JP2009535390A5 - - Google Patents
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- Publication number
- JP2009535390A5 JP2009535390A5 JP2009508465A JP2009508465A JP2009535390A5 JP 2009535390 A5 JP2009535390 A5 JP 2009535390A5 JP 2009508465 A JP2009508465 A JP 2009508465A JP 2009508465 A JP2009508465 A JP 2009508465A JP 2009535390 A5 JP2009535390 A5 JP 2009535390A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- thieno
- pyrimidin
- group
- substituted
- 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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- 150000001875 compounds Chemical class 0.000 claims 15
- 125000001072 heteroaryl group Chemical group 0.000 claims 9
- 206010028980 Neoplasm Diseases 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 201000011510 cancer Diseases 0.000 claims 7
- 239000003795 chemical substances by application Substances 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 229920006395 saturated elastomer Polymers 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000002619 bicyclic group Chemical group 0.000 claims 4
- 125000002950 monocyclic group Chemical group 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 210000000481 breast Anatomy 0.000 claims 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
- 210000001072 colon Anatomy 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 210000004072 lung Anatomy 0.000 claims 3
- 210000001672 ovary Anatomy 0.000 claims 3
- 125000006239 protecting group Chemical group 0.000 claims 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 claims 2
- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 230000002159 abnormal effect Effects 0.000 claims 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 2
- 230000006399 behavior Effects 0.000 claims 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims 2
- 229940092714 benzenesulfonic acid Drugs 0.000 claims 2
- 229910052796 boron Inorganic materials 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 230000003915 cell function Effects 0.000 claims 2
- 230000010261 cell growth Effects 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 208000005017 glioblastoma Diseases 0.000 claims 2
- 210000003128 head Anatomy 0.000 claims 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
- 208000032839 leukemia Diseases 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 201000001441 melanoma Diseases 0.000 claims 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- 210000000214 mouth Anatomy 0.000 claims 2
- 210000003739 neck Anatomy 0.000 claims 2
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 2
- 210000003800 pharynx Anatomy 0.000 claims 2
- 210000002307 prostate Anatomy 0.000 claims 2
- 229930192474 thiophene Natural products 0.000 claims 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims 1
- QBUATVYLHWFGMJ-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-4-pyridin-4-ylthieno[3,2-d]pyrimidine Chemical compound C=12SC=CC2=NC(C=2C=3C=NNC=3C=CC=2)=NC=1C1=CC=NC=C1 QBUATVYLHWFGMJ-UHFFFAOYSA-N 0.000 claims 1
- YFYAZARDHCTCLP-UHFFFAOYSA-N 2-(1h-indol-4-yl)-4-pyridin-4-ylthieno[3,2-d]pyrimidine Chemical compound C1=CC=C2NC=CC2=C1C(N=C1C=CSC1=1)=NC=1C1=CC=NC=C1 YFYAZARDHCTCLP-UHFFFAOYSA-N 0.000 claims 1
