HRP20120399T1 - Novi sulfonilpiroli kao inhibitori hdac - Google Patents

Novi sulfonilpiroli kao inhibitori hdac Download PDF

Info

Publication number: HRP20120399T1
Authority: HR; Croatia
Prior art keywords: acid; salt; cancer; compound according; inhibitors
Prior art date: 2005-09-21

Application number

HRP20120399TT

Other languages

English (en)

Croatian (hr)

Inventor

Maier Thomas

Beckers Thomas

Hummel Rolf-Peter

Feth Martin

Mller Matthias

B�r Thomas

Volz Jrgen

Original Assignee

4Sc Ag

Priority date (The priority date 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 date listed.)

2005-09-21

Filing date

2012-05-11

Publication date

2012-06-30

2012-05-11 Application filed by 4Sc Ag filed Critical 4Sc Ag

2012-06-30 Publication of HRP20120399T1 publication Critical patent/HRP20120399T1/hr

Links

239000003112 inhibitor Substances 0.000 title claims 3
JRZBWRPPYOMOJE-UHFFFAOYSA-N 2-sulfonylpyrrole Chemical class O=S(=O)=C1C=CC=N1 JRZBWRPPYOMOJE-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract 29
150000003839 salts Chemical class 0.000 claims abstract 23
239000002253 acid Substances 0.000 claims abstract 17
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims abstract 16
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims abstract 15
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract 12
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims abstract 12
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract 10
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims abstract 10
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims abstract 9
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims abstract 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract 8
-1 [2- (1H-indol-2-yl) ethyl] methylamino Chemical group 0.000 claims abstract 8
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims abstract 8
229940098779 methanesulfonic acid Drugs 0.000 claims abstract 8
FECGNJPYVFEKOD-VMPITWQZSA-N resminostat Chemical compound C1=CC(CN(C)C)=CC=C1S(=O)(=O)N1C=C(\C=C\C(=O)NO)C=C1 FECGNJPYVFEKOD-VMPITWQZSA-N 0.000 claims abstract 8
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims abstract 8
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims abstract 6
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims abstract 6
JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 claims abstract 6
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims abstract 6
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims abstract 6
229940092714 benzenesulfonic acid Drugs 0.000 claims abstract 6
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims abstract 6
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims abstract 6
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims abstract 6
KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 claims abstract 6
235000021314 Palmitic acid Nutrition 0.000 claims abstract 5
229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract 5
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims abstract 5
239000011976 maleic acid Substances 0.000 claims abstract 5
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims abstract 5
235000006408 oxalic acid Nutrition 0.000 claims abstract 5
239000011975 tartaric acid Substances 0.000 claims abstract 5
229960001367 tartaric acid Drugs 0.000 claims abstract 5
RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims abstract 4
WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 claims abstract 4
QCXJEYYXVJIFCE-UHFFFAOYSA-N 4-acetamidobenzoic acid Chemical compound CC(=O)NC1=CC=C(C(O)=O)C=C1 QCXJEYYXVJIFCE-UHFFFAOYSA-N 0.000 claims abstract 4
ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 claims abstract 4
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims abstract 4
QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 claims abstract 4
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims abstract 4
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims abstract 4
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims abstract 4
235000011054 acetic acid Nutrition 0.000 claims abstract 4
ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 claims abstract 4
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims abstract 4
JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims abstract 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract 4
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims abstract 4
235000015165 citric acid Nutrition 0.000 claims abstract 4
JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 claims abstract 4
239000001530 fumaric acid Substances 0.000 claims abstract 4
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 claims abstract 4
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims abstract 4
239000001630 malic acid Substances 0.000 claims abstract 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract 4
XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 claims abstract 4
PXQPEWDEAKTCGB-UHFFFAOYSA-N orotic acid Chemical compound OC(=O)C1=CC(=O)NC(=O)N1 PXQPEWDEAKTCGB-UHFFFAOYSA-N 0.000 claims abstract 4
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims abstract 4
229960004889 salicylic acid Drugs 0.000 claims abstract 4
ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims abstract 4
