SK9432000A3 - Ortho-anthranilamide derivatives as anti-coagulants, pharmaceutical composition containing such derivatives and use thereof - Google Patents
Ortho-anthranilamide derivatives as anti-coagulants, pharmaceutical composition containing such derivatives and use thereof Download PDFInfo
- Publication number
- SK9432000A3 SK9432000A3 SK943-2000A SK9432000A SK9432000A3 SK 9432000 A3 SK9432000 A3 SK 9432000A3 SK 9432000 A SK9432000 A SK 9432000A SK 9432000 A3 SK9432000 A3 SK 9432000A3
- Authority
- SK
- Slovakia
- Prior art keywords
- group
- amino
- methyl
- alkyl
- carbonyl
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 7
- 239000003146 anticoagulant agent Substances 0.000 title abstract description 12
- 229940127219 anticoagulant drug Drugs 0.000 title abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 198
- 125000000217 alkyl group Chemical group 0.000 claims description 767
- -1 alkyl urea Chemical group 0.000 claims description 714
- 125000003118 aryl group Chemical group 0.000 claims description 557
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 521
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 409
- 125000001188 haloalkyl group Chemical group 0.000 claims description 329
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 307
- 125000001424 substituent group Chemical group 0.000 claims description 296
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 291
- 229910052736 halogen Inorganic materials 0.000 claims description 281
- 150000002367 halogens Chemical class 0.000 claims description 279
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 257
- 125000000623 heterocyclic group Chemical group 0.000 claims description 195
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 180
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 178
- 229910052739 hydrogen Inorganic materials 0.000 claims description 155
- 239000001257 hydrogen Substances 0.000 claims description 151
- 229910052757 nitrogen Inorganic materials 0.000 claims description 146
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 134
- 150000002431 hydrogen Chemical group 0.000 claims description 122
- 125000004043 oxo group Chemical group O=* 0.000 claims description 122
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 114
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 109
- 125000002947 alkylene group Chemical group 0.000 claims description 104
- 125000005843 halogen group Chemical group 0.000 claims description 76
- 125000001118 alkylidene group Chemical group 0.000 claims description 75
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 74
- 125000005842 heteroatom Chemical group 0.000 claims description 73
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 43
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 37
- 150000003254 radicals Chemical group 0.000 claims description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 26
- 229910052760 oxygen Inorganic materials 0.000 claims description 26
- 229910052717 sulfur Inorganic materials 0.000 claims description 24
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 22
- 239000001301 oxygen Substances 0.000 claims description 22
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 21
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 21
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 21
- 201000010099 disease Diseases 0.000 claims description 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
- 239000011593 sulfur Substances 0.000 claims description 19
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 13
- 150000001370 alpha-amino acid derivatives Chemical group 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 11
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 10
- 230000001732 thrombotic effect Effects 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
- FZOOOJPISNODNI-UHFFFAOYSA-N 5-chloro-2-methoxybenzamide Chemical compound COC1=CC=C(Cl)C=C1C(N)=O FZOOOJPISNODNI-UHFFFAOYSA-N 0.000 claims description 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 8
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 8
- 125000004193 piperazinyl group Chemical group 0.000 claims description 7
- 238000011282 treatment Methods 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 2
- DDSJSUBMFOEPDZ-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-(3-imidazol-1-ylpropoxy)phenyl]-4-[(4-methylpiperazin-1-yl)methyl]thiophene-2-carboxamide Chemical compound C1CN(C)CCN1CC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2OCCCN2C=NC=C2)C(=O)NC=2N=CC(Cl)=CC=2)=C1Cl DDSJSUBMFOEPDZ-UHFFFAOYSA-N 0.000 claims description 2
- BPBWVXNCSHGNGR-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-(3-pyrrolidin-1-ylpropoxy)phenyl]-4-[(4-methylpiperazin-1-yl)methyl]thiophene-2-carboxamide Chemical compound C1CN(C)CCN1CC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2OCCCN2CCCC2)C(=O)NC=2N=CC(Cl)=CC=2)=C1Cl BPBWVXNCSHGNGR-UHFFFAOYSA-N 0.000 claims description 2
- RZJNVPUXFGNUPN-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-(4,5-dihydro-1h-imidazol-2-yl)thiophene-2-carboxamide Chemical compound S1C=C(C=2NCCN=2)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 RZJNVPUXFGNUPN-UHFFFAOYSA-N 0.000 claims description 2
- FXKRFLCMQGCELQ-UHFFFAOYSA-N 4-[(3-amino-1,2,4-triazol-1-yl)methyl]-3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]thiophene-2-carboxamide Chemical compound S1C=C(CN2N=C(N)N=C2)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 FXKRFLCMQGCELQ-UHFFFAOYSA-N 0.000 claims description 2
- IUHRYFYWBZOHPA-UHFFFAOYSA-N 4-[(6-aminopurin-9-yl)methyl]-3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]thiophene-2-carboxamide Chemical compound S1C=C(CN2C3=NC=NC(N)=C3N=C2)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 IUHRYFYWBZOHPA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 229910052794 bromium Chemical group 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 60
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 44
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 6
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 4
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- MJTGQALMWUUPQM-UHFFFAOYSA-N m-Chlorobenzamide Chemical compound NC(=O)C1=CC=CC(Cl)=C1 MJTGQALMWUUPQM-UHFFFAOYSA-N 0.000 claims 3
- ABADUMLIAZCWJD-UHFFFAOYSA-N 1,3-dioxole Chemical group C1OC=CO1 ABADUMLIAZCWJD-UHFFFAOYSA-N 0.000 claims 2
- XTAYMSPPIWVWLO-UHFFFAOYSA-N 5-chloro-2-[2-(2-methoxyethoxy)ethoxy]benzamide Chemical compound COCCOCCOC1=CC=C(Cl)C=C1C(N)=O XTAYMSPPIWVWLO-UHFFFAOYSA-N 0.000 claims 2
- VPOJOSXTTMJEJZ-UHFFFAOYSA-N 1,3-benzodioxol-2-amine Chemical compound C1=CC=C2OC(N)OC2=C1 VPOJOSXTTMJEJZ-UHFFFAOYSA-N 0.000 claims 1
- BPWMQMFSPXHISM-UHFFFAOYSA-N 2-[4-[[4-chloro-5-[[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]carbamoyl]thiophen-2-yl]methyl]piperazin-1-yl]acetic acid Chemical compound C1CN(CC(=O)O)CCN1CC1=CC(Cl)=C(C(=O)NC=2C(=CC(Cl)=CC=2)C(=O)NC=2C=CC(Cl)=CC=2)S1 BPWMQMFSPXHISM-UHFFFAOYSA-N 0.000 claims 1
- LXPIICRZGBDBSS-UHFFFAOYSA-N 2-[[4-chloro-5-[[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]carbamoyl]thiophen-2-yl]methylsulfanyl]acetic acid Chemical compound S1C(CSCC(=O)O)=CC(Cl)=C1C(=O)NC1=CC=C(Cl)C=C1C(=O)NC1=CC=C(Cl)C=C1 LXPIICRZGBDBSS-UHFFFAOYSA-N 0.000 claims 1
- RBGDLYUEXLWQBZ-UHFFFAOYSA-N 2-chlorobenzamide Chemical compound NC(=O)C1=CC=CC=C1Cl RBGDLYUEXLWQBZ-UHFFFAOYSA-N 0.000 claims 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- LHWBFVWBNDBUBB-UHFFFAOYSA-N 3-chloro-5-morpholin-4-ylbenzamide Chemical compound N1(CCOCC1)C=1C=C(C(=O)N)C=C(C=1)Cl LHWBFVWBNDBUBB-UHFFFAOYSA-N 0.000 claims 1
- HNVSFRSARKQWRW-NWDGAFQWSA-N 3-chloro-N-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-[[(4S,5R)-2-imino-4,5-dimethyl-1,3-oxazolidin-3-yl]methyl]thiophene-2-carboxamide Chemical compound S1C=C(CN2C(O[C@H](C)[C@@H]2C)=N)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 HNVSFRSARKQWRW-NWDGAFQWSA-N 0.000 claims 1
- HNVSFRSARKQWRW-RYUDHWBXSA-N 3-chloro-N-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-[[(4S,5S)-2-imino-4,5-dimethyl-1,3-oxazolidin-3-yl]methyl]thiophene-2-carboxamide Chemical compound S1C=C(CN2C(O[C@@H](C)[C@@H]2C)=N)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 HNVSFRSARKQWRW-RYUDHWBXSA-N 0.000 claims 1
- RHDIMWMLDGRSMX-UHFFFAOYSA-N 3-chloro-n-[2-[(3-fluorophenyl)carbamoyl]-4-methylphenyl]-1-benzothiophene-2-carboxamide Chemical compound C=1C(C)=CC=C(NC(=O)C2=C(C3=CC=CC=C3S2)Cl)C=1C(=O)NC1=CC=CC(F)=C1 RHDIMWMLDGRSMX-UHFFFAOYSA-N 0.000 claims 1
- WJZOAIRYGLYLJP-UHFFFAOYSA-N 3-chloro-n-[2-[(4-chloro-2-methylphenyl)carbamoyl]-4-methylphenyl]-1-benzothiophene-2-carboxamide Chemical compound C=1C(C)=CC=C(NC(=O)C2=C(C3=CC=CC=C3S2)Cl)C=1C(=O)NC1=CC=C(Cl)C=C1C WJZOAIRYGLYLJP-UHFFFAOYSA-N 0.000 claims 1
- QEKZGRIPYCITHC-UHFFFAOYSA-N 3-chloro-n-[2-[(4-chlorophenyl)carbamoyl]-3-fluorophenyl]-1-benzothiophene-2-carboxamide Chemical compound FC1=CC=CC(NC(=O)C2=C(C3=CC=CC=C3S2)Cl)=C1C(=O)NC1=CC=C(Cl)C=C1 QEKZGRIPYCITHC-UHFFFAOYSA-N 0.000 claims 1
- YVICOJTWTZMVCV-UHFFFAOYSA-N 3-chloro-n-[2-[(4-chlorophenyl)carbamoyl]-4,5-dihydroxyphenyl]-1-benzothiophene-2-carboxamide Chemical compound C1=C(O)C(O)=CC(NC(=O)C2=C(C3=CC=CC=C3S2)Cl)=C1C(=O)NC1=CC=C(Cl)C=C1 YVICOJTWTZMVCV-UHFFFAOYSA-N 0.000 claims 1
- XRUABYJBVNFCML-UHFFFAOYSA-N 3-chloro-n-[2-[(4-chlorophenyl)carbamoyl]-4,5-dimethoxyphenyl]-1-benzothiophene-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC(NC(=O)C2=C(C3=CC=CC=C3S2)Cl)=C1C(=O)NC1=CC=C(Cl)C=C1 XRUABYJBVNFCML-UHFFFAOYSA-N 0.000 claims 1
- BBCHNPKKZJVJFI-UHFFFAOYSA-N 3-chloro-n-[2-[(4-chlorophenyl)carbamoyl]-4-fluoro-5-(4-methylpiperazin-1-yl)phenyl]-1-benzothiophene-2-carboxamide Chemical compound C1CN(C)CCN1C1=CC(NC(=O)C2=C(C3=CC=CC=C3S2)Cl)=C(C(=O)NC=2C=CC(Cl)=CC=2)C=C1F BBCHNPKKZJVJFI-UHFFFAOYSA-N 0.000 claims 1
- VXOSGCURSLNIDT-UHFFFAOYSA-N 3-chloro-n-[2-[(4-chlorophenyl)carbamoyl]-4-fluoro-5-[3-(4-methylpiperazin-1-yl)propylamino]phenyl]-1-benzothiophene-2-carboxamide Chemical compound C1CN(C)CCN1CCCNC1=CC(NC(=O)C2=C(C3=CC=CC=C3S2)Cl)=C(C(=O)NC=2C=CC(Cl)=CC=2)C=C1F VXOSGCURSLNIDT-UHFFFAOYSA-N 0.000 claims 1
- FPBPCDLZUPUNFJ-UHFFFAOYSA-N 3-chloro-n-[2-[(4-chlorophenyl)carbamoyl]-4-fluorophenyl]-1-benzothiophene-2-carboxamide Chemical compound C=1C(F)=CC=C(NC(=O)C2=C(C3=CC=CC=C3S2)Cl)C=1C(=O)NC1=CC=C(Cl)C=C1 FPBPCDLZUPUNFJ-UHFFFAOYSA-N 0.000 claims 1
- PXKWLECLRRYJQQ-UHFFFAOYSA-N 3-chloro-n-[2-[(4-chlorophenyl)carbamoyl]-4-fluorophenyl]-4-[(4-methylpiperazin-1-yl)methyl]thiophene-2-carboxamide Chemical compound C1CN(C)CCN1CC1=CSC(C(=O)NC=2C(=CC(F)=CC=2)C(=O)NC=2C=CC(Cl)=CC=2)=C1Cl PXKWLECLRRYJQQ-UHFFFAOYSA-N 0.000 claims 1
