KR20030036862A - 시클린 의존성 키나아제 억제용 조성물 - Google Patents
시클린 의존성 키나아제 억제용 조성물 Download PDFInfo
- Publication number
- KR20030036862A KR20030036862A KR10-2003-7004561A KR20037004561A KR20030036862A KR 20030036862 A KR20030036862 A KR 20030036862A KR 20037004561 A KR20037004561 A KR 20037004561A KR 20030036862 A KR20030036862 A KR 20030036862A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- composition
- cycloalkyl
- formula
- heteroaryl
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 77
- 230000002401 inhibitory effect Effects 0.000 title claims description 18
- 102000003903 Cyclin-dependent kinases Human genes 0.000 title claims description 8
- 108090000266 Cyclin-dependent kinases Proteins 0.000 title claims description 8
- 108091007914 CDKs Proteins 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 87
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 54
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 34
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 24
- 125000003118 aryl group Chemical group 0.000 claims abstract description 20
- 239000001257 hydrogen Substances 0.000 claims abstract description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 18
- 238000011282 treatment Methods 0.000 claims abstract description 18
- 201000010099 disease Diseases 0.000 claims abstract description 17
- 201000011510 cancer Diseases 0.000 claims abstract description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 15
- 230000002062 proliferating effect Effects 0.000 claims abstract description 10
- 206010003246 arthritis Diseases 0.000 claims abstract description 9
- 102000001253 Protein Kinase Human genes 0.000 claims abstract description 8
- 108060006633 protein kinase Proteins 0.000 claims abstract description 8
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 6
- 206010061218 Inflammation Diseases 0.000 claims abstract description 6
- 239000011737 fluorine Substances 0.000 claims abstract description 6
- 230000004054 inflammatory process Effects 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 4
- 230000005764 inhibitory process Effects 0.000 claims abstract description 4
- 239000004480 active ingredient Substances 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 101150012716 CDK1 gene Proteins 0.000 claims description 11
- 101100059559 Emericella nidulans (strain FGSC A4 / ATCC 38163 / CBS 112.46 / NRRL 194 / M139) nimX gene Proteins 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 101100273808 Xenopus laevis cdk1-b gene Proteins 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 101100005789 Caenorhabditis elegans cdk-4 gene Proteins 0.000 claims description 7
- 239000002246 antineoplastic agent Substances 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 208000031888 Mycoses Diseases 0.000 claims description 6
- 230000001093 anti-cancer Effects 0.000 claims description 6
- 101150073031 cdk2 gene Proteins 0.000 claims description 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 6
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 6
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 6
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 5
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 230000004770 neurodegeneration Effects 0.000 claims description 4
- 101150053721 Cdk5 gene Proteins 0.000 claims description 3
- 206010017533 Fungal infection Diseases 0.000 claims description 3
- 206010052779 Transplant rejections Diseases 0.000 claims description 3
- 208000036142 Viral infection Diseases 0.000 claims description 3
- 230000009385 viral infection Effects 0.000 claims description 3
- 208000030507 AIDS Diseases 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 238000011161 development Methods 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims 5
- 101150090188 Cdk8 gene Proteins 0.000 claims 2
- 101150112625 SSN3 gene Proteins 0.000 claims 2
- 101100150415 Schizosaccharomyces pombe (strain 972 / ATCC 24843) srb10 gene Proteins 0.000 claims 2
- 238000011394 anticancer treatment Methods 0.000 claims 2
- 101150059448 cdk7 gene Proteins 0.000 claims 2
- 238000002512 chemotherapy Methods 0.000 claims 1
- 239000012829 chemotherapy agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 129
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 54
- -1 Carboxylate anions Chemical class 0.000 description 49
- 239000000243 solution Substances 0.000 description 49
- 239000002904 solvent Substances 0.000 description 38
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- 238000002360 preparation method Methods 0.000 description 33
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 229920005989 resin Polymers 0.000 description 25
- 239000011347 resin Substances 0.000 description 25
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 23
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 20
- 239000007787 solid Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 16
- 150000003573 thiols Chemical class 0.000 description 15
- 238000004128 high performance liquid chromatography Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 108091000080 Phosphotransferase Proteins 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 235000019439 ethyl acetate Nutrition 0.000 description 11
- 230000014759 maintenance of location Effects 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 102000020233 phosphotransferase Human genes 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 229910052786 argon Inorganic materials 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 229940086542 triethylamine Drugs 0.000 description 10
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 229910052736 halogen Inorganic materials 0.000 description 9
- 150000002367 halogens Chemical class 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- 150000002431 hydrogen Chemical class 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 8
- 239000003814 drug Substances 0.000 description 7
- 238000003818 flash chromatography Methods 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 229920001367 Merrifield resin Polymers 0.000 description 6
- 229910004298 SiO 2 Inorganic materials 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 6
- 229910052796 boron Inorganic materials 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 230000004663 cell proliferation Effects 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- HFSUOEOQZXTYLK-UHFFFAOYSA-N 5-[(5-ethyl-1,3-oxazol-2-yl)methylsulfanyl]-1,3-thiazol-2-amine Chemical compound O1C(CC)=CN=C1CSC1=CN=C(N)S1 HFSUOEOQZXTYLK-UHFFFAOYSA-N 0.000 description 4
