AU2003232754B2 - Diaminothiazoles - Google Patents
Diaminothiazoles Download PDFInfo
- Publication number
- AU2003232754B2 AU2003232754B2 AU2003232754A AU2003232754A AU2003232754B2 AU 2003232754 B2 AU2003232754 B2 AU 2003232754B2 AU 2003232754 A AU2003232754 A AU 2003232754A AU 2003232754 A AU2003232754 A AU 2003232754A AU 2003232754 B2 AU2003232754 B2 AU 2003232754B2
- Authority
- AU
- Australia
- Prior art keywords
- amino
- thiazol
- methanone
- phenyl
- phenylamino
- 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.)
- Ceased
Links
- WKXCZMFWXZRMEZ-UHFFFAOYSA-N 1,3-thiazole-2,4-diamine Chemical class NC1=CSC(N)=N1 WKXCZMFWXZRMEZ-UHFFFAOYSA-N 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 330
- -1 2-pyrrolidin- 1-yl-ethoxy Chemical group 0.000 claims description 266
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 249
- 238000000034 method Methods 0.000 claims description 136
- 125000000217 alkyl group Chemical group 0.000 claims description 130
- 229920005989 resin Polymers 0.000 claims description 113
- 239000011347 resin Substances 0.000 claims description 113
- 229910052736 halogen Inorganic materials 0.000 claims description 47
- 150000002367 halogens Chemical class 0.000 claims description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 239000007787 solid Substances 0.000 claims description 39
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 29
- 125000004429 atom Chemical group 0.000 claims description 25
- 150000002148 esters Chemical class 0.000 claims description 24
- 206010028980 Neoplasm Diseases 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- LLYXUFQXCNIGDG-UHFFFAOYSA-N 3-ethylbenzaldehyde Chemical compound CCC1=CC=CC(C=O)=C1 LLYXUFQXCNIGDG-UHFFFAOYSA-N 0.000 claims description 18
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 125000000872 2-diethylaminoethoxy group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims description 12
- PIKNVEVCWAAOMJ-UHFFFAOYSA-N 3-fluorobenzaldehyde Chemical compound FC1=CC=CC(C=O)=C1 PIKNVEVCWAAOMJ-UHFFFAOYSA-N 0.000 claims description 12
- 201000011510 cancer Diseases 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 9
- WUEPMEXUMQVEGN-UHFFFAOYSA-N 2,2,2-trifluoroacetic acid;2,2,2-trifluoro-n-[2-[2-[(2,2,2-trifluoroacetyl)amino]ethylamino]ethyl]acetamide Chemical compound OC(=O)C(F)(F)F.FC(F)(F)C(=O)NCCNCCNC(=O)C(F)(F)F WUEPMEXUMQVEGN-UHFFFAOYSA-N 0.000 claims description 8
- UFPBMVRONDLOGK-UHFFFAOYSA-N 3-fluoro-4-methylbenzaldehyde Chemical compound CC1=CC=C(C=O)C=C1F UFPBMVRONDLOGK-UHFFFAOYSA-N 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
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- 210000000481 breast Anatomy 0.000 claims description 7
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- COHGKAMBYJGYOZ-UHFFFAOYSA-N 3-cyclopropylbenzaldehyde Chemical compound O=CC1=CC=CC(C2CC2)=C1 COHGKAMBYJGYOZ-UHFFFAOYSA-N 0.000 claims description 6
- QSBHJTCAPWOIIE-UHFFFAOYSA-N 3-fluoro-4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1F QSBHJTCAPWOIIE-UHFFFAOYSA-N 0.000 claims description 6
- 208000026310 Breast neoplasm Diseases 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- PERBLJWTWNTDHV-UHFFFAOYSA-N 3-ethyl-4-fluorobenzaldehyde Chemical compound CCC1=CC(C=O)=CC=C1F PERBLJWTWNTDHV-UHFFFAOYSA-N 0.000 claims description 5
