JP2009538825A5 - - Google Patents
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- Publication number
- JP2009538825A5 JP2009538825A5 JP2009507751A JP2009507751A JP2009538825A5 JP 2009538825 A5 JP2009538825 A5 JP 2009538825A5 JP 2009507751 A JP2009507751 A JP 2009507751A JP 2009507751 A JP2009507751 A JP 2009507751A JP 2009538825 A5 JP2009538825 A5 JP 2009538825A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- morpholinothieno
- indazol
- pyrimidin
- pyrimidine
- 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
- 150000001875 compounds Chemical class 0.000 claims description 35
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052796 boron Inorganic materials 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 230000001404 mediated effect Effects 0.000 claims description 2
- -1 indazol-4-yl Chemical group 0.000 claims 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 19
- 125000001072 heteroaryl group Chemical group 0.000 claims 17
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 15
- 239000008194 pharmaceutical composition Substances 0.000 claims 15
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 14
- 229910052760 oxygen Inorganic materials 0.000 claims 13
- 229910052717 sulfur Inorganic materials 0.000 claims 13
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 11
- 206010028980 Neoplasm Diseases 0.000 claims 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 10
- 201000011510 cancer Diseases 0.000 claims 9
- 125000005842 heteroatom Chemical group 0.000 claims 9
- 125000000623 heterocyclic group Chemical group 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 125000004432 carbon atom Chemical group C* 0.000 claims 7
- ZZAKLGGGMWORRT-UHFFFAOYSA-N 1-methylsulfonylpiperazine Chemical compound CS(=O)(=O)N1CCNCC1 ZZAKLGGGMWORRT-UHFFFAOYSA-N 0.000 claims 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 5
- 210000000481 breast Anatomy 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 5
- 208000035475 disorder Diseases 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 210000004072 lung Anatomy 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- 210000001672 ovary Anatomy 0.000 claims 5
- 229920006395 saturated elastomer Polymers 0.000 claims 5
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- FIRWUSRFSSPHFG-UHFFFAOYSA-N 2-sulfonylpyran Chemical compound O=S(=O)=C1C=CC=CO1 FIRWUSRFSSPHFG-UHFFFAOYSA-N 0.000 claims 4
- 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
- 230000002159 abnormal effect Effects 0.000 claims 4
- 125000002619 bicyclic group Chemical group 0.000 claims 4
- 230000003915 cell function Effects 0.000 claims 4
- 230000010261 cell growth Effects 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 208000005017 glioblastoma Diseases 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 201000001441 melanoma Diseases 0.000 claims 4
- 125000002950 monocyclic group Chemical group 0.000 claims 4
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 4
- 210000003800 pharynx Anatomy 0.000 claims 4
- 210000002307 prostate Anatomy 0.000 claims 4
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims 3
- 208000017701 Endocrine disease Diseases 0.000 claims 3
- 206010061218 Inflammation Diseases 0.000 claims 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 3
- 208000012902 Nervous system disease Diseases 0.000 claims 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 3
- 208000036142 Viral infection Diseases 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 230000006399 behavior Effects 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
