JP2010540458A5 - - Google Patents
Download PDFInfo
- Publication number
- 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
Links
- 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
- 201000001441 melanoma Diseases 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- GIBKZOSYXQKPJS-UHFFFAOYSA-N n,n-dimethyl-5-[2-[(4-methylsulfonylpiperazin-1-yl)methyl]-7-morpholin-4-yl-[1,3]thiazolo[5,4-d]pyrimidin-5-yl]pyrimidin-2-amine Chemical class C1=NC(N(C)C)=NC=C1C1=NC(N2CCOCC2)=C(N=C(CN2CCN(CC2)S(C)(=O)=O)S2)C2=N1 GIBKZOSYXQKPJS-UHFFFAOYSA-N 0.000 claims 1
- FABZXXJETVNBBX-UHFFFAOYSA-N n-(hydrazinecarbonyl)acetamide Chemical compound CC(=O)NC(=O)NN FABZXXJETVNBBX-UHFFFAOYSA-N 0.000 claims 1
- PNQDMCRYXDMLFG-UHFFFAOYSA-N n-[4-[5-(2-aminopyrimidin-5-yl)-7-morpholin-4-yl-[1,3]thiazolo[5,4-d]pyrimidin-2-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C1=NC2=C(N3CCOCC3)N=C(C=3C=NC(N)=NC=3)N=C2S1 PNQDMCRYXDMLFG-UHFFFAOYSA-N 0.000 claims 1
- XEPVLJPUHRFIIX-UHFFFAOYSA-N n-[[3-[7-morpholin-4-yl-5-(1h-pyrrolo[2,3-b]pyridin-5-yl)-[1,3]thiazolo[5,4-d]pyrimidin-2-yl]phenyl]methyl]methanesulfonamide Chemical compound CS(=O)(=O)NCC1=CC=CC(C=2SC3=NC(=NC(=C3N=2)N2CCOCC2)C=2C=C3C=CNC3=NC=2)=C1 XEPVLJPUHRFIIX-UHFFFAOYSA-N 0.000 claims 1
- PIBUTYAFRVVKIR-UHFFFAOYSA-N n-methyl-5-[2-(3-methylsulfonylphenyl)-7-morpholin-4-yl-[1,3]thiazolo[5,4-d]pyrimidin-5-yl]pyridin-2-amine Chemical compound C1=NC(NC)=CC=C1C1=NC(N2CCOCC2)=C(N=C(S2)C=3C=C(C=CC=3)S(C)(=O)=O)C2=N1 PIBUTYAFRVVKIR-UHFFFAOYSA-N 0.000 claims 1
- VUNNDGDSXJZAIL-UHFFFAOYSA-N n-methyl-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 C1=NC(NC)=CC=C1C1=NC(N2CCOCC2)=C(N=C(CN2CCN(CC2)S(C)(=O)=O)S2)C2=N1 VUNNDGDSXJZAIL-UHFFFAOYSA-N 0.000 claims 1
- ISOCGWGJSHGFAT-UHFFFAOYSA-N n-methyl-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 C1=NC(NC)=NC=C1C1=NC(N2CCOCC2)=C(N=C(CN2CCN(CC2)S(C)(=O)=O)S2)C2=N1 ISOCGWGJSHGFAT-UHFFFAOYSA-N 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 206010038038 rectal cancer Diseases 0.000 claims 1
- 201000001275 rectum cancer Diseases 0.000 claims 1
- 125000006413 ring segment Chemical group 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 201000000849 skin cancer Diseases 0.000 claims 1
- 208000000649 small cell carcinoma Diseases 0.000 claims 1
- 201000002314 small intestine cancer Diseases 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 201000003120 testicular cancer Diseases 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 201000002510 thyroid cancer Diseases 0.000 claims 1
- 208000030901 thyroid gland follicular carcinoma Diseases 0.000 claims 1
- 201000006134 tongue cancer Diseases 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 201000005112 urinary bladder cancer Diseases 0.000 claims 1
- 230000001720 vestibular Effects 0.000 claims 1
- 0 *c(nc1N2CCOCC2)nc([s]2)c1nc2I Chemical compound *c(nc1N2CCOCC2)nc([s]2)c1nc2I 0.000 description 39
- WVWNQPALSDVRTJ-UHFFFAOYSA-N Cc1ccc(CCNC2=O)c2c1 Chemical compound Cc1ccc(CCNC2=O)c2c1 WVWNQPALSDVRTJ-UHFFFAOYSA-N 0.000 description 4
- WUQQKWIILPEEKY-UHFFFAOYSA-N Cc1ccc(cncn2)c2c1 Chemical compound Cc1ccc(cncn2)c2c1 WUQQKWIILPEEKY-UHFFFAOYSA-N 0.000 description 4
