JP2010540458A5 - - Google Patents
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- JP2010540458A5 JP2010540458A5 JP2010526059A JP2010526059A JP2010540458A5 JP 2010540458 A5 JP2010540458 A5 JP 2010540458A5 JP 2010526059 A JP2010526059 A JP 2010526059A JP 2010526059 A JP2010526059 A JP 2010526059A JP 2010540458 A5 JP2010540458 A5 JP 2010540458A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrimidin
- cancer
- morpholinothiazolo
- amine
- alkyl
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 19
- 125000000623 heterocyclic group Chemical group 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 17
- -1 wherein m is 1 Chemical compound 0.000 claims 15
- 125000001072 heteroaryl group Chemical group 0.000 claims 14
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 125000004452 carbocyclyl group Chemical group 0.000 claims 9
- 229910052799 carbon Inorganic materials 0.000 claims 9
- 206010028980 Neoplasm Diseases 0.000 claims 8
- 201000011510 cancer Diseases 0.000 claims 7
- 125000002619 bicyclic group Chemical group 0.000 claims 6
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 5
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 4
- 125000002757 morpholinyl group Chemical group 0.000 claims 4
- 125000004193 piperazinyl group Chemical group 0.000 claims 4
- 125000003386 piperidinyl group Chemical group 0.000 claims 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 4
- 206010009944 Colon cancer Diseases 0.000 claims 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 2
- 201000002528 pancreatic cancer Diseases 0.000 claims 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 2
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 2
- GHIWCRRQTAWFDI-ZDUSSCGKSA-N (2s)-1-[4-[[5-(2-aminopyrimidin-5-yl)-7-morpholin-4-yl-[1,3]thiazolo[5,4-d]pyrimidin-2-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=NC2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2S1 GHIWCRRQTAWFDI-ZDUSSCGKSA-N 0.000 claims 1
- KMKVSCJQCXIOFU-KRWDZBQOSA-N (2s)-2-hydroxy-1-[4-[(7-morpholin-4-yl-5-quinolin-3-yl-[1,3]thiazolo[5,4-d]pyrimidin-2-yl)methyl]piperazin-1-yl]propan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=NC2=C(N3CCOCC3)N=C(C=3C=C4C=CC=CC4=NC=3)N=C2S1 KMKVSCJQCXIOFU-KRWDZBQOSA-N 0.000 claims 1
- NAVFVILLJQALAO-AWEZNQCLSA-N (2s)-2-hydroxy-1-[4-[[5-[2-(methylamino)pyrimidin-5-yl]-7-morpholin-4-yl-[1,3]thiazolo[5,4-d]pyrimidin-2-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1=NC(NC)=NC=C1C1=NC(N2CCOCC2)=C(N=C(CN2CCN(CC2)C(=O)[C@H](C)O)S2)C2=N1 NAVFVILLJQALAO-AWEZNQCLSA-N 0.000 claims 1
- HKUALZOSZZIXFL-UHFFFAOYSA-N 2-[4-[5-(2-aminopyrimidin-5-yl)-7-morpholin-4-yl-[1,3]thiazolo[4,5-d]pyrimidin-2-yl]piperazin-1-yl]ethanol Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=N2)N3CCN(CCO)CC3)C2=N1 HKUALZOSZZIXFL-UHFFFAOYSA-N 0.000 claims 1
- WQXWWQQZDJXVNO-UHFFFAOYSA-N 2-[5-(2-aminopyrimidin-5-yl)-7-morpholin-4-yl-[1,3]thiazolo[4,5-d]pyrimidin-2-yl]propan-2-ol Chemical compound C=12SC(C(C)(O)C)=NC2=NC(C=2C=NC(N)=NC=2)=NC=1N1CCOCC1 WQXWWQQZDJXVNO-UHFFFAOYSA-N 0.000 claims 1
- BKVQEYGHPGUWQD-UHFFFAOYSA-N 2-[5-(2-aminopyrimidin-5-yl)-7-morpholin-4-yl-[1,3]thiazolo[5,4-d]pyrimidin-2-yl]propan-2-ol Chemical compound N1=C2SC(C(C)(O)C)=NC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 BKVQEYGHPGUWQD-UHFFFAOYSA-N 0.000 claims 1
- ZIOBGZDFMKCKGZ-UHFFFAOYSA-N 2-amino-2-methylpropanamide Chemical compound CC(C)(N)C(N)=O ZIOBGZDFMKCKGZ-UHFFFAOYSA-N 0.000 claims 1
