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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| JP5020073B2 (ja) | 2004-06-18 | 2012-09-05 | ミレニアム ファーマシューティカルズ インク． | 第Ｘａ因子阻害剤 |
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| MX2007014114A (es) | 2005-05-10 | 2008-03-14 | Intermune Inc | Derivados de piridona para modular el sistema de proteina cinasa activada por estres. |
| WO2007007588A1 (ja) * | 2005-07-08 | 2007-01-18 | Ono Pharmaceutical Co., Ltd. | 平面性を有する環状基を母核とする化合物 |
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| CN101384568B (zh) | 2006-02-15 | 2012-12-12 | 雅培制药有限公司 | 乙酰辅酶a羧化酶(acc)抑制剂及其在糖尿病、肥胖症和代谢综合征中的应用 |
| CN103554095A (zh) | 2006-02-15 | 2014-02-05 | Abbvie公司 | 新的乙酰辅酶a羧化酶(acc)抑制剂及其在糖尿病、肥胖症和代谢综合征中的应用 |
| US20090186810A1 (en) * | 2006-03-27 | 2009-07-23 | Portola Pharmaceuticals, Inc. | Potassium channel modulators and platelet procoagulant activity |
| EA015942B1 (ru) * | 2006-05-05 | 2011-12-30 | Милленниум Фамэсьютикэлс, Инк. | Замещенные имидазолы, композиция на их основе, способ профилактики или лечения нежелательного тромбообразования с их помощью и способ ингибирования коагуляции образцов крови |
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| US20080242694A1 (en) * | 2006-09-18 | 2008-10-02 | D Sidocky Neil R | Amino-substituted heterocycles, compositions thereof, and methods of treatment therewith |
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| PT2077995E (pt) * | 2006-11-02 | 2012-05-10 | Millennium Pharm Inc | Métodos de sintetizar sais farmacêuticos de um inibidor de fator xa |
| EP2114930A2 (en) * | 2007-01-05 | 2009-11-11 | Millennium Pharmaceuticals, Inc. | Factor xa inhibitors |
| CN101743001B (zh) * | 2007-04-13 | 2013-02-06 | 千年药品公司 | 用起因子xa抑制剂作用的化合物的组合抗凝治疗 |
| NZ599556A (en) * | 2007-05-02 | 2013-10-25 | Portola Pharm Inc | Combination therapy with a compound acting as a platelet adp receptor inhibitor |
| CA2963784A1 (en) | 2007-06-08 | 2008-12-18 | Mannkind Corporation | Ire-1.alpha. inhibitors |
| DE102007028319A1 (de) * | 2007-06-20 | 2008-12-24 | Bayer Healthcare Ag | Substituierte Oxazolidinone und ihre Verwendung |
| DE102007028406A1 (de) | 2007-06-20 | 2008-12-24 | Bayer Healthcare Ag | Substituierte Oxazolidinone und ihre Verwendung |
| DE102007028407A1 (de) * | 2007-06-20 | 2008-12-24 | Bayer Healthcare Ag | Substituierte Oxazolidinone und ihre Verwendung |
| CA2713139C (en) | 2008-02-01 | 2013-04-23 | Amira Pharmaceuticals, Inc. | N,n-disubstituted aminoalkylbiphenyl antagonists of prostaglandin d2 receptors |
| PE20091653A1 (es) * | 2008-03-26 | 2009-11-14 | Takeda Pharmaceutical | Derivados sustituidos de pirazol y su uso |
| US20110071197A1 (en) * | 2008-04-16 | 2011-03-24 | Peter Nilsson | Bis-aryl compounds for use as medicaments |
| JP5627574B2 (ja) * | 2008-06-03 | 2014-11-19 | インターミューン， インコーポレイテッド | 炎症性および線維性疾患を治療するための化合物および方法 |
| GB2463788B (en) | 2008-09-29 | 2010-12-15 | Amira Pharmaceuticals Inc | Heteroaryl antagonists of prostaglandin D2 receptors |