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 210000003128 head Anatomy 0.000 claims 3
- 208000026278 immune system disease Diseases 0.000 claims 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 3
- 230000004054 inflammatory process Effects 0.000 claims 3
- 210000004185 liver Anatomy 0.000 claims 3
- 208000030159 metabolic disease Diseases 0.000 claims 3
- 230000002503 metabolic effect Effects 0.000 claims 3
- 210000003739 neck Anatomy 0.000 claims 3
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 3
- 210000002784 stomach Anatomy 0.000 claims 3
- 230000009385 viral infection Effects 0.000 claims 3
- MVXVYAKCVDQRLW-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 claims 2
- DDXWWYSOOMVLCP-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-[(4-methylsulfonyl-1,4-diazepan-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCCN1CC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 DDXWWYSOOMVLCP-UHFFFAOYSA-N 0.000 claims 2
- FNLOVLWENLVWRZ-UHFFFAOYSA-N 4-[2-(1h-indazol-5-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=C4C=NNC4=CC=3)=NC(N3CCOCC3)=C2S1 FNLOVLWENLVWRZ-UHFFFAOYSA-N 0.000 claims 2
- VHGZNSYUSIUJHB-UHFFFAOYSA-N 4-[2-(2-methyl-3h-benzimidazol-5-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C=1C=C2NC(C)=NC2=CC=1C(N=C1C=C(CN2CCN(CC2)S(C)(=O)=O)SC1=1)=NC=1N1CCOCC1 VHGZNSYUSIUJHB-UHFFFAOYSA-N 0.000 claims 2
- 208000010507 Adenocarcinoma of Lung Diseases 0.000 claims 2
- 208000003200 Adenoma Diseases 0.000 claims 2
- 206010001233 Adenoma benign Diseases 0.000 claims 2
- 206010005003 Bladder cancer Diseases 0.000 claims 2
- 201000009030 Carcinoma 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
- 208000017604 Hodgkin disease Diseases 0.000 claims 2
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims 2
- 208000018501 Lymphatic disease Diseases 0.000 claims 2
- 206010029260 Neuroblastoma Diseases 0.000 claims 2
- 208000025966 Neurological disease Diseases 0.000 claims 2
- 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 claims 2
- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 claims 2
- 206010038389 Renal cancer Diseases 0.000 claims 2
- 208000006265 Renal cell carcinoma Diseases 0.000 claims 2
- 206010039491 Sarcoma Diseases 0.000 claims 2
- 201000010208 Seminoma Diseases 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
- 208000009956 adenocarcinoma Diseases 0.000 claims 2
- 229910000147 aluminium phosphate Inorganic materials 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
- 210000000013 bile duct Anatomy 0.000 claims 2
- 201000001531 bladder carcinoma Diseases 0.000 claims 2
- 210000000988 bone and bone Anatomy 0.000 claims 2
- 208000015322 bone marrow disease Diseases 0.000 claims 2
- 210000000133 brain stem Anatomy 0.000 claims 2
- 210000004027 cell Anatomy 0.000 claims 2
- 210000003169 central nervous system Anatomy 0.000 claims 2
- 210000003679 cervix uteri Anatomy 0.000 claims 2
- 230000001886 ciliary effect Effects 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 210000004696 endometrium Anatomy 0.000 claims 2
- 210000003238 esophagus Anatomy 0.000 claims 2
- 210000003494 hepatocyte Anatomy 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
- 208000003849 large cell carcinoma Diseases 0.000 claims 2
- 210000002429 large intestine Anatomy 0.000 claims 2
- 210000000867 larynx Anatomy 0.000 claims 2
- 208000032839 leukemia Diseases 0.000 claims 2
- 210000000088 lip Anatomy 0.000 claims 2
- 201000005249 lung adenocarcinoma Diseases 0.000 claims 2
- 208000018555 lymphatic system disease 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