- 208000024827 Alzheimer disease Diseases 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 108010058546 Cyclin D1 Proteins 0.000 description 4
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 4
- 102100024165 G1/S-specific cyclin-D1 Human genes 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- CPWJSEMCTUPCRN-UHFFFAOYSA-N [2-[(2,2,2-trifluoroacetyl)amino]-1,3-thiazol-5-yl] thiocyanate Chemical compound FC(F)(F)C(=O)NC1=NC=C(SC#N)S1 CPWJSEMCTUPCRN-UHFFFAOYSA-N 0.000 description 4
- 230000002159 abnormal effect Effects 0.000 description 4
- 230000006907 apoptotic process Effects 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 239000002254 cytotoxic agent Substances 0.000 description 4
- 229940127089 cytotoxic agent Drugs 0.000 description 4
- 231100000599 cytotoxic agent Toxicity 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 230000002265 prevention Effects 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- 241000701447 unidentified baculovirus Species 0.000 description 4
- QHHQYUYWCFYKRB-UHFFFAOYSA-N (2-acetamido-1,3-thiazol-5-yl) thiocyanate Chemical compound CC(=O)NC1=NC=C(SC#N)S1 QHHQYUYWCFYKRB-UHFFFAOYSA-N 0.000 description 3
- HUMARXMRTXDPPK-UHFFFAOYSA-N (2-amino-1,3-thiazol-5-yl) thiocyanate Chemical compound NC1=NC=C(SC#N)S1 HUMARXMRTXDPPK-UHFFFAOYSA-N 0.000 description 3
- IMBUVEMJUKQLQA-UHFFFAOYSA-N 1-diazonio-3,3-dimethylbut-1-en-2-olate Chemical compound CC(C)(C)C(=O)C=[N+]=[N-] IMBUVEMJUKQLQA-UHFFFAOYSA-N 0.000 description 3
- NHZSHQIXZMFQDC-UHFFFAOYSA-N 2-(bromomethyl)-4,5-dimethyl-1,3-oxazole Chemical compound CC=1N=C(CBr)OC=1C NHZSHQIXZMFQDC-UHFFFAOYSA-N 0.000 description 3
- PFVJIYLUKRACDJ-UHFFFAOYSA-N 2-(chloromethyl)-4-ethyl-1,3-oxazole Chemical compound CCC1=COC(CCl)=N1 PFVJIYLUKRACDJ-UHFFFAOYSA-N 0.000 description 3
- NEXUFDMRFRDMPB-UHFFFAOYSA-N 2-chloro-n-(1-hydroxybutan-2-yl)acetamide Chemical compound CCC(CO)NC(=O)CCl NEXUFDMRFRDMPB-UHFFFAOYSA-N 0.000 description 3
- 201000001320 Atherosclerosis Diseases 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 208000024172 Cardiovascular disease Diseases 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 108010060385 Cyclin B1 Proteins 0.000 description 3
- 102100032340 G2/mitotic-specific cyclin-B1 Human genes 0.000 description 3
- 206010018364 Glomerulonephritis Diseases 0.000 description 3
- 206010025323 Lymphomas Diseases 0.000 description 3
- 201000004681 Psoriasis Diseases 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- JETOHQYQAQUXKK-UHFFFAOYSA-N benzyl n-(2-hydroxybutyl)carbamate Chemical compound CCC(O)CNC(=O)OCC1=CC=CC=C1 JETOHQYQAQUXKK-UHFFFAOYSA-N 0.000 description 3
- GQXXEURLDOMPBM-UHFFFAOYSA-N benzyl n-(2-oxobutyl)carbamate Chemical compound CCC(=O)CNC(=O)OCC1=CC=CC=C1 GQXXEURLDOMPBM-UHFFFAOYSA-N 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 208000032839 leukemia Diseases 0.000 description 3
- 238000012544 monitoring process Methods 0.000 description 3
- NRCIGJZLDFFIDD-UHFFFAOYSA-N n-[5-[(5-ethyl-1,3-oxazol-2-yl)methylsulfanyl]-1,3-thiazol-2-yl]acetamide Chemical compound O1C(CC)=CN=C1CSC1=CN=C(NC(C)=O)S1 NRCIGJZLDFFIDD-UHFFFAOYSA-N 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 210000000278 spinal cord Anatomy 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 230000003612 virological effect Effects 0.000 description 3
- APHZQLYNFVRAID-UHFFFAOYSA-N (1,3-thiazol-5-ylamino) thiocyanate Chemical compound N#CSNC1=CN=CS1 APHZQLYNFVRAID-UHFFFAOYSA-N 0.000 description 2
- QCWWEZIJUCPALZ-UHFFFAOYSA-N 1-aminobutan-2-one Chemical compound CCC(=O)CN QCWWEZIJUCPALZ-UHFFFAOYSA-N 0.000 description 2
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 2
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
- ZCHCHJQEWYIJDQ-UHFFFAOYSA-N 2-methyl-1,3-oxazole Chemical group CC1=NC=CO1 ZCHCHJQEWYIJDQ-UHFFFAOYSA-N 0.000 description 2
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 2
- WBIZZNFQJPOKDK-UHFFFAOYSA-N 4-hydroxy-2-methoxybenzaldehyde Chemical compound COC1=CC(O)=CC=C1C=O WBIZZNFQJPOKDK-UHFFFAOYSA-N 0.000 description 2
- LUGZUJZYTRPEDY-UHFFFAOYSA-N 5-tert-butyl-2-(chloromethyl)-1,3-oxazole Chemical compound CC(C)(C)C1=CN=C(CCl)O1 LUGZUJZYTRPEDY-UHFFFAOYSA-N 0.000 description 2
- 208000032467 Aplastic anaemia Diseases 0.000 description 2
- 208000023275 Autoimmune disease Diseases 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- 201000009030 Carcinoma Diseases 0.000 description 2
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 2
- 102000003909 Cyclin E Human genes 0.000 description 2
- 108090000257 Cyclin E Proteins 0.000 description 2
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 2
- 206010058314 Dysplasia Diseases 0.000 description 2
- 108010033040 Histones Proteins 0.000 description 2
- 241000701044 Human gammaherpesvirus 4 Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 208000009905 Neurofibromatoses Diseases 0.000 description 2
- 102100026379 Neurofibromin Human genes 0.000 description 2
- 101710181008 P protein Proteins 0.000 description 2
- 101710177166 Phosphoprotein Proteins 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 208000004403 Prostatic Hyperplasia Diseases 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 108050002653 Retinoblastoma protein Proteins 0.000 description 2
- 206010040070 Septic Shock Diseases 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 2
- ZRLDBDZSLLGDOX-UHFFFAOYSA-N Trimethyloxazole Chemical compound CC1=NC(C)=C(C)O1 ZRLDBDZSLLGDOX-UHFFFAOYSA-N 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 208000026555 breast adenosis Diseases 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 201000005787 hematologic cancer Diseases 0.000 description 2
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 238000000021 kinase assay Methods 0.000 description 2
- JYWSISJKMHOMBG-UHFFFAOYSA-N n-[5-[(4,5-dimethyl-1,3-oxazol-2-yl)methylsulfanyl]-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC=C1SCC1=NC(C)=C(C)O1 JYWSISJKMHOMBG-UHFFFAOYSA-N 0.000 description 2
- DTHXQOFAEWKCPU-UHFFFAOYSA-N n-[5-[(4-ethyl-1,3-oxazol-2-yl)methylsulfanyl]-1,3-thiazol-2-yl]acetamide Chemical compound CCC1=COC(CSC=2SC(NC(C)=O)=NC=2)=N1 DTHXQOFAEWKCPU-UHFFFAOYSA-N 0.000 description 2
- VNAAESWDZCUTMH-UHFFFAOYSA-N n-[5-[(5-ethyl-1,3-oxazol-2-yl)methylsulfanyl]-1,3-thiazol-2-yl]benzamide Chemical compound O1C(CC)=CN=C1CSC(S1)=CN=C1NC(=O)C1=CC=CC=C1 VNAAESWDZCUTMH-UHFFFAOYSA-N 0.000 description 2
- WKTFFSVUCQARKP-UHFFFAOYSA-N n-[5-[(5-tert-butyl-1,3-oxazol-2-yl)methylsulfanyl]-1,3-thiazol-2-yl]-2,2-dimethylpropanamide Chemical compound S1C(NC(=O)C(C)(C)C)=NC=C1SCC1=NC=C(C(C)(C)C)O1 WKTFFSVUCQARKP-UHFFFAOYSA-N 0.000 description 2