- DRYMMXUBDRJPDS-UHFFFAOYSA-N 2-hydroxy-2-methylpropanamide Chemical compound CC(C)(O)C(N)=O DRYMMXUBDRJPDS-UHFFFAOYSA-N 0.000 claims 1
- TZGPACAKMCUCKX-UHFFFAOYSA-N 2-hydroxyacetamide Chemical compound NC(=O)CO TZGPACAKMCUCKX-UHFFFAOYSA-N 0.000 claims 1
- MTEZLAATISORQK-UHFFFAOYSA-N 2-methoxyacetamide Chemical compound COCC(N)=O MTEZLAATISORQK-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- WBJWLCXGPNDRNE-UHFFFAOYSA-N 4-[2-(3-methylsulfonylphenyl)-5-(1h-pyrrolo[2,3-b]pyridin-5-yl)-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]morpholine Chemical compound CS(=O)(=O)C1=CC=CC(C=2SC3=NC(=NC(=C3N=2)N2CCOCC2)C=2C=C3C=CNC3=NC=2)=C1 WBJWLCXGPNDRNE-UHFFFAOYSA-N 0.000 claims 1
- YGYZTMIFPXGRRL-UHFFFAOYSA-N 4-[2-[(4-methylsulfonylpiperazin-1-yl)methyl]-5-(1h-pyrrolo[2,3-b]pyridin-5-yl)-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=NC2=C(N3CCOCC3)N=C(C=3C=C4C=CNC4=NC=3)N=C2S1 YGYZTMIFPXGRRL-UHFFFAOYSA-N 0.000 claims 1
- ZWRGXXOESNIQAX-UHFFFAOYSA-N 4-[2-[(4-methylsulfonylpiperazin-1-yl)methyl]-5-quinolin-3-yl-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=NC2=C(N3CCOCC3)N=C(C=3C=C4C=CC=CC4=NC=3)N=C2S1 ZWRGXXOESNIQAX-UHFFFAOYSA-N 0.000 claims 1
- XWMPLWQFKDVMEW-UHFFFAOYSA-N 4-[5-(1h-indazol-4-yl)-2-[(4-methylsulfonylpiperazin-1-yl)methyl]-[1,3]thiazolo[5,4-d]pyrimidin-7-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=NC2=C(N3CCOCC3)N=C(C=3C=4C=NNC=4C=CC=3)N=C2S1 XWMPLWQFKDVMEW-UHFFFAOYSA-N 0.000 claims 1
- AIZJZJLEDOHHKD-UHFFFAOYSA-N 5-(2,7-dimorpholin-4-yl-[1,3]thiazolo[4,5-d]pyrimidin-5-yl)pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=N2)N3CCOCC3)C2=N1 AIZJZJLEDOHHKD-UHFFFAOYSA-N 0.000 claims 1
- UMSVIVMHIYAPKM-UHFFFAOYSA-N 5-(2-aminopyrimidin-5-yl)-7-morpholin-4-yl-n-(2-morpholin-4-ylethyl)-[1,3]thiazolo[4,5-d]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(NCCN2CCOCC2)=N2)C2=N1 UMSVIVMHIYAPKM-UHFFFAOYSA-N 0.000 claims 1
- YQLKXXRYRSSZRK-UHFFFAOYSA-N 5-(2-aminopyrimidin-5-yl)-7-morpholin-4-yl-n-(4-morpholin-4-ylphenyl)-[1,3]thiazolo[5,4-d]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(N=C(NC=2C=CC(=CC=2)N2CCOCC2)S2)C2=N1 YQLKXXRYRSSZRK-UHFFFAOYSA-N 0.000 claims 1
- CGYKLGPAIOWHQT-UHFFFAOYSA-N 5-(2-aminopyrimidin-5-yl)-7-morpholin-4-yl-n-phenyl-[1,3]thiazolo[5,4-d]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(N=C(NC=2C=CC=CC=2)S2)C2=N1 CGYKLGPAIOWHQT-UHFFFAOYSA-N 0.000 claims 1
- WHLWCBZDOTZYRU-UHFFFAOYSA-N 5-(2-aminopyrimidin-5-yl)-n-(2-methylsulfonylethyl)-7-morpholin-4-yl-[1,3]thiazolo[4,5-d]pyrimidin-2-amine Chemical compound C=12SC(NCCS(=O)(=O)C)=NC2=NC(C=2C=NC(N)=NC=2)=NC=1N1CCOCC1 WHLWCBZDOTZYRU-UHFFFAOYSA-N 0.000 claims 1
- SXCBYWYHMBCUDQ-UHFFFAOYSA-N 5-(2-aminopyrimidin-5-yl)-n-(4-methylsulfonylphenyl)-7-morpholin-4-yl-[1,3]thiazolo[5,4-d]pyrimidin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1NC1=NC2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2S1 SXCBYWYHMBCUDQ-UHFFFAOYSA-N 0.000 claims 1
- WQSMDTDOYOBTOL-UHFFFAOYSA-N 5-(6-aminopyridin-3-yl)-7-morpholin-4-yl-n-phenyl-[1,3]thiazolo[4,5-d]pyrimidin-2-amine Chemical compound C1=NC(N)=CC=C1C1=NC(N2CCOCC2)=C(SC(NC=2C=CC=CC=2)=N2)C2=N1 WQSMDTDOYOBTOL-UHFFFAOYSA-N 0.000 claims 1
- AUQJUYJSLJLZJN-UHFFFAOYSA-N 5-(6-aminopyridin-3-yl)-n-methyl-n-(1-methylpiperidin-4-yl)-7-morpholin-4-yl-[1,3]thiazolo[4,5-d]pyrimidin-2-amine Chemical compound N=1C2=NC(C=3C=NC(N)=CC=3)=NC(N3CCOCC3)=C2SC=1N(C)C1CCN(C)CC1 AUQJUYJSLJLZJN-UHFFFAOYSA-N 0.000 claims 1
