ES2389266T3 - Derivados de tioxantina y su uso como inhibidores de la mpo - Google Patents
Derivados de tioxantina y su uso como inhibidores de la mpo Download PDFInfo
- Publication number
- ES2389266T3 ES2389266T3 ES07748015T ES07748015T ES2389266T3 ES 2389266 T3 ES2389266 T3 ES 2389266T3 ES 07748015 T ES07748015 T ES 07748015T ES 07748015 T ES07748015 T ES 07748015T ES 2389266 T3 ES2389266 T3 ES 2389266T3
- Authority
- ES
- Spain
- Prior art keywords
- thioxo
- tetrahydro
- purin
- methyl
- amino
- 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.)
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- 239000003112 inhibitor Substances 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 303
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 176
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 153
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 132
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 120
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 102
- 150000002367 halogens Chemical class 0.000 claims abstract description 102
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 99
- 125000003118 aryl group Chemical group 0.000 claims abstract description 74
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 37
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000001301 oxygen Substances 0.000 claims abstract description 29
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
- 239000001257 hydrogen Substances 0.000 claims abstract description 26
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims abstract description 23
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims abstract description 23
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims abstract description 23
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 13
- 101100495923 Schizosaccharomyces pombe (strain 972 / ATCC 24843) chr2 gene Proteins 0.000 claims abstract description 10
- 201000006417 multiple sclerosis Diseases 0.000 claims description 153
- 229920006395 saturated elastomer Polymers 0.000 claims description 111
- 229910052757 nitrogen Inorganic materials 0.000 claims description 70
- 125000005842 heteroatom Chemical group 0.000 claims description 57
- 150000003839 salts Chemical class 0.000 claims description 55
- -1 1H-Benzimidazol-2-yl Chemical group 0.000 claims description 51
- 229910052799 carbon Inorganic materials 0.000 claims description 50
- 125000004429 atom Chemical group 0.000 claims description 41
- 125000002950 monocyclic group Chemical group 0.000 claims description 41
- 125000001424 substituent group Chemical group 0.000 claims description 34
- 238000011282 treatment Methods 0.000 claims description 29
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 27
- 201000010099 disease Diseases 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 17
- 239000003814 drug Substances 0.000 claims description 17
- 239000012453 solvate Substances 0.000 claims description 17
- 238000011321 prophylaxis Methods 0.000 claims description 15
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 14
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 13
- 201000001320 Atherosclerosis Diseases 0.000 claims description 10