- OSRARURJYPOUOV-UHFFFAOYSA-N Cc1ccc2nccnc2c1 Chemical compound Cc1ccc2nccnc2c1 OSRARURJYPOUOV-UHFFFAOYSA-N 0.000 description 4
- HXQDSHSATAEREW-UHFFFAOYSA-N Cc(cc1)cc(C2)c1NC2=O Chemical compound Cc(cc1)cc(C2)c1NC2=O HXQDSHSATAEREW-UHFFFAOYSA-N 0.000 description 2
- DYBFIAMWRDJKBZ-UHFFFAOYSA-N Cc(cc1)cc(C=N2)c1NC2=O Chemical compound Cc(cc1)cc(C=N2)c1NC2=O DYBFIAMWRDJKBZ-UHFFFAOYSA-N 0.000 description 2
- DKNXPCXIGGIJNY-UHFFFAOYSA-N Cc(cc1)cc(CC2)c1NC2=O Chemical compound Cc(cc1)cc(CC2)c1NC2=O DKNXPCXIGGIJNY-UHFFFAOYSA-N 0.000 description 2
- YYNMTNKYXHARBB-UHFFFAOYSA-N Cc(cc1)nc2c1nccn2 Chemical compound Cc(cc1)nc2c1nccn2 YYNMTNKYXHARBB-UHFFFAOYSA-N 0.000 description 2
- MHXGPPCRUZYICQ-UHFFFAOYSA-N Cc(nc1)cc2c1ncnc2 Chemical compound Cc(nc1)cc2c1ncnc2 MHXGPPCRUZYICQ-UHFFFAOYSA-N 0.000 description 2
- QOMQVYYQBYOOMQ-UHFFFAOYSA-N Cc1cc(cccn2)c2nc1 Chemical compound Cc1cc(cccn2)c2nc1 QOMQVYYQBYOOMQ-UHFFFAOYSA-N 0.000 description 2
- ZLTCEYHTNOZGIS-UHFFFAOYSA-N Cc1ccc(C=CNC2=O)c2c1 Chemical compound Cc1ccc(C=CNC2=O)c2c1 ZLTCEYHTNOZGIS-UHFFFAOYSA-N 0.000 description 2
- BFCDUCCWAPLDJQ-UHFFFAOYSA-N Cc1ccc(CC(N2)=O)c2c1 Chemical compound Cc1ccc(CC(N2)=O)c2c1 BFCDUCCWAPLDJQ-UHFFFAOYSA-N 0.000 description 2
- ONYNOPPOVKYGRS-UHFFFAOYSA-N Cc1ccc(cc[nH]2)c2c1 Chemical compound Cc1ccc(cc[nH]2)c2c1 ONYNOPPOVKYGRS-UHFFFAOYSA-N 0.000 description 2
- HMMPHXCOTBASBC-UHFFFAOYSA-N Cc1ccc(cn[nH]2)c2c1 Chemical compound Cc1ccc(cn[nH]2)c2c1 HMMPHXCOTBASBC-UHFFFAOYSA-N 0.000 description 2
- DTBDAFLSBDGPEA-UHFFFAOYSA-N Cc1cnc(cccc2)c2c1 Chemical compound Cc1cnc(cccc2)c2c1 DTBDAFLSBDGPEA-UHFFFAOYSA-N 0.000 description 2
- ABGOJEHSELXHTI-UHFFFAOYSA-N Cc1cnc(cccn2)c2c1 Chemical compound Cc1cnc(cccn2)c2c1 ABGOJEHSELXHTI-UHFFFAOYSA-N 0.000 description 2
- BKUIGEOFJPSULO-UHFFFAOYSA-N Clc(nc1N2CCOCC2)nc([s]2)c1nc2I Chemical compound Clc(nc1N2CCOCC2)nc([s]2)c1nc2I BKUIGEOFJPSULO-UHFFFAOYSA-N 0.000 description 2
- UDOQXGHEEZHFAF-UHFFFAOYSA-N CC(C)Cc(nc1)cnc1S Chemical compound CC(C)Cc(nc1)cnc1S UDOQXGHEEZHFAF-UHFFFAOYSA-N 0.000 description 1
- MCYAWSWJUQZCEF-UHFFFAOYSA-N CC(N1CCN(CC#C[IH]C)CC1)=O Chemical compound CC(N1CCN(CC#C[IH]C)CC1)=O MCYAWSWJUQZCEF-UHFFFAOYSA-N 0.000 description 1
- QJFGPBJMAWBKKA-UHFFFAOYSA-N CC(c(cccc1)c1N)=N Chemical compound CC(c(cccc1)c1N)=N QJFGPBJMAWBKKA-UHFFFAOYSA-N 0.000 description 1
- BMGORWDCSBPJJE-UHFFFAOYSA-N CC(c1c(N)ncnc1)=N Chemical compound CC(c1c(N)ncnc1)=N BMGORWDCSBPJJE-UHFFFAOYSA-N 0.000 description 1
- YECGWFSMGZGRHY-UHFFFAOYSA-N CSCc1cnc(N)nc1 Chemical compound CSCc1cnc(N)nc1 YECGWFSMGZGRHY-UHFFFAOYSA-N 0.000 description 1
- QOKFHFUSIPXAJO-UHFFFAOYSA-N Cc(c(OC)n1)cnc1OC Chemical compound Cc(c(OC)n1)cnc1OC QOKFHFUSIPXAJO-UHFFFAOYSA-N 0.000 description 1
- FDIKLGRIRWGUFH-UHFFFAOYSA-N Cc(cc1)c(C(F)(F)F)nc1N Chemical compound Cc(cc1)c(C(F)(F)F)nc1N FDIKLGRIRWGUFH-UHFFFAOYSA-N 0.000 description 1
- UZAOIPZZPZCFES-UHFFFAOYSA-N Cc(cc1)c(C)nc1N Chemical compound Cc(cc1)c(C)nc1N UZAOIPZZPZCFES-UHFFFAOYSA-N 0.000 description 1
- CMBSSVKZOPZBKW-UHFFFAOYSA-N Cc(cc1)cnc1N Chemical compound Cc(cc1)cnc1N CMBSSVKZOPZBKW-UHFFFAOYSA-N 0.000 description 1
- ASYFGSIOATXWJA-UHFFFAOYSA-N Cc(cc1)cnc1NC Chemical compound Cc(cc1)cnc1NC ASYFGSIOATXWJA-UHFFFAOYSA-N 0.000 description 1
