ES2236034T3 - N- (5-(((5-alquil-2-oxazolil)metil)tio)-2-tiazolil carboxamida inhibidores de las cinasas dependientes de ciclina. - Google Patents
N- (5-(((5-alquil-2-oxazolil)metil)tio)-2-tiazolil carboxamida inhibidores de las cinasas dependientes de ciclina.Info
- Publication number
- ES2236034T3 ES2236034T3 ES00990204T ES00990204T ES2236034T3 ES 2236034 T3 ES2236034 T3 ES 2236034T3 ES 00990204 T ES00990204 T ES 00990204T ES 00990204 T ES00990204 T ES 00990204T ES 2236034 T3 ES2236034 T3 ES 2236034T3
- Authority
- ES
- Spain
- Prior art keywords
- methyl
- compound according
- oxazolyl
- thio
- dimethylethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 230000001419 dependent effect Effects 0.000 title claims description 4
- 239000003112 inhibitor Substances 0.000 title description 4
- 150000003857 carboxamides Chemical class 0.000 title 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 title 1
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 114
- 150000003839 salts Chemical class 0.000 claims abstract description 53
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 19
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 15
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 52
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 34
- -1 dihydrochloride Chemical class 0.000 claims description 29
- OUSFTKFNBAZUKL-UHFFFAOYSA-N N-(5-{[(5-tert-butyl-1,3-oxazol-2-yl)methyl]sulfanyl}-1,3-thiazol-2-yl)piperidine-4-carboxamide Chemical compound O1C(C(C)(C)C)=CN=C1CSC(S1)=CN=C1NC(=O)C1CCNCC1 OUSFTKFNBAZUKL-UHFFFAOYSA-N 0.000 claims description 26
- 238000011282 treatment Methods 0.000 claims description 23
- 239000003814 drug Substances 0.000 claims description 19
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 14
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 12
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical class [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 12
- 108091000080 Phosphotransferase Proteins 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 11
- 230000005764 inhibitory process Effects 0.000 claims description 11
- 102000020233 phosphotransferase Human genes 0.000 claims description 11
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 10
- 206010028980 Neoplasm Diseases 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 101150012716 CDK1 gene Proteins 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 6
- 101100059559 Emericella nidulans (strain FGSC A4 / ATCC 38163 / CBS 112.46 / NRRL 194 / M139) nimX gene Proteins 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical class [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 6
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 claims description 6
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 claims description 6
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 claims description 6
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 6
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- 206010003246 arthritis Diseases 0.000 claims description 5
- 201000011510 cancer Diseases 0.000 claims description 5
- NASKBLMGBFRGIF-UHFFFAOYSA-N n-[5-[(5-tert-butyl-1,3-oxazol-2-yl)methylsulfanyl]-1,3-thiazol-2-yl]-1-(2-hydroxyethyl)piperidine-4-carboxamide Chemical compound O1C(C(C)(C)C)=CN=C1CSC(S1)=CN=C1NC(=O)C1CCN(CCO)CC1 NASKBLMGBFRGIF-UHFFFAOYSA-N 0.000 claims description 5
- BMJRSDXYHRHHKI-UHFFFAOYSA-N n-[5-[(5-tert-butyl-1,3-oxazol-2-yl)methylsulfanyl]-1,3-thiazol-2-yl]-1-cyclopropylpiperidine-4-carboxamide Chemical compound O1C(C(C)(C)C)=CN=C1CSC(S1)=CN=C1NC(=O)C1CCN(C2CC2)CC1 BMJRSDXYHRHHKI-UHFFFAOYSA-N 0.000 claims description 5
- JJJVIPYJUNRQTI-UHFFFAOYSA-N n-[5-[(5-tert-butyl-1,3-oxazol-2-yl)methylsulfanyl]-1,3-thiazol-2-yl]-1-propan-2-ylpiperidine-4-carboxamide Chemical compound C1CN(C(C)C)CCC1C(=O)NC(S1)=NC=C1SCC1=NC=C(C(C)(C)C)O1 JJJVIPYJUNRQTI-UHFFFAOYSA-N 0.000 claims description 5
