UA80572C2 - THIAZOLIDINE DERIVATIVES AS hYAK3 INHIBITORS - Google Patents

THIAZOLIDINE DERIVATIVES AS hYAK3 INHIBITORS Download PDF

Info

Publication number: UA80572C2
Authority: UA; Ukraine
Prior art keywords: ylmethylene; thiazolidin; thiazol; dihydrobenzofuran; quinolin
Prior art date: 2002-11-22

Application number

UAA200504788A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Smithkline Beecham Corp

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.)

2002-11-22

Filing date

2003-11-18

Publication date

2007-10-10

2003-11-18 Application filed by Smithkline Beecham Corp filed Critical Smithkline Beecham Corp

2007-10-10 Publication of UA80572C2 publication Critical patent/UA80572C2/uk

Links

239000003112 inhibitor Substances 0.000 title description 4
OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical class C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 104
238000000034 method Methods 0.000 claims abstract description 37
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 13
230000000694 effects Effects 0.000 claims abstract description 11
201000010099 disease Diseases 0.000 claims abstract description 10
230000002401 inhibitory effect Effects 0.000 claims abstract description 3
125000000217 alkyl group Chemical group 0.000 claims description 67
NOLHRFLIXVQPSZ-UHFFFAOYSA-N 1,3-thiazolidin-4-one Chemical compound O=C1CSCN1 NOLHRFLIXVQPSZ-UHFFFAOYSA-N 0.000 claims description 50
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 45
229910052736 halogen Inorganic materials 0.000 claims description 37
150000002367 halogens Chemical class 0.000 claims description 37
229910052739 hydrogen Inorganic materials 0.000 claims description 34
239000001257 hydrogen Substances 0.000 claims description 33
150000002431 hydrogen Chemical class 0.000 claims description 33
208000007502 anemia Diseases 0.000 claims description 29
150000003839 salts Chemical class 0.000 claims description 29
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 27
-1 MH" Chemical class 0.000 claims description 20
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
239000012453 solvate Substances 0.000 claims description 19
RBYSUZKKJAVNEO-UHFFFAOYSA-N 2-(2-methylanilino)-5-(quinolin-6-ylmethylidene)-1,3-thiazol-4-one Chemical compound CC1=CC=CC=C1N=C(NC1=O)SC1=CC1=CC=C(N=CC=C2)C2=C1 RBYSUZKKJAVNEO-UHFFFAOYSA-N 0.000 claims description 13
239000005711 Benzoic acid Substances 0.000 claims description 13
235000010233 benzoic acid Nutrition 0.000 claims description 13
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
241000124008 Mammalia Species 0.000 claims description 11
239000008194 pharmaceutical composition Substances 0.000 claims description 11
239000003085 diluting agent Substances 0.000 claims description 10
239000000546 pharmaceutical excipient Substances 0.000 claims description 10
239000003937 drug carrier Substances 0.000 claims description 9
230000000925 erythroid effect Effects 0.000 claims description 9
206010065553 Bone marrow failure Diseases 0.000 claims description 8
201000003793 Myelodysplastic syndrome Diseases 0.000 claims description 8
210000000777 hematopoietic system Anatomy 0.000 claims description 8
208000032467 Aplastic anaemia Diseases 0.000 claims description 7
206010033661 Pancytopenia Diseases 0.000 claims description 7
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
208000024389 cytopenia Diseases 0.000 claims description 7
