AU2005257999B2 - Factor Xa inhibitors - Google Patents

Info

Publication number

AU2005257999B2

AU2005257999B2 AU2005257999A AU2005257999A AU2005257999B2 AU 2005257999 B2 AU2005257999 B2 AU 2005257999B2 AU 2005257999 A AU2005257999 A AU 2005257999A AU 2005257999 A AU2005257999 A AU 2005257999A AU 2005257999 B2 AU2005257999 B2 AU 2005257999B2

Authority

AU

Australia

Prior art keywords

thiophene

chloro

methyl

phenyl

isoxazol

Prior art date

2004-06-18

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Ceased

Links

• Espacenet
• Global Dossier
• Discuss

• 229940123583 Factor Xa inhibitor Drugs 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 540
• 238000000034 method Methods 0.000 claims abstract description 409
• 150000003839 salts Chemical class 0.000 claims abstract description 40
• 208000007536 Thrombosis Diseases 0.000 claims abstract description 12
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 9
• 230000015271 coagulation Effects 0.000 claims abstract description 7
• 238000005345 coagulation Methods 0.000 claims abstract description 7
• 210000004369 blood Anatomy 0.000 claims abstract description 5
• 239000008280 blood Substances 0.000 claims abstract description 5
• QZLSBOVWPHXCLT-UHFFFAOYSA-N 5-chlorothiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(Cl)S1 QZLSBOVWPHXCLT-UHFFFAOYSA-N 0.000 claims description 289
• 125000000217 alkyl group Chemical group 0.000 claims description 169
• -1 SR 4 a Chemical group 0.000 claims description 144
• 239000000203 mixture Substances 0.000 claims description 135
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 114
• DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 claims description 89
• 125000003118 aryl group Chemical group 0.000 claims description 67
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 64
• 229910052799 carbon Inorganic materials 0.000 claims description 59
• 229910052739 hydrogen Inorganic materials 0.000 claims description 57
• 125000001072 heteroaryl group Chemical group 0.000 claims description 53
• 229910052757 nitrogen Inorganic materials 0.000 claims description 53
• 229910052736 halogen Inorganic materials 0.000 claims description 52
• 125000001424 substituent group Chemical group 0.000 claims description 52
• 150000002367 halogens Chemical class 0.000 claims description 48
• 125000000304 alkynyl group Chemical group 0.000 claims description 42
• 125000003342 alkenyl group Chemical group 0.000 claims description 39
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 34
• 125000004429 atom Chemical group 0.000 claims description 33
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 32
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 30
• 125000001188 haloalkyl group Chemical group 0.000 claims description 30
• 125000005842 heteroatom Chemical group 0.000 claims description 30
• 125000002947 alkylene group Chemical group 0.000 claims description 28
• 229920006395 saturated elastomer Polymers 0.000 claims description 28
• 241000005308 Orsa Species 0.000 claims description 22
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 21
• 125000004076 pyridyl group Chemical group 0.000 claims description 21
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