- CQNKXNIHCKFWMS-UHFFFAOYSA-N Cc(cc1N2)ccc1N=CC2=O Chemical compound Cc(cc1N2)ccc1N=CC2=O CQNKXNIHCKFWMS-UHFFFAOYSA-N 0.000 description 1
- BCJLWYKGUBGKFP-UHFFFAOYSA-N Cc(cn1)cnc1OC Chemical compound Cc(cn1)cnc1OC BCJLWYKGUBGKFP-UHFFFAOYSA-N 0.000 description 1
- UENBBJXGCWILBM-UHFFFAOYSA-N Cc(nc1)ccc1N Chemical compound Cc(nc1)ccc1N UENBBJXGCWILBM-UHFFFAOYSA-N 0.000 description 1
- YAMSVLWOGCBDCA-UHFFFAOYSA-N Cc(nc1)nc2c1[nH]cc2 Chemical compound Cc(nc1)nc2c1[nH]cc2 YAMSVLWOGCBDCA-UHFFFAOYSA-N 0.000 description 1
- WPXHBJUNZGWFJD-UHFFFAOYSA-N Cc(ncnc1)c1O Chemical compound Cc(ncnc1)c1O WPXHBJUNZGWFJD-UHFFFAOYSA-N 0.000 description 1
- XAARYQDTXBRXAA-UHFFFAOYSA-N Cc1c(cc[nH]2)c2cnc1 Chemical compound Cc1c(cc[nH]2)c2cnc1 XAARYQDTXBRXAA-UHFFFAOYSA-N 0.000 description 1
- ZYGYULIGJXJLRW-UHFFFAOYSA-N Cc1c(cn[nH]2)c2ccc1 Chemical compound Cc1c(cn[nH]2)c2ccc1 ZYGYULIGJXJLRW-UHFFFAOYSA-N 0.000 description 1
- CVEAAUAFISZRDR-UHFFFAOYSA-N Cc1c(cn[nH]2)c2ncc1 Chemical compound Cc1c(cn[nH]2)c2ncc1 CVEAAUAFISZRDR-UHFFFAOYSA-N 0.000 description 1
- RLAZPAQEVQDPHR-UHFFFAOYSA-N Cc1c2[nH]ncc2ccc1 Chemical compound Cc1c2[nH]ncc2ccc1 RLAZPAQEVQDPHR-UHFFFAOYSA-N 0.000 description 1
- MPCPRMCFZLOAGZ-UHFFFAOYSA-N Cc1c[nH]c2c1ccnc2 Chemical compound Cc1c[nH]c2c1ccnc2 MPCPRMCFZLOAGZ-UHFFFAOYSA-N 0.000 description 1
- FOQWCSIQBWFFOM-UHFFFAOYSA-N Cc1c[nH]c2c1cncn2 Chemical compound Cc1c[nH]c2c1cncn2 FOQWCSIQBWFFOM-UHFFFAOYSA-N 0.000 description 1
- ZFRKQXVRDFCRJG-UHFFFAOYSA-N Cc1c[nH]c2ccccc12 Chemical compound Cc1c[nH]c2ccccc12 ZFRKQXVRDFCRJG-UHFFFAOYSA-N 0.000 description 1
- RIKMMFOAQPJVMX-UHFFFAOYSA-N Cc1c[nH]nc1 Chemical compound Cc1c[nH]nc1 RIKMMFOAQPJVMX-UHFFFAOYSA-N 0.000 description 1
- KJRRQXYWFQKJIP-UHFFFAOYSA-N Cc1c[o]cc1 Chemical compound Cc1c[o]cc1 KJRRQXYWFQKJIP-UHFFFAOYSA-N 0.000 description 1
- PUMREIFKTMLCAF-UHFFFAOYSA-N Cc1c[o]cn1 Chemical compound Cc1c[o]cn1 PUMREIFKTMLCAF-UHFFFAOYSA-N 0.000 description 1
- VHWFNFITHSPBSR-UHFFFAOYSA-N Cc1c[o]nc1 Chemical compound Cc1c[o]nc1 VHWFNFITHSPBSR-UHFFFAOYSA-N 0.000 description 1
- QENGPZGAWFQWCZ-UHFFFAOYSA-N Cc1c[s]cc1 Chemical compound Cc1c[s]cc1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 1
- DJCJHFFRHKGOCQ-UHFFFAOYSA-N Cc1cc(cc[nH]2)c2nc1 Chemical compound Cc1cc(cc[nH]2)c2nc1 DJCJHFFRHKGOCQ-UHFFFAOYSA-N 0.000 description 1
- VUUJUMZCZFHRFZ-UHFFFAOYSA-N Cc1cc(cn[nH]2)c2nc1 Chemical compound Cc1cc(cn[nH]2)c2nc1 VUUJUMZCZFHRFZ-UHFFFAOYSA-N 0.000 description 1
- RHYYFOFTCIOVEQ-UHFFFAOYSA-N Cc1cc(nccn2)c2nc1 Chemical compound Cc1cc(nccn2)c2nc1 RHYYFOFTCIOVEQ-UHFFFAOYSA-N 0.000 description 1
- JUEXZZNYTAKNBU-UHFFFAOYSA-N Cc1ccc(C=NC(N2)=O)c2c1 Chemical compound Cc1ccc(C=NC(N2)=O)c2c1 JUEXZZNYTAKNBU-UHFFFAOYSA-N 0.000 description 1
- IHVQLIWZGXUWFD-UHFFFAOYSA-N Cc1ccc(CCC(N2)=O)c2c1 Chemical compound Cc1ccc(CCC(N2)=O)c2c1 IHVQLIWZGXUWFD-UHFFFAOYSA-N 0.000 description 1
- DCUNRLLJHAWKRZ-UHFFFAOYSA-N Cc1ccc2[nH]ncc2c1 Chemical compound Cc1ccc2[nH]ncc2c1 DCUNRLLJHAWKRZ-UHFFFAOYSA-N 0.000 description 1
- UAIKQUZQXSTAKX-UHFFFAOYSA-N Cc1cccc(C2)c1NC2=O Chemical compound Cc1cccc(C2)c1NC2=O UAIKQUZQXSTAKX-UHFFFAOYSA-N 0.000 description 1
- HCHIWZADTVYYAR-UHFFFAOYSA-N Cc1cccc(N2)c1NC2=O Chemical compound Cc1cccc(N2)c1NC2=O HCHIWZADTVYYAR-UHFFFAOYSA-N 0.000 description 1
