ZA200200543B - Substituted oxoazaheterocyclyl compounds. - Google Patents

Info

Publication number

ZA200200543B

ZA200200543B ZA200200543A ZA200200543A ZA200200543B ZA 200200543 B ZA200200543 B ZA 200200543B ZA 200200543 A ZA200200543 A ZA 200200543A ZA 200200543 A ZA200200543 A ZA 200200543A ZA 200200543 B ZA200200543 B ZA 200200543B

Authority

ZA

South Africa

Prior art keywords

chloro

piperazin

amino

ylmethyl

quinazolin

Prior art date

1999-07-28

Links

• Espacenet
• Global Dossier
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims description 82
• -1 methoxyethylaminomethyl Chemical group 0.000 claims description 261
• 125000001072 heteroaryl group Chemical group 0.000 claims description 99
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 91
• 125000000623 heterocyclic group Chemical group 0.000 claims description 76
• 125000003118 aryl group Chemical group 0.000 claims description 59
• 229910052739 hydrogen Inorganic materials 0.000 claims description 59
• 239000001257 hydrogen Substances 0.000 claims description 59
• 125000000217 alkyl group Chemical group 0.000 claims description 57
• 229910052799 carbon Inorganic materials 0.000 claims description 54
• 229910052760 oxygen Inorganic materials 0.000 claims description 54
• 229910052717 sulfur Inorganic materials 0.000 claims description 53
• 150000002431 hydrogen Chemical class 0.000 claims description 50
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 45
• 125000004432 carbon atom Chemical group C* 0.000 claims description 45
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 43
• 150000003839 salts Chemical class 0.000 claims description 43
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 42
• 229910052757 nitrogen Inorganic materials 0.000 claims description 41
• 150000001721 carbon Chemical group 0.000 claims description 38
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 38
• 125000003107 substituted aryl group Chemical group 0.000 claims description 38
• 125000002947 alkylene group Chemical group 0.000 claims description 37
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 35
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 35
• 125000003545 alkoxy group Chemical group 0.000 claims description 31
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 30
• 150000001204 N-oxides Chemical class 0.000 claims description 24
• 125000002252 acyl group Chemical group 0.000 claims description 23
• 239000012453 solvate Substances 0.000 claims description 21
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 20
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
• 108010074860 Factor Xa Proteins 0.000 claims description 19
• 125000004442 acylamino group Chemical group 0.000 claims description 18
• 125000004414 alkyl thio group Chemical group 0.000 claims description 18
• 125000005843 halogen group Chemical group 0.000 claims description 18
• 125000005349 heteroarylcycloalkyl group Chemical group 0.000 claims description 18
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 17
• 229940002612 prodrug Drugs 0.000 claims description 17
• 239000000651 prodrug Substances 0.000 claims description 17
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 15
• 125000004450 alkenylene group Chemical group 0.000 claims description 14
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 14
• 125000004104 aryloxy group Chemical group 0.000 claims description 13
• 125000004419 alkynylene group Chemical group 0.000 claims description 12
• 125000004350 aryl cycloalkyl group Chemical group 0.000 claims description 12
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 11
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
• CZAAKPFIWJXPQT-UHFFFAOYSA-N quinazolin-2-amine Chemical compound C1=CC=CC2=NC(N)=NC=C21 CZAAKPFIWJXPQT-UHFFFAOYSA-N 0.000 claims description 9
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 8
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 8
• 229910052736 halogen Inorganic materials 0.000 claims description 8
• 150000002367 halogens Chemical group 0.000 claims description 8
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
• 230000002401 inhibitory effect Effects 0.000 claims description 8
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 7
• 125000005415 substituted alkoxy group Chemical group 0.000 claims description 7
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
• 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 6
• 150000002148 esters Chemical class 0.000 claims description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• 238000002360 preparation method Methods 0.000 claims description 5
• 125000001544 thienyl group Chemical group 0.000 claims description 5
• PLLLVRSRXFDRHN-UHFFFAOYSA-N 1h-pyrazole;thiophene Chemical compound C=1C=CSC=1.C=1C=NNC=1 PLLLVRSRXFDRHN-UHFFFAOYSA-N 0.000 claims description 4
• XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 claims description 4
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 4
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 4
• IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 4
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 4
• 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 4
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
• GBXYTRIBFXZUBS-UHFFFAOYSA-N oxadiazole;thiophene Chemical compound C=1C=CSC=1.C1=CON=N1 GBXYTRIBFXZUBS-UHFFFAOYSA-N 0.000 claims description 4
• KAVSMINTEBGDTI-UHFFFAOYSA-N pyridine;thiophene Chemical compound C=1C=CSC=1.C1=CC=NC=C1 KAVSMINTEBGDTI-UHFFFAOYSA-N 0.000 claims description 4
• JEJWGAXKVFYJDN-UHFFFAOYSA-N thiadiazole;thiophene Chemical compound C=1C=CSC=1.C1=CSN=N1 JEJWGAXKVFYJDN-UHFFFAOYSA-N 0.000 claims description 4
• HHNQDLUNMOECFS-UHFFFAOYSA-N thiophene;2h-triazole Chemical compound C=1C=CSC=1.C1=CNN=N1 HHNQDLUNMOECFS-UHFFFAOYSA-N 0.000 claims description 4
• ULIIZNSKJMOVMX-UHFFFAOYSA-N 1,2-oxazole;thiophene Chemical compound C=1C=CSC=1.C=1C=NOC=1 ULIIZNSKJMOVMX-UHFFFAOYSA-N 0.000 claims description 3
• LUEYUHCBBXWTQT-UHFFFAOYSA-N 4-phenyl-2h-triazole Chemical compound C1=NNN=C1C1=CC=CC=C1 LUEYUHCBBXWTQT-UHFFFAOYSA-N 0.000 claims description 3
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
• 125000004945 acylaminoalkyl group Chemical group 0.000 claims description 3
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 3
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 125000005242 carbamoyl alkyl group Chemical group 0.000 claims description 3
• 125000001041 indolyl group Chemical group 0.000 claims description 3
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 2
• 125000005354 acylalkyl group Chemical group 0.000 claims description 2
• 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 2
• 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 2
• 125000004076 pyridyl group Chemical group 0.000 claims description 2
• QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 claims 7
• SXJRFJQQWDUBFI-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-oxopiperazine-2-carboxylic acid Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CC(N(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)C(O)=O)=CC2=C1 SXJRFJQQWDUBFI-UHFFFAOYSA-N 0.000 claims 5
• 229930194542 Keto Natural products 0.000 claims 4
• 230000004962 physiological condition Effects 0.000 claims 4
• BVJOOFWNOSOSAN-LJQANCHMSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)sulfonyl]-6-(2-methylpropyl)piperazin-2-one Chemical compound ClC1=CC=C2NC(S(=O)(=O)N3C[C@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)CC(C)C)=CC2=C1 BVJOOFWNOSOSAN-LJQANCHMSA-N 0.000 claims 3
• YPRAQQUUXZEJAL-NRFANRHFSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)sulfonyl]-6-propan-2-ylpiperazin-2-one Chemical compound ClC1=CC=C2NC(S(=O)(=O)N3C[C@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)C(C)C)=CC2=C1 YPRAQQUUXZEJAL-NRFANRHFSA-N 0.000 claims 3
• FLWBPUYNYZDVAW-KRWDZBQOSA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-(methoxymethyl)piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3C[C@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)COC)=CC2=C1 FLWBPUYNYZDVAW-KRWDZBQOSA-N 0.000 claims 3
• JDYHHQBKBCKVIJ-ZDUSSCGKSA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-methylpiperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3C[C@@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)C)=CC2=C1 JDYHHQBKBCKVIJ-ZDUSSCGKSA-N 0.000 claims 3
• FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims 3
• 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 3
• 125000006515 benzyloxy alkyl group Chemical group 0.000 claims 3
• IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical compound O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 claims 3
• JQVUFHKXCOOAGG-OEMAIJDKSA-N (4r)-2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-(methoxymethyl)-6-oxopiperazin-1-yl]methyl]-4,5,6,7-tetrahydro-1,3-benzothiazole-4-carboxamide Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CC(N(C(=O)C3)CC=3SC=4CCC[C@H](C=4N=3)C(N)=O)COC)=CC2=C1 JQVUFHKXCOOAGG-OEMAIJDKSA-N 0.000 claims 2
• WMVJTEVXTPWTIO-QGZVFWFLSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-benzimidazol-2-yl)sulfonyl]-6-(2-methylpropyl)piperazin-2-one Chemical compound C1=C(Cl)C=C2NC(S(=O)(=O)N3C[C@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)CC(C)C)=NC2=C1 WMVJTEVXTPWTIO-QGZVFWFLSA-N 0.000 claims 2
• YRUYPOCCFXKUGQ-FQEVSTJZSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-benzimidazol-2-yl)sulfonyl]-6-propan-2-ylpiperazin-2-one Chemical compound C1=C(Cl)C=C2NC(S(=O)(=O)N3C[C@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)C(C)C)=NC2=C1 YRUYPOCCFXKUGQ-FQEVSTJZSA-N 0.000 claims 2