229930182843 D-Lactic acid Natural products 0.000 claims abstract 3
CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 claims abstract 3
JVTAAEKCZFNVCJ-UWTATZPHSA-N D-lactic acid Chemical compound C[C@@H](O)C(O)=O JVTAAEKCZFNVCJ-UWTATZPHSA-N 0.000 claims abstract 3
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical class NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims abstract 3
CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 claims abstract 3
239000002211 L-ascorbic acid Substances 0.000 claims abstract 3
235000000069 L-ascorbic acid Nutrition 0.000 claims abstract 3
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims abstract 3
239000005639 Lauric acid Substances 0.000 claims abstract 3
235000021355 Stearic acid Nutrition 0.000 claims abstract 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract 3
150000003863 ammonium salts Chemical class 0.000 claims abstract 3
229960005070 ascorbic acid Drugs 0.000 claims abstract 3
229960005261 aspartic acid Drugs 0.000 claims abstract 3
159000000007 calcium salts Chemical class 0.000 claims abstract 3
239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 claims abstract 3
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 claims abstract 3
229940022769 d- lactic acid Drugs 0.000 claims abstract 3
235000011087 fumaric acid Nutrition 0.000 claims abstract 3
239000004310 lactic acid Substances 0.000 claims abstract 3
235000014655 lactic acid Nutrition 0.000 claims abstract 3
159000000003 magnesium salts Chemical class 0.000 claims abstract 3
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims abstract 3
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims abstract 3
159000000000 sodium salts Chemical class 0.000 claims abstract 3
239000008117 stearic acid Substances 0.000 claims abstract 3
235000002906 tartaric acid Nutrition 0.000 claims abstract 3
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims abstract 2
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims abstract 2
BJEPYKJPYRNKOW-UWTATZPHSA-N (R)-malic acid Chemical compound OC(=O)[C@H](O)CC(O)=O BJEPYKJPYRNKOW-UWTATZPHSA-N 0.000 claims abstract 2
IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical compound OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-N 0.000 claims abstract 2
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims abstract 2
ZJYIRWSEDWBNAC-IZZDOVSWSA-N (e)-n-hydroxy-3-[1-(4-phenylphenyl)sulfonylpyrrol-3-yl]prop-2-enamide Chemical compound C1=C(/C=C/C(=O)NO)C=CN1S(=O)(=O)C1=CC=C(C=2C=CC=CC=2)C=C1 ZJYIRWSEDWBNAC-IZZDOVSWSA-N 0.000 claims abstract 2
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims abstract 2
LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 claims abstract 2
SJJCQDRGABAVBB-UHFFFAOYSA-N 1-hydroxy-2-naphthoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC=C21 SJJCQDRGABAVBB-UHFFFAOYSA-N 0.000 claims abstract 2
FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 claims abstract 2
YGTUPRIZNBMOFV-UHFFFAOYSA-N 2-(4-hydroxybenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=C(O)C=C1 YGTUPRIZNBMOFV-UHFFFAOYSA-N 0.000 claims abstract 2
WXHLLJAMBQLULT-UHFFFAOYSA-N 2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]-n-(2-methyl-6-sulfanylphenyl)-1,3-thiazole-5-carboxamide;hydrate Chemical compound O.C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1S WXHLLJAMBQLULT-UHFFFAOYSA-N 0.000 claims abstract 2
KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 claims abstract 2
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims abstract 2
ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 claims abstract 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims abstract 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract 2
WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 claims abstract 2
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims abstract 2
239000005711 Benzoic acid Substances 0.000 claims abstract 2
WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims abstract 2
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims abstract 2
RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims abstract 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims abstract 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract 2
239000005642 Oleic acid Substances 0.000 claims abstract 2
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims abstract 2
ODHCTXKNWHHXJC-GSVOUGTGSA-N Pyroglutamic acid Natural products OC(=O)[C@H]1CCC(=O)N1 ODHCTXKNWHHXJC-GSVOUGTGSA-N 0.000 claims abstract 2
239000001361 adipic acid Substances 0.000 claims abstract 2
235000011037 adipic acid Nutrition 0.000 claims abstract 2
229960000250 adipic acid Drugs 0.000 claims abstract 2
AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 claims abstract 2
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims abstract 2
229960004909 aminosalicylic acid Drugs 0.000 claims abstract 2
235000010233 benzoic acid Nutrition 0.000 claims abstract 2
LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 claims abstract 2
MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 claims abstract 2
KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 claims abstract 2
229930016911 cinnamic acid Natural products 0.000 claims abstract 2
235000013985 cinnamic acid Nutrition 0.000 claims abstract 2
AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 claims abstract 2
