JP2008503497A5 - - Google Patents
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- Publication number
- JP2008503497A5 JP2008503497A5 JP2007516824A JP2007516824A JP2008503497A5 JP 2008503497 A5 JP2008503497 A5 JP 2008503497A5 JP 2007516824 A JP2007516824 A JP 2007516824A JP 2007516824 A JP2007516824 A JP 2007516824A JP 2008503497 A5 JP2008503497 A5 JP 2008503497A5
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- methyl
- thiophene
- phenyl
- ylmethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 98
- DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 claims 78
- -1 5-chloro-thiophene-2-carbonyl Chemical group 0.000 claims 54
- QZLSBOVWPHXCLT-UHFFFAOYSA-N 5-chlorothiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(Cl)S1 QZLSBOVWPHXCLT-UHFFFAOYSA-N 0.000 claims 48
- 150000001875 compounds Chemical class 0.000 claims 35
- 125000003118 aryl group Chemical group 0.000 claims 32
- 229910052799 carbon Inorganic materials 0.000 claims 31
- 229910052739 hydrogen Inorganic materials 0.000 claims 28
- 125000003342 alkenyl group Chemical group 0.000 claims 26
- 125000000304 alkynyl group Chemical group 0.000 claims 26
- 229910052736 halogen Inorganic materials 0.000 claims 22
- 125000001072 heteroaryl group Chemical group 0.000 claims 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 19
- 125000004429 atom Chemical group 0.000 claims 18
- 150000002367 halogens Chemical class 0.000 claims 18
- 125000001424 substituent group Chemical group 0.000 claims 18
- 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 claims 16
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 16
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 16
- 125000002947 alkylene group Chemical group 0.000 claims 14
- 125000005842 heteroatom Chemical group 0.000 claims 12
- 229920006395 saturated elastomer Polymers 0.000 claims 12
- 229910052757 nitrogen Inorganic materials 0.000 claims 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 9
- 125000004450 alkenylene group Chemical group 0.000 claims 8
- 125000004419 alkynylene group Chemical group 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 239000002253 acid Substances 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 230000001732 thrombotic effect Effects 0.000 claims 6
- 125000002619 bicyclic group Chemical group 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000002950 monocyclic group Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- ANFXTILBDGTSEG-UHFFFAOYSA-N 1-methyl-4,5-dihydroimidazole Chemical compound CN1CCN=C1 ANFXTILBDGTSEG-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 239000005973 Carvone Substances 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 206010047249 Venous thrombosis Diseases 0.000 claims 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 2
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 230000000414 obstructive effect Effects 0.000 claims 2
- SRJOCJYGOFTFLH-UHFFFAOYSA-M piperidine-4-carboxylate Chemical compound [O-]C(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-M 0.000 claims 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims 2
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 claims 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 claims 1
- YKEUGLWLUOBQBO-UHFFFAOYSA-N 1-[4-[5-[[(5-chlorothiophene-2-carbonyl)-methylamino]methyl]-1,2-oxazol-3-yl]benzenecarboximidoyl]piperidine-4-carboxamide Chemical compound C=1C=C(Cl)SC=1C(=O)N(C)CC(ON=1)=CC=1C(C=C1)=CC=C1C(=N)N1CCC(C(N)=O)CC1 YKEUGLWLUOBQBO-UHFFFAOYSA-N 0.000 claims 1
