OA12727A - Indole-2-carboxamides as factor XA inhibitors. - Google Patents

Info

Publication number

OA12727A

OA12727A OA1200400142A OA1200400142A OA12727A OA 12727 A OA12727 A OA 12727A OA 1200400142 A OA1200400142 A OA 1200400142A OA 1200400142 A OA1200400142 A OA 1200400142A OA 12727 A OA12727 A OA 12727A

Authority

OA

OAPI

Prior art keywords

chloro

indole

piperidin

thiophen

amide

Prior art date

2001-11-22

Links

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• Global Dossier
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• VFHUJFBEFDVZPJ-UHFFFAOYSA-N 1h-indole-2-carboxamide Chemical class C1=CC=C2NC(C(=O)N)=CC2=C1 VFHUJFBEFDVZPJ-UHFFFAOYSA-N 0.000 title 1
• 229940123583 Factor Xa inhibitor Drugs 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 302
• 238000000034 method Methods 0.000 claims abstract description 72
• 230000005764 inhibitory process Effects 0.000 claims abstract description 20
• 230000023555 blood coagulation Effects 0.000 claims abstract description 12
• 238000002560 therapeutic procedure Methods 0.000 claims abstract description 12
• 239000003814 drug Substances 0.000 claims abstract description 9
• 230000008569 process Effects 0.000 claims abstract description 6
• 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 5
• 208000001435 Thromboembolism Diseases 0.000 claims abstract description 3
• -1 phenylpyridyl Chemical group 0.000 claims description 262
• 239000002253 acid Substances 0.000 claims description 140
• ZRQQXFMGYSOKDF-UHFFFAOYSA-N 1-propan-2-ylpiperidin-4-amine Chemical compound CC(C)N1CCC(N)CC1 ZRQQXFMGYSOKDF-UHFFFAOYSA-N 0.000 claims description 118
• 239000000203 mixture Substances 0.000 claims description 92
• 239000000460 chlorine Substances 0.000 claims description 70
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 69
• 125000000217 alkyl group Chemical group 0.000 claims description 69
• 125000001072 heteroaryl group Chemical group 0.000 claims description 62
• 229910052736 halogen Inorganic materials 0.000 claims description 55
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 54
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 49
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 45
• 150000002367 halogens Chemical class 0.000 claims description 45
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 42
• RJCRRLMFYIXJAH-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]indole-2-carboxylic acid Chemical compound OC(=O)C1=CC2=CC=CC=C2N1CC(=NO1)C=C1C1=CC=C(Cl)S1 RJCRRLMFYIXJAH-UHFFFAOYSA-N 0.000 claims description 41
• 125000003118 aryl group Chemical group 0.000 claims description 41
• 229960000583 acetic acid Drugs 0.000 claims description 40
• 150000003839 salts Chemical class 0.000 claims description 38
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 36
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 36
• 229910052757 nitrogen Inorganic materials 0.000 claims description 36
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 31
• 230000015572 biosynthetic process Effects 0.000 claims description 30
• 150000002148 esters Chemical class 0.000 claims description 28
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 27
• 125000004122 cyclic group Chemical group 0.000 claims description 22
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 21
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 21
• 229910052760 oxygen Inorganic materials 0.000 claims description 21
• 239000001301 oxygen Substances 0.000 claims description 21
• 229910052717 sulfur Inorganic materials 0.000 claims description 21
• 239000011593 sulfur Substances 0.000 claims description 21
• 125000001041 indolyl group Chemical group 0.000 claims description 20
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 19
• 125000005842 heteroatom Chemical group 0.000 claims description 18
• 229920006395 saturated elastomer Polymers 0.000 claims description 18
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 17
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 17
• 125000002950 monocyclic group Chemical group 0.000 claims description 17
• 150000003536 tetrazoles Chemical class 0.000 claims description 17
• 125000002883 imidazolyl group Chemical group 0.000 claims description 16
• BTDZSVPICJLNIN-UHFFFAOYSA-N 1-pyridin-4-ylpiperidin-4-amine Chemical compound C1CC(N)CCN1C1=CC=NC=C1 BTDZSVPICJLNIN-UHFFFAOYSA-N 0.000 claims description 15
• 125000002619 bicyclic group Chemical group 0.000 claims description 15
• 229910052801 chlorine Inorganic materials 0.000 claims description 15
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 15
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 14
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 14
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 14
• 125000004076 pyridyl group Chemical group 0.000 claims description 14