- KGWPHCDTOLQQEP-UHFFFAOYSA-N Cc1cccc2c1[nH]cc2 Chemical compound Cc1cccc2c1[nH]cc2 KGWPHCDTOLQQEP-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N Cc1cccc2c1cc[nH]2 Chemical compound Cc1cccc2c1cc[nH]2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- QCXGJTGMGJOYDP-UHFFFAOYSA-N Cc1cccc2c1nc[nH]2 Chemical compound Cc1cccc2c1nc[nH]2 QCXGJTGMGJOYDP-UHFFFAOYSA-N 0.000 description 1
- CMGDVUCDZOBDNL-UHFFFAOYSA-N Cc1cccc2c1nn[nH]2 Chemical compound Cc1cccc2c1nn[nH]2 CMGDVUCDZOBDNL-UHFFFAOYSA-N 0.000 description 1
- ORLGLBZRQYOWNA-UHFFFAOYSA-N Cc1ccnc(N)c1 Chemical compound Cc1ccnc(N)c1 ORLGLBZRQYOWNA-UHFFFAOYSA-N 0.000 description 1
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N Cc1ccncc1 Chemical compound Cc1ccncc1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 1
- AIKUBOPKWKZULG-UHFFFAOYSA-N Cc1ccnnc1 Chemical compound Cc1ccnnc1 AIKUBOPKWKZULG-UHFFFAOYSA-N 0.000 description 1
- IELZPOFKHRZRGS-UHFFFAOYSA-N Cc1cnc(N)nc1C Chemical compound Cc1cnc(N)nc1C IELZPOFKHRZRGS-UHFFFAOYSA-N 0.000 description 1
- AMWQAIOPVVECAG-UHFFFAOYSA-N Cc1cnc(N)nc1C(F)(F)F Chemical compound Cc1cnc(N)nc1C(F)(F)F AMWQAIOPVVECAG-UHFFFAOYSA-N 0.000 description 1
- YLOYCROMJUCMKB-UHFFFAOYSA-N Cc1cnc(N)nc1OC Chemical compound Cc1cnc(N)nc1OC YLOYCROMJUCMKB-UHFFFAOYSA-N 0.000 description 1
- HDCAHRAHYJJDSU-UHFFFAOYSA-N Cc1cnc(NC)nc1 Chemical compound Cc1cnc(NC)nc1 HDCAHRAHYJJDSU-UHFFFAOYSA-N 0.000 description 1
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N Cc1cnc[nH]1 Chemical compound Cc1cnc[nH]1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 1
- ZYMHCFYHVYGFMS-UHFFFAOYSA-N Cc1cnc[o]1 Chemical compound Cc1cnc[o]1 ZYMHCFYHVYGFMS-UHFFFAOYSA-N 0.000 description 1
- RLYUNPNLXMSXAX-UHFFFAOYSA-N Cc1cnc[s]1 Chemical compound Cc1cnc[s]1 RLYUNPNLXMSXAX-UHFFFAOYSA-N 0.000 description 1
- RHDOEDCLYYJNEZ-UHFFFAOYSA-N Cc1cncc2c1cn[nH]2 Chemical compound Cc1cncc2c1cn[nH]2 RHDOEDCLYYJNEZ-UHFFFAOYSA-N 0.000 description 1
- KOQQEILSRFHKPB-UHFFFAOYSA-N Cc1cncc2c1nc[nH]2 Chemical compound Cc1cncc2c1nc[nH]2 KOQQEILSRFHKPB-UHFFFAOYSA-N 0.000 description 1
- TWGNOYAGHYUFFR-UHFFFAOYSA-N Cc1cncnc1 Chemical compound Cc1cncnc1 TWGNOYAGHYUFFR-UHFFFAOYSA-N 0.000 description 1
- NUOYUBYDFVQGGN-UHFFFAOYSA-N Cc1n[nH]c2c1ccnc2 Chemical compound Cc1n[nH]c2c1ccnc2 NUOYUBYDFVQGGN-UHFFFAOYSA-N 0.000 description 1
- UTHPRTOMISEONZ-UHFFFAOYSA-N Cc1n[nH]c2c1ncnc2 Chemical compound Cc1n[nH]c2c1ncnc2 UTHPRTOMISEONZ-UHFFFAOYSA-N 0.000 description 1
- XKVUYEYANWFIJX-UHFFFAOYSA-N Cc1n[nH]cc1 Chemical compound Cc1n[nH]cc1 XKVUYEYANWFIJX-UHFFFAOYSA-N 0.000 description 1
- PZKFSRWSQOQYNR-UHFFFAOYSA-N Cc1n[nH]cn1 Chemical compound Cc1n[nH]cn1 PZKFSRWSQOQYNR-UHFFFAOYSA-N 0.000 description 1
- XZGLNCKSNVGDNX-UHFFFAOYSA-N Cc1n[nH]nn1 Chemical compound Cc1n[nH]nn1 XZGLNCKSNVGDNX-UHFFFAOYSA-N 0.000 description 1
- CUMCMYMKECWGHO-UHFFFAOYSA-N Cc1n[o]cc1 Chemical compound Cc1n[o]cc1 CUMCMYMKECWGHO-UHFFFAOYSA-N 0.000 description 1
- CEPGJIACGSUAMK-UHFFFAOYSA-N Cc1nc(C)nc(C)c1N Chemical compound Cc1nc(C)nc(C)c1N CEPGJIACGSUAMK-UHFFFAOYSA-N 0.000 description 1
- KXUOIHWSSNTEPE-UHFFFAOYSA-N Cc1nc(O)cnc1 Chemical compound Cc1nc(O)cnc1 KXUOIHWSSNTEPE-UHFFFAOYSA-N 0.000 description 1
