JP2013514983A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2013514983A5 JP2013514983A5 JP2012544865A JP2012544865A JP2013514983A5 JP 2013514983 A5 JP2013514983 A5 JP 2013514983A5 JP 2012544865 A JP2012544865 A JP 2012544865A JP 2012544865 A JP2012544865 A JP 2012544865A JP 2013514983 A5 JP2013514983 A5 JP 2013514983A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrimidin
- alkyl
- ylamino
- compound
- salt
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 56
- 150000003839 salts Chemical class 0.000 claims 51
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 29
- 125000000217 alkyl group Chemical group 0.000 claims 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 20
- 229910052739 hydrogen Inorganic materials 0.000 claims 17
- 239000001257 hydrogen Substances 0.000 claims 17
- -1 substituted Chemical class 0.000 claims 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 14
- 125000003118 aryl group Chemical group 0.000 claims 14
- 125000002947 alkylene group Chemical group 0.000 claims 11
- 239000000203 mixture Substances 0.000 claims 11
- 229910052757 nitrogen Inorganic materials 0.000 claims 11
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 10
- 125000000623 heterocyclic group Chemical group 0.000 claims 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 6
- 210000004027 cell Anatomy 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 5
- 206010028980 Neoplasm Diseases 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- 230000002062 proliferating effect Effects 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 201000011510 cancer Diseases 0.000 claims 4
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 3
- 239000007795 chemical reaction product Substances 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 229940127121 immunoconjugate Drugs 0.000 claims 3
- 210000004698 lymphocyte Anatomy 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 210000004881 tumor cell Anatomy 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 208000030289 Lymphoproliferative disease Diseases 0.000 claims 2
- 208000000453 Skin Neoplasms Diseases 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 210000000481 breast Anatomy 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 208000032839 leukemia Diseases 0.000 claims 2
- 125000006693 (C2-C9) heterocyclyl group Chemical group 0.000 claims 1
- ZCBIFHNDZBSCEP-UHFFFAOYSA-N 1H-indol-5-amine Chemical compound NC1=CC=C2NC=CC2=C1 ZCBIFHNDZBSCEP-UHFFFAOYSA-N 0.000 claims 1
- XUTVFBVLUHSIBC-UHFFFAOYSA-N 2-(1h-indol-4-ylamino)-6-(4-methoxyphenyl)sulfonyl-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C(N(C)C1=N2)=O)=CC1=CN=C2NC1=CC=CC2=C1C=CN2 XUTVFBVLUHSIBC-UHFFFAOYSA-N 0.000 claims 1
- LXHBYNYYXSUIGS-UHFFFAOYSA-N 2-(1h-indol-4-ylamino)-8-methyl-6-(4-methylphenyl)sulfonylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(N(C)C1=N2)=O)=CC1=CN=C2NC1=CC=CC2=C1C=CN2 LXHBYNYYXSUIGS-UHFFFAOYSA-N 0.000 claims 1
- VAKARYFWENOUDM-UHFFFAOYSA-N 2-(1h-indol-5-ylamino)-6-(4-methoxyphenyl)sulfonyl-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C(C(N(C)C1=N2)=O)=CC1=CN=C2NC1=CC=C(NC=C2)C2=C1 VAKARYFWENOUDM-UHFFFAOYSA-N 0.000 claims 1
- OBJHBFRLGFYXOG-UHFFFAOYSA-N 2-(1h-indol-5-ylamino)-8-methyl-6-(4-methylphenyl)sulfonylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(N(C)C1=N2)=O)=CC1=CN=C2NC1=CC=C(NC=C2)C2=C1 OBJHBFRLGFYXOG-UHFFFAOYSA-N 0.000 claims 1