- -1 2-amino-thiazol-5-yl Chemical group 0.000 claims 1
- GJWHKDGHZGMARA-UHFFFAOYSA-N 3-(4-imidazol-1-ylthieno[3,2-d]pyrimidin-2-yl)phenol Chemical compound OC1=CC=CC(C=2N=C3C=CSC3=C(N3C=NC=C3)N=2)=C1 GJWHKDGHZGMARA-UHFFFAOYSA-N 0.000 claims 1
- WHVNKILIPFXBOY-UHFFFAOYSA-N 3-(4-pyridin-3-ylthieno[3,2-d]pyrimidin-2-yl)phenol Chemical compound OC1=CC=CC(C=2N=C3C=CSC3=C(C=3C=NC=CC=3)N=2)=C1 WHVNKILIPFXBOY-UHFFFAOYSA-N 0.000 claims 1
- FFIBWRLRUXWTEA-UHFFFAOYSA-N 3-(4-pyridin-4-ylthieno[3,2-d]pyrimidin-2-yl)phenol Chemical compound OC1=CC=CC(C=2N=C3C=CSC3=C(C=3C=CN=CC=3)N=2)=C1 FFIBWRLRUXWTEA-UHFFFAOYSA-N 0.000 claims 1
- HWCWGIPSZQGRNZ-UHFFFAOYSA-N 3-(4-pyrimidin-5-ylthieno[3,2-d]pyrimidin-2-yl)phenol Chemical compound OC1=CC=CC(C=2N=C3C=CSC3=C(C=3C=NC=NC=3)N=2)=C1 HWCWGIPSZQGRNZ-UHFFFAOYSA-N 0.000 claims 1
- SVYNXINGYSYINW-UHFFFAOYSA-N 3-[4-(1,3-thiazol-5-yl)thieno[3,2-d]pyrimidin-2-yl]phenol Chemical compound OC1=CC=CC(C=2N=C3C=CSC3=C(C=3SC=NC=3)N=2)=C1 SVYNXINGYSYINW-UHFFFAOYSA-N 0.000 claims 1
- FLEWGOXMYNINSP-UHFFFAOYSA-N 3-[4-(1h-pyrazol-4-yl)thieno[3,2-d]pyrimidin-2-yl]phenol Chemical compound OC1=CC=CC(C=2N=C3C=CSC3=C(C3=CNN=C3)N=2)=C1 FLEWGOXMYNINSP-UHFFFAOYSA-N 0.000 claims 1
- UKQJZKSEWHJSFE-UHFFFAOYSA-N 3-[4-(2-aminopyridin-4-yl)thieno[3,2-d]pyrimidin-2-yl]phenol Chemical compound C1=NC(N)=CC(C=2C=3SC=CC=3N=C(N=2)C=2C=C(O)C=CC=2)=C1 UKQJZKSEWHJSFE-UHFFFAOYSA-N 0.000 claims 1
- AWYCULSCTAEGSR-UHFFFAOYSA-N 3-[4-(2-chloropyridin-4-yl)thieno[3,2-d]pyrimidin-2-yl]phenol Chemical compound OC1=CC=CC(C=2N=C3C=CSC3=C(C=3C=C(Cl)N=CC=3)N=2)=C1 AWYCULSCTAEGSR-UHFFFAOYSA-N 0.000 claims 1
- TZWIKGNHELHVNU-UHFFFAOYSA-N 3-[4-(2-fluoropyridin-4-yl)thieno[3,2-d]pyrimidin-2-yl]phenol Chemical compound OC1=CC=CC(C=2N=C3C=CSC3=C(C=3C=C(F)N=CC=3)N=2)=C1 TZWIKGNHELHVNU-UHFFFAOYSA-N 0.000 claims 1
- VYMJBVGKMZUUBO-UHFFFAOYSA-N 3-[4-(3-chloropyridin-4-yl)thieno[3,2-d]pyrimidin-2-yl]phenol Chemical compound OC1=CC=CC(C=2N=C3C=CSC3=C(C=3C(=CN=CC=3)Cl)N=2)=C1 VYMJBVGKMZUUBO-UHFFFAOYSA-N 0.000 claims 1
- WXLWYQKQQFVUCC-UHFFFAOYSA-N 3-[4-(6-aminopyridin-3-yl)thieno[3,2-d]pyrimidin-2-yl]phenol Chemical compound C1=NC(N)=CC=C1C1=NC(C=2C=C(O)C=CC=2)=NC2=C1SC=C2 WXLWYQKQQFVUCC-UHFFFAOYSA-N 0.000 claims 1
- CGHQUFGFBQJYDV-UHFFFAOYSA-N 3-[4-[2-(dimethylamino)pyridin-4-yl]thieno[3,2-d]pyrimidin-2-yl]phenol Chemical compound C1=NC(N(C)C)=CC(C=2C=3SC=CC=3N=C(N=2)C=2C=C(O)C=CC=2)=C1 CGHQUFGFBQJYDV-UHFFFAOYSA-N 0.000 claims 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- CWYBUJADCIAFKI-UHFFFAOYSA-N 4-[2-(3-hydroxyphenyl)thieno[3,2-d]pyrimidin-4-yl]-1h-pyridin-2-one Chemical compound OC1=CC=CC(C=2N=C3C=CSC3=C(C3=CC(=O)NC=C3)N=2)=C1 CWYBUJADCIAFKI-UHFFFAOYSA-N 0.000 claims 1
- XDTWBJBBFYBFHL-UHFFFAOYSA-N 4-[2-(3-hydroxyphenyl)thieno[3,2-d]pyrimidin-4-yl]pyridine-2-carbonitrile Chemical compound OC1=CC=CC(C=2N=C3C=CSC3=C(C=3C=C(N=CC=3)C#N)N=2)=C1 XDTWBJBBFYBFHL-UHFFFAOYSA-N 0.000 claims 1
- GNWMRHKXTOBUPW-UHFFFAOYSA-N 4-[2-(3-hydroxyphenyl)thieno[3,2-d]pyrimidin-4-yl]pyridine-2-carboxamide Chemical compound C1=NC(C(=O)N)=CC(C=2C=3SC=CC=3N=C(N=2)C=2C=C(O)C=CC=2)=C1 GNWMRHKXTOBUPW-UHFFFAOYSA-N 0.000 claims 1