- YTCRQCGRYCKYNO-UHFFFAOYSA-N 4-methoxy-3-nitrobenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1[N+]([O-])=O YTCRQCGRYCKYNO-UHFFFAOYSA-N 0.000 claims description 5
- JQYOOPVLXZGSKP-UHFFFAOYSA-N [4-amino-2-[4-(2-morpholin-4-ylethoxy)anilino]-1,3-thiazol-5-yl]-(3-fluorophenyl)methanone Chemical compound S1C(C(=O)C=2C=C(F)C=CC=2)=C(N)N=C1NC(C=C1)=CC=C1OCCN1CCOCC1 JQYOOPVLXZGSKP-UHFFFAOYSA-N 0.000 claims description 5
- LUKXUACIWWQJHT-UHFFFAOYSA-N [4-amino-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,3-thiazol-5-yl]-(3-fluorophenyl)methanone Chemical compound S1C(C(=O)C=2C=C(F)C=CC=2)=C(N)N=C1NC(C=C1)=CC=C1OCCN1CCCC1 LUKXUACIWWQJHT-UHFFFAOYSA-N 0.000 claims description 5
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- 208000023958 prostate neoplasm Diseases 0.000 claims description 5
- RWGIDMWSHOFUOC-UHFFFAOYSA-N 4-hydroxy-3-propylbenzaldehyde Chemical compound CCCC1=CC(C=O)=CC=C1O RWGIDMWSHOFUOC-UHFFFAOYSA-N 0.000 claims description 4
- 208000037841 lung tumor Diseases 0.000 claims description 4
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims description 4
- WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 claims description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 3
- SSGODMHQNTWPOX-UHFFFAOYSA-N cyanothiourea Chemical compound NC(=S)NC#N SSGODMHQNTWPOX-UHFFFAOYSA-N 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
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- SOQCZBSZZLWDGU-UHFFFAOYSA-N 3-fluoro-4-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1F SOQCZBSZZLWDGU-UHFFFAOYSA-N 0.000 claims description 2
- CJUSRCPMBVBEDN-UHFFFAOYSA-N [4-amino-2-[4-(pyrrolidin-2-ylmethoxy)anilino]-1,3-thiazol-5-yl]-(3-fluorophenyl)methanone Chemical compound S1C(C(=O)C=2C=C(F)C=CC=2)=C(N)N=C1NC(C=C1)=CC=C1OCC1CCCN1 CJUSRCPMBVBEDN-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 claims 1
- ASBJJBCTLYXARJ-UHFFFAOYSA-N [4-amino-2-(4-pyrrolidin-3-yloxyanilino)-1,3-thiazol-5-yl]-(4-hydroxy-3-propylphenyl)methanone Chemical compound C1=C(O)C(CCC)=CC(C(=O)C2=C(N=C(NC=3C=CC(OC4CNCC4)=CC=3)S2)N)=C1 ASBJJBCTLYXARJ-UHFFFAOYSA-N 0.000 claims 1
- XDYNWZIICVZKBI-UHFFFAOYSA-N [4-amino-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,3-thiazol-5-yl]-(3-fluoro-4-hydroxyphenyl)methanone Chemical compound S1C(C(=O)C=2C=C(F)C(O)=CC=2)=C(N)N=C1NC(C=C1)=CC=C1OCCN1CCCC1 XDYNWZIICVZKBI-UHFFFAOYSA-N 0.000 claims 1
- DTXMTQQZIZGTPO-UHFFFAOYSA-N [4-amino-2-[4-[2-(dimethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(4-hydroxy-3-propylphenyl)methanone Chemical compound C1=C(O)C(CCC)=CC(C(=O)C2=C(N=C(NC=3C=CC(OCCN(C)C)=CC=3)S2)N)=C1 DTXMTQQZIZGTPO-UHFFFAOYSA-N 0.000 claims 1
- KACFBTLJESYLDN-UHFFFAOYSA-N [4-amino-2-[4-[3-(ethylamino)propoxy]anilino]-1,3-thiazol-5-yl]-(3-fluoro-4-methoxyphenyl)methanone Chemical compound C1=CC(OCCCNCC)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(F)C(OC)=CC=2)S1 KACFBTLJESYLDN-UHFFFAOYSA-N 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 154
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 127
- 239000000203 mixture Substances 0.000 description 118
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 102
- 239000000243 solution Substances 0.000 description 94
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 93
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 77