- GFXMFSCCEVADLF-UHFFFAOYSA-N n-[5-[(5-tert-butyl-1,3-oxazol-2-yl)methylsulfanyl]-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC=C1SCC1=NC=C(C(C)(C)C)O1 GFXMFSCCEVADLF-UHFFFAOYSA-N 0.000 description 2
- 201000004931 neurofibromatosis Diseases 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- QZRXRMPNCPCMSW-UHFFFAOYSA-N phosphanyl(phosphanylidene)phosphane Chemical compound PP=P QZRXRMPNCPCMSW-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 208000015768 polyposis Diseases 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002953 preparative HPLC Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 208000005069 pulmonary fibrosis Diseases 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000025053 regulation of cell proliferation Effects 0.000 description 2
- 208000037803 restenosis Diseases 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- OYTWNVNHKYTJPG-UHFFFAOYSA-N s-(2-acetamido-1,3-thiazol-5-yl) ethanethioate Chemical compound CC(=O)NC1=NC=C(SC(C)=O)S1 OYTWNVNHKYTJPG-UHFFFAOYSA-N 0.000 description 2
- 230000036573 scar formation Effects 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- HOEMOEJHHVVLJW-UHFFFAOYSA-N tert-butyl 2-[(2-acetamido-1,3-thiazol-5-yl)sulfanyl]acetate Chemical compound CC(=O)NC1=NC=C(SCC(=O)OC(C)(C)C)S1 HOEMOEJHHVVLJW-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 210000001685 thyroid gland Anatomy 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 241000701161 unidentified adenovirus Species 0.000 description 2
- 241001529453 unidentified herpesvirus Species 0.000 description 2
- 238000007631 vascular surgery Methods 0.000 description 2
- 230000024883 vasodilation Effects 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- DBSXNGIBAKYMSS-UHFFFAOYSA-N 1,3-difluoro-2-isothiocyanatobenzene Chemical compound FC1=CC=CC(F)=C1N=C=S DBSXNGIBAKYMSS-UHFFFAOYSA-N 0.000 description 1
- IGHCJQAGPOQQPR-UHFFFAOYSA-N 1,3-thiazol-5-yl thiocyanate Chemical compound N#CSC1=CN=CS1 IGHCJQAGPOQQPR-UHFFFAOYSA-N 0.000 description 1
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
- KODLUXHSIZOKTG-UHFFFAOYSA-N 1-aminobutan-2-ol Chemical compound CCC(O)CN KODLUXHSIZOKTG-UHFFFAOYSA-N 0.000 description 1
- DGSSJZJBCABUMD-UHFFFAOYSA-N 1-aminobutan-2-one;hydrochloride Chemical compound Cl.CCC(=O)CN DGSSJZJBCABUMD-UHFFFAOYSA-N 0.000 description 1
- AAIZGJABVHYYGI-UHFFFAOYSA-N 2-[(2-acetamido-1,3-thiazol-5-yl)sulfanyl]-n-(2-oxobutyl)acetamide Chemical compound CCC(=O)CNC(=O)CSC1=CN=C(NC(C)=O)S1 AAIZGJABVHYYGI-UHFFFAOYSA-N 0.000 description 1
- VUBHPDXNTUPWHT-UHFFFAOYSA-N 2-[(2-acetamido-1,3-thiazol-5-yl)sulfanyl]acetic acid Chemical compound CC(=O)NC1=NC=C(SCC(O)=O)S1 VUBHPDXNTUPWHT-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- ABKIVEMOQGQUJR-UHFFFAOYSA-N 2-[5-[(5-tert-butyl-1,3-oxazol-2-yl)methylsulfanyl]-1,3-thiazol-2-yl]-1-cyano-3-(2,6-difluorophenyl)guanidine Chemical compound O1C(C(C)(C)C)=CN=C1CSC(S1)=CN=C1NC(NC#N)=NC1=C(F)C=CC=C1F ABKIVEMOQGQUJR-UHFFFAOYSA-N 0.000 description 1
- ANHJTFYOEXWQPT-UHFFFAOYSA-N 2-[chloro(fluoro)methyl]-1,3-oxazole Chemical compound ClC(C=1OC=CN1)F ANHJTFYOEXWQPT-UHFFFAOYSA-N 0.000 description 1
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 description 1
- JCBPETKZIGVZRE-UHFFFAOYSA-N 2-aminobutan-1-ol Chemical compound CCC(N)CO JCBPETKZIGVZRE-UHFFFAOYSA-N 0.000 description 1
- ABSYEGWQFLNILN-UHFFFAOYSA-N 2-butyl-1,3-oxazole Chemical compound CCCCC1=NC=CO1 ABSYEGWQFLNILN-UHFFFAOYSA-N 0.000 description 1
- HBAHZZVIEFRTEY-UHFFFAOYSA-N 2-heptylcyclohex-2-en-1-one Chemical compound CCCCCCCC1=CCCCC1=O HBAHZZVIEFRTEY-UHFFFAOYSA-N 0.000 description 1
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- ABFYEILPZWAIBN-UHFFFAOYSA-N 3-(iminomethylideneamino)-n,n-dimethylpropan-1-amine;hydrochloride Chemical compound Cl.CN(C)CCCN=C=N ABFYEILPZWAIBN-UHFFFAOYSA-N 0.000 description 1
- KLAIOABSDQUNSA-WUKNDPDISA-N 3-[(e)-octadec-2-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCCCCCCC\C=C\CC1CC(=O)OC1=O KLAIOABSDQUNSA-WUKNDPDISA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 206010065040 AIDS dementia complex Diseases 0.000 description 1
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 description 1
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 206010003571 Astrocytoma Diseases 0.000 description 1
- 208000003950 B-cell lymphoma Diseases 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 206010005042 Bladder fibrosis Diseases 0.000 description 1
- 101100314454 Caenorhabditis elegans tra-1 gene Proteins 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 208000017897 Carcinoma of esophagus Diseases 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 102000003910 Cyclin D Human genes 0.000 description 1
- 108090000259 Cyclin D Proteins 0.000 description 1
- 102000013701 Cyclin-Dependent Kinase 4 Human genes 0.000 description 1
- 108010025464 Cyclin-Dependent Kinase 4 Proteins 0.000 description 1
- 230000006820 DNA synthesis Effects 0.000 description 1
- 229940123780 DNA topoisomerase I inhibitor Drugs 0.000 description 1
- 229940124087 DNA topoisomerase II inhibitor Drugs 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 102100031480 Dual specificity mitogen-activated protein kinase kinase 1 Human genes 0.000 description 1
- 101710146526 Dual specificity mitogen-activated protein kinase kinase 1 Proteins 0.000 description 1
- 102000001301 EGF receptor Human genes 0.000 description 1
- 108060006698 EGF receptor Proteins 0.000 description 1
- 201000008808 Fibrosarcoma Diseases 0.000 description 1
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 1
- 206010018338 Glioma Diseases 0.000 description 1
- 102000006947 Histones Human genes 0.000 description 1
- 208000017604 Hodgkin disease Diseases 0.000 description 1
- 208000021519 Hodgkin lymphoma Diseases 0.000 description 1
- 208000010747 Hodgkins lymphoma Diseases 0.000 description 1
- 101000599951 Homo sapiens Insulin-like growth factor I Proteins 0.000 description 1
- 241000701806 Human papillomavirus Species 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 102100037852 Insulin-like growth factor I Human genes 0.000 description 1
- 208000007766 Kaposi sarcoma Diseases 0.000 description 1
- 208000008839 Kidney Neoplasms Diseases 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 108091054455 MAP kinase family Proteins 0.000 description 1
- 102000043136 MAP kinase family Human genes 0.000 description 1
