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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| EP (1) | EP2207781B1 (https=) |
| JP (1) | JP5736171B2 (https=) |
| CN (1) | CN101932587A (https=) |
| CA (1) | CA2704711C (https=) |
| ES (1) | ES2399774T3 (https=) |
| WO (1) | WO2009042607A1 (https=) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1693804B1 (en) * | 1996-09-04 | 2009-11-11 | Intertrust Technologies Corp. | Trusted infrastructure support systems, methods and techniques for secure electronic commerce, electronic transactions, commerce process control and automation, distributed computing and rights management |
| 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 |
| HRP20140338T1 (hr) | 2005-07-25 | 2014-06-20 | Emergent Product Development Seattle, Llc | Smanjenje broja b-stanica upotrebom molekula koje se specifiäśno vežu na cd37 i cd20 |
| WO2007146968A2 (en) | 2006-06-12 | 2007-12-21 | Trubion Pharmaceuticals, Inc. | Single-chain multivalent binding proteins with effector function |
| US7893060B2 (en) * | 2007-06-12 | 2011-02-22 | F. Hoffmann-La Roche Ag | Thiazolopyrimidines and their use as inhibitors of phosphatidylinositol-3 kinase |
| WO2009042607A1 (en) * | 2007-09-24 | 2009-04-02 | Genentech, Inc. | Thiazolopyrimidine p13k inhibitor compounds and methods of use |
| GB0721095D0 (en) * | 2007-10-26 | 2007-12-05 | Piramed Ltd | Pharmaceutical compounds |
| JP5581219B2 (ja) | 2008-01-25 | 2014-08-27 | 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 | チオフェンおよびホスファチジルイノシトール３−キナーゼ（ｐｉ３ｋ）阻害薬としてのその使用 |
| EP2365003A1 (en) | 2008-04-11 | 2011-09-14 | Emergent Product Development Seattle, LLC | CD37 immunotherapeutic and combination with bifunctional chemotherapeutic thereof |
| JP5596026B2 (ja) * | 2008-06-19 | 2014-09-24 | 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 | チオフェン又はチアゾール誘導体及びｐｉ３ｋ阻害剤としてのそれらの使用 |
| AR073354A1 (es) * | 2008-07-31 | 2010-11-03 | Genentech Inc | Compuestos de pirimidina, composiciones farmaceuticas y su uso en el tratamiento del cancer. |
| 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 |
| WO2010090716A1 (en) | 2009-01-30 | 2010-08-12 | Millennium Pharmaceuticals, Inc. | Heteroaryls and their use as pi3k inhibitors |
| ES2665277T3 (es) | 2009-03-13 | 2018-04-25 | Katholieke Universiteit Leuven K.U. Leuven R&D | Análogos de purina y su uso como agentes inmunosupresores |
| WO2010125082A1 (en) | 2009-04-30 | 2010-11-04 | Glaxo Group Limited | Oxazole substituted indazoles as pi3-kinase inhibitors |
| WO2010135493A2 (en) * | 2009-05-20 | 2010-11-25 | Emory University | Alzheimer's disease imaging agents |
| US8410095B2 (en) * | 2009-05-20 | 2013-04-02 | Glaxosmithkline Llc | Thiazolopyrimidinone derivatives as PI3 kinase inhibitors |
| CA2772371A1 (en) | 2009-05-27 | 2010-12-02 | F. Hoffmann-La Roche Ag | Bicyclic indole-pyrimidine pi3k inhibitor compounds selective for p110 delta, and methods of use |
| CN102459272B (zh) * | 2009-05-27 | 2014-08-06 | 健泰科生物技术公司 | 对P110δ具有选择性的为PI3K抑制剂的二环嘧啶化合物和使用方法 |
| SG176959A1 (en) * | 2009-06-24 | 2012-01-30 | Genentech Inc | Oxo-heterocycle fused pyrimidine compounds, compositions and methods of use |
| WO2011058027A2 (en) * | 2009-11-12 | 2011-05-19 | F. Hoffmann-La Roche Ag | N-9-substituted purine compounds, compositions and methods of use |
| CN102712642B (zh) * | 2009-11-12 | 2015-08-12 | 霍夫曼-拉罗奇有限公司 | N-7取代的嘌呤和吡唑并嘧啶化合物、组合物和使用方法 |