230000006806 disease prevention Effects 0.000 claims description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
125000001624 naphthyl group Chemical group 0.000 claims description 6
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
OVHGJDOCDAMKTG-UHFFFAOYSA-N 2-(2-methylsulfanylanilino)-5-(quinolin-6-ylmethylidene)-1,3-thiazol-4-one Chemical compound CSC1=CC=CC=C1N=C(NC1=O)SC1=CC1=CC=C(N=CC=C2)C2=C1 OVHGJDOCDAMKTG-UHFFFAOYSA-N 0.000 claims description 5
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 5
235000013305 food Nutrition 0.000 claims description 5
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
RBMYZLOAIMVAJF-UHFFFAOYSA-N 2-(2,6-dichloroanilino)-5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-1,3-thiazol-4-one Chemical compound ClC1=CC=CC(Cl)=C1N=C(NC1=O)SC1=CC1=CC=C(OCC2)C2=C1 RBMYZLOAIMVAJF-UHFFFAOYSA-N 0.000 claims description 3
NOABIVVHZKOQLR-UHFFFAOYSA-N 2-(2,6-dichloroanilino)-5-(quinolin-6-ylmethylidene)-1,3-thiazol-4-one Chemical compound ClC1=CC=CC(Cl)=C1NC(S1)=NC(=O)C1=CC1=CC=C(N=CC=C2)C2=C1 NOABIVVHZKOQLR-UHFFFAOYSA-N 0.000 claims description 3
VIXVBMOJVIWSHX-UHFFFAOYSA-N 2-(2,6-dichloroanilino)-5-[(3-fluoro-4-hydroxyphenyl)methylidene]-1,3-thiazol-4-one Chemical compound C1=C(F)C(O)=CC=C1C=C(S1)C(=O)NC1=NC1=C(Cl)C=CC=C1Cl VIXVBMOJVIWSHX-UHFFFAOYSA-N 0.000 claims description 3
CJXKRXBAWWCSQH-UHFFFAOYSA-N 2-(2-bromoanilino)-5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-1,3-thiazol-4-one Chemical compound BrC1=CC=CC=C1N=C(NC1=O)SC1=CC1=CC=C(OCC2)C2=C1 CJXKRXBAWWCSQH-UHFFFAOYSA-N 0.000 claims description 3
PIOZRFOSBSXDQS-UHFFFAOYSA-N 2-(2-bromoanilino)-5-[(3,4-diaminophenyl)methylidene]-1,3-thiazol-4-one Chemical compound C1=C(N)C(N)=CC=C1C=C1C(=O)N=C(NC=2C(=CC=CC=2)Br)S1 PIOZRFOSBSXDQS-UHFFFAOYSA-N 0.000 claims description 3
SXQCFGHYESQTLV-UHFFFAOYSA-N 2-(2-bromoanilino)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-1,3-thiazol-4-one Chemical compound C1=C(O)C(OC)=CC(C=C2C(N=C(NC=3C(=CC=CC=3)Br)S2)=O)=C1 SXQCFGHYESQTLV-UHFFFAOYSA-N 0.000 claims description 3
TVCRMIHVSUPCBA-UHFFFAOYSA-N 2-(2-bromoanilino)-5-[(5-pyridin-2-ylthiophen-2-yl)methylidene]-1,3-thiazol-4-one Chemical compound BrC1=CC=CC=C1NC(S1)=NC(=O)C1=CC1=CC=C(C=2N=CC=CC=2)S1 TVCRMIHVSUPCBA-UHFFFAOYSA-N 0.000 claims description 3
CGVLXUZVJUCVMN-UHFFFAOYSA-N 2-(2-chloro-4-fluoro-5-methylanilino)-5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-1,3-thiazol-4-one Chemical compound C1=C(F)C(C)=CC(N=C2SC(C(=O)N2)=CC=2C=C3CCOC3=CC=2)=C1Cl CGVLXUZVJUCVMN-UHFFFAOYSA-N 0.000 claims description 3
GWOKZFNBGFQXEJ-UHFFFAOYSA-N 2-(2-chloro-5-fluoroanilino)-5-(quinolin-6-ylmethylidene)-1,3-thiazol-4-one Chemical compound FC1=CC=C(Cl)C(N=C2SC(C(=O)N2)=CC=2C=C3C=CC=NC3=CC=2)=C1 GWOKZFNBGFQXEJ-UHFFFAOYSA-N 0.000 claims description 3
KCNYITTZCXIVRV-UHFFFAOYSA-N 2-(2-chloroanilino)-5-[(3-fluoro-4-hydroxyphenyl)methylidene]-1,3-thiazol-4-one Chemical compound C1=C(F)C(O)=CC=C1C=C(S1)C(=O)NC1=NC1=CC=CC=C1Cl KCNYITTZCXIVRV-UHFFFAOYSA-N 0.000 claims description 3
OVZIDDOBFQWANM-UHFFFAOYSA-N 2-(2-chloroanilino)-5-[(3-fluoro-4-methoxyphenyl)methylidene]-1,3-thiazol-4-one Chemical compound C1=C(F)C(OC)=CC=C1C=C(S1)C(=O)NC1=NC1=CC=CC=C1Cl OVZIDDOBFQWANM-UHFFFAOYSA-N 0.000 claims description 3
CEYSJUACBKYCKN-UHFFFAOYSA-N 2-(2-chloroanilino)-5-[(4-hydroxy-3-methoxyphenyl)methylidene]-4-thiazolone Chemical compound C1=C(O)C(OC)=CC(C=C2C(N=C(NC=3C(=CC=CC=3)Cl)S2)=O)=C1 CEYSJUACBKYCKN-UHFFFAOYSA-N 0.000 claims description 3