- 208000018737 Parkinson disease Diseases 0.000 claims description 10
- 102100022631 Glutamate receptor ionotropic, NMDA 2C Human genes 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 108091008646 testicular receptors Proteins 0.000 claims description 9
- 102000004190 Enzymes Human genes 0.000 claims description 8
- 108090000790 Enzymes Proteins 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- NLEUINUWQPGXHI-UHFFFAOYSA-N 3-[(5-fluoro-1h-indol-2-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C=1C2=CC(F)=CC=C2NC=1CN(C(NC1=O)=S)C2=C1NC=N2 NLEUINUWQPGXHI-UHFFFAOYSA-N 0.000 claims description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 7
- 108091008648 NR7C Proteins 0.000 claims description 6
- 208000036110 Neuroinflammatory disease Diseases 0.000 claims description 6
- 239000002671 adjuvant Substances 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 208000015181 infectious disease Diseases 0.000 claims description 5
- 230000005764 inhibitory process Effects 0.000 claims description 5
- YVQCDZWXMRZDNJ-UHFFFAOYSA-N 3-(1h-benzimidazol-2-ylmethyl)-2-sulfanylidene-7h-purin-6-one Chemical compound C1=CC=C2NC(CN3C(=S)NC(C=4NC=NC=43)=O)=NC2=C1 YVQCDZWXMRZDNJ-UHFFFAOYSA-N 0.000 claims description 4
- IIIADLWTNVXNBD-UHFFFAOYSA-N 3-(2-aminopropyl)-2-sulfanylidene-7h-purin-6-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.O=C1NC(=S)N(CC(N)C)C2=C1NC=N2 IIIADLWTNVXNBD-UHFFFAOYSA-N 0.000 claims description 4
- XOQCUPGBGQMLQK-UHFFFAOYSA-N 3-(pyridin-2-ylmethyl)-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC1=CC=CC=N1 XOQCUPGBGQMLQK-UHFFFAOYSA-N 0.000 claims description 4
- AHKFFPZJELSEDV-UHFFFAOYSA-N 3-(pyridin-3-ylmethyl)-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC1=CC=CN=C1 AHKFFPZJELSEDV-UHFFFAOYSA-N 0.000 claims description 4
- UZWAFZKSLZCFRV-UHFFFAOYSA-N 3-(pyridin-4-ylmethyl)-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC1=CC=NC=C1 UZWAFZKSLZCFRV-UHFFFAOYSA-N 0.000 claims description 4
- AMZQGGBZPWAFRK-UHFFFAOYSA-N 3-(quinolin-4-ylmethyl)-2-sulfanylidene-7h-purin-6-one Chemical compound C1=CC=C2C(CN3C(=S)NC(C=4NC=NC=43)=O)=CC=NC2=C1 AMZQGGBZPWAFRK-UHFFFAOYSA-N 0.000 claims description 4
- SCYILAUVHGNMOS-UHFFFAOYSA-N 3-[(1-methylindol-2-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=CC=C2N(C)C(CN3C(NC(=O)C=4NC=NC=43)=S)=CC2=C1 SCYILAUVHGNMOS-UHFFFAOYSA-N 0.000 claims description 4
- WYPCJTAXRKLCNR-UHFFFAOYSA-N 3-[(2-butyl-4-chloro-1h-imidazol-5-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound N1C(CCCC)=NC(Cl)=C1CN1C(=S)NC(=O)C2=C1N=CN2 WYPCJTAXRKLCNR-UHFFFAOYSA-N 0.000 claims description 4
- ILPHIXRPMGQFJZ-UHFFFAOYSA-N 3-[(3,5-dimethyl-1,2-oxazol-4-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound CC1=NOC(C)=C1CN1C(=S)NC(=O)C2=C1N=CN2 ILPHIXRPMGQFJZ-UHFFFAOYSA-N 0.000 claims description 4
- HVYDXNSLQRFDIG-UHFFFAOYSA-N 3-[(3-butoxypyridin-2-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound CCCCOC1=CC=CN=C1CN1C(=S)NC(=O)C2=C1N=CN2 HVYDXNSLQRFDIG-UHFFFAOYSA-N 0.000 claims description 4
- GSEOEHAWXVFUCX-UHFFFAOYSA-N 3-[(3-propan-2-yl-1,2-oxazol-5-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound O1N=C(C(C)C)C=C1CN1C(=S)NC(=O)C2=C1N=CN2 GSEOEHAWXVFUCX-UHFFFAOYSA-N 0.000 claims description 4