- 229940124647 MEK inhibitor Drugs 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- 101001055320 Myxine glutinosa Insulin-like growth factor Proteins 0.000 description 1
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 description 1
- VZUNGTLZRAYYDE-UHFFFAOYSA-N N-methyl-N'-nitro-N-nitrosoguanidine Chemical compound O=NN(C)C(=N)N[N+]([O-])=O VZUNGTLZRAYYDE-UHFFFAOYSA-N 0.000 description 1
- LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 description 1
- PQBAWAQIRZIWIV-UHFFFAOYSA-N N-methylpyridinium Chemical compound C[N+]1=CC=CC=C1 PQBAWAQIRZIWIV-UHFFFAOYSA-N 0.000 description 1
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 1
- 206010029260 Neuroblastoma Diseases 0.000 description 1
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 206010033128 Ovarian cancer Diseases 0.000 description 1
- 108091008606 PDGF receptors Proteins 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 description 1
- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 description 1
- 102000011653 Platelet-Derived Growth Factor Receptors Human genes 0.000 description 1
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 102000003923 Protein Kinase C Human genes 0.000 description 1
- 108090000315 Protein Kinase C Proteins 0.000 description 1
- 102100033479 RAF proto-oncogene serine/threonine-protein kinase Human genes 0.000 description 1
- 101150101372 RAF1 gene Proteins 0.000 description 1
- 230000006819 RNA synthesis Effects 0.000 description 1
- 206010038389 Renal cancer Diseases 0.000 description 1
- 206010063837 Reperfusion injury Diseases 0.000 description 1
- 208000007014 Retinitis pigmentosa Diseases 0.000 description 1
- 201000000582 Retinoblastoma Diseases 0.000 description 1
- 241000580858 Simian-Human immunodeficiency virus Species 0.000 description 1
- 241000710960 Sindbis virus Species 0.000 description 1
- 206010041067 Small cell lung cancer Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- 206010042971 T-cell lymphoma Diseases 0.000 description 1
- 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 description 1
- 208000033781 Thyroid carcinoma Diseases 0.000 description 1
- 208000024770 Thyroid neoplasm Diseases 0.000 description 1
- 239000000365 Topoisomerase I Inhibitor Substances 0.000 description 1
- 239000000317 Topoisomerase II Inhibitor Substances 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 230000010721 Tubulin Interactions Effects 0.000 description 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
- 101100102932 Xenopus laevis wee2-b gene Proteins 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- FADXNBTXGBBRNJ-UHFFFAOYSA-N [(2,2,2-trifluoroacetyl)amino] thiocyanate Chemical compound FC(F)(F)C(=O)NSC#N FADXNBTXGBBRNJ-UHFFFAOYSA-N 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 1
- 125000005213 alkyl heteroaryl group Chemical group 0.000 description 1
- 125000005189 alkyl hydroxy group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229950003476 aminothiazole Drugs 0.000 description 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 230000033115 angiogenesis Effects 0.000 description 1
- 229940124650 anti-cancer therapies Drugs 0.000 description 1
- 230000000340 anti-metabolite Effects 0.000 description 1
- 238000011319 anticancer therapy Methods 0.000 description 1
- 229940100197 antimetabolite Drugs 0.000 description 1
- 239000002256 antimetabolite Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004601 benzofurazanyl group Chemical group N1=C2C(=NO1)C(=CC=C2)* 0.000 description 1
- 125000005872 benzooxazolyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
- 201000000053 blastoma Diseases 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 208000025434 cerebellar degeneration Diseases 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000002113 chemopreventative effect Effects 0.000 description 1
- 238000010568 chiral column chromatography Methods 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000004803 chlorobenzyl group Chemical group 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
- 229960004316 cisplatin Drugs 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940126142 compound 16 Drugs 0.000 description 1
- 229940126086 compound 21 Drugs 0.000 description 1
- 229940126208 compound 22 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000000824 cytostatic agent Substances 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XXTZHYXQVWRADW-UHFFFAOYSA-N diazomethanone Chemical compound [N]N=C=O XXTZHYXQVWRADW-UHFFFAOYSA-N 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 229960003668 docetaxel Drugs 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960004679 doxorubicin Drugs 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 238000003255 drug test Methods 0.000 description 1
- 201000008184 embryoma Diseases 0.000 description 1
- 229930013356 epothilone Natural products 0.000 description 1
- HESCAJZNRMSMJG-KKQRBIROSA-N epothilone A Chemical class C/C([C@@H]1C[C@@H]2O[C@@H]2CCC[C@@H]([C@@H]([C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1)O)C)=C\C1=CSC(C)=N1 HESCAJZNRMSMJG-KKQRBIROSA-N 0.000 description 1
- 210000003238 esophagus Anatomy 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 description 1
- 229960005420 etoposide Drugs 0.000 description 1
- 208000021045 exocrine pancreatic carcinoma Diseases 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229960002949 fluorouracil Drugs 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 210000000232 gallbladder Anatomy 0.000 description 1
- 201000010175 gallbladder cancer Diseases 0.000 description 1
- 201000007487 gallbladder carcinoma Diseases 0.000 description 1
- 206010017758 gastric cancer Diseases 0.000 description 1
- 208000010749 gastric carcinoma Diseases 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 210000003780 hair follicle Anatomy 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940125697 hormonal agent Drugs 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- KLEAIHJJLUAXIQ-JDRGBKBRSA-N irinotecan hydrochloride hydrate Chemical compound O.O.O.Cl.C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 KLEAIHJJLUAXIQ-JDRGBKBRSA-N 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 201000010982 kidney cancer Diseases 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 201000005296 lung carcinoma Diseases 0.000 description 1
- 206010025135 lupus erythematosus Diseases 0.000 description 1
- 230000000492 lymphangiogenic effect Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
- 230000009401 metastasis Effects 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 238000002703 mutagenesis Methods 0.000 description 1