- ZICRHOIDBXHVQZ-UHFFFAOYSA-N 3-chloro-n-[2-[(4-chlorophenyl)carbamoyl]-4-hydroxyphenyl]-1-benzothiophene-2-carboxamide Chemical compound C=1C(O)=CC=C(NC(=O)C2=C(C3=CC=CC=C3S2)Cl)C=1C(=O)NC1=CC=C(Cl)C=C1 ZICRHOIDBXHVQZ-UHFFFAOYSA-N 0.000 claims 1
- RAADHZPXZGIAJF-UHFFFAOYSA-N 3-chloro-n-[2-[(4-chlorophenyl)carbamoyl]-5-fluorophenyl]-1-benzothiophene-2-carboxamide Chemical compound S1C2=CC=CC=C2C(Cl)=C1C(=O)NC1=CC(F)=CC=C1C(=O)NC1=CC=C(Cl)C=C1 RAADHZPXZGIAJF-UHFFFAOYSA-N 0.000 claims 1
- USYDFLLVKNQQSI-UHFFFAOYSA-N 3-chloro-n-[2-[(4-chlorophenyl)carbamoyl]-5-methylphenyl]-1-benzothiophene-2-carboxamide Chemical compound S1C2=CC=CC=C2C(Cl)=C1C(=O)NC1=CC(C)=CC=C1C(=O)NC1=CC=C(Cl)C=C1 USYDFLLVKNQQSI-UHFFFAOYSA-N 0.000 claims 1
- VCGZVERQHWNQSW-UHFFFAOYSA-N 3-chloro-n-[2-[(4-chlorophenyl)carbamoyl]-6-methylphenyl]-1-benzothiophene-2-carboxamide Chemical compound S1C2=CC=CC=C2C(Cl)=C1C(=O)NC=1C(C)=CC=CC=1C(=O)NC1=CC=C(Cl)C=C1 VCGZVERQHWNQSW-UHFFFAOYSA-N 0.000 claims 1
- KSRYPECOBMELJB-UHFFFAOYSA-N 3-chloro-n-[2-[(4-methoxyphenyl)carbamoyl]-4-methylphenyl]-1-benzothiophene-2-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C1=CC(C)=CC=C1NC(=O)C1=C(Cl)C2=CC=CC=C2S1 KSRYPECOBMELJB-UHFFFAOYSA-N 0.000 claims 1
- UEDUPTHBCYCYHE-UHFFFAOYSA-N 3-chloro-n-[2-chloro-6-[(4-chlorophenyl)carbamoyl]phenyl]-1-benzothiophene-2-carboxamide Chemical compound S1C2=CC=CC=C2C(Cl)=C1C(=O)NC1=C(Cl)C=CC=C1C(=O)NC1=CC=C(Cl)C=C1 UEDUPTHBCYCYHE-UHFFFAOYSA-N 0.000 claims 1
- AAXPXARXTNOLHQ-UHFFFAOYSA-N 3-chloro-n-[2-hydroxy-6-(phenylcarbamoyl)phenyl]-1-benzothiophene-2-carboxamide Chemical compound S1C2=CC=CC=C2C(Cl)=C1C(=O)NC=1C(O)=CC=CC=1C(=O)NC1=CC=CC=C1 AAXPXARXTNOLHQ-UHFFFAOYSA-N 0.000 claims 1
- KSRGOHMZOFXETJ-UHFFFAOYSA-N 3-chloro-n-[2-methoxy-6-(phenylcarbamoyl)phenyl]-1-benzothiophene-2-carboxamide Chemical compound S1C2=CC=CC=C2C(Cl)=C1C(=O)NC=1C(OC)=CC=CC=1C(=O)NC1=CC=CC=C1 KSRGOHMZOFXETJ-UHFFFAOYSA-N 0.000 claims 1
- BKGYOQKLSNOGQN-UHFFFAOYSA-N 3-chloro-n-[2-methyl-6-(phenylcarbamoyl)phenyl]-1-benzothiophene-2-carboxamide Chemical compound S1C2=CC=CC=C2C(Cl)=C1C(=O)NC=1C(C)=CC=CC=1C(=O)NC1=CC=CC=C1 BKGYOQKLSNOGQN-UHFFFAOYSA-N 0.000 claims 1
- JXLBCLPAUGTTIH-UHFFFAOYSA-N 3-chloro-n-[4,5-dihydroxy-2-(phenylcarbamoyl)phenyl]-1-benzothiophene-2-carboxamide Chemical compound C1=C(O)C(O)=CC(NC(=O)C2=C(C3=CC=CC=C3S2)Cl)=C1C(=O)NC1=CC=CC=C1 JXLBCLPAUGTTIH-UHFFFAOYSA-N 0.000 claims 1
- JBAOHBJEUKVLEB-UHFFFAOYSA-N 3-chloro-n-[4,5-dimethoxy-2-(phenylcarbamoyl)phenyl]-1-benzothiophene-2-carboxamide Chemical compound C1=C(OC)C(OC)=CC(NC(=O)C2=C(C3=CC=CC=C3S2)Cl)=C1C(=O)NC1=CC=CC=C1 JBAOHBJEUKVLEB-UHFFFAOYSA-N 0.000 claims 1
- ACOVNFKNEPDFFZ-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-(pyridin-2-ylcarbamoyl)phenyl]-4-[(4-methylpiperazin-1-yl)methyl]thiophene-2-carboxamide Chemical compound C1CN(C)CCN1CC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2)C(=O)NC=2N=CC=CC=2)=C1Cl ACOVNFKNEPDFFZ-UHFFFAOYSA-N 0.000 claims 1
- SGDDCTUYNPWDET-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]-5-fluorophenyl]-1-benzothiophene-2-carboxamide Chemical compound C1=C(Cl)C(F)=CC(NC(=O)C2=C(C3=CC=CC=C3S2)Cl)=C1C(=O)NC1=CC=C(Cl)C=C1 SGDDCTUYNPWDET-UHFFFAOYSA-N 0.000 claims 1
- YHZVBOFYHUAIBQ-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]-5-methylphenyl]-1-benzothiophene-2-carboxamide Chemical compound C1=C(Cl)C(C)=CC(NC(=O)C2=C(C3=CC=CC=C3S2)Cl)=C1C(=O)NC1=CC=C(Cl)C=C1 YHZVBOFYHUAIBQ-UHFFFAOYSA-N 0.000 claims 1
- UETMFYQHQXWYTE-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]-6-(3-morpholin-4-ylpropoxy)phenyl]-4-[(4-methylpiperazin-1-yl)methyl]thiophene-2-carboxamide Chemical compound C1CN(C)CCN1CC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2OCCCN2CCOCC2)C(=O)NC=2C=CC(Cl)=CC=2)=C1Cl UETMFYQHQXWYTE-UHFFFAOYSA-N 0.000 claims 1
- YUNWONLPUONZLY-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]-6-hydroxyphenyl]-1-benzothiophene-2-carboxamide Chemical compound S1C2=CC=CC=C2C(Cl)=C1C(=O)NC=1C(O)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=C1 YUNWONLPUONZLY-UHFFFAOYSA-N 0.000 claims 1
- MPGAPGRBPRGXKP-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]-6-hydroxyphenyl]-4-[(4-methylpiperazin-1-yl)methyl]thiophene-2-carboxamide Chemical compound C1CN(C)CCN1CC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2O)C(=O)NC=2C=CC(Cl)=CC=2)=C1Cl MPGAPGRBPRGXKP-UHFFFAOYSA-N 0.000 claims 1
- GZUZWPNOXCTYDQ-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]-6-methoxyphenyl]-1-benzothiophene-2-carboxamide Chemical compound S1C2=CC=CC=C2C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=C1 GZUZWPNOXCTYDQ-UHFFFAOYSA-N 0.000 claims 1
- RUQJICHXWIZZNA-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]-6-methylphenyl]-1-benzothiophene-2-carboxamide Chemical compound S1C2=CC=CC=C2C(Cl)=C1C(=O)NC=1C(C)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=C1 RUQJICHXWIZZNA-UHFFFAOYSA-N 0.000 claims 1
- BPVWZPRUIFGZGN-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-1-benzothiophene-2-carboxamide Chemical compound S1C2=CC=CC=C2C(Cl)=C1C(=O)NC1=CC=C(Cl)C=C1C(=O)NC1=CC=C(Cl)C=C1 BPVWZPRUIFGZGN-UHFFFAOYSA-N 0.000 claims 1
- GAIANRODMUVKOQ-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-4-(2-methoxyethoxymethyl)thiophene-2-carboxamide Chemical compound COCCOCC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2)C(=O)NC=2C=CC(Cl)=CC=2)=C1Cl GAIANRODMUVKOQ-UHFFFAOYSA-N 0.000 claims 1
- URIZEPZRDZSTNX-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-4-(imidazol-1-ylmethyl)thiophene-2-carboxamide Chemical compound C=1SC(C(=O)NC=2C(=CC(Cl)=CC=2)C(=O)NC=2C=CC(Cl)=CC=2)=C(Cl)C=1CN1C=CN=C1 URIZEPZRDZSTNX-UHFFFAOYSA-N 0.000 claims 1
- HJPGTJZRQOHFSA-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-4-(methylsulfanylmethyl)thiophene-2-carboxamide Chemical compound CSCC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2)C(=O)NC=2C=CC(Cl)=CC=2)=C1Cl HJPGTJZRQOHFSA-UHFFFAOYSA-N 0.000 claims 1
- ZVZCIGHYDQHRNA-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-4-(methylsulfinylmethyl)thiophene-2-carboxamide Chemical compound CS(=O)CC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2)C(=O)NC=2C=CC(Cl)=CC=2)=C1Cl ZVZCIGHYDQHRNA-UHFFFAOYSA-N 0.000 claims 1
- XAUOSNVKTOUKQA-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-4-(tetrazol-1-ylmethyl)thiophene-2-carboxamide Chemical compound C=1SC(C(=O)NC=2C(=CC(Cl)=CC=2)C(=O)NC=2C=CC(Cl)=CC=2)=C(Cl)C=1CN1C=NN=N1 XAUOSNVKTOUKQA-UHFFFAOYSA-N 0.000 claims 1
- UJXMNNKAKLLGON-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-4-(tetrazol-2-ylmethyl)thiophene-2-carboxamide Chemical compound C=1SC(C(=O)NC=2C(=CC(Cl)=CC=2)C(=O)NC=2C=CC(Cl)=CC=2)=C(Cl)C=1CN1N=CN=N1 UJXMNNKAKLLGON-UHFFFAOYSA-N 0.000 claims 1
- SGFUHAVCRILDAM-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-4-(triazol-1-ylmethyl)thiophene-2-carboxamide Chemical compound C=1SC(C(=O)NC=2C(=CC(Cl)=CC=2)C(=O)NC=2C=CC(Cl)=CC=2)=C(Cl)C=1CN1C=CN=N1 SGFUHAVCRILDAM-UHFFFAOYSA-N 0.000 claims 1
- WKQORDONQMBRAN-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-4-(triazol-2-ylmethyl)thiophene-2-carboxamide Chemical compound C=1SC(C(=O)NC=2C(=CC(Cl)=CC=2)C(=O)NC=2C=CC(Cl)=CC=2)=C(Cl)C=1CN1N=CC=N1 WKQORDONQMBRAN-UHFFFAOYSA-N 0.000 claims 1
- FIZKTFMGWNHPMZ-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-4-[(4-methylpiperazin-1-yl)methyl]thiophene-2-carboxamide Chemical compound C1CN(C)CCN1CC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2)C(=O)NC=2C=CC(Cl)=CC=2)=C1Cl FIZKTFMGWNHPMZ-UHFFFAOYSA-N 0.000 claims 1
- OWASSQDGIGRWRL-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-4-[2-(2-methoxyethoxy)ethoxymethyl]thiophene-2-carboxamide Chemical compound COCCOCCOCC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2)C(=O)NC=2C=CC(Cl)=CC=2)=C1Cl OWASSQDGIGRWRL-UHFFFAOYSA-N 0.000 claims 1
- STGQYQZIWLRALS-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-4-[2-(dimethylamino)ethylsulfanylmethyl]thiophene-2-carboxamide Chemical compound CN(C)CCSCC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2)C(=O)NC=2C=CC(Cl)=CC=2)=C1Cl STGQYQZIWLRALS-UHFFFAOYSA-N 0.000 claims 1
- CRQJVZIPZYOKOU-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-4-[2-[2-(2-methoxyethoxy)ethoxy]ethoxymethyl]thiophene-2-carboxamide Chemical compound COCCOCCOCCOCC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2)C(=O)NC=2C=CC(Cl)=CC=2)=C1Cl CRQJVZIPZYOKOU-UHFFFAOYSA-N 0.000 claims 1
- UXFYQNNDCOYLRK-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-4-[[2-(2-hydroxyethoxy)ethylamino]methyl]thiophene-2-carboxamide Chemical compound OCCOCCNCC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2)C(=O)NC=2C=CC(Cl)=CC=2)=C1Cl UXFYQNNDCOYLRK-UHFFFAOYSA-N 0.000 claims 1
- PZLABLNNLLURLH-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-4-[[4-[2-(2-hydroxyethoxy)ethyl]piperazin-1-yl]methyl]thiophene-2-carboxamide Chemical compound C1CN(CCOCCO)CCN1CC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2)C(=O)NC=2C=CC(Cl)=CC=2)=C1Cl PZLABLNNLLURLH-UHFFFAOYSA-N 0.000 claims 1
- XNZLOUVGIOARBF-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-4-methyl-5-[(4-methylpiperazin-1-yl)methyl]thiophene-2-carboxamide Chemical compound C1CN(C)CCN1CC1=C(C)C(Cl)=C(C(=O)NC=2C(=CC(Cl)=CC=2)C(=O)NC=2C=CC(Cl)=CC=2)S1 XNZLOUVGIOARBF-UHFFFAOYSA-N 0.000 claims 1
- YXKVUHJYIPCGRM-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-4-methylthiophene-2-carboxamide Chemical compound CC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2)C(=O)NC=2C=CC(Cl)=CC=2)=C1Cl YXKVUHJYIPCGRM-UHFFFAOYSA-N 0.000 claims 1
- NYTXQSBCDGIIBX-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-5-(imidazol-1-ylmethyl)thiophene-2-carboxamide Chemical compound S1C(C(=O)NC=2C(=CC(Cl)=CC=2)C(=O)NC=2C=CC(Cl)=CC=2)=C(Cl)C=C1CN1C=CN=C1 NYTXQSBCDGIIBX-UHFFFAOYSA-N 0.000 claims 1
- MKKGHFPJDJYKHF-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-5-(methylsulfanylmethyl)thiophene-2-carboxamide Chemical compound S1C(CSC)=CC(Cl)=C1C(=O)NC1=CC=C(Cl)C=C1C(=O)NC1=CC=C(Cl)C=C1 MKKGHFPJDJYKHF-UHFFFAOYSA-N 0.000 claims 1
- VBKCNNOMBAEUKA-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-5-(methylsulfinylmethyl)thiophene-2-carboxamide Chemical compound S1C(CS(=O)C)=CC(Cl)=C1C(=O)NC1=CC=C(Cl)C=C1C(=O)NC1=CC=C(Cl)C=C1 VBKCNNOMBAEUKA-UHFFFAOYSA-N 0.000 claims 1
- SCFJJFDJLOMQEJ-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-5-(methylsulfonylmethyl)thiophene-2-carboxamide Chemical compound S1C(CS(=O)(=O)C)=CC(Cl)=C1C(=O)NC1=CC=C(Cl)C=C1C(=O)NC1=CC=C(Cl)C=C1 SCFJJFDJLOMQEJ-UHFFFAOYSA-N 0.000 claims 1
