NPHAVVRNSA-N (4s)-5-(4-butoxycarbonylpiperazin-1-yl)-4-[[4-[2-[2-(3,4-difluorophenyl)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)N2C(CCC2)C=2C=C(F)C(F)=CC=2)=C(C=CC(C)=C2)C2=N1 IZHUODXODWEHRA-NPHAVVRNSA-N 0.000 claims 1
- BLQIJVSGESUCSQ-ALLRNTDFSA-N (4s)-5-(4-butoxycarbonylpiperazin-1-yl)-4-[[4-[2-[2-(furan-2-yl)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)N2C(CCC2)C=2OC=CC=2)=C(C=CC(C)=C2)C2=N1 BLQIJVSGESUCSQ-ALLRNTDFSA-N 0.000 claims 1
- GZCUMNHNMDUKJN-USNNOTDGSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-(2-methoxycarbonylaziridine-1-carbonyl)quinoline-2-carbonyl]amino]-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(C(=O)N2C(C2)C(=O)OC)=C(C=CC=C2)C2=N1 GZCUMNHNMDUKJN-USNNOTDGSA-N 0.000 claims 1
- RKBIXLJZZPAXEX-NRFANRHFSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-(2-morpholin-4-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)N2CCOCC2)=C(C=CC=C2)C2=N1 RKBIXLJZZPAXEX-NRFANRHFSA-N 0.000 claims 1
- SDNYNPKQVFIRLN-FQEVSTJZSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-(3-hydroxyazetidine-1-carbonyl)quinoline-2-carbonyl]amino]-5-oxopentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(C(=O)N2CC(O)C2)=C(C=CC=C2)C2=N1 SDNYNPKQVFIRLN-FQEVSTJZSA-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
- ZMTAGYCPHPZQNX-IAXKEJLGSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-(3-hydroxypiperidin-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)N2CC(O)CCC2)=C(C=CC(C)=C2)C2=N1 ZMTAGYCPHPZQNX-IAXKEJLGSA-N 0.000 claims 1
- GXAPIEDXMPNVQU-BPARTEKVSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-(3-hydroxypiperidin-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(O)CCC2)=C(C=CC=C2)C2=N1 GXAPIEDXMPNVQU-BPARTEKVSA-N 0.000 claims 1
- PQBFJMOVWNCKEN-MMPATGFWSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-(3-methoxy-3a,4,6,6a-tetrahydropyrrolo[3,4-d][1,2]oxazol-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)N2CC3C(OC)=NOC3C2)=C(C=CC=C2)C2=N1 PQBFJMOVWNCKEN-MMPATGFWSA-N 0.000 claims 1
- UTRMDGOVMOMJLK-BPARTEKVSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-(3-methoxypyrrolidin-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)OC)=C(C=CC=C2)C2=N1 UTRMDGOVMOMJLK-BPARTEKVSA-N 0.000 claims 1
- WZAIAXFGYNHPLH-DEOSSOPVSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-(4-ethoxycarbonylpiperidin-1-yl)-2-oxoethoxy]-7-methylquinoline-2-carbonyl]amino]-5-oxopentanoic acid Chemical compound C1CC(C(=O)OCC)CCN1C(=O)COC1=CC(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCN(CC2)C(=O)OCC)=NC2=CC(C)=CC=C12 WZAIAXFGYNHPLH-DEOSSOPVSA-N 0.000 claims 1
- DXPPVHCOPNYOQS-DEOSSOPVSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-(4-ethoxycarbonylpiperidin-1-yl)-2-oxoethoxy]quinoline-2-carbonyl]amino]-5-oxopentanoic acid Chemical compound C1CC(C(=O)OCC)CCN1C(=O)COC1=CC(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCN(CC2)C(=O)OCC)=NC2=CC=CC=C12 DXPPVHCOPNYOQS-DEOSSOPVSA-N 0.000 claims 1
- BWUVPMMVVNBLDR-DEOSSOPVSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-(4-ethoxypiperidin-1-yl)-2-oxoethoxy]quinoline-2-carbonyl]amino]-5-oxopentanoic acid Chemical compound C1CC(OCC)CCN1C(=O)COC1=CC(C(=O)N[C@@H](CCC(O)=O)C(=O)N2CCN(CC2)C(=O)OCC)=NC2=CC=CC=C12 BWUVPMMVVNBLDR-DEOSSOPVSA-N 0.000 claims 1
- RAMPGIQQFUWTQW-STDCAVTESA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-(4-hydroxy-2-methoxycarbonylpyrrolidin-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(CC(O)C2)C(=O)OC)=C(C=CC=C2)C2=N1 RAMPGIQQFUWTQW-STDCAVTESA-N 0.000 claims 1
- QVNZRCSSZLFATB-QFIPXVFZSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-(4-hydroxypiperidin-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)N2CCC(O)CC2)=C(C=CC=C2)C2=N1 QVNZRCSSZLFATB-QFIPXVFZSA-N 0.000 claims 1
- HXHKMYHEAIUEGP-QHCPKHFHSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-(4-methoxypiperidin-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)N2CCC(CC2)OC)=C(C=CC=C2)C2=N1 HXHKMYHEAIUEGP-QHCPKHFHSA-N 0.000 claims 1
- RJHUEPDDEYMIAK-UHFKCPIBSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-(4-methyl-3-oxo-2-propan-2-ylpiperazin-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)N(C)CC2)C(C)C)=C(C=CC=C2)C2=N1 RJHUEPDDEYMIAK-UHFKCPIBSA-N 0.000 claims 1
- DWRSQAWQEKNQSC-NRFANRHFSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-(4-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)N2CC(=O)N(C)CC2)=C(C=CC=C2)C2=N1 DWRSQAWQEKNQSC-NRFANRHFSA-N 0.000 claims 1
- IGWCYTNFIYODHC-OZBJMMHXSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-(5-methyl-3-oxopyrazolidin-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(CC(=O)N2)C)=C(C=CC=C2)C2=N1 IGWCYTNFIYODHC-OZBJMMHXSA-N 0.000 claims 1
- QKUFGJJRHAPFQK-SANMLTNESA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-(6-methoxy-3,4-dihydro-2h-quinolin-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=C(OC)C=C3CCC2)=C(C=CC=C2)C2=N1 QKUFGJJRHAPFQK-SANMLTNESA-N 0.000 claims 1
- BHYMXAYECQDJGD-DOXRDRLYSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-(6-methyl-3,4,4a,5,7,7a-hexahydro-2h-pyrrolo[3,4-b]pyridin-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)N2C3CN(C)CC3CCC2)=C(C=CC=C2)C2=N1 BHYMXAYECQDJGD-DOXRDRLYSA-N 0.000 claims 1
