KR20110046514A - 피리미딘 화합물, 조성물 및 사용 방법 - Google Patents
피리미딘 화합물, 조성물 및 사용 방법 Download PDFInfo
- Publication number
- KR20110046514A KR20110046514A KR1020117004629A KR20117004629A KR20110046514A KR 20110046514 A KR20110046514 A KR 20110046514A KR 1020117004629 A KR1020117004629 A KR 1020117004629A KR 20117004629 A KR20117004629 A KR 20117004629A KR 20110046514 A KR20110046514 A KR 20110046514A
- Authority
- KR
- South Korea
- Prior art keywords
- phenyl
- pyrimidin
- tetrahydropyrido
- group
- urea
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims description 197
- 239000000203 mixture Substances 0.000 title description 105
- 150000003230 pyrimidines Chemical class 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 379
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 55
- 102000013530 TOR Serine-Threonine Kinases Human genes 0.000 claims abstract description 48
- 108010065917 TOR Serine-Threonine Kinases Proteins 0.000 claims abstract description 48
- 201000011510 cancer Diseases 0.000 claims abstract description 46
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 37
- 150000003839 salts Chemical class 0.000 claims abstract description 34
- 201000010099 disease Diseases 0.000 claims abstract description 22
- -1 selected from N Inorganic materials 0.000 claims description 408
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 227
- 125000000217 alkyl group Chemical group 0.000 claims description 109
- 125000001424 substituent group Chemical group 0.000 claims description 89
- 229910052739 hydrogen Inorganic materials 0.000 claims description 65
- 239000001257 hydrogen Substances 0.000 claims description 65
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 63
- 125000003118 aryl group Chemical group 0.000 claims description 58
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 56
- 229910052757 nitrogen Inorganic materials 0.000 claims description 55
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 48
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 44
- 125000005842 heteroatom Chemical group 0.000 claims description 44
- 150000002431 hydrogen Chemical group 0.000 claims description 42
- 125000001072 heteroaryl group Chemical group 0.000 claims description 41
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 38
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 37
- 229910052801 chlorine Inorganic materials 0.000 claims description 36
- 229910052731 fluorine Inorganic materials 0.000 claims description 36
- 229910052736 halogen Inorganic materials 0.000 claims description 36
- 229910052794 bromium Inorganic materials 0.000 claims description 35
- 229910052740 iodine Inorganic materials 0.000 claims description 35
- 229910052717 sulfur Inorganic materials 0.000 claims description 34
- 150000002367 halogens Chemical class 0.000 claims description 33
- 125000004429 atom Chemical group 0.000 claims description 32
- 229910052760 oxygen Inorganic materials 0.000 claims description 32
- 125000000623 heterocyclic group Chemical group 0.000 claims description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims description 24
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 241000124008 Mammalia Species 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 16
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 15
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 15
- 238000011282 treatment Methods 0.000 claims description 15
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- 230000000694 effects Effects 0.000 claims description 13
- 201000009030 Carcinoma Diseases 0.000 claims description 12
- 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 10
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 10
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 10
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 9
- 206010009944 Colon cancer Diseases 0.000 claims description 9
- 108010035196 Mechanistic Target of Rapamycin Complex 1 Proteins 0.000 claims description 9
- 102000008135 Mechanistic Target of Rapamycin Complex 1 Human genes 0.000 claims description 9
- 208000015634 Rectal Neoplasms Diseases 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 206010038038 rectal cancer Diseases 0.000 claims description 9
- 201000001275 rectum cancer Diseases 0.000 claims description 9
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 8
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 8
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 7
- 206010038389 Renal cancer Diseases 0.000 claims description 7
- 239000002246 antineoplastic agent Substances 0.000 claims description 7
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 7
- 125000005551 pyridylene group Chemical group 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
- 206010006187 Breast cancer Diseases 0.000 claims description 6
- 208000026310 Breast neoplasm Diseases 0.000 claims description 6
- 208000010667 Carcinoma of liver and intrahepatic biliary tract Diseases 0.000 claims description 6
- 206010073069 Hepatic cancer Diseases 0.000 claims description 6
- 208000003445 Mouth Neoplasms Diseases 0.000 claims description 6
- 206010033128 Ovarian cancer Diseases 0.000 claims description 6
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 6
- 206010039491 Sarcoma Diseases 0.000 claims description 6
- 208000009956 adenocarcinoma Diseases 0.000 claims description 6
- 125000004450 alkenylene group Chemical group 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- 208000032839 leukemia Diseases 0.000 claims description 6
- 208000012987 lip and oral cavity carcinoma Diseases 0.000 claims description 6
- 201000002250 liver carcinoma Diseases 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 208000009565 Pharyngeal Neoplasms Diseases 0.000 claims description 5
- 206010034811 Pharyngeal cancer Diseases 0.000 claims description 5
- 206010060862 Prostate cancer Diseases 0.000 claims description 5
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 5
- 208000005718 Stomach Neoplasms Diseases 0.000 claims description 5
- 208000029742 colonic neoplasm Diseases 0.000 claims description 5
- 206010017758 gastric cancer Diseases 0.000 claims description 5
- 208000005017 glioblastoma Diseases 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 208000018555 lymphatic system disease Diseases 0.000 claims description 5
- 125000002950 monocyclic group Chemical group 0.000 claims description 5
- 208000000649 small cell carcinoma Diseases 0.000 claims description 5
- 201000011549 stomach cancer Diseases 0.000 claims description 5
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
- 206010005003 Bladder cancer Diseases 0.000 claims description 4
- 206010008342 Cervix carcinoma Diseases 0.000 claims description 4
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 4
- 208000008839 Kidney Neoplasms Diseases 0.000 claims description 4
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 4
- 208000018501 Lymphatic disease Diseases 0.000 claims description 4
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 4
- 208000024770 Thyroid neoplasm Diseases 0.000 claims description 4
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 4
- 201000010881 cervical cancer Diseases 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 229940127089 cytotoxic agent Drugs 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 4
- 201000010982 kidney cancer Diseases 0.000 claims description 4
- 201000005249 lung adenocarcinoma Diseases 0.000 claims description 4
- 208000020816 lung neoplasm Diseases 0.000 claims description 4
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 4
- 201000001441 melanoma Diseases 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 201000002528 pancreatic cancer Diseases 0.000 claims description 4
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 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 description 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 201000002510 thyroid cancer Diseases 0.000 claims description 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 3
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 3
- 125000006591 (C2-C6) alkynylene group Chemical group 0.000 claims description 3
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 3
- 208000010507 Adenocarcinoma of Lung Diseases 0.000 claims description 3
- 206010005949 Bone cancer Diseases 0.000 claims description 3
- 208000018084 Bone neoplasm Diseases 0.000 claims description 3
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims description 3
- 206010023825 Laryngeal cancer Diseases 0.000 claims description 3
- 108010034057 Mechanistic Target of Rapamycin Complex 2 Proteins 0.000 claims description 3
- 102000009308 Mechanistic Target of Rapamycin Complex 2 Human genes 0.000 claims description 3
- 206010029260 Neuroblastoma Diseases 0.000 claims description 3
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims description 3
- 208000006265 Renal cell carcinoma Diseases 0.000 claims description 3
- 208000000453 Skin Neoplasms Diseases 0.000 claims description 3
- 208000024313 Testicular Neoplasms Diseases 0.000 claims description 3
- 206010057644 Testis cancer Diseases 0.000 claims description 3
- 201000001531 bladder carcinoma Diseases 0.000 claims description 3
- 208000015322 bone marrow disease Diseases 0.000 claims description 3
- 201000007455 central nervous system cancer Diseases 0.000 claims description 3
- 208000006990 cholangiocarcinoma Diseases 0.000 claims description 3
- 206010009259 cleft lip Diseases 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 201000004101 esophageal cancer Diseases 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000005549 heteroarylene group Chemical group 0.000 claims description 3
- 208000003849 large cell carcinoma Diseases 0.000 claims description 3
- 206010023841 laryngeal neoplasm Diseases 0.000 claims description 3
- 201000005202 lung cancer Diseases 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- 201000010198 papillary carcinoma Diseases 0.000 claims description 3
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 201000010174 renal carcinoma Diseases 0.000 claims description 3
- 201000000849 skin cancer Diseases 0.000 claims description 3
- 201000003120 testicular cancer Diseases 0.000 claims description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
- 208000030901 thyroid gland follicular carcinoma Diseases 0.000 claims description 3
- 125000004306 triazinyl group Chemical group 0.000 claims description 3
- 125000001425 triazolyl group Chemical group 0.000 claims description 3
- 208000010576 undifferentiated carcinoma Diseases 0.000 claims description 3
- 208000010570 urinary bladder carcinoma Diseases 0.000 claims description 3