235000019253 formic acid Nutrition 0.000 claims abstract 2
229960005219 gentisic acid Drugs 0.000 claims abstract 2
235000012208 gluconic acid Nutrition 0.000 claims abstract 2
229950006191 gluconic acid Drugs 0.000 claims abstract 2
229960004275 glycolic acid Drugs 0.000 claims abstract 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims abstract 2
229940071870 hydroiodic acid Drugs 0.000 claims abstract 2
150000002505 iron Chemical class 0.000 claims abstract 2
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims abstract 2
FEWJPZIEWOKRBE-LWMBPPNESA-N levotartaric acid Chemical compound OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 claims abstract 2
229910003002 lithium salt Inorganic materials 0.000 claims abstract 2
159000000002 lithium salts Chemical class 0.000 claims abstract 2
235000011090 malic acid Nutrition 0.000 claims abstract 2
229960002510 mandelic acid Drugs 0.000 claims abstract 2
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims abstract 2
235000001968 nicotinic acid Nutrition 0.000 claims abstract 2
229960003512 nicotinic acid Drugs 0.000 claims abstract 2
239000011664 nicotinic acid Substances 0.000 claims abstract 2
229910017604 nitric acid Inorganic materials 0.000 claims abstract 2
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims abstract 2
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims abstract 2
229960002969 oleic acid Drugs 0.000 claims abstract 2
229960005010 orotic acid Drugs 0.000 claims abstract 2
WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 claims abstract 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims abstract 2
AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 claims abstract 2
229960002703 undecylenic acid Drugs 0.000 claims abstract 2
206010028980 Neoplasm Diseases 0.000 claims 24
201000011510 cancer Diseases 0.000 claims 17
239000002246 antineoplastic agent Substances 0.000 claims 12
239000000556 agonist Substances 0.000 claims 8
229940044601 receptor agonist Drugs 0.000 claims 8
239000000018 receptor agonist Substances 0.000 claims 8
208000017604 Hodgkin disease Diseases 0.000 claims 6
208000010747 Hodgkins lymphoma Diseases 0.000 claims 6
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FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 claims 1
FOCVUCIESVLUNU-UHFFFAOYSA-N Thiotepa Chemical compound C1CN1P(N1CC1)(=S)N1CC1 FOCVUCIESVLUNU-UHFFFAOYSA-N 0.000 claims 1
AEMOLEFTQBMNLQ-WAXACMCWSA-N alpha-D-glucuronic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-WAXACMCWSA-N 0.000 claims 1
230000001093 anti-cancer Effects 0.000 claims 1
230000006907 apoptotic process Effects 0.000 claims 1
229960004562 carboplatin Drugs 0.000 claims 1
229960004316 cisplatin Drugs 0.000 claims 1
DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 claims 1
229940127089 cytotoxic agent Drugs 0.000 claims 1
239000002552 dosage form Substances 0.000 claims 1
230000000694 effects Effects 0.000 claims 1
230000006882 induction of apoptosis Effects 0.000 claims 1
230000001939 inductive effect Effects 0.000 claims 1
230000005764 inhibitory process Effects 0.000 claims 1
108010085650 interferon gamma receptor Proteins 0.000 claims 1
230000003211 malignant effect Effects 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
DWAFYCQODLXJNR-BNTLRKBRSA-L oxaliplatin Chemical compound O1C(=O)C(=O)O[Pt]11N[C@@H]2CCCC[C@H]2N1 DWAFYCQODLXJNR-BNTLRKBRSA-L 0.000 claims 1
229960001756 oxaliplatin Drugs 0.000 claims 1
FPOHNWQLNRZRFC-ZHACJKMWSA-N panobinostat Chemical compound CC=1NC2=CC=CC=C2C=1CCNCC1=CC=C(\C=C\C(=O)NO)C=C1 FPOHNWQLNRZRFC-ZHACJKMWSA-N 0.000 claims 1
239000008024 pharmaceutical diluent Substances 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 1
229910052697 platinum Inorganic materials 0.000 claims 1
235000019260 propionic acid Nutrition 0.000 claims 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
190014017285 satraplatin Chemical compound 0.000 claims 1
229960005399 satraplatin Drugs 0.000 claims 1
239000007787 solid Substances 0.000 claims 1
230000001225 therapeutic effect Effects 0.000 claims 1
229960001196 thiotepa Drugs 0.000 claims 1
OXVFTQXFQKQMMO-RFHAIHRQSA-N (2S)-2-aminopentanedioic acid (2S,3S,4S,5R)-2,3,4,5-tetrahydroxy-6-oxohexanoic acid Chemical compound N[C@@H](CCC(=O)O)C(=O)O.O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(=O)O OXVFTQXFQKQMMO-RFHAIHRQSA-N 0.000 abstract 1
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 abstract 1
IMGGXPQCECGGRU-UHFFFAOYSA-N decanoic acid;propanoic acid Chemical compound CCC(O)=O.CCCCCCCCCC(O)=O IMGGXPQCECGGRU-UHFFFAOYSA-N 0.000 abstract 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 abstract 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
- C07D207/48—Sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
- 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
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/4015—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil having oxo groups directly attached to the heterocyclic ring, e.g. piracetam, ethosuximide
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Epidemiology (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Oncology (AREA)
Hematology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Steroid Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Pyrrole Compounds (AREA)