| WO2010039977A2 (en) | 2008-10-01 | 2010-04-08 | Amira Pharmaceuticals, Inc. | Heteroaryl antagonists of prostaglandin d2 receptors |
| WO2010042652A2 (en) | 2008-10-08 | 2010-04-15 | Amira Pharmaceuticals, Inc. | Heteroalkyl biphenyl antagonists of prostaglandin d2 receptors |
| CN102596902A (zh) | 2009-08-05 | 2012-07-18 | 潘米拉制药公司 | Dp2拮抗剂及其用途 |
| WO2011075602A1 (en) * | 2009-12-17 | 2011-06-23 | Millennium Pharmaceuticals, Inc. | Methods of preparing factor xa inhibitors and salts thereof |
| WO2011084652A2 (en) * | 2009-12-17 | 2011-07-14 | Millennium Pharmaceuticals, Inc. | Salts and crystalline forms of a factor xa inhibitor |
| US8394964B2 (en) | 2009-12-17 | 2013-03-12 | Millennium Pharmaceuticals, Inc. | Methods of synthesizing factor Xa inhibitors |
| DE102010028362A1 (de) | 2010-04-29 | 2011-11-03 | Bayer Schering Pharma Aktiengesellschaft | Herstellverfahren |
| ES2626601T3 (es) | 2010-06-28 | 2017-07-25 | Bayer Intellectual Property Gmbh | Compuestos heterocíclicos como pesticidas |
| AR082803A1 (es) | 2010-09-01 | 2013-01-09 | Portola Pharm Inc | Metodos y formulaciones para el tratamiento de la trombosis con betrixaban y un inhibidor de la glicoproteina p |
| TW201221128A (en) | 2010-09-01 | 2012-06-01 | Portola Pharm Inc | Crystalline forms of a factor Xa inhibitor |
| CN102219753B (zh) * | 2011-04-21 | 2012-10-31 | 山东大学 | 一种三氮唑类化合物及其制备方法与应用 |
| US20150224091A1 (en) | 2011-08-31 | 2015-08-13 | Portola Pharmaceuticals, Inc. | Prevention and treatment of thrombosis in medically ill patients |
| ES2716008T3 (es) | 2012-07-18 | 2019-06-07 | Sunshine Lake Pharma Co Ltd | Derivados heterocíclicos nitrogenados y su aplicación en fármacos |
| AR092742A1 (es) | 2012-10-02 | 2015-04-29 | Intermune Inc | Piridinonas antifibroticas |
| WO2014089364A1 (en) | 2012-12-06 | 2014-06-12 | Quanticel Pharmaceuticals, Inc | Histone demethylase inhibitors |
| US10233195B2 (en) | 2014-04-02 | 2019-03-19 | Intermune, Inc. | Anti-fibrotic pyridinones |
| WO2015172196A1 (en) * | 2014-05-13 | 2015-11-19 | Monash University | Heterocyclic compounds and use of same |
| CN104045634A (zh) * | 2014-06-06 | 2014-09-17 | 浙江工业大学 | 含二氟甲基吡唑甲酰胺类化合物及其制备方法和用途 |
| EP3268360B1 (en) | 2015-03-09 | 2019-04-24 | Bristol-Myers Squibb Company | Lactams as inhibitors of rock |
| EP3078378B1 (en) | 2015-04-08 | 2020-06-24 | Vaiomer | Use of factor xa inhibitors for regulating glycemia |
| CA2988147C (en) | 2015-06-03 | 2023-06-13 | Bristol-Myers Squibb Company | 4-hydroxy-3-(heteroaryl)pyridine-2-one apj agonists for use in the treatment of cardiovascular disorders |
| AR109304A1 (es) | 2016-08-10 | 2018-11-21 | Sumitomo Chemical Co | Compuesto de oxadiazol y su uso |
| WO2019036024A1 (en) | 2017-08-17 | 2019-02-21 | Bristol-Myers Squibb Company | 2- (1,1'-BIPHENYL) -1H-BENZO [D] IMIDAZOLE DERIVATIVES AND RELATED COMPOUNDS AS AGONISTS OF APELIN AND APJ FOR THE TREATMENT OF CARDIOVASCULAR DISEASES |