• CFDFZWBTINHDGA-IBGZPJMESA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-(2-methylpropyl)piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3C[C@@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)CC(C)C)=CC2=C1 CFDFZWBTINHDGA-IBGZPJMESA-N 0.000 claims 2
• AFOIEYGNOGPVNW-HNNXBMFYSA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-benzimidazol-2-yl)sulfonyl]-6-(methoxymethyl)piperazin-2-one Chemical compound C1=C(Cl)C=C2NC(S(=O)(=O)N3C[C@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)COC)=NC2=C1 AFOIEYGNOGPVNW-HNNXBMFYSA-N 0.000 claims 2
• RCXOEPBIGDLMFU-IBGZPJMESA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-indol-2-yl)sulfonyl]-6-(2-methylpropyl)piperazin-2-one Chemical compound C1=C(Cl)C=C2NC(S(=O)(=O)N3C[C@@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)CC(C)C)=CC2=C1 RCXOEPBIGDLMFU-IBGZPJMESA-N 0.000 claims 2
• REAOXGUQRZZDRL-UHFFFAOYSA-N 1,1-diphenyl-N-(1H-pyrrolo[3,2-b]pyridin-2-yl)methanimine Chemical compound C(C1=CC=CC=C1)(C1=CC=CC=C1)=NC1=CC2=C(C=CC=N2)N1 REAOXGUQRZZDRL-UHFFFAOYSA-N 0.000 claims 2
• WSNLTKPLNJAMCS-UHFFFAOYSA-N 1-(methoxymethyl)piperazin-2-one Chemical compound COCN1CCNCC1=O WSNLTKPLNJAMCS-UHFFFAOYSA-N 0.000 claims 2
• UXCDAPQWTIOGBJ-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)sulfonyl]piperazin-2-one Chemical compound ClC1=CC=C2NC(S(=O)(=O)N3CCN(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)=CC2=C1 UXCDAPQWTIOGBJ-UHFFFAOYSA-N 0.000 claims 2
• WATFFCBCBMOTJR-UHFFFAOYSA-N 2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-6,7-dihydro-5h-1,3-benzothiazol-4-one Chemical compound S1C2=CC(Cl)=CC=C2C=C1S(=O)(=O)N(CC1=O)CCN1CC(S1)=NC2=C1CCCC2=O WATFFCBCBMOTJR-UHFFFAOYSA-N 0.000 claims 2
• CCXQCOZBEONOFB-UHFFFAOYSA-N 2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-n,n-dimethyl-1,3-thiazole-4-carboxamide Chemical compound CN(C)C(=O)C1=CSC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=N1 CCXQCOZBEONOFB-UHFFFAOYSA-N 0.000 claims 2
• WQAJCBIDKVJMBV-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[[1-[2-(2-hydroxyethylamino)pyrimidin-4-yl]piperidin-4-yl]methyl]piperazin-2-one Chemical compound OCCNC1=NC=CC(N2CCC(CN3C(CN(CC3)S(=O)(=O)C=3SC4=CC(Cl)=CC=C4C=3)=O)CC2)=N1 WQAJCBIDKVJMBV-UHFFFAOYSA-N 0.000 claims 2
• SWQWTDAWUSBMGA-UHFFFAOYSA-N 5-chloro-1,3-thiazol-2-amine Chemical compound NC1=NC=C(Cl)S1 SWQWTDAWUSBMGA-UHFFFAOYSA-N 0.000 claims 2
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 2
• QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims 2
• MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims 2
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
• VPQAQEOATKTJSK-UHFFFAOYSA-N piperidine;pyrimidine Chemical compound C1CCNCC1.C1=CN=CN=C1 VPQAQEOATKTJSK-UHFFFAOYSA-N 0.000 claims 2
• NPQHGKXCYSHCLB-SFHVURJKSA-N (2s)-4-[(4-aminoquinazolin-7-yl)methyl]-n-(4-chlorophenyl)-2-(hydroxymethyl)-3-oxopiperazine-1-carboxamide Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C([C@@H]1CO)=O)CCN1C(=O)NC1=CC=C(Cl)C=C1 NPQHGKXCYSHCLB-SFHVURJKSA-N 0.000 claims 1
• LZWKVVOYZSPDLK-AWEZNQCLSA-N (2s)-4-[(4-aminoquinazolin-7-yl)methyl]-n-(5-bromo-1,3-thiazol-2-yl)-2-(methoxymethyl)-3-oxopiperazine-1-carboxamide Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)C(=O)NC1=NC=C(Br)S1 LZWKVVOYZSPDLK-AWEZNQCLSA-N 0.000 claims 1
• PEDPKCRXTVNVSD-HNNXBMFYSA-N (2s)-4-[(4-aminoquinazolin-7-yl)methyl]-n-(5-bromo-1,3-thiazol-2-yl)-3-oxo-2-propylpiperazine-1-carboxamide Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CCC)C(=O)NC1=NC=C(Br)S1 PEDPKCRXTVNVSD-HNNXBMFYSA-N 0.000 claims 1
• MXYZABNETCECPJ-MRXNPFEDSA-N (3r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-3-(methoxymethyl)piperazin-2-one Chemical compound N1([C@@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)C(=O)COC1=CC=C(Cl)S1 MXYZABNETCECPJ-MRXNPFEDSA-N 0.000 claims 1
• UKHYEXSTCVHYKA-QHCPKHFHSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-(4-imidazol-1-ylbenzoyl)-3-propylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CCC)C(=O)C(C=C1)=CC=C1N1C=CN=C1 UKHYEXSTCVHYKA-QHCPKHFHSA-N 0.000 claims 1
• ZGHRZYDUEORGRH-FQEVSTJZSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-(5-chloro-1-benzofuran-2-carbonyl)-3-propylpiperazin-2-one Chemical compound ClC1=CC=C2OC(C(=O)N3[C@H](C(N(CC=4C=C5N=CN=C(N)C5=CC=4)CC3)=O)CCC)=CC2=C1 ZGHRZYDUEORGRH-FQEVSTJZSA-N 0.000 claims 1
• XTUVGWUAGYHTME-FQEVSTJZSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-(6-chloro-1-benzofuran-2-carbonyl)-3-(2-methylsulfanylethyl)piperazin-2-one Chemical compound C1=C(Cl)C=C2OC(C(=O)N3[C@H](C(N(CC=4C=C5N=CN=C(N)C5=CC=4)CC3)=O)CCSC)=CC2=C1 XTUVGWUAGYHTME-FQEVSTJZSA-N 0.000 claims 1
• NJBMALYPNRWOPO-BDQAORGHSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-(6-chloro-1-benzofuran-2-carbonyl)-3-propylpiperazin-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=C(Cl)C=C2OC(C(=O)N3[C@H](C(N(CC=4C=C5N=CN=C(N)C5=CC=4)CC3)=O)CCC)=CC2=C1 NJBMALYPNRWOPO-BDQAORGHSA-N 0.000 claims 1
• DAHDSWRVSTXKNO-DEOSSOPVSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-(6-hydroxynaphthalene-2-carbonyl)-3-propylpiperazin-2-one Chemical compound C1=C(O)C=CC2=CC(C(=O)N3[C@H](C(N(CC=4C=C5N=CN=C(N)C5=CC=4)CC3)=O)CCC)=CC=C21 DAHDSWRVSTXKNO-DEOSSOPVSA-N 0.000 claims 1
• UONHNCBWQSHVBK-SFHVURJKSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(4-aminothieno[3,2-d]pyrimidin-6-yl)methyl]-3-(methoxymethyl)piperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3CCN(CC=4SC5=C(N)N=CN=C5C=4)[C@H](C3=O)COC)=CC=C21 UONHNCBWQSHVBK-SFHVURJKSA-N 0.000 claims 1
• NQCZNXOCIOBIHQ-QHCPKHFHSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)methyl]-3-(2-methylsulfanylethyl)piperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3CCN(CC=4NC5=CC=C(Cl)C=C5C=4)[C@H](C3=O)CCSC)=CC=C21 NQCZNXOCIOBIHQ-QHCPKHFHSA-N 0.000 claims 1
• UFQAJBVMPZLQEE-VWLOTQADSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(7-chloroisoquinolin-3-yl)methyl]-3-(2-methylpropyl)piperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3CCN(CC=4N=CC5=CC(Cl)=CC=C5C=4)[C@H](C3=O)CC(C)C)=CC=C21 UFQAJBVMPZLQEE-VWLOTQADSA-N 0.000 claims 1
• USJMUPNRINRCNW-KRWDZBQOSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(2-amino-1,3-thiazol-4-yl)acetyl]-3-propylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CCC)C(=O)CC1=CSC(N)=N1 USJMUPNRINRCNW-KRWDZBQOSA-N 0.000 claims 1
• PFZSMLHMQHJNJB-SFHVURJKSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-3-(2-methylpropyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CC(C)C)C(=O)COC1=CC=C(Cl)S1 PFZSMLHMQHJNJB-SFHVURJKSA-N 0.000 claims 1
• SICAEVPEPWTQDS-KRWDZBQOSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-3-[(dimethylamino)methyl]piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CN(C)C)C(=O)COC1=CC=C(Cl)S1 SICAEVPEPWTQDS-KRWDZBQOSA-N 0.000 claims 1
• JBPPHJOLTWFYEQ-INIZCTEOSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(6-chloropyrazin-2-yl)oxyacetyl]-3-(methoxymethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)C(=O)COC1=CN=CC(Cl)=N1 JBPPHJOLTWFYEQ-INIZCTEOSA-N 0.000 claims 1
• VCCQPBXDRDSSCK-AWEZNQCLSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-[(5-amino-1,3,4-thiadiazol-2-yl)sulfanyl]acetyl]-3-(methoxymethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)C(=O)CSC1=NN=C(N)S1 VCCQPBXDRDSSCK-AWEZNQCLSA-N 0.000 claims 1
• PWEIMMCYMNAZHU-HNNXBMFYSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-[(5-amino-1,3,4-thiadiazol-2-yl)sulfanyl]acetyl]-3-propylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CCC)C(=O)CSC1=NN=C(N)S1 PWEIMMCYMNAZHU-HNNXBMFYSA-N 0.000 claims 1
• JHQIOJZCXJPJHV-FQEVSTJZSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(4-chlorothiophen-2-yl)prop-2-enoyl]-3-(2-methoxyethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CCOC)C(=O)C=CC1=CC(Cl)=CS1 JHQIOJZCXJPJHV-FQEVSTJZSA-N 0.000 claims 1
• XDTDNCIISWGSFW-SFHVURJKSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(4-chlorothiophen-2-yl)prop-2-enoyl]-3-(hydroxymethyl)piperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C([C@@H]1CO)=O)CCN1C(=O)C=CC1=CC(Cl)=CS1 XDTDNCIISWGSFW-SFHVURJKSA-N 0.000 claims 1
• LBIUTUCBLSATKR-KRWDZBQOSA-N (3s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)prop-2-enoyl]-3-(hydroxymethyl)piperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C([C@@H]1CO)=O)CCN1C(=O)C=CC1=CC=C(Cl)S1 LBIUTUCBLSATKR-KRWDZBQOSA-N 0.000 claims 1
• IIBVYWFOWLCCBZ-YFKPBYRVSA-N (3s)-3-(methoxymethyl)piperazin-2-one Chemical compound COC[C@@H]1NCCNC1=O IIBVYWFOWLCCBZ-YFKPBYRVSA-N 0.000 claims 1
• KVEVMDOCIXZXFU-SANMLTNESA-N (3s)-4-[(5-chloro-1h-indol-2-yl)methyl]-1-[[4-(6-oxo-1h-pyridin-3-yl)phenyl]methyl]-3-propylpiperazin-2-one Chemical compound C=1C2=CC(Cl)=CC=C2NC=1CN([C@H](C1=O)CCC)CCN1CC(C=C1)=CC=C1C=1C=CC(=O)NC=1 KVEVMDOCIXZXFU-SANMLTNESA-N 0.000 claims 1
• UVKNAKBPGNSUIV-NDEPHWFRSA-N (3s)-4-[(7-chloroisoquinolin-3-yl)methyl]-1-[[4-(6-methoxypyridin-3-yl)phenyl]methyl]-3-propylpiperazin-2-one Chemical compound C=1C2=CC=C(Cl)C=C2C=NC=1CN([C@H](C1=O)CCC)CCN1CC(C=C1)=CC=C1C1=CC=C(OC)N=C1 UVKNAKBPGNSUIV-NDEPHWFRSA-N 0.000 claims 1
• GVGWTUVZAWCGGI-INIZCTEOSA-N (3s)-4-[2-(5-chlorothiophen-2-yl)oxyacetyl]-1-[[2-[2-(dimethylamino)ethylamino]pyrimidin-5-yl]methyl]-3-(methoxymethyl)piperazin-2-one Chemical compound C=1C=C(Cl)SC=1OCC(=O)N([C@H](C1=O)COC)CCN1CC1=CN=C(NCCN(C)C)N=C1 GVGWTUVZAWCGGI-INIZCTEOSA-N 0.000 claims 1
• QVOWSXWJCKPWNF-FQEVSTJZSA-N (3s)-4-[3-(6-aminopyridin-3-yl)prop-2-enoyl]-1-[(4-aminoquinazolin-7-yl)methyl]-3-(2-methoxyethyl)piperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CCOC)C(=O)C=CC1=CC=C(N)N=C1 QVOWSXWJCKPWNF-FQEVSTJZSA-N 0.000 claims 1