- BECYPEHQFUPGLR-UHFFFAOYSA-N Cc1nc(cc[nH]2)c2nc1 Chemical compound Cc1nc(cc[nH]2)c2nc1 BECYPEHQFUPGLR-UHFFFAOYSA-N 0.000 description 1
- LCZUOKDVTBMCMX-UHFFFAOYSA-N Cc1ncc(C)nc1 Chemical compound Cc1ncc(C)nc1 LCZUOKDVTBMCMX-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N Cc1ncc[nH]1 Chemical compound Cc1ncc[nH]1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- VZWOXDYRBDIHMA-UHFFFAOYSA-N Cc1ncc[s]1 Chemical compound Cc1ncc[s]1 VZWOXDYRBDIHMA-UHFFFAOYSA-N 0.000 description 1
- QNBWADFXYBRPBF-UHFFFAOYSA-N Cc1nccc2c1ncnc2 Chemical compound Cc1nccc2c1ncnc2 QNBWADFXYBRPBF-UHFFFAOYSA-N 0.000 description 1
- LNJMHEJAYSYZKK-UHFFFAOYSA-N Cc1ncccn1 Chemical compound Cc1ncccn1 LNJMHEJAYSYZKK-UHFFFAOYSA-N 0.000 description 1
- CAWHJQAVHZEVTJ-UHFFFAOYSA-N Cc1nccnc1 Chemical compound Cc1nccnc1 CAWHJQAVHZEVTJ-UHFFFAOYSA-N 0.000 description 1
- NVCPFJLTUAZDMX-UHFFFAOYSA-N Cc1ncnc(N)c1C=N Chemical compound Cc1ncnc(N)c1C=N NVCPFJLTUAZDMX-UHFFFAOYSA-N 0.000 description 1
- MXDRPNGTQDRKQM-UHFFFAOYSA-N Cc1nnccc1 Chemical compound Cc1nnccc1 MXDRPNGTQDRKQM-UHFFFAOYSA-N 0.000 description 1
- OIVGYFNTFXJUGE-UHFFFAOYSA-N Clc(nc1N2CCOCC2)nc2c1[s]c(I)n2 Chemical compound Clc(nc1N2CCOCC2)nc2c1[s]c(I)n2 OIVGYFNTFXJUGE-UHFFFAOYSA-N 0.000 description 1
- DYYNLRQSLZHCRC-UHFFFAOYSA-N Clc1nc(c(N2CCOCC2)nc(Cl)n2)c2[s]1 Chemical compound Clc1nc(c(N2CCOCC2)nc(Cl)n2)c2[s]1 DYYNLRQSLZHCRC-UHFFFAOYSA-N 0.000 description 1
- MBMSIXRYINXXCZ-UHFFFAOYSA-N Clc1nc(nc(nc2N3CCOCC3)Cl)c2[s]1 Chemical compound Clc1nc(nc(nc2N3CCOCC3)Cl)c2[s]1 MBMSIXRYINXXCZ-UHFFFAOYSA-N 0.000 description 1
- SWEDAZLCYJDAGW-UHFFFAOYSA-N Sc1ccc[s]1 Chemical compound Sc1ccc[s]1 SWEDAZLCYJDAGW-UHFFFAOYSA-N 0.000 description 1
- ISGAWTIDMWIWDF-UHFFFAOYSA-N [I]#CCN1CCOCC1 Chemical compound [I]#CCN1CCOCC1 ISGAWTIDMWIWDF-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010540458A JP2010540458A (ja) | 2010-12-24 |
| JP2010540458A5 true JP2010540458A5 (enExample) | 2011-11-10 |
| JP5736171B2 JP5736171B2 (ja) | 2015-06-17 |
Family
ID=40032435
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010526059A Active JP5736171B2 (ja) | 2007-09-24 | 2008-09-23 | チアゾロピリミジンｐｉ３ｋ阻害剤化合物および使用方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US7893059B2 (enExample) |
| EP (1) | EP2207781B1 (enExample) |
| JP (1) | JP5736171B2 (enExample) |
| CN (1) | CN101932587A (enExample) |
| CA (1) | CA2704711C (enExample) |
| ES (1) | ES2399774T3 (enExample) |
| WO (1) | WO2009042607A1 (enExample) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1577816A3 (en) * | 1996-09-04 | 2006-08-02 | Intertrust Technologies Corp. | Trusted infrastructure support systems, methods and techniques for secure electronic commerce and rights management |
| US20030133939A1 (en) | 2001-01-17 | 2003-07-17 | Genecraft, Inc. | Binding domain-immunoglobulin fusion proteins |
| US7754208B2 (en) | 2001-01-17 | 2010-07-13 | Trubion Pharmaceuticals, Inc. | Binding domain-immunoglobulin fusion proteins |
| PT1912675E (pt) | 2005-07-25 | 2014-05-09 | Emergent Product Dev Seattle | Moléculas de ligaçao especificas para cd37 e especificas para cd20 |
| US8409577B2 (en) | 2006-06-12 | 2013-04-02 | Emergent Product Development Seattle, Llc | Single chain multivalent binding proteins with effector function |