- RHOGGEDQTLFJNI-UHFFFAOYSA-N 5-[2-(2-methoxypropan-2-yl)-7-morpholin-4-yl-[1,3]thiazolo[5,4-d]pyrimidin-5-yl]-n-methylpyridin-2-amine Chemical compound C1=NC(NC)=CC=C1C1=NC(N2CCOCC2)=C(N=C(S2)C(C)(C)OC)C2=N1 RHOGGEDQTLFJNI-UHFFFAOYSA-N 0.000 claims 1
- UREIYECXOVPWRE-UHFFFAOYSA-N 5-[2-(2-methoxypropan-2-yl)-7-morpholin-4-yl-[1,3]thiazolo[5,4-d]pyrimidin-5-yl]-n-methylpyrimidin-2-amine Chemical compound C1=NC(NC)=NC=C1C1=NC(N2CCOCC2)=C(N=C(S2)C(C)(C)OC)C2=N1 UREIYECXOVPWRE-UHFFFAOYSA-N 0.000 claims 1
- XQENIIYXTPPOFF-UHFFFAOYSA-N 5-[2-(2-methoxypropan-2-yl)-7-morpholin-4-yl-[1,3]thiazolo[5,4-d]pyrimidin-5-yl]pyrimidin-2-amine Chemical compound N1=C2SC(C(C)(C)OC)=NC2=C(N2CCOCC2)N=C1C1=CN=C(N)N=C1 XQENIIYXTPPOFF-UHFFFAOYSA-N 0.000 claims 1
- VDRORYMZHVKZHC-UHFFFAOYSA-N 5-[2-(3-methylsulfonylphenyl)-7-morpholin-4-yl-[1,3]thiazolo[4,5-d]pyrimidin-5-yl]pyrimidin-2-amine Chemical compound CS(=O)(=O)C1=CC=CC(C=2SC3=C(N4CCOCC4)N=C(N=C3N=2)C=2C=NC(N)=NC=2)=C1 VDRORYMZHVKZHC-UHFFFAOYSA-N 0.000 claims 1
- ADWNCKWNRDFUBF-UHFFFAOYSA-N 5-[2-(3-methylsulfonylphenyl)-7-morpholin-4-yl-[1,3]thiazolo[5,4-d]pyrimidin-5-yl]pyrimidin-2-amine Chemical compound CS(=O)(=O)C1=CC=CC(C=2SC3=NC(=NC(=C3N=2)N2CCOCC2)C=2C=NC(N)=NC=2)=C1 ADWNCKWNRDFUBF-UHFFFAOYSA-N 0.000 claims 1
- WPJUQICNCRUAIN-UHFFFAOYSA-N 5-[2-(4-methoxypyridin-3-yl)-7-morpholin-4-yl-[1,3]thiazolo[4,5-d]pyrimidin-5-yl]pyridin-2-amine Chemical compound COC1=CC=NC=C1C1=NC2=NC(C=3C=NC(N)=CC=3)=NC(N3CCOCC3)=C2S1 WPJUQICNCRUAIN-UHFFFAOYSA-N 0.000 claims 1
- BSSCCGPVFYKTDF-UHFFFAOYSA-N 5-[2-(4-methoxypyridin-3-yl)-7-morpholin-4-yl-[1,3]thiazolo[5,4-d]pyrimidin-5-yl]pyrimidin-2-amine Chemical compound COC1=CC=NC=C1C1=NC2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2S1 BSSCCGPVFYKTDF-UHFFFAOYSA-N 0.000 claims 1
- DTLARHYDABOITR-UHFFFAOYSA-N 5-[2-(4-methylsulfonylpiperazin-1-yl)-7-morpholin-4-yl-[1,3]thiazolo[4,5-d]pyrimidin-5-yl]pyridin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1C1=NC2=NC(C=3C=NC(N)=CC=3)=NC(N3CCOCC3)=C2S1 DTLARHYDABOITR-UHFFFAOYSA-N 0.000 claims 1
- BCHRZDBIEYIBAB-UHFFFAOYSA-N 5-[2-(4-methylsulfonylpiperazin-1-yl)-7-morpholin-4-yl-[1,3]thiazolo[4,5-d]pyrimidin-5-yl]pyrimidin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1C1=NC2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 BCHRZDBIEYIBAB-UHFFFAOYSA-N 0.000 claims 1
- PCFGKAQGPKTVFS-UHFFFAOYSA-N 5-[2-(5-methylsulfonylpyridin-3-yl)-7-morpholin-4-yl-[1,3]thiazolo[5,4-d]pyrimidin-5-yl]pyrimidin-2-amine Chemical compound CS(=O)(=O)C1=CN=CC(C=2SC3=NC(=NC(=C3N=2)N2CCOCC2)C=2C=NC(N)=NC=2)=C1 PCFGKAQGPKTVFS-UHFFFAOYSA-N 0.000 claims 1
- RYFZJOADXBTPLS-UHFFFAOYSA-N 5-[2-(6-aminopyridin-3-yl)-7-morpholin-4-yl-[1,3]thiazolo[5,4-d]pyrimidin-5-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=CC=C1C1=NC2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2S1 RYFZJOADXBTPLS-UHFFFAOYSA-N 0.000 claims 1
- VINXQIDPIWKTDT-UHFFFAOYSA-N 5-[2-[(4-methylsulfonylpiperazin-1-yl)methyl]-7-morpholin-4-yl-[1,3]thiazolo[5,4-d]pyrimidin-5-yl]pyridin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=NC2=C(N3CCOCC3)N=C(C=3C=NC(N)=CC=3)N=C2S1 VINXQIDPIWKTDT-UHFFFAOYSA-N 0.000 claims 1
- VTHKLPPCYKXYCZ-UHFFFAOYSA-N 5-[2-[(4-methylsulfonylpiperazin-1-yl)methyl]-7-morpholin-4-yl-[1,3]thiazolo[5,4-d]pyrimidin-5-yl]pyrimidin-2-amine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=NC2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2S1 VTHKLPPCYKXYCZ-UHFFFAOYSA-N 0.000 claims 1