ZRYHAXCSONNMSH-UHFFFAOYSA-N 2-(2-chloroanilino)-5-[(4-hydroxyphenyl)methylidene]-1,3-thiazol-4-one Chemical compound C1=CC(O)=CC=C1C=C1C(=O)N=C(NC=2C(=CC=CC=2)Cl)S1 ZRYHAXCSONNMSH-UHFFFAOYSA-N 0.000 claims description 3
HROXESYKDDDRDE-UHFFFAOYSA-N 2-(2-chloroanilino)-5-[(4-methoxyphenyl)methylidene]-1,3-thiazol-4-one Chemical compound C1=CC(OC)=CC=C1C=C1C(=O)N=C(NC=2C(=CC=CC=2)Cl)S1 HROXESYKDDDRDE-UHFFFAOYSA-N 0.000 claims description 3
OLUCGVIJCPYPMP-UHFFFAOYSA-N 2-(2-methoxyanilino)-5-(quinolin-6-ylmethylidene)-1,3-thiazol-4-one Chemical compound COC1=CC=CC=C1N=C(NC1=O)SC1=CC1=CC=C(N=CC=C2)C2=C1 OLUCGVIJCPYPMP-UHFFFAOYSA-N 0.000 claims description 3
OJSNJDIKPXJLER-UHFFFAOYSA-N 2-(benzylamino)-5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-1,3-thiazol-4-one Chemical compound S1C(=CC=2C=C3CCOC3=CC=2)C(=O)N=C1NCC1=CC=CC=C1 OJSNJDIKPXJLER-UHFFFAOYSA-N 0.000 claims description 3
YMMCZMKMBHMOCP-UHFFFAOYSA-N 2-(cyclohexylamino)-5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-1,3-thiazol-4-one Chemical compound S1C(=CC=2C=C3CCOC3=CC=2)C(=O)NC1=NC1CCCCC1 YMMCZMKMBHMOCP-UHFFFAOYSA-N 0.000 claims description 3
YBXFNZSFYCNPEU-UHFFFAOYSA-N 2-[(4-tert-butyl-1,3-thiazol-2-yl)amino]-5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-1,3-thiazol-4-one Chemical compound CC(C)(C)C1=CSC(NC=2SC(C(=O)N=2)=CC=2C=C3CCOC3=CC=2)=N1 YBXFNZSFYCNPEU-UHFFFAOYSA-N 0.000 claims description 3
NZZJGWOUWVLUTP-UHFFFAOYSA-N 2-[2-chloro-4-(trifluoromethyl)anilino]-5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-1,3-thiazol-4-one Chemical compound ClC1=CC(C(F)(F)F)=CC=C1N=C(NC1=O)SC1=CC1=CC=C(OCC2)C2=C1 NZZJGWOUWVLUTP-UHFFFAOYSA-N 0.000 claims description 3
GYOFCYHSKUCRQZ-UHFFFAOYSA-N 5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-2-(2,4,6-trimethylanilino)-1,3-thiazol-4-one Chemical compound CC1=CC(C)=CC(C)=C1N=C(NC1=O)SC1=CC1=CC=C(OCC2)C2=C1 GYOFCYHSKUCRQZ-UHFFFAOYSA-N 0.000 claims description 3
YCAQTHIDBNIVRV-UHFFFAOYSA-N 5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-2-(2-fluoroanilino)-1,3-thiazol-4-one Chemical compound FC1=CC=CC=C1N=C(NC1=O)SC1=CC1=CC=C(OCC2)C2=C1 YCAQTHIDBNIVRV-UHFFFAOYSA-N 0.000 claims description 3
VYNWEIBKZBBVJX-UHFFFAOYSA-N 5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-2-(2-methylanilino)-1,3-thiazol-4-one Chemical compound CC1=CC=CC=C1N=C(NC1=O)SC1=CC1=CC=C(OCC2)C2=C1 VYNWEIBKZBBVJX-UHFFFAOYSA-N 0.000 claims description 3
WEYQVIXVEQEUIU-UHFFFAOYSA-N 5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-2-(2-methylsulfanylanilino)-1,3-thiazol-4-one Chemical compound CSC1=CC=CC=C1N=C(NC1=O)SC1=CC1=CC=C(OCC2)C2=C1 WEYQVIXVEQEUIU-UHFFFAOYSA-N 0.000 claims description 3
AWLUKGDKBKLSAP-UHFFFAOYSA-N 5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-2-(2-nitroanilino)-1,3-thiazol-4-one Chemical compound [O-][N+](=O)C1=CC=CC=C1N=C(NC1=O)SC1=CC1=CC=C(OCC2)C2=C1 AWLUKGDKBKLSAP-UHFFFAOYSA-N 0.000 claims description 3
AQBZPOMLIXGKMH-UHFFFAOYSA-N 5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-2-(piperidin-1-ylamino)-1,3-thiazol-4-one Chemical compound S1C(=CC=2C=C3CCOC3=CC=2)C(=O)N=C1NN1CCCCC1 AQBZPOMLIXGKMH-UHFFFAOYSA-N 0.000 claims description 3
IAYSASOKGMRVCF-UHFFFAOYSA-N 5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-2-[2-(dimethylamino)ethylamino]-1,3-thiazol-4-one Chemical compound S1C(NCCN(C)C)=NC(=O)C1=CC1=CC=C(OCC2)C2=C1 IAYSASOKGMRVCF-UHFFFAOYSA-N 0.000 claims description 3