- USAKOZCUIYTREA-UHFFFAOYSA-N n-[5-[(5-tert-butyl-1,3-oxazol-2-yl)methylsulfanyl]-1,3-thiazol-2-yl]piperidine-3-carboxamide Chemical compound O1C(C(C)(C)C)=CN=C1CSC(S1)=CN=C1NC(=O)C1CNCCC1 USAKOZCUIYTREA-UHFFFAOYSA-N 0.000 claims description 5
- 108090000266 Cyclin-dependent kinases Proteins 0.000 claims description 3
- 102000003903 Cyclin-dependent kinases Human genes 0.000 claims description 3
- 206010061218 Inflammation Diseases 0.000 claims description 3
- 102000001253 Protein Kinase Human genes 0.000 claims description 3
- 230000006907 apoptotic process Effects 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 230000004054 inflammatory process Effects 0.000 claims description 3
- LURBGHNXFQSPMM-UHFFFAOYSA-N n-[5-[(5-tert-butyl-1,3-oxazol-2-yl)methylsulfanyl]-1,3-thiazol-2-yl]-1-(2,3-dihydroxypropyl)piperidine-4-carboxamide Chemical compound O1C(C(C)(C)C)=CN=C1CSC(S1)=CN=C1NC(=O)C1CCN(CC(O)CO)CC1 LURBGHNXFQSPMM-UHFFFAOYSA-N 0.000 claims description 3
- 230000002062 proliferating effect Effects 0.000 claims description 3
- 108060006633 protein kinase Proteins 0.000 claims description 3
- 239000003981 vehicle Substances 0.000 claims description 3
- 108091007914 CDKs Proteins 0.000 claims description 2
- 101100005789 Caenorhabditis elegans cdk-4 gene Proteins 0.000 claims description 2
- 101150053721 Cdk5 gene Proteins 0.000 claims description 2
- 206010052779 Transplant rejections Diseases 0.000 claims description 2
- 101150073031 cdk2 gene Proteins 0.000 claims description 2
- 208000035475 disorder Diseases 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 230000023603 positive regulation of transcription initiation, DNA-dependent Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 16
- USAKOZCUIYTREA-LLVKDONJSA-N (3r)-n-[5-[(5-tert-butyl-1,3-oxazol-2-yl)methylsulfanyl]-1,3-thiazol-2-yl]piperidine-3-carboxamide Chemical compound O1C(C(C)(C)C)=CN=C1CSC(S1)=CN=C1NC(=O)[C@H]1CNCCC1 USAKOZCUIYTREA-LLVKDONJSA-N 0.000 claims 1
- 101150090188 Cdk8 gene Proteins 0.000 claims 1
- 101150112625 SSN3 gene Proteins 0.000 claims 1
- 101100150415 Schizosaccharomyces pombe (strain 972 / ATCC 24843) srb10 gene Proteins 0.000 claims 1
- 230000001093 anti-cancer Effects 0.000 claims 1
- 101150059448 cdk7 gene Proteins 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000000968 intestinal effect Effects 0.000 claims 1
- 150000003892 tartrate salts Chemical class 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 93
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 83
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
- 239000007787 solid Substances 0.000 description 45
- 239000000243 solution Substances 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- 239000011541 reaction mixture Substances 0.000 description 31
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- 239000002253 acid Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000000284 extract Substances 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 15
- 238000004128 high performance liquid chromatography Methods 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
- 239000002244 precipitate Substances 0.000 description 14
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 14
- 239000000725 suspension Substances 0.000 description 14
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 12
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 12
- 229910052938 sodium sulfate Inorganic materials 0.000 description 12
- 235000011152 sodium sulphate Nutrition 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 9
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- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 8
- 239000007832 Na2SO4 Substances 0.000 description 8
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- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 6
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- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
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- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
