HRP20041142A2 - Thiazolidinones and the use thereof as polo-like kinase inhibitors - Google Patents
Thiazolidinones and the use thereof as polo-like kinase inhibitorsInfo
- Publication number
- HRP20041142A2 HRP20041142A2 HR20041142A HRP20041142A HRP20041142A2 HR P20041142 A2 HRP20041142 A2 HR P20041142A2 HR 20041142 A HR20041142 A HR 20041142A HR P20041142 A HRP20041142 A HR P20041142A HR P20041142 A2 HRP20041142 A2 HR P20041142A2
- Authority
- HR
- Croatia
- Prior art keywords
- alkyl
- alkylene
- image
- hydroxy
- groups
- Prior art date
Links
- 239000002770 polo like kinase inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 172
- -1 R15 Chemical compound 0.000 claims description 130
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 97
- 239000000126 substance Substances 0.000 claims description 78
- 239000000203 mixture Substances 0.000 claims description 68
- 229910052739 hydrogen Inorganic materials 0.000 claims description 56
- 239000001257 hydrogen Substances 0.000 claims description 56
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 54
- 150000002431 hydrogen Chemical class 0.000 claims description 47
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 43
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 26
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 239000013067 intermediate product Substances 0.000 claims description 19
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 16
- 206010028980 Neoplasm Diseases 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 12
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 201000011510 cancer Diseases 0.000 claims description 11
- 125000004076 pyridyl group Chemical group 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 125000003107 substituted aryl group Chemical group 0.000 claims description 10
- 108091000080 Phosphotransferase Proteins 0.000 claims description 9
- 125000002883 imidazolyl group Chemical group 0.000 claims description 9
- 102000020233 phosphotransferase Human genes 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical class 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 8
- 230000004770 neurodegeneration Effects 0.000 claims description 8
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
- 125000002757 morpholinyl group Chemical group 0.000 claims description 7
- 125000003386 piperidinyl group Chemical group 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 6
- 201000004384 Alopecia Diseases 0.000 claims description 6
- 208000023275 Autoimmune disease Diseases 0.000 claims description 6
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 6
- 208000035473 Communicable disease Diseases 0.000 claims description 6
- 229910003849 O-Si Inorganic materials 0.000 claims description 6
- 229910003872 O—Si Inorganic materials 0.000 claims description 6
- 231100000360 alopecia Toxicity 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 208000036142 Viral infection Diseases 0.000 claims description 5
- 230000001684 chronic effect Effects 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 230000009385 viral infection Effects 0.000 claims description 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- 230000001154 acute effect Effects 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 3
- 206010018364 Glomerulonephritis Diseases 0.000 claims description 3
- 208000023105 Huntington disease Diseases 0.000 claims description 3
- 206010028116 Mucosal inflammation Diseases 0.000 claims description 3
- 201000010927 Mucositis Diseases 0.000 claims description 3
- 101150005816 PLK4 gene Proteins 0.000 claims description 3
- 208000031481 Pathologic Constriction Diseases 0.000 claims description 3
- 101150011368 Plk2 gene Proteins 0.000 claims description 3
- 201000004681 Psoriasis Diseases 0.000 claims description 3
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 3
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- 208000032839 leukemia Diseases 0.000 claims description 3
- 201000006417 multiple sclerosis Diseases 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 244000045947 parasite Species 0.000 claims description 3
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 3
- 108010056274 polo-like kinase 1 Proteins 0.000 claims description 3
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 208000037803 restenosis Diseases 0.000 claims description 3
- 125000001425 triazolyl group Chemical group 0.000 claims description 3
- 208000030507 AIDS Diseases 0.000 claims description 2
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- 201000006474 Brain Ischemia Diseases 0.000 claims description 2
- 125000006725 C1-C10 alkenyl group Chemical group 0.000 claims description 2
- 206010011831 Cytomegalovirus infection Diseases 0.000 claims description 2
- 206010012289 Dementia Diseases 0.000 claims description 2
- 208000031886 HIV Infections Diseases 0.000 claims description 2
- 208000005176 Hepatitis C Diseases 0.000 claims description 2
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 claims description 2
- 208000018737 Parkinson disease Diseases 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 208000002672 hepatitis B Diseases 0.000 claims description 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000000405 phenylalanyl group Chemical group 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 101150067958 plk-3 gene Proteins 0.000 claims description 2
- 208000037804 stenosis Diseases 0.000 claims description 2
- 230000036262 stenosis Effects 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 239000008177 pharmaceutical agent Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 169
- 238000005160 1H NMR spectroscopy Methods 0.000 description 156
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 156
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 141
- 239000000047 product Substances 0.000 description 125
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 108
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 104
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 91