IXIZMBMCSXPLMU-UHFFFAOYSA-N 5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-2-[3-(dimethylamino)propylamino]-1,3-thiazol-4-one Chemical compound S1C(NCCCN(C)C)=NC(=O)C1=CC1=CC=C(OCC2)C2=C1 IXIZMBMCSXPLMU-UHFFFAOYSA-N 0.000 claims description 3
PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 claims description 3
SRDGYKQKWIQUGB-UHFFFAOYSA-N 2-(2,6-dichloroanilino)-5-[(2-methoxypyridin-3-yl)methylidene]-1,3-thiazol-4-one Chemical compound COC1=NC=CC=C1C=C1C(=O)N=C(NC=2C(=CC=CC=2Cl)Cl)S1 SRDGYKQKWIQUGB-UHFFFAOYSA-N 0.000 claims description 2
AZRXSULNBSVQHE-UHFFFAOYSA-N 2-(2-chloroanilino)-5-[(3-chloro-4-hydroxyphenyl)methylidene]-1,3-thiazol-4-one Chemical compound C1=C(Cl)C(O)=CC=C1C=C(S1)C(=O)NC1=NC1=CC=CC=C1Cl AZRXSULNBSVQHE-UHFFFAOYSA-N 0.000 claims description 2
PTIYTUSMMOTQIO-UHFFFAOYSA-N 2-(2-chloroanilino)-5-[(4-hydroxy-2-methoxyphenyl)methylidene]-1,3-thiazol-4-one Chemical compound COC1=CC(O)=CC=C1C=C(S1)C(=O)NC1=NC1=CC=CC=C1Cl PTIYTUSMMOTQIO-UHFFFAOYSA-N 0.000 claims description 2
UKBZERKCSICJCY-UHFFFAOYSA-N 5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-2-(2-methylsulfinylanilino)-1,3-thiazol-4-one Chemical compound CS(=O)C1=CC=CC=C1N=C(NC1=O)SC1=CC1=CC=C(OCC2)C2=C1 UKBZERKCSICJCY-UHFFFAOYSA-N 0.000 claims description 2
BLTWRBXFEIHSMD-UHFFFAOYSA-N 5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-2-[2-(trifluoromethyl)anilino]-1,3-thiazol-4-one Chemical compound FC(F)(F)C1=CC=CC=C1N=C(NC1=O)SC1=CC1=CC=C(OCC2)C2=C1 BLTWRBXFEIHSMD-UHFFFAOYSA-N 0.000 claims description 2
239000000969 carrier Substances 0.000 claims description 2
150000004702 methyl esters Chemical class 0.000 claims description 2
SHXHWOPEFBMMKJ-ZSOIEALJSA-N (5z)-2-(2-chloroanilino)-5-[(4-hydroxy-3-nitrophenyl)methylidene]-1,3-thiazol-4-one Chemical compound C1=C([N+]([O-])=O)C(O)=CC=C1\C=C/1C(=O)N=C(NC=2C(=CC=CC=2)Cl)S\1 SHXHWOPEFBMMKJ-ZSOIEALJSA-N 0.000 claims 2
KYODTXADECRZKW-UHFFFAOYSA-N 1-methylidene-1,3-thiazol-4-one Chemical compound C=S1C=NC(C1)=O KYODTXADECRZKW-UHFFFAOYSA-N 0.000 claims 2
VJAHLUZNTNLKQU-UHFFFAOYSA-N 2-(2-chloro-4-fluoro-5-methylanilino)-5-(quinolin-6-ylmethylidene)-1,3-thiazol-4-one Chemical compound C1=C(F)C(C)=CC(N=C2SC(C(=O)N2)=CC=2C=C3C=CC=NC3=CC=2)=C1Cl VJAHLUZNTNLKQU-UHFFFAOYSA-N 0.000 claims 2
YOXHGYVOEADWIF-UHFFFAOYSA-N 2-(2-chloro-5-fluoroanilino)-5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-1,3-thiazol-4-one Chemical compound FC1=CC=C(Cl)C(N=C2SC(C(=O)N2)=CC=2C=C3CCOC3=CC=2)=C1 YOXHGYVOEADWIF-UHFFFAOYSA-N 0.000 claims 2
YJSBQIJOLWMMHY-UHFFFAOYSA-N 2-(2-chloro-5-fluoroanilino)-5-[(3-fluoro-4-hydroxyphenyl)methylidene]-1,3-thiazol-4-one Chemical compound C1=C(F)C(O)=CC=C1C=C(S1)C(=O)NC1=NC1=CC(F)=CC=C1Cl YJSBQIJOLWMMHY-UHFFFAOYSA-N 0.000 claims 2
KBHLLKVBFLXVNP-UHFFFAOYSA-N 2-(4-bromo-2-chloroanilino)-5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-1,3-thiazol-4-one Chemical compound ClC1=CC(Br)=CC=C1N=C(NC1=O)SC1=CC1=CC=C(OCC2)C2=C1 KBHLLKVBFLXVNP-UHFFFAOYSA-N 0.000 claims 2
IIHXDPRLFRZEQG-UHFFFAOYSA-N 5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-2-(2-methoxyanilino)-1,3-thiazol-4-one Chemical compound COC1=CC=CC=C1NC(S1)=NC(=O)C1=CC1=CC=C(OCC2)C2=C1 IIHXDPRLFRZEQG-UHFFFAOYSA-N 0.000 claims 2
NYSIWPJIULZPCZ-UHFFFAOYSA-N 5-(2,3-dihydro-1-benzofuran-5-ylmethylidene)-2-(3-imidazol-1-ylpropylamino)-1,3-thiazol-4-one Chemical compound S1C(=CC=2C=C3CCOC3=CC=2)C(=O)N=C1NCCCN1C=CN=C1 NYSIWPJIULZPCZ-UHFFFAOYSA-N 0.000 claims 2