| EP2158207B1 (en) * | 2007-06-12 | 2011-05-25 | F. Hoffmann-La Roche AG | Thiazoliopyrimidines and their use as inhibitors of phosphatidylinositol-3 kinase |
| EP2207781B1 (en) * | 2007-09-24 | 2012-11-28 | Genentech, Inc. | Thiazolopyrimidine p13k inhibitor compounds and methods of use |
| GB0721095D0 (en) * | 2007-10-26 | 2007-12-05 | Piramed Ltd | Pharmaceutical compounds |
| EP2250160B1 (en) | 2008-01-25 | 2015-11-11 | 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 |
| NZ589844A (en) * | 2008-06-19 | 2012-11-30 | Millennium Pharm Inc | Thiophene or thiazole derivatives and their use as phosphatidylinositol 3-kinase (PI3K) inhibitors |
| AU2009276339B2 (en) * | 2008-07-31 | 2012-06-07 | Genentech, Inc. | Pyrimidine compounds, compositions and methods of use |
| TWI378933B (en) | 2008-10-14 | 2012-12-11 | Daiichi Sankyo Co Ltd | Morpholinopurine derivatives |
| US9139589B2 (en) | 2009-01-30 | 2015-09-22 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| 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 |
| JP5647998B2 (ja) * | 2009-03-13 | 2015-01-07 | カトリーケ ユニバーシテイト ルーヴェン、ケー．ユー． ルーヴェン アール アンド ディー | 免疫抑制剤としてのチアゾロピリミジン調節因子 |
| ES2876933T3 (es) | 2009-04-30 | 2021-11-15 | Glaxo Group Ltd | Indazoles sustituidos con oxazol como inhibidores de PI3-cinasas |
| ES2638323T3 (es) * | 2009-05-20 | 2017-10-19 | Glaxosmithkline Llc | Derivados de tiazolopirimidinona como inhibidores de PI3 quinasa |
| WO2010135493A2 (en) * | 2009-05-20 | 2010-11-25 | Emory University | Alzheimer's disease imaging agents |
| 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 |
| SG175708A1 (en) * | 2009-05-27 | 2011-12-29 | Genentech Inc | Bicyclic pyrimidine pi3k inhibitor compounds selective for p110 delta, and methods of use |
| SG176959A1 (en) * | 2009-06-24 | 2012-01-30 | Genentech Inc | Oxo-heterocycle fused pyrimidine compounds, compositions and methods of use |
| CN102711766B (zh) * | 2009-11-12 | 2014-06-04 | 霍夫曼-拉罗奇有限公司 | N-9-取代的嘌呤化合物、组合物和使用方法 |
| US8828990B2 (en) * | 2009-11-12 | 2014-09-09 | Genentech, Inc. | N-7 substituted purine and pyrazolopyrimine 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 |
| ES2986590T3 (es) | 2010-06-14 | 2024-11-12 | Scripps Research Inst | Reprogramación de células hacia un nuevo destino |
| CA2802808A1 (en) | 2010-07-14 | 2012-01-19 | F. Hoffmann-La Roche Ag | Purine compounds selective for pi3k p110 delta, and methods of use |
| US9062038B2 (en) | 2010-08-11 | 2015-06-23 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| US8796268B2 (en) | 2010-08-11 | 2014-08-05 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| WO2012021615A1 (en) | 2010-08-11 | 2012-02-16 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| WO2012035039A1 (en) | 2010-09-15 | 2012-03-22 | F. Hoffmann-La Roche Ag | Azabenzothiazole compounds, compositions and methods of use |
| AU2011316016A1 (en) | 2010-10-13 | 2013-05-30 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| CA2817785A1 (en) | 2010-11-19 | 2012-05-24 | Toby Blench | Pyrazolopyridines and pyrazolopyridines and their use as tyk2 inhibitors |
| AU2011343712B2 (en) | 2010-12-16 | 2015-09-17 | Genentech, Inc. | Tricyclic PI3k inhibitor compounds and methods of use |