- XXICVNQMYQJXLB-UHFFFAOYSA-N 3-[(4-butoxypyridin-2-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound CCCCOC1=CC=NC(CN2C(NC(=O)C=3NC=NC=32)=S)=C1 XXICVNQMYQJXLB-UHFFFAOYSA-N 0.000 claims description 4
- QQPMWNAWGBKGCU-UHFFFAOYSA-N 3-[(4-fluoro-1h-indol-3-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2C(F)=CC=CC=2NC=C1CN(C(NC1=O)=S)C2=C1NC=N2 QQPMWNAWGBKGCU-UHFFFAOYSA-N 0.000 claims description 4
- JUHNYHJKAXOZNQ-UHFFFAOYSA-N 3-[(4-methyl-1,2,5-oxadiazol-3-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound CC1=NON=C1CN1C(=S)NC(=O)C2=C1N=CN2 JUHNYHJKAXOZNQ-UHFFFAOYSA-N 0.000 claims description 4
- SXNNLWVBOSOYAT-UHFFFAOYSA-N 3-[(5-chloro-1h-indol-3-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C12=CC(Cl)=CC=C2NC=C1CN(C(NC1=O)=S)C2=C1NC=N2 SXNNLWVBOSOYAT-UHFFFAOYSA-N 0.000 claims description 4
- FCYBVAXJKFBGAG-UHFFFAOYSA-N 3-[(6-butoxypyridin-2-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound CCCCOC1=CC=CC(CN2C(NC(=O)C=3NC=NC=32)=S)=N1 FCYBVAXJKFBGAG-UHFFFAOYSA-N 0.000 claims description 4
- ZBDZGNKVUOCITH-UHFFFAOYSA-N 3-[(6-phenoxypyridin-3-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C=N1)=CC=C1OC1=CC=CC=C1 ZBDZGNKVUOCITH-UHFFFAOYSA-N 0.000 claims description 4
- BFIWTKIXULBUTE-UHFFFAOYSA-N 3-[1-(1h-benzimidazol-2-yl)ethyl]-2-sulfanylidene-7h-purin-6-one Chemical compound N=1C2=CC=CC=C2NC=1C(C)N(C(NC1=O)=S)C2=C1NC=N2 BFIWTKIXULBUTE-UHFFFAOYSA-N 0.000 claims description 4
- VPIIFTJWQLSYIL-UHFFFAOYSA-N 3-[2-(pyridin-2-ylmethoxy)propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)OCC1=CC=CC=N1 VPIIFTJWQLSYIL-UHFFFAOYSA-N 0.000 claims description 4
- FZDOSCHSMNDEKZ-UHFFFAOYSA-N 3-[2-(quinolin-4-ylmethylamino)ethyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=CC=C2C(CNCCN3C(=S)NC(C=4NC=NC=43)=O)=CC=NC2=C1 FZDOSCHSMNDEKZ-UHFFFAOYSA-N 0.000 claims description 4
- DSOXIQGGJIBKDX-UHFFFAOYSA-N 3-[2-[methyl(quinolin-4-ylmethyl)amino]ethyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=CC=C2C(CN(CCN3C(NC(=O)C=4NC=NC=43)=S)C)=CC=NC2=C1 DSOXIQGGJIBKDX-UHFFFAOYSA-N 0.000 claims description 4
- WEKREWHBVCUSJN-UHFFFAOYSA-N 3-[[3-ethoxy-4-(2-ethoxyethoxy)pyridin-2-yl]methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound CCOCCOC1=CC=NC(CN2C(NC(=O)C=3NC=NC=32)=S)=C1OCC WEKREWHBVCUSJN-UHFFFAOYSA-N 0.000 claims description 4
- 230000009286 beneficial effect Effects 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- HNUHQXANZGQWGQ-UHFFFAOYSA-N 2-sulfanylidene-3-[2-(2h-triazol-4-ylmethylamino)propyl]-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC1=CN=NN1 HNUHQXANZGQWGQ-UHFFFAOYSA-N 0.000 claims description 3
- WIOYFBDCQDDCTI-UHFFFAOYSA-N 2-sulfanylidene-3-[2-[[6-(trifluoromethyl)pyridin-3-yl]methylamino]propyl]-7h-purin-6-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC1=CC=C(C(F)(F)F)N=C1 WIOYFBDCQDDCTI-UHFFFAOYSA-N 0.000 claims description 3
- XPJXEVNLVLNQRN-UHFFFAOYSA-N 3-[2-(1h-benzimidazol-2-ylmethylamino)propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=CC=C2NC(CNC(CN3C(NC(=O)C=4NC=NC=43)=S)C)=NC2=C1 XPJXEVNLVLNQRN-UHFFFAOYSA-N 0.000 claims description 3
- VQQXXEBNSFHZEL-UHFFFAOYSA-N 3-[2-(1h-imidazol-2-ylmethylamino)propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC1=NC=CN1 VQQXXEBNSFHZEL-UHFFFAOYSA-N 0.000 claims description 3