• PBNALOSNDBJGPY-QFIPXVFZSA-N (3s)-4-[3-(6-aminopyridin-3-yl)propanoyl]-3-(methoxymethyl)-1-[[4-(6-oxo-1h-pyridin-3-yl)phenyl]methyl]piperazin-2-one Chemical compound C=1C=C(N)N=CC=1CCC(=O)N([C@H](C1=O)COC)CCN1CC(C=C1)=CC=C1C=1C=CC(=O)NC=1 PBNALOSNDBJGPY-QFIPXVFZSA-N 0.000 claims 1
• LGCCNIXEXADPDD-LIRRHRJNSA-N (3s,6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[2-(5-chlorothiophen-3-yl)oxyacetyl]-6-methyl-3-propylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)[C@@H](C)C1)=O)CCC)C(=O)COC1=CSC(Cl)=C1 LGCCNIXEXADPDD-LIRRHRJNSA-N 0.000 claims 1
• LUGWIZQXSYDJDF-BTYIYWSLSA-N (3s,6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(4-chlorothiophen-2-yl)prop-2-enoyl]-6-methyl-3-propylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)[C@@H](C)C1)=O)CCC)C(=O)C=CC1=CC(Cl)=CS1 LUGWIZQXSYDJDF-BTYIYWSLSA-N 0.000 claims 1
• ONDMRPOZZIDTRB-YWZLYKJASA-N (3s,6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[3-(5-chlorothiophen-2-yl)prop-2-enoyl]-6-methyl-3-propylpiperazin-2-one Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)[C@@H](C)C1)=O)CCC)C(=O)C=CC1=CC=C(Cl)S1 ONDMRPOZZIDTRB-YWZLYKJASA-N 0.000 claims 1
• UTCXKEYSWPZQAZ-QGZVFWFLSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)sulfonyl]-6-(methoxymethyl)piperazin-2-one Chemical compound ClC1=CC=C2NC(S(=O)(=O)N3C[C@@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)COC)=CC2=C1 UTCXKEYSWPZQAZ-QGZVFWFLSA-N 0.000 claims 1
• FLWBPUYNYZDVAW-QGZVFWFLSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-(methoxymethyl)piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3C[C@@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)COC)=CC2=C1 FLWBPUYNYZDVAW-QGZVFWFLSA-N 0.000 claims 1
• QVZKFTXRRXJDLI-LJQANCHMSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-[(propan-2-ylamino)methyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3C[C@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)CNC(C)C)=CC2=C1 QVZKFTXRRXJDLI-LJQANCHMSA-N 0.000 claims 1
• JDYHHQBKBCKVIJ-CYBMUJFWSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-methylpiperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3C[C@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)C)=CC2=C1 JDYHHQBKBCKVIJ-CYBMUJFWSA-N 0.000 claims 1
• ILWNJPBQNWSXDJ-FQEVSTJZSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-propan-2-ylpiperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3C[C@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)C(C)C)=CC2=C1 ILWNJPBQNWSXDJ-FQEVSTJZSA-N 0.000 claims 1
• AFOIEYGNOGPVNW-OAHLLOKOSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-benzimidazol-2-yl)sulfonyl]-6-(methoxymethyl)piperazin-2-one Chemical compound C1=C(Cl)C=C2NC(S(=O)(=O)N3C[C@@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)COC)=NC2=C1 AFOIEYGNOGPVNW-OAHLLOKOSA-N 0.000 claims 1
• YRMPXIRUPGIBLA-GFCCVEGCSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-benzimidazol-2-yl)sulfonyl]-6-methylpiperazin-2-one Chemical compound C1=C(Cl)C=C2NC(S(=O)(=O)N3C[C@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)C)=NC2=C1 YRMPXIRUPGIBLA-GFCCVEGCSA-N 0.000 claims 1
• RCXOEPBIGDLMFU-LJQANCHMSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-indol-2-yl)sulfonyl]-6-(2-methylpropyl)piperazin-2-one Chemical compound C1=C(Cl)C=C2NC(S(=O)(=O)N3C[C@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)CC(C)C)=CC2=C1 RCXOEPBIGDLMFU-LJQANCHMSA-N 0.000 claims 1
• TWKRFZFCDFYWDU-CYBMUJFWSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-indol-2-yl)sulfonyl]-6-methylpiperazin-2-one Chemical compound C1=C(Cl)C=C2NC(S(=O)(=O)N3C[C@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)C)=CC2=C1 TWKRFZFCDFYWDU-CYBMUJFWSA-N 0.000 claims 1
• UZZJCFODHGBNAP-QGZVFWFLSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-6-(ethoxymethyl)piperazin-2-one Chemical compound C([C@@H](N(C(=O)C1)CC=2C=C3N=CN=C(N)C3=CC=2)COCC)N1CC(=NO1)C=C1C1=CC=C(Cl)S1 UZZJCFODHGBNAP-QGZVFWFLSA-N 0.000 claims 1
• ZDACGCXWKCRRPS-JOCHJYFZSA-N (6r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-6-(phenylmethoxymethyl)piperazin-2-one Chemical compound C([C@@H]1N(C(CN(CC2=NOC(=C2)C=2SC(Cl)=CC=2)C1)=O)CC=1C=C2N=CN=C(C2=CC=1)N)OCC1=CC=CC=C1 ZDACGCXWKCRRPS-JOCHJYFZSA-N 0.000 claims 1
• GHQVQVWNSAUJDO-QGZVFWFLSA-N (6r)-4-[(5-chloro-1h-indol-2-yl)sulfonyl]-1-[[1-[2-(dimethylamino)pyrimidin-4-yl]piperidin-4-yl]methyl]-6-methylpiperazin-2-one Chemical compound C([C@H]1C)N(S(=O)(=O)C=2NC3=CC=C(Cl)C=C3C=2)CC(=O)N1CC(CC1)CCN1C1=CC=NC(N(C)C)=N1 GHQVQVWNSAUJDO-QGZVFWFLSA-N 0.000 claims 1
• KIVLFZYOQQSSHW-QGZVFWFLSA-N (6r)-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[[1-[2-(dimethylamino)pyrimidin-4-yl]piperidin-4-yl]methyl]-6-methylpiperazin-2-one Chemical compound C([C@H]1C)N(S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)CC(=O)N1CC(CC1)CCN1C1=CC=NC(N(C)C)=N1 KIVLFZYOQQSSHW-QGZVFWFLSA-N 0.000 claims 1
• FHSBXUVKNRVGGG-MRXNPFEDSA-N (6r)-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-(methoxymethyl)-1-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-ylmethyl)piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3C[C@@H](N(C(=O)C3)CC=3SC=4CCCCC=4N=3)COC)=CC2=C1 FHSBXUVKNRVGGG-MRXNPFEDSA-N 0.000 claims 1
• SUCXPXLCKUQNSG-LJQANCHMSA-N (6r)-4-[(6-chloro-1h-benzimidazol-2-yl)sulfonyl]-1-[[1-[2-(dimethylamino)pyrimidin-4-yl]piperidin-4-yl]methyl]-6-(methoxymethyl)piperazin-2-one Chemical compound C([C@@H]1COC)N(S(=O)(=O)C=2NC3=CC(Cl)=CC=C3N=2)CC(=O)N1CC(CC1)CCN1C1=CC=NC(N(C)C)=N1 SUCXPXLCKUQNSG-LJQANCHMSA-N 0.000 claims 1
• BVJOOFWNOSOSAN-IBGZPJMESA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)sulfonyl]-6-(2-methylpropyl)piperazin-2-one Chemical compound ClC1=CC=C2NC(S(=O)(=O)N3C[C@@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)CC(C)C)=CC2=C1 BVJOOFWNOSOSAN-IBGZPJMESA-N 0.000 claims 1
• UTCXKEYSWPZQAZ-KRWDZBQOSA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)sulfonyl]-6-(methoxymethyl)piperazin-2-one Chemical compound ClC1=CC=C2NC(S(=O)(=O)N3C[C@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)COC)=CC2=C1 UTCXKEYSWPZQAZ-KRWDZBQOSA-N 0.000 claims 1
• YVPJSNWYWPVMPW-IBGZPJMESA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)sulfonyl]-6-[(propan-2-ylamino)methyl]piperazin-2-one Chemical compound ClC1=CC=C2NC(S(=O)(=O)N3C[C@@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)CNC(C)C)=CC2=C1 YVPJSNWYWPVMPW-IBGZPJMESA-N 0.000 claims 1
• BNQVIOJIVRWRHU-ZDUSSCGKSA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)sulfonyl]-6-methylpiperazin-2-one Chemical compound ClC1=CC=C2NC(S(=O)(=O)N3C[C@@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)C)=CC2=C1 BNQVIOJIVRWRHU-ZDUSSCGKSA-N 0.000 claims 1
• ZWBMNNLADQIJPN-FQEVSTJZSA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-(pyrrolidin-1-ylmethyl)piperazin-2-one Chemical compound C([C@@H]1N(C(CN(C1)S(=O)(=O)C=1SC2=CC(Cl)=CC=C2C=1)=O)CC=1C=C2N=CN=C(C2=CC=1)N)N1CCCC1 ZWBMNNLADQIJPN-FQEVSTJZSA-N 0.000 claims 1
• UBACQOPDLNXNRL-NRFANRHFSA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-[(2-propan-2-yloxyethylamino)methyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3C[C@@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)CNCCOC(C)C)=CC2=C1 UBACQOPDLNXNRL-NRFANRHFSA-N 0.000 claims 1
• QVZKFTXRRXJDLI-IBGZPJMESA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-[(propan-2-ylamino)methyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3C[C@@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)CNC(C)C)=CC2=C1 QVZKFTXRRXJDLI-IBGZPJMESA-N 0.000 claims 1
• CVPJYLZMAJIUOO-SFHVURJKSA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-benzimidazol-2-yl)sulfonyl]-6-(pyrrolidin-1-ylmethyl)piperazin-2-one Chemical compound C([C@@H]1N(C(CN(C1)S(=O)(=O)C=1NC2=CC(Cl)=CC=C2N=1)=O)CC=1C=C2N=CN=C(C2=CC=1)N)N1CCCC1 CVPJYLZMAJIUOO-SFHVURJKSA-N 0.000 claims 1
• YRMPXIRUPGIBLA-LBPRGKRZSA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-benzimidazol-2-yl)sulfonyl]-6-methylpiperazin-2-one Chemical compound C1=C(Cl)C=C2NC(S(=O)(=O)N3C[C@@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)C)=NC2=C1 YRMPXIRUPGIBLA-LBPRGKRZSA-N 0.000 claims 1
• YRUYPOCCFXKUGQ-HXUWFJFHSA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-benzimidazol-2-yl)sulfonyl]-6-propan-2-ylpiperazin-2-one Chemical compound C1=C(Cl)C=C2NC(S(=O)(=O)N3C[C@@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)C(C)C)=NC2=C1 YRUYPOCCFXKUGQ-HXUWFJFHSA-N 0.000 claims 1
• PYKCBKZDYWPYNB-KRWDZBQOSA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-indol-2-yl)sulfonyl]-6-(methoxymethyl)piperazin-2-one Chemical compound C1=C(Cl)C=C2NC(S(=O)(=O)N3C[C@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)COC)=CC2=C1 PYKCBKZDYWPYNB-KRWDZBQOSA-N 0.000 claims 1
• HZHRIYSVCLZNNH-IBGZPJMESA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-indol-2-yl)sulfonyl]-6-[(propan-2-ylamino)methyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2NC(S(=O)(=O)N3C[C@@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)CNC(C)C)=CC2=C1 HZHRIYSVCLZNNH-IBGZPJMESA-N 0.000 claims 1
• HMRPAOMZDREQHD-OAQYLSRUSA-N (6s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-indol-2-yl)sulfonyl]-6-propan-2-ylpiperazin-2-one Chemical compound C1=C(Cl)C=C2NC(S(=O)(=O)N3C[C@@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)C(C)C)=CC2=C1 HMRPAOMZDREQHD-OAQYLSRUSA-N 0.000 claims 1
• VJZHTDSMEAFUAW-SFHVURJKSA-N (6s)-6-(aminomethyl)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)methyl]piperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3C(=O)CN(CC=4NC5=CC=C(Cl)C=C5C=4)C[C@@H]3CN)=CC=C21 VJZHTDSMEAFUAW-SFHVURJKSA-N 0.000 claims 1
• RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 claims 1
• XLHUBROMZOAQMV-UHFFFAOYSA-N 1,4-benzosemiquinone Chemical group [O]C1=CC=C(O)C=C1 XLHUBROMZOAQMV-UHFFFAOYSA-N 0.000 claims 1
• YULBVDIZTAMXKS-UHFFFAOYSA-N 1-(2-methylpropyl)piperazin-2-one Chemical compound CC(C)CN1CCNCC1=O YULBVDIZTAMXKS-UHFFFAOYSA-N 0.000 claims 1
• PAVDLYMVFNUTSN-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-(2-piperidin-3-yloxyacetyl)piperazin-2-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1)=O)CCN1C(=O)COC1CCCNC1 PAVDLYMVFNUTSN-UHFFFAOYSA-N 0.000 claims 1
• GXPSLBFHCWQTLO-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(2-chloroimidazo[1,2-a]pyridin-7-yl)methyl]piperazin-2-one Chemical compound C1=CN2C=C(Cl)N=C2C=C1CN(CC1=O)CCN1CC1=CC=C2C(N)=NC=NC2=C1 GXPSLBFHCWQTLO-UHFFFAOYSA-N 0.000 claims 1
• BCSJWMNINIYXSJ-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(3,5-dichloro-1h-indol-2-yl)methyl]piperazin-2-one Chemical compound N1C2=CC=C(Cl)C=C2C(Cl)=C1CN(CC1=O)CCN1CC1=CC=C2C(N)=NC=NC2=C1 BCSJWMNINIYXSJ-UHFFFAOYSA-N 0.000 claims 1
• MHSZEDPAOYJKMP-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(3-bromo-5-chloro-1h-indol-2-yl)methyl]piperazin-2-one Chemical compound N1C2=CC=C(Cl)C=C2C(Br)=C1CN(CC1=O)CCN1CC1=CC=C2C(N)=NC=NC2=C1 MHSZEDPAOYJKMP-UHFFFAOYSA-N 0.000 claims 1
• NURCRLMTZDSNCX-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)methyl]-6-(2-methylpropyl)piperazin-2-one Chemical compound NC1=NC=NC2=CC(CN3C(=O)CN(CC=4NC5=CC=C(Cl)C=C5C=4)CC3CC(C)C)=CC=C21 NURCRLMTZDSNCX-UHFFFAOYSA-N 0.000 claims 1
• QBZNNMLBGQRFHR-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(7-chloroisoquinolin-3-yl)methyl]-4a,5,6,7,8,8a-hexahydro-3h-quinoxalin-2-one Chemical compound C1=C(Cl)C=C2C=NC(CN3C4CCCCC4N(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)=CC2=C1 QBZNNMLBGQRFHR-UHFFFAOYSA-N 0.000 claims 1
• YFUKVRGSOSXBNR-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]piperazine-2,3-dione Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C(C1=O)=O)CCN1CC(=NO1)C=C1C1=CC=C(Cl)S1 YFUKVRGSOSXBNR-UHFFFAOYSA-N 0.000 claims 1
• XYPCPKUUOJPTJB-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-4-[[5-chloro-3-[(dimethylamino)methyl]-1h-indol-2-yl]methyl]piperazin-2-one Chemical compound N1C2=CC=C(Cl)C=C2C(CN(C)C)=C1CN1CC(=O)N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1 XYPCPKUUOJPTJB-UHFFFAOYSA-N 0.000 claims 1
• NIEWQIUSHZNFEZ-UHFFFAOYSA-N 1-[(4-aminoquinazolin-7-yl)methyl]-6-methyl-3-propylpiperazin-2-one Chemical compound O=C1C(CCC)NCC(C)N1CC1=CC=C(C(N)=NC=N2)C2=C1 NIEWQIUSHZNFEZ-UHFFFAOYSA-N 0.000 claims 1
• WSGIXMSIZCPDHM-UHFFFAOYSA-N 1-[4-[(4-aminoquinazolin-7-yl)methyl]-3-oxo-2-propylpiperazin-1-yl]-3-(3-chlorophenyl)propane-1,3-dione Chemical compound C1CN(CC=2C=C3N=CN=C(N)C3=CC=2)C(=O)C(CCC)N1C(=O)CC(=O)C1=CC=CC(Cl)=C1 WSGIXMSIZCPDHM-UHFFFAOYSA-N 0.000 claims 1
• KZMYXJMZEQVWLN-UHFFFAOYSA-N 1-[4-[(4-aminoquinazolin-7-yl)methyl]-3-oxo-2-propylpiperazin-1-yl]-3-(4-hydroxyphenyl)propane-1,3-dione Chemical compound C1CN(CC=2C=C3N=CN=C(N)C3=CC=2)C(=O)C(CCC)N1C(=O)CC(=O)C1=CC=C(O)C=C1 KZMYXJMZEQVWLN-UHFFFAOYSA-N 0.000 claims 1
• QHCJJDVEXUJHGQ-UHFFFAOYSA-N 1-[4-[(4-aminoquinazolin-7-yl)methyl]-3-oxo-2-propylpiperazin-1-yl]-3-(5-chlorothiophen-2-yl)propane-1,3-dione Chemical compound C1CN(CC=2C=C3N=CN=C(N)C3=CC=2)C(=O)C(CCC)N1C(=O)CC(=O)C1=CC=C(Cl)S1 QHCJJDVEXUJHGQ-UHFFFAOYSA-N 0.000 claims 1
• MQUKKRZKNMMSLU-UHFFFAOYSA-N 1-[[4-(1-adamantyl)-1,3-thiazol-2-yl]methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]piperazin-2-one Chemical compound C1C(C2)CC(C3)CC2CC13C1=CSC(CN2CCN(CC2=O)S(=O)(=O)C2=CC3=CC=C(C=C3S2)Cl)=N1 MQUKKRZKNMMSLU-UHFFFAOYSA-N 0.000 claims 1
• KJCIMSSFGUGTGA-UHFFFAOYSA-N 1-methylpiperazin-2-one Chemical compound CN1CCNCC1=O KJCIMSSFGUGTGA-UHFFFAOYSA-N 0.000 claims 1
• HAMYXIGVVLQNKZ-SFHVURJKSA-N 2-[(2s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(5-chloro-1h-indol-2-yl)methyl]-6-oxopiperazin-2-yl]acetic acid Chemical compound ClC1=CC=C2NC(CN3C[C@H](CC(O)=O)N(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)=CC2=C1 HAMYXIGVVLQNKZ-SFHVURJKSA-N 0.000 claims 1
• WJZYSVHAHCGIIU-INIZCTEOSA-N 2-[(2s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-oxopiperazin-2-yl]acetic acid Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3C[C@H](CC(O)=O)N(C(C3)=O)CC=3C=C4N=CN=C(C4=CC=3)N)=CC2=C1 WJZYSVHAHCGIIU-INIZCTEOSA-N 0.000 claims 1
• UQSJBENEQYVQAZ-QHCPKHFHSA-N 2-[(2s)-4-[(4-aminoquinazolin-7-yl)methyl]-1-[(7-chloroisoquinolin-3-yl)methyl]-3-oxopiperazin-2-yl]-n-methylacetamide Chemical compound NC1=NC=NC2=CC(CN3CCN(CC=4N=CC5=CC(Cl)=CC=C5C=4)[C@H](C3=O)CC(=O)NC)=CC=C21 UQSJBENEQYVQAZ-QHCPKHFHSA-N 0.000 claims 1
• JMNXWPRLKZUFQK-UHFFFAOYSA-N 2-[2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-1,3-thiazol-4-yl]-n,n-dimethylacetamide Chemical compound CN(C)C(=O)CC1=CSC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=N1 JMNXWPRLKZUFQK-UHFFFAOYSA-N 0.000 claims 1
• ROVKSRJAIIXFFP-UHFFFAOYSA-N 2-[2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-1,3-thiazol-4-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CSC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=N1 ROVKSRJAIIXFFP-UHFFFAOYSA-N 0.000 claims 1
• NBEZZGRGQPOHCB-UHFFFAOYSA-N 2-[4-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]piperidin-1-yl]acetamide Chemical compound C1CN(CC(=O)N)CCC1CN1C(=O)CN(S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)CC1 NBEZZGRGQPOHCB-UHFFFAOYSA-N 0.000 claims 1
• PIZIWFOGALZFIJ-OAHLLOKOSA-N 2-[[(2r)-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-(methoxymethyl)-6-oxopiperazin-1-yl]methyl]-n,n-dimethyl-1,3-thiazole-4-carboxamide Chemical compound C([C@@H]1COC)N(S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)CC(=O)N1CC1=NC(C(=O)N(C)C)=CS1 PIZIWFOGALZFIJ-OAHLLOKOSA-N 0.000 claims 1
• MCUUGAMHPMUIPU-UHFFFAOYSA-N 2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-4,5,6,7-tetrahydro-1,3-benzothiazole-4-carboxamide Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CCN(C(C3)=O)CC=3SC=4CCCC(C=4N=3)C(=O)N)=CC2=C1 MCUUGAMHPMUIPU-UHFFFAOYSA-N 0.000 claims 1
• BZGZPQUEOZHRFI-UHFFFAOYSA-N 2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-5,6,7,8-tetrahydro-[1,3]thiazolo[4,5-c]azepin-4-one Chemical compound S1C2=CC(Cl)=CC=C2C=C1S(=O)(=O)N(CC1=O)CCN1CC(S1)=NC2=C1CCCNC2=O BZGZPQUEOZHRFI-UHFFFAOYSA-N 0.000 claims 1
• HXSYAXNITKIPPA-UHFFFAOYSA-N 2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-5,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridin-6-one Chemical compound C1C(=O)NCC(S2)=C1N=C2CN(C(=O)C1)CCN1S(=O)(=O)C1=CC2=CC=C(Cl)C=C2S1 HXSYAXNITKIPPA-UHFFFAOYSA-N 0.000 claims 1
• CVLUMURXNKJMGA-UHFFFAOYSA-N 2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-n-methyl-1,3-thiazole-4-carboxamide Chemical compound CNC(=O)C1=CSC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=N1 CVLUMURXNKJMGA-UHFFFAOYSA-N 0.000 claims 1
• PAOGMWFWHFSBRS-UHFFFAOYSA-N 2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-n-methyl-n-propan-2-yl-1,3-thiazole-4-carboxamide Chemical compound CC(C)N(C)C(=O)C1=CSC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=N1 PAOGMWFWHFSBRS-UHFFFAOYSA-N 0.000 claims 1
• XUSKVXOLHLAJOM-UHFFFAOYSA-N 2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-n-propan-2-yl-1,3-thiazole-4-carboxamide Chemical compound CC(C)NC(=O)C1=CSC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=N1 XUSKVXOLHLAJOM-UHFFFAOYSA-N 0.000 claims 1
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
• FIEYHAAMDAPVCH-UHFFFAOYSA-N 2-methyl-1h-quinazolin-4-one Chemical compound C1=CC=C2NC(C)=NC(=O)C2=C1 FIEYHAAMDAPVCH-UHFFFAOYSA-N 0.000 claims 1
• WHNQTHDJEZTVHS-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)propanoic acid Chemical compound C1=CC=C2SC(CCC(=O)O)=NC2=C1 WHNQTHDJEZTVHS-UHFFFAOYSA-N 0.000 claims 1
• VWEJJKNVTKJDAF-SFHVURJKSA-N 3-amino-5-[[(2s)-4-[(4-aminoquinazolin-7-yl)methyl]-2-(methoxymethyl)-3-oxopiperazin-1-yl]methyl]thiophene-2-carbonitrile Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)COC)CC1=CC(N)=C(C#N)S1 VWEJJKNVTKJDAF-SFHVURJKSA-N 0.000 claims 1
• MJOOKNHBSXXGRD-UHFFFAOYSA-N 4-(7-methoxynaphthalen-2-yl)sulfonyl-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound N1=CC=C2NC(CN3CCN(CC3=O)S(=O)(=O)C=3C=CC4=CC=C(C=C4C=3)OC)=CC2=C1 MJOOKNHBSXXGRD-UHFFFAOYSA-N 0.000 claims 1
• YGFJXYQOBMLQJE-UHFFFAOYSA-N 4-[(3-acetyl-5-chloro-1h-indol-2-yl)methyl]-1-[(4-aminoquinazolin-7-yl)methyl]piperazin-2-one Chemical compound N1C2=CC=C(Cl)C=C2C(C(=O)C)=C1CN1CC(=O)N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1 YGFJXYQOBMLQJE-UHFFFAOYSA-N 0.000 claims 1
• UGPDGFSYKBGAPB-UHFFFAOYSA-N 4-[(5-chloro-1h-indol-2-yl)sulfonyl]-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound N1=CC=C2NC(CN3CCN(CC3=O)S(=O)(=O)C=3NC4=CC=C(C=C4C=3)Cl)=CC2=C1 UGPDGFSYKBGAPB-UHFFFAOYSA-N 0.000 claims 1
• KTOJLHCKDVXMRK-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound N1=CC=C2NC(CN3CCN(CC3=O)S(=O)(=O)C3=CC4=CC=C(C=C4S3)Cl)=CC2=C1 KTOJLHCKDVXMRK-UHFFFAOYSA-N 0.000 claims 1
• VGXFIUFJTPNFJJ-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-(4,5,6,7-tetrahydro-[1,3]thiazolo[4,5-c]pyridin-2-ylmethyl)piperazin-2-one Chemical compound C1NCCC(S2)=C1N=C2CN(C(=O)C1)CCN1S(=O)(=O)C1=CC2=CC=C(Cl)C=C2S1 VGXFIUFJTPNFJJ-UHFFFAOYSA-N 0.000 claims 1
• GEWADIJSIYYLDE-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[(1-pyrazin-2-ylpiperidin-4-yl)methyl]piperazin-2-one Chemical compound S1C2=CC(Cl)=CC=C2C=C1S(=O)(=O)N(CC1=O)CCN1CC(CC1)CCN1C1=CN=CC=N1 GEWADIJSIYYLDE-UHFFFAOYSA-N 0.000 claims 1