- HFWANRYEAWOFHX-KNQAVFIVSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-[(2r)-2-(hydroxymethyl)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)CO)=C(C=CC=C2)C2=N1 HFWANRYEAWOFHX-KNQAVFIVSA-N 0.000 claims 1
- XZCVFSPPVIKFTL-LADGPHEKSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-[(2r)-2-ethoxycarbonylpyrrolidin-1-yl]-2-oxoethoxy]quinoline-2-carbonyl]amino]-5-oxopentanoic acid Chemical compound CCOC(=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=C12 XZCVFSPPVIKFTL-LADGPHEKSA-N 0.000 claims 1
- BJGWGFRBMCBWIB-UPVQGACJSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-[(2s)-2-(2-fluoroethylcarbamoyl)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(=O)NCCF)=C(C=CC=C2)C2=N1 BJGWGFRBMCBWIB-UPVQGACJSA-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
- JEIWAJKPJSIZFF-GMAHTHKFSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-[(2s)-2-(ethylcarbamoyl)pyrrolidin-1-yl]-2-oxoethoxy]-5-fluoroquinoline-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(F)=C12 JEIWAJKPJSIZFF-GMAHTHKFSA-N 0.000 claims 1
- JTYZOWIYSNXUOU-UPVQGACJSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-[(2s)-2-(ethylcarbamoyl)pyrrolidin-1-yl]-2-oxoethoxy]-6-fluoro-5-methylquinoline-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=C(F)C(C)=C12 JTYZOWIYSNXUOU-UPVQGACJSA-N 0.000 claims 1
- ZZZMRPHRIATFQJ-DHLKQENFSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-[(2s)-2-(ethylcarbamoyl)pyrrolidin-1-yl]-2-oxoethoxy]-7-methoxyquinoline-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(OC)=CC=C12 ZZZMRPHRIATFQJ-DHLKQENFSA-N 0.000 claims 1
- FFVZDDKFAQXNMN-GMAHTHKFSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-[(2s)-2-(ethylcarbamoyl)pyrrolidin-1-yl]-2-oxoethoxy]-8-fluoroquinoline-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=C(F)C=CC=C12 FFVZDDKFAQXNMN-GMAHTHKFSA-N 0.000 claims 1
- HFWANRYEAWOFHX-UGKGYDQZSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-[(2s)-2-(hydroxymethyl)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)CO)=C(C=CC=C2)C2=N1 HFWANRYEAWOFHX-UGKGYDQZSA-N 0.000 claims 1
- SBDAGTYEQBSEQG-GMAHTHKFSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-[(2s)-2-(methoxymethyl)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)N2[C@@H](CCC2)COC)=C(C=CC(C)=C2)C2=N1 SBDAGTYEQBSEQG-GMAHTHKFSA-N 0.000 claims 1
- AMAUPAVBZBJGFI-REWPJTCUSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-[(2s)-2-(methoxymethyl)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)COC)=C(C=CC=C2)C2=N1 AMAUPAVBZBJGFI-REWPJTCUSA-N 0.000 claims 1
- KYKKKLHCXPCSFC-HARLFGEKSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-[(2s,4s)-4-fluoro-2-methoxycarbonylpyrrolidin-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[C@H](F)C2)C(=O)OC)=C(C=CC=C2)C2=N1 KYKKKLHCXPCSFC-HARLFGEKSA-N 0.000 claims 1
- RAMPGIQQFUWTQW-HARLFGEKSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-[(2s,4s)-4-hydroxy-2-methoxycarbonylpyrrolidin-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[C@H](O)C2)C(=O)OC)=C(C=CC=C2)C2=N1 RAMPGIQQFUWTQW-HARLFGEKSA-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
- ZMTAGYCPHPZQNX-IRLDBZIGSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-[(3r)-3-hydroxypiperidin-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](O)CCC2)=C(C=CC(C)=C2)C2=N1 ZMTAGYCPHPZQNX-IRLDBZIGSA-N 0.000 claims 1
- GXAPIEDXMPNVQU-KNQAVFIVSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-[(3r)-3-hydroxypiperidin-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@H](O)CCC2)=C(C=CC=C2)C2=N1 GXAPIEDXMPNVQU-KNQAVFIVSA-N 0.000 claims 1
- YDWFPMIWIBXWOV-NQIIRXRSSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-[(3r)-3-hydroxypyrrolidin-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@H](O)CC2)=C(C=CC=C2)C2=N1 YDWFPMIWIBXWOV-NQIIRXRSSA-N 0.000 claims 1
- CENCAGJTLXTQJE-IGKIAQTJSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-[(3s)-3-(hydroxymethyl)-3,4-dihydro-1h-isoquinolin-2-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](CC3=CC=CC=C3C2)CO)=C(C=CC=C2)C2=N1 CENCAGJTLXTQJE-IGKIAQTJSA-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
- AQWAJOOHEMIWLB-UGKGYDQZSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-[(3s)-3-(hydroxymethyl)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[C@@H](CO)CC2)=C(C=CC=C2)C2=N1 AQWAJOOHEMIWLB-UGKGYDQZSA-N 0.000 claims 1
- RXVKFOCADWCSBX-FPOVZHCZSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-[(3s)-3-hydroxy-2-oxopyrrolidin-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@@H](O)CC2)=O)=C(C=CC=C2)C2=N1 RXVKFOCADWCSBX-FPOVZHCZSA-N 0.000 claims 1
- XTQSDTAACVCOBU-TUXUZCGSSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-[2-(hydroxymethyl)-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=C3CC2CO)=C(C=CC=C2)C2=N1 XTQSDTAACVCOBU-TUXUZCGSSA-N 0.000 claims 1
- OHPFUAXWQSSFRB-BPARTEKVSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-[2-(hydroxymethyl)morpholin-4-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(CO)OCC2)=C(C=CC=C2)C2=N1 OHPFUAXWQSSFRB-BPARTEKVSA-N 0.000 claims 1