- CLSLOWZJUFFFHU-UHFFFAOYSA-N 5-[7-morpholin-4-yl-2-(1,3-thiazol-4-yl)-[1,3]thiazolo[4,5-d]pyrimidin-5-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(SC(=N2)C=3N=CSC=3)C2=N1 CLSLOWZJUFFFHU-UHFFFAOYSA-N 0.000 claims 1
- DARMXCIKWOEHNQ-UHFFFAOYSA-N 5-[7-morpholin-4-yl-2-(6-morpholin-4-ylpyridin-3-yl)-[1,3]thiazolo[5,4-d]pyrimidin-5-yl]pyrimidin-2-amine Chemical compound C1=NC(N)=NC=C1C1=NC(N2CCOCC2)=C(N=C(S2)C=3C=NC(=CC=3)N3CCOCC3)C2=N1 DARMXCIKWOEHNQ-UHFFFAOYSA-N 0.000 claims 1
- 208000010507 Adenocarcinoma of Lung Diseases 0.000 claims 1
- 208000003200 Adenoma Diseases 0.000 claims 1
- 206010001233 Adenoma benign Diseases 0.000 claims 1
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- 206010005949 Bone cancer Diseases 0.000 claims 1
- 208000018084 Bone neoplasm 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
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims 1
- 208000004463 Follicular Adenocarcinoma Diseases 0.000 claims 1
- 208000017604 Hodgkin disease Diseases 0.000 claims 1
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 206010023825 Laryngeal cancer Diseases 0.000 claims 1
- 206010062038 Lip neoplasm Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 208000003445 Mouth Neoplasms Diseases 0.000 claims 1
- 208000001894 Nasopharyngeal Neoplasms Diseases 0.000 claims 1
- 206010061306 Nasopharyngeal cancer Diseases 0.000 claims 1
- 206010029260 Neuroblastoma Diseases 0.000 claims 1
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 208000009565 Pharyngeal Neoplasms Diseases 0.000 claims 1
- 206010034811 Pharyngeal cancer Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 208000015634 Rectal Neoplasms Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 206010039491 Sarcoma Diseases 0.000 claims 1
- 201000010208 Seminoma Diseases 0.000 claims 1
- 208000000453 Skin Neoplasms Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 208000024313 Testicular Neoplasms Diseases 0.000 claims 1
- 206010057644 Testis cancer Diseases 0.000 claims 1
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 1
- 206010062129 Tongue neoplasm Diseases 0.000 claims 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 1
- RPPWGRUIPKDGPO-UHFFFAOYSA-N [5-(1h-indazol-4-yl)-7-morpholin-4-yl-[1,3]thiazolo[4,5-d]pyrimidin-2-yl]-(4-methylsulfonylpiperazin-1-yl)methanone Chemical compound C1CN(S(=O)(=O)C)CCN1C(=O)C1=NC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 RPPWGRUIPKDGPO-UHFFFAOYSA-N 0.000 claims 1
- 208000009956 adenocarcinoma Diseases 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 1
- 201000009036 biliary tract cancer Diseases 0.000 claims 1
- 208000020790 biliary tract neoplasm Diseases 0.000 claims 1
- 208000015322 bone marrow disease Diseases 0.000 claims 1
- 201000000220 brain stem cancer Diseases 0.000 claims 1
- 201000007455 central nervous system cancer Diseases 0.000 claims 1
- 201000010881 cervical cancer Diseases 0.000 claims 1
- 230000001886 ciliary effect Effects 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 201000004101 esophageal cancer Diseases 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 208000005017 glioblastoma Diseases 0.000 claims 1
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- SXQFCVDSOLSHOQ-UHFFFAOYSA-N lactamide Chemical compound CC(O)C(N)=O SXQFCVDSOLSHOQ-UHFFFAOYSA-N 0.000 claims 1