• 125000000623 heterocyclic group Chemical group 0.000 claims description 19
• 239000001257 hydrogen Substances 0.000 claims description 19
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 18
• 239000002253 acid Substances 0.000 claims description 18
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 15
• 125000004419 alkynylene group Chemical group 0.000 claims description 15
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
• 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 13
• 125000004450 alkenylene group Chemical group 0.000 claims description 12
• 150000001408 amides Chemical class 0.000 claims description 12
• 150000003857 carboxamides Chemical class 0.000 claims description 10
• 241000124008 Mammalia Species 0.000 claims description 9
• 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 9
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 9
• 125000004434 sulfur atom Chemical group 0.000 claims description 9
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 8
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
• AVRWEULSKHQETA-UHFFFAOYSA-N Thiophene-2 Chemical compound S1C=2CCCCCC=2C(C(=O)OC)=C1NC(=O)C1=C(F)C(F)=C(F)C(F)=C1F AVRWEULSKHQETA-UHFFFAOYSA-N 0.000 claims description 8
• 239000003146 anticoagulant agent Substances 0.000 claims description 8
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
• 125000002619 bicyclic group Chemical group 0.000 claims description 8
• 125000002950 monocyclic group Chemical group 0.000 claims description 8
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 7
• 229910052760 oxygen Inorganic materials 0.000 claims description 7
• 239000001301 oxygen Substances 0.000 claims description 7
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
• JXCWLIAYTJNSCN-LLVKDONJSA-N 5-chloro-n-[(1r)-1-[3-[4-(n,n-dimethylcarbamimidoyl)phenyl]-1,2-oxazol-5-yl]ethyl]thiophene-2-carboxamide Chemical compound N([C@H](C)C=1ON=C(C=1)C=1C=CC(=CC=1)C(=N)N(C)C)C(=O)C1=CC=C(Cl)S1 JXCWLIAYTJNSCN-LLVKDONJSA-N 0.000 claims description 6
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
• 125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• OUNMNPJHCJJQDB-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(n,n-dimethylcarbamimidoyl)phenyl]-1,2,4-oxadiazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C(=N)N(C)C)=CC=C1C1=NOC(CNC(=O)C=2SC(Cl)=CC=2)=N1 OUNMNPJHCJJQDB-UHFFFAOYSA-N 0.000 claims description 5
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 5
• 229910052740 iodine Inorganic materials 0.000 claims description 5
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 5
• 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 5
• 125000001359 1,2,3-triazol-4-yl group Chemical group [H]N1N=NC([*])=C1[H] 0.000 claims description 4
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
• CUGPZFCLPBNJEQ-UHFFFAOYSA-N 5-chloro-n-[[2-[4-(n,n-dimethylcarbamimidoyl)phenyl]-1,3-thiazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C(=N)N(C)C)=CC=C1C1=NC(CNC(=O)C=2SC(Cl)=CC=2)=CS1 CUGPZFCLPBNJEQ-UHFFFAOYSA-N 0.000 claims description 4
• GMTKXQAGCSCJPQ-UHFFFAOYSA-N 5-chloro-n-[[2-[4-(piperidine-1-carboximidoyl)phenyl]-1,3-oxazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=COC(C=2C=CC(=CC=2)C(=N)N2CCCCC2)=N1 GMTKXQAGCSCJPQ-UHFFFAOYSA-N 0.000 claims description 4