- 231100000350 mutagenesis Toxicity 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 208000007538 neurilemmoma Diseases 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 201000008968 osteosarcoma Diseases 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- 239000008196 pharmacological composition Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 201000001514 prostate carcinoma Diseases 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- PFZCOWLKXHIVII-UHFFFAOYSA-N pyridin-1-ium-1-amine Chemical compound N[N+]1=CC=CC=C1 PFZCOWLKXHIVII-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical class [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- CCOXWRVWKFVFDG-UHFFFAOYSA-N pyrimidine-2-carbaldehyde Chemical compound O=CC1=NC=CC=N1 CCOXWRVWKFVFDG-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 208000023134 retinal cell neoplasm Diseases 0.000 description 1
- 201000009410 rhabdomyosarcoma Diseases 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 201000009890 sinusitis Diseases 0.000 description 1
- 201000000849 skin cancer Diseases 0.000 description 1
- 201000008261 skin carcinoma Diseases 0.000 description 1
- 208000000587 small cell lung carcinoma Diseases 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 208000002320 spinal muscular atrophy Diseases 0.000 description 1
- 206010041823 squamous cell carcinoma Diseases 0.000 description 1
- 102000009076 src-Family Kinases Human genes 0.000 description 1
- 108010087686 src-Family Kinases Proteins 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 201000000498 stomach carcinoma Diseases 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 229960001603 tamoxifen Drugs 0.000 description 1
- 102000013498 tau Proteins Human genes 0.000 description 1
- 108010026424 tau Proteins Proteins 0.000 description 1
- 208000001608 teratocarcinoma Diseases 0.000 description 1
- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000003734 thymidylate synthase inhibitor Substances 0.000 description 1
- 201000002510 thyroid cancer Diseases 0.000 description 1
- 208000013077 thyroid gland carcinoma Diseases 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 229960000303 topotecan Drugs 0.000 description 1
- UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
- 208000012991 uterine carcinoma Diseases 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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
- C07D417/14—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
- 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
- C07D277/54—Nitrogen and either oxygen or sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- 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
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Immunology (AREA)
- Biomedical Technology (AREA)
- Communicable Diseases (AREA)
- Cardiology (AREA)
- Virology (AREA)
- Oncology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Dermatology (AREA)
- Rheumatology (AREA)
- Transplantation (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Molecular Biology (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6519597P | 1997-11-12 | 1997-11-12 | |
| US60/065,195 | 1997-11-12 | ||
| PCT/US1998/023197 WO1999024416A1 (en) | 1997-11-12 | 1998-11-02 | Aminothiazole inhibitors of cyclin dependent kinases |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR10-2000-7004995A Division KR100454426B1 (ko) | 1997-11-12 | 1998-11-02 | 시클린 의존성 키나아제의 아미노티아졸 억제제 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20030036862A true KR20030036862A (ko) | 2003-05-09 |
Family
ID=22060972
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR10-2003-7004561A Ceased KR20030036862A (ko) | 1997-11-12 | 1998-11-02 | 시클린 의존성 키나아제 억제용 조성물 |
| KR10-2000-7004995A Expired - Fee Related KR100454426B1 (ko) | 1997-11-12 | 1998-11-02 | 시클린 의존성 키나아제의 아미노티아졸 억제제 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR10-2000-7004995A Expired - Fee Related KR100454426B1 (ko) | 1997-11-12 | 1998-11-02 | 시클린 의존성 키나아제의 아미노티아졸 억제제 |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US6040321A (enExample) |
| EP (1) | EP1042307B1 (enExample) |
| JP (1) | JP4344084B2 (enExample) |
| KR (2) | KR20030036862A (enExample) |
| CN (1) | CN1160343C (enExample) |
| AR (1) | AR017182A1 (enExample) |
| AT (1) | ATE374771T1 (enExample) |
| AU (1) | AU730607B2 (enExample) |
| BR (1) | BR9814124A (enExample) |
| CA (1) | CA2309551C (enExample) |
| CO (1) | CO4990957A1 (enExample) |
| CY (1) | CY1107509T1 (enExample) |
| CZ (1) | CZ297907B6 (enExample) |
| DE (1) | DE69838515T2 (enExample) |
| DK (1) | DK1042307T3 (enExample) |
| EG (1) | EG24028A (enExample) |
| ES (1) | ES2296347T3 (enExample) |
| HU (1) | HUP0004559A3 (enExample) |
| ID (1) | ID23983A (enExample) |
| IL (1) | IL135589A (enExample) |
| MY (1) | MY120779A (enExample) |
| NO (1) | NO316773B1 (enExample) |
| NZ (1) | NZ503828A (enExample) |
| PE (1) | PE131699A1 (enExample) |
| PL (1) | PL204642B1 (enExample) |
| PT (1) | PT1042307E (enExample) |
| RU (1) | RU2211839C2 (enExample) |
| TR (1) | TR200001344T2 (enExample) |
| TW (1) | TW593292B (enExample) |
| UY (1) | UY25239A1 (enExample) |
| WO (1) | WO1999024416A1 (enExample) |
| ZA (1) | ZA9810332B (enExample) |
Families Citing this family (111)
| 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 |
| US6214852B1 (en) * | 1998-10-21 | 2001-04-10 | Bristol-Myers Squibb Company | N-[5-[[[5-alkyl-2-oxazolyl]methyl]thio]-2-thiazolyl]-carboxamide inhibitors of cyclin dependent kinases |
| US6414156B2 (en) | 1998-10-21 | 2002-07-02 | Bristol-Myers Squibb Company | Process for preparing azacycloalkanoylaminothiazoles |
| WO2000035455A1 (en) * | 1998-12-15 | 2000-06-22 | Telik, Inc. | Heteroaryl-aryl ureas as igf-1 receptor antagonists |
| US20040171632A1 (en) * | 1998-12-22 | 2004-09-02 | Gowan Richard Carleton | Combination chemotherapy |
| DE69928568T2 (de) * | 1998-12-22 | 2006-07-27 | Warner-Lambert Co. Llc | Chemotheriapie mit einem antimitotischen mittel und einem mek inhibitor |
| KR20010112408A (ko) * | 1999-04-07 | 2001-12-20 | 모리타 다카카즈 | Ｎ-치환되고-Ｎ'-치환된 우레아 유도체 및 ＴＮＦ-α 생성억제제로서의 그의 용도 |
| EP1169038B9 (en) | 1999-04-15 | 2013-07-10 | Bristol-Myers Squibb Company | Cyclic protein tyrosine kinase inhibitors |
| US7125875B2 (en) | 1999-04-15 | 2006-10-24 | Bristol-Myers Squibb Company | Cyclic protein tyrosine kinase inhibitors |
| 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 |
| WO2001007411A1 (en) * | 1999-07-26 | 2001-02-01 | Banyu Pharmaceutical Co., Ltd. | Biarylurea derivatives |