HRP20120399TT 2005-09-21 2012-05-11 Novi sulfonilpiroli kao inhibitori hdac HRP20120399T1 (hr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP05108728		2005-09-21
PCT/EP2006/066197 WO2007039404A1 (fr)	2005-09-21	2006-09-08	Utilisation de nouveaux sulphonylpyrroles comme inhibiteurs des hdac

Publications (1)

Publication Number	Publication Date
HRP20120399T1 true HRP20120399T1 (hr)	2012-06-30

Family

ID=37035343

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HRP20120399TT HRP20120399T1 (hr)	2005-09-21	2012-05-11	Novi sulfonilpiroli kao inhibitori hdac

Country Status (26)

Country	Link
US (1)	US8232297B2 (fr)
EP (1)	EP1928872B1 (fr)
JP (1)	JP5305910B2 (fr)
KR (1)	KR101256846B1 (fr)
CN (1)	CN101268070B (fr)
AR (1)	AR057824A1 (fr)
AT (1)	ATE549333T1 (fr)
AU (1)	AU2006298882B2 (fr)
BR (1)	BRPI0617167B8 (fr)
CA (1)	CA2622673C (fr)
CY (1)	CY1112780T1 (fr)
DK (1)	DK1928872T3 (fr)
EA (1)	EA016345B1 (fr)
ES (1)	ES2381962T3 (fr)
HK (1)	HK1124320A1 (fr)
HR (1)	HRP20120399T1 (fr)
IL (1)	IL189782A (fr)
NO (1)	NO341744B1 (fr)
NZ (1)	NZ566074A (fr)
PL (1)	PL1928872T3 (fr)
PT (1)	PT1928872E (fr)
RS (1)	RS52383B (fr)
SI (1)	SI1928872T1 (fr)
TW (1)	TWI406846B (fr)
WO (1)	WO2007039404A1 (fr)
ZA (1)	ZA200801394B (fr)

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SI1928872T1 (sl)	2005-09-21	2012-06-29	4Sc Ag	Novi sulfonilpiroli kot inhibitorji HDAC
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EP2100882A1 (fr) *	2008-03-12	2009-09-16	4Sc Ag	Sels d'acrylamide (E) -N -(2-Amino-phényl) -3-{1-[4-(1-méthyl-1H-pyrazol-4-yl)-benzènesulfonyl] -1H-pyrrol-3-yl}
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KR102181365B1 (ko) *	2012-08-06	2020-11-23	에이시아 바이오사이언시스 인코포레이티드.	단백질 키나아제 억제제로서 새로운 피롤로피리미딘 화합물
WO2014143666A1 (fr)	2013-03-15	2014-09-18	Biomarin Pharmaceutical Inc.	Inhibiteurs de hdac
SG11201600062RA (en)	2013-07-11	2016-02-26	Acea Biosciences Inc	Pyrimidine derivatives as kinase inhibitors
RU2018115334A (ru)	2015-10-09	2019-11-11	Ацея Терапьютикс, Инк.	Фармацевтические соли, физические формы и композиции пирролопиримидиновых ингибиторов киназ, и способы их получения
CN105622680B (zh) *	2015-12-22	2018-01-19	杭州卢普生物科技有限公司	一种舒尼替尼衍生物及其制备方法和应用
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SI1928872T1 (sl)	2005-09-21	2012-06-29	4Sc Ag	Novi sulfonilpiroli kot inhibitorji HDAC