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 210000000214 mouth Anatomy 0.000 claims 2
- AEBOUKYQGJMTNV-UHFFFAOYSA-N n-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-n,1-dimethylpiperidin-4-amine Chemical compound C1CN(C)CCC1N(C)CC(SC1=2)=CC1=NC(C=1C=3C=NNC=3C=CC=1)=NC=2N1CCOCC1 AEBOUKYQGJMTNV-UHFFFAOYSA-N 0.000 claims 2
- 210000000496 pancreas Anatomy 0.000 claims 2
- 201000010198 papillary carcinoma Diseases 0.000 claims 2
- RFIOZSIHFNEKFF-UHFFFAOYSA-M piperazine-1-carboxylate Chemical compound [O-]C(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-M 0.000 claims 2
- 210000000664 rectum Anatomy 0.000 claims 2
- 201000010174 renal carcinoma Diseases 0.000 claims 2
- 208000000649 small cell carcinoma Diseases 0.000 claims 2
- 210000000813 small intestine Anatomy 0.000 claims 2
- 206010041823 squamous cell carcinoma Diseases 0.000 claims 2
- 210000001550 testis Anatomy 0.000 claims 2
- 201000002510 thyroid cancer Diseases 0.000 claims 2
- 210000001685 thyroid gland Anatomy 0.000 claims 2
- 208000030901 thyroid gland follicular carcinoma Diseases 0.000 claims 2
- 210000002105 tongue Anatomy 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
- 208000010576 undifferentiated carcinoma Diseases 0.000 claims 2
- 208000010570 urinary bladder carcinoma Diseases 0.000 claims 2
- KPAAQIZTBZUBSP-UHFFFAOYSA-N (1-aminocyclopropyl)-[4-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]methyl]piperazin-1-yl]methanone Chemical compound C1CN(CC=2SC3=NC(=NC(=C3C=2)N2CCOCC2)C=2C=3C=NNC=3C=CC=2)CCN1C(=O)C1(N)CC1 KPAAQIZTBZUBSP-UHFFFAOYSA-N 0.000 claims 1
- LFCVCLBMWOUBFK-UHFFFAOYSA-N (1-aminocyclopropyl)-[4-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]methanone Chemical compound C1CN(CC=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=3C=NNC=3C=CC=2)CCN1C(=O)C1(N)CC1 LFCVCLBMWOUBFK-UHFFFAOYSA-N 0.000 claims 1
- ZICBYUSXNWXXIS-MRXNPFEDSA-N (2r)-2-amino-1-[4-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1CN(C(=O)[C@H](N)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=4C=NNC=4C=CC=3)N=C2S1 ZICBYUSXNWXXIS-MRXNPFEDSA-N 0.000 claims 1
- QKIVFQZUZVLIAM-MRXNPFEDSA-N (2r)-2-amino-1-[4-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1CN(C(=O)[C@H](N)C)CCN1CC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 QKIVFQZUZVLIAM-MRXNPFEDSA-N 0.000 claims 1
- CDXCQZQWDIQYSC-MRXNPFEDSA-N (2r)-2-hydroxy-1-[4-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1CN(C(=O)[C@H](O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=4C=NNC=4C=CC=3)N=C2S1 CDXCQZQWDIQYSC-MRXNPFEDSA-N 0.000 claims 1
- JPFJDPRZHNLDPU-MRXNPFEDSA-N (2r)-2-hydroxy-1-[4-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1CN(C(=O)[C@H](O)C)CCN1CC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 JPFJDPRZHNLDPU-MRXNPFEDSA-N 0.000 claims 1
- ZICBYUSXNWXXIS-INIZCTEOSA-N (2s)-2-amino-1-[4-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1CN(C(=O)[C@@H](N)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=4C=NNC=4C=CC=3)N=C2S1 ZICBYUSXNWXXIS-INIZCTEOSA-N 0.000 claims 1
- QKIVFQZUZVLIAM-INIZCTEOSA-N (2s)-2-amino-1-[4-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1CN(C(=O)[C@@H](N)C)CCN1CC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 QKIVFQZUZVLIAM-INIZCTEOSA-N 0.000 claims 1
- PVKSQMSGRBLQGL-IRXDYDNUSA-N (2s)-2-hydroxy-1-[(3s)-4-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-3-methylpiperazin-1-yl]propan-1-one Chemical compound C[C@H]1CN(C(=O)[C@@H](O)C)CCN1CC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 PVKSQMSGRBLQGL-IRXDYDNUSA-N 0.000 claims 1