- JDMIDRYFIZZOPG-UHFFFAOYSA-N 1-[4-[5-[[(5-chlorothiophene-2-carbonyl)amino]methyl]-5-methyl-4h-1,2-oxazol-3-yl]benzenecarboximidoyl]piperidine-4-carboxamide Chemical compound C1C(C=2C=CC(=CC=2)C(=N)N2CCC(CC2)C(N)=O)=NOC1(C)CNC(=O)C1=CC=C(Cl)S1 JDMIDRYFIZZOPG-UHFFFAOYSA-N 0.000 claims 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims 1
- LSKKKVJQYWNBPC-UHFFFAOYSA-N 2-[4-[5-(aminomethyl)-4,5-dihydro-1,2-oxazol-3-yl]phenyl]aniline Chemical compound O1C(CN)CC(C=2C=CC(=CC=2)C=2C(=CC=CC=2)N)=N1 LSKKKVJQYWNBPC-UHFFFAOYSA-N 0.000 claims 1
- ISDPNZYGSWEDQE-UHFFFAOYSA-N 2-[5-(aminomethyl)-4,5-dihydro-1,2-oxazol-3-yl]-N-(2-methoxyethyl)-N-methyl-5-(pyrrolidine-1-carboximidoyl)aniline Chemical compound CN(CCOC)C(C=C(C=C1)C(N2CCCC2)=N)=C1C1=NOC(CN)C1 ISDPNZYGSWEDQE-UHFFFAOYSA-N 0.000 claims 1
- NJBMZYSKLWQXLJ-UHFFFAOYSA-N 3,4-dihydro-2h-pyrrol-5-amine Chemical compound NC1=NCCC1 NJBMZYSKLWQXLJ-UHFFFAOYSA-N 0.000 claims 1
- BXEAAHIHFFIMIE-UHFFFAOYSA-N 3-chlorothiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC=CC=1Cl BXEAAHIHFFIMIE-UHFFFAOYSA-N 0.000 claims 1
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims 1
- DPBWFNDFMCCGGJ-UHFFFAOYSA-N 4-Piperidine carboxamide Chemical compound NC(=O)C1CCNCC1 DPBWFNDFMCCGGJ-UHFFFAOYSA-N 0.000 claims 1
- JALWZTSZNDTGPF-UHFFFAOYSA-N 4-[5-(1-aminoethyl)-1,2-oxazol-3-yl]-N,N-dimethylbenzenecarboximidamide Chemical compound CC(C1=CC(C(C=C2)=CC=C2C(N(C)C)=N)=NO1)N JALWZTSZNDTGPF-UHFFFAOYSA-N 0.000 claims 1
- APDDNMVSAJDMHQ-UHFFFAOYSA-N 4-[5-(aminomethyl)-1,2-oxazol-3-yl]-N-(furan-2-ylmethyl)-N-methylbenzenecarboximidamide Chemical compound CN(CC1=CC=CO1)C(C(C=C1)=CC=C1C1=NOC(CN)=C1)=N APDDNMVSAJDMHQ-UHFFFAOYSA-N 0.000 claims 1
- YBJRJGFEWRSPQZ-UHFFFAOYSA-N 4-[5-(aminomethyl)-4,5-dihydro-1,2-oxazol-3-yl]-N-phenylaniline Chemical compound O1C(CN)CC(C=2C=CC(NC=3C=CC=CC=3)=CC=2)=N1 YBJRJGFEWRSPQZ-UHFFFAOYSA-N 0.000 claims 1
- CJAYGHZIHKWLRM-UHFFFAOYSA-N 4-[5-[[(5-chlorothiophene-2-carbonyl)amino]methyl]-1,2-oxazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=NOC(CNC(=O)C=2SC(Cl)=CC=2)=C1 CJAYGHZIHKWLRM-UHFFFAOYSA-N 0.000 claims 1
- WMSNMRKQRRALOR-UHFFFAOYSA-N 4-[5-[[(5-chlorothiophene-2-carbonyl)amino]methyl]-4,5-dihydro-1,2-oxazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1)=NOC1CNC(=O)C1=CC=C(Cl)S1 WMSNMRKQRRALOR-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
- 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 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- JDZQSFHESPSHGS-CQSZACIVSA-N 5-chloro-n-[(1r)-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-CQSZACIVSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- BPZBWVROIASGRE-UHFFFAOYSA-N 5-chloro-n-[(3-piperidin-4-yl-1,2-oxazol-5-yl)methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CC(C2CCNCC2)=NO1 BPZBWVROIASGRE-UHFFFAOYSA-N 0.000 claims 1
- FWTLMKYPVLMXPV-UHFFFAOYSA-N 5-chloro-n-[(5-methyl-3-phenyl-4h-1,2-oxazol-5-yl)methyl]thiophene-2-carboxamide Chemical compound C1C(C=2C=CC=CC=2)=NOC1(C)CNC(=O)C1=CC=C(Cl)S1 FWTLMKYPVLMXPV-UHFFFAOYSA-N 0.000 claims 1
- JOHRRRPRAMPJDT-UHFFFAOYSA-N 5-chloro-n-[[1-(2-fluoro-4-iodophenyl)triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound FC1=CC(I)=CC=C1N1N=NC(CNC(=O)C=2SC(Cl)=CC=2)=C1 JOHRRRPRAMPJDT-UHFFFAOYSA-N 0.000 claims 1
- YYJGXWCCLNYFCK-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CN(C=2C=CC(=CC=2)N2C(C=CC=C2)=O)N=N1 YYJGXWCCLNYFCK-UHFFFAOYSA-N 0.000 claims 1