• 125000001544 thienyl group Chemical group 0.000 claims description 14
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 13
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
• JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 12
• FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims description 12
• CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 claims description 12
• JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 12
• QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 12
• POXWDTQUDZUOGP-UHFFFAOYSA-N 1h-1,4-diazepine Chemical compound N1C=CC=NC=C1 POXWDTQUDZUOGP-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
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 12
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 12
• DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 claims description 12
• XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 12
• 229910052794 bromium Inorganic materials 0.000 claims description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
• 125000000524 functional group Chemical group 0.000 claims description 12
• 125000005843 halogen group Chemical group 0.000 claims description 12
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 12
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
• IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims description 12
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 12
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 12
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 12
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 12
• 125000000335 thiazolyl group Chemical group 0.000 claims description 12
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 12
• LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 claims description 11
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 11
• 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 11
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 11
• NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 11
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
• 229910052731 fluorine Inorganic materials 0.000 claims description 11
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 11
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 11
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 11
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 10
• 125000004429 atom Chemical group 0.000 claims description 10
• 125000004432 carbon atom Chemical group C* 0.000 claims description 10
• 125000002541 furyl group Chemical group 0.000 claims description 10
• 239000001257 hydrogen Substances 0.000 claims description 10
• 229910052739 hydrogen Inorganic materials 0.000 claims description 10
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 10
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 10
• NBNWLLXCAIOATK-UHFFFAOYSA-N 1-[(3-methoxyphenyl)methyl]indole-2-carboxylic acid Chemical compound COC1=CC=CC(CN2C3=CC=CC=C3C=C2C(O)=O)=C1 NBNWLLXCAIOATK-UHFFFAOYSA-N 0.000 claims description 9
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 9
• 125000002971 oxazolyl group Chemical group 0.000 claims description 9
• VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 9
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
• 208000007536 Thrombosis Diseases 0.000 claims description 8
• 239000003146 anticoagulant agent Substances 0.000 claims description 8
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 8
• 229910052799 carbon Inorganic materials 0.000 claims description 8
• SJGALSBBFTYSBA-UHFFFAOYSA-N oxaziridine Chemical compound C1NO1 SJGALSBBFTYSBA-UHFFFAOYSA-N 0.000 claims description 8
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 8
• IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 claims description 8
• OEACEEHJARIXJW-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]indole-5-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC2=CC(C(O)=O)=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 OEACEEHJARIXJW-UHFFFAOYSA-N 0.000 claims description 7
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 7
• 150000001408 amides Chemical class 0.000 claims description 7
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 7
• 239000002243 precursor Substances 0.000 claims description 7
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 7
• ZFCKJGACJXTSOI-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-7-methylindole-2-carboxylic acid Chemical compound C1=2C(C)=CC=CC=2C=C(C(O)=O)N1CC(=NO1)C=C1C1=CC=C(Cl)S1 ZFCKJGACJXTSOI-UHFFFAOYSA-N 0.000 claims description 6
• 208000005189 Embolism Diseases 0.000 claims description 6
• 230000001154 acute effect Effects 0.000 claims description 6
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 6
• 201000010099 disease Diseases 0.000 claims description 6
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