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 62
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 61
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 60
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 52
- 108010025464 Cyclin-Dependent Kinase 4 Proteins 0.000 description 47
- 235000019439 ethyl acetate Nutrition 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
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- 102000013701 Cyclin-Dependent Kinase 4 Human genes 0.000 description 32
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 29
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
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- 229910052794 bromium Inorganic materials 0.000 description 24
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- 239000002904 solvent Substances 0.000 description 22
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 21
- 150000002540 isothiocyanates Chemical class 0.000 description 21
- 239000003921 oil Substances 0.000 description 21
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 21
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 20
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- 229910000104 sodium hydride Inorganic materials 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
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- ITAQNNGDCNFGID-UHFFFAOYSA-N 2-bromo-1-(3-fluorophenyl)ethanone Chemical compound FC1=CC=CC(C(=O)CBr)=C1 ITAQNNGDCNFGID-UHFFFAOYSA-N 0.000 description 14
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- XDJCYKMWJCYQJM-UHFFFAOYSA-N tert-butyl n-(3-hydroxypropyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCCO XDJCYKMWJCYQJM-UHFFFAOYSA-N 0.000 description 1
- MDMWFOJSEVVMBX-UHFFFAOYSA-N tert-butyl n-[2-(4-aminophenoxy)ethyl]-n-ethylcarbamate Chemical compound CC(C)(C)OC(=O)N(CC)CCOC1=CC=C(N)C=C1 MDMWFOJSEVVMBX-UHFFFAOYSA-N 0.000 description 1
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- GVGTWZWYMNBHJK-UHFFFAOYSA-N tert-butyl n-[3-(4-aminophenoxy)propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCOC1=CC=C(N)C=C1 GVGTWZWYMNBHJK-UHFFFAOYSA-N 0.000 description 1
- ATDJDNJDHRCBGN-UHFFFAOYSA-N tert-butyl n-[3-(4-isothiocyanatophenoxy)propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCOC1=CC=C(N=C=S)C=C1 ATDJDNJDHRCBGN-UHFFFAOYSA-N 0.000 description 1
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- SFLXUZPXEWWQNH-UHFFFAOYSA-K tetrabutylazanium;tribromide Chemical compound [Br-].[Br-].[Br-].CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC SFLXUZPXEWWQNH-UHFFFAOYSA-K 0.000 description 1
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Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- 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
- C07D417/12—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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38151302P | 2002-05-17 | 2002-05-17 | |
| US60/381,513 | 2002-05-17 | ||
| PCT/EP2003/004939 WO2003097048A1 (en) | 2002-05-17 | 2003-05-12 | Diaminothiazoles |
Publications (2)
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|---|---|
| AU2003232754A1 AU2003232754A1 (en) | 2003-12-02 |
| AU2003232754B2 true AU2003232754B2 (en) | 2009-03-12 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2003232754A Ceased AU2003232754B2 (en) | 2002-05-17 | 2003-05-12 | Diaminothiazoles |