- 206010023841 laryngeal neoplasm Diseases 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 208000012987 lip and oral cavity carcinoma Diseases 0.000 claims 1
- 201000006721 lip cancer Diseases 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 201000007270 liver cancer Diseases 0.000 claims 1
- 208000014018 liver neoplasm Diseases 0.000 claims 1
- 201000005249 lung adenocarcinoma Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
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| US97470807P | 2007-09-24 | 2007-09-24 | |
| US60/974,708 | 2007-09-24 | ||
| PCT/US2008/077394 WO2009042607A1 (en) | 2007-09-24 | 2008-09-23 | Thiazolopyrimidine p13k inhibitor compounds and methods of use |
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Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE456836T1 (de) * | 1996-09-04 | 2010-02-15 | Intertrust Tech Corp | Zuverlässige infrastrukturhilfssysteme, verfahren und techniken für sicheren elektronischen handel, elektronische transaktionen, handelsablaufsteuerung und automatisierung, verteilte verarbeitung und rechteverwaltung |
| US7754208B2 (en) | 2001-01-17 | 2010-07-13 | Trubion Pharmaceuticals, Inc. | Binding domain-immunoglobulin fusion proteins |
| US20030133939A1 (en) | 2001-01-17 | 2003-07-17 | Genecraft, Inc. | Binding domain-immunoglobulin fusion proteins |
| AU2006272555B2 (en) | 2005-07-25 | 2012-03-08 | Aptevo Research And Development Llc | B-cell reduction using CD37-specific and CD20-specific binding molecules |
| CN105837690A (zh) | 2006-06-12 | 2016-08-10 | 新兴产品开发西雅图有限公司 | 具有效应功能的单链多价结合蛋白 |
| ATE510841T1 (de) * | 2007-06-12 | 2011-06-15 | Hoffmann La Roche | Thiazoliopyrimidine und ihre verwendung als hemmer der phosphatidylinositol-3 kinase |
| CN101932587A (zh) * | 2007-09-24 | 2010-12-29 | 吉宁特有限公司 | 噻唑并嘧啶pi3k抑制剂化合物及使用方法 |
| GB0721095D0 (en) * | 2007-10-26 | 2007-12-05 | Piramed Ltd | Pharmaceutical compounds |
| WO2009094224A1 (en) | 2008-01-25 | 2009-07-30 | Millennium Pharmaceuticals, Inc. | Thiophenes and their use as phosphatidylinositol 3-kinase (pi3k) inhibitors |
| NZ603059A (en) | 2008-04-11 | 2014-07-25 | Emergent Product Dev Seattle | Cd37 immunotherapeutic and combination with bifunctional chemotherapeutic thereof |
| CN102066365A (zh) * | 2008-06-19 | 2011-05-18 | 米伦纽姆医药公司 | 噻吩或噻唑衍生物和其作为pi3k抑制剂的用途 |
| US8163763B2 (en) * | 2008-07-31 | 2012-04-24 | Genentech, Inc. | Pyrimidine compounds, compositions and methods of use |
| TWI378933B (en) | 2008-10-14 | 2012-12-11 | Daiichi Sankyo Co Ltd | Morpholinopurine derivatives |
| US8796314B2 (en) | 2009-01-30 | 2014-08-05 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| US9090601B2 (en) | 2009-01-30 | 2015-07-28 | Millennium Pharmaceuticals, Inc. | Thiazole derivatives |
| JP2012516329A (ja) | 2009-01-30 | 2012-07-19 | ミレニアム ファーマシューティカルズ， インコーポレイテッド | Ｐｉ３ｋ阻害剤としてのヘテロアリールおよびその使用 |
| EP2923734B1 (en) * | 2009-03-13 | 2018-01-10 | Katholieke Universiteit Leuven, K.U. Leuven R&D | Purine analogues and their use as immunosuppressive agents |
| RS53830B1 (sr) | 2009-04-30 | 2015-06-30 | Glaxo Group Limited | Indazoli supstituisani oksazolom kao inhibitori pi3-kinaze |
| WO2010135493A2 (en) * | 2009-05-20 | 2010-11-25 | Emory University | Alzheimer's disease imaging agents |
| ES2638323T3 (es) * | 2009-05-20 | 2017-10-19 | Glaxosmithkline Llc | Derivados de tiazolopirimidinona como inhibidores de PI3 quinasa |