- BJGBPJWXEYEQMU-UHFFFAOYSA-N 5-[2-(3-hydroxyphenyl)thieno[3,2-d]pyrimidin-4-yl]-1h-pyridin-2-one Chemical compound OC1=CC=CC(C=2N=C3C=CSC3=C(C=3C=NC(O)=CC=3)N=2)=C1 BJGBPJWXEYEQMU-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
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- 208000017701 Endocrine disease Diseases 0.000 claims 1
- 208000004463 Follicular Adenocarcinoma Diseases 0.000 claims 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 1
- 208000017604 Hodgkin disease Diseases 0.000 claims 1
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 206010023347 Keratoacanthoma Diseases 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 1
- 208000018501 Lymphatic disease Diseases 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 206010029260 Neuroblastoma Diseases 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
- 102000038030 PI3Ks Human genes 0.000 claims 1
- 108091007960 PI3Ks Proteins 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
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 1
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 1
- 208000036142 Viral infection Diseases 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 208000009956 adenocarcinoma Diseases 0.000 claims 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims 1
- 235000003704 aspartic acid Nutrition 0.000 claims 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 1
- 210000003445 biliary tract Anatomy 0.000 claims 1
- 210000000988 bone and bone Anatomy 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 210000000133 brain stem Anatomy 0.000 claims 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 1
- 210000004027 cell Anatomy 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 claims 1
- 210000003679 cervix uteri Anatomy 0.000 claims 1
- 235000015165 citric acid Nutrition 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000030172 endocrine system disease Diseases 0.000 claims 1
- 210000004696 endometrium Anatomy 0.000 claims 1
- 210000003238 esophagus Anatomy 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 239000001530 fumaric acid Substances 0.000 claims 1
- 210000001035 gastrointestinal tract Anatomy 0.000 claims 1
- 235000013922 glutamic acid Nutrition 0.000 claims 1
- 239000004220 glutamic acid Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 210000003494 hepatocyte Anatomy 0.000 claims 1
- 229960000443 hydrochloric acid Drugs 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- 229940071870 hydroiodic acid Drugs 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 208000026278 immune system disease Diseases 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 239000004310 lactic acid Substances 0.000 claims 1
- 235000014655 lactic acid Nutrition 0.000 claims 1
- 208000003849 large cell carcinoma Diseases 0.000 claims 1
- 210000000867 larynx Anatomy 0.000 claims 1
- 210000000088 lip Anatomy 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
- 208000018555 lymphatic system disease Diseases 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- 239000001630 malic acid Substances 0.000 claims 1