- QOHWJHLSEMXCMA-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-5-(morpholin-4-ylmethyl)thiophene-2-carboxamide Chemical compound S1C(C(=O)NC=2C(=CC(Cl)=CC=2)C(=O)NC=2C=CC(Cl)=CC=2)=C(Cl)C=C1CN1CCOCC1 QOHWJHLSEMXCMA-UHFFFAOYSA-N 0.000 claims 1
- MLNIBHWAMXYNQC-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-5-[(1-oxo-1,4-thiazinan-4-yl)methyl]thiophene-2-carboxamide Chemical compound S1C(C(=O)NC=2C(=CC(Cl)=CC=2)C(=O)NC=2C=CC(Cl)=CC=2)=C(Cl)C=C1CN1CCS(=O)CC1 MLNIBHWAMXYNQC-UHFFFAOYSA-N 0.000 claims 1
- RAJDVLCJFXQAIS-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-5-[(4-methylpiperazin-1-yl)methyl]thiophene-2-carboxamide Chemical compound C1CN(C)CCN1CC1=CC(Cl)=C(C(=O)NC=2C(=CC(Cl)=CC=2)C(=O)NC=2C=CC(Cl)=CC=2)S1 RAJDVLCJFXQAIS-UHFFFAOYSA-N 0.000 claims 1
- DWOOFUCEGKAOPV-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-5-[(dimethylamino)methyl]thiophene-2-carboxamide Chemical compound S1C(CN(C)C)=CC(Cl)=C1C(=O)NC1=CC=C(Cl)C=C1C(=O)NC1=CC=C(Cl)C=C1 DWOOFUCEGKAOPV-UHFFFAOYSA-N 0.000 claims 1
- OIDLTXHNRAIYIO-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-5-[2-(dimethylamino)ethylsulfanylmethyl]thiophene-2-carboxamide Chemical compound S1C(CSCCN(C)C)=CC(Cl)=C1C(=O)NC1=CC=C(Cl)C=C1C(=O)NC1=CC=C(Cl)C=C1 OIDLTXHNRAIYIO-UHFFFAOYSA-N 0.000 claims 1
- PTHJXJVRDNJYAK-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-5-[2-(dimethylamino)ethylsulfinylmethyl]thiophene-2-carboxamide Chemical compound S1C(CS(=O)CCN(C)C)=CC(Cl)=C1C(=O)NC1=CC=C(Cl)C=C1C(=O)NC1=CC=C(Cl)C=C1 PTHJXJVRDNJYAK-UHFFFAOYSA-N 0.000 claims 1
- ZXNJCHMXYVYVRH-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-5-[[4-[2-[2-(2-methoxyethoxy)ethoxy]acetyl]piperazin-1-yl]methyl]thiophene-2-carboxamide Chemical compound C1CN(C(=O)COCCOCCOC)CCN1CC1=CC(Cl)=C(C(=O)NC=2C(=CC(Cl)=CC=2)C(=O)NC=2C=CC(Cl)=CC=2)S1 ZXNJCHMXYVYVRH-UHFFFAOYSA-N 0.000 claims 1
- INKAAAVRNUCZBR-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-5-methyl-4-[(4-methylpiperazin-1-yl)methyl]thiophene-2-carboxamide Chemical compound C1CN(C)CCN1CC1=C(C)SC(C(=O)NC=2C(=CC(Cl)=CC=2)C(=O)NC=2C=CC(Cl)=CC=2)=C1Cl INKAAAVRNUCZBR-UHFFFAOYSA-N 0.000 claims 1
- PHYGKMMNCNPGMU-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-6-[(4-methylpiperazin-1-yl)methyl]-1-benzothiophene-2-carboxamide Chemical compound C1CN(C)CCN1CC1=CC=C(C(Cl)=C(S2)C(=O)NC=3C(=CC(Cl)=CC=3)C(=O)NC=3C=CC(Cl)=CC=3)C2=C1 PHYGKMMNCNPGMU-UHFFFAOYSA-N 0.000 claims 1
- MQKQSGLRSREOQS-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-6-[(dimethylamino)methyl]-1-benzothiophene-2-carboxamide Chemical compound S1C2=CC(CN(C)C)=CC=C2C(Cl)=C1C(=O)NC1=CC=C(Cl)C=C1C(=O)NC1=CC=C(Cl)C=C1 MQKQSGLRSREOQS-UHFFFAOYSA-N 0.000 claims 1
- YAQJDQSFMATAHT-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-6-methyl-1-benzothiophene-2-carboxamide Chemical compound S1C2=CC(C)=CC=C2C(Cl)=C1C(=O)NC1=CC=C(Cl)C=C1C(=O)NC1=CC=C(Cl)C=C1 YAQJDQSFMATAHT-UHFFFAOYSA-N 0.000 claims 1
- IUZOSIBBOMBQJJ-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-(2-ethoxyethoxy)phenyl]-4-[(4-methylpiperazin-1-yl)methyl]thiophene-2-carboxamide Chemical compound S1C=C(CN2CCN(C)CC2)C(Cl)=C1C(=O)NC=1C(OCCOCC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 IUZOSIBBOMBQJJ-UHFFFAOYSA-N 0.000 claims 1
- LNHIKHDQUFYGBN-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-(2-hydroxyethoxy)phenyl]-4-[(4-methylpiperazin-1-yl)methyl]thiophene-2-carboxamide Chemical compound C1CN(C)CCN1CC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2OCCO)C(=O)NC=2N=CC(Cl)=CC=2)=C1Cl LNHIKHDQUFYGBN-UHFFFAOYSA-N 0.000 claims 1
- DTDPIZAZFIJDPA-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-(2-methoxyethoxy)phenyl]-4-[(4-ethylpiperazin-1-yl)methyl]thiophene-2-carboxamide Chemical compound C1CN(CC)CCN1CC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2OCCOC)C(=O)NC=2N=CC(Cl)=CC=2)=C1Cl DTDPIZAZFIJDPA-UHFFFAOYSA-N 0.000 claims 1
- HNHCZXHUMQGFNR-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-(2-methoxyethoxy)phenyl]-4-[(4-methylpiperazin-1-yl)methyl]thiophene-2-carboxamide Chemical compound S1C=C(CN2CCN(C)CC2)C(Cl)=C1C(=O)NC=1C(OCCOC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 HNHCZXHUMQGFNR-UHFFFAOYSA-N 0.000 claims 1
- JJNTWTGIOJWHRS-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-(4-methylpiperazin-1-yl)phenyl]-4-[(4-methylpiperazin-1-yl)methyl]thiophene-2-carboxamide Chemical compound C1CN(C)CCN1CC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2N2CCN(C)CC2)C(=O)NC=2N=CC(Cl)=CC=2)=C1Cl JJNTWTGIOJWHRS-UHFFFAOYSA-N 0.000 claims 1
- SABBUHCRYWUVBM-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-hydroxyphenyl]-4-[(4-methylpiperazin-1-yl)methyl]thiophene-2-carboxamide Chemical compound C1CN(C)CCN1CC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2O)C(=O)NC=2N=CC(Cl)=CC=2)=C1Cl SABBUHCRYWUVBM-UHFFFAOYSA-N 0.000 claims 1
- QGHRPBPYOREXAU-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-(1h-imidazol-2-ylsulfanylmethyl)thiophene-2-carboxamide Chemical compound S1C=C(CSC=2NC=CN=2)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 QGHRPBPYOREXAU-UHFFFAOYSA-N 0.000 claims 1
- SJBCOZSJGJUCDT-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-(2-hydroxyethylsulfinylmethyl)thiophene-2-carboxamide Chemical compound S1C=C(CS(=O)CCO)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 SJBCOZSJGJUCDT-UHFFFAOYSA-N 0.000 claims 1
- KAYNNYHFHARCLZ-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-(4,5-dihydroimidazol-1-ylmethyl)thiophene-2-carboxamide Chemical compound S1C=C(CN2C=NCC2)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 KAYNNYHFHARCLZ-UHFFFAOYSA-N 0.000 claims 1
- GGGHQRNAMJVUEQ-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-(chloromethyl)thiophene-2-carboxamide Chemical compound S1C=C(CCl)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 GGGHQRNAMJVUEQ-UHFFFAOYSA-N 0.000 claims 1
- IQQLZUVKODSVFV-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-(cyanomethyl)thiophene-2-carboxamide Chemical compound S1C=C(CC#N)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 IQQLZUVKODSVFV-UHFFFAOYSA-N 0.000 claims 1
- LIHSLAWJIRIYRU-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-(diethylaminomethyl)thiophene-2-carboxamide Chemical compound CCN(CC)CC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2OC)C(=O)NC=2N=CC(Cl)=CC=2)=C1Cl LIHSLAWJIRIYRU-UHFFFAOYSA-N 0.000 claims 1
- FCTAWFJTGLMEKQ-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-(diethylaminooxymethyl)thiophene-2-carboxamide Chemical compound CCN(CC)OCC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2OC)C(=O)NC=2N=CC(Cl)=CC=2)=C1Cl FCTAWFJTGLMEKQ-UHFFFAOYSA-N 0.000 claims 1
- WHDKIKHSLJFJEZ-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-(ethylaminomethyl)thiophene-2-carboxamide Chemical compound CCNCC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2OC)C(=O)NC=2N=CC(Cl)=CC=2)=C1Cl WHDKIKHSLJFJEZ-UHFFFAOYSA-N 0.000 claims 1
- CYFNXPSIQONWKY-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-(methylaminomethyl)thiophene-2-carboxamide Chemical compound CNCC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2OC)C(=O)NC=2N=CC(Cl)=CC=2)=C1Cl CYFNXPSIQONWKY-UHFFFAOYSA-N 0.000 claims 1
- RYAHOGNRTSVXDA-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-(methylsulfinylmethyl)thiophene-2-carboxamide Chemical compound S1C=C(CS(C)=O)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 RYAHOGNRTSVXDA-UHFFFAOYSA-N 0.000 claims 1
- ZAEDZKGOISXFST-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-(morpholin-4-ylmethyl)thiophene-2-carboxamide Chemical compound S1C=C(CN2CCOCC2)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 ZAEDZKGOISXFST-UHFFFAOYSA-N 0.000 claims 1
- FQFFAJRSEYKPMP-UHFFFAOYSA-O 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-(pyridin-1-ium-1-ylmethyl)thiophene-2-carboxamide Chemical compound S1C=C(C[N+]=2C=CC=CC=2)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 FQFFAJRSEYKPMP-UHFFFAOYSA-O 0.000 claims 1
- DGAZPLXRUCDHFC-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-(pyrrolidin-1-ylmethyl)thiophene-2-carboxamide Chemical compound S1C=C(CN2CCCC2)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 DGAZPLXRUCDHFC-UHFFFAOYSA-N 0.000 claims 1
- OXGZZQMZVQOZAU-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-[(2,4-dimethylimidazol-1-yl)methyl]thiophene-2-carboxamide Chemical compound S1C=C(CN2C(=NC(C)=C2)C)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 OXGZZQMZVQOZAU-UHFFFAOYSA-N 0.000 claims 1
- OEQHPFDDMNYJKZ-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-[(2,5-dimethylimidazol-1-yl)methyl]thiophene-2-carboxamide Chemical compound S1C=C(CN2C(=NC=C2C)C)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 OEQHPFDDMNYJKZ-UHFFFAOYSA-N 0.000 claims 1
- KQNCKTQFJDZBMW-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-[(2-chloroethylcarbamoylamino)methyl]thiophene-2-carboxamide Chemical compound S1C=C(CNC(=O)NCCCl)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 KQNCKTQFJDZBMW-UHFFFAOYSA-N 0.000 claims 1
- BJFNXSFURMHCFP-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-[(2-ethyliminopyrrolidin-1-yl)methyl]thiophene-2-carboxamide Chemical compound CCN=C1CCCN1CC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2OC)C(=O)NC=2N=CC(Cl)=CC=2)=C1Cl BJFNXSFURMHCFP-UHFFFAOYSA-N 0.000 claims 1
- SXQUXBHDGPCVGV-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-[(2-hydroxyethylamino)methyl]thiophene-2-carboxamide Chemical compound S1C=C(CNCCO)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 SXQUXBHDGPCVGV-UHFFFAOYSA-N 0.000 claims 1
- KTDKEJBDMFJIOJ-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-[(2-hydroxyethylcarbamoylamino)methyl]thiophene-2-carboxamide Chemical compound S1C=C(CNC(=O)NCCO)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 KTDKEJBDMFJIOJ-UHFFFAOYSA-N 0.000 claims 1
- IAADFSFBXKPDGE-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-[(2-imino-1,3-thiazolidin-3-yl)methyl]thiophene-2-carboxamide Chemical compound S1C=C(CN2C(SCC2)=N)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 IAADFSFBXKPDGE-UHFFFAOYSA-N 0.000 claims 1
- DBXOUDFJCFLEKT-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-[(2-imino-3-methylimidazol-1-yl)methyl]thiophene-2-carboxamide Chemical compound S1C=C(CN2C(N(C)C=C2)=N)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 DBXOUDFJCFLEKT-UHFFFAOYSA-N 0.000 claims 1
- PRJDABIRCYRZFL-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-[(2-methyl-4,5-dihydroimidazol-1-yl)methyl]thiophene-2-carboxamide Chemical compound S1C=C(CN2C(=NCC2)C)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 PRJDABIRCYRZFL-UHFFFAOYSA-N 0.000 claims 1