| AR119774A1 (es) * | 2019-08-19 | 2022-01-12 | Pi Industries Ltd | Compuestos de oxadiazol que contienen un anillo heteroaromático de 5 miembros para controlar o prevenir hongos fitopatogénicos |
| CN118496197A (zh) | 2019-12-20 | 2024-08-16 | 拜耳公司 | 取代的噻吩甲酰胺、噻吩甲酸及其衍生物 |
| EP4077317B1 (en) | 2019-12-20 | 2024-06-26 | Bayer Aktiengesellschaft | Thienyloxazolones and analogues |
| BR112022019041A2 (pt) * | 2020-03-23 | 2022-12-27 | Praxis Prec Medicines Inc | Inibidores de kcnt1 e métodos de uso |
| WO2021207031A1 (en) * | 2020-04-05 | 2021-10-14 | Coagulo Medical Technologies, Inc. | Methods of treating and preventing coronavirus infections using inhibitors of coagulation factor xa |
| US12319655B2 (en) | 2021-12-09 | 2025-06-03 | Deciphera Pharmaceuticals, Llc | RAF kinase inhibitors and methods of use thereof |
| CN118221605A (zh) * | 2022-12-20 | 2024-06-21 | 浙江省化工研究院有限公司 | 一类含异噁唑啉类化合物、其制备方法及应用 |
| EP4393919A1 (en) * | 2022-12-27 | 2024-07-03 | Exscientia Al Limited | Lsd1 modulators |
| AR132248A1 (es) * | 2023-03-29 | 2025-06-11 | Merck Sharp & Dohme Llc | Inhibidores de il4i1 y métodos para su uso |
Family Cites Families (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4588587A (en) | 1983-03-01 | 1986-05-13 | Pennsylvania Hospital | Method of treatment to inhibit metastasis |
| CA2151044A1 (en) | 1992-12-15 | 1994-06-23 | Terence K. Brunck | Novel inhibitors for factor xa |
| NZ296210A (en) | 1994-12-02 | 1998-05-27 | Yamanouchi Pharma Co Ltd | Amidinonaphthyl derivatives to inhibit activated blood coagulation factor x |
| US5849759A (en) | 1995-12-08 | 1998-12-15 | Berlex Laboratories, Inc. | Naphthyl-substituted benzimidazole derivatives as anti-coagulants |
| CN1246847A (zh) | 1996-12-23 | 2000-03-08 | 杜邦药品公司 | 作为Xa因子抑制剂的含氮杂芳族化合物 |
| US6514977B1 (en) * | 1997-05-22 | 2003-02-04 | G.D. Searle & Company | Substituted pyrazoles as p38 kinase inhibitors |
| EP1020434A4 (en) | 1997-08-27 | 2000-11-15 | Kissei Pharmaceutical | 3-AMIDINOANILINE DERIVATIVES, INHIBITORS OF THE ACTIVATED BLOOD COINTENANCE FACTOR X AND INTERMEDIATE PRODUCTS FOR PRODUCING BOTH |
| GB9725244D0 (en) | 1997-11-29 | 1998-01-28 | Zeneca Ltd | Chemical compounds |
| JP2000178243A (ja) * | 1998-12-14 | 2000-06-27 | Teijin Ltd | ビフェニルアミジン誘導体 |
| US6844367B1 (en) * | 1999-09-17 | 2005-01-18 | Millennium Pharmaceuticals, Inc. | Benzamides and related inhibitors of factor Xa |
| WO2001021160A2 (en) | 1999-09-23 | 2001-03-29 | Axxima Pharmaceuticals Aktiengesellschaft | Carboxymide and aniline derivatives as selective inhibitors of pathogens |
| DE19962924A1 (de) * | 1999-12-24 | 2001-07-05 | Bayer Ag | Substituierte Oxazolidinone und ihre Verwendung |
| ES2254385T3 (es) * | 2000-02-29 | 2006-06-16 | Millennium Pharmaceuticals, Inc. | Benzamidas e inhibidores relacionados del factor xa. |
| DE10027151A1 (de) | 2000-05-31 | 2001-12-06 | Bayer Ag | Herbizide Mittel auf Basis von substituierten Carbonsäureamiden |