- ZOLSYRXFJRLWBF-AKRCKQFNSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-[2-(methylsulfanylmethyl)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)CSC)=C(C=CC=C2)C2=N1 ZOLSYRXFJRLWBF-AKRCKQFNSA-N 0.000 claims 1
- WTAOGPTWPHBRLU-NASUQTAISA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-[2-(morpholin-4-ylmethyl)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)CN2CCOCC2)=C(C=CC=C2)C2=N1 WTAOGPTWPHBRLU-NASUQTAISA-N 0.000 claims 1
- LSJUVQKIFWUBOG-ZUILJJEPSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-[3-(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)N2CC(CC2)C=2C(=CC=CC=2)F)=C(C=CC=C2)C2=N1 LSJUVQKIFWUBOG-ZUILJJEPSA-N 0.000 claims 1
- ZTDSIJVLXLCJGC-QFIPXVFZSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-[3-(2-methoxy-2-oxoethyl)sulfonylazetidin-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(C2)S(=O)(=O)CC(=O)OC)=C(C=CC=C2)C2=N1 ZTDSIJVLXLCJGC-QFIPXVFZSA-N 0.000 claims 1
- DTNNFSHOTBCFKT-WKDCXCOVSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-[3-(2-methylphenoxy)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)N2CC(CC2)OC=2C(=CC=CC=2)C)=C(C=CC=C2)C2=N1 DTNNFSHOTBCFKT-WKDCXCOVSA-N 0.000 claims 1
- PENLQDPUUBVVBS-SANMLTNESA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[4-[2-[4-(2-morpholin-4-yl-2-oxoethyl)piperazin-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)N2CCN(CC(=O)N3CCOCC3)CC2)=C(C=CC=C2)C2=N1 PENLQDPUUBVVBS-SANMLTNESA-N 0.000 claims 1
- ASJWOLHLQJLZJZ-NRFANRHFSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[5-fluoro-4-[2-(4-hydroxypiperidin-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)N2CCC(O)CC2)=C(C(F)=CC=C2)C2=N1 ASJWOLHLQJLZJZ-NRFANRHFSA-N 0.000 claims 1
- UJSNJWAYMVNUII-AHWVRZQESA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[6-ethoxy-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=C(OCC)C=C12 UJSNJWAYMVNUII-AHWVRZQESA-N 0.000 claims 1
- SFYDWFACVKTMQJ-QFIPXVFZSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[6-fluoro-4-[2-(4-hydroxypiperidin-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)N2CCC(O)CC2)=C(C=C(F)C=C2)C2=N1 SFYDWFACVKTMQJ-QFIPXVFZSA-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
- LMYXUFGVLMUATI-NRFANRHFSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[7-fluoro-4-[2-(4-hydroxypiperidin-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)N2CCC(O)CC2)=C(C=CC(F)=C2)C2=N1 LMYXUFGVLMUATI-NRFANRHFSA-N 0.000 claims 1
- UQAITOKJMPKOLW-NRFANRHFSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[7-methyl-4-(2-morpholin-4-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)N2CCOCC2)=C(C=CC(C)=C2)C2=N1 UQAITOKJMPKOLW-NRFANRHFSA-N 0.000 claims 1
- TZIZSKJWOTZMAA-IBGZPJMESA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[7-methyl-4-[2-oxo-2-(2-oxo-1,3-oxazolidin-3-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(OCC2)=O)=C(C=CC(C)=C2)C2=N1 TZIZSKJWOTZMAA-IBGZPJMESA-N 0.000 claims 1
- FVPYRZPAICWIGK-NRFANRHFSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[7-methyl-4-[2-oxo-2-(5-oxo-1,4-diazepan-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)N2CCC(=O)NCC2)=C(C=CC(C)=C2)C2=N1 FVPYRZPAICWIGK-NRFANRHFSA-N 0.000 claims 1
- SHGPJCRQXUNPSA-LSYYVWMOSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[7-methyl-4-[2-oxo-2-[(2s)-2-(piperidine-1-carbonyl)pyrrolidin-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)N2[C@@H](CCC2)C(=O)N2CCCCC2)=C(C=CC(C)=C2)C2=N1 SHGPJCRQXUNPSA-LSYYVWMOSA-N 0.000 claims 1
- WBORKYOPOZSQQB-IGKIAQTJSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[7-methyl-4-[2-oxo-2-[(2s)-2-(pyrrolidine-1-carbonyl)pyrrolidin-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)N2[C@@H](CCC2)C(=O)N2CCCC2)=C(C=CC(C)=C2)C2=N1 WBORKYOPOZSQQB-IGKIAQTJSA-N 0.000 claims 1
- YJYMCQCOIMVVBC-NRFANRHFSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-4-[[8-fluoro-4-[2-(4-hydroxypiperidin-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)N2CCC(O)CC2)=C(C=CC=C2F)C2=N1 YJYMCQCOIMVVBC-NRFANRHFSA-N 0.000 claims 1
- KAQZCXSVMDQYSI-SANMLTNESA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxo-4-[[4-[2-oxo-2-(3-oxo-4-phenylpiperazin-1-yl)ethoxy]quinoline-2-carbonyl]amino]pentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2CC(=O)N(CC2)C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 KAQZCXSVMDQYSI-SANMLTNESA-N 0.000 claims 1
- IKMUCSMEEIIXPV-IBGZPJMESA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxo-4-[[4-[2-oxo-2-(3-oxopyrazolidin-1-yl)ethoxy]quinoline-2-carbonyl]amino]pentanoic 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=C2)C2=N1 IKMUCSMEEIIXPV-IBGZPJMESA-N 0.000 claims 1
- NBWBLSJRISBSTH-NRFANRHFSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxo-4-[[4-[2-oxo-2-(3-oxopyrrolidin-1-yl)ethoxy]quinoline-2-carbonyl]amino]pentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2CC(=O)CC2)=C(C=CC=C2)C2=N1 NBWBLSJRISBSTH-NRFANRHFSA-N 0.000 claims 1