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical group COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
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208000001647 Renal Insufficiency Diseases 0.000 description 6
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150000001299 aldehydes Chemical class 0.000 description 6
229910052740 iodine Inorganic materials 0.000 description 6
150000003254 radicals Chemical class 0.000 description 6
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WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 1
230000035790 physiological processes and functions Effects 0.000 description 1
238000005498 polishing Methods 0.000 description 1
229920000747 poly(lactic acid) Polymers 0.000 description 1
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239000004626 polylactic acid Substances 0.000 description 1
229920000656 polylysine Polymers 0.000 description 1
229920006324 polyoxymethylene Polymers 0.000 description 1
229920001184 polypeptide Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
238000003825 pressing Methods 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
239000011253 protective coating Substances 0.000 description 1
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230000005855 radiation Effects 0.000 description 1
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230000002441 reversible effect Effects 0.000 description 1
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235000019204 saccharin Nutrition 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
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239000012266 salt solution Substances 0.000 description 1
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239000004208 shellac Substances 0.000 description 1
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ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
230000011664 signaling Effects 0.000 description 1
XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
210000003491 skin Anatomy 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
ABBQHOQBGMUPJH-UHFFFAOYSA-N sodium;2-hydroxybenzoic acid Chemical class [Na+].OC(=O)C1=CC=CC=C1O ABBQHOQBGMUPJH-UHFFFAOYSA-N 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000011476 stem cell transplantation Methods 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
229940100611 topical cream Drugs 0.000 description 1
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235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
230000007704 transition Effects 0.000 description 1
AVBGNFCMKJOFIN-UHFFFAOYSA-N triethylammonium acetate Chemical compound CC(O)=O.CCN(CC)CC AVBGNFCMKJOFIN-UHFFFAOYSA-N 0.000 description 1
125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
238000002604 ultrasonography Methods 0.000 description 1
241000701447 unidentified baculovirus Species 0.000 description 1
239000006216 vaginal suppository Substances 0.000 description 1
229940070710 valerate Drugs 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
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230000003612 virological effect Effects 0.000 description 1
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210000005253 yeast cell Anatomy 0.000 description 1
229930195724 β-lactose Natural products 0.000 description 1