- FYAZYJJIJMWDKA-UHFFFAOYSA-N 2-(1h-indol-6-ylamino)-8-methyl-6-(4-methylphenyl)sulfonylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(N(C)C1=N2)=O)=CC1=CN=C2NC1=CC=C(C=CN2)C2=C1 FYAZYJJIJMWDKA-UHFFFAOYSA-N 0.000 claims 1
- NGLUHBKHRJWHBE-UHFFFAOYSA-N 2-(4-acetylpiperazin-1-yl)-6-(4-chlorophenyl)sulfonyl-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C(=O)C)CCN1C1=NC=C(C=C(C(=O)N2C)S(=O)(=O)C=3C=CC(Cl)=CC=3)C2=N1 NGLUHBKHRJWHBE-UHFFFAOYSA-N 0.000 claims 1
- ZKOJYIDLWPSYGM-UHFFFAOYSA-N 2-(4-chloroanilino)-6-(4-chlorophenyl)sulfonyl-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=C(S(=O)(=O)C=3C=CC(Cl)=CC=3)C(=O)N(C)C2=NC=1NC1=CC=C(Cl)C=C1 ZKOJYIDLWPSYGM-UHFFFAOYSA-N 0.000 claims 1
- XHJRKLRJGMQTRR-UHFFFAOYSA-N 2-(4-methoxyanilino)-8-methyl-6-(4-methylphenyl)sulfonylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OC)=CC=C1NC1=NC=C(C=C(C(=O)N2C)S(=O)(=O)C=3C=CC(C)=CC=3)C2=N1 XHJRKLRJGMQTRR-UHFFFAOYSA-N 0.000 claims 1
- LELLRLLLTNANMW-UHFFFAOYSA-N 4-[2-(1h-indol-5-ylamino)-8-methyl-7-oxopyrido[2,3-d]pyrimidin-6-yl]sulfonylbenzoic acid Chemical compound O=C1N(C)C2=NC(NC=3C=C4C=CNC4=CC=3)=NC=C2C=C1S(=O)(=O)C1=CC=C(C(O)=O)C=C1 LELLRLLLTNANMW-UHFFFAOYSA-N 0.000 claims 1
- GDRREQHJEAYYEO-UHFFFAOYSA-N 6-(2,4-difluorophenyl)sulfonyl-2-(1h-indazol-5-ylamino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NC=3C=C4C=NNC4=CC=3)=NC=C2C=C1S(=O)(=O)C1=CC=C(F)C=C1F GDRREQHJEAYYEO-UHFFFAOYSA-N 0.000 claims 1
- ZEHBZHZMQSHZFI-UHFFFAOYSA-N 6-(2,4-difluorophenyl)sulfonyl-2-(1h-indol-5-ylamino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NC=3C=C4C=CNC4=CC=3)=NC=C2C=C1S(=O)(=O)C1=CC=C(F)C=C1F ZEHBZHZMQSHZFI-UHFFFAOYSA-N 0.000 claims 1
- ABOCGOHSMQJXJD-UHFFFAOYSA-N 6-(2,4-difluorophenyl)sulfonyl-8-methyl-2-(2-morpholin-4-ylethylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=C(S(=O)(=O)C=3C(=CC(F)=CC=3)F)C(=O)N(C)C2=NC=1NCCN1CCOCC1 ABOCGOHSMQJXJD-UHFFFAOYSA-N 0.000 claims 1
- LEQVQBKEEKQFFF-UHFFFAOYSA-N 6-(2,4-difluorophenyl)sulfonyl-8-methyl-2-[(2-oxo-1,3-dihydroindol-5-yl)amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NC=3C=C4CC(=O)NC4=CC=3)=NC=C2C=C1S(=O)(=O)C1=CC=C(F)C=C1F LEQVQBKEEKQFFF-UHFFFAOYSA-N 0.000 claims 1
- TZNCRLWWLHLDPJ-UHFFFAOYSA-N 6-(2,4-difluorophenyl)sulfonyl-8-methyl-2-methylsulfanylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(SC)=NC=C2C=C1S(=O)(=O)C1=CC=C(F)C=C1F TZNCRLWWLHLDPJ-UHFFFAOYSA-N 0.000 claims 1
- ROPYKEHRRDHEDL-UHFFFAOYSA-N 6-(2,4-difluorophenyl)sulfonyl-8-methyl-2-methylsulfinylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(S(C)=O)=NC=C2C=C1S(=O)(=O)C1=CC=C(F)C=C1F ROPYKEHRRDHEDL-UHFFFAOYSA-N 0.000 claims 1
- GVNFPLWGZFFQLD-UHFFFAOYSA-N 6-(3-chloro-4-fluorophenyl)sulfonyl-2-(1h-indazol-5-ylamino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NC=3C=C4C=NNC4=CC=3)=NC=C2C=C1S(=O)(=O)C1=CC=C(F)C(Cl)=C1 GVNFPLWGZFFQLD-UHFFFAOYSA-N 0.000 claims 1
- VWQWRJLBCHUFRQ-UHFFFAOYSA-N 6-(3-chloro-4-fluorophenyl)sulfonyl-2-(1h-indol-4-ylamino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NC=3C=4C=CNC=4C=CC=3)=NC=C2C=C1S(=O)(=O)C1=CC=C(F)C(Cl)=C1 VWQWRJLBCHUFRQ-UHFFFAOYSA-N 0.000 claims 1
- ITJHZDKREUXYAW-UHFFFAOYSA-N 6-(3-chloro-4-fluorophenyl)sulfonyl-2-(1h-indol-5-ylamino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NC=3C=C4C=CNC4=CC=3)=NC=C2C=C1S(=O)(=O)C1=CC=C(F)C(Cl)=C1 ITJHZDKREUXYAW-UHFFFAOYSA-N 0.000 claims 1
- BIMWWYGHYYAKKG-UHFFFAOYSA-N 6-(3-chloro-4-fluorophenyl)sulfonyl-2-(1h-indol-5-ylamino)-8h-pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=C(Cl)C(F)=CC=C1S(=O)(=O)C(C(NC1=N2)=O)=CC1=CN=C2NC1=CC=C(NC=C2)C2=C1 BIMWWYGHYYAKKG-UHFFFAOYSA-N 0.000 claims 1
