JP2013514983A5 - - Google Patents
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- 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
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- 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
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| PCT/US2010/060930 WO2011075616A1 (en) | 2009-12-18 | 2010-12-17 | Substituted pyrido[2,3-d]pyrimidin-7(8h)-ones and therapeutic uses thereof |
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| US8987267B2 (en) | 2010-08-05 | 2015-03-24 | Temple University—Of the Commonwealth System of Higher Education | 2-substituted-8-alkyl-7-OXO-7,8-dihydropyrido[2,3-D]pyrimidine-6-carbonitriles and uses thereof in treating proliferative disorders |
| MX2013013211A (es) * | 2011-05-18 | 2014-02-20 | Syngenta Participations Ag | Compuestos insecticidas a base de derivados de ariltioacetamida. |
| EP2968331B1 (en) | 2013-03-14 | 2020-07-01 | Icahn School of Medicine at Mount Sinai | Pyrimidine compounds as kinase inhibitors |
| US9828373B2 (en) | 2014-07-26 | 2017-11-28 | Sunshine Lake Pharma Co., Ltd. | 2-amino-pyrido[2,3-D]pyrimidin-7(8H)-one derivatives as CDK inhibitors and uses thereof |
| EP3676267A4 (en) * | 2017-08-31 | 2021-04-14 | Dana Farber Cancer Institute, Inc. | EGFR AND / OR HER2 INHIBITORS 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 |
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| 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 |
| PL203805B1 (pl) | 2000-02-25 | 2009-11-30 | Hoffmann La Roche | Zastosowanie cyklicznych związków heteroaromatycznych, lek i cykliczne związki heteroaromatyczne |
| CA2401368A1 (en) | 2000-03-06 | 2001-09-27 | Warner-Lambert Company | 5-alkylpyrido[2,3-d]pyrimidines tyrosine kinase inhibitors |
| JP4064818B2 (ja) * | 2001-02-12 | 2008-03-19 | エフ．ホフマン−ラ ロシュ アーゲー | ６−置換ピリド−ピリミジン類 |
| KR100669578B1 (ko) | 2002-01-22 | 2007-01-15 | 워너-램버트 캄파니 엘엘씨 | 2-(피리딘-2-일아미노)-피리도[2,3-ｄ]피리미딘-7-온 |
| ES2281843T3 (es) * | 2003-11-13 | 2007-10-01 | F. Hoffmann-La Roche Ag | Pirido-7-pirimidin-7-onas sustituidas con hidroxialquilo. |
| 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 |
| EA201200669A1 (ru) | 2005-10-07 | 2012-11-30 | Экселиксис, Инк. | ПИРИДОПИРИМИДИНОНОВЫЕ ИНГИБИТОРЫ PI3Kα |
| 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 |
| 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 |
| EP2084159A1 (en) | 2006-10-16 | 2009-08-05 | GPC Biotech Inc. | Pyrido ý2, 3-d¨pyrimidines and their use as kinase inhibitors |
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2010
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- 2010-12-17 EP EP10838276.3A patent/EP2512250A4/en not_active Withdrawn
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2012
- 2012-06-17 IL IL220448A patent/IL220448A/en not_active IP Right Cessation
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