| MX2011012520A (es) * | 2009-05-27 | 2011-12-12 | Hoffmann La Roche | Compuestos inhibidores de pi3k de pirimidina biciclicos selectivos para p110 delta y metodos de uso de los mismos. |
| SG182247A1 (en) * | 2009-05-27 | 2012-08-30 | Hoffmann La Roche | Bicyclic indole-pyrimidine pi3k inhibitor compounds selective for p110 delta, and methods of use |
| EP2445346A4 (en) * | 2009-06-24 | 2012-12-05 | Genentech Inc | OXOHETEROCYCLIC FUSIONED PYRIMIDINE COMPOUNDS AND COMPOSITIONS AND METHOD FOR THEIR USE |
| ES2567168T3 (es) * | 2009-11-12 | 2016-04-20 | F. Hoffmann-La Roche Ag | Compuestos purina y pirazolopirimidina N7-sustituidos, composiciones y métodos de utilización |
| WO2011058027A2 (en) * | 2009-11-12 | 2011-05-19 | F. Hoffmann-La Roche Ag | N-9-substituted purine compounds, compositions and methods of use |
| AR079814A1 (es) | 2009-12-31 | 2012-02-22 | Otsuka Pharma Co Ltd | Compuestos heterociclicos, composiciones farmaceuticas que los contienen y sus usos |
| WO2011159726A2 (en) | 2010-06-14 | 2011-12-22 | The Scripps Research Institute | Reprogramming of cells to a new fate |
| MX2013000389A (es) * | 2010-07-14 | 2013-03-08 | Hoffmann La Roche | Compuestos de purina selectivos para fosfatidilinositol 3-cinasa p110 delta, y metodods de uso. |
| US9062038B2 (en) | 2010-08-11 | 2015-06-23 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| US8859768B2 (en) | 2010-08-11 | 2014-10-14 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| EP2603214A4 (en) | 2010-08-11 | 2013-12-18 | Millennium Pharm Inc | HETEROARYLE AND USES THEREOF |
| RU2013114352A (ru) | 2010-09-15 | 2014-10-20 | Ф. Хоффманн-Ля Рош Аг | Азабензотиазолы, композиции и способы применения |
| MX2013004003A (es) | 2010-10-13 | 2013-10-01 | Millenium Pharmaceuticals Inc | Heteroarilos y usos de los mismos. |
| KR20140009259A (ko) | 2010-11-19 | 2014-01-22 | 에프. 호프만-라 로슈 아게 | 피라졸로피리딘 및 tyk2 억제제로서 이의 용도 |
| EA026134B1 (ru) | 2010-12-16 | 2017-03-31 | Ф. Хоффманн-Ля Рош Аг | Трициклические ингибиторы pi3k и способы их применения |
| KR101913619B1 (ko) | 2011-06-09 | 2018-12-28 | 리젠 파마슈티컬스 소시에떼 아노님 | Gpr-119의 조절제로서의 신규한 화합물 |
| JP6121658B2 (ja) * | 2011-06-29 | 2017-04-26 | 大塚製薬株式会社 | 治療用化合物、及び関連する使用の方法 |
| CN104350144B (zh) | 2012-05-23 | 2017-08-04 | 弗·哈夫曼-拉罗切有限公司 | 获得和使用内胚层和肝细胞的组合物和方法 |
| US9145411B2 (en) | 2012-08-02 | 2015-09-29 | Asana Biosciences, Llc | Substituted amino-pyrimidine derivatives |
| HK1214533A1 (zh) | 2013-03-15 | 2016-07-29 | 基因泰克公司 | 治疗癌症和预防癌症耐药性的方法 |
| CN106831722B (zh) * | 2013-10-16 | 2019-08-30 | 上海璎黎药业有限公司 | 稠合杂环化合物、其制备方法、药物组合物和用途 |
| HK1251480A1 (zh) | 2015-09-21 | 2019-02-01 | Aptevo Research And Development Llc | Cd3结合多肽 |
| TW201825465A (zh) | 2016-09-23 | 2018-07-16 | 美商基利科學股份有限公司 | 磷脂醯肌醇3-激酶抑制劑 |
| TW201815787A (zh) | 2016-09-23 | 2018-05-01 | 美商基利科學股份有限公司 | 磷脂醯肌醇3-激酶抑制劑 |
| TW201813963A (zh) | 2016-09-23 | 2018-04-16 | 美商基利科學股份有限公司 | 磷脂醯肌醇3-激酶抑制劑 |
| US10919852B2 (en) * | 2017-07-28 | 2021-02-16 | Chemocentryx, Inc. | Immunomodulator compounds |
| US20240150358A1 (en) * | 2020-06-03 | 2024-05-09 | Kineta, Inc. | Purines and methods of their use |
Family Cites Families (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1470356A1 (de) | 1964-01-15 | 1970-04-30 | Thomae Gmbh Dr K | Neue Thieno[3,2-d]pyrimidine und Verfahren zu ihrer Herstellung |
| US3277093A (en) | 1965-08-02 | 1966-10-04 | Searle & Co | (optionally-2-substituted) 4-halophenyl-5, 7-diketo-6-alkylthiazolo[4, 5-d]pyrimidines |