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- 241000701447 unidentified baculovirus Species 0.000 description 4
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 3
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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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- C07—ORGANIC CHEMISTRY
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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- 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
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- Health & Medical Sciences (AREA)
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- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Dermatology (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)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US464511 | 1999-12-15 | ||
| US09/464,511 US6262096B1 (en) | 1997-11-12 | 1999-12-15 | Aminothiazole inhibitors of cyclin dependent kinases |
| US61662700A | 2000-07-26 | 2000-07-26 | |
| US616627 | 2000-07-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2236034T3 true ES2236034T3 (es) | 2005-07-16 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES00990204T Expired - Lifetime ES2236034T3 (es) | 1999-12-15 | 2000-12-07 | N- (5-(((5-alquil-2-oxazolil)metil)tio)-2-tiazolil carboxamida inhibidores de las cinasas dependientes de ciclina. |
Country Status (29)
| Country | Link |
|---|---|
| EP (1) | EP1240166B1 (enExample) |
| JP (1) | JP2003516987A (enExample) |
| KR (1) | KR100738132B1 (enExample) |
| CN (1) | CN1433416A (enExample) |
| AR (1) | AR026974A1 (enExample) |
| AT (1) | ATE289306T1 (enExample) |
| AU (1) | AU783719B2 (enExample) |
| BR (1) | BR0016424A (enExample) |
| CA (1) | CA2394552A1 (enExample) |
| CO (1) | CO5261565A1 (enExample) |
| CZ (1) | CZ20022015A3 (enExample) |
| DE (1) | DE60018205T2 (enExample) |
| DK (1) | DK1240166T3 (enExample) |
| EG (1) | EG24168A (enExample) |
| ES (1) | ES2236034T3 (enExample) |
| HK (1) | HK1049661B (enExample) |
| HU (1) | HUP0301032A3 (enExample) |
| IL (2) | IL149755A0 (enExample) |
| MX (1) | MXPA02005870A (enExample) |
| MY (1) | MY125768A (enExample) |
| NO (1) | NO323726B1 (enExample) |
| NZ (1) | NZ519120A (enExample) |
| PE (1) | PE20011026A1 (enExample) |
| PL (1) | PL364921A1 (enExample) |
| PT (1) | PT1240166E (enExample) |
| RU (1) | RU2002119016A (enExample) |
| TW (1) | TWI273103B (enExample) |
| UY (1) | UY26481A1 (enExample) |
| WO (1) | WO2001044242A1 (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6262096B1 (en) | 1997-11-12 | 2001-07-17 | Bristol-Myers Squibb Company | Aminothiazole inhibitors of cyclin dependent kinases |
| US6414156B2 (en) * | 1998-10-21 | 2002-07-02 | Bristol-Myers Squibb Company | Process for preparing azacycloalkanoylaminothiazoles |
| US6392053B2 (en) | 1999-12-15 | 2002-05-21 | Bristol-Myers Squibb Company | Process for preparing arylacetylaminothiazoles |
| US6515004B1 (en) | 1999-12-15 | 2003-02-04 | Bristol-Myers Squibb Company | N-[5-[[[5-alkyl-2-oxazolyl]methyl]thio]-2-thiazolyl]-carboxamide inhibitors of cyclin dependent kinases |
| WO2002010162A1 (en) * | 2000-07-26 | 2002-02-07 | Bristol-Myers Squibb Company | N-[5-[[[5-alkyl-2-oxazolyl]methyl]thio]-2-thiazolyl] carboxamide inhibitors of cyclin dependent kinases |
| US7473691B2 (en) | 2000-09-15 | 2009-01-06 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| US6660731B2 (en) | 2000-09-15 | 2003-12-09 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| US6638926B2 (en) | 2000-09-15 | 2003-10-28 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| CA2432799C (en) | 2000-12-21 | 2008-08-19 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| MY141867A (en) | 2002-06-20 | 2010-07-16 | Vertex Pharma | Substituted pyrimidines useful as protein kinase inhibitors |
| PT1532145E (pt) | 2002-08-02 | 2007-01-31 | Vertex Pharma | Composiçoes de pirazole úteis como inibidores de gsk-3 |
| US7392929B1 (en) | 2004-07-26 | 2008-07-01 | Zephyros, Inc. | Weldable synthetic material |