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000005843 halogen group Chemical group 0.000 claims description 4
• MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 4
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 4
• 229930192474 thiophene Natural products 0.000 claims description 4
• 230000001732 thrombotic effect Effects 0.000 claims description 4
• BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims description 3
• YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 claims description 3
• FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 3
• QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 3
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
• WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims description 3
• NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 3
• YOLBFWGXNKIVNM-GFCCVEGCSA-N 5-chloro-n-[(1r)-1-[3-[4-(1-methyl-4,5-dihydroimidazol-2-yl)phenyl]-1,2-oxazol-5-yl]ethyl]thiophene-2-carboxamide Chemical compound N([C@H](C)C=1ON=C(C=1)C=1C=CC(=CC=1)C=1N(CCN=1)C)C(=O)C1=CC=C(Cl)S1 YOLBFWGXNKIVNM-GFCCVEGCSA-N 0.000 claims description 3
• GXDPYGDAAUOKND-CYBMUJFWSA-N 5-chloro-n-[(1r)-1-[3-[4-(pyrrolidine-1-carboximidoyl)phenyl]-1,2-oxazol-5-yl]ethyl]thiophene-2-carboxamide Chemical compound N([C@H](C)C=1ON=C(C=1)C=1C=CC(=CC=1)C(=N)N1CCCC1)C(=O)C1=CC=C(Cl)S1 GXDPYGDAAUOKND-CYBMUJFWSA-N 0.000 claims description 3
• JDZQSFHESPSHGS-AWEZNQCLSA-N 5-chloro-n-[(1s)-1-[3-[4-(piperidine-1-carboximidoyl)phenyl]-1,2-oxazol-5-yl]ethyl]thiophene-2-carboxamide Chemical compound N([C@@H](C)C=1ON=C(C=1)C=1C=CC(=CC=1)C(=N)N1CCCCC1)C(=O)C1=CC=C(Cl)S1 JDZQSFHESPSHGS-AWEZNQCLSA-N 0.000 claims description 3
• GXDPYGDAAUOKND-ZDUSSCGKSA-N 5-chloro-n-[(1s)-1-[3-[4-(pyrrolidine-1-carboximidoyl)phenyl]-1,2-oxazol-5-yl]ethyl]thiophene-2-carboxamide Chemical compound N([C@@H](C)C=1ON=C(C=1)C=1C=CC(=CC=1)C(=N)N1CCCC1)C(=O)C1=CC=C(Cl)S1 GXDPYGDAAUOKND-ZDUSSCGKSA-N 0.000 claims description 3
• ZIZBWBUESVSKIA-UHFFFAOYSA-N 5-chloro-n-[(3-phenyl-1,2-oxazol-5-yl)methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CC(C=2C=CC=CC=2)=NO1 ZIZBWBUESVSKIA-UHFFFAOYSA-N 0.000 claims description 3
• WCXXGOULPJCIGY-UHFFFAOYSA-N 5-chloro-n-[(3-phenyl-4,5-dihydro-1,2-oxazol-5-yl)methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1ON=C(C=2C=CC=CC=2)C1 WCXXGOULPJCIGY-UHFFFAOYSA-N 0.000 claims description 3
• MNCYIAKMBZKHGF-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(pyrrolidine-1-carboximidoyl)phenyl]pyrazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CN(C=2C=CC(=CC=2)C(=N)N2CCCC2)N=C1 MNCYIAKMBZKHGF-UHFFFAOYSA-N 0.000 claims description 3
• BYLLOIJFABXYGG-UHFFFAOYSA-N 5-chloro-n-[[2-[4-(n'-methylcarbamimidoyl)phenyl]-1,3-oxazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C(=N)NC)=CC=C1C1=NC(CNC(=O)C=2SC(Cl)=CC=2)=CO1 BYLLOIJFABXYGG-UHFFFAOYSA-N 0.000 claims description 3
• VGLFJWWCTJLMFU-UHFFFAOYSA-N 5-chloro-n-[[2-[4-(piperidine-1-carboximidoyl)phenyl]-1,3-thiazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CSC(C=2C=CC(=CC=2)C(=N)N2CCCCC2)=N1 VGLFJWWCTJLMFU-UHFFFAOYSA-N 0.000 claims description 3