| AR079814A1 (es) | 2009-12-31 | 2012-02-22 | Otsuka Pharma Co Ltd | Compuestos heterociclicos, composiciones farmaceuticas que los contienen y sus usos |
| EP3399026B1 (en) | 2010-06-14 | 2024-06-26 | The Scripps Research Institute | Reprogramming of cells to a new fate |
| JP5555378B2 (ja) * | 2010-07-14 | 2014-07-23 | エフ．ホフマン−ラ ロシュ アーゲー | Ｐｉ３ｋｐ１１０デルタに選択的なプリン化合物とその使用の方法 |
| WO2012021611A1 (en) | 2010-08-11 | 2012-02-16 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| MX2013001660A (es) | 2010-08-11 | 2013-06-03 | Millenium Pharmaceuticals Inc | Heteroarilos y usos de los mismos. |
| US8859768B2 (en) | 2010-08-11 | 2014-10-14 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| MX2013003019A (es) * | 2010-09-15 | 2013-05-28 | Hoffmann La Roche | Compuestos de azabenzotiazol, composiciones y metodos de uso. |
| TW201307309A (zh) | 2010-10-13 | 2013-02-16 | Millennium Pharm Inc | 雜芳基化合物及其用途 |
| MX2013005445A (es) | 2010-11-19 | 2013-07-29 | Hoffmann La Roche | Pirazolopiridinas y el uso de pirazolopiridinas como inhibidores de tirosina cinasa 2 (tyk2). |
| CN103313989B (zh) | 2010-12-16 | 2016-05-04 | 霍夫曼-拉罗奇有限公司 | 三环pi3k抑制剂化合物和使用方法 |
| 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 |
| JP6301316B2 (ja) | 2012-05-23 | 2018-03-28 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | 内胚葉細胞および肝実質細胞の組成物ならびにそれらの細胞を入手および使用する方法 |
| US9145411B2 (en) | 2012-08-02 | 2015-09-29 | Asana Biosciences, Llc | Substituted amino-pyrimidine derivatives |
| WO2014144850A1 (en) | 2013-03-15 | 2014-09-18 | Genentech, Inc. | Methods of treating cancer and preventing cancer drug resistance |
| NZ718487A (en) * | 2013-10-16 | 2020-01-31 | Shanghai Yingli Pharm Co Ltd | Fused heterocyclic compound, preparation method therefor, pharmaceutical composition, and uses thereof |
| EP3352760B1 (en) | 2015-09-21 | 2026-03-11 | Aptevo Research and Development LLC | Cd3 binding polypeptides |
| 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 |
| 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 |
| 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 |
| AU2018306619B2 (en) * | 2017-07-28 | 2022-06-02 | Chemocentryx, Inc. | Immunomodulator compounds |
| EP4161519A4 (en) * | 2020-06-03 | 2024-07-17 | Yumanity Therapeutics, Inc. | PURINES AND METHODS OF 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 |
| US5846824A (en) | 1994-02-07 | 1998-12-08 | Ludwig Institute For Cancer Research | Polypeptides having kinase activity, their preparation and use |
| US6274327B1 (en) | 1992-04-13 | 2001-08-14 | 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 |
| 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 |
| 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 |
| 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 |
| CA2309690A1 (en) | 1997-11-11 | 1999-05-20 | Pfizer Products 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 |
| US6518286B1 (en) * | 1999-03-26 | 2003-02-11 | Astrazeneca Ab | 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 |
| US6608053B2 (en) | 2000-04-27 | 2003-08-19 | Yamanouchi Pharmaceutical Co., Ltd. | Fused heteroaryl derivatives |
| US6403588B1 (en) | 2000-04-27 | 2002-06-11 | Yamanouchi Pharmaceutical Co., Ltd. | Imidazopyridine derivatives |
| DE60203260T2 (de) | 2001-01-16 | 2006-02-02 | Glaxo Group Ltd., Greenford | Pharmazeutische kombination, die ein 4-chinazolinamin und paclitaxel, carboplatin oder vinorelbin enthält, zur behandlung von krebs |
