JP2010500994A5 - - Google Patents
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- JP2010500994A5 JP2010500994A5 JP2009524671A JP2009524671A JP2010500994A5 JP 2010500994 A5 JP2010500994 A5 JP 2010500994A5 JP 2009524671 A JP2009524671 A JP 2009524671A JP 2009524671 A JP2009524671 A JP 2009524671A JP 2010500994 A5 JP2010500994 A5 JP 2010500994A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- phenyl
- methyloxy
- sulfonyl
- bis
- 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.)
- Pending
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- 150000001875 compounds Chemical class 0.000 claims description 16
- 102000010400 1-phosphatidylinositol-3-kinase activity proteins Human genes 0.000 claims description 15
- 108091007960 PI3Ks Proteins 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 695
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 358
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 353
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 338
- -1 lower alkanyl Chemical group 0.000 claims 152
- 125000001072 heteroaryl group Chemical group 0.000 claims 46
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 43
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 claims 40
- 125000000217 alkyl group Chemical group 0.000 claims 35
- 125000001475 halogen functional group Chemical group 0.000 claims 34
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 33
- 229910052739 hydrogen Inorganic materials 0.000 claims 33
- 239000001257 hydrogen Substances 0.000 claims 33
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 30
- 125000003118 aryl group Chemical group 0.000 claims 28
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims 22
- 125000003342 alkenyl group Chemical group 0.000 claims 21
- 125000003107 substituted aryl group Chemical group 0.000 claims 21
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 19
- 150000002431 hydrogen Chemical class 0.000 claims 19
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 18
- 125000001188 haloalkyl group Chemical group 0.000 claims 17
- 239000000203 mixture Substances 0.000 claims 16
- 125000000304 alkynyl group Chemical group 0.000 claims 15
- 150000001408 amides Chemical class 0.000 claims 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 15
- 125000004262 quinoxalin-2-yl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N=C1* 0.000 claims 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 14
- 125000004438 haloalkoxy group Chemical group 0.000 claims 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 10
- 125000003545 alkoxy group Chemical group 0.000 claims 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 239000012453 solvate Substances 0.000 claims 9
- 241001024304 Mino Species 0.000 claims 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 230000035772 mutation Effects 0.000 claims 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 8
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 8
- 206010028980 Neoplasm Diseases 0.000 claims 7
- 201000011510 cancer Diseases 0.000 claims 7
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 7
- 229940124530 sulfonamide Drugs 0.000 claims 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 6
- 125000003282 alkyl amino group Chemical group 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 4
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 4
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 claims 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims 4