• XCKKFGCBUJHAMH-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[(1-pyridin-2-ylpiperidin-4-yl)methyl]piperazin-2-one Chemical compound S1C2=CC(Cl)=CC=C2C=C1S(=O)(=O)N(CC1=O)CCN1CC(CC1)CCN1C1=CC=CC=N1 XCKKFGCBUJHAMH-UHFFFAOYSA-N 0.000 claims 1
• UXJDQBKFDIAYEN-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[(1-pyrimidin-2-ylpiperidin-4-yl)methyl]piperazin-2-one Chemical compound S1C2=CC(Cl)=CC=C2C=C1S(=O)(=O)N(CC1=O)CCN1CC(CC1)CCN1C1=NC=CC=N1 UXJDQBKFDIAYEN-UHFFFAOYSA-N 0.000 claims 1
• ZHFKLZCIFNYJIP-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[(4-hydroxy-4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)methyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CCN(C(C3)=O)CC=3SC=4CCCC(C=4N=3)O)=CC2=C1 ZHFKLZCIFNYJIP-UHFFFAOYSA-N 0.000 claims 1
• XGABEBXUGAILJN-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[(4-hydroxyimino-6,7-dihydro-5h-1,3-benzothiazol-2-yl)methyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CCN(C(C3)=O)CC=3SC=4CCCC(C=4N=3)=NO)=CC2=C1 XGABEBXUGAILJN-UHFFFAOYSA-N 0.000 claims 1
• KULHGWKQZSXESJ-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[(4-phenyl-1,3-thiazol-2-yl)methyl]piperazin-2-one Chemical compound S1C2=CC(Cl)=CC=C2C=C1S(=O)(=O)N(CC1=O)CCN1CC(SC=1)=NC=1C1=CC=CC=C1 KULHGWKQZSXESJ-UHFFFAOYSA-N 0.000 claims 1
• QRYNOSKGUPZZJU-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[(4-pyridin-3-yl-1,3-thiazol-2-yl)methyl]piperazin-2-one Chemical compound S1C2=CC(Cl)=CC=C2C=C1S(=O)(=O)N(CC1=O)CCN1CC(SC=1)=NC=1C1=CC=CN=C1 QRYNOSKGUPZZJU-UHFFFAOYSA-N 0.000 claims 1
• VITROVPYFUPPDL-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[(5-methyl-6,7-dihydro-4h-[1,3]thiazolo[4,5-c]pyridin-2-yl)methyl]piperazin-2-one Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CCN(C(C3)=O)CC=3SC=4CCN(CC=4N=3)C)=CC2=C1 VITROVPYFUPPDL-UHFFFAOYSA-N 0.000 claims 1
• GGDIVQHRVRCCIT-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[[1-[2-(3-morpholin-4-ylpropylamino)pyrimidin-4-yl]piperidin-4-yl]methyl]piperazin-2-one Chemical compound S1C2=CC(Cl)=CC=C2C=C1S(=O)(=O)N(CC1=O)CCN1CC(CC1)CCN1C(N=1)=CC=NC=1NCCCN1CCOCC1 GGDIVQHRVRCCIT-UHFFFAOYSA-N 0.000 claims 1
• FGOLRQBPQIURNV-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[[1-[2-[2-(2-oxoimidazolidin-1-yl)ethylamino]pyrimidin-4-yl]piperidin-4-yl]methyl]piperazin-2-one Chemical compound S1C2=CC(Cl)=CC=C2C=C1S(=O)(=O)N(CC1=O)CCN1CC(CC1)CCN1C(N=1)=CC=NC=1NCCN1CCNC1=O FGOLRQBPQIURNV-UHFFFAOYSA-N 0.000 claims 1
• AGUKJCQHGMNERN-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-1-[[1-[2-[4-(dimethylamino)butylamino]pyrimidin-4-yl]piperidin-4-yl]methyl]piperazin-2-one Chemical compound CN(C)CCCCNC1=NC=CC(N2CCC(CN3C(CN(CC3)S(=O)(=O)C=3SC4=CC(Cl)=CC=C4C=3)=O)CC2)=N1 AGUKJCQHGMNERN-UHFFFAOYSA-N 0.000 claims 1
• JOGYDPFHUFGMSS-UHFFFAOYSA-N 4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-(hydroxymethyl)-1-[(1-methylpyrrolo[3,2-c]pyridin-2-yl)methyl]piperazin-2-one Chemical compound N1=CC=C2N(C)C(CN3C(CN(CC3CO)S(=O)(=O)C=3SC4=CC(Cl)=CC=C4C=3)=O)=CC2=C1 JOGYDPFHUFGMSS-UHFFFAOYSA-N 0.000 claims 1
• RRTRVCANLBOYRA-SFHVURJKSA-N 4-[[(2s)-4-[(6-chloro-1h-benzimidazol-2-yl)sulfonyl]-2-(2-methylpropyl)-6-oxopiperazin-1-yl]methyl]benzenecarboximidamide Chemical compound C([C@@H]1CC(C)C)N(S(=O)(=O)C=2NC3=CC(Cl)=CC=C3N=2)CC(=O)N1CC1=CC=C(C(N)=N)C=C1 RRTRVCANLBOYRA-SFHVURJKSA-N 0.000 claims 1
• PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims 1
• PCHBMNCFKJKQPA-UHFFFAOYSA-N 5-chlorothiophen-2-amine Chemical compound NC1=CC=C(Cl)S1 PCHBMNCFKJKQPA-UHFFFAOYSA-N 0.000 claims 1
• BCJSJPTYQMJDHS-UHFFFAOYSA-N 6-(2h-pyridin-1-yl)pyridine-3-carboxylic acid Chemical compound N1=CC(C(=O)O)=CC=C1N1C=CC=CC1 BCJSJPTYQMJDHS-UHFFFAOYSA-N 0.000 claims 1
• NBACYZARLWTERV-QFIPXVFZSA-N 7-[[(2R)-4-[(6-chloro-1H-indol-2-yl)sulfonyl]-2-propan-2-ylpiperazin-1-yl]methyl]quinazolin-4-amine Chemical compound C1=C(Cl)C=C2NC(S(=O)(=O)N3C[C@H](N(CC3)CC=3C=C4N=CN=C(N)C4=CC=3)C(C)C)=CC2=C1 NBACYZARLWTERV-QFIPXVFZSA-N 0.000 claims 1
• CEGGGHGIZVSIIL-UHFFFAOYSA-N 7-[[4-[(5-chloro-1h-indol-2-yl)methyl]-2-(methoxymethyl)piperazin-1-yl]methyl]quinazolin-4-amine Chemical compound NC1=NC=NC2=CC(CN3CCN(CC=4NC5=CC=C(Cl)C=C5C=4)CC3COC)=CC=C21 CEGGGHGIZVSIIL-UHFFFAOYSA-N 0.000 claims 1
• STLZNZZZHQJODP-UHFFFAOYSA-N 9-[(4-aminoquinazolin-7-yl)methyl]-6,9-diazaspiro[4.5]decan-10-one Chemical compound C=1C=C2C(N)=NC=NC2=CC=1CN(C1=O)CCNC21CCCC2 STLZNZZZHQJODP-UHFFFAOYSA-N 0.000 claims 1
• CEEQCZMQIOGGFD-RXMQYKEDSA-N COC[C@H]1CN(C(O)=O)CC(=O)N1 Chemical compound COC[C@H]1CN(C(O)=O)CC(=O)N1 CEEQCZMQIOGGFD-RXMQYKEDSA-N 0.000 claims 1
• KLRIITUPJXUDHA-UHFFFAOYSA-N ClC1=CC=C(C=C1)NC(=O)N1CC(N(C2CCCCC12)CC1=CC=C2C(=NC=NC2=C1)N)=O Chemical compound ClC1=CC=C(C=C1)NC(=O)N1CC(N(C2CCCCC12)CC1=CC=C2C(=NC=NC2=C1)N)=O KLRIITUPJXUDHA-UHFFFAOYSA-N 0.000 claims 1
• IMLXPLXPDZURHG-IBGZPJMESA-N ClC1=CC=C(C=C1)NC(=O)N1[C@H](C(N(CC1)CC1=CC=C2C(=NC=NC2=C1)N)=O)CC(NC)=O Chemical compound ClC1=CC=C(C=C1)NC(=O)N1[C@H](C(N(CC1)CC1=CC=C2C(=NC=NC2=C1)N)=O)CC(NC)=O IMLXPLXPDZURHG-IBGZPJMESA-N 0.000 claims 1
• NMLDKAIVKXRACE-HNNXBMFYSA-N ClC1=CC=C(O1)NC(=O)N1[C@H](C(N(CC1)CC1=CC=C2C(=NC=NC2=C1)N)=O)COC Chemical compound ClC1=CC=C(O1)NC(=O)N1[C@H](C(N(CC1)CC1=CC=C2C(=NC=NC2=C1)N)=O)COC NMLDKAIVKXRACE-HNNXBMFYSA-N 0.000 claims 1
• OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 claims 1
• KNXBIADNKGGFFL-KRWDZBQOSA-N NC1=NC=NC2=CC(=CC=C12)CN1C([C@@H](N(CC1)C(COC1=NC(=CN=C1)Cl)=O)CCC)=O Chemical compound NC1=NC=NC2=CC(=CC=C12)CN1C([C@@H](N(CC1)C(COC1=NC(=CN=C1)Cl)=O)CCC)=O KNXBIADNKGGFFL-KRWDZBQOSA-N 0.000 claims 1
• RPVZYQKVBTZLJW-UHFFFAOYSA-N OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.Nc1ncnc2cc(CN3CCN(Cc4ccc(cn4)-c4ccc(Cl)s4)CC3=O)ccc12 Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.Nc1ncnc2cc(CN3CCN(Cc4ccc(cn4)-c4ccc(Cl)s4)CC3=O)ccc12 RPVZYQKVBTZLJW-UHFFFAOYSA-N 0.000 claims 1
• 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims 1
• PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 claims 1
• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 1
• 125000005605 benzo group Chemical group 0.000 claims 1
• YZEQSIBCEFTLDU-ZDUSSCGKSA-N benzyl (2s)-2-(2-methylsulfanylethyl)-3-oxopiperazine-1-carboxylate Chemical compound C1CNC(=O)[C@H](CCSC)N1C(=O)OCC1=CC=CC=C1 YZEQSIBCEFTLDU-ZDUSSCGKSA-N 0.000 claims 1
• SNXRMIWZSPUNPZ-UHFFFAOYSA-N benzyl 2-cyclopentyl-3-oxopiperazine-1-carboxylate Chemical compound C1CNC(=O)C(C2CCCC2)N1C(=O)OCC1=CC=CC=C1 SNXRMIWZSPUNPZ-UHFFFAOYSA-N 0.000 claims 1
• 125000005569 butenylene group Chemical group 0.000 claims 1
• 239000004202 carbamide Substances 0.000 claims 1
• HECNAKPQRJGHJE-UHFFFAOYSA-N ethyl 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1h-benzimidazol-2-yl)sulfonyl]-6-oxopiperazine-2-carboxylate Chemical compound C1=C(Cl)C=C2NC(S(=O)(=O)N3CC(N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)C(=O)OCC)=NC2=C1 HECNAKPQRJGHJE-UHFFFAOYSA-N 0.000 claims 1
• NNVWVFCPLVDZEZ-UHFFFAOYSA-N ethyl 3-[2-[[4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-2-oxopiperazin-1-yl]methyl]-1,3-thiazol-4-yl]-3-methylbutanoate Chemical compound CCOC(=O)CC(C)(C)C1=CSC(CN2C(CN(CC2)S(=O)(=O)C=2SC3=CC(Cl)=CC=C3C=2)=O)=N1 NNVWVFCPLVDZEZ-UHFFFAOYSA-N 0.000 claims 1
• ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 1
• UJGNKVLTNDDWET-UHFFFAOYSA-N methyl 1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-oxopiperazine-2-carboxylate Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3CC(N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)C(=O)OC)=CC2=C1 UJGNKVLTNDDWET-UHFFFAOYSA-N 0.000 claims 1
• NEGRUALBPOJNNR-UHFFFAOYSA-N methyl 1-[2-(5-chlorothiophen-2-yl)ethenylsulfonyl]-5-oxo-4-(1h-pyrrolo[3,2-c]pyridin-2-ylmethyl)piperazine-2-carboxylate Chemical compound COC(=O)C1CN(CC=2NC3=CC=NC=C3C=2)C(=O)CN1S(=O)(=O)C=CC1=CC=C(Cl)S1 NEGRUALBPOJNNR-UHFFFAOYSA-N 0.000 claims 1
• BBKNMQLOVMQZRO-UHFFFAOYSA-N methyl 6-chloro-1-benzofuran-2-carboxylate Chemical compound C1=C(Cl)C=C2OC(C(=O)OC)=CC2=C1 BBKNMQLOVMQZRO-UHFFFAOYSA-N 0.000 claims 1
• KRKPYFLIYNGWTE-UHFFFAOYSA-N n,o-dimethylhydroxylamine Chemical compound CNOC KRKPYFLIYNGWTE-UHFFFAOYSA-N 0.000 claims 1
• NEGMYNFLPUIGMK-DEOSSOPVSA-N n-[5-[3-[(2s)-4-[(4-aminoquinazolin-7-yl)methyl]-2-butyl-3-oxopiperazin-1-yl]-3-oxoprop-1-enyl]-6-methylpyridin-2-yl]acetamide Chemical compound N1([C@H](C(N(CC=2C=C3N=CN=C(N)C3=CC=2)CC1)=O)CCCC)C(=O)C=CC1=CC=C(NC(C)=O)N=C1C NEGMYNFLPUIGMK-DEOSSOPVSA-N 0.000 claims 1
• PBOOTINXTXIUJQ-NRFANRHFSA-N n-[[(2r)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[[5-(5-chlorothiophen-2-yl)-1,2-oxazol-3-yl]methyl]-6-oxopiperazin-2-yl]methyl]-n-(2-propan-2-yloxyethyl)formamide Chemical compound C([C@@H](N(C(=O)C1)CC=2C=C3N=CN=C(N)C3=CC=2)CN(CCOC(C)C)C=O)N1CC(=NO1)C=C1C1=CC=C(Cl)S1 PBOOTINXTXIUJQ-NRFANRHFSA-N 0.000 claims 1
• XHFGWHUWQXTGAT-UHFFFAOYSA-N n-methylpropan-2-amine Chemical compound CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 claims 1
• PDUSWJORWQPNRP-UHFFFAOYSA-N n-propan-2-ylacetamide Chemical compound CC(C)NC(C)=O PDUSWJORWQPNRP-UHFFFAOYSA-N 0.000 claims 1
• ZMUADARPXLFDHP-UHFFFAOYSA-N nitrocarbamic acid Chemical compound OC(=O)N[N+]([O-])=O ZMUADARPXLFDHP-UHFFFAOYSA-N 0.000 claims 1
• 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 1
• DRYRBWIFRVMRPV-UHFFFAOYSA-N quinazolin-4-amine Chemical compound C1=CC=C2C(N)=NC=NC2=C1 DRYRBWIFRVMRPV-UHFFFAOYSA-N 0.000 claims 1
• JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 1
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
• JXJFAWJZUYQMJC-IBGZPJMESA-N tert-butyl 2-[(2s)-1-[(4-aminoquinazolin-7-yl)methyl]-4-[(6-chloro-1-benzothiophen-2-yl)sulfonyl]-6-oxopiperazin-2-yl]acetate Chemical compound C1=C(Cl)C=C2SC(S(=O)(=O)N3C[C@@H](N(C(=O)C3)CC=3C=C4N=CN=C(N)C4=CC=3)CC(=O)OC(C)(C)C)=CC2=C1 JXJFAWJZUYQMJC-IBGZPJMESA-N 0.000 claims 1