- QPSUSLWQDBYHKB-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-[(2-methylsulfanyl-4,5-dihydroimidazol-1-yl)methyl]thiophene-2-carboxamide Chemical compound S1C=C(CN2C(=NCC2)SC)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 QPSUSLWQDBYHKB-UHFFFAOYSA-N 0.000 claims 1
- KTMRBAXNWBQLBW-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-[(2-propan-2-ylimidazol-1-yl)methyl]thiophene-2-carboxamide Chemical compound S1C=C(CN2C(=NC=C2)C(C)C)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 KTMRBAXNWBQLBW-UHFFFAOYSA-N 0.000 claims 1
- AHHAXIWPQHECGW-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-[(3,7-dimethyl-2,6-dioxo-4,5-dihydropurin-1-yl)methyl]thiophene-2-carboxamide Chemical compound S1C=C(CN2C(N(C)C3C(N(C=N3)C)C2=O)=O)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 AHHAXIWPQHECGW-UHFFFAOYSA-N 0.000 claims 1
- IDXRWMKDECSDCG-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-[(4,5-dichloroimidazol-1-yl)methyl]thiophene-2-carboxamide Chemical compound S1C=C(CN2C(=C(Cl)N=C2)Cl)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 IDXRWMKDECSDCG-UHFFFAOYSA-N 0.000 claims 1
- QSRGHCMJHAHSQY-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-[(4-formylpiperazin-1-yl)methyl]thiophene-2-carboxamide Chemical compound S1C=C(CN2CCN(CC2)C=O)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 QSRGHCMJHAHSQY-UHFFFAOYSA-N 0.000 claims 1
- DMKXBIGIHQXYRR-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-[(4-methylimidazol-1-yl)methyl]thiophene-2-carboxamide Chemical compound S1C=C(CN2C=C(C)N=C2)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 DMKXBIGIHQXYRR-UHFFFAOYSA-N 0.000 claims 1
- DBENURRVXMYTJS-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-[(4-methylpiperazin-1-yl)methyl]thiophene-2-carboxamide Chemical compound S1C=C(CN2CCN(C)CC2)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 DBENURRVXMYTJS-UHFFFAOYSA-N 0.000 claims 1
- BKSXESOHDCMIQD-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-[(5-methylimidazol-1-yl)methyl]thiophene-2-carboxamide Chemical compound S1C=C(CN2C(=CN=C2)C)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 BKSXESOHDCMIQD-UHFFFAOYSA-N 0.000 claims 1
- CDRDNYNPDFCOAV-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-[(dimethylamino)methyl]thiophene-2-carboxamide Chemical compound S1C=C(CN(C)C)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 CDRDNYNPDFCOAV-UHFFFAOYSA-N 0.000 claims 1
- RKEPARXBCXBFAS-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-[2-(methylamino)ethyl]thiophene-2-carboxamide Chemical compound CNCCC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2OC)C(=O)NC=2N=CC(Cl)=CC=2)=C1Cl RKEPARXBCXBFAS-UHFFFAOYSA-N 0.000 claims 1
- SMNBCUTUVZYNCT-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-[[2-(chloromethyl)-4,5-dihydroimidazol-1-yl]methyl]thiophene-2-carboxamide Chemical compound S1C=C(CN2C(=NCC2)CCl)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 SMNBCUTUVZYNCT-UHFFFAOYSA-N 0.000 claims 1
- YFAXLRBRHUSAEA-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-[[2-(cyanomethyl)-4,5-dihydroimidazol-1-yl]methyl]thiophene-2-carboxamide Chemical compound S1C=C(CN2C(=NCC2)CC#N)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 YFAXLRBRHUSAEA-UHFFFAOYSA-N 0.000 claims 1
- UAKJCNNTJDRWOB-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-[[2-(fluoromethyl)-4,5-dihydroimidazol-1-yl]methyl]thiophene-2-carboxamide Chemical compound S1C=C(CN2C(=NCC2)CF)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 UAKJCNNTJDRWOB-UHFFFAOYSA-N 0.000 claims 1
- LLHSZBPXQIOQJJ-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-[[2-(methylamino)imidazol-1-yl]methyl]thiophene-2-carboxamide Chemical compound CNC1=NC=CN1CC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2OC)C(=O)NC=2N=CC(Cl)=CC=2)=C1Cl LLHSZBPXQIOQJJ-UHFFFAOYSA-N 0.000 claims 1
- AJUODLBHDWUMCL-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-[[2-imino-5-(methoxymethyl)-1,3-oxazolidin-3-yl]methyl]thiophene-2-carboxamide Chemical compound N=C1OC(COC)CN1CC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2OC)C(=O)NC=2N=CC(Cl)=CC=2)=C1Cl AJUODLBHDWUMCL-UHFFFAOYSA-N 0.000 claims 1
- KFPQNOYECHZQKG-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-methylthiophene-2-carboxamide Chemical compound S1C=C(C)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 KFPQNOYECHZQKG-UHFFFAOYSA-N 0.000 claims 1
- KIHGQNNFFXYHPK-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-morpholin-4-ylphenyl]-4-[(2-imino-1,3-oxazolidin-3-yl)methyl]thiophene-2-carboxamide Chemical compound C=1SC(C(=O)NC=2C(=CC(Cl)=CC=2N2CCOCC2)C(=O)NC=2N=CC(Cl)=CC=2)=C(Cl)C=1CN1CCOC1=N KIHGQNNFFXYHPK-UHFFFAOYSA-N 0.000 claims 1
- VSYDQVQSFJVQHA-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-morpholin-4-ylphenyl]-4-[(4-ethylpiperazin-1-yl)methyl]thiophene-2-carboxamide Chemical compound C1CN(CC)CCN1CC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2N2CCOCC2)C(=O)NC=2N=CC(Cl)=CC=2)=C1Cl VSYDQVQSFJVQHA-UHFFFAOYSA-N 0.000 claims 1
- QOBOCXDRRKFNTM-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-morpholin-4-ylphenyl]-4-[(4-methylpiperazin-1-yl)methyl]thiophene-2-carboxamide Chemical compound C1CN(C)CCN1CC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2N2CCOCC2)C(=O)NC=2N=CC(Cl)=CC=2)=C1Cl QOBOCXDRRKFNTM-UHFFFAOYSA-N 0.000 claims 1
- YIQVWGQLAKEIRI-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-pyrrolidin-1-ylphenyl]-4-[(4-methylpiperazin-1-yl)methyl]thiophene-2-carboxamide Chemical compound C1CN(C)CCN1CC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2N2CCCC2)C(=O)NC=2N=CC(Cl)=CC=2)=C1Cl YIQVWGQLAKEIRI-UHFFFAOYSA-N 0.000 claims 1
- FSCCPJPJIPZLON-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]phenyl]-4-[(4-methylpiperazin-1-yl)methyl]thiophene-2-carboxamide Chemical compound C1CN(C)CCN1CC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2)C(=O)NC=2N=CC(Cl)=CC=2)=C1Cl FSCCPJPJIPZLON-UHFFFAOYSA-N 0.000 claims 1
- FYZHNHHNHSEJGK-UHFFFAOYSA-N 3-chloro-n-[4-methyl-2-(phenylcarbamoyl)phenyl]-1-benzothiophene-2-carboxamide Chemical compound C=1C(C)=CC=C(NC(=O)C2=C(C3=CC=CC=C3S2)Cl)C=1C(=O)NC1=CC=CC=C1 FYZHNHHNHSEJGK-UHFFFAOYSA-N 0.000 claims 1
- AFMKNTPNGUGADA-UHFFFAOYSA-N 3-chloro-n-[4-methyl-2-[(3-methylphenyl)carbamoyl]phenyl]-1-benzothiophene-2-carboxamide Chemical compound CC1=CC=CC(NC(=O)C=2C(=CC=C(C)C=2)NC(=O)C2=C(C3=CC=CC=C3S2)Cl)=C1 AFMKNTPNGUGADA-UHFFFAOYSA-N 0.000 claims 1
- UGENJRVKAPCWQB-UHFFFAOYSA-N 3-chloro-n-[5-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-1-benzothiophene-2-carboxamide Chemical compound S1C2=CC=CC=C2C(Cl)=C1C(=O)NC1=CC(Cl)=CC=C1C(=O)NC1=CC=C(Cl)C=C1 UGENJRVKAPCWQB-UHFFFAOYSA-N 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- ZQELKYLGCFHINW-UHFFFAOYSA-N 4-(aminomethyl)-3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]thiophene-2-carboxamide Chemical compound S1C=C(CN)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 ZQELKYLGCFHINW-UHFFFAOYSA-N 0.000 claims 1
- FKBAEEVPBYEATO-UHFFFAOYSA-N 4-[(2-aminoimidazol-1-yl)methyl]-3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]-6-methoxyphenyl]thiophene-2-carboxamide Chemical compound S1C=C(CN2C(=NC=C2)N)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=C1 FKBAEEVPBYEATO-UHFFFAOYSA-N 0.000 claims 1
- JBLTXNAFEYSKQX-UHFFFAOYSA-N 4-[(2-aminoimidazol-1-yl)methyl]-3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]thiophene-2-carboxamide Chemical compound S1C=C(CN2C(=NC=C2)N)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 JBLTXNAFEYSKQX-UHFFFAOYSA-N 0.000 claims 1
- JKSLRRCHCWOFGF-UHFFFAOYSA-N 4-[(2e)-2-amino-2-hydroxyiminoethyl]-3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]thiophene-2-carboxamide Chemical compound S1C=C(CC(N)=NO)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 JKSLRRCHCWOFGF-UHFFFAOYSA-N 0.000 claims 1
- PRXYXBVCYQVJNW-UHFFFAOYSA-N 4-[(4-acetylpiperazin-1-yl)methyl]-3-chloro-n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]thiophene-2-carboxamide Chemical compound C1CN(C(=O)C)CCN1CC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2)C(=O)NC=2C=CC(Cl)=CC=2)=C1Cl PRXYXBVCYQVJNW-UHFFFAOYSA-N 0.000 claims 1
- QZNDQPOVNWABCG-UHFFFAOYSA-N 4-[(5-aminotetrazol-1-yl)methyl]-3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]thiophene-2-carboxamide Chemical compound S1C=C(CN2C(=NN=N2)N)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 QZNDQPOVNWABCG-UHFFFAOYSA-N 0.000 claims 1
- KYNSSENFOFNJOF-XZOQPEGZSA-N 4-[[(4s,5r)-2-amino-4,5-dimethoxy-4,5-dihydroimidazol-1-yl]methyl]-3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]thiophene-2-carboxamide Chemical compound CO[C@@H]1[C@H](OC)NC(=N)N1CC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2OC)C(=O)NC=2N=CC(Cl)=CC=2)=C1Cl KYNSSENFOFNJOF-XZOQPEGZSA-N 0.000 claims 1
- LZMGJZMHFQKXLC-UHFFFAOYSA-N 4-[[2-[(2-amino-2-oxoethyl)amino]-4,5-dihydroimidazol-1-yl]methyl]-3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]thiophene-2-carboxamide Chemical compound S1C=C(CN2C(NCC2)=NCC(N)=O)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 LZMGJZMHFQKXLC-UHFFFAOYSA-N 0.000 claims 1
- HMYQDPPZFYBXFB-UHFFFAOYSA-N 4-[[carbamimidoyl(methyl)amino]methyl]-3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]thiophene-2-carboxamide Chemical compound S1C=C(CN(C)C(N)=N)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 HMYQDPPZFYBXFB-UHFFFAOYSA-N 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- RMEKUBWGWWVZMD-UHFFFAOYSA-N 5-fluoro-N',N'-dimethyl-2-(propylamino)benzohydrazide Chemical compound C(CC)NC1=C(C(=O)NN(C)C)C=C(C=C1)F RMEKUBWGWWVZMD-UHFFFAOYSA-N 0.000 claims 1
- HLFUMWOQXABKPF-UHFFFAOYSA-N S1C=C(CN2C(NCCC2)N2C(N=CC=C2)=N)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 Chemical compound S1C=C(CN2C(NCCC2)N2C(N=CC=C2)=N)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 HLFUMWOQXABKPF-UHFFFAOYSA-N 0.000 claims 1
- YWPBHXSVZYRBAM-UHFFFAOYSA-N S1C=C(N2C(=CN=C2)CO)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 Chemical compound S1C=C(N2C(=CN=C2)CO)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 YWPBHXSVZYRBAM-UHFFFAOYSA-N 0.000 claims 1
- GGNMTJKRHHLJHH-UHFFFAOYSA-N Trimethylaethergallussaeure-amid Natural products COC1=CC(C(N)=O)=CC(OC)=C1OC GGNMTJKRHHLJHH-UHFFFAOYSA-N 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- CGHHUHSORDJCPD-UHFFFAOYSA-N ethyl 2-[4-[[4-chloro-5-[[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]carbamoyl]thiophen-2-yl]methyl]piperazin-1-yl]acetate Chemical compound C1CN(CC(=O)OCC)CCN1CC1=CC(Cl)=C(C(=O)NC=2C(=CC(Cl)=CC=2)C(=O)NC=2C=CC(Cl)=CC=2)S1 CGHHUHSORDJCPD-UHFFFAOYSA-N 0.000 claims 1