Classifications

- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/426—1,3-Thiazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- 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
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
- 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
- A61P7/06—Antianaemics
- 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
- A61P7/08—Plasma substitutes; Perfusion solutions; Dialytics or haemodialytics; Drugs for electrolytic or acid-base disorders, e.g. hypovolemic shock
- 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
- C07D417/02—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 two hetero rings
- C07D417/06—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 two hetero rings linked by a carbon chain containing only aliphatic carbon 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
- C07D417/02—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 two hetero rings
- C07D417/08—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 two hetero rings linked by a carbon chain containing alicyclic rings
- 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
- C07D417/02—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 two hetero rings
- C07D417/10—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 two hetero rings linked by a carbon chain containing aromatic rings
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Hematology (AREA)
Diabetes (AREA)
Physical Education & Sports Medicine (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Peptides Or Proteins (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Thiazole And Isothizaole Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

UAA200504788A 2002-11-22 2003-11-18 THIAZOLIDINE DERIVATIVES AS hYAK3 INHIBITORS UA80572C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US42838402P	2002-11-22	2002-11-22
PCT/US2003/037658 WO2004047760A2 (en)	2002-11-22	2003-11-18	Novel chemical compounds

Publications (1)

Publication Number	Publication Date
UA80572C2 true UA80572C2 (en)	2007-10-10

Family

ID=32393394

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UAA200504788A UA80572C2 (en)	2002-11-22	2003-11-18	THIAZOLIDINE DERIVATIVES AS hYAK3 INHIBITORS

Country Status (30)

Country	Link
US (1)	US7767701B2 (es)
EP (1)	EP1567112B1 (es)
JP (1)	JP2006509765A (es)
KR (1)	KR20050085115A (es)
CN (1)	CN100579978C (es)
AP (1)	AP1967A (es)
AR (1)	AR045407A1 (es)
AT (1)	ATE411302T1 (es)
AU (1)	AU2003298693B2 (es)
BR (1)	BR0316502A (es)
CA (1)	CA2507256A1 (es)
CY (1)	CY1108655T1 (es)
DE (1)	DE60324178D1 (es)
DK (1)	DK1567112T3 (es)
EA (1)	EA008865B1 (es)
EC (1)	ECSP055808A (es)
ES (1)	ES2315566T3 (es)
IS (1)	IS2659B (es)
MA (1)	MA27701A1 (es)
MX (1)	MXPA05005406A (es)
MY (1)	MY140132A (es)
NO (1)	NO20052928L (es)
NZ (1)	NZ539873A (es)
OA (1)	OA12963A (es)
PL (1)	PL377564A1 (es)
PT (1)	PT1567112E (es)
SI (1)	SI1567112T1 (es)
TW (1)	TWI309648B (es)
UA (1)	UA80572C2 (es)
WO (1)	WO2004047760A2 (es)

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ATE412650T1 (de) *	2003-07-11	2008-11-15	Warner Lambert Co	Isethionat salz eines selektiven cdk4 inhibitors