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|---|---|
| US (1) | US6818663B2 (enExample) |
| EP (1) | EP1507530B1 (enExample) |
| JP (1) | JP4308133B2 (enExample) |
| KR (1) | KR100619515B1 (enExample) |
| CN (1) | CN100400041C (enExample) |
| AR (1) | AR040078A1 (enExample) |
| AT (1) | ATE308323T1 (enExample) |
| AU (1) | AU2003232754B2 (enExample) |
| BR (1) | BR0310081A (enExample) |
| CA (1) | CA2485367A1 (enExample) |
| DE (1) | DE60302152T2 (enExample) |
| ES (1) | ES2251697T3 (enExample) |
| MX (1) | MXPA04011372A (enExample) |
| PL (1) | PL374581A1 (enExample) |
| RU (1) | RU2311414C2 (enExample) |
| WO (1) | WO2003097048A1 (enExample) |
Families Citing this family (16)
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|---|---|---|---|---|
| CA2550891A1 (en) * | 2003-12-24 | 2005-07-14 | Bayer Cropscience Gmbh | Plant growth regulation |
| US7211576B2 (en) * | 2004-04-20 | 2007-05-01 | Hoffmann-La Roche Inc. | Diaminothiazoles |
| US7405220B2 (en) | 2004-06-09 | 2008-07-29 | Hoffmann-La Roche Inc. | Pyrazolopyrimidines |
| US7705009B2 (en) * | 2005-11-22 | 2010-04-27 | Hoffman-La Roche Inc. | 4-aminopyrimidine-5-thione derivatives |
| EP2078003B1 (en) | 2006-10-31 | 2017-03-08 | Merck Sharp & Dohme Corp. | Anilinopiperazine derivatives and methods of use thereof |
| PE20080928A1 (es) | 2006-10-31 | 2008-08-15 | Schering Corp | Derivados de anilinopiperazina como inhibidores de proteina quinasa |
| JP5270758B2 (ja) * | 2008-08-12 | 2013-08-21 | エア プロダクツ アンド ケミカルズ インコーポレイテッド | パー（フェニルエチニル）アレーン誘導体を含有するポリマー組成物 |
| WO2012027481A1 (en) * | 2010-08-24 | 2012-03-01 | Gtx, Inc. | Compounds for treatment of cancer |
| EP2780392B1 (en) | 2011-11-18 | 2016-06-29 | Greene, Tweed & Co. | Crosslinking compounds for high glass transition temperature polymers |
| WO2014172479A1 (en) | 2013-04-16 | 2014-10-23 | Memorial Sloan-Kettering Cancer Center | Companion diagnostic for cdk4 inhibitors |
| WO2015051525A1 (en) * | 2013-10-11 | 2015-04-16 | Rhodia Operations | Synthesis of acetal/ketal |
| WO2017156263A1 (en) | 2016-03-09 | 2017-09-14 | Memorial Sloan-Kettering Cancer Center | Enigma and cdh18 as companion diagnostics for cdk4 inhibitors |
| WO2017158147A1 (en) | 2016-03-18 | 2017-09-21 | Savira Pharmaceuticals Gmbh | Pyrimidone derivatives and their use in the treatment, amelioration or prevention of a viral disease |
| WO2018089902A1 (en) * | 2016-11-13 | 2018-05-17 | Apogee Biotechnology Corporation | Diaminothiazole compounds, compositions and methods of use |
| CN110950848B (zh) * | 2018-09-27 | 2024-03-26 | 徐诺药业 | 新型氨基吡唑类衍生物的合成与应用 |
| JP2022530241A (ja) | 2019-04-30 | 2022-06-28 | インスチトゥート デ メディシーナ モリクラール ジョアン ロボ アントゥネス | Ｃｄｋ阻害剤と組み合わせたｒａｎｋ経路阻害剤 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999021845A2 (en) * | 1997-10-27 | 1999-05-06 | Agouron Pharmaceuticals, Inc. | 4-aminothiazole derivatives, their preparation and their use as inhibitors of cyclin-dependent kinases |
| WO2002012250A2 (en) * | 2000-08-09 | 2002-02-14 | Agouron Pharmaceuticals, Inc. | Pyrazole-thiazole compounds, pharmaceutical compositions containing them, and methods of their use for inhibiting cyclin-dependent kinases |