• ZYICNRUPDOYIPV-UHFFFAOYSA-N 5-chloro-n-[[3-(4-methylphenyl)-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C)=CC=C1C1=NOC(CNC(=O)C=2SC(Cl)=CC=2)=C1 ZYICNRUPDOYIPV-UHFFFAOYSA-N 0.000 claims description 3
• UPEIREKSUWZFLA-UHFFFAOYSA-N 5-chloro-n-[[3-[2-(4-methoxyphenoxy)-4-(1-methyl-4,5-dihydroimidazol-2-yl)phenyl]-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(OC)=CC=C1OC1=CC(C=2N(CCN=2)C)=CC=C1C1=NOC(CNC(=O)C=2SC(Cl)=CC=2)=C1 UPEIREKSUWZFLA-UHFFFAOYSA-N 0.000 claims description 3
• ORRYOIPQAUMAJM-UHFFFAOYSA-N 5-chloro-n-[[3-[2-[2-methoxyethyl(methyl)amino]-4-(piperidine-1-carboximidoyl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound COCCN(C)C1=CC(C(=N)N2CCCCC2)=CC=C1C(C1)=NOC1CNC(=O)C1=CC=C(Cl)S1 ORRYOIPQAUMAJM-UHFFFAOYSA-N 0.000 claims description 3
• HILFIDCKPQRSBN-UHFFFAOYSA-N 5-chloro-n-[[3-[2-morpholin-4-yl-4-(piperidine-1-carboximidoyl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1ON=C(C=2C(=CC(=CC=2)C(=N)N2CCCCC2)N2CCOCC2)C1 HILFIDCKPQRSBN-UHFFFAOYSA-N 0.000 claims description 3
• DGFYHIQGPLXYSL-UHFFFAOYSA-N 5-chloro-n-[[3-[3-[3-(pyrrolidin-1-ylmethyl)phenyl]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1ON=C(C=2C=C(C=CC=2)C=2C=C(CN3CCCC3)C=CC=2)C1 DGFYHIQGPLXYSL-UHFFFAOYSA-N 0.000 claims description 3
• QHNRSFGRCCAAKC-UHFFFAOYSA-N 5-chloro-n-[[3-[3-[3-[(dimethylamino)methyl]phenyl]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound CN(C)CC1=CC=CC(C=2C=C(C=CC=2)C=2CC(CNC(=O)C=3SC(Cl)=CC=3)ON=2)=C1 QHNRSFGRCCAAKC-UHFFFAOYSA-N 0.000 claims description 3
• REUPOHYXLFSZJP-UHFFFAOYSA-N 5-chloro-n-[[3-[3-[4-[(dimethylamino)methyl]phenyl]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(CN(C)C)=CC=C1C1=CC=CC(C=2CC(CNC(=O)C=3SC(Cl)=CC=3)ON=2)=C1 REUPOHYXLFSZJP-UHFFFAOYSA-N 0.000 claims description 3
• XZHFOSZHBZGJRI-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(1-methyl-4,5-dihydroimidazol-2-yl)phenyl]-1,2,4-oxadiazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound CN1CCN=C1C1=CC=C(C=2N=C(CNC(=O)C=3SC(Cl)=CC=3)ON=2)C=C1 XZHFOSZHBZGJRI-UHFFFAOYSA-N 0.000 claims description 3
• IAOZMHAUCOEXDM-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(1-methyl-4,5-dihydroimidazol-2-yl)phenyl]-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound CN1CCN=C1C1=CC=C(C2=NOC(CNC(=O)C=3SC(Cl)=CC=3)=C2)C=C1 IAOZMHAUCOEXDM-UHFFFAOYSA-N 0.000 claims description 3
• LWIDVUORNBJLOB-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(1-methyl-4,5-dihydroimidazol-2-yl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound CN1CCN=C1C1=CC=C(C=2CC(CNC(=O)C=3SC(Cl)=CC=3)ON=2)C=C1 LWIDVUORNBJLOB-UHFFFAOYSA-N 0.000 claims description 3
• NUVJMIBVNCPYMW-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(2-hydroxypropylcarbamoyl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C(=O)NCC(O)C)=CC=C1C(C1)=NOC1CNC(=O)C1=CC=C(Cl)S1 NUVJMIBVNCPYMW-UHFFFAOYSA-N 0.000 claims description 3
• LUSPCGRDHXMKJY-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(2-oxopiperidin-1-yl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1ON=C(C=2C=CC(=CC=2)N2C(CCCC2)=O)C1 LUSPCGRDHXMKJY-UHFFFAOYSA-N 0.000 claims description 3
• UKEKHFSLGDMCIL-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(3-fluoro-2-oxopyridin-1-yl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound O=C1C(F)=CC=CN1C1=CC=C(C=2CC(CNC(=O)C=3SC(Cl)=CC=3)ON=2)C=C1 UKEKHFSLGDMCIL-UHFFFAOYSA-N 0.000 claims description 3