- VCUUTCCRXTWNIO-UHFFFAOYSA-N 6-(3-chloro-4-fluorophenyl)sulfonyl-8-methyl-2-(1h-pyrrolo[2,3-b]pyridin-5-ylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NC=3C=C4C=CNC4=NC=3)=NC=C2C=C1S(=O)(=O)C1=CC=C(F)C(Cl)=C1 VCUUTCCRXTWNIO-UHFFFAOYSA-N 0.000 claims 1
- KVUNNIWNBHUCHD-UHFFFAOYSA-N 6-(3-chloro-4-fluorophenyl)sulfonyl-8-methyl-2-[(2-oxo-1,3-dihydroindol-5-yl)amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NC=3C=C4CC(=O)NC4=CC=3)=NC=C2C=C1S(=O)(=O)C1=CC=C(F)C(Cl)=C1 KVUNNIWNBHUCHD-UHFFFAOYSA-N 0.000 claims 1
- ZRUXMZQWXYNIAR-UHFFFAOYSA-N 6-(4-bromophenyl)sulfonyl-2-(1h-indol-5-ylamino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NC=3C=C4C=CNC4=CC=3)=NC=C2C=C1S(=O)(=O)C1=CC=C(Br)C=C1 ZRUXMZQWXYNIAR-UHFFFAOYSA-N 0.000 claims 1
- IZWLPQQMXPJYGH-UHFFFAOYSA-N 6-(4-chlorophenyl)sulfonyl-2-(1h-indol-4-ylamino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NC=3C=4C=CNC=4C=CC=3)=NC=C2C=C1S(=O)(=O)C1=CC=C(Cl)C=C1 IZWLPQQMXPJYGH-UHFFFAOYSA-N 0.000 claims 1
- VMFHEFCVRVXZNB-UHFFFAOYSA-N 6-(4-chlorophenyl)sulfonyl-2-(1h-indol-5-ylamino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NC=3C=C4C=CNC4=CC=3)=NC=C2C=C1S(=O)(=O)C1=CC=C(Cl)C=C1 VMFHEFCVRVXZNB-UHFFFAOYSA-N 0.000 claims 1
- RKTRISFGTUOQPN-UHFFFAOYSA-N 6-(4-chlorophenyl)sulfonyl-2-(4-methoxyanilino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OC)=CC=C1NC1=NC=C(C=C(C(=O)N2C)S(=O)(=O)C=3C=CC(Cl)=CC=3)C2=N1 RKTRISFGTUOQPN-UHFFFAOYSA-N 0.000 claims 1
- KQEAGKLYAQUDJZ-UHFFFAOYSA-N 6-(4-chlorophenyl)sulfonyl-8-cyclohexyl-2-(4-morpholin-4-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C(C(N(C1CCCCC1)C1=N2)=O)=CC1=CN=C2NC1=CC=C(N2CCOCC2)C=C1 KQEAGKLYAQUDJZ-UHFFFAOYSA-N 0.000 claims 1
- YDVJMPKDDFLLMP-UHFFFAOYSA-N 6-(4-chlorophenyl)sulfonyl-8-cyclohexyl-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=C(C(=O)N2C3CCCCC3)S(=O)(=O)C=3C=CC(Cl)=CC=3)C2=N1 YDVJMPKDDFLLMP-UHFFFAOYSA-N 0.000 claims 1
- CRHNJCUVVZOUMR-UHFFFAOYSA-N 6-(4-chlorophenyl)sulfonyl-8-cyclopentyl-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=C(C(=O)N2C3CCCC3)S(=O)(=O)C=3C=CC(Cl)=CC=3)C2=N1 CRHNJCUVVZOUMR-UHFFFAOYSA-N 0.000 claims 1
- CHTWJOJHIJVWSG-UHFFFAOYSA-N 6-(4-chlorophenyl)sulfonyl-8-cyclopentyl-2-methylsulfanylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(SC)=NC=C2C=C(S(=O)(=O)C=2C=CC(Cl)=CC=2)C(=O)N1C1CCCC1 CHTWJOJHIJVWSG-UHFFFAOYSA-N 0.000 claims 1
- BHPOJYDVAPBCLS-UHFFFAOYSA-N 6-(4-chlorophenyl)sulfonyl-8-cyclopentyl-2-methylsulfinylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(S(=O)C)=NC=C2C=C(S(=O)(=O)C=2C=CC(Cl)=CC=2)C(=O)N1C1CCCC1 BHPOJYDVAPBCLS-UHFFFAOYSA-N 0.000 claims 1
- UIORDMMRMAXWEB-UHFFFAOYSA-N 6-(4-chlorophenyl)sulfonyl-8-methyl-2-(1h-pyrrolo[2,3-b]pyridin-5-ylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NC=3C=C4C=CNC4=NC=3)=NC=C2C=C1S(=O)(=O)C1=CC=C(Cl)C=C1 UIORDMMRMAXWEB-UHFFFAOYSA-N 0.000 claims 1
- AYQDSCILAZMDJN-UHFFFAOYSA-N 6-(4-chlorophenyl)sulfonyl-8-methyl-2-(3-morpholin-4-ylpropylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=C(S(=O)(=O)C=3C=CC(Cl)=CC=3)C(=O)N(C)C2=NC=1NCCCN1CCOCC1 AYQDSCILAZMDJN-UHFFFAOYSA-N 0.000 claims 1
- YRJPDCGJCBKORL-UHFFFAOYSA-N 6-(4-chlorophenyl)sulfonyl-8-methyl-2-(quinolin-3-ylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NC=3C=C4C=CC=CC4=NC=3)=NC=C2C=C1S(=O)(=O)C1=CC=C(Cl)C=C1 YRJPDCGJCBKORL-UHFFFAOYSA-N 0.000 claims 1
- WPVNZNZUEGUXOM-UHFFFAOYSA-N 6-(4-chlorophenyl)sulfonyl-8-methyl-2-[2-(4-methylpiperazin-1-yl)ethylamino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCN1CCNC1=NC=C(C=C(C(=O)N2C)S(=O)(=O)C=3C=CC(Cl)=CC=3)C2=N1 WPVNZNZUEGUXOM-UHFFFAOYSA-N 0.000 claims 1