- UOJJKCMWDYNZNE-UHFFFAOYSA-N methyl 2-[[4-chloro-5-[[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]carbamoyl]thiophen-3-yl]methylsulfanyl]acetate Chemical compound COC(=O)CSCC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2)C(=O)NC=2C=CC(Cl)=CC=2)=C1Cl UOJJKCMWDYNZNE-UHFFFAOYSA-N 0.000 claims 1
- VDMBXXAHBZBMFQ-UHFFFAOYSA-N n',n',2-trimethylbenzohydrazide Chemical compound CN(C)NC(=O)C1=CC=CC=C1C VDMBXXAHBZBMFQ-UHFFFAOYSA-N 0.000 claims 1
- HMHDXNVPVJOWEH-UHFFFAOYSA-N n-[2-[(4-chlorophenyl)carbamoyl]-4-methylphenyl]-3-methoxy-1-benzothiophene-2-carboxamide Chemical compound S1C2=CC=CC=C2C(OC)=C1C(=O)NC1=CC=C(C)C=C1C(=O)NC1=CC=C(Cl)C=C1 HMHDXNVPVJOWEH-UHFFFAOYSA-N 0.000 claims 1
- PDMDFSVXZWXYPY-UHFFFAOYSA-N n-[2-[(4-chlorophenyl)carbamoyl]-4-methylphenyl]-3-methoxythiophene-2-carboxamide Chemical compound C1=CSC(C(=O)NC=2C(=CC(C)=CC=2)C(=O)NC=2C=CC(Cl)=CC=2)=C1OC PDMDFSVXZWXYPY-UHFFFAOYSA-N 0.000 claims 1
- VUZQMQLOGAJZPS-UHFFFAOYSA-N n-[2-[(4-fluorophenyl)carbamoyl]-4-methylphenyl]-3-methyl-1-benzothiophene-2-carboxamide Chemical compound S1C2=CC=CC=C2C(C)=C1C(=O)NC1=CC=C(C)C=C1C(=O)NC1=CC=C(F)C=C1 VUZQMQLOGAJZPS-UHFFFAOYSA-N 0.000 claims 1
- VUBVNWNDSRYCHH-UHFFFAOYSA-N n-[2-amino-4-chloro-6-[(5-chloropyridin-2-yl)carbamoyl]phenyl]-3-chloro-4-[(4-methylpiperazin-1-yl)methyl]thiophene-2-carboxamide Chemical compound C1CN(C)CCN1CC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2N)C(=O)NC=2N=CC(Cl)=CC=2)=C1Cl VUBVNWNDSRYCHH-UHFFFAOYSA-N 0.000 claims 1
- VZCWTEHKAAGLQX-UHFFFAOYSA-N n-[4-amino-2-[(4-chlorophenyl)carbamoyl]phenyl]-3-chloro-1-benzothiophene-2-carboxamide Chemical compound C=1C(N)=CC=C(NC(=O)C2=C(C3=CC=CC=C3S2)Cl)C=1C(=O)NC1=CC=C(Cl)C=C1 VZCWTEHKAAGLQX-UHFFFAOYSA-N 0.000 claims 1
- VCMKFROKSDQHLO-UHFFFAOYSA-N n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-3-[(4-methylpiperazin-1-yl)methyl]-1-benzothiophene-2-carboxamide Chemical compound C1CN(C)CCN1CC1=C(C(=O)NC=2C(=CC(Cl)=CC=2)C(=O)NC=2C=CC(Cl)=CC=2)SC2=CC=CC=C12 VCMKFROKSDQHLO-UHFFFAOYSA-N 0.000 claims 1
- GUWHVNCCIYIYIP-UHFFFAOYSA-N n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-3-[(dimethylamino)methyl]-1-benzothiophene-2-carboxamide Chemical compound S1C2=CC=CC=C2C(CN(C)C)=C1C(=O)NC1=CC=C(Cl)C=C1C(=O)NC1=CC=C(Cl)C=C1 GUWHVNCCIYIYIP-UHFFFAOYSA-N 0.000 claims 1
- PMROMFBTYNBPHW-UHFFFAOYSA-N n-[4-chloro-2-[(4-chlorophenyl)carbamoyl]phenyl]-3-methyl-1-benzothiophene-2-carboxamide Chemical compound S1C2=CC=CC=C2C(C)=C1C(=O)NC1=CC=C(Cl)C=C1C(=O)NC1=CC=C(Cl)C=C1 PMROMFBTYNBPHW-UHFFFAOYSA-N 0.000 claims 1
- 108010074860 Factor Xa Proteins 0.000 description 26
- 108090000190 Thrombin Proteins 0.000 description 14
- 229960004072 thrombin Drugs 0.000 description 14
- 238000000034 method Methods 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 10
- 230000015271 coagulation Effects 0.000 description 10
- 238000005345 coagulation Methods 0.000 description 10
- 239000003112 inhibitor Substances 0.000 description 9
- 230000002401 inhibitory effect Effects 0.000 description 9
- 208000007536 Thrombosis Diseases 0.000 description 8
- 239000000546 pharmaceutical excipient Substances 0.000 description 8
- 229940123583 Factor Xa inhibitor Drugs 0.000 description 7
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- 108010000499 Thromboplastin Proteins 0.000 description 6
- 102000002262 Thromboplastin Human genes 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 125000005968 oxazolinyl group Chemical group 0.000 description 6
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 238000003556 assay Methods 0.000 description 5
- 230000037361 pathway Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 102100030951 Tissue factor pathway inhibitor Human genes 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 108010013555 lipoprotein-associated coagulation inhibitor Proteins 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- 238000011321 prophylaxis Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 206010051055 Deep vein thrombosis Diseases 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 102000009123 Fibrin Human genes 0.000 description 3
- 108010073385 Fibrin Proteins 0.000 description 3
- BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 description 3
- 108010049003 Fibrinogen Proteins 0.000 description 3
- 102000008946 Fibrinogen Human genes 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 108090000373 Tissue Plasminogen Activator Proteins 0.000 description 3
- 102000003978 Tissue Plasminogen Activator Human genes 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 206010047249 Venous thrombosis Diseases 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 235000001014 amino acid Nutrition 0.000 description 3
- 229940024606 amino acid Drugs 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 238000004166 bioassay Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229950003499 fibrin Drugs 0.000 description 3
- 229940012952 fibrinogen Drugs 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 239000003001 serine protease inhibitor Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 229960000187 tissue plasminogen activator Drugs 0.000 description 3
- BRECVBLBGQIGDF-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-[(2-methyl-4-nitroimidazol-1-yl)methyl]thiophene-2-carboxamide Chemical compound S1C=C(CN2C(=NC(=C2)[N+]([O-])=O)C)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 BRECVBLBGQIGDF-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- 102000004411 Antithrombin III Human genes 0.000 description 2
- 108090000935 Antithrombin III Proteins 0.000 description 2
- 239000004475 Arginine Substances 0.000 description 2
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 108010061932 Factor VIIIa Proteins 0.000 description 2
- 108010054265 Factor VIIa Proteins 0.000 description 2
- 108010074105 Factor Va Proteins 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 108090000481 Heparin Cofactor II Proteins 0.000 description 2
- 102100030500 Heparin cofactor 2 Human genes 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 2
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 2
- 101800004937 Protein C Proteins 0.000 description 2
- 102000017975 Protein C Human genes 0.000 description 2
- 108010094028 Prothrombin Proteins 0.000 description 2
- 102100027378 Prothrombin Human genes 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 101800001700 Saposin-D Proteins 0.000 description 2
- 102000012479 Serine Proteases Human genes 0.000 description 2
- 108010022999 Serine Proteases Proteins 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 102000012607 Thrombomodulin Human genes 0.000 description 2
- 108010079274 Thrombomodulin Proteins 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 235000004279 alanine Nutrition 0.000 description 2
- 235000008206 alpha-amino acids Nutrition 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 2
- 229960005348 antithrombin iii Drugs 0.000 description 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 2
- 229960003121 arginine Drugs 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 150000001556 benzimidazoles Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 229960001948 caffeine Drugs 0.000 description 2
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 2
- 229960001231 choline Drugs 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 229940088598 enzyme Drugs 0.000 description 2
- 229940012414 factor viia Drugs 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 2
- 229960002885 histidine Drugs 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 235000018977 lysine Nutrition 0.000 description 2
- 159000000003 magnesium salts Chemical class 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 229940124531 pharmaceutical excipient Drugs 0.000 description 2
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Chemical group 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 229960000856 protein c Drugs 0.000 description 2
- 229940039716 prothrombin Drugs 0.000 description 2
- 108010014806 prothrombinase complex Proteins 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 238000001356 surgical procedure Methods 0.000 description 2
- 230000002459 sustained effect Effects 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 2
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 2
- 108010065972 tick anticoagulant peptide Proteins 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 2
- FTLYMKDSHNWQKD-UHFFFAOYSA-N (2,4,5-trichlorophenyl)boronic acid Chemical compound OB(O)C1=CC(Cl)=C(Cl)C=C1Cl FTLYMKDSHNWQKD-UHFFFAOYSA-N 0.000 description 1
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- PGOHTUIFYSHAQG-LJSDBVFPSA-N (2S)-6-amino-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-1-[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-4-methylsulfanylbutanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-carbamimidamidopentanoyl]amino]propanoyl]pyrrolidine-2-carbonyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]acetyl]amino]-3-hydroxypropanoyl]amino]-4-methylpentanoyl]amino]-3-sulfanylpropanoyl]amino]-4-methylsulfanylbutanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-hydroxybutanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-hydroxypropanoyl]amino]-3-hydroxypropanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxybutanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-carbamimidamidopentanoyl]amino]-5-oxopentanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxypropanoyl]amino]-3-carboxypropanoyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]-5-oxopentanoyl]amino]-3-phenylpropanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-4-oxobutanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-4-carboxybutanoyl]amino]-5-oxopentanoyl]amino]hexanoic acid Chemical compound CSCC[C@H](N)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H](Cc1cnc[nH]1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCCN)C(O)=O PGOHTUIFYSHAQG-LJSDBVFPSA-N 0.000 description 1
- ICLYJLBTOGPLMC-KVVVOXFISA-N (z)-octadec-9-enoate;tris(2-hydroxyethyl)azanium Chemical compound OCCN(CCO)CCO.CCCCCCCC\C=C/CCCCCCCC(O)=O ICLYJLBTOGPLMC-KVVVOXFISA-N 0.000 description 1
- UKAUYVFTDYCKQA-UHFFFAOYSA-N -2-Amino-4-hydroxybutanoic acid Natural products OC(=O)C(N)CCO UKAUYVFTDYCKQA-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical group C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 1
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical group CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- 229940013085 2-diethylaminoethanol Drugs 0.000 description 1