| US6114365A (en) * | 1999-08-12 | 2000-09-05 | Pharmacia & Upjohn S.P.A. | Arylmethyl-carbonylamino-thiazole derivatives, process for their preparation, and their use as antitumor agents |
| MY125768A (en) * | 1999-12-15 | 2006-08-30 | Bristol Myers Squibb Co | N-[5-[[[5-alkyl-2-oxazolyl]methyl]thio]-2-thiazolyl]-carboxamide inhibitors of cyclin dependent kinases |
| 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 |
| YU54202A (sh) | 2000-01-18 | 2006-01-16 | Agouron Pharmaceuticals Inc. | Jedinjenja indazola, farmaceutske smeše i postupci za stimulisanje i inhibiranje ćelijske proliferacije |
| HN2001000008A (es) | 2000-01-21 | 2003-12-11 | Inc Agouron Pharmaceuticals | Compuesto de amida y composiciones farmaceuticas para inhibir proteinquinasas, y su modo de empleo |
| AU2001230026A1 (en) * | 2000-02-04 | 2001-08-14 | Novo-Nordisk A/S | 2,4-diaminothiazole derivatives |
| IT1317826B1 (it) * | 2000-02-11 | 2003-07-15 | Dompe Spa | Ammidi, utili nell'inibizione della chemiotassi dei neutrofiliindotta da il-8. |
| CA2398446A1 (en) | 2000-04-18 | 2001-10-25 | Agouron Pharmaceuticals, Inc. | Pyrazoles for inhibiting protein kinases |
| US6534531B2 (en) * | 2000-04-27 | 2003-03-18 | Bristol-Myers Squibb Company | Methods for preventing and treating alopecia induced by chemotherapy or radiotherapy |
| AU2001264376A1 (en) * | 2000-06-15 | 2001-12-24 | Chaconne Nsi Co., Ltd. | Urea derivative useful as an anti-cancer agent and process for preparing same |
| PL365170A1 (en) * | 2000-07-26 | 2004-12-27 | Bristol-Myers Squibb Company | N-[5-[[[5-alkyl-2-oxazolyl]methyl]thio]-2-thiazolyl] carboxamide 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 |
| US20020173507A1 (en) * | 2000-08-15 | 2002-11-21 | Vincent Santora | Urea compounds and methods of uses |
| US6645990B2 (en) | 2000-08-15 | 2003-11-11 | Amgen Inc. | Thiazolyl urea compounds and methods of uses |
| AU3113902A (en) | 2000-12-21 | 2002-07-01 | Bristol Myers Squibb Co | Thiazolyl inhibitors of tec family tyrosine kinases |
| US6756374B2 (en) | 2001-01-22 | 2004-06-29 | Hoffmann-La Roche Inc. | Diaminothiazoles having antiproliferative activity |
| BRPI0206509B8 (pt) | 2001-01-25 | 2021-05-25 | R Pharm Us Operating Llc | processo para formular, para administração parenteral, um análogo de epotilona, preparação farmacêutica, processo para formar uma composição farmacêutica para administração parental, composição farmacêutica e uso de um análogo de epotilona na preparação de uma composição farmacêutica para o tratamento de câncer |
| JP2004519493A (ja) * | 2001-03-19 | 2004-07-02 | ノバルティス アクチエンゲゼルシャフト | 抗下痢剤およびエポチロンまたはエポチロン誘導体を含む組合せ剤 |
| DE60208630T2 (de) | 2001-05-11 | 2006-08-17 | Pfizer Products Inc., Groton | Thiazolderivate und ihre Verwendung als cdk-Inhibitoren |
| EP1721609A3 (en) * | 2001-05-16 | 2007-01-31 | GPC Biotech AG | Pyridylpyrimidine derivatives as effective compounds against prion diseases |
| CA2447475A1 (en) | 2001-05-25 | 2002-12-05 | Chu-Biao Xue | Hydantion derivatives as inhibitors of matrix metalloproteinases |
| HN2002000156A (es) | 2001-07-06 | 2003-11-27 | Inc Agouron Pharmaceuticals | Derivados de benzamida tiazol y composiciones farmaceuticas para inhibir la proliferacion de celulas y metodos para su utilización. |
| NZ530524A (en) * | 2001-07-19 | 2006-12-22 | Pharmacia Italia S | Phenylacetamido-thiazole derivatives, process for their preparation and their use as antitumor agents |
| EE200400074A (et) * | 2001-08-31 | 2004-06-15 | Bristol-Myers Squibb Company | Koostised ning nende kasutamine proliferatiivsetehaiguste raviks |
| US7405234B2 (en) * | 2002-05-17 | 2008-07-29 | Bristol-Myers Squibb Company | Bicyclic modulators of androgen receptor function |
| TW200401638A (en) * | 2002-06-20 | 2004-02-01 | Bristol Myers Squibb Co | Heterocyclic inhibitors of kinases |
| EP1531815B1 (en) | 2002-06-27 | 2014-09-24 | Novo Nordisk A/S | Glucokinase activators |
| US7196078B2 (en) * | 2002-09-04 | 2007-03-27 | Schering Corpoartion | Trisubstituted and tetrasubstituted pyrazolopyrimidines as cyclin dependent kinase inhibitors |
| WO2004022062A1 (en) * | 2002-09-04 | 2004-03-18 | Schering Corporation | Pyrazolopyrimidines as cyclin dependent kinase inhibitors |
| US7205308B2 (en) * | 2002-09-04 | 2007-04-17 | Schering Corporation | Trisubstituted 7-aminopyrazolopyrimidines as cyclin dependent kinase inhibitors |
| US7119200B2 (en) | 2002-09-04 | 2006-10-10 | Schering Corporation | Pyrazolopyrimidines as cyclin dependent kinase inhibitors |
| CA2497444C (en) * | 2002-09-04 | 2010-11-30 | Schering Corporation | Pyrazolopyrimidines as cyclin dependent kinase inhibitors |
| US7074924B2 (en) * | 2002-09-04 | 2006-07-11 | Schering Corporation | Pyrazolopyrimidines as cyclin dependent kinase inhibitors |
| US7067661B2 (en) * | 2002-09-04 | 2006-06-27 | Schering Corporation | Pyrazolopyrimidines as cyclin dependent kinase inhibitors |
| US7161003B1 (en) * | 2002-09-04 | 2007-01-09 | Schering Corporation | Pyrazolopyrimidines as cyclin dependent kinase inhibitors |
| PL375149A1 (en) | 2002-10-03 | 2005-11-28 | F.Hoffmann-La Roche Ag | Indole-3-carboxamides as glucokinase (gk) activators |
| RU2005113713A (ru) * | 2002-10-03 | 2006-01-20 | Новартис АГ (CH) | Замещенные (тиазол-2-ил)амиды или сульфонамиды в качестве активаторов глюкокиназы, которые могут применяться при лечении диабета типа 2 |
| WO2004037789A2 (en) * | 2002-10-24 | 2004-05-06 | Merck Patent Gmbh | Methylene urea derivatives as raf-kinase inhibitors |
| EP1567487A4 (en) * | 2002-11-15 | 2005-11-16 | Bristol Myers Squibb Co | OPEN-CHAINED, PROLYL-FROSTED MODULATORS OF ANDROGEN RECEPTOR FUNCTION |
| AU2004262369A1 (en) * | 2003-07-29 | 2005-02-10 | Bristol-Myers Squibb Company | Biomarkers of cyclin-dependent kinase modulation |
| US6949895B2 (en) * | 2003-09-03 | 2005-09-27 | Axcelis Technologies, Inc. | Unipolar electrostatic quadrupole lens and switching methods for charged beam transport |
| US7256208B2 (en) * | 2003-11-13 | 2007-08-14 | Bristol-Myers Squibb Company | Monocyclic N-Aryl hydantoin modulators of androgen receptor function |
| WO2005058341A2 (en) * | 2003-12-11 | 2005-06-30 | Theravance, Inc. | Compositions for use in the treatment of mutant receptor tyrosine kinase driven cellular proliferative diseases |
| WO2005066145A1 (en) | 2004-01-06 | 2005-07-21 | Novo Nordisk A/S | Heteroaryl-ureas and their use as glucokinase activators |