| WO2002057261A2 (en) * | 2001-01-22 | 2002-07-25 | F. Hoffmann-La Roche Ag | Diaminothiazoles and their use as inhibitors of cyclin-dependent kinase |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2714059B1 (fr) * | 1993-12-21 | 1996-03-08 | Sanofi Elf | Dérivés amino ramifiés du thiazole, leurs procédés de préparation et les compositions pharmaceutiques qui les contiennent. |
| UA71971C2 (en) * | 1999-06-04 | 2005-01-17 | Agoron Pharmaceuticals Inc | Diaminothiazoles, composition based thereon, a method for modulation of protein kinases activity, a method for the treatment of diseases mediated by protein kinases |
-
2003
- 2003-05-05 US US10/429,551 patent/US6818663B2/en not_active Expired - Fee Related
- 2003-05-12 JP JP2004505047A patent/JP4308133B2/ja not_active Expired - Fee Related
- 2003-05-12 EP EP03752731A patent/EP1507530B1/en not_active Expired - Lifetime
- 2003-05-12 RU RU2004137110/04A patent/RU2311414C2/ru active
- 2003-05-12 DE DE60302152T patent/DE60302152T2/de not_active Expired - Fee Related
- 2003-05-12 KR KR1020047018605A patent/KR100619515B1/ko not_active Expired - Fee Related
- 2003-05-12 CA CA002485367A patent/CA2485367A1/en not_active Abandoned
- 2003-05-12 AT AT03752731T patent/ATE308323T1/de not_active IP Right Cessation
- 2003-05-12 MX MXPA04011372A patent/MXPA04011372A/es active IP Right Grant
- 2003-05-12 WO PCT/EP2003/004939 patent/WO2003097048A1/en not_active Ceased
- 2003-05-12 BR BR0310081-2A patent/BR0310081A/pt not_active IP Right Cessation
- 2003-05-12 CN CNB038111314A patent/CN100400041C/zh not_active Expired - Fee Related
- 2003-05-12 AU AU2003232754A patent/AU2003232754B2/en not_active Ceased
- 2003-05-12 ES ES03752731T patent/ES2251697T3/es not_active Expired - Lifetime
- 2003-05-12 PL PL03374581A patent/PL374581A1/xx not_active Application Discontinuation
- 2003-05-15 AR ARP030101692A patent/AR040078A1/es not_active Application Discontinuation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999021845A2 (en) * | 1997-10-27 | 1999-05-06 | Agouron Pharmaceuticals, Inc. | 4-aminothiazole derivatives, their preparation and their use as inhibitors of cyclin-dependent kinases |
| WO2002012250A2 (en) * | 2000-08-09 | 2002-02-14 | Agouron Pharmaceuticals, Inc. | Pyrazole-thiazole compounds, pharmaceutical compositions containing them, and methods of their use for inhibiting cyclin-dependent kinases |
| WO2002057261A2 (en) * | 2001-01-22 | 2002-07-25 | F. Hoffmann-La Roche Ag | Diaminothiazoles and their use as inhibitors of cyclin-dependent kinase |
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA04011372A (es) | 2005-08-15 |
| ATE308323T1 (de) | 2005-11-15 |
| KR100619515B1 (ko) | 2006-09-08 |
| PL374581A1 (en) | 2005-10-31 |
| RU2004137110A (ru) | 2005-08-20 |
| US20040006058A1 (en) | 2004-01-08 |
| BR0310081A (pt) | 2005-02-15 |
| CA2485367A1 (en) | 2003-11-27 |
| AU2003232754A1 (en) | 2003-12-02 |
| CN100400041C (zh) | 2008-07-09 |
| AR040078A1 (es) | 2005-03-16 |
| US6818663B2 (en) | 2004-11-16 |
| KR20050006261A (ko) | 2005-01-15 |
| EP1507530B1 (en) | 2005-11-02 |
| DE60302152D1 (de) | 2005-12-08 |
| DE60302152T2 (de) | 2006-07-13 |
| WO2003097048A1 (en) | 2003-11-27 |
| ES2251697T3 (es) | 2006-05-01 |
| CN1652780A (zh) | 2005-08-10 |
| JP2005530783A (ja) | 2005-10-13 |
| JP4308133B2 (ja) | 2009-08-05 |
| RU2311414C2 (ru) | 2007-11-27 |
| EP1507530A1 (en) | 2005-02-23 |
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