- 125000004104 aryloxy group Chemical group 0.000 claims 4
- 150000003456 sulfonamides Chemical class 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 108010091528 Proto-Oncogene Proteins B-raf Proteins 0.000 claims 3
- 125000002252 acyl group Chemical group 0.000 claims 3
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims 3
- VALZSZJVEFACEZ-UHFFFAOYSA-N azetidine-3-carboxamide Chemical compound NC(=O)C1CNC1 VALZSZJVEFACEZ-UHFFFAOYSA-N 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 3
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- IRHDSXMLSTVXEQ-UHFFFAOYSA-N 2-(ethylamino)-4-methyl-8-propan-2-yl-6-(1h-pyrazol-5-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C(C)C)C2=NC(NCC)=NC(C)=C2C=C1C=1C=CNN=1 IRHDSXMLSTVXEQ-UHFFFAOYSA-N 0.000 claims 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 2
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 2
- HAKUWOSPROHOHW-UHFFFAOYSA-N 8-cyclopentyl-2-(ethylamino)-4-methyl-6-(1h-pyrazol-5-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C2CCCC2)C2=NC(NCC)=NC(C)=C2C=C1C=1C=CNN=1 HAKUWOSPROHOHW-UHFFFAOYSA-N 0.000 claims 2
- HIHMKBKMKSYHII-UHFFFAOYSA-N 8-ethyl-2-(ethylamino)-4-methyl-6-phenylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(NCC)=NC(C)=C2C=C1C1=CC=CC=C1 HIHMKBKMKSYHII-UHFFFAOYSA-N 0.000 claims 2
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 2
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims 2
- 229910002651 NO3 Inorganic materials 0.000 claims 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 2
- 230000003213 activating effect Effects 0.000 claims 2
- 150000001298 alcohols Chemical class 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 2
- 125000004965 chloroalkyl group Chemical group 0.000 claims 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 2
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 2
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 201000001441 melanoma Diseases 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- IADUEWIQBXOCDZ-UHFFFAOYSA-N (2S)-azetidine-2-carboxylic acid Natural products OC(=O)C1CCN1 IADUEWIQBXOCDZ-UHFFFAOYSA-N 0.000 claims 1
- DBTDBYINUJMLRZ-UHFFFAOYSA-N (3,3-difluoroazetidin-1-yl)-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]methanone Chemical compound C=1C=C(I)C=C(F)C=1NC1=C(F)C(F)=CC=C1C(=O)N1CC(F)(F)C1 DBTDBYINUJMLRZ-UHFFFAOYSA-N 0.000 claims 1
- AMKMWZPNFOTRDH-UHFFFAOYSA-N (3-aminoazetidin-1-yl)-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]methanone Chemical compound C1C(N)CN1C(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F AMKMWZPNFOTRDH-UHFFFAOYSA-N 0.000 claims 1
- ZZJMLFCTJLGTEI-UHFFFAOYSA-N (3-aminoazetidin-1-yl)-[4-(2-fluoro-4-iodoanilino)thiophen-3-yl]methanone Chemical compound C1C(N)CN1C(=O)C1=CSC=C1NC1=CC=C(I)C=C1F ZZJMLFCTJLGTEI-UHFFFAOYSA-N 0.000 claims 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- DSIBSRXKQRYPJP-UHFFFAOYSA-N 1,2-oxazole-5-carboxamide Chemical compound NC(=O)C1=CC=NO1 DSIBSRXKQRYPJP-UHFFFAOYSA-N 0.000 claims 1
- OIEUKOXYYRCJOB-UHFFFAOYSA-N 1-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)benzoyl]-n-hydroxyazetidine-2-carboxamide Chemical compound ONC(=O)C1CCN1C(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F OIEUKOXYYRCJOB-UHFFFAOYSA-N 0.000 claims 1
- VGQZTOCHLVGGBK-UHFFFAOYSA-N 1-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)benzoyl]-n-hydroxyazetidine-3-carboxamide Chemical compound C1C(C(=O)NO)CN1C(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F VGQZTOCHLVGGBK-UHFFFAOYSA-N 0.000 claims 1