- TURFAYJSDRRABW-UHFFFAOYSA-N 6-(4-fluorophenyl)sulfonyl-2-(1h-indazol-5-ylamino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NC=3C=C4C=NNC4=CC=3)=NC=C2C=C1S(=O)(=O)C1=CC=C(F)C=C1 TURFAYJSDRRABW-UHFFFAOYSA-N 0.000 claims 1
- JFYFAAGDHKAZEG-UHFFFAOYSA-N 6-(4-fluorophenyl)sulfonyl-2-(1h-indol-4-ylamino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NC=3C=4C=CNC=4C=CC=3)=NC=C2C=C1S(=O)(=O)C1=CC=C(F)C=C1 JFYFAAGDHKAZEG-UHFFFAOYSA-N 0.000 claims 1
- JQAOJCKJLZWENT-UHFFFAOYSA-N 6-(4-fluorophenyl)sulfonyl-2-(1h-indol-5-ylamino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NC=3C=C4C=CNC4=CC=3)=NC=C2C=C1S(=O)(=O)C1=CC=C(F)C=C1 JQAOJCKJLZWENT-UHFFFAOYSA-N 0.000 claims 1
- QVJAKNZSGPLMPU-UHFFFAOYSA-N 6-(4-fluorophenyl)sulfonyl-2-(1h-indol-6-ylamino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NC=3C=C4NC=CC4=CC=3)=NC=C2C=C1S(=O)(=O)C1=CC=C(F)C=C1 QVJAKNZSGPLMPU-UHFFFAOYSA-N 0.000 claims 1
- UEYJGBDVLLHXOR-UHFFFAOYSA-N 6-(4-fluorophenyl)sulfonyl-8-methyl-2-(1h-pyrrolo[2,3-b]pyridin-5-ylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NC=3C=C4C=CNC4=NC=3)=NC=C2C=C1S(=O)(=O)C1=CC=C(F)C=C1 UEYJGBDVLLHXOR-UHFFFAOYSA-N 0.000 claims 1
- FCPZOGCMAQOPBZ-UHFFFAOYSA-N 6-(4-hydroxyphenyl)sulfonyl-2-(1h-indol-5-ylamino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NC=3C=C4C=CNC4=CC=3)=NC=C2C=C1S(=O)(=O)C1=CC=C(O)C=C1 FCPZOGCMAQOPBZ-UHFFFAOYSA-N 0.000 claims 1
- QYSTWGRTWZPAOD-UHFFFAOYSA-N 6-(benzenesulfonyl)-2-(1h-indol-4-ylamino)-8-propylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CCC)C2=NC(NC=3C=4C=CNC=4C=CC=3)=NC=C2C=C1S(=O)(=O)C1=CC=CC=C1 QYSTWGRTWZPAOD-UHFFFAOYSA-N 0.000 claims 1
- QVFCEFCQUNKANC-UHFFFAOYSA-N 6-(benzenesulfonyl)-2-(1h-indol-5-ylamino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NC=3C=C4C=CNC4=CC=3)=NC=C2C=C1S(=O)(=O)C1=CC=CC=C1 QVFCEFCQUNKANC-UHFFFAOYSA-N 0.000 claims 1
- WEIKHEXRHSYXCS-UHFFFAOYSA-N 6-(benzenesulfonyl)-2-(1h-indol-5-ylamino)-8-propylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CCC)C2=NC(NC=3C=C4C=CNC4=CC=3)=NC=C2C=C1S(=O)(=O)C1=CC=CC=C1 WEIKHEXRHSYXCS-UHFFFAOYSA-N 0.000 claims 1
- RBRAMJHAVWRTPH-UHFFFAOYSA-N 6-(benzenesulfonyl)-2-(1h-indol-6-ylamino)-8-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NC=3C=C4NC=CC4=CC=3)=NC=C2C=C1S(=O)(=O)C1=CC=CC=C1 RBRAMJHAVWRTPH-UHFFFAOYSA-N 0.000 claims 1
- IWTQBSNGCUQPTE-UHFFFAOYSA-N 6-(benzenesulfonyl)-2-(1h-indol-6-ylamino)-8-propylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CCC)C2=NC(NC=3C=C4NC=CC4=CC=3)=NC=C2C=C1S(=O)(=O)C1=CC=CC=C1 IWTQBSNGCUQPTE-UHFFFAOYSA-N 0.000 claims 1
- VMVZFYVAUISHKA-UHFFFAOYSA-N 6-(benzenesulfonyl)-2-phenylsulfanyl-8-propylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=C2C=C(S(=O)(=O)C=3C=CC=CC=3)C(=O)N(CCC)C2=NC=1SC1=CC=CC=C1 VMVZFYVAUISHKA-UHFFFAOYSA-N 0.000 claims 1
- JXGVWEJCPIQCLW-UHFFFAOYSA-N 6-(benzenesulfonyl)-8-cyclopentyl-2-(1h-indol-5-ylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1C(S(=O)(=O)C=2C=CC=CC=2)=CC2=CN=C(NC=3C=C4C=CNC4=CC=3)N=C2N1C1CCCC1 JXGVWEJCPIQCLW-UHFFFAOYSA-N 0.000 claims 1
- ITEMDCAKQVQRFU-UHFFFAOYSA-N 6-(benzenesulfonyl)-8-cyclopentyl-2-(3,4,5-trimethoxyanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound COC1=C(OC)C(OC)=CC(NC=2N=C3N(C4CCCC4)C(=O)C(=CC3=CN=2)S(=O)(=O)C=2C=CC=CC=2)=C1 ITEMDCAKQVQRFU-UHFFFAOYSA-N 0.000 claims 1
- RDUNJPHOCUMHJF-UHFFFAOYSA-N 6-(benzenesulfonyl)-8-cyclopentyl-2-(4-methoxyanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OC)=CC=C1NC1=NC=C(C=C(C(=O)N2C3CCCC3)S(=O)(=O)C=3C=CC=CC=3)C2=N1 RDUNJPHOCUMHJF-UHFFFAOYSA-N 0.000 claims 1
