JP5480503B2 - ＰＩ３Ｋαのピリドピリミジノン型阻害剤 - Google Patents
ＰＩ３Ｋαのピリドピリミジノン型阻害剤 Download PDFInfo
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- JP5480503B2 JP5480503B2 JP2008534767A JP2008534767A JP5480503B2 JP 5480503 B2 JP5480503 B2 JP 5480503B2 JP 2008534767 A JP2008534767 A JP 2008534767A JP 2008534767 A JP2008534767 A JP 2008534767A JP 5480503 B2 JP5480503 B2 JP 5480503B2
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- Prior art keywords
- amino
- methyl
- phenyl
- optionally substituted
- ethyl
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- 239000003112 inhibitor Substances 0.000 title description 6
- IAAQUOVTPAMQCR-UHFFFAOYSA-N 1h-pyrido[3,2-d]pyrimidin-2-one Chemical compound C1=CC=C2NC(=O)N=CC2=N1 IAAQUOVTPAMQCR-UHFFFAOYSA-N 0.000 title 1
- -1 pyrazol-4-yl Chemical group 0.000 claims description 330
- 150000001875 compounds Chemical class 0.000 claims description 228
- 125000000217 alkyl group Chemical group 0.000 claims description 100
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 95
- 125000003118 aryl group Chemical group 0.000 claims description 79
- 239000000203 mixture Substances 0.000 claims description 78
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 70
- 150000003839 salts Chemical class 0.000 claims description 69
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 64
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 63
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 62
- 238000000034 method Methods 0.000 claims description 62
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 61
- 125000001072 heteroaryl group Chemical group 0.000 claims description 60
- 206010028980 Neoplasm Diseases 0.000 claims description 56
- 125000005843 halogen group Chemical group 0.000 claims description 48
- 239000012453 solvate Substances 0.000 claims description 44
- 125000003545 alkoxy group Chemical group 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 39
- 239000001257 hydrogen Substances 0.000 claims description 38
- 201000011510 cancer Diseases 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 125000001188 haloalkyl group Chemical group 0.000 claims description 29
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 28
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 27
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 26
- 125000003282 alkyl amino group Chemical group 0.000 claims description 24
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 24
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 23
- 239000003814 drug Substances 0.000 claims description 21
- 150000002431 hydrogen Chemical class 0.000 claims description 21
- 125000002252 acyl group Chemical group 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 125000003107 substituted aryl group Chemical group 0.000 claims description 17
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 15
- 125000002431 aminoalkoxy group Chemical group 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 12
- 208000005017 glioblastoma Diseases 0.000 claims description 12
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 11
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 10
- 206010006187 Breast cancer Diseases 0.000 claims description 10
- 208000026310 Breast neoplasm Diseases 0.000 claims description 10
- 206010033128 Ovarian cancer Diseases 0.000 claims description 10
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 10
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
- 125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 claims description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- 201000001441 melanoma Diseases 0.000 claims description 10