- UJXSKQZZTUMIPR-UHFFFAOYSA-N 1-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)benzoyl]-n-methyl-n-prop-2-enylazetidine-3-carboxamide Chemical compound C1C(C(=O)N(CC=C)C)CN1C(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F UJXSKQZZTUMIPR-UHFFFAOYSA-N 0.000 claims 1
- OUZFPOWROZRFOA-UHFFFAOYSA-N 1-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)benzoyl]-n-methylazetidine-3-carboxamide Chemical compound C1C(C(=O)NC)CN1C(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F OUZFPOWROZRFOA-UHFFFAOYSA-N 0.000 claims 1
- JNRJARCELIUHEU-UHFFFAOYSA-N 1-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)benzoyl]azetidin-3-one Chemical compound C=1C=C(I)C=C(F)C=1NC1=C(F)C(F)=CC=C1C(=O)N1CC(=O)C1 JNRJARCELIUHEU-UHFFFAOYSA-N 0.000 claims 1
- QYQLVTVZLMBZKM-UHFFFAOYSA-N 1-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)benzoyl]azetidine-2-carboxylic acid Chemical compound OC(=O)C1CCN1C(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F QYQLVTVZLMBZKM-UHFFFAOYSA-N 0.000 claims 1
- KDMCTGAOBPQHRZ-UHFFFAOYSA-N 1-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)benzoyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1C(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F KDMCTGAOBPQHRZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004486 1-methylpiperidin-3-yl group Chemical group CN1CC(CCC1)* 0.000 claims 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- HTJOVUNXGJONIS-UHFFFAOYSA-N 2-(benzylamino)-6-bromo-8-ethyl-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C(C)=C2C=C(Br)C(=O)N(CC)C2=NC=1NCC1=CC=CC=C1 HTJOVUNXGJONIS-UHFFFAOYSA-N 0.000 claims 1
- JMNLUUPZYOLBHN-UHFFFAOYSA-N 2-(ethylamino)-4-methyl-6-(1H-pyrazol-5-yl)-8H-pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1NC2=NC(NCC)=NC(C)=C2C=C1C=1C=CNN=1 JMNLUUPZYOLBHN-UHFFFAOYSA-N 0.000 claims 1
- ZHRYNYKDUYSRGB-UHFFFAOYSA-N 2-(ethylamino)-4-methyl-8-propan-2-yl-6-pyrazol-1-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C(C)C)C2=NC(NCC)=NC(C)=C2C=C1N1C=CC=N1 ZHRYNYKDUYSRGB-UHFFFAOYSA-N 0.000 claims 1
- HSEBQNPXSICMIB-UHFFFAOYSA-N 2-(ethylamino)-4-methyl-8-propan-2-yl-6-thiophen-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C(C)C)C2=NC(NCC)=NC(C)=C2C=C1C1=CC=CS1 HSEBQNPXSICMIB-UHFFFAOYSA-N 0.000 claims 1
- QRJXSWSAFBXPGH-UHFFFAOYSA-N 2-(ethylamino)-6-(furan-3-yl)-4-methyl-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C(C)C)C2=NC(NCC)=NC(C)=C2C=C1C=1C=COC=1 QRJXSWSAFBXPGH-UHFFFAOYSA-N 0.000 claims 1
- CBBFWSMELCDMPZ-UHFFFAOYSA-N 2-(methylamino)acetamide Chemical compound CNCC(N)=O CBBFWSMELCDMPZ-UHFFFAOYSA-N 0.000 claims 1
- KTFDYVNEGTXQCV-UHFFFAOYSA-N 2-Thiophenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CS1 KTFDYVNEGTXQCV-UHFFFAOYSA-N 0.000 claims 1
- GWQBQZWHKVNWAQ-UHFFFAOYSA-N 2-[4-(4-benzylpiperazin-1-yl)anilino]-6-bromo-8-ethyl-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C(C)=C2C=C(Br)C(=O)N(CC)C2=NC=1NC(C=C1)=CC=C1N(CC1)CCN1CC1=CC=CC=C1 GWQBQZWHKVNWAQ-UHFFFAOYSA-N 0.000 claims 1
- AAZQBTDBIDQFOT-UHFFFAOYSA-N 2-[4-(4-benzylpiperazin-1-yl)anilino]-8-ethyl-4-methyl-6-thiophen-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C(C)=C2C=C(C=3SC=CC=3)C(=O)N(CC)C2=NC=1NC(C=C1)=CC=C1N(CC1)CCN1CC1=CC=CC=C1 AAZQBTDBIDQFOT-UHFFFAOYSA-N 0.000 claims 1
- FPWGZOOQOSVFNF-UHFFFAOYSA-N 2-[4-(4-ethylpiperazin-1-yl)anilino]-4-methyl-6-phenyl-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(CC)CCN1C(C=C1)=CC=C1NC1=NC(C)=C(C=C(C=2C=CC=CC=2)C(=O)N2C(C)C)C2=N1 FPWGZOOQOSVFNF-UHFFFAOYSA-N 0.000 claims 1