- ZDMGLERDDDTPQA-UHFFFAOYSA-N 6-(benzenesulfonyl)-8-cyclopentyl-2-(4-morpholin-4-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=C2N(C3CCCC3)C(=O)C(S(=O)(=O)C=3C=CC=CC=3)=CC2=CN=C1NC(C=C1)=CC=C1N1CCOCC1 ZDMGLERDDDTPQA-UHFFFAOYSA-N 0.000 claims 1
- MLMHICKPMVFARV-UHFFFAOYSA-N 6-(benzenesulfonyl)-8-cyclopentyl-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=C(C(=O)N2C3CCCC3)S(=O)(=O)C=3C=CC=CC=3)C2=N1 MLMHICKPMVFARV-UHFFFAOYSA-N 0.000 claims 1
- PDQXZVTWMWZVRD-UHFFFAOYSA-N 6-(benzenesulfonyl)-8-cyclopentyl-2-[4-[5-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl]pyrido[2,3-d]pyrimidin-7-one Chemical compound N1=CC(C(F)(F)F)=CC=C1N1CCN(C=2N=C3N(C4CCCC4)C(=O)C(=CC3=CN=2)S(=O)(=O)C=2C=CC=CC=2)CC1 PDQXZVTWMWZVRD-UHFFFAOYSA-N 0.000 claims 1
- ONDSNCJXBDWOBA-UHFFFAOYSA-N 6-(benzenesulfonyl)-8-cyclopentyl-2-methylsulfanylpyrido[2,3-d]pyrimidin-7-one;6-(benzenesulfonyl)-2-methylsulfanyl-8-propylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CCC)C2=NC(SC)=NC=C2C=C1S(=O)(=O)C1=CC=CC=C1.C12=NC(SC)=NC=C2C=C(S(=O)(=O)C=2C=CC=CC=2)C(=O)N1C1CCCC1 ONDSNCJXBDWOBA-UHFFFAOYSA-N 0.000 claims 1
- PRGAKDXBMLRXQK-UHFFFAOYSA-N 6-(benzenesulfonyl)-8-cyclopentyl-2-methylsulfinylpyrido[2,3-d]pyrimidin-7-one Chemical compound C12=NC(S(=O)C)=NC=C2C=C(S(=O)(=O)C=2C=CC=CC=2)C(=O)N1C1CCCC1 PRGAKDXBMLRXQK-UHFFFAOYSA-N 0.000 claims 1
- DSJNKAYLBBXYCM-UHFFFAOYSA-N 6-(benzenesulfonyl)-8-ethyl-2-(1h-indol-5-ylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(NC=3C=C4C=CNC4=CC=3)=NC=C2C=C1S(=O)(=O)C1=CC=CC=C1 DSJNKAYLBBXYCM-UHFFFAOYSA-N 0.000 claims 1
- XFZNZNXMHPGYRK-UHFFFAOYSA-N 6-(benzenesulfonyl)-8-methyl-2-(1h-pyrrolo[2,3-b]pyridin-5-ylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NC=3C=C4C=CNC4=NC=3)=NC=C2C=C1S(=O)(=O)C1=CC=CC=C1 XFZNZNXMHPGYRK-UHFFFAOYSA-N 0.000 claims 1
- CBYOYUVEWICJBZ-UHFFFAOYSA-N 6-(benzenesulfonyl)-8-methyl-2-(quinolin-6-ylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C)C2=NC(NC=3C=C4C=CC=NC4=CC=3)=NC=C2C=C1S(=O)(=O)C1=CC=CC=C1 CBYOYUVEWICJBZ-UHFFFAOYSA-N 0.000 claims 1
- QENLQBPFPCBNBA-UHFFFAOYSA-N 8-methyl-6-(4-methylphenyl)sulfonyl-2-(1h-pyrrolo[2,3-b]pyridin-5-ylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(N(C)C1=N2)=O)=CC1=CN=C2NC1=CN=C(NC=C2)C2=C1 QENLQBPFPCBNBA-UHFFFAOYSA-N 0.000 claims 1
- WNDFYUHSCGSQQU-UHFFFAOYSA-N 8-methyl-6-(4-methylphenyl)sulfonyl-2-(quinolin-5-ylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(N(C)C1=N2)=O)=CC1=CN=C2NC1=CC=CC2=NC=CC=C12 WNDFYUHSCGSQQU-UHFFFAOYSA-N 0.000 claims 1
- ZINSJVZCLIORLD-UHFFFAOYSA-N 8-methyl-6-(4-methylphenyl)sulfonyl-2-(quinolin-8-ylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(N(C)C1=N2)=O)=CC1=CN=C2NC1=CC=CC2=CC=CN=C12 ZINSJVZCLIORLD-UHFFFAOYSA-N 0.000 claims 1
- XYSZRTHDXHPSRH-UHFFFAOYSA-N 8-methyl-6-(4-methylphenyl)sulfonyl-2-[(2-oxo-1,3-dihydroindol-5-yl)amino]pyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(N(C)C1=N2)=O)=CC1=CN=C2NC1=CC=C(NC(=O)C2)C2=C1 XYSZRTHDXHPSRH-UHFFFAOYSA-N 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 1
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims 1
- 208000003174 Brain Neoplasms Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 206010008342 Cervix carcinoma Diseases 0.000 claims 1
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000001708 Dupuytren contracture Diseases 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims 1
- 206010029098 Neoplasm skin Diseases 0.000 claims 1