- HKCUWLBXOQEZIG-MHZLTWQESA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxo-4-[[4-[2-oxo-2-(3-phenyl-6,7-dihydro-4h-[1,2]oxazolo[4,5-c]pyridin-5-yl)ethoxy]quinoline-2-carbonyl]amino]pentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2CC=3C(=NOC=3CC2)C=2C=CC=CC=2)=C(C=CC=C2)C2=N1 HKCUWLBXOQEZIG-MHZLTWQESA-N 0.000 claims 1
- CBCVKKKQXQLQBX-VWLOTQADSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxo-4-[[4-[2-oxo-2-(4-propan-2-yloxypiperidin-1-yl)ethoxy]quinoline-2-carbonyl]amino]pentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2CCC(CC2)OC(C)C)=C(C=CC=C2)C2=N1 CBCVKKKQXQLQBX-VWLOTQADSA-N 0.000 claims 1
- LSAMBJNGLCXUJV-ROKPMTFOSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxo-4-[[4-[2-oxo-2-[(1r,5s)-3-oxo-8-azabicyclo[3.2.1]octan-8-yl]ethoxy]quinoline-2-carbonyl]amino]pentanoic acid Chemical compound O=C([C@H](CCC(O)=O)NC(=O)C=1C=C(C2=CC=CC=C2N=1)OCC(=O)N1[C@]2([H])CC[C@]1(CC(=O)C2)[H])N1CCN(C(=O)OCC)CC1 LSAMBJNGLCXUJV-ROKPMTFOSA-N 0.000 claims 1
- FAJICISULDPTIS-XCZPVHLTSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxo-4-[[4-[2-oxo-2-[(2s)-2-phenylpyrrolidin-1-yl]ethoxy]quinoline-2-carbonyl]amino]pentanoic 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=CC=CC=2)=C(C=CC=C2)C2=N1 FAJICISULDPTIS-XCZPVHLTSA-N 0.000 claims 1
- OEHBIYSNBJRBCS-NNTRXQOJSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxo-4-[[4-[2-oxo-2-[2-(oxolan-2-yl)piperidin-1-yl]ethoxy]quinoline-2-carbonyl]amino]pentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2C(CCCC2)C2OCCC2)=C(C=CC=C2)C2=N1 OEHBIYSNBJRBCS-NNTRXQOJSA-N 0.000 claims 1
- TZVBTWDCSRKUOI-ZYZRXSCRSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxo-4-[[4-[2-oxo-2-[3-(trifluoromethyl)pyrrolidin-1-yl]ethoxy]quinoline-2-carbonyl]amino]pentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2CC(CC2)C(F)(F)F)=C(C=CC=C2)C2=N1 TZVBTWDCSRKUOI-ZYZRXSCRSA-N 0.000 claims 1
- VPADRCCDVMFMCO-VWLOTQADSA-N (4s)-5-(4-ethoxycarbonylpiperazin-1-yl)-5-oxo-4-[[4-[2-oxo-2-[4-(2-oxopyrrolidin-1-yl)piperidin-1-yl]ethoxy]quinoline-2-carbonyl]amino]pentanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2CCC(CC2)N2C(CCC2)=O)=C(C=CC=C2)C2=N1 VPADRCCDVMFMCO-VWLOTQADSA-N 0.000 claims 1
- FTKHPONDZFEAMK-SMCANUKXSA-N (4s)-5-[4-(3-chlorobenzoyl)piperidin-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=C(Cl)C=CC=1)NC1CCC1 FTKHPONDZFEAMK-SMCANUKXSA-N 0.000 claims 1
- KTTMHMBSHJMNMQ-BDYUSTAISA-N (5s)-5-[[4-[2-[(2s)-2-(cyclobutylcarbamoyl)pyrrolidin-1-yl]-2-oxoethoxy]quinoline-2-carbonyl]amino]-6-(4-ethoxycarbonylpiperazin-1-yl)-6-oxohexanoic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCCC(O)=O)NC(=O)C1=CC(OCC(=O)N2[C@@H](CCC2)C(=O)NC2CCC2)=C(C=CC=C2)C2=N1 KTTMHMBSHJMNMQ-BDYUSTAISA-N 0.000 claims 1
- USWOSEUQVQFFGW-UHFFFAOYSA-N 1,2-dihydrocyclopenta[c]pyrrole Chemical compound C1=C[C]2[CH]NCC2=C1 USWOSEUQVQFFGW-UHFFFAOYSA-N 0.000 claims 1
- VASZIBLMRWWJEC-QFIPXVFZSA-N 1-[2-[2-[[(2s)-4-carboxy-1-(4-ethoxycarbonylpiperazin-1-yl)-1-oxobutan-2-yl]carbamoyl]-7-methylquinolin-4-yl]oxyacetyl]piperidine-4-carboxylic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2CCC(CC2)C(O)=O)=C(C=CC(C)=C2)C2=N1 VASZIBLMRWWJEC-QFIPXVFZSA-N 0.000 claims 1
- BFDQZNNQQGGXOY-QWAKEFERSA-N 1-[2-[2-[[(2s)-4-carboxy-1-(4-ethoxycarbonylpiperazin-1-yl)-1-oxobutan-2-yl]carbamoyl]-7-methylquinolin-4-yl]oxyacetyl]pyrrolidine-3-carboxylic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2CC(CC2)C(O)=O)=C(C=CC(C)=C2)C2=N1 BFDQZNNQQGGXOY-QWAKEFERSA-N 0.000 claims 1
- SRPVQFIMLLXYME-ZQRQZVKFSA-N 1-[2-[2-[[(2s)-4-carboxy-1-(4-ethoxycarbonylpiperazin-1-yl)-1-oxobutan-2-yl]carbamoyl]quinolin-4-yl]oxyacetyl]-4,4-difluoropyrrolidine-2-carboxylic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2C(CC(F)(F)C2)C(O)=O)=C(C=CC=C2)C2=N1 SRPVQFIMLLXYME-ZQRQZVKFSA-N 0.000 claims 1
- FPVYLLAGAVVJMO-FQEVSTJZSA-N 1-[2-[2-[[(2s)-4-carboxy-1-(4-ethoxycarbonylpiperazin-1-yl)-1-oxobutan-2-yl]carbamoyl]quinolin-4-yl]oxyacetyl]azetidine-3-carboxylic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2CC(C2)C(O)=O)=C(C=CC=C2)C2=N1 FPVYLLAGAVVJMO-FQEVSTJZSA-N 0.000 claims 1
- JMXRBYVEUHQKNA-ZYZRXSCRSA-N 1-[2-[2-[[(2s)-4-carboxy-1-(4-ethoxycarbonylpiperazin-1-yl)-1-oxobutan-2-yl]carbamoyl]quinolin-4-yl]oxyacetyl]pyrrolidine-3-carboxylic acid Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(O)=O)NC(=O)C1=CC(OCC(=O)N2CC(CC2)C(O)=O)=C(C=CC=C2)C2=N1 JMXRBYVEUHQKNA-ZYZRXSCRSA-N 0.000 claims 1
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- BYALJIWKNMRFJO-XWUYKKJTSA-N 4-[(2S)-2-[[4-[2-[(2S)-2-(cyclobutylcarbamoyl)pyrrolidin-1-yl]-2-oxoethoxy]-7-methylquinoline-2-carbonyl]amino]-5-(1-morpholin-4-ylbutan-2-yloxy)-5-oxopentanoyl]piperazine-1-carboxylic acid Chemical compound C1(CCC1)NC(=O)[C@H]1N(CCC1)C(COC1=CC(=NC2=CC(=CC=C12)C)C(=O)N[C@H](C(=O)N1CCN(CC1)C(=O)O)CCC(=O)OC(CC)CN1CCOCC1)=O BYALJIWKNMRFJO-XWUYKKJTSA-N 0.000 claims 1
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 claims 1
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- ZYQARAKFNVASOU-UPVQGACJSA-N C(=O)(O)CC[C@@H](C(=O)N1CCN(CC1)C(=O)O)NC(=O)C1=NC2=CC=C(C(=C2C(=C1)OCC(=O)N1[C@@H](CCC1)C(NC1CCC1)=O)C)F Chemical compound C(=O)(O)CC[C@@H](C(=O)N1CCN(CC1)C(=O)O)NC(=O)C1=NC2=CC=C(C(=C2C(=C1)OCC(=O)N1[C@@H](CCC1)C(NC1CCC1)=O)C)F ZYQARAKFNVASOU-UPVQGACJSA-N 0.000 claims 1