- GXBJQIWAKQITMY-SFHVURJKSA-N (2s)-2-hydroxy-1-[4-[(4-morpholin-4-yl-2-quinolin-3-ylthieno[2,3-d]pyrimidin-6-yl)methyl]piperazin-1-yl]propan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=C4C=CC=CC4=NC=3)N=C2S1 GXBJQIWAKQITMY-SFHVURJKSA-N 0.000 claims 1
- BVNMKKCTXYKDQA-IBGZPJMESA-N (2s)-2-hydroxy-1-[4-[(7-methyl-4-morpholin-4-yl-2-quinolin-3-ylthieno[3,2-d]pyrimidin-6-yl)methyl]piperazin-1-yl]propan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=C(C)C2=NC(C=3C=C4C=CC=CC4=NC=3)=NC(N3CCOCC3)=C2S1 BVNMKKCTXYKDQA-IBGZPJMESA-N 0.000 claims 1
- CDXCQZQWDIQYSC-INIZCTEOSA-N (2s)-2-hydroxy-1-[4-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=4C=NNC=4C=CC=3)N=C2S1 CDXCQZQWDIQYSC-INIZCTEOSA-N 0.000 claims 1
- JPFJDPRZHNLDPU-INIZCTEOSA-N (2s)-2-hydroxy-1-[4-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 JPFJDPRZHNLDPU-INIZCTEOSA-N 0.000 claims 1
- UUQJATLCIXEDRM-KRWDZBQOSA-N (2s)-2-hydroxy-1-[4-[[2-(1h-indazol-4-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=C(C)C2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 UUQJATLCIXEDRM-KRWDZBQOSA-N 0.000 claims 1
- BQAIDJUOAYSYIC-INIZCTEOSA-N (2s)-2-hydroxy-1-[4-[[4-morpholin-4-yl-2-(1h-pyrrolo[2,3-b]pyridin-5-yl)thieno[2,3-d]pyrimidin-6-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=C4C=CNC4=NC=3)N=C2S1 BQAIDJUOAYSYIC-INIZCTEOSA-N 0.000 claims 1
- LYDJLZZJEFUYEY-KRWDZBQOSA-N (2s)-2-hydroxy-1-[4-[[7-methyl-4-morpholin-4-yl-2-(1h-pyrrolo[2,3-b]pyridin-5-yl)thieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]propan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=C(C)C2=NC(C=3C=C4C=CNC4=NC=3)=NC(N3CCOCC3)=C2S1 LYDJLZZJEFUYEY-KRWDZBQOSA-N 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
- AICIYIDUYNFPRY-UHFFFAOYSA-N 1,3-dihydro-2H-imidazol-2-one Chemical compound O=C1NC=CN1 AICIYIDUYNFPRY-UHFFFAOYSA-N 0.000 claims 1
- JIBGKAQMDUIEDD-UHFFFAOYSA-N 1-(2-hydroxyethyl)-4-[[2-(3-hydroxyphenyl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-2-one Chemical compound C1C(=O)N(CCO)CCN1CC1=CC2=NC(C=3C=C(O)C=CC=3)=NC(N3CCOCC3)=C2S1 JIBGKAQMDUIEDD-UHFFFAOYSA-N 0.000 claims 1
- MMBHBPJFZCRXRR-UHFFFAOYSA-N 1-[4-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-methoxyethanone Chemical compound C1CN(C(=O)COC)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=4C=NNC=4C=CC=3)N=C2S1 MMBHBPJFZCRXRR-UHFFFAOYSA-N 0.000 claims 1
- PGKUATHXECPBSJ-UHFFFAOYSA-N 1-[4-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-1-methylsulfonylpiperazin-2-yl]-n,n-dimethylmethanamine Chemical compound C1CN(S(C)(=O)=O)C(CN(C)C)CN1CC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 PGKUATHXECPBSJ-UHFFFAOYSA-N 0.000 claims 1
- LVYJJYJITZRRKF-UHFFFAOYSA-N 1-[4-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2,2-dimethylpropan-1-one Chemical compound C1CN(C(=O)C(C)(C)C)CCN1CC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 LVYJJYJITZRRKF-UHFFFAOYSA-N 0.000 claims 1
- QHKIFGQSLRELMC-UHFFFAOYSA-N 1-[4-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-methoxyethanone Chemical compound C1CN(C(=O)COC)CCN1CC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 QHKIFGQSLRELMC-UHFFFAOYSA-N 0.000 claims 1
- BNECHDGJUWPHJT-UHFFFAOYSA-N 1-[4-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 BNECHDGJUWPHJT-UHFFFAOYSA-N 0.000 claims 1
- UWGNCLDVQNASAX-UHFFFAOYSA-N 1-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]-4-methylsulfonylpiperazin-2-one Chemical compound O=C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 UWGNCLDVQNASAX-UHFFFAOYSA-N 0.000 claims 1
- BPMRPDPJLQDVAI-UHFFFAOYSA-N 1-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperidin-3-ol Chemical compound C1C(O)CCCN1CC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 BPMRPDPJLQDVAI-UHFFFAOYSA-N 0.000 claims 1