| US3773919A (en) | 1969-10-23 | 1973-11-20 | Du Pont | Polylactide-drug mixtures |
| BE759493A (fr) * | 1969-11-26 | 1971-05-25 | Thomae Gmbh Dr K | Nouvelles 2-(5-nitro-2-furyl)-thieno(3,2-d) pyrimidines et procedes pour les fabriquer |
| US3763156A (en) | 1970-01-28 | 1973-10-02 | Boehringer Sohn Ingelheim | 2-heterocyclic amino-4-morpholinothieno(3,2-d)pyrimidines |
| RO62428A (fr) | 1971-05-04 | 1978-01-15 | Thomae Gmbh Dr K | Procede pour la preparation des thyeno-(3,2-d)-pyrimidines |
| BE791242A (fr) | 1971-11-11 | 1973-05-10 | Thomae Gmbh Dr K | Nouvelles thiazolo(5,4-d)pyrimidines |
| AT321295B (de) | 1971-11-11 | 1975-03-25 | Thomae Gmbh Dr K | Verfahren zur Herstellung von neuen Thiazolo[5,4-d]-pyrimidin-Derivaten und ihren Salzen |
| US5583024A (en) | 1985-12-02 | 1996-12-10 | The Regents Of The University Of California | Recombinant expression of Coleoptera luciferase |
| US5075305A (en) | 1991-03-18 | 1991-12-24 | Warner-Lambert Company | Compound, composition and use |
| WO1993013664A2 (en) | 1992-01-11 | 1993-07-22 | Schering Agrochemicals Limited | Biheterocyclic fungicidal compounds |
| US6274327B1 (en) | 1992-04-13 | 2001-08-14 | Ludwig Institute For Cancer Research | Polypeptides having kinase activity, their preparation and use |
| US5846824A (en) | 1994-02-07 | 1998-12-08 | Ludwig Institute For Cancer Research | Polypeptides having kinase activity, their preparation and use |
| GB9208135D0 (en) | 1992-04-13 | 1992-05-27 | Ludwig Inst Cancer Res | Polypeptides having kinase activity,their preparation and use |
| US5543523A (en) | 1994-11-15 | 1996-08-06 | Regents Of The University Of Minnesota | Method and intermediates for the synthesis of korupensamines |
| JPH08176070A (ja) | 1994-12-19 | 1996-07-09 | Mitsubishi Chem Corp | ジデプシド誘導体及びｐｉ３キナーゼ阻害剤 |
| JPH08175990A (ja) | 1994-12-19 | 1996-07-09 | Mitsubishi Chem Corp | Ｐｉ３キナーゼ阻害剤とその製造法 |
| JPH08336393A (ja) | 1995-04-13 | 1996-12-24 | Mitsubishi Chem Corp | 光学活性なγ−置換−β−ヒドロキシ酪酸エステルの製造法 |
| AUPO903897A0 (en) | 1997-09-08 | 1997-10-02 | Commonwealth Scientific And Industrial Research Organisation | Organic boronic acid derivatives |
| US6602677B1 (en) | 1997-09-19 | 2003-08-05 | Promega Corporation | Thermostable luciferases and methods of production |
| SK6652000A3 (en) | 1997-11-11 | 2002-05-09 | Pfizer Prod Inc | Thienopyrimidine and thienopyridine derivatives useful as anticancer agents |
| US6187777B1 (en) | 1998-02-06 | 2001-02-13 | Amgen Inc. | Compounds and methods which modulate feeding behavior and related diseases |
| US6232320B1 (en) | 1998-06-04 | 2001-05-15 | Abbott Laboratories | Cell adhesion-inhibiting antiinflammatory compounds |
| AU4157500A (en) * | 1999-03-26 | 2000-10-16 | Astrazeneca Ab | Novel compounds |
| JP2001097979A (ja) * | 1999-07-28 | 2001-04-10 | Takeda Chem Ind Ltd | 縮合複素環化合物、その製造法および用途 |
| JP2001247477A (ja) | 2000-03-03 | 2001-09-11 | Teikoku Hormone Mfg Co Ltd | 抗腫瘍剤 |
| US6403588B1 (en) | 2000-04-27 | 2002-06-11 | Yamanouchi Pharmaceutical Co., Ltd. | Imidazopyridine derivatives |
| US6608053B2 (en) | 2000-04-27 | 2003-08-19 | Yamanouchi Pharmaceutical Co., Ltd. | Fused heteroaryl derivatives |
| US7141576B2 (en) | 2001-01-16 | 2006-11-28 | Smithkline Beecham (Cork) Limited | Cancer treatment method |
| WO2003018057A1 (en) | 2001-07-26 | 2003-03-06 | Santen Pharmaceutical Co., Ltd. | Remedy for glaucoma comprising as the active ingredient compound having pi3 kinase inhibitory effect |