- 125000006375 C2-C10 alkynyl group Chemical group 0.000 claims 1
- HFJABBSPCLFMCC-OZXSUGGESA-N CCOC(=O)CC[C@@H](C(=O)N1CCN(CC1)C(=O)O)NC(=O)C2=NC3=C(C=C(C(=C3)C)F)C(=C2)OCC(=O)N4CCC[C@H]4C(=O)NC5CC5 Chemical compound CCOC(=O)CC[C@@H](C(=O)N1CCN(CC1)C(=O)O)NC(=O)C2=NC3=C(C=C(C(=C3)C)F)C(=C2)OCC(=O)N4CCC[C@H]4C(=O)NC5CC5 HFJABBSPCLFMCC-OZXSUGGESA-N 0.000 claims 1
- 101100063435 Caenorhabditis elegans din-1 gene Proteins 0.000 claims 1
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- HGVDHZBSSITLCT-JLJPHGGASA-N Edoxaban Chemical compound N([C@H]1CC[C@@H](C[C@H]1NC(=O)C=1SC=2CN(C)CCC=2N=1)C(=O)N(C)C)C(=O)C(=O)NC1=CC=C(Cl)C=N1 HGVDHZBSSITLCT-JLJPHGGASA-N 0.000 claims 1
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- 101800000224 Glucagon-like peptide 1 Proteins 0.000 claims 1
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- 102000010752 Plasminogen Inactivators Human genes 0.000 claims 1
- 108010077971 Plasminogen Inactivators Proteins 0.000 claims 1
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- 229940098892 Protease-activated receptor-1 antagonist Drugs 0.000 claims 1
- 229940123495 Squalene synthetase inhibitor Drugs 0.000 claims 1
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- XRVDKIQEFCJTBZ-UHFFFAOYSA-N [1,3]oxazolo[5,4-c]pyridine Chemical compound C1=NC=C2OC=NC2=C1 XRVDKIQEFCJTBZ-UHFFFAOYSA-N 0.000 claims 1
- 239000001361 adipic acid Substances 0.000 claims 1
- KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical group C=1OC2=CC(OC/C=C/CN(CC=C)C)=CC=C2C=1C1=CC=C(Br)C=C1 KCNKJCHARANTIP-SNAWJCMRSA-N 0.000 claims 1
- HTIQEAQVCYTUBX-UHFFFAOYSA-N amlodipine Chemical compound CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl HTIQEAQVCYTUBX-UHFFFAOYSA-N 0.000 claims 1
- 230000003276 anti-hypertensive effect Effects 0.000 claims 1
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- FGHCKBZHONMUGU-QFIPXVFZSA-N butyl 4-[(2s)-2-[[4-[2-(3,3-difluoropyrrolidin-1-yl)-2-oxoethoxy]-7-methylquinoline-2-carbonyl]amino]-4-(2h-tetrazol-5-yl)butanoyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCCCC)CCN1C(=O)[C@@H](NC(=O)C=1N=C2C=C(C)C=CC2=C(OCC(=O)N2CC(F)(F)CC2)C=1)CCC1=NNN=N1 FGHCKBZHONMUGU-QFIPXVFZSA-N 0.000 claims 1
- PTUZGOUEAJHRQB-DITALETJSA-N butyl 4-[(2s)-5-ethoxy-2-[[7-methyl-4-[2-oxo-2-[(2s)-2-phenylpyrrolidin-1-yl]ethoxy]quinoline-2-carbonyl]amino]-5-oxopentanoyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCCCC)CCN1C(=O)[C@H](CCC(=O)OCC)NC(=O)C1=CC(OCC(=O)N2[C@@H](CCC2)C=2C=CC=CC=2)=C(C=CC(C)=C2)C2=N1 PTUZGOUEAJHRQB-DITALETJSA-N 0.000 claims 1
- IXZMKCIBWLLTBP-UQARTHHBSA-N butyl 4-[2-[[4-[(2r)-1-[(2s,4r)-4-cyano-2-(cyclobutylcarbamoyl)pyrrolidin-1-yl]-1-oxopropan-2-yl]oxy-7-methylquinoline-2-carbonyl]amino]acetyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCCCC)CCN1C(=O)CNC(=O)C1=CC(O[C@H](C)C(=O)N2[C@@H](C[C@H](C2)C#N)C(=O)NC2CCC2)=C(C=CC(C)=C2)C2=N1 IXZMKCIBWLLTBP-UQARTHHBSA-N 0.000 claims 1
- BAUARULBZWXDPT-UHFFFAOYSA-N butyl 4-[2-[[4-[2-(2,4-dioxo-1,3,9-triazaspiro[4.5]decan-9-yl)-2-oxoethoxy]-7-methylquinoline-2-carbonyl]amino]acetyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCCCC)CCN1C(=O)CNC(=O)C1=CC(OCC(=O)N2CC3(CCC2)C(NC(=O)N3)=O)=C(C=CC(C)=C2)C2=N1 BAUARULBZWXDPT-UHFFFAOYSA-N 0.000 claims 1
- REVXDAADLXCGMG-UHFFFAOYSA-N butyl 4-[2-[[4-[2-(4-cyclopropylpiperazin-1-yl)-2-oxoethoxy]-7-methylquinoline-2-carbonyl]amino]acetyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCCCC)CCN1C(=O)CNC(=O)C1=CC(OCC(=O)N2CCN(CC2)C2CC2)=C(C=CC(C)=C2)C2=N1 REVXDAADLXCGMG-UHFFFAOYSA-N 0.000 claims 1
- IVPNHVPGLUWOPE-SANMLTNESA-N butyl 4-[2-[[4-[2-[(2s)-2-(cyclopropylcarbamoyl)pyrrolidin-1-yl]-2-oxoethoxy]-7-methylquinoline-2-carbonyl]amino]acetyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCCCC)CCN1C(=O)CNC(=O)C1=CC(OCC(=O)N2[C@@H](CCC2)C(=O)NC2CC2)=C(C=CC(C)=C2)C2=N1 IVPNHVPGLUWOPE-SANMLTNESA-N 0.000 claims 1
- BEKZIOIPPSQIBH-MHZLTWQESA-N butyl 4-[2-[[4-[2-[(2s)-2-(cyclopropylmethylcarbamoyl)pyrrolidin-1-yl]-2-oxoethoxy]-7-methylquinoline-2-carbonyl]amino]acetyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCCCC)CCN1C(=O)CNC(=O)C1=CC(OCC(=O)N2[C@@H](CCC2)C(=O)NCC2CC2)=C(C=CC(C)=C2)C2=N1 BEKZIOIPPSQIBH-MHZLTWQESA-N 0.000 claims 1
- DALRPCXVHZVTLO-OUTSHDOLSA-N butyl 4-[2-[[4-[2-[(2s,4r)-4-cyano-2-(cyclobutylcarbamoyl)pyrrolidin-1-yl]-2-oxoethoxy]-6,7-dimethylquinoline-2-carbonyl]amino]acetyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCCCC)CCN1C(=O)CNC(=O)C1=CC(OCC(=O)N2[C@@H](C[C@H](C2)C#N)C(=O)NC2CCC2)=C(C=C(C)C(C)=C2)C2=N1 DALRPCXVHZVTLO-OUTSHDOLSA-N 0.000 claims 1
- CKOPCJWUPXIUGP-SFTDATJTSA-N butyl 4-[2-[[4-[2-[(2s,4s)-2-cyano-4-fluoropyrrolidin-1-yl]-2-oxoethoxy]-7-methylquinoline-2-carbonyl]amino]acetyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCCCC)CCN1C(=O)CNC(=O)C1=CC(OCC(=O)N2[C@@H](C[C@H](F)C2)C#N)=C(C=CC(C)=C2)C2=N1 CKOPCJWUPXIUGP-SFTDATJTSA-N 0.000 claims 1