- 208000009905 Neurofibromatoses Diseases 0.000 claims 1
- 208000010191 Osteitis Deformans Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 208000027067 Paget disease of bone Diseases 0.000 claims 1
- 208000004362 Penile Induration Diseases 0.000 claims 1
- 208000020758 Peyronie disease Diseases 0.000 claims 1
- 208000002158 Proliferative Vitreoretinopathy Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 208000017442 Retinal disease Diseases 0.000 claims 1
- 206010038923 Retinopathy Diseases 0.000 claims 1
- 206010038934 Retinopathy proliferative Diseases 0.000 claims 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 1
- 208000024313 Testicular Neoplasms Diseases 0.000 claims 1
- 206010057644 Testis cancer Diseases 0.000 claims 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 1
- 206010046798 Uterine leiomyoma Diseases 0.000 claims 1
- 208000033779 X-linked lymphoproliferative disease Diseases 0.000 claims 1
- 230000005856 abnormality Effects 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 210000004100 adrenal gland Anatomy 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 230000006907 apoptotic process Effects 0.000 claims 1
- 208000016738 bone Paget disease Diseases 0.000 claims 1
- 210000000988 bone and bone Anatomy 0.000 claims 1
- 150000001722 carbon compounds Chemical class 0.000 claims 1
- 201000010881 cervical cancer Diseases 0.000 claims 1
- 210000003679 cervix uteri Anatomy 0.000 claims 1
- 208000007118 chronic progressive multiple sclerosis Diseases 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 210000003238 esophagus Anatomy 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 210000001508 eye Anatomy 0.000 claims 1
- 208000024519 eye neoplasm Diseases 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 210000000232 gallbladder Anatomy 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 claims 1
- 208000011379 keloid formation Diseases 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 210000002429 large intestine Anatomy 0.000 claims 1
- 201000010260 leiomyoma Diseases 0.000 claims 1
- 125000005647 linker group Chemical group 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 210000002751 lymph Anatomy 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 210000000214 mouth Anatomy 0.000 claims 1
- 208000025113 myeloid leukemia Diseases 0.000 claims 1
- 208000021971 neovascular inflammatory vitreoretinopathy Diseases 0.000 claims 1
- 201000004931 neurofibromatosis Diseases 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 210000001672 ovary Anatomy 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 230000000750 progressive effect Effects 0.000 claims 1
- 208000035803 proliferative type breast fibrocystic change Diseases 0.000 claims 1
- 230000006785 proliferative vitreoretinopathy Effects 0.000 claims 1
- 210000002307 prostate Anatomy 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 208000037803 restenosis Diseases 0.000 claims 1
- 201000008628 secondary progressive multiple sclerosis Diseases 0.000 claims 1
- 230000001568 sexual effect Effects 0.000 claims 1
- 210000003491 skin Anatomy 0.000 claims 1
- 201000000849 skin cancer Diseases 0.000 claims 1
- 210000002784 stomach Anatomy 0.000 claims 1
- 150000003462 sulfoxides Chemical class 0.000 claims 1
- XUROPSBXOLTUBA-UHFFFAOYSA-N tert-butyl 4-[6-[[6-(benzenesulfonyl)-8-cyclopentyl-7-oxopyrido[2,3-d]pyrimidin-2-yl]amino]pyridin-3-yl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C(C=N1)=CC=C1NC1=NC=C(C=C(C(=O)N2C3CCCC3)S(=O)(=O)C=3C=CC=CC=3)C2=N1 XUROPSBXOLTUBA-UHFFFAOYSA-N 0.000 claims 1