ES2328146T3 (es) *	2003-07-28	2009-11-10	Merck Serono Sa	2-imino-4-(tio)oxo-5-policiclovinilazolinas para su uso como inhibidores de p13 quinasas.
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EP1718642A4 (en) *	2004-02-25	2010-11-24	Glaxosmithkline Llc	NEW CHEMICAL COMPOUNDS
TW200616967A (en)	2004-06-24	2006-06-01	Smithkline Beecham Corp	Novel indazole carboxamides and their use
EP1765817A1 (en) *	2004-07-01	2007-03-28	F.Hoffmann-La Roche Ag	Thiazolinone unsubstituted quinolines
JP2008504323A (ja) *	2004-07-01	2008-02-14	エフ．ホフマン−ラ　ロシュ　アーゲー	抗増殖活性を有するキノリンチアゾリノン
US7241893B2 (en) *	2004-09-17	2007-07-10	Hoffman-La Roche Inc.	Thiazolinone 2-substituted quinolines
US7253285B2 (en) *	2004-09-17	2007-08-07	Hoffmann-La Roche Inc.	Thiazolinone 4-monosubstituted quinolines
BRPI0517416A (pt) *	2004-10-12	2008-10-07	Serono Lab	inibidores de pi3 quinase gama para o tratamento de anemia
CA2583192A1 (en) *	2004-10-14	2006-04-20	F. Hoffmann-La Roche Ag	1,5-naphthyridine azolidinones having cdk1 antiproliferative activity
MX2007004273A (es) *	2004-10-14	2007-05-11	Hoffmann La Roche	Nuevas azaindol-tiazolinonas como agentes anti-cancerosos.
BRPI0518164A (pt)	2004-10-14	2008-11-04	Hoffmann La Roche	quinazolinilmetilenotiazolinonas como inibidores de cdk1
US7304074B2 (en)	2005-04-05	2007-12-04	Hoffmann-La Roche Inc.	Substituted 1,5-naphthyridine azolinones
TW200716132A (en) *	2005-05-03	2007-05-01	Smithkline Beecham Corp	Novel chemical compounds
JP2008545690A (ja) *	2005-05-23	2008-12-18	スミスクライン・ビーチャム・コーポレイション	新規化合物
EP1888557A4 (en) *	2005-06-08	2012-02-15	Glaxosmithkline Llc	(5Z) -5- (6-QUINOXALINYLMETHYLIDENE) -2-Ý (2,4,6-trichlorophenyl) amino-1,3-thiazol-4 (5H) -one
TW200716580A (en) *	2005-06-08	2007-05-01	Smithkline Beecham Corp	(5Z)-5-(6-quinoxalinylmethylidene)-2-[(2,6-dichlorophenyl)amino]-1,3-thiazol-4(5H)-one
TW200745066A (en)	2005-09-16	2007-12-16	Torrent Pharmaceuticals Ltd	Novel PTP1B inhibitors
EP1954136A4 (en) *	2005-11-08	2011-01-05	Glaxosmithkline Llc	NEW CHEMICAL COMPOUNDS
EP1993538A4 (en) *	2006-03-02	2010-05-19	Glaxosmithkline Llc	THIAZOLONES AS INHIBITORS OF P13-KINASES
US20090023742A1 (en) *	2006-03-02	2009-01-22	Dashyant Dhanak	Thiazolones for use as pi3 kinase inhibitors
KR100752757B1 (ko) *	2006-04-05	2007-08-29	한국과학기술연구원	2-페닐이미노-1,3-티아졸린을 포함하는 미백 조성물
EP2016062A2 (en) *	2006-04-25	2009-01-21	The Cleveland Clinic Foundation	Anti-viral agents that activate rnase l
US8912340B2 (en)	2006-11-23	2014-12-16	Actelion Pharmaceuticals Ltd.	Process for the preparation of 2-imino-thiazolidin-4-one derivatives
JP4669564B2 (ja) *	2006-11-23	2011-04-13	アクテリオンファーマシューティカルズリミテッド	２−イミノ−チアゾリジン−４−オン誘導体の製造のための新規な方法
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- 2003-11-18 EA EA200500856A patent/EA008865B1/ru not_active IP Right Cessation
- 2003-11-18 KR KR1020057009243A patent/KR20050085115A/ko not_active Ceased
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- 2003-11-18 US US10/535,690 patent/US7767701B2/en not_active Expired - Fee Related
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Also Published As