- XVFIBZMWDHINQJ-UHFFFAOYSA-N butyl 4-[2-[[4-[2-[2-(1h-indol-2-yl)pyrrolidin-1-yl]-2-oxoethoxy]-7-methylquinoline-2-carbonyl]amino]acetyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCCCC)CCN1C(=O)CNC(=O)C1=CC(OCC(=O)N2C(CCC2)C=2NC3=CC=CC=C3C=2)=C(C=CC(C)=C2)C2=N1 XVFIBZMWDHINQJ-UHFFFAOYSA-N 0.000 claims 1
- FCSRVRZNQVEZLM-CZUALIRWSA-N butyl 4-[2-[[7-methyl-4-[(2r)-1-(2-methyl-3,3a,4,6,7,7a-hexahydro-1h-pyrrolo[3,4-c]pyridin-5-yl)-1-oxopropan-2-yl]oxyquinoline-2-carbonyl]amino]acetyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCCCC)CCN1C(=O)CNC(=O)C1=CC(O[C@H](C)C(=O)N2CC3CN(C)CC3CC2)=C(C=CC(C)=C2)C2=N1 FCSRVRZNQVEZLM-CZUALIRWSA-N 0.000 claims 1
- LFIBUCNGCJWRGT-NDEPHWFRSA-N butyl 4-[2-[[7-methyl-4-[2-[(2s)-2-(4-methylpiperazine-1-carbonyl)pyrrolidin-1-yl]-2-oxoethoxy]quinoline-2-carbonyl]amino]acetyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCCCC)CCN1C(=O)CNC(=O)C1=CC(OCC(=O)N2[C@@H](CCC2)C(=O)N2CCN(C)CC2)=C(C=CC(C)=C2)C2=N1 LFIBUCNGCJWRGT-NDEPHWFRSA-N 0.000 claims 1
- SUDUEYJZLVVQRF-MHZLTWQESA-N butyl 4-[2-[[7-methyl-4-[2-[(2s)-2-[(1-methylazetidin-3-yl)carbamoyl]pyrrolidin-1-yl]-2-oxoethoxy]quinoline-2-carbonyl]amino]acetyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCCCC)CCN1C(=O)CNC(=O)C1=CC(OCC(=O)N2[C@@H](CCC2)C(=O)NC2CN(C)C2)=C(C=CC(C)=C2)C2=N1 SUDUEYJZLVVQRF-MHZLTWQESA-N 0.000 claims 1
- TXMWEYZMAKKPLL-QHCPKHFHSA-N butyl 4-[2-[[7-methyl-4-[2-[(3s)-3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]-2-oxoethoxy]quinoline-2-carbonyl]amino]acetyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCCCC)CCN1C(=O)CNC(=O)C1=CC(OCC(=O)N2C[C@H](CC2)NC(=O)OC(C)(C)C)=C(C=CC(C)=C2)C2=N1 TXMWEYZMAKKPLL-QHCPKHFHSA-N 0.000 claims 1
- DUFXGRSSDVYXHB-UHFFFAOYSA-N butyl 4-[2-[[7-methyl-4-[2-oxo-2-(6-oxo-1,3,4,7,8,8a-hexahydropyrrolo[1,2-a]pyrazin-2-yl)ethoxy]quinoline-2-carbonyl]amino]acetyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCCCC)CCN1C(=O)CNC(=O)C1=CC(OCC(=O)N2CC3N(C(CC3)=O)CC2)=C(C=CC(C)=C2)C2=N1 DUFXGRSSDVYXHB-UHFFFAOYSA-N 0.000 claims 1
- GRHADFNYADRMAU-DEOSSOPVSA-N butyl 4-[2-[[7-methyl-4-[2-oxo-2-[(2s)-2-(2,2,2-trifluoroethylcarbamoyl)pyrrolidin-1-yl]ethoxy]quinoline-2-carbonyl]amino]acetyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCCCC)CCN1C(=O)CNC(=O)C1=CC(OCC(=O)N2[C@@H](CCC2)C(=O)NCC(F)(F)F)=C(C=CC(C)=C2)C2=N1 GRHADFNYADRMAU-DEOSSOPVSA-N 0.000 claims 1
- DKAQYGFIXQYLRP-UHFFFAOYSA-N butyl 4-[2-[[7-methyl-4-[2-oxo-2-[3-(trifluoromethyl)-4,6-dihydro-1h-pyrrolo[3,4-c]pyrazol-5-yl]ethoxy]quinoline-2-carbonyl]amino]acetyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCCCC)CCN1C(=O)CNC(=O)C1=CC(OCC(=O)N2CC=3C(=NNC=3C2)C(F)(F)F)=C(C=CC(C)=C2)C2=N1 DKAQYGFIXQYLRP-UHFFFAOYSA-N 0.000 claims 1
- JWKZJCRNJGTSII-UHFFFAOYSA-N butyl 4-[2-[[7-methyl-4-[2-oxo-2-[4-(2,2,2-trifluoroethyl)piperazin-1-yl]ethoxy]quinoline-2-carbonyl]amino]acetyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCCCC)CCN1C(=O)CNC(=O)C1=CC(OCC(=O)N2CCN(CC(F)(F)F)CC2)=C(C=CC(C)=C2)C2=N1 JWKZJCRNJGTSII-UHFFFAOYSA-N 0.000 claims 1
- 125000000597 dioxinyl group Chemical group 0.000 claims 1
- NHBDIBFRBOMPGE-WNJJXGMVSA-N ethyl 4-[(2s)-2-[[4-[2-[(2s)-2-(cyclobutylcarbamoyl)pyrrolidin-1-yl]-2-oxoethoxy]-6-fluoro-7-methylquinoline-2-carbonyl]amino]-5-ethoxy-5-oxopentanoyl]piperazine-1-carboxylate Chemical compound O=C([C@@H]1CCCN1C(=O)COC=1C=C(N=C2C=C(C)C(F)=CC2=1)C(=O)N[C@@H](CCC(=O)OCC)C(=O)N1CCN(CC1)C(=O)OCC)NC1CCC1 NHBDIBFRBOMPGE-WNJJXGMVSA-N 0.000 claims 1
- JOPAMJGJPDWILJ-IZEXYCQBSA-N ethyl 4-[(2s)-2-[[4-[2-[(2s)-2-(cyclobutylcarbamoyl)pyrrolidin-1-yl]-2-oxoethoxy]-7-methylquinoline-2-carbonyl]amino]-5-(3-methoxypropoxy)-5-oxopentanoyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(=O)OCCCOC)NC(=O)C1=CC(OCC(=O)N2[C@@H](CCC2)C(=O)NC2CCC2)=C(C=CC(C)=C2)C2=N1 JOPAMJGJPDWILJ-IZEXYCQBSA-N 0.000 claims 1
- OHVOCNDAVJFBRD-VBTAUBHQSA-N ethyl 4-[(2s)-2-[[4-[2-[(2s)-2-(cyclobutylcarbamoyl)pyrrolidin-1-yl]-2-oxoethoxy]-7-methylquinoline-2-carbonyl]amino]-5-(cyclohexylmethoxy)-5-oxopentanoyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@@H](NC(=O)C=1N=C2C=C(C)C=CC2=C(OCC(=O)N2[C@@H](CCC2)C(=O)NC2CCC2)C=1)CCC(=O)OCC1CCCCC1 OHVOCNDAVJFBRD-VBTAUBHQSA-N 0.000 claims 1
- QNOBNCMBDHXVRV-AHWVRZQESA-N ethyl 4-[(2s)-2-[[4-[2-[(2s)-2-(cyclobutylcarbamoyl)pyrrolidin-1-yl]-2-oxoethoxy]quinoline-2-carbonyl]amino]-4-hydroxybutanoyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCO)NC(=O)C1=CC(OCC(=O)N2[C@@H](CCC2)C(=O)NC2CCC2)=C(C=CC=C2)C2=N1 QNOBNCMBDHXVRV-AHWVRZQESA-N 0.000 claims 1
- SVHBBOXKLMBZOX-BDYUSTAISA-N ethyl 4-[(2s)-2-[[4-[2-[(2s)-2-(cyclopropylcarbamoyl)pyrrolidin-1-yl]-2-oxoethoxy]quinoline-2-carbonyl]amino]-5-ethoxy-5-oxopentanoyl]piperazine-1-carboxylate Chemical compound O=C([C@@H]1CCCN1C(=O)COC=1C=C(N=C2C=CC=CC2=1)C(=O)N[C@@H](CCC(=O)OCC)C(=O)N1CCN(CC1)C(=O)OCC)NC1CC1 SVHBBOXKLMBZOX-BDYUSTAISA-N 0.000 claims 1
- XDBQGHOXYVFDOU-FIBWVYCGSA-N ethyl 4-[(2s)-2-[[4-[2-[(2s)-2-[cyclobutyl(methyl)carbamoyl]pyrrolidin-1-yl]-2-oxoethoxy]-7-methylquinoline-2-carbonyl]amino]-5-ethoxy-5-oxopentanoyl]piperazine-1-carboxylate Chemical compound O=C([C@@H]1CCCN1C(=O)COC=1C=C(N=C2C=C(C)C=CC2=1)C(=O)N[C@@H](CCC(=O)OCC)C(=O)N1CCN(CC1)C(=O)OCC)N(C)C1CCC1 XDBQGHOXYVFDOU-FIBWVYCGSA-N 0.000 claims 1