- SEMGFPHFAYFWSW-UHFFFAOYSA-N 1-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 SEMGFPHFAYFWSW-UHFFFAOYSA-N 0.000 claims 1
- NUPQYKHVSSKCSL-UHFFFAOYSA-N 1-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]pyrrolidin-3-ol Chemical compound C1C(O)CCN1CC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 NUPQYKHVSSKCSL-UHFFFAOYSA-N 0.000 claims 1
- GMQPIGJXSZAXSJ-UHFFFAOYSA-N 1-methylsulfonylpyrrolidine Chemical compound CS(=O)(=O)N1CCCC1 GMQPIGJXSZAXSJ-UHFFFAOYSA-N 0.000 claims 1
- DUADTZHKSSLGKG-UHFFFAOYSA-N 2,3-difluoro-5-[6-[(4-methylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]phenol Chemical compound C1CN(C)CCN1CC1=CC2=NC(C=3C=C(F)C(F)=C(O)C=3)=NC(N3CCOCC3)=C2S1 DUADTZHKSSLGKG-UHFFFAOYSA-N 0.000 claims 1
- UKHJNJFJCGBKSF-UHFFFAOYSA-N 2,5-diazabicyclo[2.2.1]heptane Chemical compound C1NC2CNC1C2 UKHJNJFJCGBKSF-UHFFFAOYSA-N 0.000 claims 1
- DWGVKILTTARRCT-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylfuro[2,3-d]pyrimidine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=4C=NNC=4C=CC=3)N=C2O1 DWGVKILTTARRCT-UHFFFAOYSA-N 0.000 claims 1
- BHHHVZLVHGUWMT-UHFFFAOYSA-N 2-(1h-indazol-4-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylfuro[3,2-d]pyrimidine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2O1 BHHHVZLVHGUWMT-UHFFFAOYSA-N 0.000 claims 1
- XPPPRGRKHWMZJC-UHFFFAOYSA-N 2-(1h-indol-4-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]-4-morpholin-4-ylfuro[3,2-d]pyrimidine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=4C=CNC=4C=CC=3)=NC(N3CCOCC3)=C2O1 XPPPRGRKHWMZJC-UHFFFAOYSA-N 0.000 claims 1
- UGCSVAPZKCAXCB-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)CN(C)C)CCN1CC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 UGCSVAPZKCAXCB-UHFFFAOYSA-N 0.000 claims 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims 1
- JZNDWSMUBHDDGP-UHFFFAOYSA-N 2-[4-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-n,2-dimethylpropanamide Chemical compound C1CN(C(C)(C)C(=O)NC)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=4C=NNC=4C=CC=3)N=C2S1 JZNDWSMUBHDDGP-UHFFFAOYSA-N 0.000 claims 1
- CKNTTYJBAVQSKT-UHFFFAOYSA-N 2-[4-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-n,n-dimethylacetamide Chemical compound C1CN(CC(=O)N(C)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=4C=NNC=4C=CC=3)N=C2S1 CKNTTYJBAVQSKT-UHFFFAOYSA-N 0.000 claims 1
- WNXNOFZKYRTQSA-UHFFFAOYSA-N 2-[4-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-methylpropanamide Chemical compound C1CN(C(C)(C)C(N)=O)CCN1CC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 WNXNOFZKYRTQSA-UHFFFAOYSA-N 0.000 claims 1
- GUKBWHKSZLXZJN-UHFFFAOYSA-N 2-amino-1-[4-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-methylpropan-1-one Chemical compound C1CN(C(=O)C(C)(N)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=4C=NNC=4C=CC=3)N=C2S1 GUKBWHKSZLXZJN-UHFFFAOYSA-N 0.000 claims 1
- WCURVACCQSMZBI-UHFFFAOYSA-N 2-amino-1-[4-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)CN)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=4C=NNC=4C=CC=3)N=C2S1 WCURVACCQSMZBI-UHFFFAOYSA-N 0.000 claims 1
- JDZJQFBISMUXST-UHFFFAOYSA-N 2-amino-1-[4-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-methylpropan-1-one Chemical compound C1CN(C(=O)C(C)(N)C)CCN1CC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 JDZJQFBISMUXST-UHFFFAOYSA-N 0.000 claims 1
- TWSSNXIPIIXPFW-UHFFFAOYSA-N 2-amino-1-[4-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)CN)CCN1CC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 TWSSNXIPIIXPFW-UHFFFAOYSA-N 0.000 claims 1