- WRFPVMFCRNYQNR-UHFFFAOYSA-N 2-hydroxyphenylalanine Chemical compound OC(=O)C(N)CC1=CC=CC=C1O WRFPVMFCRNYQNR-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000004635 2-oxazepinyl group Chemical group O1N(CC=CC=C1)* 0.000 description 1
- 125000004637 2-oxopiperidinyl group Chemical group O=C1N(CCCC1)* 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- UOHYOICMAYOTIR-UHFFFAOYSA-N 3-chloro-5-methoxybenzamide Chemical compound COC1=CC(Cl)=CC(C(N)=O)=C1 UOHYOICMAYOTIR-UHFFFAOYSA-N 0.000 description 1
- MTQUEWJMXQAOIC-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-[(2,6-diaminopurin-7-yl)methyl]thiophene-2-carboxamide Chemical compound S1C=C(CN2C3=C(N)N=C(N)N=C3N=C2)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 MTQUEWJMXQAOIC-UHFFFAOYSA-N 0.000 description 1
- MMBDVBGJNUJKOG-UHFFFAOYSA-N 3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]-4-[[2-(ethylamino)imidazol-1-yl]methyl]thiophene-2-carboxamide Chemical compound CCNC1=NC=CN1CC1=CSC(C(=O)NC=2C(=CC(Cl)=CC=2OC)C(=O)NC=2N=CC(Cl)=CC=2)=C1Cl MMBDVBGJNUJKOG-UHFFFAOYSA-N 0.000 description 1
- YKHVIGACMSKZNP-UHFFFAOYSA-N 4-[(2-amino-5-oxo-4h-imidazol-3-yl)methyl]-3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]thiophene-2-carboxamide Chemical compound S1C=C(CN2C(NC(=O)C2)=N)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 YKHVIGACMSKZNP-UHFFFAOYSA-N 0.000 description 1
- OGSCMIPEKHJRLD-UHFFFAOYSA-N 4-[(6-aminopurin-7-yl)methyl]-3-chloro-n-[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]thiophene-2-carboxamide Chemical compound S1C=C(CN2C3=C(N)N=CN=C3N=C2)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 OGSCMIPEKHJRLD-UHFFFAOYSA-N 0.000 description 1
- 125000005986 4-piperidonyl group Chemical group 0.000 description 1
- ZMGMDXCADSRNCX-UHFFFAOYSA-N 5,6-dihydroxy-1,3-diazepan-2-one Chemical class OC1CNC(=O)NCC1O ZMGMDXCADSRNCX-UHFFFAOYSA-N 0.000 description 1
- JNVIARXKOSZILE-UHFFFAOYSA-N 5-amino-3-[[4-chloro-5-[[4-chloro-2-[(5-chloropyridin-2-yl)carbamoyl]-6-methoxyphenyl]carbamoyl]thiophen-3-yl]methyl]imidazole-4-carboxamide Chemical compound S1C=C(CN2C(=C(N)N=C2)C(N)=O)C(Cl)=C1C(=O)NC=1C(OC)=CC(Cl)=CC=1C(=O)NC1=CC=C(Cl)C=N1 JNVIARXKOSZILE-UHFFFAOYSA-N 0.000 description 1
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 208000036762 Acute promyelocytic leukaemia Diseases 0.000 description 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- 206010053567 Coagulopathies Diseases 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920002785 Croscarmellose sodium Polymers 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 108010048049 Factor IXa Proteins 0.000 description 1
- 108010014172 Factor V Proteins 0.000 description 1
- 108010054218 Factor VIII Proteins 0.000 description 1
- 102000001690 Factor VIII Human genes 0.000 description 1
- 108010074864 Factor XI Proteins 0.000 description 1
- 108010080805 Factor XIa Proteins 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 229920002683 Glycosaminoglycan Polymers 0.000 description 1
- 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 1
- 241000282412 Homo Species 0.000 description 1
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 description 1
- SNDPXSYFESPGGJ-BYPYZUCNSA-N L-2-aminopentanoic acid Chemical compound CCC[C@H](N)C(O)=O SNDPXSYFESPGGJ-BYPYZUCNSA-N 0.000 description 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 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
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
- ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 description 1
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- FFFHZYDWPBMWHY-VKHMYHEASA-N L-homocysteine Chemical compound OC(=O)[C@@H](N)CCS FFFHZYDWPBMWHY-VKHMYHEASA-N 0.000 description 1
- JTTHKOPSMAVJFE-VIFPVBQESA-N L-homophenylalanine Chemical compound OC(=O)[C@@H](N)CCC1=CC=CC=C1 JTTHKOPSMAVJFE-VIFPVBQESA-N 0.000 description 1
- UKAUYVFTDYCKQA-VKHMYHEASA-N L-homoserine Chemical compound OC(=O)[C@@H](N)CCO UKAUYVFTDYCKQA-VKHMYHEASA-N 0.000 description 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
- JZKXXXDKRQWDET-QMMMGPOBSA-N L-m-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC(O)=C1 JZKXXXDKRQWDET-QMMMGPOBSA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- SNDPXSYFESPGGJ-UHFFFAOYSA-N L-norVal-OH Natural products CCCC(N)C(O)=O SNDPXSYFESPGGJ-UHFFFAOYSA-N 0.000 description 1
- LRQKBLKVPFOOQJ-YFKPBYRVSA-N L-norleucine Chemical compound CCCC[C@H]([NH3+])C([O-])=O LRQKBLKVPFOOQJ-YFKPBYRVSA-N 0.000 description 1
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- 102000014962 Monocyte Chemoattractant Proteins Human genes 0.000 description 1
- 108010064136 Monocyte Chemoattractant Proteins Proteins 0.000 description 1
- 208000034578 Multiple myelomas Diseases 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-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
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-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
- 206010035226 Plasma cell myeloma Diseases 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920001030 Polyethylene Glycol 4000 Polymers 0.000 description 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
- 208000033826 Promyelocytic Acute Leukemia Diseases 0.000 description 1
- 108010007544 Protease Nexins Proteins 0.000 description 1
- 102000007324 Protease Nexins Human genes 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 206010040070 Septic Shock Diseases 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- 229940122055 Serine protease inhibitor Drugs 0.000 description 1
- 101710102218 Serine protease inhibitor Proteins 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 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
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
- 239000004473 Threonine Substances 0.000 description 1
- 229940122388 Thrombin inhibitor Drugs 0.000 description 1
- 102000003790 Thrombin receptors Human genes 0.000 description 1
- 108090000166 Thrombin receptors Proteins 0.000 description 1
- 208000032109 Transient ischaemic attack Diseases 0.000 description 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003275 alpha amino acid group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000001668 ameliorated effect Effects 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000001455 anti-clotting effect Effects 0.000 description 1
- 230000002429 anti-coagulating effect Effects 0.000 description 1
- 230000002785 anti-thrombosis Effects 0.000 description 1
- 229940127090 anticoagulant agent Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229960004676 antithrombotic agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 235000009582 asparagine Nutrition 0.000 description 1
- 229960001230 asparagine Drugs 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 125000002785 azepinyl group Chemical group 0.000 description 1
- 125000002393 azetidinyl group Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000003936 benzamides Chemical class 0.000 description 1
- 150000003937 benzamidines Chemical class 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 108090001015 cancer procoagulant Proteins 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000005482 chemotactic factor Substances 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000035602 clotting Effects 0.000 description 1
- 238000007820 coagulation assay Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000007887 coronary angioplasty Methods 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 229960001681 croscarmellose sodium Drugs 0.000 description 1
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 125000005507 decahydroisoquinolyl group Chemical group 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 125000004655 dihydropyridinyl group Chemical group N1(CC=CC=C1)* 0.000 description 1
- 150000004862 dioxolanes Chemical group 0.000 description 1
- 125000005879 dioxolanyl group Chemical group 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000001952 enzyme assay Methods 0.000 description 1
- 239000002532 enzyme inhibitor Substances 0.000 description 1
- 229940125532 enzyme inhibitor Drugs 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 229940012017 ethylenediamine Drugs 0.000 description 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 229960000301 factor viii Drugs 0.000 description 1
- 239000003527 fibrinolytic agent Substances 0.000 description 1
- 230000003480 fibrinolytic effect Effects 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 229960002743 glutamine Drugs 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 125000006492 halo alkyl aryl group Chemical group 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000023597 hemostasis Effects 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 229960002591 hydroxyproline Drugs 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 230000000937 inactivator Effects 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
- 125000001041 indolyl group Chemical group 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 229960000310 isoleucine Drugs 0.000 description 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000003965 isoxazolidinyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000008297 liquid dosage form Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 239000008176 lyophilized powder Substances 0.000 description 1
- 229960003646 lysine Drugs 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 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
- 239000011976 maleic acid Substances 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- JZKXXXDKRQWDET-UHFFFAOYSA-N meta-tyrosine Natural products OC(=O)C(N)CC1=CC=CC(O)=C1 JZKXXXDKRQWDET-UHFFFAOYSA-N 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000003226 mitogen Substances 0.000 description 1
- 208000010125 myocardial infarction Diseases 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
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 230000014508 negative regulation of coagulation Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000005060 octahydroindolyl group Chemical group N1(CCC2CCCCC12)* 0.000 description 1
- 125000005061 octahydroisoindolyl group Chemical group C1(NCC2CCCCC12)* 0.000 description 1
- 230000003287 optical effect Effects 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
- 230000000399 orthopedic effect Effects 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000005476 oxopyrrolidinyl group Chemical group 0.000 description 1