- SCZDYTFZZWZXSZ-IGKIAQTJSA-N ethyl 4-[(2s)-5-amino-2-[[4-[2-[(2s)-2-(cyclobutylcarbamoyl)pyrrolidin-1-yl]-2-oxoethoxy]-7-methylquinoline-2-carbonyl]amino]-5-oxopentanoyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1C(=O)[C@H](CCC(N)=O)NC(=O)C1=CC(OCC(=O)N2[C@@H](CCC2)C(=O)NC2CCC2)=C(C=CC(C)=C2)C2=N1 SCZDYTFZZWZXSZ-IGKIAQTJSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
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- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Virology (AREA)
- Vascular Medicine (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Quinoline Compounds (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07008209.4 | 2007-04-23 | ||
| EP07008209 | 2007-04-23 | ||
| PCT/EP2008/002790 WO2008128647A1 (en) | 2007-04-23 | 2008-04-09 | Quinoline-carboxamide derivatives as p2y12 antagonists |
Publications (2)
| Publication Number | Publication Date |
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| AU2008241091A1 AU2008241091A1 (en) | 2008-10-30 |
| AU2008241091B2 true AU2008241091B2 (en) | 2013-05-09 |
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| AU2008241091A Ceased AU2008241091B2 (en) | 2007-04-23 | 2008-04-09 | Quinoline-carboxamide derivatives as P2Y12 antagonists |
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| EP (1) | EP2148871A1 (enExample) |
| JP (1) | JP5309131B2 (enExample) |
| KR (1) | KR20100015886A (enExample) |
| CN (1) | CN101663293B (enExample) |
| AR (1) | AR066225A1 (enExample) |
| AU (1) | AU2008241091B2 (enExample) |
| BR (1) | BRPI0810462A2 (enExample) |
| CA (1) | CA2684644A1 (enExample) |
| CL (1) | CL2008001157A1 (enExample) |
| IL (1) | IL201620A (enExample) |
| MX (1) | MX2009011089A (enExample) |
| MY (1) | MY153427A (enExample) |
| PA (1) | PA8777901A1 (enExample) |
| PE (1) | PE20090241A1 (enExample) |
| TW (1) | TW200848042A (enExample) |
| UY (1) | UY31039A1 (enExample) |
| WO (1) | WO2008128647A1 (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2002235694B2 (en) | 2001-02-28 | 2007-06-14 | Covalon Technologies Inc. | Method of making anti-microbial polymeric surfaces |
| WO2009082526A2 (en) * | 2007-10-05 | 2009-07-02 | Pharmacopeia, Inc. | Ortho pyrrolidine, benzyl-substituted heterocycle ccr1 antagonists for autoimmune diseases & inflammation |
| TWI361690B (en) | 2007-11-29 | 2012-04-11 | Actelion Pharmaceuticals Ltd | Phosphonic acid derivatives |
| AR071653A1 (es) | 2008-04-11 | 2010-07-07 | Actelion Pharmaceuticals Ltd | Derivados 2-fenil-4-ciclopropil-pirimidina |
| RU2401831C2 (ru) * | 2008-12-15 | 2010-10-20 | Алла Хем, Ллс | Средство, снижающее влечение к алкоголю, фармацевтическая композиция и способы ее получения, лекарственное средство и способ лечения |
| WO2010116328A2 (en) * | 2009-04-08 | 2010-10-14 | Actelion Pharmaceuticals Ltd | 6-(3-aza-bicyclo[3.1.0]hex-3-yl)-2-phenyl-pyrimidines |
| EP2421859B1 (en) | 2009-04-22 | 2014-04-09 | Actelion Pharmaceuticals Ltd. | Thiazole derivatives and their use as p2y12 receptor antagonists |
| JP5597202B2 (ja) | 2009-08-28 | 2014-10-01 | 第一三共株式会社 | ３−（ビアリールオキシ）プロピオン酸誘導体 |
| AR079451A1 (es) * | 2009-12-18 | 2012-01-25 | Nycomed Gmbh | Compuestos 3,4,4a,10b-tetrahidro-1h-tiopirano[4,3-c]isoquinolina |
| CN103857288B (zh) | 2011-03-04 | 2016-09-21 | 葛兰素史密斯克莱知识产权发展有限公司 | 作为激酶抑制剂的氨基-喹啉 |
| TWI547494B (zh) | 2011-08-18 | 2016-09-01 | 葛蘭素史克智慧財產發展有限公司 | 作為激酶抑制劑之胺基喹唑啉類 |
| WO2013033178A1 (en) | 2011-08-30 | 2013-03-07 | University Of Utah Research Foundation | Methods and compositions for treating nephrogenic diabetes insipidus |
| CN102584852B (zh) * | 2011-12-30 | 2014-08-13 | 厦门大学 | 真菌代谢产物桥南霉素及其制备方法和应用 |
| AR092529A1 (es) | 2012-09-13 | 2015-04-22 | Glaxosmithkline Llc | Compuesto de aminoquinazolina, composicion farmaceutica que lo comprende y uso de dicho compuesto para la preparacion de un medicamento |
| AR092530A1 (es) | 2012-09-13 | 2015-04-22 | Glaxosmithkline Llc | Compuesto de amino-quinolina, composicion farmaceutica que lo comprende y uso de dicho compuesto para la preparacion de un medicamento |
| EP2725025A1 (fr) * | 2012-10-26 | 2014-04-30 | Sanofi | Dérives de 1H-indole-3-carboxamide et leurs utilisation comme antagonistes du P2Y12 |
| EP2958911B1 (en) | 2013-02-21 | 2017-10-18 | GlaxoSmithKline Intellectual Property Development Limited | Quinazolines as kinase inhibitors |
| CN104109158A (zh) * | 2013-04-16 | 2014-10-22 | 上海医药工业研究院 | 一种纯化利伐沙班的方法 |
| DE102014108210A1 (de) | 2014-06-11 | 2015-12-17 | Dietrich Gulba | Rodentizid |
| DE102015217396B4 (de) | 2014-09-11 | 2018-07-26 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | System, insbesondere System zur Eingabesteuerung für eine Arbeitshilfe |
| CN106496249B (zh) * | 2015-09-07 | 2019-12-13 | 江苏恒瑞医药股份有限公司 | 噁唑并吲哚类衍生物、其制备方法及其在医药上的应用 |
| US10730868B2 (en) * | 2016-07-14 | 2020-08-04 | Bristol-Myers Squibb Company | Bicyclic heteroaryl substituted compounds |
| HUE057772T2 (hu) | 2016-09-22 | 2022-06-28 | Idorsia Pharmaceuticals Ltd | Kristályos formák |