• ILUBQLROFBISHX-UHFFFAOYSA-N tert-butyl 5-chloro-2-chlorosulfonylindole-1-carboxylate Chemical compound ClC1=CC=C2N(C(=O)OC(C)(C)C)C(S(Cl)(=O)=O)=CC2=C1 ILUBQLROFBISHX-UHFFFAOYSA-N 0.000 claims 1
• GBTWJDAEKNGADB-UHFFFAOYSA-N tert-butyl 5-methyl-3-oxo-2-propylpiperazine-1-carboxylate Chemical compound CCCC1N(C(=O)OC(C)(C)C)CC(C)NC1=O GBTWJDAEKNGADB-UHFFFAOYSA-N 0.000 claims 1
• CSWGIYZSJBBEKY-UHFFFAOYSA-N tert-butyl 6-chloro-2-chlorosulfonylindole-1-carboxylate Chemical compound C1=C(Cl)C=C2N(C(=O)OC(C)(C)C)C(S(Cl)(=O)=O)=CC2=C1 CSWGIYZSJBBEKY-UHFFFAOYSA-N 0.000 claims 1
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 1
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 49
• 108090000190 Thrombin Proteins 0.000 description 24
• 229960004072 thrombin Drugs 0.000 description 24
• 125000006413 ring segment Chemical group 0.000 description 22
• 239000002253 acid Substances 0.000 description 21
• 239000001301 oxygen Substances 0.000 description 19
• 125000003435 aroyl group Chemical group 0.000 description 17
• 125000001424 substituent group Chemical group 0.000 description 16
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 15
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 14
• 125000003282 alkyl amino group Chemical group 0.000 description 12
• 125000004122 cyclic group Chemical group 0.000 description 12
• 238000000034 method Methods 0.000 description 12
• 150000002923 oximes Chemical class 0.000 description 12
• 125000003342 alkenyl group Chemical group 0.000 description 10
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
• 239000011593 sulfur Substances 0.000 description 10
• 125000000464 thioxo group Chemical group S=* 0.000 description 10
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 9
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
• 241000534944 Thia Species 0.000 description 9
• 125000004434 sulfur atom Chemical group 0.000 description 9
• 208000007536 Thrombosis Diseases 0.000 description 8
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
• 125000005110 aryl thio group Chemical group 0.000 description 7
• 230000000694 effects Effects 0.000 description 7
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• 125000004644 alkyl sulfinyl group Chemical group 0.000 description 6
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 6
• 125000005239 aroylamino group Chemical group 0.000 description 6
• 125000005135 aryl sulfinyl group Chemical group 0.000 description 6
• 125000004391 aryl sulfonyl group Chemical group 0.000 description 6
• 239000002585 base Substances 0.000 description 6
• 239000012458 free base Substances 0.000 description 6
• 150000002430 hydrocarbons Chemical group 0.000 description 6
• RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 6
• 239000003112 inhibitor Substances 0.000 description 6
• 239000000543 intermediate Substances 0.000 description 6
• 239000000203 mixture Substances 0.000 description 6
• 238000011282 treatment Methods 0.000 description 6
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 5
• 230000015572 biosynthetic process Effects 0.000 description 5
• 239000011203 carbon fibre reinforced carbon Substances 0.000 description 5
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
• 230000005764 inhibitory process Effects 0.000 description 5
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
• 230000004913 activation Effects 0.000 description 4
• 230000006978 adaptation Effects 0.000 description 4
• 239000003146 anticoagulant agent Substances 0.000 description 4
• 239000003125 aqueous solvent Substances 0.000 description 4
• 238000006243 chemical reaction Methods 0.000 description 4
• 125000005150 heteroarylsulfinyl group Chemical group 0.000 description 4
• 239000003960 organic solvent Substances 0.000 description 4
• 125000006239 protecting group Chemical group 0.000 description 4
• 239000000243 solution Substances 0.000 description 4
• 239000002904 solvent Substances 0.000 description 4
• 238000002560 therapeutic procedure Methods 0.000 description 4
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
• 206010051055 Deep vein thrombosis Diseases 0.000 description 3
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
• 229940123583 Factor Xa inhibitor Drugs 0.000 description 3
• 108010049003 Fibrinogen Proteins 0.000 description 3
• 102000008946 Fibrinogen Human genes 0.000 description 3
• HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 3
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
• 241000124008 Mammalia Species 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• 150000007513 acids Chemical class 0.000 description 3
• 125000001931 aliphatic group Chemical group 0.000 description 3
• QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
• 229940127219 anticoagulant drug Drugs 0.000 description 3
• 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 3
• 125000004659 aryl alkyl thio group Chemical group 0.000 description 3
• 230000009286 beneficial effect Effects 0.000 description 3
• 230000023555 blood coagulation Effects 0.000 description 3
• 210000004027 cell Anatomy 0.000 description 3
• 125000001309 chloro group Chemical group Cl* 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
• 230000015271 coagulation Effects 0.000 description 3
• 238000005345 coagulation Methods 0.000 description 3
• 208000035475 disorder Diseases 0.000 description 3
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
• 229940012952 fibrinogen Drugs 0.000 description 3
• 125000001153 fluoro group Chemical group F* 0.000 description 3
• 229960002897 heparin Drugs 0.000 description 3
• 229920000669 heparin Polymers 0.000 description 3
• 125000005143 heteroarylsulfonyl group Chemical group 0.000 description 3
• 125000005368 heteroarylthio group Chemical group 0.000 description 3
• 238000004519 manufacturing process Methods 0.000 description 3
• 125000000446 sulfanediyl group Chemical group *S* 0.000 description 3
• 230000001732 thrombotic effect Effects 0.000 description 3
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
• HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 2
• 108010039209 Blood Coagulation Factors Proteins 0.000 description 2
• 102000015081 Blood Coagulation Factors Human genes 0.000 description 2
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
• 239000004215 Carbon black (E152) Substances 0.000 description 2
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
• 102000009123 Fibrin Human genes 0.000 description 2
• 108010073385 Fibrin Proteins 0.000 description 2
• BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 description 2
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
• 206010028980 Neoplasm Diseases 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• 108010094028 Prothrombin Proteins 0.000 description 2
• 102100027378 Prothrombin Human genes 0.000 description 2
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• 230000002159 abnormal effect Effects 0.000 description 2
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
• 230000003213 activating effect Effects 0.000 description 2
• 206010000891 acute myocardial infarction Diseases 0.000 description 2
• 239000003513 alkali Substances 0.000 description 2
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
• 150000001412 amines Chemical class 0.000 description 2
• 125000003277 amino group Chemical group 0.000 description 2
• 150000001450 anions Chemical class 0.000 description 2
• 210000001367 artery Anatomy 0.000 description 2
• 125000002102 aryl alkyloxo group Chemical group 0.000 description 2
• 125000004429 atom Chemical group 0.000 description 2
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
• 239000003114 blood coagulation factor Substances 0.000 description 2
• 125000001246 bromo group Chemical group Br* 0.000 description 2
• 201000011510 cancer Diseases 0.000 description 2
• 125000004181 carboxyalkyl group Chemical group 0.000 description 2
• 150000001768 cations Chemical class 0.000 description 2
• 239000003795 chemical substances by application Substances 0.000 description 2
• 230000001684 chronic effect Effects 0.000 description 2
• 238000003776 cleavage reaction Methods 0.000 description 2
• HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 2
• 201000010099 disease Diseases 0.000 description 2
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 2
• 229950003499 fibrin Drugs 0.000 description 2
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
• 230000014509 gene expression Effects 0.000 description 2
• 125000004415 heterocyclylalkyl group Chemical group 0.000 description 2
• 229930195733 hydrocarbon Natural products 0.000 description 2
• XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
• 238000000338 in vitro Methods 0.000 description 2
• 150000002576 ketones Chemical class 0.000 description 2
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
• 229940127215 low-molecular weight heparin Drugs 0.000 description 2
• 229910052751 metal Inorganic materials 0.000 description 2
• 239000002184 metal Substances 0.000 description 2
• GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
• 231100000252 nontoxic Toxicity 0.000 description 2
• 230000003000 nontoxic effect Effects 0.000 description 2
• 230000002093 peripheral effect Effects 0.000 description 2
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 2
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 229940039716 prothrombin Drugs 0.000 description 2