- 201000003120 testicular cancer Diseases 0.000 claims 1
- 210000001550 testis Anatomy 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 238000002054 transplantation Methods 0.000 claims 1
- 210000004291 uterus Anatomy 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28778409P | 2009-12-18 | 2009-12-18 | |
| US61/287,784 | 2009-12-18 | ||
| PCT/US2010/060930 WO2011075616A1 (en) | 2009-12-18 | 2010-12-17 | Substituted pyrido[2,3-d]pyrimidin-7(8h)-ones and therapeutic uses thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013514983A JP2013514983A (ja) | 2013-05-02 |
| JP2013514983A5 true JP2013514983A5 (cg-RX-API-DMAC10.html) | 2013-12-26 |
| JP5797664B2 JP5797664B2 (ja) | 2015-10-21 |
Family
ID=44167710
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012544865A Expired - Fee Related JP5797664B2 (ja) | 2009-12-18 | 2010-12-17 | 置換ピリド［２，３−ｄ］ピリミジン−７（８Ｈ）−オン及びそれらの治療用の使用 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8889696B2 (cg-RX-API-DMAC10.html) |
| EP (1) | EP2512250A4 (cg-RX-API-DMAC10.html) |
| JP (1) | JP5797664B2 (cg-RX-API-DMAC10.html) |
| KR (1) | KR101754664B1 (cg-RX-API-DMAC10.html) |
| CA (1) | CA2784749C (cg-RX-API-DMAC10.html) |
| IL (1) | IL220448A (cg-RX-API-DMAC10.html) |
| WO (1) | WO2011075616A1 (cg-RX-API-DMAC10.html) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT2600719E (pt) | 2010-08-05 | 2014-12-22 | Univ Temple | 8 ¿ alquilo -2 - substituído 7 ¿ oxo ¿ 7,8 ¿ diidropirido [2,3 ¿ d] pirimidina ¿ 6 ¿ carbonitrilos e seus usos |
| MX2013013211A (es) * | 2011-05-18 | 2014-02-20 | Syngenta Participations Ag | Compuestos insecticidas a base de derivados de ariltioacetamida. |
| WO2014151682A1 (en) | 2013-03-14 | 2014-09-25 | Icahn School Of Medicine At Mount Sinai | Pyrimidine compounds as kinase inhibitors |
| WO2016015597A1 (en) | 2014-07-26 | 2016-02-04 | Sunshine Lake Pharma Co., Ltd. | Compounds as cdk small-molecule inhibitors and uses thereof |
| AU2018325442B2 (en) * | 2017-08-31 | 2023-04-13 | Dana-Farber Cancer Institute, Inc. | Inhibitors of EGFR and/or HER2 and methods of use |
| CN119215170B (zh) * | 2024-09-30 | 2025-05-06 | 中国医学科学院医学实验动物研究所 | Plk2作为抗免疫缺陷病毒感染治疗药物的新靶点及其应用 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5620981A (en) | 1995-05-03 | 1997-04-15 | Warner-Lambert Company | Pyrido [2,3-D]pyrimidines for inhibiting protein tyrosine kinase mediated cellular proliferation |
| US6498163B1 (en) | 1997-02-05 | 2002-12-24 | Warner-Lambert Company | Pyrido[2,3-D]pyrimidines and 4-aminopyrimidines as inhibitors of cellular proliferation |
| SK10772002A3 (sk) | 2000-01-27 | 2004-01-08 | Warner-Lambert Company | Pyridopyrimidinónové deriváty na liečbu neurodegeneratívnych ochorení |
| YU63802A (sh) | 2000-02-25 | 2005-06-10 | F. Hoffmann-La Roche Ag. | Modulatori adenozinskih receptora |
| AP2002002643A0 (en) | 2000-03-06 | 2002-12-31 | Warner Lambert Co | 5-alkylpyrido[2,3-d]pyrimidines tyrosine kinase inhibitors |
| SK11322003A3 (en) * | 2001-02-12 | 2004-10-05 | Hoffmann La Roche | 6-Substituted pyrido-pyrimidines |
| NZ534069A (en) * | 2002-01-22 | 2007-03-30 | Warner Lambert Co | 2-(Pyridin-2-ylamino)-pyrido[2,3-d]pyrimidin-7-ones to be used to treat neurodegenerative disorders, viruses and cancer |
| WO2005047284A1 (en) * | 2003-11-13 | 2005-05-26 | F. Hoffmann-La Roche Ag | Hydroxyalkyl substituted pyrido-7-pyrimidin-7-ones |
| CA2555724A1 (en) | 2004-02-18 | 2005-09-09 | Warner-Lambert Company Llc | 2-(pyridin-3-ylamino)-pyrido[2,3-d]pyrimidin-7-ones |