| KR102510832B1 (ko) | 2017-03-15 | 2023-03-15 | 이도르시아 파마슈티컬스 리미티드 | P2y12 수용체 안타고니스트의 피하 투여 |
| CN107648607A (zh) * | 2017-09-11 | 2018-02-02 | 南昌大学 | 嘌呤2y12受体拮抗剂在制备糖尿病神经病理损伤疾病药物中的应用 |
| EP4070658A1 (de) | 2021-04-06 | 2022-10-12 | BIORoxx GmbH | Verwendung von blutgerinnungshemmenden verbindungen als rodentizide |
| WO2023108363A1 (en) * | 2021-12-13 | 2023-06-22 | Beijing Honghui Meditech Co., Ltd | Pyrimidine-annulated triazole derivatives and their use in platelet aggregation inhibition |
| CN115429874A (zh) * | 2022-09-20 | 2022-12-06 | 暨南大学 | 水蛭素靶向并抑制dpp4治疗糖尿病 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2002098856A2 (en) * | 2001-06-06 | 2002-12-12 | Schering Aktiengesellschaft | Piperazine oxyquinoline (naphthaline) platelet adenosine diphosphate receptor antagonists |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5612359A (en) * | 1994-08-26 | 1997-03-18 | Bristol-Myers Squibb Company | Substituted biphenyl isoxazole sulfonamides |
| TW536540B (en) * | 1997-01-30 | 2003-06-11 | Bristol Myers Squibb Co | Endothelin antagonists: N-[[2'-[[(4,5-dimethyl-3-isoxazolyl)amino]sulfonyl]-4-(2-oxazolyl)[1,1'-biphenyl]-2-yl]methyl]-N,3,3-trimethylbutanamide and N-(4,5-dimethyl-3-isoxazolyl)-2'-[(3,3-dimethyl-2-oxo-1-pyrrolidinyl)methyl]-4'-(2-oxazolyl)[1,1'-biphe |
| PE121699A1 (es) | 1997-02-18 | 1999-12-08 | Boehringer Ingelheim Pharma | Heterociclos biciclicos disustituidos como inhibidores de la trombina |
| ZA985247B (en) | 1997-06-19 | 1999-12-17 | Du Pont Merck Pharma | Guanidine mimics as factor Xa inhibitors. |
| IL140622A0 (en) | 1998-07-06 | 2002-02-10 | Bristol Myers Squibb Co | Biphenyl sufonamide derivatives, pharmaceutical compositions containing the same and methods for the preparation thereof |
| WO2000076970A2 (en) | 1999-06-14 | 2000-12-21 | Eli Lilly And Company | Serine protease inhibitors |
| MY125533A (en) | 1999-12-06 | 2006-08-30 | Bristol Myers Squibb Co | Heterocyclic dihydropyrimidine compounds |
| DE19962924A1 (de) | 1999-12-24 | 2001-07-05 | Bayer Ag | Substituierte Oxazolidinone und ihre Verwendung |
| AR035216A1 (es) | 2000-12-01 | 2004-05-05 | Astrazeneca Ab | Derivados de acido mandelico ,derivados farmaceuticamente aceptables, uso de estos derivados para la fabricacion de medicamentos, metodos de tratamiento ,procesos para la preparacion de estos derivados, y compuestos intermediarios |
| SI1427415T1 (sl) | 2001-09-21 | 2009-12-31 | Bristol Myers Squibb Co | Sestavine, ki vsebujejo laktame in njihovi derivati kot inhibitorji faktorja xa |
| KR20050085580A (ko) * | 2002-12-11 | 2005-08-29 | 쉐링 악티엔게젤샤프트 | 혈소판 아데노신 디포스페이트 수용체 길항제로서의2-아미노카르보닐-퀴놀린 화합물 |
| MXPA06000675A (es) | 2003-07-24 | 2006-04-19 | Astellas Pharma Inc | Derivado de quinolona o sal del mismo. |
| US7157445B2 (en) * | 2004-02-26 | 2007-01-02 | Aventis Pharma S.A. | Administration of enoxaparin sodium to patients with severe renal impairment |
| JP2008094720A (ja) | 2005-01-20 | 2008-04-24 | Astellas Pharma Inc | キノロン誘導体のプロドラッグ又はその塩 |
| TW200640877A (en) * | 2005-04-28 | 2006-12-01 | Actelion Pharmaceuticals Ltd | Pyrimidine derivatives |
| MX2008002363A (es) * | 2005-08-17 | 2008-03-18 | Schering Corp | Ligandos novedosos de cinasa basados en quinolina de alta afinidad. |
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2008
- 2008-04-09 KR KR1020097022288A patent/KR20100015886A/ko not_active Ceased
- 2008-04-09 CA CA002684644A patent/CA2684644A1/en not_active Abandoned
- 2008-04-09 EP EP08735104A patent/EP2148871A1/en not_active Withdrawn
- 2008-04-09 MX MX2009011089A patent/MX2009011089A/es active IP Right Grant
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- 2008-04-09 JP JP2010504490A patent/JP5309131B2/ja not_active Expired - Fee Related
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- 2008-04-09 WO PCT/EP2008/002790 patent/WO2008128647A1/en not_active Ceased
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- 2009-10-19 IL IL201620A patent/IL201620A/en not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002098856A2 (en) * | 2001-06-06 | 2002-12-12 | Schering Aktiengesellschaft | Piperazine oxyquinoline (naphthaline) platelet adenosine diphosphate receptor antagonists |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2008128647A1 (en) | 2008-10-30 |
| JP5309131B2 (ja) | 2013-10-09 |
| CN101663293B (zh) | 2013-07-31 |
| US8669266B2 (en) | 2014-03-11 |
| KR20100015886A (ko) | 2010-02-12 |
| HK1141803A1 (en) | 2010-11-19 |
| PE20090241A1 (es) | 2009-04-03 |
| PA8777901A1 (es) | 2008-11-19 |
| CN101663293A (zh) | 2010-03-03 |
| MY153427A (en) | 2015-02-13 |
| IL201620A (en) | 2013-11-28 |
| CA2684644A1 (en) | 2008-10-30 |
| CL2008001157A1 (es) | 2008-11-03 |
| JP2010524984A (ja) | 2010-07-22 |
| BRPI0810462A2 (pt) | 2014-10-14 |
| MX2009011089A (es) | 2009-10-30 |
| AU2008241091A1 (en) | 2008-10-30 |
| EP2148871A1 (en) | 2010-02-03 |
| UY31039A1 (es) | 2008-11-28 |
| TW200848042A (en) | 2008-12-16 |
| AR066225A1 (es) | 2009-08-05 |
| US20100135999A1 (en) | 2010-06-03 |
| IL201620A0 (en) | 2010-05-31 |
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