- 239000006179 pH buffering agent Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001639 phenylmethylene group Chemical group [H]C(=*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000003904 phospholipids Chemical group 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 229920002523 polyethylene Glycol 1000 Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 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
- 229960002429 proline Drugs 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
- 235000010388 propyl gallate Nutrition 0.000 description 1
- 229940075579 propyl gallate Drugs 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 150000003212 purines Chemical class 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
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 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
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 229940085605 saccharin sodium Drugs 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229960004559 theobromine Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000006090 thiamorpholinyl sulfone group Chemical group 0.000 description 1
- 125000006089 thiamorpholinyl sulfoxide group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 239000003868 thrombin inhibitor Substances 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
- 201000010875 transient cerebral ischemia Diseases 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 229940117013 triethanolamine oleate Drugs 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 108010036927 trypsin-like serine protease Proteins 0.000 description 1
- 229960004799 tryptophan Drugs 0.000 description 1
- 229960004441 tyrosine Drugs 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000003966 vascular damage Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
- C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US99428497A | 1997-12-19 | 1997-12-19 | |
US09/187,459 US6140351A (en) | 1997-12-19 | 1998-11-05 | Ortho-anthranilamide derivatives as anti-coagulants |
PCT/EP1998/007650 WO1999032477A1 (en) | 1997-12-19 | 1998-11-27 | Ortho-anthranilamide derivatives as anti-coagulants |
Publications (1)
Publication Number | Publication Date |
---|---|
SK9432000A3 true SK9432000A3 (en) | 2001-02-12 |
Family
ID=26883056
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SK943-2000A SK9432000A3 (en) | 1997-12-19 | 1998-11-27 | Ortho-anthranilamide derivatives as anti-coagulants, pharmaceutical composition containing such derivatives and use thereof |
Country Status (19)
Country | Link |
---|---|
US (2) | US6498185B1 (xx) |
EP (1) | EP1040108B1 (xx) |
JP (1) | JP3811006B2 (xx) |
CN (1) | CN1143855C (xx) |
AT (1) | ATE260103T1 (xx) |
AU (1) | AU751856B2 (xx) |
CA (1) | CA2315070A1 (xx) |
DE (1) | DE69821985T2 (xx) |
DK (1) | DK1040108T3 (xx) |
ES (1) | ES2215337T3 (xx) |
HU (1) | HUP0101172A3 (xx) |
IL (1) | IL135536A0 (xx) |
NO (1) | NO20003111L (xx) |
NZ (1) | NZ503809A (xx) |
PL (1) | PL341044A1 (xx) |
PT (1) | PT1040108E (xx) |
RU (1) | RU2226529C2 (xx) |
SK (1) | SK9432000A3 (xx) |
WO (1) | WO1999032477A1 (xx) |
Families Citing this family (79)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2214685C (en) | 1995-03-10 | 2008-05-20 | Berlex Laboratories, Inc. | Benzamidine derivatives their preparation and their use as anti-coagulants |
ES2188979T3 (es) | 1996-09-12 | 2003-07-01 | Schering Ag | Derivados de benzamidina sustituidos con derivados de aminoacidos ciclicos e hidroxiacidos ciclicos, y su uso como anti-coagulantes. |
US6004985A (en) | 1996-10-09 | 1999-12-21 | Berlex Laboratories, Inc. | Thio acid derived monocylic N-heterocyclics as anticoagulants |
JP2002512633A (ja) | 1997-06-26 | 2002-04-23 | イーライ・リリー・アンド・カンパニー | 抗血栓剤 |
ATE297203T1 (de) | 1997-06-26 | 2005-06-15 | Lilly Co Eli | Antithrombotische mitteln |
IL133625A0 (en) | 1997-06-26 | 2001-04-30 | Lilly Co Eli | Antithrombotic agents |
US6313151B1 (en) | 1997-06-26 | 2001-11-06 | Eli Lilly And Company | Antithrombotic agents |
US6291514B1 (en) | 1998-02-09 | 2001-09-18 | 3-Dimensional Pharmaceuticals, Inc. | Heteroaryl amidines, methylamidines and guanidines, preparation thereof, and use thereof as protease inhibitors |
GB9824579D0 (en) | 1998-11-10 | 1999-01-06 | Novartis Ag | Organic compounds |
US6127376A (en) | 1998-12-04 | 2000-10-03 | Berlex Laboratories, Inc. | Aryl and heterocyclyl substituted pyrimidine derivatives as anti-coagulants |
ATE326453T1 (de) | 1998-12-23 | 2006-06-15 | Lilly Co Eli | Antithrombotische amide |
JP2002533454A (ja) | 1998-12-23 | 2002-10-08 | イーライ・リリー・アンド・カンパニー | 芳香族アミド類 |
US6689780B1 (en) | 1998-12-23 | 2004-02-10 | Eli Lilly And Company | Heteroroaromatic amides as inhibitor of factor Xa |
EP1161412A1 (en) * | 1999-03-16 | 2001-12-12 | Glaxo Group Limited | Nuclear receptor arylating compounds |
CA2375920A1 (en) | 1999-06-14 | 2000-12-21 | Eli Lilly And Company | Compounds |
US6720317B1 (en) | 1999-09-17 | 2004-04-13 | Millennium Pharmaceuticals, Inc. | Inhibitors of factor Xa |
US6844367B1 (en) | 1999-09-17 | 2005-01-18 | Millennium Pharmaceuticals, Inc. | Benzamides and related inhibitors of factor Xa |
AU1770001A (en) * | 1999-11-24 | 2001-06-04 | Cor Therapeutics, Inc. | Beta-amino acid-, aspartic acid- and diaminopropionic-based inhibitors of factorxa |
DE60115394T2 (de) | 2000-02-29 | 2006-10-19 | Millennium Pharmaceuticals, Inc., Cambridge | Benzamide und ähnliche inhibitoren vom faktor xa |
MY138097A (en) * | 2000-03-22 | 2009-04-30 | Du Pont | Insecticidal anthranilamides |
AU776053B2 (en) | 2000-03-31 | 2004-08-26 | Astellas Pharma Inc. | Diazepan derivatives or salts thereof |
US7160878B2 (en) | 2000-07-27 | 2007-01-09 | Eli Lilly And Company | Substituted heterocyclic amides |
WO2002026731A2 (en) * | 2000-09-29 | 2002-04-04 | Millenium Pharmaceuticals, Inc. | Quaternary amidino based inhibitors of factor xa |
WO2002026712A2 (en) * | 2000-09-29 | 2002-04-04 | Millennium Pharmaceuticals, Inc. | Quaternary amines and related inhibitors of factor xa |
US6710058B2 (en) | 2000-11-06 | 2004-03-23 | Bristol-Myers Squibb Pharma Company | Monocyclic or bicyclic carbocycles and heterocycles as factor Xa inhibitors |
ATE323071T1 (de) * | 2000-11-22 | 2006-04-15 | Astellas Pharma Inc | Substituierte phenolderivate und deren salze als hemmstoffe von koagulations faktor x |
EP1379506A2 (en) * | 2000-11-28 | 2004-01-14 | Eli Lilly And Company | Substituted carboxamides |
DE10061876A1 (de) * | 2000-12-12 | 2002-06-20 | Aventis Pharma Gmbh | Arylierte Furan- und Thiophencarbonsäureamide, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament sowie sie enthaltende pharmazeutische Zubereitungen |
US6878714B2 (en) | 2001-01-12 | 2005-04-12 | Amgen Inc. | Substituted alkylamine derivatives and methods of use |
US7105682B2 (en) | 2001-01-12 | 2006-09-12 | Amgen Inc. | Substituted amine derivatives and methods of use |
US20030134836A1 (en) | 2001-01-12 | 2003-07-17 | Amgen Inc. | Substituted arylamine derivatives and methods of use |
US7102009B2 (en) | 2001-01-12 | 2006-09-05 | Amgen Inc. | Substituted amine derivatives and methods of use |
US6995162B2 (en) | 2001-01-12 | 2006-02-07 | Amgen Inc. | Substituted alkylamine derivatives and methods of use |
US6998408B2 (en) | 2001-03-23 | 2006-02-14 | Bristol-Myers Squibb Pharma Company | 6-5, 6-6, or 6-7 Heterobicycles as factor Xa inhibitors |
US6864255B2 (en) | 2001-04-11 | 2005-03-08 | Amgen Inc. | Substituted triazinyl amide derivatives and methods of use |
DE10121003A1 (de) * | 2001-04-28 | 2002-12-19 | Aventis Pharma Gmbh | Anthranilsäureamide, Verfahren zur Herstellung, ihrer Verwendung als Medikament sowie sie enthaltende pharmazeutische Zubereitungen |
SE0102764D0 (sv) | 2001-08-17 | 2001-08-17 | Astrazeneca Ab | Compounds |
TWI331526B (en) | 2001-09-21 | 2010-10-11 | Bristol Myers Squibb Pharma Co | Lactam-containing compounds and derivatives thereof as factor xa inhibitors |
ES2329881T3 (es) | 2001-09-21 | 2009-12-02 | Bristol-Myers Squibb Company | Compuestos que contienen lactama y derivados de los mismos como inhibidores del factor xa. |
TW200302225A (en) | 2001-12-04 | 2003-08-01 | Bristol Myers Squibb Co | Substituted amino methyl factor Xa inhibitors |
US7449457B2 (en) | 2001-12-07 | 2008-11-11 | Eli Lilly And Company | Substituted heterocyclic carboxamides with antithrombotic activity |
TW200307667A (en) | 2002-05-06 | 2003-12-16 | Bristol Myers Squibb Co | Sulfonylaminovalerolactams and derivatives thereof as factor Xa inhibitors |
US7312214B2 (en) | 2002-05-10 | 2007-12-25 | Bristol-Myers Squibb Company | 1, 1-disubstituted cycloalkyl derivatives as factor Xa inhibitors |
SE0201937D0 (sv) | 2002-06-20 | 2002-06-20 | Astrazeneca Ab | Therapeutic agents |
RU2004137094A (ru) | 2002-06-20 | 2005-08-10 | Астразенека Аб (Se) | Орто-замещенные производные бензойной кислоты для лечения инсулинорезистентности |
US7351858B2 (en) | 2002-06-20 | 2008-04-01 | Astrazeneca Ab | Ortho-substituted benzoic acid derivatives for the treatment of insulin resistance |
US7307088B2 (en) | 2002-07-09 | 2007-12-11 | Amgen Inc. | Substituted anthranilic amide derivatives and methods of use |
EP2982668A3 (en) | 2002-12-03 | 2016-04-13 | Pharmacyclics LLC | 2-(2-hydroxybiphenyl-3-yl)-1h-benzoimidazole-5-carboxamidine derivatives as factor viia inhibitors for the treatment of thromboembolic disorders |
US7696225B2 (en) | 2003-01-06 | 2010-04-13 | Osi Pharmaceuticals, Inc. | (2-carboxamido)(3-Amino) thiophene compounds |
TWI299664B (en) | 2003-01-06 | 2008-08-11 | Osi Pharm Inc | (2-carboxamido)(3-amino)thiophene compounds |
US7122557B2 (en) | 2003-03-18 | 2006-10-17 | Bristol-Myers Squibb Company | Sulfonyl-amidino-containing and tetrahydropyrimidino-containing compounds as factor Xa inhibitors |
US7205318B2 (en) | 2003-03-18 | 2007-04-17 | Bristol-Myers Squibb Company | Lactam-containing cyclic diamines and derivatives as a factor Xa inhibitors |
EP1479680A1 (en) * | 2003-05-19 | 2004-11-24 | Aventis Pharma Deutschland GmbH | Azaindole derivatives as Factor Xa inhibitors |
WO2005012256A1 (en) | 2003-07-22 | 2005-02-10 | Astex Therapeutics Limited | 3, 4-disubstituted 1h-pyrazole compounds and their use as cyclin dependent kinases (cdk) and glycogen synthase kinase-3 (gsk-3) modulators |
TW200512181A (en) * | 2003-09-26 | 2005-04-01 | Tanabe Seiyaku Co | Amide-type carboxamide derivatives |
TW200524915A (en) * | 2003-09-26 | 2005-08-01 | Tanabe Seiyaku Co | Carbamoyl-type benzofuran derivatives |
US7199149B2 (en) | 2003-10-01 | 2007-04-03 | Bristol Myers Squibb Company | Monocyclic and bicyclic lactams as factor Xa inhibitors |