- ZBMIYUAPAJWWCW-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(3-fluoro-2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound O=C1C(F)=CC=CN1C1=CC=C(N2N=NC(CNC(=O)C=3SC(Cl)=CC=3)=C2)C=C1 ZBMIYUAPAJWWCW-UHFFFAOYSA-N 0.000 claims 1
- UZMGHDTZBZWTLE-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(3-methoxy-2-oxopyridin-1-yl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound O=C1C(OC)=CC=CN1C1=CC=C(N2N=NC(CNC(=O)C=3SC(Cl)=CC=3)=C2)C=C1 UZMGHDTZBZWTLE-UHFFFAOYSA-N 0.000 claims 1
- YCHGXGYRJQEUFO-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(n,n-dimethylcarbamimidoyl)-2-fluorophenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound FC1=CC(C(=N)N(C)C)=CC=C1N1N=NC(CNC(=O)C=2SC(Cl)=CC=2)=C1 YCHGXGYRJQEUFO-UHFFFAOYSA-N 0.000 claims 1
- FCZZAWFYUPMFRJ-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(n,n-dimethylcarbamimidoyl)phenyl]imidazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C(=N)N(C)C)=CC=C1N1C=C(CNC(=O)C=2SC(Cl)=CC=2)N=C1 FCZZAWFYUPMFRJ-UHFFFAOYSA-N 0.000 claims 1
- IECMQWIJSLBQTB-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(n,n-dimethylcarbamimidoyl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C(=N)N(C)C)=CC=C1N1N=NC(CNC(=O)C=2SC(Cl)=CC=2)=C1 IECMQWIJSLBQTB-UHFFFAOYSA-N 0.000 claims 1
- DKPKSCPYXZELQR-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(n-ethyl-n-methylcarbamimidoyl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C(=N)N(C)CC)=CC=C1N1N=NC(CNC(=O)C=2SC(Cl)=CC=2)=C1 DKPKSCPYXZELQR-UHFFFAOYSA-N 0.000 claims 1
- XACCSEMIBCHTLY-UHFFFAOYSA-N 5-chloro-n-[[1-[4-(n-methyl-n-propylcarbamimidoyl)phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C(=N)N(C)CCC)=CC=C1N1N=NC(CNC(=O)C=2SC(Cl)=CC=2)=C1 XACCSEMIBCHTLY-UHFFFAOYSA-N 0.000 claims 1
- JNDLTSOWZJQRCM-UHFFFAOYSA-N 5-chloro-n-[[1-[4-[n-(2-methoxyethyl)-n-methylcarbamimidoyl]phenyl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C(=N)N(C)CCOC)=CC=C1N1N=NC(CNC(=O)C=2SC(Cl)=CC=2)=C1 JNDLTSOWZJQRCM-UHFFFAOYSA-N 0.000 claims 1
- NFAYBIHYYPDCTC-UHFFFAOYSA-N 5-chloro-n-[[1-[6-(1,4-diazepan-1-yl)pyridin-3-yl]triazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1=CN(C=2C=NC(=CC=2)N2CCNCCC2)N=N1 NFAYBIHYYPDCTC-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- CWTNDXMQQYSCEV-UHFFFAOYSA-N 5-chloro-n-[[2-[4-(n'-methylcarbamimidoyl)phenyl]-1,3-thiazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C(=N)NC)=CC=C1C1=NC(CNC(=O)C=2SC(Cl)=CC=2)=CS1 CWTNDXMQQYSCEV-UHFFFAOYSA-N 0.000 claims 1
- OKNBNCGDLMBZPB-UHFFFAOYSA-N 5-chloro-n-[[2-[4-(n,n-dimethylcarbamimidoyl)phenyl]-1,3-oxazol-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)=CO1 OKNBNCGDLMBZPB-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- QBQFSPLIKXDKLS-UHFFFAOYSA-N 5-chloro-n-[[2-[4-(n-ethyl-n-methylcarbamimidoyl)phenyl]-1,3-oxazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C(=N)N(C)CC)=CC=C1C1=NC(CNC(=O)C=2SC(Cl)=CC=2)=CO1 QBQFSPLIKXDKLS-UHFFFAOYSA-N 0.000 claims 1
- DNUOUGWTTQSDHI-UHFFFAOYSA-N 5-chloro-n-[[2-[4-(n-methyl-n-propylcarbamimidoyl)phenyl]-1,3-oxazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C(=N)N(C)CCC)=CC=C1C1=NC(CNC(=O)C=2SC(Cl)=CC=2)=CO1 DNUOUGWTTQSDHI-UHFFFAOYSA-N 0.000 claims 1
- BCGUAGZSUHGTND-UHFFFAOYSA-N 5-chloro-n-[[2-[4-[n-(2-methoxyethyl)-n-methylcarbamimidoyl]phenyl]-1,3-oxazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C(=N)N(C)CCOC)=CC=C1C1=NC(CNC(=O)C=2SC(Cl)=CC=2)=CO1 BCGUAGZSUHGTND-UHFFFAOYSA-N 0.000 claims 1
- UINGTWKMPIRNOO-UHFFFAOYSA-N 5-chloro-n-[[2-[4-[n-[2-(dimethylamino)ethyl]-n-methylcarbamimidoyl]phenyl]-1,3-oxazol-4-yl]methyl]thiophene-2-carboxamide Chemical compound C1=CC(C(=N)N(C)CCN(C)C)=CC=C1C1=NC(CNC(=O)C=2SC(Cl)=CC=2)=CO1 UINGTWKMPIRNOO-UHFFFAOYSA-N 0.000 claims 1