- 229910000027 potassium carbonate Inorganic materials 0.000 description 78
- 235000015320 potassium carbonate Nutrition 0.000 description 74
- 238000000034 method Methods 0.000 description 71
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 68
- 238000005352 clarification Methods 0.000 description 68
- 239000000243 solution Substances 0.000 description 63
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 59
- 229960000583 acetic acid Drugs 0.000 description 58
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 45
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
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- 230000001419 dependent effect Effects 0.000 description 40
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- HBNYJWAFDZLWRS-UHFFFAOYSA-N ethyl isothiocyanate Chemical compound CCN=C=S HBNYJWAFDZLWRS-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
- 210000004027 cell Anatomy 0.000 description 18
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 18
- 239000012043 crude product Substances 0.000 description 17
- SYZRZLUNWVNNNV-UHFFFAOYSA-N 2-bromoacetyl chloride Chemical compound ClC(=O)CBr SYZRZLUNWVNNNV-UHFFFAOYSA-N 0.000 description 16
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
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- 238000006243 chemical reaction Methods 0.000 description 10
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
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- 239000012317 TBTU Substances 0.000 description 7
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 7
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Classifications
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- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- C07D277/32—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 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/34—Oxygen atoms
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- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/82—Nitrogen atoms
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- 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
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- 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
- C07D417/12—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 chain containing hetero atoms as chain links
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE10221104 | 2002-05-03 | ||
PCT/EP2003/004450 WO2003093249A1 (de) | 2002-05-03 | 2003-04-29 | Thiazolidinone und ihre verwendung als polo like kinase inhibitoren |
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HRP20041142A2 true HRP20041142A2 (en) | 2005-10-31 |
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HR20041142A HRP20041142A2 (en) | 2002-05-03 | 2004-11-30 | Thiazolidinones and the use thereof as polo-like kinase inhibitors |
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US (1) | US20060079503A1 (zh) |
EP (1) | EP1501794A1 (zh) |
JP (1) | JP2005538048A (zh) |
KR (1) | KR20040106451A (zh) |
CN (1) | CN1649853A (zh) |
AR (1) | AR040074A1 (zh) |
AU (1) | AU2003222845A1 (zh) |
BR (1) | BR0309758A (zh) |
CA (1) | CA2484597A1 (zh) |
EC (1) | ECSP045476A (zh) |
HR (1) | HRP20041142A2 (zh) |
IL (1) | IL164651A0 (zh) |
MX (1) | MXPA04010169A (zh) |
NO (1) | NO20045281L (zh) |
PE (1) | PE20040589A1 (zh) |
PL (1) | PL372890A1 (zh) |
RS (1) | RS95404A (zh) |
RU (1) | RU2004135533A (zh) |
TW (1) | TW200406392A (zh) |
WO (1) | WO2003093249A1 (zh) |
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US6861422B2 (en) | 2003-02-26 | 2005-03-01 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Dihydropteridinones, processes for preparing them and their use as pharmaceutical compositions |
DE10351744A1 (de) * | 2003-10-31 | 2005-06-16 | Schering Ag | Thiazolidinone, deren Herstellung und Verwendung als Arzneimittel |
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WO2000075139A2 (en) * | 1999-06-03 | 2000-12-14 | Basf Aktiengesellschaft | Benzothiazinone and benzoxazinone compounds |
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DE102005005395A1 (de) * | 2005-02-03 | 2006-08-10 | Schering Aktiengesellschaft | Thiazolidinone, deren Herstellung und Verwendung als Arzneimittel |
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- 2003-04-29 CA CA002484597A patent/CA2484597A1/en not_active Abandoned
- 2003-04-29 CN CNA038100428A patent/CN1649853A/zh active Pending
- 2003-04-29 WO PCT/EP2003/004450 patent/WO2003093249A1/de active Application Filing
- 2003-04-29 US US10/513,368 patent/US20060079503A1/en not_active Abandoned
- 2003-04-29 JP JP2004501388A patent/JP2005538048A/ja active Pending
- 2003-04-29 EP EP03718796A patent/EP1501794A1/de not_active Withdrawn
- 2003-04-29 MX MXPA04010169A patent/MXPA04010169A/es not_active Application Discontinuation
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- 2003-04-29 RU RU2004135533/04A patent/RU2004135533A/ru not_active Application Discontinuation
- 2003-04-29 KR KR10-2004-7017635A patent/KR20040106451A/ko not_active Application Discontinuation
- 2003-05-02 TW TW092112164A patent/TW200406392A/zh unknown
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- 2004-11-30 HR HR20041142A patent/HRP20041142A2/hr not_active Application Discontinuation
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AU2003222845A1 (en) | 2003-11-17 |
NO20045281L (no) | 2005-02-01 |
PE20040589A1 (es) | 2004-11-21 |
CA2484597A1 (en) | 2003-11-13 |
IL164651A0 (en) | 2005-12-18 |
MXPA04010169A (es) | 2005-02-03 |
TW200406392A (en) | 2004-05-01 |
RS95404A (en) | 2006-10-27 |
RU2004135533A (ru) | 2005-07-20 |
PL372890A1 (en) | 2005-08-08 |
EP1501794A1 (de) | 2005-02-02 |
AR040074A1 (es) | 2005-03-16 |
CN1649853A (zh) | 2005-08-03 |
KR20040106451A (ko) | 2004-12-17 |
WO2003093249A1 (de) | 2003-11-13 |
JP2005538048A (ja) | 2005-12-15 |
ECSP045476A (es) | 2005-01-28 |
US20060079503A1 (en) | 2006-04-13 |
ZA200409796B (zh) | 2006-06-28 |
BR0309758A (pt) | 2005-02-15 |
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