- 125000004503 1,2,3-oxadiazol-5-yl group Chemical group O1N=NC=C1* 0.000 claims description 2
- 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 claims description 2
- 125000004510 1,3,4-oxadiazol-5-yl group Chemical group O1C=NN=C1* 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 2
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 2
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 2
- 208000003174 Brain Neoplasms Diseases 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims description 2
- 125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 claims description 2
- 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims description 2
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims description 2
- 125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 claims description 2
- 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 claims description 2
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 claims description 2
- 125000005494 pyridonyl group Chemical group 0.000 claims description 2
- 125000005576 pyrimidinylene group Chemical group 0.000 claims description 2
- 201000002314 small intestine cancer Diseases 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- 240000000662 Anethum graveolens Species 0.000 claims 1
- 208000001126 Keratosis Diseases 0.000 claims 1
- 206010062129 Tongue neoplasm Diseases 0.000 claims 1
- 201000006134 tongue cancer Diseases 0.000 claims 1
- 239000002207 metabolite Substances 0.000 abstract description 25
- 239000012453 solvate Substances 0.000 abstract description 16
- 230000011664 signaling Effects 0.000 abstract description 10
- 108091000080 Phosphotransferase Proteins 0.000 abstract description 4
- 230000001404 mediated effect Effects 0.000 abstract description 4
- 102000020233 phosphotransferase Human genes 0.000 abstract description 4
- 230000008482 dysregulation Effects 0.000 abstract description 3
- 230000019491 signal transduction Effects 0.000 abstract description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 361
- 238000003786 synthesis reaction Methods 0.000 description 183
- 230000015572 biosynthetic process Effects 0.000 description 179
- 239000004202 carbamide Substances 0.000 description 145
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 132
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 59
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 49
- RBAHQUJAZVTPMS-UHFFFAOYSA-N 4-[2-chloro-7-(2-methoxyethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-4-yl]-3,3-dimethylmorpholine Chemical compound C1N(CCOC)CCC2=C1N=C(Cl)N=C2N1CCOCC1(C)C RBAHQUJAZVTPMS-UHFFFAOYSA-N 0.000 description 46
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 41
- 238000006243 chemical reaction Methods 0.000 description 39
- 239000000047 product Substances 0.000 description 35
- 238000009472 formulation Methods 0.000 description 33
- 239000000460 chlorine Substances 0.000 description 29
- 229940002612 prodrug Drugs 0.000 description 28
- 239000000651 prodrug Substances 0.000 description 28
- 239000004480 active ingredient Substances 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 26
- 239000007787 solid Substances 0.000 description 26
- 239000003112 inhibitor Substances 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 15
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 210000004027 cell Anatomy 0.000 description 15
- 208000035475 disorder Diseases 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 208000024891 symptom Diseases 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 13
- 230000006824 pyrimidine synthesis Effects 0.000 description 13
- 239000000741 silica gel Substances 0.000 description 13
- 229910002027 silica gel Inorganic materials 0.000 description 13
- QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 description 13
- 229960005419 nitrogen Drugs 0.000 description 12
- 229960002930 sirolimus Drugs 0.000 description 12
- BYHDTZHNPIWVOP-UHFFFAOYSA-N 1-ethyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1B1OC(C)(C)C(C)(C)O1 BYHDTZHNPIWVOP-UHFFFAOYSA-N 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 235000019439 ethyl acetate Nutrition 0.000 description 11
- ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 description 11
- QCGMEWVZBGQOFN-UHFFFAOYSA-N 1,3-oxazole-5-carboxylic acid Chemical compound OC(=O)C1=CN=CO1 QCGMEWVZBGQOFN-UHFFFAOYSA-N 0.000 description 10
- DXVKXAXORGPVCN-AWEZNQCLSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCNC2 DXVKXAXORGPVCN-AWEZNQCLSA-N 0.000 description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 238000013459 approach Methods 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- WUYSMOCOXBLFKK-UHFFFAOYSA-N tert-butyl 2,4-dichloro-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylate Chemical compound ClC1=NC(Cl)=C2CN(C(=O)OC(C)(C)C)CC2=N1 WUYSMOCOXBLFKK-UHFFFAOYSA-N 0.000 description 10
- MVCATBQMPZIZHF-NSHDSACASA-N tert-butyl 2-chloro-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C[C@H]1COCCN1C1=NC(Cl)=NC2=C1CCN(C(=O)OC(C)(C)C)C2 MVCATBQMPZIZHF-NSHDSACASA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 9
- 239000003826 tablet Substances 0.000 description 9
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 8
- UNCQVRBWJWWJBF-UHFFFAOYSA-N 2-chloropyrimidine Chemical compound ClC1=NC=CC=N1 UNCQVRBWJWWJBF-UHFFFAOYSA-N 0.000 description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 229940079593 drug Drugs 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 231100000252 nontoxic Toxicity 0.000 description 8
- 230000003000 nontoxic effect Effects 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- ZXQOTUSTYCUIBX-UHFFFAOYSA-N 1-ethyl-3-[4-(4-morpholin-4-yl-6-pyrimidin-2-yl-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-yl)phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(C=1N=CC=CN=1)C2 ZXQOTUSTYCUIBX-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 238000004007 reversed phase HPLC Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- SAEOMPAQDWZLHC-UHFFFAOYSA-N tert-butyl 2,4-dichloro-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound N1=C(Cl)N=C2CN(C(=O)OC(C)(C)C)CCC2=C1Cl SAEOMPAQDWZLHC-UHFFFAOYSA-N 0.000 description 7
- 230000001225 therapeutic effect Effects 0.000 description 7
- 238000002560 therapeutic procedure Methods 0.000 description 7
- PYEQIBJLQHFWDP-OGFXRTJISA-N (3s)-3-propan-2-ylmorpholine;hydrobromide Chemical compound Br.CC(C)[C@H]1COCCN1 PYEQIBJLQHFWDP-OGFXRTJISA-N 0.000 description 6
- ICPFKVCUIBCOAP-UHFFFAOYSA-N 1-ethyl-3-[4-(4-morpholin-4-yl-6,7-dihydro-5h-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CNC2 ICPFKVCUIBCOAP-UHFFFAOYSA-N 0.000 description 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
- IFXGTTGFKFJPRP-UHFFFAOYSA-N 4,5-dihydropyrimidine-6-carboxylic acid Chemical compound OC(=O)C1=NC=NCC1 IFXGTTGFKFJPRP-UHFFFAOYSA-N 0.000 description 6
- ICORGBQIQCSEBP-UHFFFAOYSA-N 4-(5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)morpholine Chemical compound C=12CNCCC2=NC=NC=1N1CCOCC1 ICORGBQIQCSEBP-UHFFFAOYSA-N 0.000 description 6
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 6
- 241000282412 Homo Species 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 description 6
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 6
- 125000002619 bicyclic group Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 238000003818 flash chromatography Methods 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 238000012552 review Methods 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 6
- QUBKJRRBXYPWAI-RGMNGODLSA-N (3s)-3-ethylmorpholine;hydrobromide Chemical compound Br.CC[C@H]1COCCN1 QUBKJRRBXYPWAI-RGMNGODLSA-N 0.000 description 5
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 5
- DAOZBJCTEPJGES-UHFFFAOYSA-N 4-chloro-2-methylpyridine Chemical compound CC1=CC(Cl)=CC=N1 DAOZBJCTEPJGES-UHFFFAOYSA-N 0.000 description 5
- DBGFGNCFYUNXLD-UHFFFAOYSA-N 4-chloropyrimidin-2-amine Chemical compound NC1=NC=CC(Cl)=N1 DBGFGNCFYUNXLD-UHFFFAOYSA-N 0.000 description 5
- IDGJKKLWXZTBOV-UHFFFAOYSA-N 6-benzyl-4-morpholin-4-yl-2-(4-nitrophenyl)-5h-pyrrolo[3,4-d]pyrimidin-7-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(CC=1C=CC=CC=1)C2=O IDGJKKLWXZTBOV-UHFFFAOYSA-N 0.000 description 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 5
- 102000038030 PI3Ks Human genes 0.000 description 5
- 108091007960 PI3Ks Proteins 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 5
- 239000006071 cream Substances 0.000 description 5
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 5
- IGSKHXTUVXSOMB-UHFFFAOYSA-N cyclopropylmethanamine Chemical compound NCC1CC1 IGSKHXTUVXSOMB-UHFFFAOYSA-N 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 238000001727 in vivo Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000003755 preservative agent Substances 0.000 description 5
- 108090000623 proteins and genes Proteins 0.000 description 5
- 150000003384 small molecules Chemical class 0.000 description 5
- VGPJCPSNRASZFH-UHFFFAOYSA-N tert-butyl 2-(4-aminophenyl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC2=C1N=C(C=1C=CC(N)=CC=1)N=C2N1CCOCC1 VGPJCPSNRASZFH-UHFFFAOYSA-N 0.000 description 5
- 239000003039 volatile agent Substances 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 4
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical group OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 4
- ILMDMEXCJKULNN-UHFFFAOYSA-N 6-benzyl-1,5-dihydropyrrolo[3,4-d]pyrimidine-2,4,7-trione Chemical compound C1C(C(NC(=O)N2)=O)=C2C(=O)N1CC1=CC=CC=C1 ILMDMEXCJKULNN-UHFFFAOYSA-N 0.000 description 4
- RIQWFOVEZFDBBP-UHFFFAOYSA-N 6-benzyl-2,4-dichloro-5h-pyrrolo[3,4-d]pyrimidin-7-one Chemical compound C1C=2C(Cl)=NC(Cl)=NC=2C(=O)N1CC1=CC=CC=C1 RIQWFOVEZFDBBP-UHFFFAOYSA-N 0.000 description 4
- 230000007730 Akt signaling Effects 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 244000099147 Ananas comosus Species 0.000 description 4
- 235000007119 Ananas comosus Nutrition 0.000 description 4
- 208000024172 Cardiovascular disease Diseases 0.000 description 4
- 102000004127 Cytokines Human genes 0.000 description 4
- 108090000695 Cytokines Proteins 0.000 description 4
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 4
- 108010010803 Gelatin Proteins 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 4
- 229930006000 Sucrose Natural products 0.000 description 4
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 description 4
- MKEHYLIKGNWVRV-UHFFFAOYSA-N [4-(ethylcarbamoylamino)phenyl]boronic acid Chemical compound CCNC(=O)NC1=CC=C(B(O)O)C=C1 MKEHYLIKGNWVRV-UHFFFAOYSA-N 0.000 description 4
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 4
- 239000012346 acetyl chloride Substances 0.000 description 4
- 125000004423 acyloxy group Chemical group 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 229940024606 amino acid Drugs 0.000 description 4