| WO2006077428A1 (en) | 2005-01-21 | 2006-07-27 | Astex Therapeutics Limited | Pharmaceutical compounds |
| DE102005008310A1 (de) * | 2005-02-17 | 2006-08-24 | Schering Ag | Verwendung von CDKII Inhibitoren zur Fertilitätskontrolle |
| WO2007056163A2 (en) | 2005-11-03 | 2007-05-18 | Vertex Pharmaceuticals Incorporated | Aminopyrimidines useful as kinase inhibitors |
| JP5528807B2 (ja) | 2006-10-12 | 2014-06-25 | アステックス、セラピューティックス、リミテッド | 複合薬剤 |
| US8916552B2 (en) | 2006-10-12 | 2014-12-23 | Astex Therapeutics Limited | Pharmaceutical combinations |
| US8236128B2 (en) | 2006-10-26 | 2012-08-07 | Zephyros, Inc. | Adhesive materials, adhesive parts formed therewith and their uses |
| WO2008063933A2 (en) * | 2006-11-10 | 2008-05-29 | Massachusetts Institute Of Technology | Pak modulators |
| WO2010033045A1 (en) * | 2008-09-16 | 2010-03-25 | Igor Anatolievich Pomytkin | Compositions and methods for prevention or treatment of beta amyloid deposition |
| AU2010343102B2 (en) | 2009-12-29 | 2016-03-24 | Dana-Farber Cancer Institute, Inc. | Type II Raf kinase inhibitors |
| CA2972239A1 (en) | 2014-12-23 | 2016-06-30 | Dana-Farber Cancer Institute, Inc. | Inhibitors of cyclin-dependent kinase 7 (cdk7) |
| CN107427521B (zh) | 2015-03-27 | 2021-08-03 | 达纳-法伯癌症研究所股份有限公司 | 细胞周期蛋白依赖性激酶的抑制剂 |
| EP4019515A1 (en) | 2015-09-09 | 2022-06-29 | Dana-Farber Cancer Institute, Inc. | Inhibitors of cyclin-dependent kinases |
| JP7590185B2 (ja) | 2018-06-25 | 2024-11-26 | ダナ－ファーバー キャンサー インスティテュート， インコーポレイテッド | Ｔａｉｒｅファミリーキナーゼインヒビターおよびそれらの使用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6040321A (en) * | 1997-11-12 | 2000-03-21 | Bristol-Myers Squibb Company | Aminothiazole inhibitors of cyclin dependent kinases |
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2000
- 2000-11-16 MY MYPI20005385A patent/MY125768A/en unknown
- 2000-12-07 HK HK03100935.5A patent/HK1049661B/en not_active IP Right Cessation
- 2000-12-07 CA CA002394552A patent/CA2394552A1/en not_active Abandoned
- 2000-12-07 MX MXPA02005870A patent/MXPA02005870A/es active IP Right Grant
- 2000-12-07 JP JP2001544732A patent/JP2003516987A/ja not_active Withdrawn
- 2000-12-07 AU AU27264/01A patent/AU783719B2/en not_active Ceased
- 2000-12-07 PT PT00990204T patent/PT1240166E/pt unknown
- 2000-12-07 EP EP00990204A patent/EP1240166B1/en not_active Expired - Lifetime
- 2000-12-07 NZ NZ519120A patent/NZ519120A/en unknown
- 2000-12-07 AT AT00990204T patent/ATE289306T1/de not_active IP Right Cessation
- 2000-12-07 BR BR0016424-0A patent/BR0016424A/pt not_active Application Discontinuation
- 2000-12-07 DE DE60018205T patent/DE60018205T2/de not_active Expired - Fee Related
- 2000-12-07 CZ CZ20022015A patent/CZ20022015A3/cs unknown
- 2000-12-07 ES ES00990204T patent/ES2236034T3/es not_active Expired - Lifetime
- 2000-12-07 IL IL14975500A patent/IL149755A0/xx unknown
- 2000-12-07 RU RU2002119016/04A patent/RU2002119016A/ru unknown
- 2000-12-07 PL PL00364921A patent/PL364921A1/xx not_active Application Discontinuation
- 2000-12-07 WO PCT/US2000/033501 patent/WO2001044242A1/en not_active Ceased
- 2000-12-07 CN CN00818900A patent/CN1433416A/zh active Pending
- 2000-12-07 KR KR1020027007615A patent/KR100738132B1/ko not_active Expired - Fee Related
- 2000-12-07 DK DK00990204T patent/DK1240166T3/da active
- 2000-12-07 HU HU0301032A patent/HUP0301032A3/hu unknown
- 2000-12-09 EG EG20001523A patent/EG24168A/xx active
- 2000-12-14 UY UY26481A patent/UY26481A1/es not_active Application Discontinuation
- 2000-12-14 TW TW089126788A patent/TWI273103B/zh not_active IP Right Cessation
- 2000-12-14 CO CO00095237A patent/CO5261565A1/es not_active Application Discontinuation
- 2000-12-15 AR ARP000106680A patent/AR026974A1/es unknown
- 2000-12-15 PE PE2000001347A patent/PE20011026A1/es not_active Application Discontinuation
-
2002
- 2002-05-20 IL IL149755A patent/IL149755A/en active IP Right Grant
- 2002-06-13 NO NO20022817A patent/NO323726B1/no not_active IP Right Cessation
Also Published As
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