• SQWAXWWILGFCAD-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(3-oxothiomorpholin-4-yl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1ON=C(C=2C=CC(=CC=2)N2C(CSCC2)=O)C1 SQWAXWWILGFCAD-UHFFFAOYSA-N 0.000 claims description 3
• NLLKWWGYKMKWPW-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(4-methylpiperazin-1-yl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1CN(C)CCN1C1=CC=C(C=2CC(CNC(=O)C=3SC(Cl)=CC=3)ON=2)C=C1 NLLKWWGYKMKWPW-UHFFFAOYSA-N 0.000 claims description 3
• UYBXIEBGKLSQQE-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(5-oxo-1,4-oxazepan-4-yl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1ON=C(C=2C=CC(=CC=2)N2C(CCOCC2)=O)C1 UYBXIEBGKLSQQE-UHFFFAOYSA-N 0.000 claims description 3
• FIKDOEJUEKNPOM-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(dimethylcarbamoyl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1C(C1)=NOC1CNC(=O)C1=CC=C(Cl)S1 FIKDOEJUEKNPOM-UHFFFAOYSA-N 0.000 claims description 3
• MNKZOCZFZNBYSR-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(n-ethyl-n-methylcarbamimidoyl)phenyl]-1,2-oxazol-5-yl]methyl]-n-methylthiophene-2-carboxamide Chemical compound C1=CC(C(=N)N(C)CC)=CC=C1C1=NOC(CN(C)C(=O)C=2SC(Cl)=CC=2)=C1 MNKZOCZFZNBYSR-UHFFFAOYSA-N 0.000 claims description 3
• KLPCOHDGCZTCLN-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(n-ethyl-n-methylcarbamimidoyl)phenyl]-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C(=N)N(C)CC)=CC=C1C1=NOC(CNC(=O)C=2SC(Cl)=CC=2)=C1 KLPCOHDGCZTCLN-UHFFFAOYSA-N 0.000 claims description 3
• BRLNVERJKAQSFT-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(n-ethyl-n-methylcarbamimidoyl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C(=N)N(C)CC)=CC=C1C(C1)=NOC1CNC(=O)C1=CC=C(Cl)S1 BRLNVERJKAQSFT-UHFFFAOYSA-N 0.000 claims description 3
• ALRBMEROMCWTLS-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(piperidine-1-carboximidoyl)phenyl]-1,2,4-oxadiazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=NC(C=2C=CC(=CC=2)C(=N)N2CCCCC2)=NO1 ALRBMEROMCWTLS-UHFFFAOYSA-N 0.000 claims description 3
• AUMAMPZKKXJRJQ-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(quinolin-6-ylamino)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1ON=C(C=2C=CC(NC=3C=C4C=CC=NC4=CC=3)=CC=2)C1 AUMAMPZKKXJRJQ-UHFFFAOYSA-N 0.000 claims description 3
• CSYHBMZYVBMMBW-UHFFFAOYSA-N 5-chloro-n-[[3-[4-[(1-methylpiperidin-4-yl)amino]phenyl]-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1CN(C)CCC1NC1=CC=C(C2=NOC(CNC(=O)C=3SC(Cl)=CC=3)=C2)C=C1 CSYHBMZYVBMMBW-UHFFFAOYSA-N 0.000 claims description 3
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• DRJRZOGOFCVNIS-UHFFFAOYSA-N 5-chloro-n-[[3-[4-[2-[[2-methoxyethyl(methyl)amino]methyl]phenyl]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound COCCN(C)CC1=CC=CC=C1C1=CC=C(C=2CC(CNC(=O)C=3SC(Cl)=CC=3)ON=2)C=C1 DRJRZOGOFCVNIS-UHFFFAOYSA-N 0.000 claims description 3
• ZVMSJANFBJSXAK-UHFFFAOYSA-N 5-chloro-n-[[3-[4-[5-chloro-2-(pyrrolidin-1-ylmethyl)phenyl]phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1ON=C(C=2C=CC(=CC=2)C=2C(=CC=C(Cl)C=2)CN2CCCC2)C1 ZVMSJANFBJSXAK-UHFFFAOYSA-N 0.000 claims description 3