| AU2002349912A1 (en) | 2001-10-24 | 2003-05-06 | Iconix Pharmaceuticals, Inc. | Modulators of phosphoinositide 3-kinase |
| AU2002357667A1 (en) | 2001-10-24 | 2003-05-06 | Iconix Pharmaceuticals, Inc. | Modulators of phosphoinositide 3-kinase |
| AU2002356871A1 (en) | 2001-10-30 | 2003-05-12 | Pharmacia Corporation | Heteroaromatic carboxamide derivatives for the treatment of inflammation |
| US20040092561A1 (en) | 2002-11-07 | 2004-05-13 | Thomas Ruckle | Azolidinone-vinyl fused -benzene derivatives |
| EP1531813A1 (en) | 2002-07-10 | 2005-05-25 | Applied Research Systems ARS Holding N.V. | Use of compounds for increasing spermatozoa motility |
| MXPA05000453A (es) | 2002-07-10 | 2005-03-23 | Applied Research Systems | Derivados de benceno fusionados a azolidinona-vinilo. |
| WO2004017950A2 (en) | 2002-08-22 | 2004-03-04 | Piramed Limited | Phosphadidylinositol 3,5-biphosphate inhibitors as anti-viral agents |
| ES2217956B1 (es) * | 2003-01-23 | 2006-04-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de 4-aminotieno(2,3-d)pirimidin-6-carbonitrilo. |
| EP1687306A1 (en) | 2003-11-14 | 2006-08-09 | MERCK SHARP & DOHME LTD. | Bicyclic pyrimidin-4-(3h)-ones and analogues and derivatives thereof which modulate the function of the vanilloid-1 receptor (vr1) |
| GB0412467D0 (en) * | 2004-06-04 | 2004-07-07 | Astrazeneca Ab | Chemical compounds |
| GB0423653D0 (en) | 2004-10-25 | 2004-11-24 | Piramed Ltd | Pharmaceutical compounds |
| WO2006096338A1 (en) | 2005-03-04 | 2006-09-14 | Bayer Healthcare Ag | 1,3-thiazole-5-carboxamides useful as cancer chemotherapeutic agents |
| GB0508471D0 (en) * | 2005-04-26 | 2005-06-01 | Celltech R&D Ltd | Therapeutic agents |
| US7605154B2 (en) | 2005-08-08 | 2009-10-20 | Janssen Pharmaceutica N.V. | Substituted Thiazolo [4,5-d]pyrimidines as protein kinase inhibitors |
| PL2041139T3 (pl) * | 2006-04-26 | 2012-05-31 | Hoffmann La Roche | Związki farmaceutyczne |
| KR101533461B1 (ko) | 2006-04-26 | 2015-07-02 | 에프. 호프만-라 로슈 아게 | Ｐｉ３ｋ저해제로 유용한 티에노［3,2-ｄ］피리미딘 유도체 |
| KR20090021155A (ko) | 2006-04-26 | 2009-02-27 | 에프. 호프만-라 로슈 아게 | Ｐｉ3ｋ 억제제로서의 피리미딘 유도체 |
| AU2007243466B2 (en) | 2006-04-26 | 2012-01-19 | F. Hoffmann-La Roche Ag | Phosphoinositide 3-kinase inhibitor compounds and pharmaceutical compositions containing them |
| PE20081679A1 (es) | 2006-12-07 | 2008-12-18 | Hoffmann La Roche | Compuestos del inhibidor de fosfoinositida 3-cinasa y metodos de uso |
| CA2671845C (en) | 2006-12-07 | 2015-03-24 | Genentech, Inc. | Phosphoinositide 3-kinase inhibitor compounds and methods of use |
| WO2008152387A1 (en) | 2007-06-12 | 2008-12-18 | F.Hoffmann-La Roche Ag | Quinazoline derivatives as pi3 kinase inhibitors |
| ATE510841T1 (de) * | 2007-06-12 | 2011-06-15 | Hoffmann La Roche | Thiazoliopyrimidine und ihre verwendung als hemmer der phosphatidylinositol-3 kinase |
| WO2008152394A1 (en) | 2007-06-12 | 2008-12-18 | F.Hoffmann-La Roche Ag | Pharmaceutical compounds |
| CN101932587A (zh) | 2007-09-24 | 2010-12-29 | 吉宁特有限公司 | 噻唑并嘧啶pi3k抑制剂化合物及使用方法 |
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- 2008-09-23 ES ES08832932T patent/ES2399774T3/es active Active
- 2008-09-23 US US12/236,317 patent/US7893059B2/en active Active
- 2008-09-23 EP EP08832932A patent/EP2207781B1/en active Active
- 2008-09-23 JP JP2010526059A patent/JP5736171B2/ja active Active
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