- 235000001014 amino acid Nutrition 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 150000007942 carboxylates Chemical class 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 230000010261 cell growth Effects 0.000 description 4
- 238000002648 combination therapy Methods 0.000 description 4
- 239000013058 crude material Substances 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- AAKJLRGGTJKAMG-UHFFFAOYSA-N erlotinib Chemical class C=12C=C(OCCOC)C(OCCOC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 AAKJLRGGTJKAMG-UHFFFAOYSA-N 0.000 description 4
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 230000006870 function Effects 0.000 description 4
- 239000008273 gelatin Substances 0.000 description 4
- 229920000159 gelatin Polymers 0.000 description 4
- 235000019322 gelatine Nutrition 0.000 description 4
- 235000011852 gelatine desserts Nutrition 0.000 description 4
- 239000003102 growth factor Substances 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000003094 microcapsule Substances 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 239000006187 pill Substances 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 4
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 239000005720 sucrose Substances 0.000 description 4
- 125000004434 sulfur atom Chemical group 0.000 description 4
- 230000004083 survival effect Effects 0.000 description 4
- 239000000375 suspending agent Substances 0.000 description 4
- 239000003981 vehicle Substances 0.000 description 4
- MIPKQUBOFJEWEF-LBPRGKRZSA-N (3s)-3-ethyl-4-(4-methylphenyl)sulfonylmorpholine Chemical compound CC[C@H]1COCCN1S(=O)(=O)C1=CC=C(C)C=C1 MIPKQUBOFJEWEF-LBPRGKRZSA-N 0.000 description 3
- PVHLAMRYIZNXBI-UHFFFAOYSA-N 1-[4-(7-benzyl-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(CC=1C=CC=CC=1)C2 PVHLAMRYIZNXBI-UHFFFAOYSA-N 0.000 description 3
- TUXSNTZYUNPGSL-HNNXBMFYSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-methylsulfonyl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(S(C)(=O)=O)C2 TUXSNTZYUNPGSL-HNNXBMFYSA-N 0.000 description 3
- OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-N 0.000 description 3
- GELVZYOEQVJIRR-UHFFFAOYSA-N 2-chloropyrazine Chemical compound ClC1=CN=CC=N1 GELVZYOEQVJIRR-UHFFFAOYSA-N 0.000 description 3
- BMIBJCFFZPYJHF-UHFFFAOYSA-N 2-methoxy-5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound COC1=NC=C(C)C=C1B1OC(C)(C)C(C)(C)O1 BMIBJCFFZPYJHF-UHFFFAOYSA-N 0.000 description 3
- UZGLOGCJCWBBIV-UHFFFAOYSA-N 3-(chloromethyl)pyridin-1-ium;chloride Chemical compound Cl.ClCC1=CC=CN=C1 UZGLOGCJCWBBIV-UHFFFAOYSA-N 0.000 description 3
- WDTVJRYCMIZPMX-UHFFFAOYSA-N 4-chloro-2-methylpyrimidine Chemical compound CC1=NC=CC(Cl)=N1 WDTVJRYCMIZPMX-UHFFFAOYSA-N 0.000 description 3
- ZEHUTQGVUBWPFL-HNNXBMFYSA-N 6-[[5-[7-methyl-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]pyridin-2-yl]amino]-1h-pyridin-2-one Chemical compound C[C@H]1COCCN1C1=NC(C=2C=NC(NC=3NC(=O)C=CC=3)=CC=2)=NC2=C1CCN(C)C2 ZEHUTQGVUBWPFL-HNNXBMFYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- PTOAARAWEBMLNO-KVQBGUIXSA-N Cladribine Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)O1 PTOAARAWEBMLNO-KVQBGUIXSA-N 0.000 description 3
- UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 description 3
- 108010092160 Dactinomycin Proteins 0.000 description 3
- 206010014733 Endometrial cancer Diseases 0.000 description 3
- 206010014759 Endometrial neoplasm Diseases 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 3
- 240000007472 Leucaena leucocephala Species 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 description 3
- 102100027913 Peptidyl-prolyl cis-trans isomerase FKBP1A Human genes 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 206010037211 Psychomotor hyperactivity Diseases 0.000 description 3
- 108010006877 Tacrolimus Binding Protein 1A Proteins 0.000 description 3
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- RJURFGZVJUQBHK-IIXSONLDSA-N actinomycin D Chemical compound C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)N[C@@H]4C(=O)N[C@@H](C(N5CCC[C@H]5C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-IIXSONLDSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000000539 amino acid group Chemical group 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003125 aqueous solvent Substances 0.000 description 3
- 239000007900 aqueous suspension Substances 0.000 description 3
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical class C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 3
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
- 230000027455 binding Effects 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000002837 carbocyclic group Chemical group 0.000 description 3
- 150000001720 carbohydrates Chemical class 0.000 description 3
- 235000014633 carbohydrates Nutrition 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 230000004663 cell proliferation Effects 0.000 description 3
- 230000005754 cellular signaling Effects 0.000 description 3
- 238000002512 chemotherapy Methods 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 229960000640 dactinomycin Drugs 0.000 description 3
- STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 229940088598 enzyme Drugs 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 229940093915 gynecological organic acid Drugs 0.000 description 3
- UUVWYPNAQBNQJQ-UHFFFAOYSA-N hexamethylmelamine Chemical compound CN(C)C1=NC(N(C)C)=NC(N(C)C)=N1 UUVWYPNAQBNQJQ-UHFFFAOYSA-N 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 229940043355 kinase inhibitor Drugs 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 239000003628 mammalian target of rapamycin inhibitor Substances 0.000 description 3
- 229960004961 mechlorethamine Drugs 0.000 description 3
- HAWPXGHAZFHHAD-UHFFFAOYSA-N mechlorethamine Chemical class ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 description 3
- 230000004060 metabolic process Effects 0.000 description 3
- XOGAMPZSMNBPGH-UHFFFAOYSA-N methyl 2-[4-(ethylcarbamoylamino)phenyl]-4-morpholin-4-yl-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(C(=O)OC)C2 XOGAMPZSMNBPGH-UHFFFAOYSA-N 0.000 description 3
- RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 description 3
- CFCUWKMKBJTWLW-BKHRDMLASA-N mithramycin Chemical compound O([C@@H]1C[C@@H](O[C@H](C)[C@H]1O)OC=1C=C2C=C3C[C@H]([C@@H](C(=O)C3=C(O)C2=C(O)C=1C)O[C@@H]1O[C@H](C)[C@@H](O)[C@H](O[C@@H]2O[C@H](C)[C@H](O)[C@H](O[C@@H]3O[C@H](C)[C@@H](O)[C@@](C)(O)C3)C2)C1)[C@H](OC)C(=O)[C@@H](O)[C@@H](C)O)[C@H]1C[C@@H](O)[C@H](O)[C@@H](C)O1 CFCUWKMKBJTWLW-BKHRDMLASA-N 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 3
- 210000000214 mouth Anatomy 0.000 description 3
- 230000035772 mutation Effects 0.000 description 3
- 230000004770 neurodegeneration Effects 0.000 description 3
- 208000015122 neurodegenerative disease Diseases 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- 239000003757 phosphotransferase inhibitor Substances 0.000 description 3
- 229960003171 plicamycin Drugs 0.000 description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 235000018102 proteins Nutrition 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 3
- 238000001959 radiotherapy Methods 0.000 description 3
- 108020003175 receptors Proteins 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 238000013268 sustained release Methods 0.000 description 3
- 239000012730 sustained-release form Substances 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- NGBLEGHCNFJJEQ-UHFFFAOYSA-N tert-butyl 2-[4-(ethylcarbamoylamino)phenyl]-4-morpholin-4-yl-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(C(=O)OC(C)(C)C)C2 NGBLEGHCNFJJEQ-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 3
- 239000005483 tyrosine kinase inhibitor Substances 0.000 description 3
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- CGHYQZASLKERLV-UHFFFAOYSA-N (2-aminopyrimidin-5-yl)boronic acid Chemical compound NC1=NC=C(B(O)O)C=N1 CGHYQZASLKERLV-UHFFFAOYSA-N 0.000 description 2
- JCBPETKZIGVZRE-BYPYZUCNSA-N (2s)-2-aminobutan-1-ol Chemical compound CC[C@H](N)CO JCBPETKZIGVZRE-BYPYZUCNSA-N 0.000 description 2
- SFWWGMKXCYLZEG-YFKPBYRVSA-N (3s)-3-methylmorpholine Chemical compound C[C@H]1COCCN1 SFWWGMKXCYLZEG-YFKPBYRVSA-N 0.000 description 2
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 description 2
- FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 description 2
- WFLOTYSKFUPZQB-OWOJBTEDSA-N (e)-1,2-difluoroethene Chemical group F\C=C\F WFLOTYSKFUPZQB-OWOJBTEDSA-N 0.000 description 2
- WIKBZUXHNPONPP-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoro-2-iodo-2-(trifluoromethyl)propane Chemical compound FC(F)(F)C(I)(C(F)(F)F)C(F)(F)F WIKBZUXHNPONPP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ZNGWEEUXTBNKFR-UHFFFAOYSA-N 1,4-oxazepane Chemical compound C1CNCCOC1 ZNGWEEUXTBNKFR-UHFFFAOYSA-N 0.000 description 2
- VBPBCGSGAPPTPA-ZDUSSCGKSA-N 1-(2,2-difluoroethyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCC(F)F)=CC=2)=NC2=C1CCNC2 VBPBCGSGAPPTPA-ZDUSSCGKSA-N 0.000 description 2
- CEVRCQNMOPZXKE-HNNXBMFYSA-N 1-(2,2-difluoroethyl)-3-[4-[7-(2-hydroxy-2-methylpropanoyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCC(F)F)=CC=2)=NC2=C1CCN(C(=O)C(C)(C)O)C2 CEVRCQNMOPZXKE-HNNXBMFYSA-N 0.000 description 2
- VFZPPZAFYQFCKE-INIZCTEOSA-N 1-(2-fluoroethyl)-3-[4-[7-(2-hydroxy-2-methylpropanoyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCCF)=CC=2)=NC2=C1CCN(C(=O)C(C)(C)O)C2 VFZPPZAFYQFCKE-INIZCTEOSA-N 0.000 description 2
- LHROKGBCNPPPKC-HYVJGQCMSA-N 1-[(1s,2s)-2-hydroxycyclopentyl]-3-[4-[7-(2-hydroxy-2-methylpropanoyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)N[C@@H]3[C@H](CCC3)O)=CC=2)=NC2=C1CCN(C(=O)C(C)(C)O)C2 LHROKGBCNPPPKC-HYVJGQCMSA-N 0.000 description 2
- LNDFOZVERUIHGC-UHFFFAOYSA-N 1-[4-(6-benzoyl-4-morpholin-4-yl-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-yl)phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(C(=O)C=1C=CC=CC=1)C2 LNDFOZVERUIHGC-UHFFFAOYSA-N 0.000 description 2
- BKNRFDFUYGYHBC-QGZVFWFLSA-N 1-ethyl-3-[4-[(8r)-7-(2-methoxyethyl)-8-methyl-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(CCOC)[C@@H]2C BKNRFDFUYGYHBC-QGZVFWFLSA-N 0.000 description 2
- OIFWDRIVSDYJQR-YMXDCFFPSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(1-methylsulfonylpyrrolidin-3-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C1CN(CC1)S(C)(=O)=O)C2 OIFWDRIVSDYJQR-YMXDCFFPSA-N 0.000 description 2
- LHEPAXILFKRBLV-KRWDZBQOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(2-methylpyrazole-3-carbonyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)C=1N(N=CC=1)C)C2 LHEPAXILFKRBLV-KRWDZBQOSA-N 0.000 description 2