| AU2001273040A1 (en) | 2000-06-27 | 2002-01-08 | Du Pont Pharmaceuticals Company | Factor xa inhibitors |
| EP1217000A1 (en) * | 2000-12-23 | 2002-06-26 | Aventis Pharma Deutschland GmbH | Inhibitors of factor Xa and factor VIIa |
| DE10105989A1 (de) * | 2001-02-09 | 2002-08-14 | Bayer Ag | Substituierte Oxazolidinone und ihre Verwendung |
| US7312235B2 (en) * | 2001-03-30 | 2007-12-25 | Millennium Pharmaceuticals, Inc. | Benzamide inhibitors of factor Xa |
| DE10129725A1 (de) | 2001-06-20 | 2003-01-02 | Bayer Ag | Kombinationstherapie substituierter Oxazolidinone |
| ES2180456B1 (es) | 2001-07-20 | 2004-05-01 | Laboratorios S.A.L.V.A.T., S.A. | Isoxazoles sustituidos y su utilizacion como antibioticos. |
| US6914058B2 (en) | 2002-01-18 | 2005-07-05 | Dr. Reddy's Laboratories, Limited | Antibacterial compounds: process for their preparation and pharmaceutical compositions containing them |
| US20050171358A1 (en) * | 2002-03-07 | 2005-08-04 | Noriko Shimozono | Substituted isoxazole alkylamine derivative and agri-and horticultural fungicide |
| JP3090812U (ja) * | 2002-06-18 | 2002-12-26 | アルプス電気株式会社 | 高周波モジュール |
| EP1616862A4 (en) * | 2003-04-18 | 2008-07-16 | Ono Pharmaceutical Co | HETEROCYCLIC NITROGEN COMPOUND AND USE THEREOF |
| WO2004101531A1 (en) | 2003-04-29 | 2004-11-25 | Dr. Reddy's Laboratories Ltd. | Antiinfective 1,2,3-triazole derivatives, process for their preparation and pharmaceutical compositions containing them |
| DE10322469A1 (de) * | 2003-05-19 | 2004-12-16 | Bayer Healthcare Ag | Heterocyclische Verbindungen |
| WO2004106329A2 (en) | 2003-06-03 | 2004-12-09 | Dr. Reddy's Laboratories Ltd. | Novel antiinfective compounds and their pharmaceutical compositions |
| US7199149B2 (en) | 2003-10-01 | 2007-04-03 | Bristol Myers Squibb Company | Monocyclic and bicyclic lactams as factor Xa inhibitors |
| CN1886398A (zh) * | 2003-10-09 | 2006-12-27 | 米伦纽姆医药公司 | 作为Xa因子抑制剂的经硫醚取代的苯甲酰胺 |
| WO2005035528A2 (en) | 2003-10-14 | 2005-04-21 | Dr. Reddy's Laboratories Ltd. | Triazole derivatives as antibacterial agents |
| WO2005082892A2 (en) | 2004-02-17 | 2005-09-09 | Dr. Reddy's Laboratories Ltd. | Triazole compounds as antibacterial agents and pharmaceutical compositions containing them |
| US7696352B2 (en) * | 2004-06-18 | 2010-04-13 | Millennium Pharmaceuticals, Inc. | Factor Xa inhibitors |
| JP5020073B2 (ja) | 2004-06-18 | 2012-09-05 | ミレニアム ファーマシューティカルズ インク． | 第Ｘａ因子阻害剤 |
| JP2008528691A (ja) | 2005-02-02 | 2008-07-31 | ビテ ファーマシューティカルズ， インコーポレイテッド | レニン阻害剤としての１−アシルアミノ−２−ヒドロキシ−３−アミノ−ω−アリールアルカン |
| WO2007007588A1 (ja) | 2005-07-08 | 2007-01-18 | Ono Pharmaceutical Co., Ltd. | 平面性を有する環状基を母核とする化合物 |
| AR057976A1 (es) | 2005-08-29 | 2008-01-09 | Boehringer Ingelheim Int | Biarilos sustituidos y su uso como medicamentos. |
| JP2007060967A (ja) | 2005-08-30 | 2007-03-15 | Tokyo Institute Of Technology | 遺伝子多型の検出方法および薬物のスクリーニング方法 |