- 125000004193 piperazinyl group Chemical group 0.000 claims description 10
- 125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 claims description 10
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 9
- 206010008342 Cervix carcinoma Diseases 0.000 claims description 9
- 206010009944 Colon cancer Diseases 0.000 claims description 9
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 9
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 9
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 9
- 201000010881 cervical cancer Diseases 0.000 claims description 9
- 208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 claims description 9
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 9
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims description 8
- 206010014733 Endometrial cancer Diseases 0.000 claims description 7
- 206010014759 Endometrial neoplasm Diseases 0.000 claims description 7
- 206010060862 Prostate cancer Diseases 0.000 claims description 7
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 claims description 6
- 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 claims description 6
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 6
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 6
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 6
- 208000015634 Rectal Neoplasms Diseases 0.000 claims description 6
- 206010041067 Small cell lung cancer Diseases 0.000 claims description 6
- 208000005718 Stomach Neoplasms Diseases 0.000 claims description 6
- 208000024770 Thyroid neoplasm Diseases 0.000 claims description 6
- 208000029742 colonic neoplasm Diseases 0.000 claims description 6
- 206010017758 gastric cancer Diseases 0.000 claims description 6
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 6
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims description 6
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 6
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims description 6
- 125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 claims description 6
- 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims description 6
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 6
- 125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 claims description 6
- 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 claims description 6
- 206010038038 rectal cancer Diseases 0.000 claims description 6
- 201000001275 rectum cancer Diseases 0.000 claims description 6
- 208000000587 small cell lung carcinoma Diseases 0.000 claims description 6
- 201000011549 stomach cancer Diseases 0.000 claims description 6
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 6
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 6
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 6
- 201000002510 thyroid cancer Diseases 0.000 claims description 6
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 6
- 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 claims description 5
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 5
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 5
- 125000002757 morpholinyl group Chemical group 0.000 claims description 5
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims description 5
- 201000002528 pancreatic cancer Diseases 0.000 claims description 5
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 125000001724 1,2,3-oxadiazol-4-yl group Chemical group [H]C1=C(*)N=NO1 0.000 claims description 4
- 125000004503 1,2,3-oxadiazol-5-yl group Chemical group O1N=NC=C1* 0.000 claims description 4
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 4
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims description 4