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• CXKYBSLAKKMNTG-UHFFFAOYSA-N 5-chloro-n-[[3-[4-[n-[2-(dimethylamino)ethyl]-n-methylcarbamimidoyl]phenyl]-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C(=N)N(C)CCN(C)C)=CC=C1C1=NOC(CNC(=O)C=2SC(Cl)=CC=2)=C1 CXKYBSLAKKMNTG-UHFFFAOYSA-N 0.000 claims description 3
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• PLUQXAVPUABDRW-UHFFFAOYSA-N 5-chloro-n-[[5-[4-(piperidine-1-carboximidoyl)phenyl]-1,2-oxazol-3-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=NOC(C=2C=CC(=CC=2)C(=N)N2CCCCC2)=C1 PLUQXAVPUABDRW-UHFFFAOYSA-N 0.000 claims description 3
• BJQHCKGENCUFOZ-UHFFFAOYSA-N 5-chloro-n-methyl-n-[[3-[4-(pyrrolidine-1-carboximidoyl)phenyl]-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C=1C=C(Cl)SC=1C(=O)N(C)CC(ON=1)=CC=1C(C=C1)=CC=C1C(=N)N1CCCC1 BJQHCKGENCUFOZ-UHFFFAOYSA-N 0.000 claims description 3
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• 206010047249 Venous thrombosis Diseases 0.000 claims description 3
• KSAQXKVBGSGAJE-UHFFFAOYSA-N ethyl 1-[4-[4-[[(5-chlorothiophene-2-carbonyl)amino]methyl]-1,3-oxazol-2-yl]benzenecarboximidoyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C(=N)C1=CC=C(C=2OC=C(CNC(=O)C=3SC(Cl)=CC=3)N=2)C=C1 KSAQXKVBGSGAJE-UHFFFAOYSA-N 0.000 claims description 3
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• ZDWFKXNWDXPFCR-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(2-chlorophenyl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1ON=C(C=2C=CC(=CC=2)C=2C(=CC=CC=2)Cl)C1 ZDWFKXNWDXPFCR-UHFFFAOYSA-N 0.000 claims description 2
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• BKYUOBYEVIZXQZ-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(n,n-dimethylcarbamimidoyl)phenyl]-1,2-oxazol-5-yl]methyl]-n-methylthiophene-2-carboxamide Chemical compound C1=CC(C(=N)N(C)C)=CC=C1C1=NOC(CN(C)C(=O)C=2SC(Cl)=CC=2)=C1 BKYUOBYEVIZXQZ-UHFFFAOYSA-N 0.000 claims description 2
• QZNYLUWSJIIOKD-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(n-methyl-n-propylcarbamimidoyl)phenyl]-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C(=N)N(C)CCC)=CC=C1C1=NOC(CNC(=O)C=2SC(Cl)=CC=2)=C1 QZNYLUWSJIIOKD-UHFFFAOYSA-N 0.000 claims description 2
• LVVDVBHNRZMULC-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(n-methyl-n-propylcarbamimidoyl)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C(=N)N(C)CCC)=CC=C1C(C1)=NOC1CNC(=O)C1=CC=C(Cl)S1 LVVDVBHNRZMULC-UHFFFAOYSA-N 0.000 claims description 2
• FYLSIKFVVJUVFK-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(pyridin-3-ylamino)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1ON=C(C=2C=CC(NC=3C=NC=CC=3)=CC=2)C1 FYLSIKFVVJUVFK-UHFFFAOYSA-N 0.000 claims description 2
• VMDXZEFVYNRDHC-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(pyridin-4-ylamino)phenyl]-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1ON=C(C=2C=CC(NC=3C=CN=CC=3)=CC=2)C1 VMDXZEFVYNRDHC-UHFFFAOYSA-N 0.000 claims description 2
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• SDAJHHWYLHUSOZ-UHFFFAOYSA-N 5-chloro-n-[[3-[4-(pyrrolidine-1-carboximidoyl)phenyl]-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CC(C=2C=CC(=CC=2)C(=N)N2CCCC2)=NO1 SDAJHHWYLHUSOZ-UHFFFAOYSA-N 0.000 claims description 2
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