- ATPOLLKTGMVGBH-UHFFFAOYSA-N 3-[2-(pyridin-2-ylmethylamino)propyl]-2-sulfanylidene-7h-purin-6-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC1=CC=CC=N1 ATPOLLKTGMVGBH-UHFFFAOYSA-N 0.000 claims description 3
- RRQORCIDUZXJPT-UHFFFAOYSA-N 3-[2-(pyridin-3-ylmethylamino)propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC1=CC=CN=C1 RRQORCIDUZXJPT-UHFFFAOYSA-N 0.000 claims description 3
- YMEBQHCQKRPKCI-UHFFFAOYSA-N 3-[2-(pyridin-4-ylmethylamino)propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC1=CC=NC=C1 YMEBQHCQKRPKCI-UHFFFAOYSA-N 0.000 claims description 3
- SKAUBHPJNDJLBF-UHFFFAOYSA-N 3-[2-(quinolin-2-ylmethylamino)propyl]-2-sulfanylidene-7h-purin-6-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC=CC2=NC(CNC(CN3C(NC(=O)C=4NC=NC=43)=S)C)=CC=C21 SKAUBHPJNDJLBF-UHFFFAOYSA-N 0.000 claims description 3
- DYKYDXGYDOPQCH-UHFFFAOYSA-N 3-[2-(quinolin-3-ylmethylamino)propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=CC=CC2=CC(CNC(CN3C(NC(=O)C=4NC=NC=43)=S)C)=CN=C21 DYKYDXGYDOPQCH-UHFFFAOYSA-N 0.000 claims description 3
- ZIDMKBGVDCBFNB-UHFFFAOYSA-N 3-[2-[(1-methylimidazol-2-yl)methylamino]propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC1=NC=CN1C ZIDMKBGVDCBFNB-UHFFFAOYSA-N 0.000 claims description 3
- CKBADCZMJZPWOE-UHFFFAOYSA-N 3-[2-[(1-methylindol-3-yl)methylamino]ethyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C12=CC=CC=C2N(C)C=C1CNCCN1C(=S)NC(=O)C2=C1N=CN2 CKBADCZMJZPWOE-UHFFFAOYSA-N 0.000 claims description 3
- RSEFPWXFDKRGNQ-UHFFFAOYSA-N 3-[2-[(1-methylindol-3-yl)methylamino]propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=CC=C2C(CNC(CN3C(NC(=O)C=4NC=NC=43)=S)C)=CN(C)C2=C1 RSEFPWXFDKRGNQ-UHFFFAOYSA-N 0.000 claims description 3
- HJJAUEDOGPHQPS-UHFFFAOYSA-N 3-[2-[(1-methylpyrrol-2-yl)methylamino]propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC1=CC=CN1C HJJAUEDOGPHQPS-UHFFFAOYSA-N 0.000 claims description 3
- CCNVCEPQJBXJJV-UHFFFAOYSA-N 3-[2-[(1-tert-butyl-3,5-dimethylpyrazol-4-yl)methylamino]propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC=1C(C)=NN(C(C)(C)C)C=1C CCNVCEPQJBXJJV-UHFFFAOYSA-N 0.000 claims description 3
- URTIWUIHHQAMGU-UHFFFAOYSA-N 3-[2-[(4,6-dichloropyrimidin-5-yl)methylamino]propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC1=C(Cl)N=CN=C1Cl URTIWUIHHQAMGU-UHFFFAOYSA-N 0.000 claims description 3
- NVMLJGAILCBLQF-UHFFFAOYSA-N 3-[2-[(6-bromo-2-methylimidazo[1,2-a]pyridin-3-yl)methylamino]propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=CC(Br)=CN2C(CNC(CN3C(NC(=O)C=4NC=NC=43)=S)C)=C(C)N=C21 NVMLJGAILCBLQF-UHFFFAOYSA-N 0.000 claims description 3
- ZIWMBSQQYYREIU-UHFFFAOYSA-N 3-[2-[(6-chloropyridin-3-yl)methylamino]propyl]-2-sulfanylidene-7h-purin-6-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC1=CC=C(Cl)N=C1 ZIWMBSQQYYREIU-UHFFFAOYSA-N 0.000 claims description 3
- ZXXFCLBHSMUNTJ-UHFFFAOYSA-N 3-[2-[[2,5-dimethyl-1-(1,3-thiazol-2-yl)pyrrol-3-yl]methylamino]propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC(=C1C)C=C(C)N1C1=NC=CS1 ZXXFCLBHSMUNTJ-UHFFFAOYSA-N 0.000 claims description 3
- KFZWPCHWGYQNRM-UHFFFAOYSA-N 3-[2-[[2-(dimethylamino)pyrimidin-5-yl]methylamino]propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC1=CN=C(N(C)C)N=C1 KFZWPCHWGYQNRM-UHFFFAOYSA-N 0.000 claims description 3