- QYPFJAUZMLMAAX-YMXDCFFPSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(oxan-3-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C1COCCC1)C2 QYPFJAUZMLMAAX-YMXDCFFPSA-N 0.000 description 2
- JURMWUPFFLRNEV-SFHVURJKSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(oxan-4-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C1CCOCC1)C2 JURMWUPFFLRNEV-SFHVURJKSA-N 0.000 description 2
- RPBUVQMKWYMUKC-PXNSSMCTSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-[(3s)-oxolan-3-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN([C@@H]1COCC1)C2 RPBUVQMKWYMUKC-PXNSSMCTSA-N 0.000 description 2
- MEGMZCCXHIOTCS-UHFFFAOYSA-N 1-ethyl-3-[4-[4-morpholin-4-yl-7-(4-phenylpyrimidin-2-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=C(C=CN=1)C=1C=CC=CC=1)C2 MEGMZCCXHIOTCS-UHFFFAOYSA-N 0.000 description 2
- RIOFOOHYBIOSSF-INIZCTEOSA-N 1-ethyl-3-[4-[6-ethyl-7,7-dimethyl-4-[(3s)-3-methylmorpholin-4-yl]-5h-pyrrolo[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CN(CC)C2(C)C RIOFOOHYBIOSSF-INIZCTEOSA-N 0.000 description 2
- PDFRMPVYVIBRIV-JKSUJKDBSA-N 1-ethyl-3-[4-[7-[(2r)-2-hydroxypropanoyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)[C@@H](C)O)C2 PDFRMPVYVIBRIV-JKSUJKDBSA-N 0.000 description 2
- DGHHQBMTXTWTJV-BQAIUKQQSA-N 119413-54-6 Chemical compound Cl.C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 DGHHQBMTXTWTJV-BQAIUKQQSA-N 0.000 description 2
- WXOHBCNBPCOIOG-UHFFFAOYSA-N 2,4-dichloro-6,8-dihydro-5H-pyrido[3,4-d]pyrimidine-7-carboxylic acid Chemical compound N1=C(Cl)N=C2CN(C(=O)O)CCC2=C1Cl WXOHBCNBPCOIOG-UHFFFAOYSA-N 0.000 description 2
- BRSJCUDFXDVXFP-UHFFFAOYSA-N 2-(4-aminophenyl)-6-benzyl-4-morpholin-4-yl-5h-pyrrolo[3,4-d]pyrimidin-7-one Chemical compound C1=CC(N)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(CC=1C=CC=CC=1)C2=O BRSJCUDFXDVXFP-UHFFFAOYSA-N 0.000 description 2
- HFYVDMVSSBYEHQ-UHFFFAOYSA-N 2-[2-[4-(ethylcarbamoylamino)phenyl]-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-4-(trifluoromethyl)pyrimidine-5-carboxylic acid Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=C(C(C(O)=O)=CN=1)C(F)(F)F)C2 HFYVDMVSSBYEHQ-UHFFFAOYSA-N 0.000 description 2
- PTXVOKDWCIPJHW-UHFFFAOYSA-N 2-amino-6-benzyl-1,5-dihydropyrrolo[3,4-d]pyrimidine-4,7-dione Chemical compound O=C1C=2NC(N)=NC(=O)C=2CN1CC1=CC=CC=C1 PTXVOKDWCIPJHW-UHFFFAOYSA-N 0.000 description 2
- GVWOWAUGVAZPLG-UHFFFAOYSA-N 2-chloro-6-[(4-methoxyphenyl)methyl]-4-morpholin-4-yl-5h-pyrrolo[3,4-d]pyrimidin-7-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)C(N=C(Cl)N=C2N3CCOCC3)=C2C1 GVWOWAUGVAZPLG-UHFFFAOYSA-N 0.000 description 2
- IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 2
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 2
- SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 description 2
- 125000006291 3-hydroxybenzyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(=C1[H])C([H])([H])* 0.000 description 2
- ROADCYAOHVSOLQ-UHFFFAOYSA-N 3-oxetanone Chemical compound O=C1COC1 ROADCYAOHVSOLQ-UHFFFAOYSA-N 0.000 description 2
- LZPWAYBEOJRFAX-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2$l^{2}-dioxaborolane Chemical compound CC1(C)O[B]OC1(C)C LZPWAYBEOJRFAX-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 description 2
- AXXCVYSHHQEWSA-UHFFFAOYSA-N 6-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)anilino]-1h-pyridin-2-one Chemical compound N1C(=O)C=CC=C1NC1=CC=C(C=2N=C(C=3CCN(CC=3N=2)C=2N=CC=CN=2)N2CCOCC2)C=C1 AXXCVYSHHQEWSA-UHFFFAOYSA-N 0.000 description 2
- IATJAQLBZDRMHN-SFHVURJKSA-N 6-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(pyridine-3-carbonyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]anilino]-1h-pyrazin-2-one Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC=3NC(=O)C=NC=3)=CC=2)=NC2=C1CCN(C(=O)C=1C=NC=CC=1)C2 IATJAQLBZDRMHN-SFHVURJKSA-N 0.000 description 2
- OBGIDNKTNOONGX-KRWDZBQOSA-N 6-[4-[7-ethyl-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]anilino]-1h-pyridin-2-one Chemical compound C1N(CC)CCC2=C1N=C(C=1C=CC(NC=3NC(=O)C=CC=3)=CC=1)N=C2N1CCOC[C@@H]1C OBGIDNKTNOONGX-KRWDZBQOSA-N 0.000 description 2
- STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 2
- LSBDFXRDZJMBSC-UHFFFAOYSA-N Amide-Phenylacetic acid Natural products NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 2
- 239000004475 Arginine Substances 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- 201000001320 Atherosclerosis Diseases 0.000 description 2
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 description 2
- 108010006654 Bleomycin Proteins 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 2
- DGJMHKMYSDYOFP-MRXNPFEDSA-N C=CC(N(CCC1)C[C@@H]1N1N=C(C2=CN(CC(C3=CC=CC=C3)(F)F)N=N2)C2=C(N)N=CN=C12)=O Chemical compound C=CC(N(CCC1)C[C@@H]1N1N=C(C2=CN(CC(C3=CC=CC=C3)(F)F)N=N2)C2=C(N)N=CN=C12)=O DGJMHKMYSDYOFP-MRXNPFEDSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- 241000282693 Cercopithecidae Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 description 2
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- ZBNZXTGUTAYRHI-UHFFFAOYSA-N Dasatinib Chemical compound C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1Cl ZBNZXTGUTAYRHI-UHFFFAOYSA-N 0.000 description 2
- WEAHRLBPCANXCN-UHFFFAOYSA-N Daunomycin Natural products CCC1(O)CC(OC2CC(N)C(O)C(C)O2)c3cc4C(=O)c5c(OC)cccc5C(=O)c4c(O)c3C1 WEAHRLBPCANXCN-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 108010017213 Granulocyte-Macrophage Colony-Stimulating Factor Proteins 0.000 description 2
- 102100039620 Granulocyte-macrophage colony-stimulating factor Human genes 0.000 description 2
- 102000009465 Growth Factor Receptors Human genes 0.000 description 2
- 108010009202 Growth Factor Receptors Proteins 0.000 description 2
- 108090000100 Hepatocyte Growth Factor Proteins 0.000 description 2
- 102100021866 Hepatocyte growth factor Human genes 0.000 description 2
- 208000017604 Hodgkin disease Diseases 0.000 description 2
- 208000010747 Hodgkins lymphoma Diseases 0.000 description 2
- 101001059454 Homo sapiens Serine/threonine-protein kinase MARK2 Proteins 0.000 description 2
- 101000623857 Homo sapiens Serine/threonine-protein kinase mTOR Proteins 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 description 2
- 206010021143 Hypoxia Diseases 0.000 description 2
- XDXDZDZNSLXDNA-TZNDIEGXSA-N Idarubicin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XDXDZDZNSLXDNA-TZNDIEGXSA-N 0.000 description 2
- XDXDZDZNSLXDNA-UHFFFAOYSA-N Idarubicin Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XDXDZDZNSLXDNA-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 2
- 239000005551 L01XE03 - Erlotinib Substances 0.000 description 2
- 102000046985 LST8 Homolog mTOR Associated Human genes 0.000 description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical group CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 2
- CZAFIFBJBFDMTP-UHFFFAOYSA-N N-[(4-bromophenyl)methyl]-2-[4-(2-phenylethylsulfamoyl)phenoxy]acetamide Chemical compound Brc1ccc(CNC(=O)COc2ccc(cc2)S(=O)(=O)NCCc2ccccc2)cc1 CZAFIFBJBFDMTP-UHFFFAOYSA-N 0.000 description 2
- 208000012902 Nervous system disease Diseases 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 229930012538 Paclitaxel Natural products 0.000 description 2
- 241001494479 Pecora Species 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 102100028904 Serine/threonine-protein kinase MARK2 Human genes 0.000 description 2
- 102100023085 Serine/threonine-protein kinase mTOR Human genes 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 101710115678 Target of rapamycin complex subunit LST8 Proteins 0.000 description 2
- FOCVUCIESVLUNU-UHFFFAOYSA-N Thiotepa Chemical compound C1CN1P(N1CC1)(=S)N1CC1 FOCVUCIESVLUNU-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 229920001615 Tragacanth Polymers 0.000 description 2
- 229940122803 Vinca alkaloid Drugs 0.000 description 2
- BEXZJJQVPWJPOA-VOTSOKGWSA-N [(e)-hept-2-enyl] 6-methyl-4-(4-nitrophenyl)-2-oxo-3,4-dihydro-1h-pyrimidine-5-carboxylate Chemical compound CCCC\C=C\COC(=O)C1=C(C)NC(=O)NC1C1=CC=C([N+]([O-])=O)C=C1 BEXZJJQVPWJPOA-VOTSOKGWSA-N 0.000 description 2
- 230000001594 aberrant effect Effects 0.000 description 2
- 230000002159 abnormal effect Effects 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 150000001266 acyl halides Chemical class 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 238000012382 advanced drug delivery Methods 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 125000000266 alpha-aminoacyl group Chemical group 0.000 description 2
- 229960000473 altretamine Drugs 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 2
- 239000005557 antagonist Substances 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 230000002280 anti-androgenic effect Effects 0.000 description 2
- 229940046836 anti-estrogen Drugs 0.000 description 2
- 230000001833 anti-estrogenic effect Effects 0.000 description 2
- 230000000692 anti-sense effect Effects 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 239000000051 antiandrogen Substances 0.000 description 2
- 229940030495 antiandrogen sex hormone and modulator of the genital system Drugs 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 239000003080 antimitotic agent Substances 0.000 description 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- QLKPEKQVMUDJRM-UHFFFAOYSA-N benzyl 2-[4-(ethylcarbamoylamino)phenyl]-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)OCC=1C=CC=CC=1)C2 QLKPEKQVMUDJRM-UHFFFAOYSA-N 0.000 description 2
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 229960001561 bleomycin Drugs 0.000 description 2
- OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 235000019437 butane-1,3-diol Nutrition 0.000 description 2
- 210000004899 c-terminal region Anatomy 0.000 description 2
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229940127093 camptothecin Drugs 0.000 description 2
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 description 2
- OMZCMEYTWSXEPZ-UHFFFAOYSA-N canertinib Chemical compound C1=C(Cl)C(F)=CC=C1NC1=NC=NC2=CC(OCCCN3CCOCC3)=C(NC(=O)C=C)C=C12 OMZCMEYTWSXEPZ-UHFFFAOYSA-N 0.000 description 2
- 125000001589 carboacyl group Chemical group 0.000 description 2
- YAYRGNWWLMLWJE-UHFFFAOYSA-L carboplatin Chemical group O=C1O[Pt](N)(N)OC(=O)C11CCC1 YAYRGNWWLMLWJE-UHFFFAOYSA-L 0.000 description 2
- 229960004562 carboplatin Drugs 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 229960004630 chlorambucil Drugs 0.000 description 2
- JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical group N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 2
- 229960004316 cisplatin Drugs 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229960004397 cyclophosphamide Drugs 0.000 description 2
- 231100000433 cytotoxic Toxicity 0.000 description 2