US7507748B2 (en) * | 2004-07-22 | 2009-03-24 | Amgen Inc. | Substituted aryl-amine derivatives and methods of use |
US8404718B2 (en) | 2005-01-21 | 2013-03-26 | Astex Therapeutics Limited | Combinations of pyrazole kinase inhibitors |
AR054425A1 (es) | 2005-01-21 | 2007-06-27 | Astex Therapeutics Ltd | Sales de adicion de piperidin 4-il- amida de acido 4-(2,6-dicloro-benzoilamino) 1h-pirazol-3-carboxilico. |
DE602005013754D1 (de) * | 2005-05-13 | 2009-05-20 | Qosmos | Verkehrsanalyse in Hochgeschwindigkeitsnetzwerken |
US8247556B2 (en) | 2005-10-21 | 2012-08-21 | Amgen Inc. | Method for preparing 6-substituted-7-aza-indoles |
ATE544749T1 (de) | 2006-11-02 | 2012-02-15 | Millennium Pharm Inc | Verfahren zur synthetisierung pharmazeutischer salze aus einem faktor-xa-hemmer |
JP2010120852A (ja) * | 2007-03-09 | 2010-06-03 | Daiichi Sankyo Co Ltd | 新規なジアミド誘導体 |
WO2008135524A2 (en) * | 2007-05-02 | 2008-11-13 | Boehringer Ingelheim International Gmbh | Substituted anthranilamides and analogues, manufacturing and use thereof as medicaments |
WO2008156715A1 (en) * | 2007-06-20 | 2008-12-24 | Merck & Co., Inc. | Cetp inhibitors derived from benzoxazole arylamides |
BRPI0813952A2 (pt) | 2007-06-29 | 2017-05-09 | Gilead Sciences Inc | derivados de purina e seu emprego como moduladores e receptor 7 semelhante ao dobre de sino |
NZ612380A (en) | 2008-12-09 | 2015-01-30 | Gilead Sciences Inc | Modulators of toll-like receptors |
MX2012004706A (es) | 2009-10-22 | 2012-06-08 | Gilead Sciences Inc | Derivados de purina o deazapurina utiles para el tratamiento de (inter alia) infecciones virales. |
WO2012014109A1 (en) | 2010-07-30 | 2012-02-02 | Ranbaxy Laboratories Limited | Heterocyclic sulfonamides as inhibitors of transfer rna synthetase for use as antibacterial agents |
CA2816983A1 (en) | 2010-11-05 | 2012-05-10 | Senomyx, Inc. | Compounds useful as modulators of trpm8 |
UY34305A (es) | 2011-09-01 | 2013-04-30 | Novartis Ag | Derivados de heterociclos bicíclicos para el tratamiento de la hipertensión arterial pulmonar |
US9073921B2 (en) | 2013-03-01 | 2015-07-07 | Novartis Ag | Salt forms of bicyclic heterocyclic derivatives |
EP3054936B1 (en) | 2013-10-10 | 2023-10-18 | Eastern Virginia Medical School | 4-((2-hydroxy-3-methoxybenzyl)amino) benzenesulfonamide derivatives as 12-lipoxygenase inhibitors |
CN113577081A (zh) | 2014-07-11 | 2021-11-02 | 吉利德科学公司 | 用于治疗hiv的toll样受体调节剂 |
CN110305133A (zh) | 2014-09-16 | 2019-10-08 | 吉利德科学公司 | Toll样受体调节剂的固体形式 |
BR112018006471B1 (pt) | 2015-10-01 | 2024-02-27 | Senomyx, Inc | Composto, composição, método de modular o membro de melastina do canal potencial do receptor transitório 8 (trpm8), método de modular a sensação de resfrescância de uma composição e método de induzir uma sensação de refrescância em um ser humano ou animal |
KR102672512B1 (ko) | 2018-09-12 | 2024-06-10 | 노파르티스 아게 | 항바이러스 피리도피라진디온 화합물 |
AU2020353055B2 (en) | 2019-09-26 | 2024-03-07 | Gilead Sciences, Inc. | Antiviral pyrazolopyridinone compounds |
Family Cites Families (29)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB824908A (en) | 1958-06-03 | 1959-12-09 | May & Baker Ltd | Improvements in or relating to triazine derivatives |
JPS5922697B2 (ja) | 1976-01-13 | 1984-05-28 | エーザイ株式会社 | ビス−(メタ−アミジノフエノキシ)−化合物 |
DE69129611T2 (de) * | 1990-08-20 | 1998-12-17 | Eisai Co., Ltd., Tokio/Tokyo | Sulfonamid-Derivate |
EP0518818A3 (en) | 1991-06-11 | 1993-04-28 | Ciba-Geigy Ag | Arylethers, their manufacture and use as medicament |
US5451700A (en) | 1991-06-11 | 1995-09-19 | Ciba-Geigy Corporation | Amidino compounds, their manufacture and methods of treatment |
ZA928276B (en) * | 1991-10-31 | 1993-05-06 | Daiichi Seiyaku Co | Aromatic amidine derivates and salts thereof. |
DE69321344D1 (de) | 1992-02-14 | 1998-11-05 | Corvas Int Inc | Inhibitoren der thrombose |
DE4213919A1 (de) | 1992-04-28 | 1993-11-04 | Thomae Gmbh Dr K | Cyclische iminoderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
AU675981B2 (en) | 1992-12-02 | 1997-02-27 | Bristol-Myers Squibb Company | Guanidinyl-substituted heterocyclic thrombin inhibitors |
DE69324041D1 (de) | 1992-12-15 | 1999-04-22 | Corvas Int Inc | NEUE INHIBITOREN VON FAKTOR Xa |
US5332822A (en) | 1992-12-24 | 1994-07-26 | Bristol-Myers Squibb Company | Heteroaromatic and thioheteroaromatic substituted sulfonamide thrombin inhibitors |
WO1994017817A1 (en) | 1993-02-12 | 1994-08-18 | Corvas International, Inc. | Inhibitors of thrombosis |
US5633381A (en) | 1994-07-05 | 1997-05-27 | Berlex Laboratories, Inc. | (Z,Z), (Z,E) and (E,Z) isomers of substituted bis(phenylmethylene)cycloketones |
IL115420A0 (en) | 1994-09-26 | 1995-12-31 | Zeneca Ltd | Aminoheterocyclic derivatives |
US5691364A (en) | 1995-03-10 | 1997-11-25 | Berlex Laboratories, Inc. | Benzamidine derivatives and their use as anti-coagulants |
CA2214685C (en) | 1995-03-10 | 2008-05-20 | Berlex Laboratories, Inc. | Benzamidine derivatives their preparation and their use as anti-coagulants |
US5612363A (en) | 1995-06-02 | 1997-03-18 | Berlex Laboratories, Inc. | N,N-di(aryl) cyclic urea derivatives as anti-coagulants |
US5721214A (en) | 1995-06-07 | 1998-02-24 | Cor Therapeutics, Inc. | Inhibitors of factor Xa |
US5849759A (en) | 1995-12-08 | 1998-12-15 | Berlex Laboratories, Inc. | Naphthyl-substituted benzimidazole derivatives as anti-coagulants |
US5994375A (en) * | 1996-02-12 | 1999-11-30 | Berlex Laboratories, Inc. | Benzamidine derivatives substituted by amino acid and hydroxy acid derivatives and their use as anti-coagulants |
US5693641A (en) | 1996-08-16 | 1997-12-02 | Berlex Laboratories Inc. | Bicyclic pyrimidine derivatives and their use as anti-coagulants |
US5753635A (en) | 1996-08-16 | 1998-05-19 | Berlex Laboratories, Inc. | Purine derivatives and their use as anti-coagulants |
ES2188979T3 (es) | 1996-09-12 | 2003-07-01 | Schering Ag | Derivados de benzamidina sustituidos con derivados de aminoacidos ciclicos e hidroxiacidos ciclicos, y su uso como anti-coagulantes. |
US6004985A (en) | 1996-10-09 | 1999-12-21 | Berlex Laboratories, Inc. | Thio acid derived monocylic N-heterocyclics as anticoagulants |
ATE297203T1 (de) | 1997-06-26 | 2005-06-15 | Lilly Co Eli | Antithrombotische mitteln |
IL133625A0 (en) | 1997-06-26 | 2001-04-30 | Lilly Co Eli | Antithrombotic agents |
JP2002512633A (ja) * | 1997-06-26 | 2002-04-23 | イーライ・リリー・アンド・カンパニー | 抗血栓剤 |
US6140351A (en) * | 1997-12-19 | 2000-10-31 | Berlex Laboratories, Inc. | Ortho-anthranilamide derivatives as anti-coagulants |
CA2358095A1 (en) | 1998-12-23 | 2000-07-06 | Eli Lilly And Company | Heteroroaromatic amides as inhibitor of factor xa |
-
1998
- 1998-11-27 RU RU2000119756/04A patent/RU2226529C2/ru not_active IP Right Cessation
- 1998-11-27 CA CA002315070A patent/CA2315070A1/en not_active Abandoned
- 1998-11-27 AT AT98963519T patent/ATE260103T1/de not_active IP Right Cessation
- 1998-11-27 CN CNB988124173A patent/CN1143855C/zh not_active Expired - Fee Related
- 1998-11-27 WO PCT/EP1998/007650 patent/WO1999032477A1/en not_active Application Discontinuation
- 1998-11-27 NZ NZ503809A patent/NZ503809A/en unknown
- 1998-11-27 DK DK98963519T patent/DK1040108T3/da active
- 1998-11-27 EP EP98963519A patent/EP1040108B1/en not_active Expired - Lifetime
- 1998-11-27 DE DE69821985T patent/DE69821985T2/de not_active Expired - Fee Related
- 1998-11-27 AU AU18759/99A patent/AU751856B2/en not_active Ceased
- 1998-11-27 ES ES98963519T patent/ES2215337T3/es not_active Expired - Lifetime
- 1998-11-27 SK SK943-2000A patent/SK9432000A3/sk unknown
- 1998-11-27 JP JP2000525414A patent/JP3811006B2/ja not_active Expired - Fee Related
- 1998-11-27 PL PL98341044A patent/PL341044A1/xx not_active Application Discontinuation
- 1998-11-27 PT PT98963519T patent/PT1040108E/pt unknown
- 1998-11-27 HU HU0101172A patent/HUP0101172A3/hu unknown
- 1998-11-27 IL IL13553698A patent/IL135536A0/xx unknown
-
2000
- 2000-06-16 NO NO20003111A patent/NO20003111L/no not_active Application Discontinuation
- 2000-08-03 US US09/631,452 patent/US6498185B1/en not_active Expired - Fee Related
- 2000-08-03 US US09/631,450 patent/US6380221B1/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
CA2315070A1 (en) | 1999-07-01 |
EP1040108B1 (en) | 2004-02-25 |
PL341044A1 (en) | 2001-03-26 |
AU1875999A (en) | 1999-07-12 |
DK1040108T3 (da) | 2004-05-24 |
AU751856B2 (en) | 2002-08-29 |
JP2001526283A (ja) | 2001-12-18 |
WO1999032477B1 (en) | 1999-09-10 |
ATE260103T1 (de) | 2004-03-15 |
WO1999032477A1 (en) | 1999-07-01 |
US6380221B1 (en) | 2002-04-30 |
RU2226529C2 (ru) | 2004-04-10 |
JP3811006B2 (ja) | 2006-08-16 |
NZ503809A (en) | 2002-04-26 |
HUP0101172A3 (en) | 2002-12-28 |
IL135536A0 (en) | 2001-05-20 |
US6498185B1 (en) | 2002-12-24 |
EP1040108A1 (en) | 2000-10-04 |
NO20003111L (no) | 2000-08-18 |
CN1282329A (zh) | 2001-01-31 |
DE69821985D1 (de) | 2004-04-01 |
CN1143855C (zh) | 2004-03-31 |
PT1040108E (pt) | 2004-06-30 |
HUP0101172A1 (hu) | 2002-05-29 |
ES2215337T3 (es) | 2004-10-01 |
DE69821985T2 (de) | 2005-05-04 |
NO20003111D0 (no) | 2000-06-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
SK9432000A3 (en) | Ortho-anthranilamide derivatives as anti-coagulants, pharmaceutical composition containing such derivatives and use thereof | |
US6140351A (en) | Ortho-anthranilamide derivatives as anti-coagulants | |
AU760370B2 (en) | Aryl and heterocyclyl substituted pyrimidine derivatives as anti-coagulants | |
US5612363A (en) | N,N-di(aryl) cyclic urea derivatives as anti-coagulants | |
US8247562B2 (en) | Benzamide derivatives useful as histone deacetylase inhibitors | |
AU724413B2 (en) | Bicyclic pyrimidine derivatives and their use as anti-coagulants | |
US5089499A (en) | Quinazoline derivatives possessing anti-tumor activity | |
US7732483B2 (en) | DNA-PK inhibitors | |
PT1501508E (pt) | Inibidores da desacetilase da histona. | |
SK29599A3 (en) | Benzamidine derivatives substituted by cyclic amino acid or cyclic hydroxy acid derivatives and their use as anti-coagulants | |
SK281474B6 (sk) | Deriváty arylalkyldiazinónu, spôsob ich prípravy, farmaceutický prostriedok, ktorý ich obsahuje, a ich použitie | |
NO312834B1 (no) | Forbindelser og farmasöytisk preparat inneholdende nevnte forbindelse som er nyttig ved behandling av et menneske med ensykdomstilstand kjennetegnet ved trombotisk virkning | |
US5395838A (en) | 6-substituted quinazolines processing anti-tumor activity | |
CZ20002292A3 (cs) | Ortho-anthranilamidové deriváty jako protisrážecí činidla, farmaceutický prostředek obsahující tyto deriváty a jejich použití |