| WO2005072731A1 (en) * | 2004-01-29 | 2005-08-11 | X-Ceptor Therapeutics, Inc. | 3-phenyl-n- ((1, 3, 4) thiadiazol-2-yl) -acrylamide derivatives and related compounds as modulators of estrogen-related receptors for the treatment of e.g. cancer, rheumatoid arthritis or neurological disorders |
| EP1716122B1 (en) * | 2004-01-30 | 2017-04-19 | Vertex Pharmaceuticals Incorporated | Modulators of atp-binding cassette transporters |
| US7977322B2 (en) | 2004-08-20 | 2011-07-12 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-binding cassette transporters |
| US7820702B2 (en) * | 2004-02-04 | 2010-10-26 | Bristol-Myers Squibb Company | Sulfonylpyrrolidine modulators of androgen receptor function and method |
| US20050182105A1 (en) * | 2004-02-04 | 2005-08-18 | Nirschl Alexandra A. | Method of using 3-cyano-4-arylpyridine derivatives as modulators of androgen receptor function |
| EP1568368A1 (en) * | 2004-02-26 | 2005-08-31 | Schering Aktiengesellschaft | Pharmaceutical combination comprising a CDK inhibitor and a VEGF receptor inhibitor |
| US7378426B2 (en) | 2004-03-01 | 2008-05-27 | Bristol-Myers Squibb Company | Fused heterotricyclic compounds as inhibitors of 17β-hydroxysteroid dehydrogenase 3 |
| US7388027B2 (en) * | 2004-03-04 | 2008-06-17 | Bristol-Myers Squibb Company | Bicyclic compounds as modulators of androgen receptor function and method |
| US7696241B2 (en) * | 2004-03-04 | 2010-04-13 | Bristol-Myers Squibb Company | Bicyclic compounds as modulators of androgen receptor function and method |
| US7625923B2 (en) | 2004-03-04 | 2009-12-01 | Bristol-Myers Squibb Company | Bicyclic modulators of androgen receptor function |
| US7211576B2 (en) | 2004-04-20 | 2007-05-01 | Hoffmann-La Roche Inc. | Diaminothiazoles |
| CA2588400A1 (en) | 2004-11-18 | 2006-05-26 | Bristol-Myers Squibb Company | Enteric coated bead comprising ixabepilone, and preparation thereof |
| US20100105745A1 (en) * | 2005-01-04 | 2010-04-29 | Toshinari Minamoto | Suppression of cancer and method for evaluating anticancer agent based on the effect of inhibiting gsk3 beta |
| JPWO2006073202A1 (ja) * | 2005-01-04 | 2008-08-07 | 国立大学法人金沢大学 | ＧＳＫ３β阻害効果に基づくがんの抑制および抗がん剤の評価方法 |
| ES2382815T3 (es) | 2005-07-08 | 2012-06-13 | Novo Nordisk A/S | Dicicloalquilcarbamoil ureas como activadores de glucoquinasa |
| EP2377856A1 (en) * | 2005-07-14 | 2011-10-19 | Novo Nordisk A/S | Urea glucokinase activators |
| EP1948657A1 (en) * | 2005-11-15 | 2008-07-30 | Vertex Pharmaceuticals Incorporated | Azaindazoles useful as inhibitors of kinases |
| US7592461B2 (en) * | 2005-12-21 | 2009-09-22 | Bristol-Myers Squibb Company | Indane modulators of glucocorticoid receptor, AP-1, and/or NF-κB activity and use thereof |
| US7888504B2 (en) * | 2006-07-06 | 2011-02-15 | Bristol-Myers Squibb Company | Glucokinase activators and methods of using same |
| US20080188524A1 (en) * | 2006-10-25 | 2008-08-07 | Martin Augustin | Methods of treating pain |
| WO2008070672A2 (en) | 2006-12-04 | 2008-06-12 | The Board Of Trustees Of The University Of Illinois | Compositions and methods to treat cancer with cupredoxins and cpg rich dna |
| EP2519517B1 (en) | 2009-12-29 | 2015-03-25 | Dana-Farber Cancer Institute, Inc. | Type ii raf kinase inhibitors |
| WO2011143466A1 (en) | 2010-05-12 | 2011-11-17 | Vanderbilt University | Heterocyclic sulfone mglur4 allosteric potentiators, compositions, and methods of treating neurological dysfunction |
| EP2580320B1 (en) | 2010-06-14 | 2018-08-01 | The Scripps Research Institute | Reprogramming of cells to a new fate |
| MX2013004724A (es) * | 2010-11-01 | 2013-08-29 | Romark Lab Lc | Compuestos de tiazolida alquilsulfinilo-sustituidos. |
| WO2012100206A2 (en) | 2011-01-20 | 2012-07-26 | Board Of Regents, The University Of Texas System | Mri markers, delivery and extraction systems, and methods of manufacture and use thereof |
| CN102863474A (zh) | 2011-07-09 | 2013-01-09 | 陈小平 | 一类治疗细胞增殖性疾病的铂化合物、其制备方法和应用 |
| CN102993239A (zh) | 2011-09-19 | 2013-03-27 | 陈小平 | 离去基团含氨基或烷胺基的丁二酸衍生物的铂类化合物 |
| US8940742B2 (en) * | 2012-04-10 | 2015-01-27 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| CN104768962B (zh) | 2012-11-17 | 2017-04-05 | 北京市丰硕维康技术开发有限责任公司 | 离去基团是含氨基或烷氨基的丙二酸衍生物的铂类化合物 |
| CN105228626A (zh) * | 2013-03-15 | 2016-01-06 | 加州生物医学研究所 | 用于诱导软骨形成的化合物和方法 |
| WO2015051241A1 (en) | 2013-10-04 | 2015-04-09 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| SG10201902074UA (en) | 2013-10-04 | 2019-04-29 | Infinity Pharmaceuticals Inc | Heterocyclic compounds and uses thereof |
| CN113616656B (zh) | 2014-03-19 | 2023-02-17 | 无限药品股份有限公司 | 用于治疗PI3K-γ介导的障碍的杂环化合物 |
| GB201409471D0 (en) * | 2014-05-28 | 2014-07-09 | Euro Celtique Sa | Pharmaceutical composition |
| GB201409485D0 (en) | 2014-05-28 | 2014-07-09 | Euro Celtique Sa | Pharmaceutical composition |
| WO2016054491A1 (en) | 2014-10-03 | 2016-04-07 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| JP6854762B2 (ja) | 2014-12-23 | 2021-04-07 | 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 | サイクリン依存性キナーゼ７（ｃｄｋ７）の阻害剤 |
| AU2016243529B2 (en) | 2015-03-27 | 2021-03-25 | Dana-Farber Cancer Institute, Inc. | Inhibitors of cyclin-dependent kinases |
| JP7028766B2 (ja) * | 2015-09-09 | 2022-03-02 | 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 | サイクリン依存性キナーゼの阻害剤 |
| AU2016322552B2 (en) | 2015-09-14 | 2021-03-25 | Infinity Pharmaceuticals, Inc. | Solid forms of isoquinolinone derivatives, process of making, compositions comprising, and methods of using the same |
| WO2017161116A1 (en) | 2016-03-17 | 2017-09-21 | Infinity Pharmaceuticals, Inc. | Isotopologues of isoquinolinone and quinazolinone compounds and uses thereof as pi3k kinase inhibitors |
| EA035401B1 (ru) * | 2016-04-06 | 2020-06-08 | Инновейтив Молекьюлз Гмбх | Производные аминотиазола, полученные в качестве противовирусных средств |
| WO2017214269A1 (en) | 2016-06-08 | 2017-12-14 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| CA3040155C (en) | 2016-10-11 | 2024-01-16 | Euro-Celtique S.A. | Compound for use in the treatment of hodgkin lymphoma |
| GB201709406D0 (en) | 2017-06-13 | 2017-07-26 | Euro-Cletique S A | Compounds for treating TNBC |
| GB201709403D0 (en) | 2017-06-13 | 2017-07-26 | Euro Celtique Sa | Compounds for treating sarcoma |
| GB201709402D0 (en) | 2017-06-13 | 2017-07-26 | Euro Celtique Sa | Compounds for treating t-pll |
| GB201709405D0 (en) | 2017-06-13 | 2017-07-26 | Euro Celtique Sa | Compounds for treating ovarian cancer |
| UA126163C2 (uk) * | 2017-10-05 | 2022-08-25 | Інновейтів Молекьюлз Ґмбх | Енантіомери серії противірусних сполук |