- 235000011090 malic acid Nutrition 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 208000030159 metabolic disease Diseases 0.000 claims 1
- 230000002503 metabolic effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 229910017604 nitric acid Inorganic materials 0.000 claims 1
- 235000006408 oxalic acid Nutrition 0.000 claims 1
- 210000000496 pancreas Anatomy 0.000 claims 1
- 229960004838 phosphoric acid Drugs 0.000 claims 1
- 230000000069 prophylactic effect Effects 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
- 150000003230 pyrimidines Chemical class 0.000 claims 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
- 210000000664 rectum Anatomy 0.000 claims 1
- 208000000649 small cell carcinoma Diseases 0.000 claims 1
- 210000000813 small intestine Anatomy 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 206010041823 squamous cell carcinoma Diseases 0.000 claims 1
- 210000002784 stomach Anatomy 0.000 claims 1
- 229940032330 sulfuric acid Drugs 0.000 claims 1
- 239000011975 tartaric acid Substances 0.000 claims 1
- 235000002906 tartaric acid Nutrition 0.000 claims 1
- 210000001550 testis Anatomy 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 201000002510 thyroid cancer Diseases 0.000 claims 1
- 210000001685 thyroid gland Anatomy 0.000 claims 1
- 208000030901 thyroid gland follicular carcinoma Diseases 0.000 claims 1
- 210000002105 tongue Anatomy 0.000 claims 1
- 201000005112 urinary bladder cancer Diseases 0.000 claims 1
- 230000009385 viral infection Effects 0.000 claims 1
- 0 *c1nc(Cl)nc2c1CCCCC2 Chemical compound *c1nc(Cl)nc2c1CCCCC2 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0608820.7A GB0608820D0 (en) | 2006-05-04 | 2006-05-04 | Pharmaceutical compounds |
| GB0608820.7 | 2006-05-04 | ||
| PCT/GB2007/001644 WO2007132171A1 (en) | 2006-05-04 | 2007-05-04 | Pharmaceutical compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009535390A JP2009535390A (ja) | 2009-10-01 |
| JP2009535390A5 true JP2009535390A5 (enExample) | 2010-06-24 |
| JP5329395B2 JP5329395B2 (ja) | 2013-10-30 |
Family
ID=36603916
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009508465A Expired - Fee Related JP5329395B2 (ja) | 2006-05-04 | 2007-05-04 | 医薬化合物 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8153639B2 (enExample) |
| EP (1) | EP2035431B1 (enExample) |
| JP (1) | JP5329395B2 (enExample) |
| CN (1) | CN101479276B (enExample) |
| CA (1) | CA2651136C (enExample) |
| ES (1) | ES2562935T3 (enExample) |
| GB (1) | GB0608820D0 (enExample) |
| WO (1) | WO2007132171A1 (enExample) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR064155A1 (es) | 2006-12-07 | 2009-03-18 | Piramed Ltd | Compuestos de inhibidores de fosfoinositido-3 quinasa y metodos de uso |
| WO2008073785A2 (en) | 2006-12-07 | 2008-06-19 | Genentech, Inc. | Phosphoinositide 3-kinase inhibitor compounds and methods of use |
| EP2173722B1 (en) * | 2007-07-26 | 2012-08-29 | Novartis AG | Pyrimidine derivatives useful for the treatment of inflammatory or allergic conditions |
| TWI471134B (zh) | 2007-09-12 | 2015-02-01 | Genentech Inc | 肌醇磷脂３－激酶抑制劑化合物及化療劑之組合及使用方法 |