• 150000004702 methyl esters Chemical class 0.000 claims description 6
• 125000003386 piperidinyl group Chemical group 0.000 claims description 6
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 6
• 125000005494 pyridonyl group Chemical group 0.000 claims description 6
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
• 125000005493 quinolyl group Chemical group 0.000 claims description 6
• 238000001356 surgical procedure Methods 0.000 claims description 6
• 125000001425 triazolyl group Chemical group 0.000 claims description 6
• DQJGJGNWFRPEHZ-UHFFFAOYSA-N 1-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-2-[(1-propan-2-ylpiperidin-4-yl)carbamoyl]indole-4-carboxylic acid Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC2=C(C(O)=O)C=CC=C2N1CC1=NOC(C=2SC(Cl)=CC=2)=C1 DQJGJGNWFRPEHZ-UHFFFAOYSA-N 0.000 claims description 5
• ZUEKSECYPXHXAQ-UHFFFAOYSA-N 1-pyrimidin-4-ylpiperidin-4-amine Chemical compound C1CC(N)CCN1C1=CC=NC=N1 ZUEKSECYPXHXAQ-UHFFFAOYSA-N 0.000 claims description 5
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 5
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
• 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 5
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 5
• 208000037803 restenosis Diseases 0.000 claims description 5
• 230000002792 vascular Effects 0.000 claims description 5
• IYCMYOWBZQNVBV-UHFFFAOYSA-N (1-propan-2-ylpiperidin-4-yl)methanamine Chemical compound CC(C)N1CCC(CN)CC1 IYCMYOWBZQNVBV-UHFFFAOYSA-N 0.000 claims description 4
• CZSRXHJVZUBEGW-UHFFFAOYSA-N 1,2-thiazolidine Chemical compound C1CNSC1 CZSRXHJVZUBEGW-UHFFFAOYSA-N 0.000 claims description 4
• 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 4
• ABADUMLIAZCWJD-UHFFFAOYSA-N 1,3-dioxole Chemical compound C1OC=CO1 ABADUMLIAZCWJD-UHFFFAOYSA-N 0.000 claims description 4
• ZDEGYYDOWMXDCH-UHFFFAOYSA-N 1-[2-[(5-chloropyridin-2-yl)amino]-2-oxoethyl]-5-methylsulfonyl-n-(1-propan-2-ylpiperidin-4-yl)indole-2-carboxamide Chemical compound C1CN(C(C)C)CCC1NC(=O)C1=CC2=CC(S(C)(=O)=O)=CC=C2N1CC(=O)NC1=CC=C(Cl)C=N1 ZDEGYYDOWMXDCH-UHFFFAOYSA-N 0.000 claims description 4
• JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 claims description 4
• MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims description 4
• KGWNRZLPXLBMPS-UHFFFAOYSA-N 2h-1,3-oxazine Chemical compound C1OC=CC=N1 KGWNRZLPXLBMPS-UHFFFAOYSA-N 0.000 claims description 4
• NTYABNDBNKVWOO-UHFFFAOYSA-N 2h-1,3-thiazine Chemical compound C1SC=CC=N1 NTYABNDBNKVWOO-UHFFFAOYSA-N 0.000 claims description 4
• YHWMFDLNZGIJSD-UHFFFAOYSA-N 2h-1,4-oxazine Chemical compound C1OC=CN=C1 YHWMFDLNZGIJSD-UHFFFAOYSA-N 0.000 claims description 4
• ZAISDHPZTZIFQF-UHFFFAOYSA-N 2h-1,4-thiazine Chemical compound C1SC=CN=C1 ZAISDHPZTZIFQF-UHFFFAOYSA-N 0.000 claims description 4
• BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 4
• XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 claims description 4
• GUUULVAMQJLDSY-UHFFFAOYSA-N 4,5-dihydro-1,2-thiazole Chemical compound C1CC=NS1 GUUULVAMQJLDSY-UHFFFAOYSA-N 0.000 claims description 4
• NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 4
• YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 4
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
• 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 4
• 230000020764 fibrinolysis Effects 0.000 claims description 4
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
• 125000005956 isoquinolyl group Chemical group 0.000 claims description 4
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
• MIJCTFQIMWKOJZ-UHFFFAOYSA-N n-(4-chlorophenyl)-2-[2-[4-(pyridin-4-ylamino)piperidine-1-carbonyl]indol-1-yl]acetamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)CN1C2=CC=CC=C2C=C1C(=O)N1CCC(NC=2C=CN=CC=2)CC1 MIJCTFQIMWKOJZ-UHFFFAOYSA-N 0.000 claims description 4
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 4
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
• 229930192474 thiophene Natural products 0.000 claims description 4
• 230000002537 thrombolytic effect Effects 0.000 claims description 4
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
• UOCPLRLVNRLSHU-UHFFFAOYSA-N (3-pyridin-4-yl-4,5-dihydro-1,2-oxazol-5-yl)methanamine Chemical compound O1C(CN)CC(C=2C=CN=CC=2)=N1 UOCPLRLVNRLSHU-UHFFFAOYSA-N 0.000 claims description 3
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
• 125000006565 (C4-C7) cyclic group Chemical group 0.000 claims description 3
• ZXVWFOMYPHVUGO-UHFFFAOYSA-N 1-(2-methylpropyl)piperidin-4-amine Chemical compound CC(C)CN1CCC(N)CC1 ZXVWFOMYPHVUGO-UHFFFAOYSA-N 0.000 claims description 3
• XUKZYTNPGQPSGF-UHFFFAOYSA-N 1-(3-chlorophenyl)indole-2-carboxylic acid Chemical compound OC(=O)C1=CC2=CC=CC=C2N1C1=CC=CC(Cl)=C1 XUKZYTNPGQPSGF-UHFFFAOYSA-N 0.000 claims description 3
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