- 125000006542 morpholinylalkyl group Chemical group 0.000 claims description 4
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims description 4
- IVPVEGDKEUBQGC-UHFFFAOYSA-N 2-[4-(4-ethylpiperazin-1-yl)anilino]-4-methyl-8-propan-2-yl-6-thiophen-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(CC)CCN1C(C=C1)=CC=C1NC1=NC(C)=C(C=C(C=2SC=CC=2)C(=O)N2C(C)C)C2=N1 IVPVEGDKEUBQGC-UHFFFAOYSA-N 0.000 claims description 3
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 3
- XJNBXNJHYUUBDW-UHFFFAOYSA-N 8-ethyl-2-[4-(4-ethylpiperazin-1-yl)anilino]-6-(3-fluorophenyl)-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(CC)CCN1C(C=C1)=CC=C1NC1=NC(C)=C(C=C(C=2C=C(F)C=CC=2)C(=O)N2CC)C2=N1 XJNBXNJHYUUBDW-UHFFFAOYSA-N 0.000 claims description 3
- UHRXZCZBKZUOOB-UHFFFAOYSA-N 8-ethyl-4-methyl-6-phenyl-2-[4-(2-piperidin-1-ylethoxy)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C(C)=C2C=C(C=3C=CC=CC=3)C(=O)N(CC)C2=NC=1NC(C=C1)=CC=C1OCCN1CCCCC1 UHRXZCZBKZUOOB-UHFFFAOYSA-N 0.000 claims description 3
- 125000005084 alkoxyalkylaminoalkyl group Chemical group 0.000 claims description 3
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- QTTNPSDIKQHKIW-UHFFFAOYSA-N 2-(4-aminoanilino)-8-cyclopentyl-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=2N(C3CCCC3)C(=O)C=CC=2C(C)=NC=1NC1=CC=C(N)C=C1 QTTNPSDIKQHKIW-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- ZNEDYZDWOUKDLS-UHFFFAOYSA-N 2-(cyclopropylamino)-8-ethyl-4-methyl-6-(1h-pyrazol-5-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C(C)=C2C=C(C=3NN=CC=3)C(=O)N(CC)C2=NC=1NC1CC1 ZNEDYZDWOUKDLS-UHFFFAOYSA-N 0.000 claims description 2
- JAYMOLFWOQYXQN-UHFFFAOYSA-N 2-(cyclopropylmethylamino)-8-ethyl-4-methyl-6-(1h-pyrazol-5-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C(C)=C2C=C(C=3NN=CC=3)C(=O)N(CC)C2=NC=1NCC1CC1 JAYMOLFWOQYXQN-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- MGVGASCDBPLAOX-UHFFFAOYSA-N 2-[4-(4-ethylpiperazin-1-yl)anilino]-4-methyl-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(CC)CCN1C(C=C1)=CC=C1NC1=NC(C)=C(C=CC(=O)N2C(C)C)C2=N1 MGVGASCDBPLAOX-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- SNAHPZCYCDEFIJ-UHFFFAOYSA-N 2-anilino-8-cyclopentyl-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=2N(C3CCCC3)C(=O)C=CC=2C(C)=NC=1NC1=CC=CC=C1 SNAHPZCYCDEFIJ-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- GUXQXARJIPRGEG-UHFFFAOYSA-N 6-bromo-2-(cyclohexylamino)-8-ethyl-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C(C)=C2C=C(Br)C(=O)N(CC)C2=NC=1NC1CCCCC1 GUXQXARJIPRGEG-UHFFFAOYSA-N 0.000 claims description 2
- AIELSQNLZXOUOU-UHFFFAOYSA-N 6-bromo-2-(cyclopentylamino)-8-ethyl-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C(C)=C2C=C(Br)C(=O)N(CC)C2=NC=1NC1CCCC1 AIELSQNLZXOUOU-UHFFFAOYSA-N 0.000 claims description 2
- NIQVMNKCATXZOP-UHFFFAOYSA-N 6-bromo-2-[4-(4-ethylpiperazin-1-yl)anilino]-4-methyl-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(CC)CCN1C(C=C1)=CC=C1NC1=NC(C)=C(C=C(Br)C(=O)N2C(C)C)C2=N1 NIQVMNKCATXZOP-UHFFFAOYSA-N 0.000 claims description 2
- NXAJMDSKXCTDLZ-UHFFFAOYSA-N 6-bromo-8-cyclopentyl-2-(4-hydroxyanilino)-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=2N(C3CCCC3)C(=O)C(Br)=CC=2C(C)=NC=1NC1=CC=C(O)C=C1 NXAJMDSKXCTDLZ-UHFFFAOYSA-N 0.000 claims description 2
- MLDPYVPXEDGNCE-UHFFFAOYSA-N 6-bromo-8-ethyl-2-(2-fluoroanilino)-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=C1F MLDPYVPXEDGNCE-UHFFFAOYSA-N 0.000 claims description 2
- JRWPTNNXOLYHTL-UHFFFAOYSA-N 6-bromo-8-ethyl-2-(4-fluoroanilino)-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C(C)=C2C=C(Br)C(=O)N(CC)C2=NC=1NC1=CC=C(F)C=C1 JRWPTNNXOLYHTL-UHFFFAOYSA-N 0.000 claims description 2