- 230000001472 cytotoxic effect Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- LTVOKYUPTHZZQH-UHFFFAOYSA-N difluoromethane Chemical group F[C]F LTVOKYUPTHZZQH-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- SLIKWVTWIGHFJE-UHFFFAOYSA-N diphenoxymethylidenecyanamide Chemical compound C=1C=CC=CC=1OC(=NC#N)OC1=CC=CC=C1 SLIKWVTWIGHFJE-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 description 2
- 238000012377 drug delivery Methods 0.000 description 2
- 201000003914 endometrial carcinoma Diseases 0.000 description 2
- 229960001433 erlotinib Drugs 0.000 description 2
- 239000000328 estrogen antagonist Substances 0.000 description 2
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 2
- VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 description 2
- 229960005420 etoposide Drugs 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- GIUYCYHIANZCFB-FJFJXFQQSA-N fludarabine phosphate Chemical compound C1=NC=2C(N)=NC(F)=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O GIUYCYHIANZCFB-FJFJXFQQSA-N 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229960002949 fluorouracil Drugs 0.000 description 2
- 229960002074 flutamide Drugs 0.000 description 2
- MKXKFYHWDHIYRV-UHFFFAOYSA-N flutamide Chemical compound CC(C)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 MKXKFYHWDHIYRV-UHFFFAOYSA-N 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 2
- XGALLCVXEZPNRQ-UHFFFAOYSA-N gefitinib Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 XGALLCVXEZPNRQ-UHFFFAOYSA-N 0.000 description 2
- SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 description 2
- 229960005277 gemcitabine Drugs 0.000 description 2
- 238000001415 gene therapy Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 229940075507 glyceryl monostearate Drugs 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- 231100000844 hepatocellular carcinoma Toxicity 0.000 description 2
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 2
- 229940088597 hormone Drugs 0.000 description 2
- 239000005556 hormone Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- VIPHVHVAGBKHGR-UHFFFAOYSA-N hydron;pyridine-2-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=CC=N1 VIPHVHVAGBKHGR-UHFFFAOYSA-N 0.000 description 2
- 229960001330 hydroxycarbamide Drugs 0.000 description 2
- 230000007954 hypoxia Effects 0.000 description 2
- 229960000908 idarubicin Drugs 0.000 description 2
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 208000027866 inflammatory disease Diseases 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 210000002510 keratinocyte Anatomy 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- RGLRXNKKBLIBQS-XNHQSDQCSA-N leuprolide acetate Chemical compound CC(O)=O.CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)CC1=CC=C(O)C=C1 RGLRXNKKBLIBQS-XNHQSDQCSA-N 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 208000014018 liver neoplasm Diseases 0.000 description 2
- 239000007937 lozenge Substances 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 229940124302 mTOR inhibitor Drugs 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- RQZAXGRLVPAYTJ-GQFGMJRRSA-N megestrol acetate Chemical compound C1=C(C)C2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 RQZAXGRLVPAYTJ-GQFGMJRRSA-N 0.000 description 2
- 229960004296 megestrol acetate Drugs 0.000 description 2
- SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 description 2
- 229960001924 melphalan Drugs 0.000 description 2
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229960000485 methotrexate Drugs 0.000 description 2
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 2
- 239000004005 microsphere Substances 0.000 description 2
- 229960004857 mitomycin Drugs 0.000 description 2
- 229960001156 mitoxantrone Drugs 0.000 description 2
- KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical class CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- OSTGTTZJOCZWJG-UHFFFAOYSA-N nitrosourea Chemical compound NC(=O)N=NO OSTGTTZJOCZWJG-UHFFFAOYSA-N 0.000 description 2
- 239000000346 nonvolatile oil Substances 0.000 description 2
- 235000014593 oils and fats Nutrition 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000002018 overexpression Effects 0.000 description 2
- 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 229960001592 paclitaxel Drugs 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 230000001575 pathological effect Effects 0.000 description 2
- AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- BZQFBWGGLXLEPQ-REOHCLBHSA-N phosphoserine Chemical compound OC(=O)[C@@H](N)COP(O)(O)=O BZQFBWGGLXLEPQ-REOHCLBHSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- XOKSLPVRUOBDEW-UHFFFAOYSA-N pinane Chemical compound CC1CCC2C(C)(C)C1C2 XOKSLPVRUOBDEW-UHFFFAOYSA-N 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920001184 polypeptide Polymers 0.000 description 2
- 229920000136 polysorbate Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 102000004196 processed proteins & peptides Human genes 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 239000000583 progesterone congener Substances 0.000 description 2
- IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 2
- 150000003235 pyrrolidines Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000008521 reorganization Effects 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 208000037803 restenosis Diseases 0.000 description 2
- OUKYUETWWIPKQR-UHFFFAOYSA-N saracatinib Chemical compound C1CN(C)CCN1CCOC1=CC(OC2CCOCC2)=C(C(NC=2C(=CC=C3OCOC3=2)Cl)=NC=N2)C2=C1 OUKYUETWWIPKQR-UHFFFAOYSA-N 0.000 description 2
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 210000003491 skin Anatomy 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 235000010356 sorbitol Nutrition 0.000 description 2
- 206010041823 squamous cell carcinoma Diseases 0.000 description 2
- 208000017572 squamous cell neoplasm Diseases 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 238000004808 supercritical fluid chromatography Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- 229960001603 tamoxifen Drugs 0.000 description 2
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 2
- 229940063683 taxotere Drugs 0.000 description 2
- NRUKOCRGYNPUPR-QBPJDGROSA-N teniposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@@H](OC[C@H]4O3)C=3SC=CC=3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NRUKOCRGYNPUPR-QBPJDGROSA-N 0.000 description 2
- 229960001278 teniposide Drugs 0.000 description 2
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
- SMPCLQCICDGOCB-CVDCTZTESA-N tert-butyl (8s)-2-[4-(ethylcarbamoylamino)phenyl]-4-[(3s)-3-methylmorpholin-4-yl]-8-prop-2-enyl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)OC(C)(C)C)[C@H]2CC=C SMPCLQCICDGOCB-CVDCTZTESA-N 0.000 description 2
- RRKRYAGIWXSHBP-NRFANRHFSA-N tert-butyl (8s)-2-[4-(ethylcarbamoylamino)phenyl]-8-(2-hydroxyethyl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)OC(C)(C)C)[C@H]2CCO RRKRYAGIWXSHBP-NRFANRHFSA-N 0.000 description 2
- NMQIRQVAMAGJLZ-UHFFFAOYSA-N tert-butyl 4-morpholin-4-yl-2-[4-[[3-(trifluoromethyl)phenyl]carbamoylamino]phenyl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC2=C1N=C(C=1C=CC(NC(=O)NC=3C=C(C=CC=3)C(F)(F)F)=CC=1)N=C2N1CCOCC1 NMQIRQVAMAGJLZ-UHFFFAOYSA-N 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 2
- 125000005309 thioalkoxy group Chemical group 0.000 description 2
- WYWHKKSPHMUBEB-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 description 2
- 238000011200 topical administration Methods 0.000 description 2
- 229960000303 topotecan Drugs 0.000 description 2
- 230000014616 translation Effects 0.000 description 2
- IUCJMVBFZDHPDX-UHFFFAOYSA-N tretamine Chemical compound C1CN1C1=NC(N2CC2)=NC(N2CC2)=N1 IUCJMVBFZDHPDX-UHFFFAOYSA-N 0.000 description 2
- 229950001353 tretamine Drugs 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 210000004881 tumor cell Anatomy 0.000 description 2
- 238000011144 upstream manufacturing Methods 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- 229960003048 vinblastine Drugs 0.000 description 2
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 2
- 229960004528 vincristine Drugs 0.000 description 2
- GBABOYUKABKIAF-GHYRFKGUSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-GHYRFKGUSA-N 0.000 description 2
- 229960002066 vinorelbine Drugs 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 1
- OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 description 1
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- YOVVNQKCSKSHKT-HNNXBMFYSA-N (2s)-1-[4-[[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one Chemical compound C1CN(C(=O)[C@@H](O)C)CCN1CC1=C(C)C2=NC(C=3C=NC(N)=NC=3)=NC(N3CCOCC3)=C2S1 YOVVNQKCSKSHKT-HNNXBMFYSA-N 0.000 description 1
- XMQUEQJCYRFIQS-YFKPBYRVSA-N (2s)-2-amino-5-ethoxy-5-oxopentanoic acid Chemical compound CCOC(=O)CC[C@H](N)C(O)=O XMQUEQJCYRFIQS-YFKPBYRVSA-N 0.000 description 1
- MHFUWOIXNMZFIW-WNQIDUERSA-N (2s)-2-hydroxypropanoic acid;n-[4-[4-(4-methylpiperazin-1-yl)-6-[(5-methyl-1h-pyrazol-3-yl)amino]pyrimidin-2-yl]sulfanylphenyl]cyclopropanecarboxamide Chemical compound C[C@H](O)C(O)=O.C1CN(C)CCN1C1=CC(NC2=NNC(C)=C2)=NC(SC=2C=CC(NC(=O)C3CC3)=CC=2)=N1 MHFUWOIXNMZFIW-WNQIDUERSA-N 0.000 description 1
- JOZZAIIGWFLONA-YFKPBYRVSA-N (2s)-3-methylbutan-2-amine Chemical compound CC(C)[C@H](C)N JOZZAIIGWFLONA-YFKPBYRVSA-N 0.000 description 1
- CVCLJVVBHYOXDC-IAZSKANUSA-N (2z)-2-[(5z)-5-[(3,5-dimethyl-1h-pyrrol-2-yl)methylidene]-4-methoxypyrrol-2-ylidene]indole Chemical compound COC1=C\C(=C/2N=C3C=CC=CC3=C\2)N\C1=C/C=1NC(C)=CC=1C CVCLJVVBHYOXDC-IAZSKANUSA-N 0.000 description 1
- IBTSWKLSEOGJGJ-UHFFFAOYSA-N (3-acetamidophenyl)boronic acid Chemical compound CC(=O)NC1=CC=CC(B(O)O)=C1 IBTSWKLSEOGJGJ-UHFFFAOYSA-N 0.000 description 1
- MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 1
- VFNQMIZKDGLNEO-ZDUSSCGKSA-N (3s)-4-[2-(1h-indol-5-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-yl]-3-methylmorpholine Chemical compound C[C@H]1COCCN1C1=NC(C=2C=C3C=CNC3=CC=2)=NC2=C1CCNC2 VFNQMIZKDGLNEO-ZDUSSCGKSA-N 0.000 description 1
- FLKXJCZPAPSHOW-QFIPXVFZSA-N (3s)-4-[2-(1h-indol-5-yl)-7-[1-(pyridin-3-ylmethyl)piperidin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-4-yl]-3-methylmorpholine Chemical compound C[C@H]1COCCN1C1=NC(C=2C=C3C=CNC3=CC=2)=NC2=C1CCN(C1CCN(CC=3C=NC=CC=3)CC1)C2 FLKXJCZPAPSHOW-QFIPXVFZSA-N 0.000 description 1
- NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 description 1
- XTVMZKCCFLOJBL-UHFFFAOYSA-N (4-pyrazol-1-ylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1N1N=CC=C1 XTVMZKCCFLOJBL-UHFFFAOYSA-N 0.000 description 1
- YJGVMLPVUAXIQN-LGWHJFRWSA-N (5s,5ar,8ar,9r)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one Chemical compound COC1=C(OC)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O)[C@@H]3[C@@H]2C(OC3)=O)=C1 YJGVMLPVUAXIQN-LGWHJFRWSA-N 0.000 description 1