| US20040242545A1 (en) | 2001-07-26 | 2004-12-02 | Santen Phamaceutical Co., Ltd. | Remedy for glaucoma comprising as the active ingredient compound having p13 kinase inhibitory effect |
| AU2002349912A1 (en) | 2001-10-24 | 2003-05-06 | Iconix Pharmaceuticals, Inc. | Modulators of phosphoinositide 3-kinase |
| US6894055B2 (en) | 2001-10-24 | 2005-05-17 | Iconix Pharmaceuticals Inc. | Thieno-2′,3′ -5,6pyrimido[3,4-A]-1,2,4-triazole derivatives as modulators of phoshoinositide 3-kinase |
| AU2002356871A1 (en) | 2001-10-30 | 2003-05-12 | Pharmacia Corporation | Heteroaromatic carboxamide derivatives for the treatment of inflammation |
| CN1681811B (zh) | 2002-07-10 | 2010-05-26 | 默克雪兰诺有限公司 | 唑烷酮-乙烯基稠合的-苯衍生物 |
| US20040092561A1 (en) | 2002-11-07 | 2004-05-13 | Thomas Ruckle | Azolidinone-vinyl fused -benzene derivatives |
| JP2006500327A (ja) | 2002-07-10 | 2006-01-05 | アプライド リサーチ システムズ エーアールエス ホールディング ナームロゼ フェンノートシャップ | 精子の運動性を増大させるための化合物の使用 |
| 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. |
| WO2005049613A1 (en) | 2003-11-14 | 2005-06-02 | Merck Sharp & Dohme Limited | 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 |
| CA2600039A1 (en) | 2005-03-04 | 2006-09-14 | Bayer Pharmaceuticals Corporation | 1,3-thiazole-5-carboxamides useful as cancer chemotherapeutic agents |
| GB0508471D0 (en) * | 2005-04-26 | 2005-06-01 | Celltech R&D Ltd | Therapeutic agents |
| AU2006278627B2 (en) * | 2005-08-08 | 2011-08-18 | Janssen Pharmaceutica, N.V. | Thiazolopyrimidine kinase inhibitors |
| CN101511840A (zh) | 2006-04-26 | 2009-08-19 | 吉宁特有限公司 | 磷酸肌醇3-激酶抑制剂化合物及其使用方法 |
| RU2008141356A (ru) | 2006-04-26 | 2010-06-10 | Ф. Хоффманн-Ля Рош Аг (Ch) | Производные пиримидина в качестве ингибиторов фосфатидилинозитол-3-киназы (pi3k) |
| MX2008013578A (es) | 2006-04-26 | 2009-03-23 | Hoffmann La Roche | Derivados de tieno [3,2-d]pirimidina utiles como inhibidores de fosfatidilinositol 3-cinasa(p13k). |
| TWI498332B (zh) | 2006-04-26 | 2015-09-01 | Hoffmann La Roche | 作為pi3k抑制劑之嘧啶衍生物及相關製備方法、醫藥組合物、用途、套組及產物 |
| ES2571028T3 (es) | 2006-12-07 | 2016-05-23 | Genentech Inc | Compuestos inhibidores de fosfoinositida 3-cinasa y métodos de uso |
| WO2008070740A1 (en) | 2006-12-07 | 2008-06-12 | F.Hoffmann-La Roche Ag | Phosphoinositide 3-kinase inhibitor compounds and methods of use |
| WO2008152394A1 (en) | 2007-06-12 | 2008-12-18 | F.Hoffmann-La Roche Ag | Pharmaceutical compounds |
| US7893060B2 (en) | 2007-06-12 | 2011-02-22 | F. Hoffmann-La Roche Ag | Thiazolopyrimidines and their use as inhibitors of phosphatidylinositol-3 kinase |
| WO2008152387A1 (en) | 2007-06-12 | 2008-12-18 | F.Hoffmann-La Roche Ag | Quinazoline derivatives as pi3 kinase inhibitors |
| WO2009042607A1 (en) * | 2007-09-24 | 2009-04-02 | Genentech, Inc. | Thiazolopyrimidine p13k inhibitor compounds and methods of use |
-
2008
- 2008-09-23 WO PCT/US2008/077394 patent/WO2009042607A1/en not_active Ceased
- 2008-09-23 EP EP08832932A patent/EP2207781B1/en active Active
- 2008-09-23 JP JP2010526059A patent/JP5736171B2/ja active Active
- 2008-09-23 CN CN2008801184715A patent/CN101932587A/zh active Pending
- 2008-09-23 US US12/236,317 patent/US7893059B2/en active Active
- 2008-09-23 CA CA2704711A patent/CA2704711C/en not_active Expired - Fee Related
- 2008-09-23 ES ES08832932T patent/ES2399774T3/es active Active
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2011
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