- CBHIZCCVQPRKQY-UHFFFAOYSA-N 5-chloro-n-[[3-(1-ethanimidoylpiperidin-4-yl)-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1CN(C(=N)C)CCC1C1=NOC(CNC(=O)C=2SC(Cl)=CC=2)=C1 CBHIZCCVQPRKQY-UHFFFAOYSA-N 0.000 claims 1
- YYEKSTWSMGGSDD-UHFFFAOYSA-N 5-chloro-n-[[3-(1-ethanimidoylpiperidin-4-yl)-4,5-dihydro-1,2-oxazol-5-yl]methyl]thiophene-2-carboxamide Chemical compound C1CN(C(=N)C)CCC1C(C1)=NOC1CNC(=O)C1=CC=C(Cl)S1 YYEKSTWSMGGSDD-UHFFFAOYSA-N 0.000 claims 1
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| KR101195801B1 (ko) | 2004-06-18 | 2012-11-05 | 밀레니엄 파머슈티컬스 인코퍼레이티드 | Ｘａ 인자 억제제 |
| AP2007004244A0 (en) | 2005-05-10 | 2007-12-31 | Intermune Inc | Method of modulating stress-activated protein kinase system |
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| JP2009528273A (ja) * | 2006-01-25 | 2009-08-06 | シンタ ファーマシューティカルズ コーポレーション | 炎症および免疫関連使用用の置換ビアリール化合物 |
| US8748627B2 (en) | 2006-02-15 | 2014-06-10 | Abbvie Inc. | Acetyl-CoA carboxylase (ACC) inhibitors and their use in diabetes, obesity and metabolic syndrome |
| US8735595B2 (en) | 2006-02-15 | 2014-05-27 | Abbvie Inc. | Acetyl-CoA carboxylase (ACC) inhibitors and their use in diabetes, obesity and metabolic syndrome |
| WO2007112367A2 (en) * | 2006-03-27 | 2007-10-04 | Portola Pharmaceuticals, Inc. | Potassium channel modulators and platelet procoagulant activity |
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| DE102006025314A1 (de) * | 2006-05-31 | 2007-12-06 | Bayer Healthcare Ag | Arylsubstituierte Heterozyklen und ihre Verwendung |
| DE102006039589A1 (de) * | 2006-08-24 | 2008-03-06 | Bayer Healthcare Ag | Aminoacyl-Prodrugs II |
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| EP2077995B1 (en) | 2006-11-02 | 2012-02-08 | Millennium Pharmaceuticals, Inc. | Methods of synthesizing pharmaceutical salts of a factor xa inhibitor |
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| EP2155195B1 (en) | 2007-04-13 | 2014-07-16 | Millennium Pharmaceuticals, Inc. | Combination anticoagulant therapy with a compound that acts as a factor Xa inhibitor |
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| ES2569660T3 (es) | 2007-06-08 | 2016-05-12 | Mannkind Corporation | Inhibidores de la IRE-1alfa |
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2005
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- 2005-06-20 CN CNA2005800190908A patent/CN1968922A/zh active Pending
- 2005-06-20 CA CA002565437A patent/CA2565437A1/en not_active Abandoned
- 2005-06-20 JP JP2007516824A patent/JP5020073B2/ja not_active Expired - Fee Related
- 2005-06-20 BR BRPI0512273-2A patent/BRPI0512273A/pt not_active Application Discontinuation
- 2005-06-20 AU AU2005257999A patent/AU2005257999B2/en not_active Ceased
- 2005-06-20 WO PCT/US2005/021817 patent/WO2006002099A2/en not_active Ceased
- 2005-06-20 US US11/158,274 patent/US7521470B2/en not_active Expired - Fee Related
- 2005-06-20 MX MXPA06013960A patent/MXPA06013960A/es active IP Right Grant
- 2005-06-20 NZ NZ552187A patent/NZ552187A/en not_active IP Right Cessation
- 2005-06-20 EP EP05762149.2A patent/EP1893572B1/en not_active Expired - Lifetime
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2006
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2009
- 2009-01-05 US US12/348,879 patent/US8153670B2/en not_active Expired - Fee Related
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2011
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