- MWWSFMDVAYGXBV-MYPASOLCSA-N (7r,9s)-7-[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione;hydrochloride Chemical compound Cl.O([C@@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 MWWSFMDVAYGXBV-MYPASOLCSA-N 0.000 description 1
- FPVKHBSQESCIEP-UHFFFAOYSA-N (8S)-3-(2-deoxy-beta-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol Natural products C1C(O)C(CO)OC1N1C(NC=NCC2O)=C2N=C1 FPVKHBSQESCIEP-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LKJPYSCBVHEWIU-KRWDZBQOSA-N (R)-bicalutamide Chemical compound C([C@@](O)(C)C(=O)NC=1C=C(C(C#N)=CC=1)C(F)(F)F)S(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-KRWDZBQOSA-N 0.000 description 1
- ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 description 1
- JNPGUXGVLNJQSQ-BGGMYYEUSA-M (e,3r,5s)-7-[4-(4-fluorophenyl)-1,2-di(propan-2-yl)pyrrol-3-yl]-3,5-dihydroxyhept-6-enoate Chemical compound CC(C)N1C(C(C)C)=C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)C(C=2C=CC(F)=CC=2)=C1 JNPGUXGVLNJQSQ-BGGMYYEUSA-M 0.000 description 1
- VAVHMEQFYYBAPR-ITWZMISCSA-N (e,3r,5s)-7-[4-(4-fluorophenyl)-1-phenyl-2-propan-2-ylpyrrol-3-yl]-3,5-dihydroxyhept-6-enoic acid Chemical compound CC(C)C1=C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)C(C=2C=CC(F)=CC=2)=CN1C1=CC=CC=C1 VAVHMEQFYYBAPR-ITWZMISCSA-N 0.000 description 1
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 1
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
- UKAUYVFTDYCKQA-UHFFFAOYSA-N -2-Amino-4-hydroxybutanoic acid Natural products OC(=O)C(N)CCO UKAUYVFTDYCKQA-UHFFFAOYSA-N 0.000 description 1
- WFCXDAQSTGDHCJ-UHFFFAOYSA-N 1,1-dimethyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea Chemical compound C1=CC(NC(=O)N(C)C)=CC=C1B1OC(C)(C)C(C)(C)O1 WFCXDAQSTGDHCJ-UHFFFAOYSA-N 0.000 description 1
- QXMBDQUTLPMXQK-UHFFFAOYSA-N 1,1-dimethyl-3-[4-(4-morpholin-4-yl-6-pyrimidin-2-yl-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-yl)phenyl]urea Chemical compound C1=CC(NC(=O)N(C)C)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(C=1N=CC=CN=1)C2 QXMBDQUTLPMXQK-UHFFFAOYSA-N 0.000 description 1
- BWKMGYQJPOAASG-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid Chemical compound C1=CC=C2CNC(C(=O)O)CC2=C1 BWKMGYQJPOAASG-UHFFFAOYSA-N 0.000 description 1
- 125000001724 1,2,3-oxadiazol-4-yl group Chemical group [H]C1=C(*)N=NO1 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- GYZPQJVSAQBAHP-UHFFFAOYSA-N 1,3,4-oxadiazole-2-carboxylic acid Chemical compound OC(=O)C1=NN=CO1 GYZPQJVSAQBAHP-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- HKZCFGQSWLWNQA-UHFFFAOYSA-N 1,3-thiazole-2-carbonyl chloride Chemical compound ClC(=O)C1=NC=CS1 HKZCFGQSWLWNQA-UHFFFAOYSA-N 0.000 description 1
- 125000000196 1,4-pentadienyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])=C([H])[H] 0.000 description 1
- YHIIJNLSGULWAA-UHFFFAOYSA-N 1,4-thiazinane 1-oxide Chemical class O=S1CCNCC1 YHIIJNLSGULWAA-UHFFFAOYSA-N 0.000 description 1
- NBTMWRZTIDGKMK-UHFFFAOYSA-N 1-(1-hydroxy-2-methylpropan-2-yl)-3-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]urea Chemical compound C1=CC(NC(=O)NC(C)(CO)C)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CC=CN=1)C2 NBTMWRZTIDGKMK-UHFFFAOYSA-N 0.000 description 1
- APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 description 1
- MPQZOHSLKBCGNU-UHFFFAOYSA-N 1-(2,2-difluoroethyl)-3-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]urea Chemical compound C1=CC(NC(=O)NCC(F)F)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CC=CN=1)C2 MPQZOHSLKBCGNU-UHFFFAOYSA-N 0.000 description 1
- QCISZMOMTHHKKA-ZDUSSCGKSA-N 1-(2,2-difluoroethyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCC(F)F)=CC=2)=NC2=C1CNCC2 QCISZMOMTHHKKA-ZDUSSCGKSA-N 0.000 description 1
- GHBNIWDIIFVOJI-HNNXBMFYSA-N 1-(2,2-difluoroethyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(1,3-thiazole-2-carbonyl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCC(F)F)=CC=2)=NC2=C1CN(C(=O)C=1SC=CN=1)CC2 GHBNIWDIIFVOJI-HNNXBMFYSA-N 0.000 description 1
- VGXOKDYAUFAIEN-INIZCTEOSA-N 1-(2,2-difluoroethyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-pyrimidin-2-yl-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCC(F)F)=CC=2)=NC2=C1CN(C=1N=CC=CN=1)CC2 VGXOKDYAUFAIEN-INIZCTEOSA-N 0.000 description 1
- VWRLXEGNNKVFPJ-KRWDZBQOSA-N 1-(2,2-difluoroethyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(pyridine-3-carbonyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCC(F)F)=CC=2)=NC2=C1CCN(C(=O)C=1C=NC=CC=1)C2 VWRLXEGNNKVFPJ-KRWDZBQOSA-N 0.000 description 1
- PUMJMGOXRUKFRK-INIZCTEOSA-N 1-(2,2-difluoroethyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCC(F)F)=CC=2)=NC2=C1CCN(C=1N=CC=CN=1)C2 PUMJMGOXRUKFRK-INIZCTEOSA-N 0.000 description 1
- ZKBKJEXEOHUBHB-UHFFFAOYSA-N 1-(2,2-dimethylpropyl)-3-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]urea Chemical compound C1=CC(NC(=O)NCC(C)(C)C)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CC=CN=1)C2 ZKBKJEXEOHUBHB-UHFFFAOYSA-N 0.000 description 1
- KCUGWFIKGOKLII-UHFFFAOYSA-N 1-(2-aminophenyl)-3-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]urea Chemical compound NC1=CC=CC=C1NC(=O)NC1=CC=C(C=2N=C(C=3CCN(CC=3N=2)C=2N=CC=CN=2)N2CCOCC2)C=C1 KCUGWFIKGOKLII-UHFFFAOYSA-N 0.000 description 1
- FYYSNYMXHZTZJQ-UHFFFAOYSA-N 1-(2-cyanoethyl)-3-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]urea Chemical compound C1=CC(NC(NCCC#N)=O)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CC=CN=1)C2 FYYSNYMXHZTZJQ-UHFFFAOYSA-N 0.000 description 1
- RXACQINPCIAJMR-IBGZPJMESA-N 1-(2-cyanoethyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(pyridine-3-carbonyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCCC#N)=CC=2)=NC2=C1CCN(C(=O)C=1C=NC=CC=1)C2 RXACQINPCIAJMR-IBGZPJMESA-N 0.000 description 1
- ITLBDKISWJRJOO-SFHVURJKSA-N 1-(2-cyanoethyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCCC#N)=CC=2)=NC2=C1CCN(C=1N=CC=CN=1)C2 ITLBDKISWJRJOO-SFHVURJKSA-N 0.000 description 1
- XQBYNFCSMVSBFR-SFHVURJKSA-N 1-(2-cyanoethyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-pyrimidin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCCC#N)=CC=2)=NC2=C1CCN(C=1N=CN=CC=1)C2 XQBYNFCSMVSBFR-SFHVURJKSA-N 0.000 description 1
- YHIZMVWXSFIBPW-UHFFFAOYSA-N 1-(2-fluoroethyl)-3-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]urea Chemical compound C1=CC(NC(=O)NCCF)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CC=CN=1)C2 YHIZMVWXSFIBPW-UHFFFAOYSA-N 0.000 description 1
- YNJQZSZLZAYEFO-SFHVURJKSA-N 1-(2-fluoroethyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(pyridine-3-carbonyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCCF)=CC=2)=NC2=C1CCN(C(=O)C=1C=NC=CC=1)C2 YNJQZSZLZAYEFO-SFHVURJKSA-N 0.000 description 1
- FCMZDNQBKYQWEW-KRWDZBQOSA-N 1-(2-fluoroethyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-pyrazin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCCF)=CC=2)=NC2=C1CCN(C=1N=CC=NC=1)C2 FCMZDNQBKYQWEW-KRWDZBQOSA-N 0.000 description 1
- ANIHEBKKDCTZJP-KRWDZBQOSA-N 1-(2-fluoroethyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCCF)=CC=2)=NC2=C1CCN(C=1N=CC=CN=1)C2 ANIHEBKKDCTZJP-KRWDZBQOSA-N 0.000 description 1
- SYCDSFNZKJRMOZ-UHFFFAOYSA-N 1-(2-hydroxyethyl)-3-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]urea Chemical compound C1=CC(NC(=O)NCCO)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CC=CN=1)C2 SYCDSFNZKJRMOZ-UHFFFAOYSA-N 0.000 description 1
- YTGLZNMNOOOPMI-KRWDZBQOSA-N 1-(2-hydroxyethyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-pyrimidin-2-yl-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCCO)=CC=2)=NC2=C1CN(C=1N=CC=CN=1)CC2 YTGLZNMNOOOPMI-KRWDZBQOSA-N 0.000 description 1
- XYMLSUJHHJMDKZ-INIZCTEOSA-N 1-(2-hydroxyethyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-propanoyl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1N(C(=O)CC)CCC2=C1N=C(C=1C=CC(NC(=O)NCCO)=CC=1)N=C2N1CCOC[C@@H]1C XYMLSUJHHJMDKZ-INIZCTEOSA-N 0.000 description 1
- QGAPAOPKYCHXPR-KRWDZBQOSA-N 1-(2-hydroxyethyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCCO)=CC=2)=NC2=C1CCN(C=1N=CC=CN=1)C2 QGAPAOPKYCHXPR-KRWDZBQOSA-N 0.000 description 1
- QJCYIKLTACBTOI-KRWDZBQOSA-N 1-(2-hydroxyethyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-pyrimidin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCCO)=CC=2)=NC2=C1CCN(C=1N=CN=CC=1)C2 QJCYIKLTACBTOI-KRWDZBQOSA-N 0.000 description 1
- YFKFDHJCLNOPHG-INIZCTEOSA-N 1-(2-hydroxyethyl)-3-[4-[6-(2-hydroxy-2-methylpropanoyl)-4-[(3s)-3-methylmorpholin-4-yl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCCO)=CC=2)=NC2=C1CN(C(=O)C(C)(C)O)CC2 YFKFDHJCLNOPHG-INIZCTEOSA-N 0.000 description 1
- PVTVNOMBDVXYOJ-UHFFFAOYSA-N 1-(2-methoxyethyl)-3-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]urea Chemical compound C1=CC(NC(=O)NCCOC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CC=CN=1)C2 PVTVNOMBDVXYOJ-UHFFFAOYSA-N 0.000 description 1
- WVWOOAYQYLJEFD-UHFFFAOYSA-N 1-(2-nitroimidazol-1-yl)-3-piperidin-1-ylpropan-2-ol Chemical compound C1=CN=C([N+]([O-])=O)N1CC(O)CN1CCCCC1 WVWOOAYQYLJEFD-UHFFFAOYSA-N 0.000 description 1
- NKIRICAZARXQFR-KRWDZBQOSA-N 1-(3,4-difluorophenyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(oxetan-3-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC=3C=C(F)C(F)=CC=3)=CC=2)=NC2=C1CCN(C1COC1)C2 NKIRICAZARXQFR-KRWDZBQOSA-N 0.000 description 1
- SFJPRHDINFGUJD-KRWDZBQOSA-N 1-(3-fluoropropyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(oxetan-3-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCCCF)=CC=2)=NC2=C1CCN(C1COC1)C2 SFJPRHDINFGUJD-KRWDZBQOSA-N 0.000 description 1
- FTMSBUVEUGLIOE-UHFFFAOYSA-N 1-(3-hydroxycyclobutyl)-3-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]urea Chemical compound C1C(O)CC1NC(=O)NC1=CC=C(C=2N=C(C=3CCN(CC=3N=2)C=2N=CC=CN=2)N2CCOCC2)C=C1 FTMSBUVEUGLIOE-UHFFFAOYSA-N 0.000 description 1
- OEWYWFJWBZNJJG-UHFFFAOYSA-N 1-(aziridin-1-yl)-3-(2-nitroimidazol-1-yl)propan-2-ol Chemical compound C1=CN=C([N+]([O-])=O)N1CC(O)CN1CC1 OEWYWFJWBZNJJG-UHFFFAOYSA-N 0.000 description 1
- XHRVWACQISDKQA-UHFFFAOYSA-N 1-(cyclopropylmethyl)-3-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]urea Chemical compound C=1C=C(C=2N=C(C=3CCN(CC=3N=2)C=2N=CC=CN=2)N2CCOCC2)C=CC=1NC(=O)NCC1CC1 XHRVWACQISDKQA-UHFFFAOYSA-N 0.000 description 1
- ZBFJCCWGYJLMTQ-JTHBVZDNSA-N 1-[(1s,2r)-2-hydroxycyclopentyl]-3-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]urea Chemical compound O[C@@H]1CCC[C@@H]1NC(=O)NC1=CC=C(C=2N=C(C=3CCN(CC=3N=2)C=2N=CC=CN=2)N2CCOCC2)C=C1 ZBFJCCWGYJLMTQ-JTHBVZDNSA-N 0.000 description 1
- ZBFJCCWGYJLMTQ-GMAHTHKFSA-N 1-[(1s,2s)-2-hydroxycyclopentyl]-3-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]urea Chemical compound O[C@H]1CCC[C@@H]1NC(=O)NC1=CC=C(C=2N=C(C=3CCN(CC=3N=2)C=2N=CC=CN=2)N2CCOCC2)C=C1 ZBFJCCWGYJLMTQ-GMAHTHKFSA-N 0.000 description 1