- RUYCBGLQUYCAEG-UHFFFAOYSA-N 3-[2-[[4-(3-chlorobenzoyl)-1-methylpyrrol-2-yl]methylamino]propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC(N(C=1)C)=CC=1C(=O)C1=CC=CC(Cl)=C1 RUYCBGLQUYCAEG-UHFFFAOYSA-N 0.000 claims description 3
- 206010014561 Emphysema Diseases 0.000 claims description 3
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- DSUIOKUNQXSQHF-UHFFFAOYSA-N n-[1-(6-oxo-2-sulfanylidene-7h-purin-3-yl)propan-2-yl]-1,8-naphthyridine-2-carboxamide Chemical compound C1=CC=NC2=NC(C(=O)NC(CN3C(NC(=O)C=4NC=NC=43)=S)C)=CC=C21 DSUIOKUNQXSQHF-UHFFFAOYSA-N 0.000 claims description 3
- FEBLFNYEUJEOLD-UHFFFAOYSA-N n-[1-(6-oxo-2-sulfanylidene-7h-purin-3-yl)propan-2-yl]-1h-imidazole-2-carboxamide Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NC(=O)C1=NC=CN1 FEBLFNYEUJEOLD-UHFFFAOYSA-N 0.000 claims description 3
- SMBFHTPOCAIXGA-UHFFFAOYSA-N n-[1-(6-oxo-2-sulfanylidene-7h-purin-3-yl)propan-2-yl]pyridine-2-carboxamide Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NC(=O)C1=CC=CC=N1 SMBFHTPOCAIXGA-UHFFFAOYSA-N 0.000 claims description 3
- GSLCARCSLQLGFD-UHFFFAOYSA-N n-[1-(6-oxo-2-sulfanylidene-7h-purin-3-yl)propan-2-yl]pyridine-3-carboxamide Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NC(=O)C1=CC=CN=C1 GSLCARCSLQLGFD-UHFFFAOYSA-N 0.000 claims description 3
- KIVNADZCPIUYGU-UHFFFAOYSA-N n-[1-(6-oxo-2-sulfanylidene-7h-purin-3-yl)propan-2-yl]pyridine-4-carboxamide Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NC(=O)C1=CC=NC=C1 KIVNADZCPIUYGU-UHFFFAOYSA-N 0.000 claims description 3
- KCYZTORODXQMMU-UHFFFAOYSA-N n-[1-(6-oxo-2-sulfanylidene-7h-purin-3-yl)propan-2-yl]pyrimidine-2-carboxamide Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NC(=O)C1=NC=CC=N1 KCYZTORODXQMMU-UHFFFAOYSA-N 0.000 claims description 3
- CVVVWYUXSNNDLD-UHFFFAOYSA-N n-[1-(6-oxo-2-sulfanylidene-7h-purin-3-yl)propan-2-yl]quinoline-2-carboxamide Chemical compound C1=CC=CC2=NC(C(=O)NC(CN3C(NC(=O)C=4NC=NC=43)=S)C)=CC=C21 CVVVWYUXSNNDLD-UHFFFAOYSA-N 0.000 claims description 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
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- 210000002435 tendon Anatomy 0.000 description 1
- JJXOIFHXNBFRNV-UHFFFAOYSA-N tert-butyl (2-methylpropan-2-yl)oxycarbonyl carbonate Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.CC(C)(C)OC(=O)OC(=O)OC(C)(C)C JJXOIFHXNBFRNV-UHFFFAOYSA-N 0.000 description 1
- PDAFIZPRSXHMCO-UHFFFAOYSA-N tert-butyl n-(1-hydroxypropan-2-yl)carbamate Chemical compound OCC(C)NC(=O)OC(C)(C)C PDAFIZPRSXHMCO-UHFFFAOYSA-N 0.000 description 1
- RFDSJHHLGFFVHD-UHFFFAOYSA-N tert-butyl n-(2-hydroxyethyl)-n-methylcarbamate Chemical compound OCCN(C)C(=O)OC(C)(C)C RFDSJHHLGFFVHD-UHFFFAOYSA-N 0.000 description 1
- ACNRTYKOPZDRCO-UHFFFAOYSA-N tert-butyl n-(2-oxoethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCC=O ACNRTYKOPZDRCO-UHFFFAOYSA-N 0.000 description 1
- CXGTZJYQWSUFET-IBGZPJMESA-N tesaglitazar Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OCCC1=CC=C(OS(C)(=O)=O)C=C1 CXGTZJYQWSUFET-IBGZPJMESA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 239000003868 thrombin inhibitor Substances 0.000 description 1
- 230000001732 thrombotic effect Effects 0.000 description 1
