HRP20100446T1 - Derivat tieno[3,2-d]pirimidina koristan kao inhibitor pi3k - Google Patents
Derivat tieno[3,2-d]pirimidina koristan kao inhibitor pi3k Download PDFInfo
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- HRP20100446T1 HRP20100446T1 HR20100446T HRP20100446T HRP20100446T1 HR P20100446 T1 HRP20100446 T1 HR P20100446T1 HR 20100446 T HR20100446 T HR 20100446T HR P20100446 T HRP20100446 T HR P20100446T HR P20100446 T1 HRP20100446 T1 HR P20100446T1
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- Prior art keywords
- acid
- compound
- cancer
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- RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical class C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 title claims abstract 3
- 239000012828 PI3K inhibitor Substances 0.000 title 1
- 229940043441 phosphoinositide 3-kinase inhibitor Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 23
- 150000003839 salts Chemical class 0.000 claims abstract 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 9
- 206010028980 Neoplasm Diseases 0.000 claims 8
- 208000035475 disorder Diseases 0.000 claims 6
- 201000011510 cancer Diseases 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
- 238000000034 method Methods 0.000 claims 4
- 239000000825 pharmaceutical preparation Substances 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
- 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
- 201000010099 disease Diseases 0.000 claims 3
- 206010009944 Colon cancer Diseases 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
- 206010029260 Neuroblastoma Diseases 0.000 claims 2
- 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 claims 2
- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 claims 2
- 208000024770 Thyroid neoplasm Diseases 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 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
- 230000003915 cell function Effects 0.000 claims 2
- 230000010261 cell growth Effects 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 208000005017 glioblastoma Diseases 0.000 claims 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
- 210000004185 liver Anatomy 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
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 2
- 210000003800 pharynx Anatomy 0.000 claims 2
- 229960004838 phosphoric acid Drugs 0.000 claims 2
- 210000002307 prostate Anatomy 0.000 claims 2
- 229940032330 sulfuric acid Drugs 0.000 claims 2
- 230000001225 therapeutic effect Effects 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
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-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
- RFRIKACSFOTIMU-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine;methanesulfonic acid Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 RFRIKACSFOTIMU-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
- 206010004593 Bile duct cancer Diseases 0.000 claims 1
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
- 201000009030 Carcinoma Diseases 0.000 claims 1
- 208000010667 Carcinoma of liver and intrahepatic biliary tract Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 208000001333 Colorectal Neoplasms 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
- 206010014759 Endometrial neoplasm Diseases 0.000 claims 1
- 206010061968 Gastric neoplasm 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
- 206010073069 Hepatic cancer 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
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 208000025966 Neurological disease Diseases 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 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
- 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
- 208000033781 Thyroid carcinoma Diseases 0.000 claims 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 1
- 208000036142 Viral infection Diseases 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 229960000583 acetic acid Drugs 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 239000013543 active substance 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
- 150000001412 amines Chemical class 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
- 201000007180 bile duct carcinoma Diseases 0.000 claims 1
- 201000001531 bladder carcinoma Diseases 0.000 claims 1
- 201000004571 bone carcinoma Diseases 0.000 claims 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims 1
- 239000004327 boric acid Substances 0.000 claims 1
- 229910052796 boron Inorganic materials 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 201000000220 brain stem cancer Diseases 0.000 claims 1
- 210000000481 breast 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
- 239000003054 catalyst Substances 0.000 claims 1
- 201000007455 central nervous system cancer Diseases 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 235000015165 citric acid Nutrition 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 230000007368 endocrine function Effects 0.000 claims 1
- 210000004696 endometrium Anatomy 0.000 claims 1
- 210000003238 esophagus Anatomy 0.000 claims 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims 1
- 208000021045 exocrine pancreatic carcinoma Diseases 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 229940013688 formic acid Drugs 0.000 claims 1
- 239000001530 fumaric acid Substances 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 235000013922 glutamic acid Nutrition 0.000 claims 1
- 239000004220 glutamic acid Substances 0.000 claims 1
- 210000003128 head Anatomy 0.000 claims 1
- 206010073071 hepatocellular carcinoma Diseases 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
- 208000026278 immune system disease Diseases 0.000 claims 1
- 230000004054 inflammatory process Effects 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
- 210000000867 larynx Anatomy 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 210000000088 lip Anatomy 0.000 claims 1
- 201000002250 liver carcinoma Diseases 0.000 claims 1
- 208000014018 liver neoplasm Diseases 0.000 claims 1
- 210000004072 lung Anatomy 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
- 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
- 230000007102 metabolic function Effects 0.000 claims 1
- 210000003739 neck Anatomy 0.000 claims 1
- 229940074355 nitric acid Drugs 0.000 claims 1
- 229910017604 nitric acid Inorganic materials 0.000 claims 1
- 210000001672 ovary Anatomy 0.000 claims 1
- 235000006408 oxalic acid Nutrition 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 201000010198 papillary carcinoma Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000000069 prophylactic effect Effects 0.000 claims 1
- 235000019260 propionic acid Nutrition 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
- 206010038038 rectal cancer Diseases 0.000 claims 1
- 201000001275 rectum cancer Diseases 0.000 claims 1
- 201000000849 skin cancer Diseases 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
- 210000002784 stomach Anatomy 0.000 claims 1
- 201000011549 stomach cancer Diseases 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
- 201000002510 thyroid cancer Diseases 0.000 claims 1
- 208000013077 thyroid gland carcinoma Diseases 0.000 claims 1
- 208000030901 thyroid gland follicular carcinoma Diseases 0.000 claims 1
- 210000002105 tongue Anatomy 0.000 claims 1
- 208000010576 undifferentiated carcinoma Diseases 0.000 claims 1
- 208000010570 urinary bladder carcinoma Diseases 0.000 claims 1
- 230000009385 viral infection Effects 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5355—Non-condensed oxazines and containing further heterocyclic rings
-
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
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PCT/IB2007/001058 WO2007129161A2 (en) | 2006-04-26 | 2007-04-24 | Thieno [3, 2-d] pyrimidine derivative useful as pi3k inhibitor |
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