| ES2602813T3 (es) * | 2011-06-09 | 2017-02-22 | Rhizen Pharmaceuticals S.A. | Nuevos compuestos como moduladores de GPR-119 |
| 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 |
| WO2014022728A1 (en) | 2012-08-02 | 2014-02-06 | Endo Pharmaceuticals, Inc | Substituted 5 - (quinazolin - 2 - yl) pyrimidin- 2 -amine derivatives useful as pi3k/mtor inhibitors for the treatment of cancer |
| WO2014144850A1 (en) | 2013-03-15 | 2014-09-18 | Genentech, Inc. | Methods of treating cancer and preventing cancer drug resistance |
| CN104557872B (zh) * | 2013-10-16 | 2017-05-24 | 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 |
| US11352426B2 (en) | 2015-09-21 | 2022-06-07 | Aptevo Research And Development Llc | CD3 binding polypeptides |
| 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 |
| 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 |
| WO2019023575A1 (en) * | 2017-07-28 | 2019-01-31 | Chemocentryx, Inc. | IMMUNOMODULATORY 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 |
| AU3262593A (en) | 1992-01-11 | 1993-08-03 | 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 |
| GB9208135D0 (en) | 1992-04-13 | 1992-05-27 | Ludwig Inst Cancer Res | 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 |
| 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 |
| HUP0100287A3 (en) | 1997-11-11 | 2003-04-28 | 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 |
| PL350904A1 (en) * | 1999-03-26 | 2003-02-10 | 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 |
| EP1353693B1 (en) | 2001-01-16 | 2005-03-16 | Glaxo Group Limited | Pharmaceutical combination containing a 4-quinazolineamine and paclitaxel, carboplatin or vinorelbine for the treatment of cancer |
| 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 |
| WO2003037886A2 (en) | 2001-10-30 | 2003-05-08 | 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 |
| AU2003255529B2 (en) | 2002-07-10 | 2008-11-20 | Laboratoires Serono Sa | Use of compounds for increasing spermatozoa motility |
| EA011807B1 (ru) | 2002-07-10 | 2009-06-30 | Лаборатуар Сероно Са | Азолидинонвинильные производные конденсированного бензола |
| 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. |
| AU2004290626A1 (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 |
| KR20070118100A (ko) | 2005-03-04 | 2007-12-13 | 바이엘 파마슈티칼스 코포레이션 | 암 화학요법제로서 유용한 1,3-티아졸-5-카르복사미드 |
| 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 |
| CL2007001165A1 (es) | 2006-04-26 | 2008-01-25 | Hoffmann La Roche | 2-(1h-indazol-4-il)-6-(4-metanosulfonil-piperazin-1-ilmetil)-4-morfolin-4-il-tieno[3,2-d]pirimidina; procedimiento de preparacion; composicion farmaceutica; proceso de preparacion de dicha composicion; kit farmaceutico; y uso para tratar enfermedades tales como cancer, desordenes inmunes y enfermedades cardiovasculares. |
| RU2008141356A (ru) | 2006-04-26 | 2010-06-10 | Ф. Хоффманн-Ля Рош Аг (Ch) | Производные пиримидина в качестве ингибиторов фосфатидилинозитол-3-киназы (pi3k) |
| PL2041139T3 (pl) | 2006-04-26 | 2012-05-31 | Hoffmann La Roche | Związki farmaceutyczne |