- GXWZBYLDKUHYMM-UHFFFAOYSA-N 2-[4-(4-ethylpiperazin-1-yl)anilino]-4-methyl-8-propan-2-yl-6-(1h-pyrazol-5-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(CC)CCN1C(C=C1)=CC=C1NC1=NC(C)=C(C=C(C2=NNC=C2)C(=O)N2C(C)C)C2=N1 GXWZBYLDKUHYMM-UHFFFAOYSA-N 0.000 claims 1
- FMKRGZMYBBIDRU-UHFFFAOYSA-N 2-[4-(4-ethylpiperazin-1-yl)anilino]-4-methyl-8-propan-2-yl-6-pyrazol-1-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(CC)CCN1C(C=C1)=CC=C1NC1=NC(C)=C(C=C(N2N=CC=C2)C(=O)N2C(C)C)C2=N1 FMKRGZMYBBIDRU-UHFFFAOYSA-N 0.000 claims 1
- LCQNZXBWUQGXRT-UHFFFAOYSA-N 2-[4-[2-(diethylamino)ethoxy]anilino]-8-ethyl-4-methyl-6-phenylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC1=NC(C)=C(C=C(C=2C=CC=CC=2)C(=O)N2CC)C2=N1 LCQNZXBWUQGXRT-UHFFFAOYSA-N 0.000 claims 1
- HZRBHCGEYZORAK-UHFFFAOYSA-N 2-amino-4-methyl-8-propan-2-yl-6-(1h-pyrazol-5-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C(C)C)C2=NC(N)=NC(C)=C2C=C1C=1C=CNN=1 HZRBHCGEYZORAK-UHFFFAOYSA-N 0.000 claims 1
- QSWPHEWUFGXYPX-UHFFFAOYSA-N 2-amino-8-cyclopentyl-4-methyl-6-(1h-pyrazol-5-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1C(C2=NNC=C2)=CC=2C(C)=NC(N)=NC=2N1C1CCCC1 QSWPHEWUFGXYPX-UHFFFAOYSA-N 0.000 claims 1
- RGHYDLZMTYDBDT-UHFFFAOYSA-N 2-amino-8-ethyl-4-methyl-6-(1H-pyrazol-5-yl)-7-pyrido[2,3-d]pyrimidinone Chemical compound O=C1N(CC)C2=NC(N)=NC(C)=C2C=C1C=1C=CNN=1 RGHYDLZMTYDBDT-UHFFFAOYSA-N 0.000 claims 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- PCVGVJIERNKFME-UHFFFAOYSA-N 2-anilino-6-bromo-8-ethyl-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C(C)=C2C=C(Br)C(=O)N(CC)C2=NC=1NC1=CC=CC=C1 PCVGVJIERNKFME-UHFFFAOYSA-N 0.000 claims 1
- ZSBCYLLGJGQANG-UHFFFAOYSA-N 2-anilino-8-cyclopentyl-4-methyl-6-(1h-pyrazol-5-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=2N(C3CCCC3)C(=O)C(C3=NNC=C3)=CC=2C(C)=NC=1NC1=CC=CC=C1 ZSBCYLLGJGQANG-UHFFFAOYSA-N 0.000 claims 1
- VWDQGKGGOXAPIQ-UHFFFAOYSA-N 2-anilino-8-ethyl-4-methyl-6-phenylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C(C)=C2C=C(C=3C=CC=CC=3)C(=O)N(CC)C2=NC=1NC1=CC=CC=C1 VWDQGKGGOXAPIQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
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-
2007
- 2007-08-16 WO PCT/US2007/018057 patent/WO2008021389A2/en not_active Ceased
- 2007-08-16 CA CA002658725A patent/CA2658725A1/en not_active Abandoned
- 2007-08-16 CN CNA200780038496XA patent/CN101528231A/zh not_active Withdrawn
- 2007-08-16 JP JP2009524671A patent/JP2010500994A/ja active Pending
- 2007-08-16 AU AU2007284562A patent/AU2007284562B2/en not_active Ceased
- 2007-08-16 US US12/373,257 patent/US20100075947A1/en not_active Abandoned
- 2007-08-16 CN CN201510204883.2A patent/CN104784695A/zh active Pending
- 2007-08-16 EP EP07811344A patent/EP2056829B9/en active Active
- 2007-08-16 AT AT07811344T patent/ATE539752T1/de active
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2012
- 2012-08-07 US US13/568,649 patent/US8642584B2/en active Active
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2013
- 2013-05-14 JP JP2013102030A patent/JP2013151570A/ja not_active Withdrawn
- 2013-12-07 US US14/099,939 patent/US20140100215A1/en not_active Abandoned
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2014
- 2014-03-28 JP JP2014067502A patent/JP2014122243A/ja active Pending
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2016
- 2016-02-04 JP JP2016019549A patent/JP2016074743A/ja not_active Withdrawn
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2017
- 2017-10-04 JP JP2017194176A patent/JP2017226702A/ja active Pending
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