Publication number	Publication date
MA27701A1 (fr)	2006-01-02
SI1567112T1 (sl)	2009-02-28
AU2003298693B2 (en)	2010-09-30
TW200418819A (en)	2004-10-01
KR20050085115A (ko)	2005-08-29
MY140132A (en)	2009-11-30
AP1967A (en)	2009-03-10
NZ539873A (en)	2008-09-26
MXPA05005406A (es)	2005-08-03
TWI309648B (en)	2009-05-11
EA008865B1 (ru)	2007-08-31
EP1567112B1 (en)	2008-10-15
PL377564A1 (pl)	2006-02-06
CN1742010A (zh)	2006-03-01
US20060293338A1 (en)	2006-12-28
CN100579978C (zh)	2010-01-13
CY1108655T1 (el)	2014-04-09
ECSP055808A (es)	2005-09-20
ES2315566T3 (es)	2009-04-01
WO2004047760A2 (en)	2004-06-10
EA200500856A1 (ru)	2005-10-27
EP1567112A2 (en)	2005-08-31
WO2004047760A3 (en)	2004-10-21
AP2005003304A0 (en)	2005-06-30
CA2507256A1 (en)	2004-06-10
OA12963A (en)	2006-10-13
IS2659B (is)	2010-08-15
HK1083443A1 (en)	2006-07-07
IS7879A (is)	2005-06-02
AU2003298693A1 (en)	2004-06-18
EP1567112A4 (en)	2006-11-15
DK1567112T3 (da)	2009-02-09
AR045407A1 (es)	2005-10-26
NO20052928L (no)	2005-08-17
NO20052928D0 (no)	2005-06-15
JP2006509765A (ja)	2006-03-23
BR0316502A (pt)	2005-10-04
DE60324178D1 (de)	2008-11-27
US7767701B2 (en)	2010-08-03
ATE411302T1 (de)	2008-10-15
PT1567112E (pt)	2009-01-08

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