| CA2701292C (en) * | 2007-10-25 | 2015-03-24 | Genentech, Inc. | Process for making thienopyrimidine compounds |
| GB0721095D0 (en) * | 2007-10-26 | 2007-12-05 | Piramed Ltd | Pharmaceutical compounds |
| CA2710194C (en) | 2007-12-19 | 2014-04-22 | Amgen Inc. | Inhibitors of p13 kinase |
| US8415376B2 (en) | 2008-05-30 | 2013-04-09 | Amgen Inc. | Inhibitors of PI3 kinase |
| US8163743B2 (en) * | 2008-06-05 | 2012-04-24 | GlaxoGroupLimited | 4-carboxamide indazole derivatives useful as inhibitors of PI3-kinases |
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| JP5656880B2 (ja) | 2009-03-09 | 2015-01-21 | グラクソ グループ リミテッドＧｌａｘｏ Ｇｒｏｕｐ Ｌｉｍｉｔｅｄ | Ｐｉ３キナーゼの阻害剤としての４−オキサジアゾール−２−イル−インダゾール |
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| BR112012011147A2 (pt) | 2009-11-12 | 2021-09-08 | F.Hoffmann-La Roche Ag | Composto, composição farmacêutica e uso de um composto. |
| GB201018124D0 (en) | 2010-10-27 | 2010-12-08 | Glaxo Group Ltd | Polymorphs and salts |
| EP3053925A1 (en) | 2010-12-16 | 2016-08-10 | F. Hoffmann-La Roche AG | Tricyclic pi3k inhibitor compounds and methods of use |
| WO2013152717A1 (zh) * | 2012-04-10 | 2013-10-17 | 上海昀怡健康管理咨询有限公司 | 稠合嘧啶类化合物，其制备方法，中间体，组合物和应用 |
| KR20160027218A (ko) | 2012-05-23 | 2016-03-09 | 에프. 호프만-라 로슈 아게 | 내배엽 및 간세포를 수득하고 사용하는 조성물 및 방법 |
| US9745321B2 (en) | 2013-09-30 | 2017-08-29 | Shanghai Yingli Pharmaceutical Co., Ltd | Fused pyrimidine compound, intermediate, preparation method therefor, and composition and application thereof |
| AU2016378723B2 (en) | 2015-12-22 | 2021-09-30 | SHY Therapeutics LLC | Compounds for the treatment of cancer and inflammatory disease |
| MA49458A (fr) | 2017-06-21 | 2020-04-29 | SHY Therapeutics LLC | Composés interagissant avec la superfamille ras destinés à être utilisés dans le traitement de cancers, de maladies inflammatoires, de rasopathies et de maladies fibrotiques |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6187777B1 (en) * | 1998-02-06 | 2001-02-13 | Amgen Inc. | Compounds and methods which modulate feeding behavior and related diseases |
| JP3810017B2 (ja) * | 2000-04-27 | 2006-08-16 | アステラス製薬株式会社 | 縮合ヘテロアリール誘導体 |
| CN1186324C (zh) | 2000-04-27 | 2005-01-26 | 山之内制药株式会社 | 稠合杂芳基衍生物 |
| ES2217956B1 (es) * | 2003-01-23 | 2006-04-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de 4-aminotieno(2,3-d)pirimidin-6-carbonitrilo. |
| AR045445A1 (es) * | 2003-08-05 | 2005-10-26 | Vertex Pharma | Compuestos ihinibidores de canales ionicos regulados por voltaje |
| GB0423653D0 (en) * | 2004-10-25 | 2004-11-24 | Piramed Ltd | Pharmaceutical compounds |
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- 2007-05-04 JP JP2009508465A patent/JP5329395B2/ja not_active Expired - Fee Related
- 2007-05-04 CN CN2007800245030A patent/CN101479276B/zh active Active
- 2007-05-04 ES ES07732675.9T patent/ES2562935T3/es active Active
- 2007-05-04 US US12/299,600 patent/US8153639B2/en active Active
- 2007-05-04 WO PCT/GB2007/001644 patent/WO2007132171A1/en not_active Ceased
- 2007-05-04 EP EP07732675.9A patent/EP2035431B1/en active Active
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