• 238000000746 purification Methods 0.000 description 2
• 208000037803 restenosis Diseases 0.000 description 2
• 230000007017 scission Effects 0.000 description 2
• 238000003786 synthesis reaction Methods 0.000 description 2
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
• 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 2
• WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
• 230000002792 vascular Effects 0.000 description 2
• 210000005166 vasculature Anatomy 0.000 description 2
• AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 1
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 1
• 125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
• 125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
• JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 description 1
• FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 description 1
• 125000005940 1,4-dioxanyl group Chemical group 0.000 description 1
• HKDFRDIIELOLTJ-UHFFFAOYSA-N 1,4-dithianyl Chemical group [CH]1CSCCS1 HKDFRDIIELOLTJ-UHFFFAOYSA-N 0.000 description 1
• 125000001088 1-naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
• QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical compound C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 description 1
• UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 description 1
• WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical class OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 1
• WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 description 1
• 125000001216 2-naphthoyl group Chemical group C1=C(C=CC2=CC=CC=C12)C(=O)* 0.000 description 1
• 125000001698 2H-pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
• 125000004364 3-pyrrolinyl group Chemical group [H]C1=C([H])C([H])([H])N(*)C1([H])[H] 0.000 description 1
• SNOKMSHVQIKGPW-UHFFFAOYSA-N 5,6,7,8-tetrahydro-[1,3]thiazolo[4,5-c]azepin-4-one Chemical compound O=C1NCCCC2=C1N=CS2 SNOKMSHVQIKGPW-UHFFFAOYSA-N 0.000 description 1
• RENBIQXXBKOXQC-UHFFFAOYSA-N 5,6-dihydro-4h-1,3-benzothiazol-7-one Chemical compound O=C1CCCC2=C1SC=N2 RENBIQXXBKOXQC-UHFFFAOYSA-N 0.000 description 1
• NOSRZDRYWDNUOH-UHFFFAOYSA-N 5,7-dihydro-4h-[1,3]thiazolo[5,4-c]pyridin-6-one Chemical group C1NC(=O)CC2=C1SC=N2 NOSRZDRYWDNUOH-UHFFFAOYSA-N 0.000 description 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
• 208000024827 Alzheimer disease Diseases 0.000 description 1
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
• 206010002388 Angina unstable Diseases 0.000 description 1
• 108090000935 Antithrombin III Proteins 0.000 description 1
• 102100022977 Antithrombin-III Human genes 0.000 description 1
• 239000004475 Arginine Substances 0.000 description 1
• 201000001320 Atherosclerosis Diseases 0.000 description 1
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
• 208000017667 Chronic Disease Diseases 0.000 description 1
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
• 206010053567 Coagulopathies Diseases 0.000 description 1
• AAWZDTNXLSGCEK-UHFFFAOYSA-N Cordycepinsaeure Natural products OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-UHFFFAOYSA-N 0.000 description 1
• 229940123900 Direct thrombin inhibitor Drugs 0.000 description 1
• 208000005189 Embolism Diseases 0.000 description 1
• JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
• 108010071289 Factor XIII Proteins 0.000 description 1
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
• 206010022562 Intermittent claudication Diseases 0.000 description 1
• AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 1
• ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
• KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
• JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
• 239000004472 Lysine Substances 0.000 description 1
• OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
• 241001465754 Metazoa Species 0.000 description 1
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
• MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
• 229910002651 NO3 Inorganic materials 0.000 description 1
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
• AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 1
• UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 1
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
• 229910019142 PO4 Inorganic materials 0.000 description 1
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
• 208000010378 Pulmonary Embolism Diseases 0.000 description 1
• AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-N 0.000 description 1
• 206010040070 Septic Shock Diseases 0.000 description 1
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
• 208000006011 Stroke Diseases 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
• 102000003790 Thrombin receptors Human genes 0.000 description 1
• 108090000166 Thrombin receptors Proteins 0.000 description 1
• 208000001435 Thromboembolism Diseases 0.000 description 1
• 208000032109 Transient ischaemic attack Diseases 0.000 description 1
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
• 208000007814 Unstable Angina Diseases 0.000 description 1
• 208000024248 Vascular System injury Diseases 0.000 description 1
• 208000012339 Vascular injury Diseases 0.000 description 1
• 206010047249 Venous thrombosis Diseases 0.000 description 1
• 208000036142 Viral infection Diseases 0.000 description 1
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
• 230000003187 abdominal effect Effects 0.000 description 1
• 235000011054 acetic acid Nutrition 0.000 description 1
• 125000002339 acetoacetyl group Chemical group O=C([*])C([H])([H])C(=O)C([H])([H])[H] 0.000 description 1
• 230000002378 acidificating effect Effects 0.000 description 1
• 230000009471 action Effects 0.000 description 1
• 230000001154 acute effect Effects 0.000 description 1
• 125000004423 acyloxy group Chemical group 0.000 description 1
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• 208000026935 allergic disease Diseases 0.000 description 1
• WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 150000001408 amides Chemical class 0.000 description 1
• 150000001409 amidines Chemical class 0.000 description 1
• 125000005122 aminoalkylamino group Chemical group 0.000 description 1
• 229910021529 ammonia Inorganic materials 0.000 description 1
• 235000011114 ammonium hydroxide Nutrition 0.000 description 1
• 230000033115 angiogenesis Effects 0.000 description 1
• 239000005557 antagonist Substances 0.000 description 1
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
• 229960003121 arginine Drugs 0.000 description 1
• 210000005249 arterial vasculature Anatomy 0.000 description 1
• 206010003246 arthritis Diseases 0.000 description 1
• 125000005018 aryl alkenyl group Chemical group 0.000 description 1
• 125000001691 aryl alkyl amino group Chemical group 0.000 description 1
• 238000003556 assay Methods 0.000 description 1
• 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 description 1
• ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
• 230000008901 benefit Effects 0.000 description 1
• UPABQMWFWCMOFV-UHFFFAOYSA-N benethamine Chemical compound C=1C=CC=CC=1CNCCC1=CC=CC=C1 UPABQMWFWCMOFV-UHFFFAOYSA-N 0.000 description 1
• JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
• 229940077388 benzenesulfonate Drugs 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
• 229940092714 benzenesulfonic acid Drugs 0.000 description 1
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
• 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
• PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 description 1
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
• 239000008280 blood Substances 0.000 description 1
• 210000004369 blood Anatomy 0.000 description 1
• 208000015294 blood coagulation disease Diseases 0.000 description 1
• 239000006227 byproduct Substances 0.000 description 1
• 239000011575 calcium Substances 0.000 description 1
• 229910052791 calcium Inorganic materials 0.000 description 1
• AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
• 239000000920 calcium hydroxide Substances 0.000 description 1
• 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
• CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical group C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
• 125000002843 carboxylic acid group Chemical group 0.000 description 1
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
• 239000000969 carrier Substances 0.000 description 1
• 230000003915 cell function Effects 0.000 description 1
• 230000004663 cell proliferation Effects 0.000 description 1
• 230000002490 cerebral effect Effects 0.000 description 1
• 150000005829 chemical entities Chemical class 0.000 description 1
• 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
• VDANGULDQQJODZ-UHFFFAOYSA-N chloroprocaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1Cl VDANGULDQQJODZ-UHFFFAOYSA-N 0.000 description 1
• 229960002023 chloroprocaine Drugs 0.000 description 1
• OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
• 229960001231 choline Drugs 0.000 description 1
• 238000004587 chromatography analysis Methods 0.000 description 1
• 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
• 235000015165 citric acid Nutrition 0.000 description 1
• 229940105784 coagulation factor xiii Drugs 0.000 description 1
• 238000007887 coronary angioplasty Methods 0.000 description 1
• 239000013078 crystal Substances 0.000 description 1
• 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