- ODNOCHZJHOYPOF-UHFFFAOYSA-N 2-chloro-5-[6-[(4-methylpiperazin-1-yl)methyl]-4-morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl]phenol Chemical compound C1CN(C)CCN1CC1=CC2=NC(C=3C=C(O)C(Cl)=CC=3)=NC(N3CCOCC3)=C2S1 ODNOCHZJHOYPOF-UHFFFAOYSA-N 0.000 claims 1
- QQGAIWIXCORTKC-UHFFFAOYSA-N 2-hydroxy-1-[4-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-methylpropan-1-one Chemical compound C1CN(C(=O)C(C)(O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=4C=NNC=4C=CC=3)N=C2S1 QQGAIWIXCORTKC-UHFFFAOYSA-N 0.000 claims 1
- RMZQEDHENJXBDQ-UHFFFAOYSA-N 2-hydroxy-1-[4-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[2,3-d]pyrimidin-6-yl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)CO)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=4C=NNC=4C=CC=3)N=C2S1 RMZQEDHENJXBDQ-UHFFFAOYSA-N 0.000 claims 1
- XGHDYSSANLOUIZ-UHFFFAOYSA-N 2-hydroxy-1-[4-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-methylpropan-1-one Chemical compound C1CN(C(=O)C(C)(O)C)CCN1CC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 XGHDYSSANLOUIZ-UHFFFAOYSA-N 0.000 claims 1
- INXZAWHDKBTQER-UHFFFAOYSA-N 2-hydroxy-1-[4-[[2-(1h-indazol-4-yl)-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)CO)CCN1CC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 INXZAWHDKBTQER-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
- KRIOSGCRUOYJCW-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-5-methyl-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound S1C2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2C(C)=C1CN1CCN(S(C)(=O)=O)CC1 KRIOSGCRUOYJCW-UHFFFAOYSA-N 0.000 claims 1
- SZKHPORALUTOIT-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-[(1-methylpiperidin-4-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(C)CCC1CC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 SZKHPORALUTOIT-UHFFFAOYSA-N 0.000 claims 1
- KLWXCRAMVFYALJ-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-[(3-methylsulfonylpyrrolidin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1C(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 KLWXCRAMVFYALJ-UHFFFAOYSA-N 0.000 claims 1
- YIIAIAMYILXXID-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-[(4-methylpiperazin-1-yl)methyl]thieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=4C=NNC=4C=CC=3)N=C2S1 YIIAIAMYILXXID-UHFFFAOYSA-N 0.000 claims 1
- KHPPAYVCPJDDEN-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-[(4-methylsulfonyl-1,4-diazepan-1-yl)methyl]thieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=4C=NNC=4C=CC=3)N=C2S1 KHPPAYVCPJDDEN-UHFFFAOYSA-N 0.000 claims 1
- GVKWJWXRSWROJM-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=4C=NNC=4C=CC=3)N=C2S1 GVKWJWXRSWROJM-UHFFFAOYSA-N 0.000 claims 1
- ROBHRNWYGPEJRN-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-[(4-methylsulfonylpiperidin-1-yl)methyl]thieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1CC(S(=O)(=O)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=4C=NNC=4C=CC=3)N=C2S1 ROBHRNWYGPEJRN-UHFFFAOYSA-N 0.000 claims 1
- WBFYBYYGXLSLDN-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-[(4-morpholin-4-ylsulfonylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(CC=2SC3=C(N4CCOCC4)N=C(N=C3C=2)C=2C=3C=NNC=3C=CC=2)CCN1S(=O)(=O)N1CCOCC1 WBFYBYYGXLSLDN-UHFFFAOYSA-N 0.000 claims 1
- FBZMWDQPFNSHMJ-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-6-[(4-propan-2-ylsulfonylpiperazin-1-yl)methyl]thieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(S(=O)(=O)C(C)C)CCN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=4C=NNC=4C=CC=3)N=C2S1 FBZMWDQPFNSHMJ-UHFFFAOYSA-N 0.000 claims 1