| US8058284B2 (en) | 2005-11-03 | 2011-11-15 | Portola Pharmaceuticals, Inc. | [4-(6-halo-7-substituted-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-phenyl]-5-chloro-thiophen-2-yl-sulfonylureas and forms and methods related thereto |
| RU2440986C2 (ru) * | 2005-11-08 | 2012-01-27 | Милленниум Фамэсьютикэлс, Инк. | СОЛЬ ИНГИБИТОРА ФАКТОРА Ха, СПОСОБ ЕЕ ПОЛУЧЕНИЯ, ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ НА ЕЕ ОСНОВЕ, СОСТОЯЩИЕ ИЗ НАЗВАННОЙ КОМПОЗИЦИИ ТАБЛЕТКА, КАПСУЛА И ЛЕПЕШКА, СПОСОБ ЛЕЧЕНИЯ ТРОМБОЗА И СПОСОБ ИНГИБИРОВАНИЯ КОАГУЛЯЦИИ ОБРАЗЦОВ КРОВИ |
| US20090186810A1 (en) | 2006-03-27 | 2009-07-23 | Portola Pharmaceuticals, Inc. | Potassium channel modulators and platelet procoagulant activity |
| EA015942B1 (ru) | 2006-05-05 | 2011-12-30 | Милленниум Фамэсьютикэлс, Инк. | Замещенные имидазолы, композиция на их основе, способ профилактики или лечения нежелательного тромбообразования с их помощью и способ ингибирования коагуляции образцов крови |
| DE102006025314A1 (de) | 2006-05-31 | 2007-12-06 | Bayer Healthcare Ag | Arylsubstituierte Heterozyklen und ihre Verwendung |
| US20080051578A1 (en) | 2006-08-24 | 2008-02-28 | Georg Dahmann | Substituted biaryls, process for their manufacture and use thereof as medicaments |
| NZ578180A (en) * | 2006-12-08 | 2012-02-24 | Millennium Pharm Inc | Unit dose formulations and methods of treating thrombosis with an oral factor xa inhibitor |
| EP2114930A2 (en) * | 2007-01-05 | 2009-11-11 | Millennium Pharmaceuticals, Inc. | Factor xa inhibitors |
| CN101743001B (zh) * | 2007-04-13 | 2013-02-06 | 千年药品公司 | 用起因子xa抑制剂作用的化合物的组合抗凝治疗 |
| NZ599556A (en) * | 2007-05-02 | 2013-10-25 | Portola Pharm Inc | Combination therapy with a compound acting as a platelet adp receptor inhibitor |
-
2005
- 2005-06-20 JP JP2007516824A patent/JP5020073B2/ja not_active Expired - Fee Related
- 2005-06-20 NZ NZ552187A patent/NZ552187A/en not_active IP Right Cessation
- 2005-06-20 MX MXPA06013960A patent/MXPA06013960A/es active IP Right Grant
- 2005-06-20 WO PCT/US2005/021817 patent/WO2006002099A2/en not_active Ceased
- 2005-06-20 KR KR1020077001313A patent/KR101195801B1/ko not_active Expired - Fee Related
- 2005-06-20 AU AU2005257999A patent/AU2005257999B2/en not_active Ceased
- 2005-06-20 BR BRPI0512273-2A patent/BRPI0512273A/pt not_active Application Discontinuation
- 2005-06-20 CN CNA2005800190908A patent/CN1968922A/zh active Pending
- 2005-06-20 US US11/158,274 patent/US7521470B2/en not_active Expired - Fee Related
- 2005-06-20 CA CA002565437A patent/CA2565437A1/en not_active Abandoned
- 2005-06-20 EP EP05762149.2A patent/EP1893572B1/en not_active Expired - Lifetime
-
2006
- 2006-10-23 IL IL178807A patent/IL178807A0/en unknown
- 2006-12-04 ZA ZA200610138A patent/ZA200610138B/en unknown
-
2009
- 2009-01-05 US US12/348,879 patent/US8153670B2/en not_active Expired - Fee Related
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- 2011-08-19 US US13/213,927 patent/US8377974B2/en not_active Expired - Fee Related
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