- PHWBOXQYWZNQIN-UHFFFAOYSA-N ticlopidine Chemical compound ClC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 PHWBOXQYWZNQIN-UHFFFAOYSA-N 0.000 description 1
- 229960005001 ticlopidine Drugs 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 241000701161 unidentified adenovirus Species 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 210000003934 vacuole Anatomy 0.000 description 1
- 230000003156 vasculitic effect Effects 0.000 description 1
- 208000001319 vasomotor rhinitis Diseases 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 229960001722 verapamil Drugs 0.000 description 1
- ZXIBCJHYVWYIKI-PZJWPPBQSA-N ximelagatran Chemical compound C1([C@@H](NCC(=O)OCC)C(=O)N2[C@@H](CC2)C(=O)NCC=2C=CC(=CC=2)C(\N)=N\O)CCCCC1 ZXIBCJHYVWYIKI-PZJWPPBQSA-N 0.000 description 1
- 229960001522 ximelagatran Drugs 0.000 description 1
- MWLSOWXNZPKENC-SSDOTTSWSA-N zileuton Chemical compound C1=CC=C2SC([C@H](N(O)C(N)=O)C)=CC2=C1 MWLSOWXNZPKENC-SSDOTTSWSA-N 0.000 description 1
- 229960005332 zileuton Drugs 0.000 description 1
Classifications
-
- 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
- C07D473/20—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
- A61K31/522—Purines, e.g. adenine having oxo groups directly attached to the heterocyclic ring, e.g. hypoxanthine, guanine, acyclovir
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- C07D473/22—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one sulfur atom
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pulmonology (AREA)
- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Immunology (AREA)
- Vascular Medicine (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Adhesives Or Adhesive Processes (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US79166706P | 2006-04-13 | 2006-04-13 | |
| US791667P | 2006-04-13 | ||
| PCT/SE2007/000349 WO2007120098A1 (en) | 2006-04-13 | 2007-04-12 | Thioxanthine derivatives and their use as inhibitors of mpo |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2389266T3 true ES2389266T3 (es) | 2012-10-24 |
Family
ID=38609780
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES07748015T Active ES2389266T3 (es) | 2006-04-13 | 2007-04-12 | Derivados de tioxantina y su uso como inhibidores de la mpo |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US8026244B2 (enExample) |
| EP (1) | EP2010535B1 (enExample) |
| JP (1) | JP2009533427A (enExample) |
| KR (2) | KR20080109087A (enExample) |
| CN (1) | CN101466712A (enExample) |
| AR (1) | AR060429A1 (enExample) |
| AU (1) | AU2007239147A1 (enExample) |
| BR (1) | BRPI0711529A2 (enExample) |
| CA (1) | CA2649150A1 (enExample) |
| CL (1) | CL2007001042A1 (enExample) |
| EC (1) | ECSP088821A (enExample) |
| ES (1) | ES2389266T3 (enExample) |
| MX (1) | MX2008013033A (enExample) |
| NO (1) | NO20084764L (enExample) |
| TW (1) | TW200806667A (enExample) |
| UY (1) | UY30267A1 (enExample) |
| WO (1) | WO2007120098A1 (enExample) |
| ZA (1) | ZA200808195B (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR039385A1 (es) * | 2002-04-19 | 2005-02-16 | Astrazeneca Ab | Derivados de tioxantina como inhibidores de la mieloperoxidasa |
| MY140748A (en) | 2004-12-06 | 2010-01-15 | Astrazeneca Ab | Novel pyrrolo [3,2-d] pyrimidin-4-one derivatives and their use in therapy |