- NFAIYTSZZXYUDB-UHFFFAOYSA-N 6-bromo-8-ethyl-2-[4-(4-ethylpiperazin-1-yl)anilino]-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(CC)CCN1C(C=C1)=CC=C1NC1=NC(C)=C(C=C(Br)C(=O)N2CC)C2=N1 NFAIYTSZZXYUDB-UHFFFAOYSA-N 0.000 claims description 2
- SIWZOCORNHHBFC-UHFFFAOYSA-N 6-bromo-8-ethyl-4-methyl-2-(2-morpholin-4-ylethylamino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C(C)=C2C=C(Br)C(=O)N(CC)C2=NC=1NCCN1CCOCC1 SIWZOCORNHHBFC-UHFFFAOYSA-N 0.000 claims description 2
- BUJJXZZBSTYLJG-UHFFFAOYSA-N 6-bromo-8-ethyl-4-methyl-2-(4-morpholin-4-ylanilino)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C(C)=C2C=C(Br)C(=O)N(CC)C2=NC=1NC(C=C1)=CC=C1N1CCOCC1 BUJJXZZBSTYLJG-UHFFFAOYSA-N 0.000 claims description 2
- DQXTYECQBMLSLO-UHFFFAOYSA-N 6-bromo-8-ethyl-4-methyl-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C(C)=C2C=C(Br)C(=O)N(CC)C2=NC=1NC(C=C1)=CC=C1N1CCN(C)CC1 DQXTYECQBMLSLO-UHFFFAOYSA-N 0.000 claims description 2
- SIVGQKWCODHFNW-UHFFFAOYSA-N 8-cyclopentyl-2-(4-fluoroanilino)-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=C(F)C=C1 SIVGQKWCODHFNW-UHFFFAOYSA-N 0.000 claims description 2
- DMQGPHKSCOGPFY-UHFFFAOYSA-N 8-cyclopentyl-2-(4-fluoroanilino)-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=2N(C3CCCC3)C(=O)C=CC=2C(C)=NC=1NC1=CC=C(F)C=C1 DMQGPHKSCOGPFY-UHFFFAOYSA-N 0.000 claims description 2
- QEXNDJIJKQTGBP-UHFFFAOYSA-N 8-cyclopentyl-2-(4-hydroxyanilino)-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=2N(C3CCCC3)C(=O)C=CC=2C(C)=NC=1NC1=CC=C(O)C=C1 QEXNDJIJKQTGBP-UHFFFAOYSA-N 0.000 claims description 2
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| US74371906P | 2006-03-23 | 2006-03-23 | |
| US60/743,719 | 2006-03-23 | ||
| PCT/US2006/039472 WO2007044698A1 (en) | 2005-10-07 | 2006-10-09 | PYRIDOPYRIMIDINONE INHIBITORS OF PI3Kα |
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| JP2014125567A Expired - Fee Related JP6043754B2 (ja) | 2005-10-07 | 2014-06-18 | ＰＩ３Ｋαのピリドピリミジノン型阻害剤 |
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| WO (1) | WO2007044698A1 (https=) |
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| EA016945B1 (ru) * | 2005-10-07 | 2012-08-30 | Экселиксис, Инк. | ПИРИДОПИРИМИДИНОНОВЫЕ ИНГИБИТОРЫ PI3Kα |
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2006
- 2006-10-09 CN CN2012102106887A patent/CN102746298A/zh active Pending
- 2006-10-09 JP JP2008534767A patent/JP5480503B2/ja not_active Expired - Fee Related
- 2006-10-09 EP EP06825665A patent/EP1931670B1/en active Active
- 2006-10-09 US US11/988,859 patent/US8247408B2/en not_active Expired - Fee Related
- 2006-10-09 EA EA201200669A patent/EA201200669A1/ru unknown
- 2006-10-09 AU AU2006302148A patent/AU2006302148B2/en not_active Ceased
- 2006-10-09 WO PCT/US2006/039472 patent/WO2007044698A1/en not_active Ceased
- 2006-10-09 PT PT68257682T patent/PT1940839E/pt unknown
- 2006-10-09 CA CA002624965A patent/CA2624965A1/en not_active Abandoned
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Also Published As
| Publication number | Publication date |
|---|---|
| JP2014221778A (ja) | 2014-11-27 |
| JP6043754B2 (ja) | 2016-12-14 |
| PT1940839E (pt) | 2013-10-10 |
| EA201200669A1 (ru) | 2012-11-30 |
| CN102746298A (zh) | 2012-10-24 |
| JP2009511498A (ja) | 2009-03-19 |
| HK1119696A1 (en) | 2009-03-13 |
| US20090062274A1 (en) | 2009-03-05 |
| JP2013079255A (ja) | 2013-05-02 |
| EP1931670A1 (en) | 2008-06-18 |
| JP2016106088A (ja) | 2016-06-16 |
| CA2624965A1 (en) | 2007-04-19 |
| WO2007044698A1 (en) | 2007-04-19 |
| US8247408B2 (en) | 2012-08-21 |
| EP1931670B1 (en) | 2012-09-12 |
| AU2006302148A1 (en) | 2007-04-19 |
| AU2006302148B2 (en) | 2012-12-06 |
| ZA200802585B (en) | 2009-02-25 |
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