• 125000004855 decalinyl group Chemical group C1(CCCC2CCCCC12)* 0.000 description 1
• 125000003493 decenyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
• 229940043237 diethanolamine Drugs 0.000 description 1
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
• 238000009510 drug design Methods 0.000 description 1
• 230000009977 dual effect Effects 0.000 description 1
• 238000001952 enzyme assay Methods 0.000 description 1
• 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
• 150000002170 ethers Chemical class 0.000 description 1
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 239000002360 explosive Substances 0.000 description 1
• 230000006624 extrinsic pathway Effects 0.000 description 1
• 125000003838 furazanyl group Chemical group 0.000 description 1
• 125000002541 furyl group Chemical group 0.000 description 1
• BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
• 238000001631 haemodialysis Methods 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 230000000322 hemodialysis Effects 0.000 description 1
• 125000004447 heteroarylalkenyl group Chemical group 0.000 description 1
• 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
• 125000005842 heteroatom Chemical group 0.000 description 1
• 150000004677 hydrates Chemical class 0.000 description 1
• IHOBXAWVAMAQKV-UHFFFAOYSA-N hydrazinylideneurea Chemical compound NN=NC(N)=O IHOBXAWVAMAQKV-UHFFFAOYSA-N 0.000 description 1
• 150000004678 hydrides Chemical class 0.000 description 1
• 230000007062 hydrolysis Effects 0.000 description 1
• 238000006460 hydrolysis reaction Methods 0.000 description 1
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
• 125000005946 imidazo[1,2-a]pyridyl group Chemical group 0.000 description 1
• 125000002636 imidazolinyl group Chemical group 0.000 description 1
• 125000002883 imidazolyl group Chemical group 0.000 description 1
• 238000001727 in vivo Methods 0.000 description 1
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
• 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
• 229910052500 inorganic mineral Inorganic materials 0.000 description 1
• 201000004332 intermediate coronary syndrome Diseases 0.000 description 1
• 239000013067 intermediate product Substances 0.000 description 1
• 208000021156 intermittent vascular claudication Diseases 0.000 description 1
• 230000006623 intrinsic pathway Effects 0.000 description 1
• 125000002346 iodo group Chemical group I* 0.000 description 1
• 238000005342 ion exchange Methods 0.000 description 1
• 230000007794 irritation Effects 0.000 description 1
• SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical class OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
• 238000002955 isolation Methods 0.000 description 1
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
• 125000001786 isothiazolyl group Chemical group 0.000 description 1
• 210000003127 knee Anatomy 0.000 description 1
• 239000004310 lactic acid Substances 0.000 description 1
• 235000014655 lactic acid Nutrition 0.000 description 1
• 230000007774 longterm Effects 0.000 description 1
• 210000003141 lower extremity Anatomy 0.000 description 1
• 229960003646 lysine Drugs 0.000 description 1
• VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
• 239000000347 magnesium hydroxide Substances 0.000 description 1
• 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
• 238000012423 maintenance Methods 0.000 description 1
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• 230000002503 metabolic effect Effects 0.000 description 1
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
• 239000011707 mineral Substances 0.000 description 1
• 235000010755 mineral Nutrition 0.000 description 1
• 230000002297 mitogenic effect Effects 0.000 description 1
• 230000004048 modification Effects 0.000 description 1
• 238000012986 modification Methods 0.000 description 1
• 125000002950 monocyclic group Chemical group 0.000 description 1
• 125000002757 morpholinyl group Chemical group 0.000 description 1
• LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
• RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000001624 naphthyl group Chemical group 0.000 description 1
• 125000005029 naphthylthio group Chemical group C1(=CC=CC2=CC=CC=C12)S* 0.000 description 1
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
• 208000015122 neurodegenerative disease Diseases 0.000 description 1
• 150000002825 nitriles Chemical class 0.000 description 1
• 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
• 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
• 210000004789 organ system Anatomy 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 229960003104 ornithine Drugs 0.000 description 1
• 125000001715 oxadiazolyl group Chemical group 0.000 description 1
• 125000002971 oxazolyl group Chemical group 0.000 description 1
• 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 230000001575 pathological effect Effects 0.000 description 1
• 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
• 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
• BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 1
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
• 239000010452 phosphate Substances 0.000 description 1
• 150000003904 phospholipids Chemical class 0.000 description 1
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
• 230000035790 physiological processes and functions Effects 0.000 description 1
• 125000004193 piperazinyl group Chemical group 0.000 description 1
• 125000005936 piperidyl group Chemical group 0.000 description 1
• 230000031915 positive regulation of coagulation Effects 0.000 description 1
• 230000002265 prevention Effects 0.000 description 1
• MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
• 229960004919 procaine Drugs 0.000 description 1
• 230000035755 proliferation Effects 0.000 description 1
• 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
• 238000011321 prophylaxis Methods 0.000 description 1
• 108010014806 prothrombinase complex Proteins 0.000 description 1
• 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
• 125000003373 pyrazinyl group Chemical group 0.000 description 1
• 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
• 125000003226 pyrazolyl group Chemical group 0.000 description 1
• 125000002098 pyridazinyl group Chemical group 0.000 description 1
• TXQWFIVRZNOPCK-UHFFFAOYSA-N pyridin-4-ylmethanamine Chemical compound NCC1=CC=NC=C1 TXQWFIVRZNOPCK-UHFFFAOYSA-N 0.000 description 1
• 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
• 125000000714 pyrimidinyl group Chemical group 0.000 description 1
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
• 125000006085 pyrrolopyridyl group Chemical group 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
• ZHNFLHYOFXQIOW-LPYZJUEESA-N quinine sulfate dihydrate Chemical compound [H+].[H+].O.O.[O-]S([O-])(=O)=O.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 ZHNFLHYOFXQIOW-LPYZJUEESA-N 0.000 description 1
• 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 description 1
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
• 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
• 229960001860 salicylate Drugs 0.000 description 1
• 230000036303 septic shock Effects 0.000 description 1
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
• 235000017557 sodium bicarbonate Nutrition 0.000 description 1
• 239000012312 sodium hydride Substances 0.000 description 1
• 229910000104 sodium hydride Inorganic materials 0.000 description 1
• 239000007787 solid Substances 0.000 description 1
• 239000007858 starting material Substances 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
• IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
• 238000001356 surgical procedure Methods 0.000 description 1
• 230000009885 systemic effect Effects 0.000 description 1
• 239000011975 tartaric acid Substances 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• XBXCNNQPRYLIDE-UHFFFAOYSA-N tert-butylcarbamic acid Chemical compound CC(C)(C)NC(O)=O XBXCNNQPRYLIDE-UHFFFAOYSA-N 0.000 description 1
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
• 230000001225 therapeutic effect Effects 0.000 description 1
• 125000001113 thiadiazolyl group Chemical group 0.000 description 1
• 125000001984 thiazolidinyl group Chemical group 0.000 description 1
• 125000000335 thiazolyl group Chemical group 0.000 description 1
• 125000004588 thienopyridyl group Chemical group S1C(=CC2=C1C=CC=N2)* 0.000 description 1
• 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
• 150000003573 thiols Chemical class 0.000 description 1
• 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
• 239000003868 thrombin inhibitor Substances 0.000 description 1
• 230000002537 thrombolytic effect Effects 0.000 description 1
• 230000001988 toxicity Effects 0.000 description 1
• 231100000419 toxicity Toxicity 0.000 description 1
• 230000009466 transformation Effects 0.000 description 1
• 201000010875 transient cerebral ischemia Diseases 0.000 description 1
• 125000004306 triazinyl group Chemical group 0.000 description 1
• 125000001425 triazolyl group Chemical group 0.000 description 1
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
• 210000005167 vascular cell Anatomy 0.000 description 1
• 208000019553 vascular disease Diseases 0.000 description 1
• 210000003462 vein Anatomy 0.000 description 1
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
• 230000009385 viral infection Effects 0.000 description 1
• 229910052725 zinc Inorganic materials 0.000 description 1
• 239000011701 zinc Substances 0.000 description 1