| CA3093025A1 (en) | 2018-06-12 | 2019-12-19 | Vtv Therapeutics Llc | Therapeutic uses of glucokinase activators in combination with insulin or insulin analogs |
| EP3810132A4 (en) | 2018-06-25 | 2022-06-22 | Dana-Farber Cancer Institute, Inc. | TAIRE FAMILY KINASE INHIBITORS AND RELATED USES |
| JP2022522928A (ja) | 2018-12-18 | 2022-04-21 | ムンディファーマ・インターナショナル・コーポレーション・リミテッド | 多発性骨髄腫を治療するための化合物 |
| WO2021167840A1 (en) | 2020-02-18 | 2021-08-26 | Vtv Therapeutics Llc | Sulfoxide and sulfone glucokinase activators and methods of use thereof |
| JP2023545588A (ja) * | 2020-10-16 | 2023-10-30 | ツェーエムエム－フォルシュングスツェントルム フュア モレクラレ メディツィン ゲーエムベーハー | ヘテロ環式カリンｒｉｎｇユビキチンリガーゼ化合物及びその使用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1088049A (en) * | 1975-06-03 | 1980-10-21 | Takashi Masugi | 3-substituted-7-substituted alkanamido-3-cephem-4- carboxylic acid compounds and processes for preparation thereof |
| NO831160L (no) * | 1982-04-08 | 1983-10-10 | Erba Farmitalia | Fremstilling av substituerte penem-derivater |
| JPS6339868A (ja) * | 1986-08-04 | 1988-02-20 | Otsuka Pharmaceut Factory Inc | ジ低級アルキルフエノ−ル誘導体 |
| DE4119756A1 (de) * | 1991-06-15 | 1992-12-17 | Basf Ag | Aminoalkylsubstituierte 5-mercaptothiazole, ihre herstellung und verwendung |
| JPH0859669A (ja) * | 1994-06-13 | 1996-03-05 | Takeda Chem Ind Ltd | セフェム化合物、その製造法及び剤 |
| CA2206315A1 (en) * | 1994-11-29 | 1996-06-06 | Hisamitsu Pharmaceutical Co., Inc. | Antibacterial preparation or bactericide comprising 2-aminothiazole derivative and/or salt thereof |
-
1998
- 1998-10-21 US US09/176,239 patent/US6040321A/en not_active Expired - Lifetime
- 1998-11-02 RU RU2000115305/04A patent/RU2211839C2/ru not_active IP Right Cessation
- 1998-11-02 KR KR10-2003-7004561A patent/KR20030036862A/ko not_active Ceased
- 1998-11-02 ES ES98956431T patent/ES2296347T3/es not_active Expired - Lifetime
- 1998-11-02 TR TR2000/01344T patent/TR200001344T2/xx unknown
- 1998-11-02 AT AT98956431T patent/ATE374771T1/de active
- 1998-11-02 AU AU12955/99A patent/AU730607B2/en not_active Ceased
- 1998-11-02 CZ CZ20001744A patent/CZ297907B6/cs not_active IP Right Cessation
- 1998-11-02 WO PCT/US1998/023197 patent/WO1999024416A1/en not_active Ceased
- 1998-11-02 CN CNB988110911A patent/CN1160343C/zh not_active Expired - Fee Related
- 1998-11-02 BR BR9814124-4A patent/BR9814124A/pt not_active Application Discontinuation
- 1998-11-02 EP EP98956431A patent/EP1042307B1/en not_active Expired - Lifetime
- 1998-11-02 KR KR10-2000-7004995A patent/KR100454426B1/ko not_active Expired - Fee Related
- 1998-11-02 DE DE69838515T patent/DE69838515T2/de not_active Expired - Lifetime
- 1998-11-02 HU HU0004559A patent/HUP0004559A3/hu unknown
- 1998-11-02 DK DK98956431T patent/DK1042307T3/da active
- 1998-11-02 CA CA002309551A patent/CA2309551C/en not_active Expired - Fee Related
- 1998-11-02 PT PT98956431T patent/PT1042307E/pt unknown
- 1998-11-02 JP JP2000520430A patent/JP4344084B2/ja not_active Expired - Fee Related
- 1998-11-02 NZ NZ503828A patent/NZ503828A/xx active Application Revival
- 1998-11-02 PL PL340540A patent/PL204642B1/pl not_active IP Right Cessation
- 1998-11-02 ID IDW20000894A patent/ID23983A/id unknown
- 1998-11-02 IL IL13558998A patent/IL135589A/en not_active IP Right Cessation
- 1998-11-09 TW TW087118625A patent/TW593292B/zh not_active IP Right Cessation
- 1998-11-09 UY UY25239A patent/UY25239A1/es not_active IP Right Cessation
- 1998-11-11 ZA ZA9810332A patent/ZA9810332B/xx unknown
- 1998-11-11 CO CO98066514A patent/CO4990957A1/es unknown
- 1998-11-12 MY MYPI98005150A patent/MY120779A/en unknown
- 1998-11-12 AR ARP980105716A patent/AR017182A1/es unknown
- 1998-11-12 PE PE1998001093A patent/PE131699A1/es not_active Application Discontinuation
- 1998-11-12 EG EG140698A patent/EG24028A/xx active
-
2000
- 2000-04-27 NO NO20002153A patent/NO316773B1/no not_active IP Right Cessation
-
2007
- 2007-12-27 CY CY20071101633T patent/CY1107509T1/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR100454426B1 (ko) | 시클린 의존성 키나아제의 아미노티아졸 억제제 | |
| US6262096B1 (en) | Aminothiazole inhibitors of cyclin dependent kinases | |
| EP1043998B1 (en) | USE OF PYRAZOLO [3,4-b] PYRIDINE AS CYCLIN DEPENDANT KINASE INHIBITORS | |
| EP1087951B9 (en) | Carbon substituted aminothiazole inhibitors of cyclin dependent kinases | |
| KR20110031367A (ko) | 화합물 251 | |
| CZ20022013A3 (cs) | N-[5-[[[5-Alkyl-2-oxazolyl]methyl]thio]-2-thiazolyl]karboxamidové inhibitory cyklin-dependentních kinas | |
| SI21099A (sl) | N-(5-(((5-alkil-2-oksazolil)metil)tio)-2-tiazolil) karboksamidni inhibitorji ciklin odvisnih kinaz | |
| US6610724B2 (en) | 3-Aminopyrazole inhibitors of cyclin dependent kinases | |
| HK1029109B (en) | Aminothiazole inhibitors of cyclin dependent kinases | |
| HK1029109A1 (en) | Aminothiazole inhibitors of cyclin dependent kinases | |
| MXPA00004488A (en) | Aminothiazole inhibitors of cyclin dependent kinases |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A107 | Divisional application of patent | ||
| PA0104 | Divisional application for international application |
Comment text: Divisional Application for International Patent Patent event code: PA01041R01D Patent event date: 20030328 |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 20031028 Comment text: Request for Examination of Application |
|
| E902 | Notification of reason for refusal | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20040126 Patent event code: PE09021S01D |
|
| E601 | Decision to refuse application | ||
| PE0601 | Decision on rejection of patent |
Patent event date: 20041027 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 20040126 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |
|
| J201 | Request for trial against refusal decision | ||
| PJ0201 | Trial against decision of rejection |
Patent event date: 20041126 Comment text: Request for Trial against Decision on Refusal Patent event code: PJ02012R01D Patent event date: 20041027 Comment text: Decision to Refuse Application Patent event code: PJ02011S01I Appeal kind category: Appeal against decision to decline refusal Decision date: 20060227 Appeal identifier: 2004101005596 Request date: 20041126 |
|
| J301 | Trial decision |
Free format text: TRIAL DECISION FOR APPEAL AGAINST DECISION TO DECLINE REFUSAL REQUESTED 20041126 Effective date: 20060227 |
|
| PJ1301 | Trial decision |
Patent event code: PJ13011S01D Patent event date: 20060228 Comment text: Trial Decision on Objection to Decision on Refusal Appeal kind category: Appeal against decision to decline refusal Request date: 20041126 Decision date: 20060227 Appeal identifier: 2004101005596 |