- FJCGRTLENBLXEU-HOTGVXAUSA-N 4-[2-(1h-indazol-4-yl)-6-[[(1s,4s)-2-methylsulfonyl-2,5-diazabicyclo[2.2.1]heptan-5-yl]methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C([C@]1(N(C[C@@]2(C1)[H])S(C)(=O)=O)[H])N2CC(SC1=2)=CC1=NC(C=1C=3C=NNC=3C=CC=1)=NC=2N1CCOCC1 FJCGRTLENBLXEU-HOTGVXAUSA-N 0.000 claims 1
- IKJCMLBQDGQADJ-INIZCTEOSA-N 4-[2-(1h-indazol-4-yl)-6-[[(2s)-2-methyl-4-methylsulfonylpiperazin-1-yl]methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C[C@H]1CN(S(C)(=O)=O)CCN1CC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 IKJCMLBQDGQADJ-INIZCTEOSA-N 0.000 claims 1
- UUBDDDXEIWKERC-MRXNPFEDSA-N 4-[2-(1h-indazol-4-yl)-6-[[(3r)-3-methyl-4-methylsulfonylpiperazin-1-yl]methyl]thieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(S(C)(=O)=O)[C@H](C)CN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=4C=NNC=4C=CC=3)N=C2S1 UUBDDDXEIWKERC-MRXNPFEDSA-N 0.000 claims 1
- HDFWXGOBDYWYSF-MRXNPFEDSA-N 4-[2-(1h-indazol-4-yl)-6-[[(3r)-3-methyl-4-methylsulfonylpiperazin-1-yl]methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(S(C)(=O)=O)[C@H](C)CN1CC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 HDFWXGOBDYWYSF-MRXNPFEDSA-N 0.000 claims 1
- UUBDDDXEIWKERC-INIZCTEOSA-N 4-[2-(1h-indazol-4-yl)-6-[[(3s)-3-methyl-4-methylsulfonylpiperazin-1-yl]methyl]thieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(S(C)(=O)=O)[C@@H](C)CN1CC1=CC2=C(N3CCOCC3)N=C(C=3C=4C=NNC=4C=CC=3)N=C2S1 UUBDDDXEIWKERC-INIZCTEOSA-N 0.000 claims 1
- CCPONEARNIDXLI-UHFFFAOYSA-N 4-[2-(1h-indazol-4-yl)-7-methyl-6-[(4-methylsulfonylpiperidin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound S1C2=C(N3CCOCC3)N=C(C=3C=4C=NNC=4C=CC=3)N=C2C(C)=C1CN1CCC(S(C)(=O)=O)CC1 CCPONEARNIDXLI-UHFFFAOYSA-N 0.000 claims 1
- ROXGZIZXQHQKHW-UHFFFAOYSA-N 4-[2-(1h-indazol-6-yl)-6-[(4-methylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(C)CCN1CC1=CC2=NC(C=3C=C4NN=CC4=CC=3)=NC(N3CCOCC3)=C2S1 ROXGZIZXQHQKHW-UHFFFAOYSA-N 0.000 claims 1
- MFRGFJVZAMAGTF-UHFFFAOYSA-N 4-[2-(2-fluoropyridin-3-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[3,2-d]pyrimidin-4-yl]morpholine Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C(=NC=CC=3)F)=NC(N3CCOCC3)=C2S1 MFRGFJVZAMAGTF-UHFFFAOYSA-N 0.000 claims 1
- NLMFRVKNYWWMPO-UHFFFAOYSA-N 4-[2-(2-methoxypyrimidin-5-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C1=NC(OC)=NC=C1C1=NC(N2CCOCC2)=C(C=C(CN2CCN(CC2)S(C)(=O)=O)S2)C2=N1 NLMFRVKNYWWMPO-UHFFFAOYSA-N 0.000 claims 1
- BJSSQKCPTWQLAS-UHFFFAOYSA-N 4-[2-(2-methyl-1h-imidazo[4,5-b]pyridin-6-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C=1N=C2NC(C)=NC2=CC=1C(N=C1SC(CN2CCN(CC2)S(C)(=O)=O)=CC1=1)=NC=1N1CCOCC1 BJSSQKCPTWQLAS-UHFFFAOYSA-N 0.000 claims 1
- GEHMSILAXBVEEP-UHFFFAOYSA-N 4-[2-(2-methyl-3h-benzimidazol-5-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound C=1C=C2NC(C)=NC2=CC=1C(N=C1SC(CN2CCN(CC2)S(C)(=O)=O)=CC1=1)=NC=1N1CCOCC1 GEHMSILAXBVEEP-UHFFFAOYSA-N 0.000 claims 1
- DXNXFGCNNZWHKC-UHFFFAOYSA-N 4-[2-(2-methylbenzimidazol-1-yl)-6-[(4-methylsulfonylpiperazin-1-yl)methyl]thieno[2,3-d]pyrimidin-4-yl]morpholine Chemical compound CC1=NC2=CC=CC=C2N1C(N=C1SC(CN2CCN(CC2)S(C)(=O)=O)=CC1=1)=NC=1N1CCOCC1 DXNXFGCNNZWHKC-UHFFFAOYSA-N 0.000 claims 1
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- 2007-04-24 ES ES07755937T patent/ES2377358T3/es active Active
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- 2007-04-24 CN CN2007800237053A patent/CN101479274B/zh active Active
- 2007-04-24 EP EP11177850A patent/EP2402347A1/en not_active Withdrawn
- 2007-04-24 CA CA2650290A patent/CA2650290C/en not_active Expired - Fee Related
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