2006
- 2006-09-08 SI SI200631335T patent/SI1928872T1/sl unknown
- 2006-09-08 RS RS20120248A patent/RS52383B/en unknown
- 2006-09-08 US US11/992,015 patent/US8232297B2/en active Active
- 2006-09-08 CA CA2622673A patent/CA2622673C/fr active Active
- 2006-09-08 ES ES06793379T patent/ES2381962T3/es active Active
- 2006-09-08 WO PCT/EP2006/066197 patent/WO2007039404A1/fr active Application Filing
- 2006-09-08 EA EA200800700A patent/EA016345B1/ru not_active IP Right Cessation
- 2006-09-08 DK DK06793379.6T patent/DK1928872T3/da active
- 2006-09-08 PL PL06793379T patent/PL1928872T3/pl unknown
- 2006-09-08 AT AT06793379T patent/ATE549333T1/de active
- 2006-09-08 KR KR1020087008938A patent/KR101256846B1/ko active IP Right Grant
- 2006-09-08 CN CN2006800347491A patent/CN101268070B/zh active Active
- 2006-09-08 PT PT06793379T patent/PT1928872E/pt unknown
- 2006-09-08 BR BRPI0617167A patent/BRPI0617167B8/pt active IP Right Grant
- 2006-09-08 EP EP06793379A patent/EP1928872B1/fr active Active
- 2006-09-08 AU AU2006298882A patent/AU2006298882B2/en active Active
- 2006-09-08 JP JP2008530492A patent/JP5305910B2/ja active Active
- 2006-09-08 NZ NZ566074A patent/NZ566074A/en unknown
- 2006-09-21 AR ARP060104135A patent/AR057824A1/es active IP Right Grant
- 2006-09-21 TW TW095135005A patent/TWI406846B/zh active
2008
- 2008-02-11 ZA ZA2008/01394A patent/ZA200801394B/en unknown
- 2008-02-26 IL IL189782A patent/IL189782A/en active IP Right Grant
- 2008-04-14 NO NO20081797A patent/NO341744B1/no unknown
2009
- 2009-02-19 HK HK09101602.9A patent/HK1124320A1/xx unknown
2012
- 2012-05-11 HR HRP20120399TT patent/HRP20120399T1/hr unknown
- 2012-05-21 CY CY20121100465T patent/CY1112780T1/el unknown

Also Published As

Publication number	Publication date
TW200745028A (en)	2007-12-16
RS52383B (en)	2012-12-31
DK1928872T3 (da)	2012-05-07
AU2006298882B2 (en)	2011-10-27
US8232297B2 (en)	2012-07-31
PT1928872E (pt)	2012-05-25
EA016345B1 (ru)	2012-04-30
NO341744B1 (no)	2018-01-15
CA2622673A1 (fr)	2007-04-12
KR101256846B1 (ko)	2013-04-24
IL189782A (en)	2013-06-27
TWI406846B (zh)	2013-09-01
EA200800700A1 (ru)	2009-04-28
HK1124320A1 (en)	2009-07-10
US20090263353A1 (en)	2009-10-22
BRPI0617167A2 (pt)	2011-07-12
KR20080047607A (ko)	2008-05-29
NO20081797L (no)	2008-04-17
ZA200801394B (en)	2009-12-30
CY1112780T1 (el)	2016-02-10
BRPI0617167B8 (pt)	2021-05-25
SI1928872T1 (sl)	2012-06-29
ATE549333T1 (de)	2012-03-15
WO2007039404A1 (fr)	2007-04-12
EP1928872B1 (fr)	2012-03-14
NZ566074A (en)	2011-08-26
CA2622673C (fr)	2017-06-27
EP1928872A1 (fr)	2008-06-11
IL189782A0 (en)	2008-08-07
AU2006298882A1 (en)	2007-04-12
CN101268070B (zh)	2012-09-05
JP2009508826A (ja)	2009-03-05
CN101268070A (zh)	2008-09-17
PL1928872T3 (pl)	2012-08-31
AR057824A1 (es)	2007-12-19
JP5305910B2 (ja)	2013-10-02
BRPI0617167B1 (pt)	2021-02-09
ES2381962T3 (es)	2012-06-04

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