- OAVHRSUQGOGYPM-YLORPAJWSA-N 1-[(1s,2s)-2-hydroxycyclopentyl]-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(pyridine-3-carbonyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)N[C@@H]3[C@H](CCC3)O)=CC=2)=NC2=C1CCN(C(=O)C=1C=NC=CC=1)C2 OAVHRSUQGOGYPM-YLORPAJWSA-N 0.000 description 1
- ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
- VAZYXSBMRPTANI-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-3-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]urea Chemical compound C1=CC(NC(=O)NCCN(C)C)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CC=CN=1)C2 VAZYXSBMRPTANI-UHFFFAOYSA-N 0.000 description 1
- CGCKPCWUYNBZDV-UHFFFAOYSA-N 1-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]-3-(1,2-oxazol-3-yl)urea Chemical compound C=1C=C(C=2N=C(C=3CCN(CC=3N=2)C=2N=CC=CN=2)N2CCOCC2)C=CC=1NC(=O)NC=1C=CON=1 CGCKPCWUYNBZDV-UHFFFAOYSA-N 0.000 description 1
- JFZGJULQMVUQOF-UHFFFAOYSA-N 1-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]-3-(2,2,2-trifluoroethyl)urea Chemical compound C1=CC(NC(=O)NCC(F)(F)F)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CC=CN=1)C2 JFZGJULQMVUQOF-UHFFFAOYSA-N 0.000 description 1
- XVWHDSFTSFFYGW-UHFFFAOYSA-N 1-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]-3-propan-2-ylurea Chemical compound C1=CC(NC(=O)NC(C)C)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CC=CN=1)C2 XVWHDSFTSFFYGW-UHFFFAOYSA-N 0.000 description 1
- HSPRUMIPFWSQAM-UHFFFAOYSA-N 1-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]-3-pyridin-4-ylurea Chemical compound C=1C=C(C=2N=C(C=3CCN(CC=3N=2)C=2N=CC=CN=2)N2CCOCC2)C=CC=1NC(=O)NC1=CC=NC=C1 HSPRUMIPFWSQAM-UHFFFAOYSA-N 0.000 description 1
- BTRKYXJLPAZSNE-UHFFFAOYSA-N 1-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]imidazol-2-amine Chemical compound NC1=NC=CN1C1=CC=C(C=2N=C(C=3CCN(CC=3N=2)C=2N=CC=CN=2)N2CCOCC2)C=C1 BTRKYXJLPAZSNE-UHFFFAOYSA-N 0.000 description 1
- SXELBLWCVJLVKJ-UHFFFAOYSA-N 1-[4-(4-morpholin-4-ylspiro[6,8-dihydro-5h-pyrido[4,3-d]pyrimidine-7,3'-oxetane]-2-yl)phenyl]-3-(1,2-oxazol-3-yl)urea Chemical compound C=1C=C(C=2N=C(C=3CNC4(COC4)CC=3N=2)N2CCOCC2)C=CC=1NC(=O)NC=1C=CON=1 SXELBLWCVJLVKJ-UHFFFAOYSA-N 0.000 description 1
- OYMMRWQHJKLNFW-UHFFFAOYSA-N 1-[4-(6-benzyl-4-morpholin-4-yl-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-yl)phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(CC=1C=CC=CC=1)C2 OYMMRWQHJKLNFW-UHFFFAOYSA-N 0.000 description 1
- LIVVFXAPTOJZKV-UHFFFAOYSA-N 1-[4-(6-benzyl-4-morpholin-4-yl-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl)phenyl]-3-(3-methyl-2,4-dioxo-1h-pyrimidin-6-yl)urea Chemical compound N1C(=O)N(C)C(=O)C=C1NC(=O)NC1=CC=C(C=2N=C(C=3CN(CC=4C=CC=CC=4)CCC=3N=2)N2CCOCC2)C=C1 LIVVFXAPTOJZKV-UHFFFAOYSA-N 0.000 description 1
- LZHLCIJGFQAXOJ-UHFFFAOYSA-N 1-[4-(6-methyl-4-morpholin-4-ylspiro[5,8-dihydropyrido[4,3-d]pyrimidine-7,3'-oxetane]-2-yl)phenyl]-3-(1,2-oxazol-3-yl)urea Chemical compound CN1CC(C(=NC(=N2)C=3C=CC(NC(=O)NC4=NOC=C4)=CC=3)N3CCOCC3)=C2CC11COC1 LZHLCIJGFQAXOJ-UHFFFAOYSA-N 0.000 description 1
- GHJXGELKFMGHBN-UHFFFAOYSA-N 1-[4-(7-acetyl-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(C)=O)C2 GHJXGELKFMGHBN-UHFFFAOYSA-N 0.000 description 1
- ZJTUKGNZFLSUBN-UHFFFAOYSA-N 1-[4-(7-benzoyl-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)C=1C=CC=CC=1)C2 ZJTUKGNZFLSUBN-UHFFFAOYSA-N 0.000 description 1
- LYEVLIVOGLPWBF-DNVCBOLYSA-N 1-[4-[(10ar)-4-[(3r)-3-methylmorpholin-4-yl]-8-oxo-6,9,10,10a-tetrahydro-5h-pyrimido[5,4-g]indolizin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@@H](COCC2)C)=NC2=C1CCN1C(=O)CC[C@@H]12 LYEVLIVOGLPWBF-DNVCBOLYSA-N 0.000 description 1
- JAZFIYGTHVESIH-OXJNMPFZSA-N 1-[4-[(10ar)-4-[(3s)-3-methylmorpholin-4-yl]-5,6,8,9,10,10a-hexahydropyrimido[5,4-g]indolizin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN1CCC[C@@H]12 JAZFIYGTHVESIH-OXJNMPFZSA-N 0.000 description 1
- DNXZQGYZWBNYTQ-LJQANCHMSA-N 1-[4-[(10ar)-4-morpholin-4-yl-8-oxo-6,9,10,10a-tetrahydro-5h-pyrimido[5,4-g]indolizin-2-yl]phenyl]-3-(oxetan-3-yl)urea Chemical compound C=1C=C(C=2N=C(C=3CCN4C(=O)CC[C@@H]4C=3N=2)N2CCOCC2)C=CC=1NC(=O)NC1COC1 DNXZQGYZWBNYTQ-LJQANCHMSA-N 0.000 description 1
- QAVIPXJUBNODKR-LJQANCHMSA-N 1-[4-[(10ar)-4-morpholin-4-yl-8-oxo-6,9,10,10a-tetrahydro-5h-pyrimido[5,4-g]indolizin-2-yl]phenyl]-3-propylurea Chemical compound C1=CC(NC(=O)NCCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN1C(=O)CC[C@@H]12 QAVIPXJUBNODKR-LJQANCHMSA-N 0.000 description 1
- LYEVLIVOGLPWBF-BEFAXECRSA-N 1-[4-[(10as)-4-[(3r)-3-methylmorpholin-4-yl]-8-oxo-6,9,10,10a-tetrahydro-5h-pyrimido[5,4-g]indolizin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@@H](COCC2)C)=NC2=C1CCN1C(=O)CC[C@H]12 LYEVLIVOGLPWBF-BEFAXECRSA-N 0.000 description 1
- JAZFIYGTHVESIH-JXFKEZNVSA-N 1-[4-[(10as)-4-[(3s)-3-methylmorpholin-4-yl]-5,6,8,9,10,10a-hexahydropyrimido[5,4-g]indolizin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN1CCC[C@H]12 JAZFIYGTHVESIH-JXFKEZNVSA-N 0.000 description 1
- LYEVLIVOGLPWBF-KXBFYZLASA-N 1-[4-[(10as)-4-[(3s)-3-methylmorpholin-4-yl]-8-oxo-6,9,10,10a-tetrahydro-5h-pyrimido[5,4-g]indolizin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN1C(=O)CC[C@H]12 LYEVLIVOGLPWBF-KXBFYZLASA-N 0.000 description 1
- DNXZQGYZWBNYTQ-IBGZPJMESA-N 1-[4-[(10as)-4-morpholin-4-yl-8-oxo-6,9,10,10a-tetrahydro-5h-pyrimido[5,4-g]indolizin-2-yl]phenyl]-3-(oxetan-3-yl)urea Chemical compound C=1C=C(C=2N=C(C=3CCN4C(=O)CC[C@H]4C=3N=2)N2CCOCC2)C=CC=1NC(=O)NC1COC1 DNXZQGYZWBNYTQ-IBGZPJMESA-N 0.000 description 1
- QAVIPXJUBNODKR-IBGZPJMESA-N 1-[4-[(10as)-4-morpholin-4-yl-8-oxo-6,9,10,10a-tetrahydro-5h-pyrimido[5,4-g]indolizin-2-yl]phenyl]-3-propylurea Chemical compound C1=CC(NC(=O)NCCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN1C(=O)CC[C@H]12 QAVIPXJUBNODKR-IBGZPJMESA-N 0.000 description 1
- SMSNQOSKOOIZNC-LJQANCHMSA-N 1-[4-[(11ar)-4-morpholin-4-yl-8-oxo-5,6,9,10,11,11a-hexahydropyrimido[4,5-a]quinolizin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN1C(=O)CCC[C@@H]12 SMSNQOSKOOIZNC-LJQANCHMSA-N 0.000 description 1
- SMSNQOSKOOIZNC-IBGZPJMESA-N 1-[4-[(11as)-4-morpholin-4-yl-8-oxo-5,6,9,10,11,11a-hexahydropyrimido[4,5-a]quinolizin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN1C(=O)CCC[C@H]12 SMSNQOSKOOIZNC-IBGZPJMESA-N 0.000 description 1
- QKNNTEULXASEAX-JKSUJKDBSA-N 1-[4-[(8r)-7,8-dimethyl-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C)[C@@H]2C QKNNTEULXASEAX-JKSUJKDBSA-N 0.000 description 1
- LRYYEBRUXZSCDP-GOSISDBHSA-N 1-[4-[(8r)-7-(2,6-dimethylpyrimidin-4-yl)-8-methyl-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=C(C)N=C(C)C=1)[C@@H]2C LRYYEBRUXZSCDP-GOSISDBHSA-N 0.000 description 1
- XBKIIRCCNCSABV-GOSISDBHSA-N 1-[4-[(8r)-7-(5-cyanopyridin-2-yl)-8-methyl-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CC(=CC=1)C#N)[C@@H]2C XBKIIRCCNCSABV-GOSISDBHSA-N 0.000 description 1
- QKNNTEULXASEAX-HOTGVXAUSA-N 1-[4-[(8s)-7,8-dimethyl-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C)[C@H]2C QKNNTEULXASEAX-HOTGVXAUSA-N 0.000 description 1
- LRYYEBRUXZSCDP-SFHVURJKSA-N 1-[4-[(8s)-7-(2,6-dimethylpyrimidin-4-yl)-8-methyl-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=C(C)N=C(C)C=1)[C@H]2C LRYYEBRUXZSCDP-SFHVURJKSA-N 0.000 description 1
- LPMHDUQGEFMAGB-HOTGVXAUSA-N 1-[4-[(8s)-7-acetyl-8-methyl-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(C)=O)[C@H]2C LPMHDUQGEFMAGB-HOTGVXAUSA-N 0.000 description 1
- KAOQIYYLGAOMIG-UWJYYQICSA-N 1-[4-[(8s)-8-(cyanomethyl)-7-ethyl-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC)[C@H]2CC#N KAOQIYYLGAOMIG-UWJYYQICSA-N 0.000 description 1
- BGOOSPGALTUPIG-UHFFFAOYSA-N 1-[4-[4-(3,3-dimethylmorpholin-4-yl)-7-(2-methoxyethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2C(COCC2)(C)C)=NC2=C1CCN(CCOC)C2 BGOOSPGALTUPIG-UHFFFAOYSA-N 0.000 description 1
- VKNRIIVSYZIGKQ-UHFFFAOYSA-N 1-[4-[4-(3,6-dihydro-2h-pyran-4-yl)-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1C=2CCOCC=2)=NC2=C1CCN(C=1N=CC=CN=1)C2 VKNRIIVSYZIGKQ-UHFFFAOYSA-N 0.000 description 1
- FZDDWCXMXWMWMO-KRWDZBQOSA-N 1-[4-[4-[(3s)-3-ethylmorpholin-4-yl]-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(2-hydroxyethyl)urea Chemical compound CC[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCCO)=CC=2)=NC2=C1CCNC2 FZDDWCXMXWMWMO-KRWDZBQOSA-N 0.000 description 1
- YFJSMESLYVMZLD-FQEVSTJZSA-N 1-[4-[4-[(3s)-3-ethylmorpholin-4-yl]-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(1,2-oxazol-3-yl)urea Chemical compound CC[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3=NOC=C3)=CC=2)=NC2=C1CCN(C=1N=CC=CN=1)C2 YFJSMESLYVMZLD-FQEVSTJZSA-N 0.000 description 1
- KDDWBAMYDUGMNX-FQEVSTJZSA-N 1-[4-[4-[(3s)-3-ethylmorpholin-4-yl]-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(2-hydroxyethyl)urea Chemical compound CC[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCCO)=CC=2)=NC2=C1CCN(C=1N=CC=CN=1)C2 KDDWBAMYDUGMNX-FQEVSTJZSA-N 0.000 description 1
- LBUQRQAZTNXNCW-FQEVSTJZSA-N 1-[4-[4-[(3s)-3-ethylmorpholin-4-yl]-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(5-methyloxadiazol-4-yl)urea Chemical compound CC[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3=C(ON=N3)C)=CC=2)=NC2=C1CCN(C=1N=CC=CN=1)C2 LBUQRQAZTNXNCW-FQEVSTJZSA-N 0.000 description 1
- FCXDRULXMJBVKD-NRFANRHFSA-N 1-[4-[4-[(3s)-3-ethylmorpholin-4-yl]-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(oxetan-3-yl)urea Chemical compound CC[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3COC3)=CC=2)=NC2=C1CCN(C=1N=CC=CN=1)C2 FCXDRULXMJBVKD-NRFANRHFSA-N 0.000 description 1
- LRFQTYFPMHOIBH-KRWDZBQOSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(2-methylpyrimidin-4-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(1,2-oxazol-3-yl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3=NOC=C3)=CC=2)=NC2=C1CCN(C=1N=C(C)N=CC=1)C2 LRFQTYFPMHOIBH-KRWDZBQOSA-N 0.000 description 1
- AQUKHHVKBXACQV-SFHVURJKSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(6-methylpyrimidin-4-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(1,2-oxazol-3-yl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3=NOC=C3)=CC=2)=NC2=C1CCN(C=1N=CN=C(C)C=1)C2 AQUKHHVKBXACQV-SFHVURJKSA-N 0.000 description 1
- LMFOVPLOCRBHKD-SFHVURJKSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(6-methylpyrimidin-4-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(oxetan-3-yl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3COC3)=CC=2)=NC2=C1CCN(C=1N=CN=C(C)C=1)C2 LMFOVPLOCRBHKD-SFHVURJKSA-N 0.000 description 1
- QRNDHTQOHZQORK-INIZCTEOSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(oxetan-3-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(1,2-oxazol-3-yl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3=NOC=C3)=CC=2)=NC2=C1CCN(C1COC1)C2 QRNDHTQOHZQORK-INIZCTEOSA-N 0.000 description 1
- MRBBSPWVDZFPGM-KRWDZBQOSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(oxetan-3-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(1-methylpyrazol-4-yl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3=CN(C)N=C3)=CC=2)=NC2=C1CCN(C1COC1)C2 MRBBSPWVDZFPGM-KRWDZBQOSA-N 0.000 description 1