| CN101472926A (zh) * | 2006-04-13 | 2009-07-01 | 阿斯利康(瑞典)有限公司 | 硫代黄嘌呤衍生物以及它们作为髓过氧化物酶抑制剂的用途 |
| TW200804383A (en) * | 2006-06-05 | 2008-01-16 | Astrazeneca Ab | New compounds |
| AR066936A1 (es) * | 2007-06-13 | 2009-09-23 | Astrazeneca Ab | 3 - (2r - tetrahidrofuril - metil) - 2 - tioxantina. composiciones farmaceuticas. |
| US20090053176A1 (en) * | 2007-08-23 | 2009-02-26 | Astrazeneca Ab | New Combination 937 |
| US20090054468A1 (en) * | 2007-08-23 | 2009-02-26 | Astrazeneca Ab | New Use 938 |
| WO2010068171A1 (en) * | 2008-12-12 | 2010-06-17 | Astrazeneca Ab | A process for the preparation of 3- [ (2r) tetrahydrofuran-2- ylmethyl] -2-thioxo-l, 2, 3, 7-tetrahydro-6h-purin-6-one |
| GB0913345D0 (en) | 2009-07-31 | 2009-09-16 | Astrazeneca Ab | New combination 802 |
| WO2011061527A1 (en) | 2009-11-17 | 2011-05-26 | Astrazeneca Ab | Combinations comprising a glucocorticoid receptor modulator for the treatment of respiratory diseases |
| GB201021992D0 (en) | 2010-12-23 | 2011-02-02 | Astrazeneca Ab | Compound |
| GB201021979D0 (en) | 2010-12-23 | 2011-02-02 | Astrazeneca Ab | New compound |
| AU2012335220B2 (en) | 2011-11-11 | 2017-06-01 | Pfizer Inc. | 2-thiopyrimidinones |
| US9422280B2 (en) * | 2012-03-29 | 2016-08-23 | Basf Se | N-substituted hetero-bicyclic compounds and derivatives for combating animal pests II |
| ES2688194T3 (es) * | 2014-09-11 | 2018-10-31 | Bristol-Myers Squibb Company | Inhibidores de mieloperoxidasa de triazolopirimidina y triazolopiridina de tioéter |
| US9616063B2 (en) | 2014-12-01 | 2017-04-11 | Astrazeneca Ab | 1-[2-(aminomethyl)benzyl]-2-thioxo-1,2,3,5-tetrahydro-4H-pyrrolo[3,2-d]pyrimidin-4-ones as inhibitors of myeloperoxidase |
| SG11201708407TA (en) | 2015-05-05 | 2017-11-29 | Pfizer | 2-thiopyrimidinones |
| US10316035B2 (en) | 2015-09-03 | 2019-06-11 | Bristol-Myers Squibb Company | Triazolopyridine inhibitors of myeloperoxidase |
| WO2017160632A1 (en) * | 2016-03-14 | 2017-09-21 | Bristol-Myers Squibb Company | Triazolopyridine inhibitors of myeloperoxidase |
| CN115403584B (zh) * | 2021-05-26 | 2024-04-02 | 长春金赛药业有限责任公司 | 2-硫代-2,3-二氢嘧啶-4-酮衍生物、药物组合物及其制备方法和应用 |
| KR102955719B1 (ko) * | 2022-02-23 | 2026-04-22 | 김병걸 | 금속도체에서 전기전도 성능을 향상시키는 금속 도전시트 |
| TW202426450A (zh) | 2022-08-18 | 2024-07-01 | 瑞典商阿斯特捷利康公司 | 髓過氧化物酶抑制劑 |
| CN120265633A (zh) * | 2022-12-09 | 2025-07-04 | 深圳信立泰药业股份有限公司 | 一种吡咯并[3,2-d]嘧啶-4-酮类衍生物及其制备方法和医药用途 |
| WO2025172474A1 (en) | 2024-02-15 | 2025-08-21 | Astrazeneca Ab | Inhibitors of myeloperoxidase |
| WO2025190901A1 (en) | 2024-03-13 | 2025-09-18 | Institut National de la Santé et de la Recherche Médicale | Use of myeloperoxidase (mpo) inhibitors for promoting cd8+ t cell responses |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9312853D0 (en) * | 1993-06-22 | 1993-08-04 | Euro Celtique Sa | Chemical compounds |
| US5773423A (en) * | 1993-07-13 | 1998-06-30 | The United States Of America As Represented By The Department Of Health And Human Services | A3 adenosine receptor agonists |
| US5708009A (en) * | 1993-12-21 | 1998-01-13 | Eli Lilly And Company | Methods of inhibiting myeloperoxidase activity |