| CL2007001166A1 (es) | 2006-04-26 | 2008-01-25 | Piramed Ltd | Compuestos derivados de pirimidina condensada, inhibidores de pi3-quinasa; procesos para preparar los compuestos; composicion farmaceutica que los comprende; uso de los compuestos en la preparacion de medicamentos; proceso para preparar la composicion farmaceutica; y kit que incluye a la composicion farmaceutica |
| BRPI0717907A2 (pt) | 2006-12-07 | 2013-11-05 | Genentech Inc | "composto, composição farmacêutica, métodos para tratar um câncer, para inbir ou modular a atividade da lipídeo quinase, processo para a produçãoo de uma composição farmacêutica, uso de um composto e kit" |
| AR064155A1 (es) | 2006-12-07 | 2009-03-18 | Piramed Ltd | Compuestos de inhibidores de fosfoinositido-3 quinasa y metodos de uso |
| EP2158207B1 (en) * | 2007-06-12 | 2011-05-25 | F. Hoffmann-La Roche AG | Thiazoliopyrimidines and their use as inhibitors of phosphatidylinositol-3 kinase |
| WO2008152394A1 (en) | 2007-06-12 | 2008-12-18 | F.Hoffmann-La Roche Ag | Pharmaceutical compounds |
| WO2008152387A1 (en) | 2007-06-12 | 2008-12-18 | F.Hoffmann-La Roche Ag | Quinazoline derivatives as pi3 kinase inhibitors |
| EP2207781B1 (en) | 2007-09-24 | 2012-11-28 | Genentech, Inc. | Thiazolopyrimidine p13k inhibitor compounds and methods of use |
-
2008
- 2008-09-23 EP EP08832932A patent/EP2207781B1/en active Active
- 2008-09-23 WO PCT/US2008/077394 patent/WO2009042607A1/en not_active Ceased
- 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 ES ES08832932T patent/ES2399774T3/es active Active
- 2008-09-23 CA CA2704711A patent/CA2704711C/en not_active Expired - Fee Related
- 2008-09-23 JP JP2010526059A patent/JP5736171B2/ja active Active
-
2011
- 2011-01-13 US US13/006,217 patent/US8158626B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2010540458A5 (enExample) | ||
| JP7536064B2 (ja) | 抗癌活性及び抗増殖活性を呈する２－アミノピリミジン－６－オン及び類似体 | |
| JP2010512337A5 (enExample) | ||
| JP7262599B2 (ja) | タンパク質キナーゼ阻害活性を有する新規なピリド［３，４－ｄ］ピリミジン－８－オン誘導体およびこれを含む癌の予防、改善または治療用薬学組成物 | |
| JP2009535335A5 (enExample) | ||
| ES3009926T3 (en) | Compounds and compositions for modulating egfr mutant kinase activities | |
| CN108699057B (zh) | 5-取代的2-(吗啉-4-基)-1,7-萘啶 | |
| JP2010512338A5 (enExample) | ||
| ES2399774T3 (es) | Compuestos de tiazolopirimidina inhibidores de PI3K y métodos de uso | |
| RU2009125897A (ru) | Ингибиторы фосфоинозитид-3-киназы и способы их применения | |
| JP6203439B2 (ja) | テトラヒドロピラニルメチル基を有するピリドン誘導体 | |
| RU2008145662A (ru) | Ингибиторы фосфоинозитид-3-киназы и содержащие их фармацевтические композиции | |
| KR20090106508A (ko) | 포스포이노시타이드 3-키나제 억제제 화합물 및 그의 사용 방법 | |
| JP2010539177A5 (enExample) | ||
| JP2012512887A5 (enExample) | ||
| JP2010524914A5 (enExample) | ||
| JP2020503299A5 (enExample) | ||
| JP2011521968A5 (enExample) | ||
| CN106928219B (zh) | 含氮稠杂环化合物、制备方法、中间体、组合物和应用 | |
| BRPI0609047A2 (pt) | composto ou sal farmaceuticamente aceitável do mesmo, formulação farmacêutica, e, uso de um composto | |
| RU2012130929A (ru) | Гетероциклические соединения в качестве ингибиторов янус-киназы | |
| CN103068802B (zh) | 用于治疗增生性异常疾病的化合物 | |
| AU2016333505A1 (en) | New imidazo(4,5-B)pyridine derivatives as dual DYRK1/CLK1 inhibitors | |
| CN111039941B (zh) | 一种含氮杂环化合物、其制备方法及应用 | |
| JP2023538137A (ja) | 芳香環ラクタム系化合物、その製造方法及び使用 |