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
108060006633 protein kinase Proteins 0.000 description 1
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125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
230000005855 radiation Effects 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
238000001953 recrystallisation Methods 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
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
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238000007789 sealing Methods 0.000 description 1
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239000004208 shellac Substances 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
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
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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
229940100615 topical ointment Drugs 0.000 description 1
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
235000013311 vegetables Nutrition 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
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238000005303 weighing Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
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229940082509 xanthan gum Drugs 0.000 description 1
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)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (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 (fr)	2002-11-22	2003-11-18	Nouveaux composes chimiques

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

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DE602004017474D1 (de) *	2003-07-11	2008-12-11	Warner Lambert Co	Isethionat salz eines selektiven cdk4 inhibitors
CA2531140C (fr) *	2003-07-28	2013-06-18	Applied Research Systems Ars Holding N.V.	2-imino-4-(thio) oxo-5-polycyclovinylazolines utilises comme inhibiteurs de la kinase pi3
BRPI0416752B8 (pt)	2003-11-21	2021-05-25	Actelion Pharmaceuticals Ltd	composição farmacêutica, uso de um ou mais compostos, e, compostos
USRE43833E1 (en)	2003-11-21	2012-11-27	Actelion Pharmaceuticals Ltd.	Thiazolidin-4-one derivatives
US20070249599A1 (en) *	2004-02-25	2007-10-25	Duffy Kevin J	Novel Chemical Compounds
TW200616967A (en)	2004-06-24	2006-06-01	Smithkline Beecham Corp	Novel indazole carboxamides and their use
RU2007103709A (ru)	2004-07-01	2008-08-10	Ф.Хоффманн-Ля Рош Аг (Ch)	Тиазолинонхинолины
ES2317238T3 (es) *	2004-07-01	2009-04-16	F. Hoffmann-La Roche Ag	Quinolina-tiazolinonas con actividad antiproliferante cdk-1.
US7253285B2 (en) *	2004-09-17	2007-08-07	Hoffmann-La Roche Inc.	Thiazolinone 4-monosubstituted quinolines
US7241893B2 (en) *	2004-09-17	2007-07-10	Hoffman-La Roche Inc.	Thiazolinone 2-substituted quinolines
MX2007004302A (es) *	2004-10-12	2007-06-07	Applied Research Systems	Inhibidores de pi3 cinasa gamma para el tratamiento de anemia.
KR20080075235A (ko) *	2004-10-14	2008-08-14	에프. 호프만-라 로슈 아게	Ｃｄｋ1 항증식성 활성을 갖는 1,5-나프티리딘 아졸리디논
WO2006040050A1 (fr) *	2004-10-14	2006-04-20	F.Hoffmann-La Roche Ag	Quinazolinylmethylene thiazolinones en tant qu'inhibiteurs de cdk1
BRPI0518158A (pt) *	2004-10-14	2008-11-04	Hoffmann La Roche	tiazolinonas de azaindol como agentes anti-cáncer
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
US20080194466A1 (en) *	2005-06-08	2008-08-14	Duffy Kevin J	(5Z)-5-(6-Quinoxalinylmethylidene)-2-[(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 (fr) *	2005-11-08	2011-01-05	Glaxosmithkline Llc	Nouveaux composés chimiques
JP2009528386A (ja) *	2006-03-02	2009-08-06	スミスクライン・ビーチャム・コーポレイション	Ｐｉ３キナーゼ阻害剤として用いるためのチアゾロン
WO2007103754A2 (fr) *	2006-03-02	2007-09-13	Smithkline Beecham Corporation	Thiazolones utilisés en tant qu'inhibiteurs de p13-kinases
KR100752757B1 (ko) *	2006-04-05	2007-08-29	한국과학기술연구원	2-페닐이미노-1,3-티아졸린을 포함하는 미백 조성물
AU2007243403A1 (en) *	2006-04-25	2007-11-08	Northern Arizona University	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
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- 2003-11-18 KR KR1020057009243A patent/KR20050085115A/ko not_active Ceased
- 2003-11-18 AU AU2003298693A patent/AU2003298693B2/en not_active Ceased
- 2003-11-18 AT AT03796448T patent/ATE411302T1/de active
- 2003-11-18 BR BR0316502-7A patent/BR0316502A/pt not_active IP Right Cessation
- 2003-11-18 MX MXPA05005406A patent/MXPA05005406A/es active IP Right Grant
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- 2003-11-18 US US10/535,690 patent/US7767701B2/en not_active Expired - Fee Related
- 2003-11-18 PL PL377564A patent/PL377564A1/pl not_active Application Discontinuation
- 2003-11-18 AP AP2005003304A patent/AP1967A/xx active
- 2003-11-18 OA OA1200500154A patent/OA12963A/en unknown
- 2003-11-18 CA CA002507256A patent/CA2507256A1/fr not_active Abandoned
- 2003-11-18 JP JP2004555721A patent/JP2006509765A/ja not_active Ceased
- 2003-11-18 PT PT03796448T patent/PT1567112E/pt unknown
- 2003-11-18 EA EA200500856A patent/EA008865B1/ru not_active IP Right Cessation
- 2003-11-18 DK DK03796448T patent/DK1567112T3/da active
- 2003-11-18 UA UAA200504788A patent/UA80572C2/uk unknown
- 2003-11-18 CN CN200380109119A patent/CN100579978C/zh not_active Expired - Fee Related
- 2003-11-18 DE DE60324178T patent/DE60324178D1/de not_active Expired - Lifetime
- 2003-11-18 EP EP03796448A patent/EP1567112B1/fr not_active Expired - Lifetime
- 2003-11-18 WO PCT/US2003/037658 patent/WO2004047760A2/fr not_active Ceased
- 2003-11-18 ES ES03796448T patent/ES2315566T3/es not_active Expired - Lifetime
- 2003-11-18 SI SI200331463T patent/SI1567112T1/sl unknown
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- 2003-11-20 AR ARP030104299A patent/AR045407A1/es not_active Application Discontinuation
- 2003-11-20 TW TW092132476A patent/TWI309648B/zh not_active IP Right Cessation
2005
- 2005-05-20 EC EC2005005808A patent/ECSP055808A/es unknown
- 2005-05-27 MA MA28303A patent/MA27701A1/fr unknown
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- 2005-06-15 NO NO20052928A patent/NO20052928L/no not_active Application Discontinuation
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Also Published As

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

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