| US6780865B1 (en) * | 1994-02-18 | 2004-08-24 | Cell Therapeutics, Inc. | Compounds having selective hydrolytic potentials |
| JPH10508032A (ja) * | 1994-12-13 | 1998-08-04 | ユーロ−セルティーク，エス．エイ． | アリールチオキサンチン類 |
| ES2264210T3 (es) * | 1997-09-05 | 2006-12-16 | Kyowa Hakko Kogyo Co., Ltd. | Derivados de xantina para el tratamiento de la isquemia cerebral. |
| EP1169321A4 (en) * | 1999-04-02 | 2002-10-30 | Euro Celtique Sa | PURINE DERIVATIVES WITH PHOSPHODIESTERASE INHIBITOR ACTIVITY |
| AR039385A1 (es) * | 2002-04-19 | 2005-02-16 | Astrazeneca Ab | Derivados de tioxantina como inhibidores de la mieloperoxidasa |
| SE0302756D0 (sv) * | 2003-10-17 | 2003-10-17 | Astrazeneca Ab | Novel Compounds |
| MY140748A (en) * | 2004-12-06 | 2010-01-15 | Astrazeneca Ab | Novel pyrrolo [3,2-d] pyrimidin-4-one derivatives and their use in therapy |
| CN101472926A (zh) * | 2006-04-13 | 2009-07-01 | 阿斯利康(瑞典)有限公司 | 硫代黄嘌呤衍生物以及它们作为髓过氧化物酶抑制剂的用途 |
| TW200804383A (en) * | 2006-06-05 | 2008-01-16 | Astrazeneca Ab | New compounds |
| US20090054468A1 (en) * | 2007-08-23 | 2009-02-26 | Astrazeneca Ab | New Use 938 |
-
2007
- 2007-04-10 UY UY30267A patent/UY30267A1/es unknown
- 2007-04-10 TW TW096112534A patent/TW200806667A/zh unknown
- 2007-04-12 CL CL200701042A patent/CL2007001042A1/es unknown
- 2007-04-12 US US12/295,306 patent/US8026244B2/en not_active Expired - Fee Related
- 2007-04-12 JP JP2009505326A patent/JP2009533427A/ja not_active Ceased
- 2007-04-12 CN CNA200780022184XA patent/CN101466712A/zh active Pending
- 2007-04-12 KR KR1020087027662A patent/KR20080109087A/ko not_active Withdrawn
- 2007-04-12 EP EP07748015A patent/EP2010535B1/en active Active
- 2007-04-12 WO PCT/SE2007/000349 patent/WO2007120098A1/en not_active Ceased
- 2007-04-12 AU AU2007239147A patent/AU2007239147A1/en not_active Abandoned
- 2007-04-12 CA CA002649150A patent/CA2649150A1/en not_active Abandoned
- 2007-04-12 AR ARP070101557A patent/AR060429A1/es unknown
- 2007-04-12 MX MX2008013033A patent/MX2008013033A/es not_active Application Discontinuation
- 2007-04-12 BR BRPI0711529-6A patent/BRPI0711529A2/pt not_active IP Right Cessation
- 2007-04-12 ES ES07748015T patent/ES2389266T3/es active Active
-
2008
- 2008-09-25 ZA ZA200808195A patent/ZA200808195B/xx unknown
- 2008-09-25 KR KR1020097014335A patent/KR20090109087A/ko not_active Ceased
- 2008-10-14 EC EC2008008821A patent/ECSP088821A/es unknown
- 2008-11-11 NO NO20084764A patent/NO20084764L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US8026244B2 (en) | 2011-09-27 |
| US20090149475A1 (en) | 2009-06-11 |
| ECSP088821A (es) | 2008-11-27 |
| CL2007001042A1 (es) | 2008-02-08 |
| CA2649150A1 (en) | 2007-10-25 |
| EP2010535A1 (en) | 2009-01-07 |
| UY30267A1 (es) | 2007-11-30 |
| KR20080109087A (ko) | 2008-12-16 |
| MX2008013033A (es) | 2008-10-17 |
| EP2010535A4 (en) | 2011-07-20 |
| AU2007239147A1 (en) | 2007-10-25 |
| CN101466712A (zh) | 2009-06-24 |
| AR060429A1 (es) | 2008-06-18 |
| KR20090109087A (ko) | 2009-10-19 |
| JP2009533427A (ja) | 2009-09-17 |
| ZA200808195B (en) | 2009-08-26 |
| TW200806667A (en) | 2008-02-01 |
| WO2007120098A1 (en) | 2007-10-25 |
| EP2010535B1 (en) | 2012-07-11 |
| BRPI0711529A2 (pt) | 2011-11-01 |
| NO20084764L (no) | 2009-01-06 |
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