| WO2005105097A2 (en) | 2004-04-28 | 2005-11-10 | Gpc Biotech Ag | Pyridopyrimidines for treating inflammatory and other diseases |
| CA2575804A1 (en) | 2004-08-26 | 2006-03-02 | Boehringer Ingelheim International Gmbh | Pteridinones used as plk (polo like kinase) inhibitors |
| US20060142312A1 (en) | 2004-12-23 | 2006-06-29 | Pfizer Inc | C6-aryl and heteroaryl substituted pyrido[2,3-D] pyrimidin-7-ones |
| GB0428475D0 (en) | 2004-12-30 | 2005-02-02 | 4 Aza Bioscience Nv | Pyrido(3,2-D)pyrimidine derivatives and pharmaceutical compositions useful as medicines for the treatment of autoimmune disorders |
| PT1940839E (pt) | 2005-10-07 | 2013-10-10 | Exelixis Inc | Inibidores de piridopirimidinona pi3k alfa |
| US20090191193A1 (en) | 2006-08-02 | 2009-07-30 | Temple University-Of The Commonwealth System Of Higher Education | Aryl Vinyl Sulfides, Sulfones, Sulfoxides and Sulfonamides, Derivatives Thereof and Therapeutic Uses Thereof |
| BRPI0715566A2 (pt) | 2006-10-16 | 2013-07-02 | Gpc Biotech Inc | composto, prà-droga, composiÇço farmacÊutica, uso de um composto, mÉtodo para inibir a proliferaÇço de cÉlulas e mÉtodo para sintetizar um composto |
| WO2008150260A1 (en) | 2007-06-06 | 2008-12-11 | Gpc Biotech, Inc. | 8-oxy-2-aminopyrido (2, 3-d) pyrimidin-7-one derivatives as kinase inhibitors and anticancer agents |
-
2010
- 2010-12-17 KR KR1020127018922A patent/KR101754664B1/ko not_active Expired - Fee Related
- 2010-12-17 CA CA2784749A patent/CA2784749C/en not_active Expired - Fee Related
- 2010-12-17 WO PCT/US2010/060930 patent/WO2011075616A1/en not_active Ceased
- 2010-12-17 JP JP2012544865A patent/JP5797664B2/ja not_active Expired - Fee Related
- 2010-12-17 EP EP10838276.3A patent/EP2512250A4/en not_active Withdrawn
- 2010-12-17 US US13/516,883 patent/US8889696B2/en not_active Expired - Fee Related
-
2012
- 2012-06-17 IL IL220448A patent/IL220448A/en not_active IP Right Cessation
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN112839715B (zh) | 抑制shp2活性化合物的制造方法 | |
| TWI441820B (zh) | ５－苯胺咪唑并吡啶及使用方法 | |
| JP2019218387A (ja) | キナーゼ調節のための化合物と方法、及びそのための適応 | |
| CN103608350B (zh) | 三唑并吡啶类化合物 | |
| TW201912639A (zh) | Ｓｈｐ２之八氫環戊烷并[c]吡咯別構抑制劑 | |
| JP2010539110A5 (cg-RX-API-DMAC10.html) | ||
| JP2019527718A5 (cg-RX-API-DMAC10.html) | ||
| JP2013538196A5 (cg-RX-API-DMAC10.html) | ||
| TW201726626A (zh) | 作為免疫調節劑之雜環化合物 | |
| JP2016538345A5 (cg-RX-API-DMAC10.html) | ||
| EP3390361A1 (en) | N-phenyl-pyridine-2-carboxamide derivatives and their use as pd-1/pd-l1 protein/protein interaction modulators | |
| CN102137843A (zh) | 作为mek激酶抑制剂的异吲哚酮衍生物及其使用方法 | |
| WO2012000304A1 (zh) | 杂环炔苯类化合物及其药用组合物和应用 | |
| WO2011082400A2 (en) | Modulators of immunoinhibitory receptor pd-1, and methods of use thereof | |
| CN103748096A (zh) | 作为蛋白激酶抑制剂的新型吡咯并嘧啶化合物 | |
| CA2492593A1 (en) | Compounds, compositions, and methods employing same | |
| NZ606281A (en) | 2-substituted-8-alkyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine-6-carbonitriles and uses thereof | |
| JP2022551972A5 (cg-RX-API-DMAC10.html) | ||
| TW201124379A (en) | Aryl substituted sulfonamide compounds and their use as anticancer agents | |
| CN102574846B (zh) | 激酶抑制剂、其前药形式及它们在治疗中的用途 | |
| JP2020506970A5 (cg-RX-API-DMAC10.html) | ||
| JP7691974B2 (ja) | アセチル補酵素ａシンテターゼ短鎖２（ａｃｓｓ２）の小分子阻害剤 | |
| JP5797664B2 (ja) | 置換ピリド［２，３−ｄ］ピリミジン−７（８Ｈ）−オン及びそれらの治療用の使用 | |
| JP2024543207A (ja) | 新規ｈｄａｃ阻害剤及びその治療的使用 | |
| JP6913955B2 (ja) | ＰＩ３Ｋ／ｍＴＯＲ阻害剤としての溶融キノリン化合物 |