- XVBXYTTVFZKLQO-INIZCTEOSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(oxetan-3-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(5-methyl-1,2-oxazol-3-yl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3=NOC(C)=C3)=CC=2)=NC2=C1CCN(C1COC1)C2 XVBXYTTVFZKLQO-INIZCTEOSA-N 0.000 description 1
- UKFQNJOKTVLIPJ-HNNXBMFYSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(oxetan-3-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(5-methyl-1,3,4-oxadiazol-2-yl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC=3OC(C)=NN=3)=CC=2)=NC2=C1CCN(C1COC1)C2 UKFQNJOKTVLIPJ-HNNXBMFYSA-N 0.000 description 1
- GJKPCPWSMPBAMJ-INIZCTEOSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(oxetan-3-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(oxetan-3-yl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3COC3)=CC=2)=NC2=C1CCN(C1COC1)C2 GJKPCPWSMPBAMJ-INIZCTEOSA-N 0.000 description 1
- QYIWLYAEDVNTOV-KRWDZBQOSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(oxetan-3-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-propan-2-ylurea Chemical compound C1=CC(NC(=O)NC(C)C)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C1COC1)C2 QYIWLYAEDVNTOV-KRWDZBQOSA-N 0.000 description 1
- IUISKHRMZAQDID-IBGZPJMESA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(pyridine-3-carbonyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(2-methylpyrazol-3-yl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC=3N(N=CC=3)C)=CC=2)=NC2=C1CCN(C(=O)C=1C=NC=CC=1)C2 IUISKHRMZAQDID-IBGZPJMESA-N 0.000 description 1
- ODNFJOWFVHTMGI-KRWDZBQOSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-propan-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(1,2-oxazol-3-yl)urea Chemical compound C1N(C(C)C)CCC2=C1N=C(C=1C=CC(NC(=O)NC3=NOC=C3)=CC=1)N=C2N1CCOC[C@@H]1C ODNFJOWFVHTMGI-KRWDZBQOSA-N 0.000 description 1
- LZSGEMHLPRUBMQ-SFHVURJKSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-propan-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(1-methylpyrazol-4-yl)urea Chemical compound C1N(C(C)C)CCC2=C1N=C(C=1C=CC(NC(=O)NC3=CN(C)N=C3)=CC=1)N=C2N1CCOC[C@@H]1C LZSGEMHLPRUBMQ-SFHVURJKSA-N 0.000 description 1
- XAJPHEVLLBBVPT-KRWDZBQOSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-propan-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(5-methyl-1,2-oxazol-3-yl)urea Chemical compound C1N(C(C)C)CCC2=C1N=C(C=1C=CC(NC(=O)NC3=NOC(C)=C3)=CC=1)N=C2N1CCOC[C@@H]1C XAJPHEVLLBBVPT-KRWDZBQOSA-N 0.000 description 1
- WANYHUWJEPZTEO-INIZCTEOSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-propan-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(5-methyl-1,3,4-oxadiazol-2-yl)urea Chemical compound C1N(C(C)C)CCC2=C1N=C(C=1C=CC(NC(=O)NC=3OC(C)=NN=3)=CC=1)N=C2N1CCOC[C@@H]1C WANYHUWJEPZTEO-INIZCTEOSA-N 0.000 description 1
- NWLACGCUQITDEV-HNNXBMFYSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-propanoyl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(2,2,2-trifluoroethyl)urea Chemical compound C1N(C(=O)CC)CCC2=C1N=C(C=1C=CC(NC(=O)NCC(F)(F)F)=CC=1)N=C2N1CCOC[C@@H]1C NWLACGCUQITDEV-HNNXBMFYSA-N 0.000 description 1
- JSDGYZHQXWOVBC-SFHVURJKSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-pyrazin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(3-methyl-1,2-oxazol-5-yl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC=3ON=C(C)C=3)=CC=2)=NC2=C1CCN(C=1N=CC=NC=1)C2 JSDGYZHQXWOVBC-SFHVURJKSA-N 0.000 description 1
- VZTLRZWXJPDFNH-RXVVDRJESA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-pyrazin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-[(3s)-oxolan-3-yl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)N[C@@H]3COCC3)=CC=2)=NC2=C1CCN(C=1N=CC=NC=1)C2 VZTLRZWXJPDFNH-RXVVDRJESA-N 0.000 description 1
- NKODPJKDWDCNPD-KRWDZBQOSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(1,2-oxazol-3-yl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3=NOC=C3)=CC=2)=NC2=C1CCN(C=1N=CC=CN=1)C2 NKODPJKDWDCNPD-KRWDZBQOSA-N 0.000 description 1
- HNENOXZOPZIVOW-SFHVURJKSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(1-methylpyrazol-3-yl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3=NN(C)C=C3)=CC=2)=NC2=C1CCN(C=1N=CC=CN=1)C2 HNENOXZOPZIVOW-SFHVURJKSA-N 0.000 description 1
- FMGZVLQNVZPLDK-SFHVURJKSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(1-methylpyrazol-4-yl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3=CN(C)N=C3)=CC=2)=NC2=C1CCN(C=1N=CC=CN=1)C2 FMGZVLQNVZPLDK-SFHVURJKSA-N 0.000 description 1
- QZFVFXAPMZTSPK-SFHVURJKSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(2-methylpyrazol-3-yl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC=3N(N=CC=3)C)=CC=2)=NC2=C1CCN(C=1N=CC=CN=1)C2 QZFVFXAPMZTSPK-SFHVURJKSA-N 0.000 description 1
- RGYKEFRGSFNXHC-SFHVURJKSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(3-methyl-1,2-oxazol-5-yl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC=3ON=C(C)C=3)=CC=2)=NC2=C1CCN(C=1N=CC=CN=1)C2 RGYKEFRGSFNXHC-SFHVURJKSA-N 0.000 description 1
- JEEDPVXQUXOGJG-INIZCTEOSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(5-methyl-1,3,4-oxadiazol-2-yl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC=3OC(C)=NN=3)=CC=2)=NC2=C1CCN(C=1N=CC=CN=1)C2 JEEDPVXQUXOGJG-INIZCTEOSA-N 0.000 description 1
- AYBFPQLKDHRKGC-SFHVURJKSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-propan-2-ylurea Chemical compound C1=CC(NC(=O)NC(C)C)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=CC=CN=1)C2 AYBFPQLKDHRKGC-SFHVURJKSA-N 0.000 description 1
- KMLIKZUQNYTSBQ-KRWDZBQOSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-pyrimidin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(1,2-oxazol-3-yl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3=NOC=C3)=CC=2)=NC2=C1CCN(C=1N=CN=CC=1)C2 KMLIKZUQNYTSBQ-KRWDZBQOSA-N 0.000 description 1
- DDSBYVQQXUKVDW-INIZCTEOSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-8-oxo-5,6-dihydropyrimido[4,5-a]quinolizin-2-yl]phenyl]-3-(oxetan-3-yl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3COC3)=CC=2)=NC2=C1CCN1C(=O)C=CC=C21 DDSBYVQQXUKVDW-INIZCTEOSA-N 0.000 description 1
- RIHCRMSHOVAUAH-UHFFFAOYSA-N 1-[4-[6-(1-acetylpiperidin-4-yl)-4-(1,4-oxazepan-4-yl)-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCCC2)=NC2=C1CN(C1CCN(CC1)C(C)=O)C2 RIHCRMSHOVAUAH-UHFFFAOYSA-N 0.000 description 1
- FPGFEMDVFPIKJP-UHFFFAOYSA-N 1-[4-[6-(1-acetylpiperidin-4-yl)-4-morpholin-4-yl-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(C1CCN(CC1)C(C)=O)C2 FPGFEMDVFPIKJP-UHFFFAOYSA-N 0.000 description 1
- PHQRGEOYJZNRRJ-INIZCTEOSA-N 1-[4-[6-(2-aminopyrimidin-4-yl)-4-[(3s)-3-methylmorpholin-4-yl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CN(C=1N=C(N)N=CC=1)CC2 PHQRGEOYJZNRRJ-INIZCTEOSA-N 0.000 description 1
- MIFXTNLHLGUNLR-UHFFFAOYSA-N 1-[4-[6-(2-aminopyrimidin-4-yl)-4-morpholin-4-yl-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(C=1N=C(N)N=CC=1)C2 MIFXTNLHLGUNLR-UHFFFAOYSA-N 0.000 description 1
- INRZEKBPKUHPGZ-UHFFFAOYSA-N 1-[4-[6-(2-aminopyrimidin-4-yl)-4-morpholin-4-yl-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(C=1N=C(N)N=CC=1)CC2 INRZEKBPKUHPGZ-UHFFFAOYSA-N 0.000 description 1
- BBCWPSMFWNVQJY-UHFFFAOYSA-N 1-[4-[6-(2-chlorobenzoyl)-4-morpholin-4-yl-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(C(=O)C=1C(=CC=CC=1)Cl)CC2 BBCWPSMFWNVQJY-UHFFFAOYSA-N 0.000 description 1
- CZFGRLVLHQVAIA-INIZCTEOSA-N 1-[4-[6-(2-cyanoacetyl)-4-[(3s)-3-methylmorpholin-4-yl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CN(C(=O)CC#N)CC2 CZFGRLVLHQVAIA-INIZCTEOSA-N 0.000 description 1
- RQJBJGWRSSVQSY-UHFFFAOYSA-N 1-[4-[6-(4-chlorobenzoyl)-4-morpholin-4-yl-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(C(=O)C=1C=CC(Cl)=CC=1)CC2 RQJBJGWRSSVQSY-UHFFFAOYSA-N 0.000 description 1
- SINRDUIMXIAWLB-UHFFFAOYSA-N 1-[4-[6-(benzenesulfonyl)-4-(1,4-oxazepan-4-yl)-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCCC2)=NC2=C1CN(S(=O)(=O)C=1C=CC=CC=1)C2 SINRDUIMXIAWLB-UHFFFAOYSA-N 0.000 description 1
- RVHJWWSUVNNBNK-HNNXBMFYSA-N 1-[4-[6-acetyl-4-[(3s)-3-methylmorpholin-4-yl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CN(C(C)=O)CC2 RVHJWWSUVNNBNK-HNNXBMFYSA-N 0.000 description 1
- ZKDOYFUWWZCOPB-INIZCTEOSA-N 1-[4-[6-cyclopropylsulfonyl-4-[(3s)-3-methylmorpholin-4-yl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CN(S(=O)(=O)C1CC1)CC2 ZKDOYFUWWZCOPB-INIZCTEOSA-N 0.000 description 1
- QLKBILJXKRJJOC-SFHVURJKSA-N 1-[4-[7-(1,3-dioxan-2-ylmethyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC1OCCCO1)C2 QLKBILJXKRJJOC-SFHVURJKSA-N 0.000 description 1
- HZLYYKGUXYZFOL-KRWDZBQOSA-N 1-[4-[7-(1,3-dioxolan-2-ylmethyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC1OCCO1)C2 HZLYYKGUXYZFOL-KRWDZBQOSA-N 0.000 description 1
- FIYQHTZROQXJCR-UHFFFAOYSA-N 1-[4-[7-(1,3-dioxolan-2-ylmethyl)-8-methyl-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(CC1OCCO1)C2C FIYQHTZROQXJCR-UHFFFAOYSA-N 0.000 description 1
- MZZZPGLXICNMFY-IBGZPJMESA-N 1-[4-[7-(1-acetylpiperidin-4-yl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C1CCN(CC1)C(C)=O)C2 MZZZPGLXICNMFY-IBGZPJMESA-N 0.000 description 1
- YNLQAEXSWLHXEC-HXBUSHRASA-N 1-[4-[7-(1-acetylpyrrolidin-3-yl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C1CN(CC1)C(C)=O)C2 YNLQAEXSWLHXEC-HXBUSHRASA-N 0.000 description 1
- ZXPICDZJWDEVNC-KRWDZBQOSA-N 1-[4-[7-(1-cyanocyclopropanecarbonyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)C1(CC1)C#N)C2 ZXPICDZJWDEVNC-KRWDZBQOSA-N 0.000 description 1
- HOURXDLOHGKUCQ-UHFFFAOYSA-N 1-[4-[7-(1-cyanocyclopropanecarbonyl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)C1(CC1)C#N)C2 HOURXDLOHGKUCQ-UHFFFAOYSA-N 0.000 description 1
- KEZDAQSYXXRLRW-FQEVSTJZSA-N 1-[4-[7-(1-cyclopropylpiperidin-4-yl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C1CCN(CC1)C1CC1)C2 KEZDAQSYXXRLRW-FQEVSTJZSA-N 0.000 description 1
- ITCBUVDCCORTIU-UHFFFAOYSA-N 1-[4-[7-(1-cyclopropylpiperidin-4-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C1CCN(CC1)C1CC1)C2 ITCBUVDCCORTIU-UHFFFAOYSA-N 0.000 description 1
- JUTDBFZMMZPLCR-HNNXBMFYSA-N 1-[4-[7-(2,2-difluoroethyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC(F)F)C2 JUTDBFZMMZPLCR-HNNXBMFYSA-N 0.000 description 1
- AFMXAFOQNAZZOR-SFHVURJKSA-N 1-[4-[7-(2,2-dimethylpropyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC(C)(C)C)C2 AFMXAFOQNAZZOR-SFHVURJKSA-N 0.000 description 1
- CVNGSXXDANFZJU-KRWDZBQOSA-N 1-[4-[7-(2,6-dimethoxypyrimidin-4-yl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=C(OC)N=C(OC)C=1)C2 CVNGSXXDANFZJU-KRWDZBQOSA-N 0.000 description 1
- WIGQXPIMNCZOHM-SFHVURJKSA-N 1-[4-[7-(2,6-dimethylpyrimidin-4-yl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=C(C)N=C(C)C=1)C2 WIGQXPIMNCZOHM-SFHVURJKSA-N 0.000 description 1
- KOMAHRDUTXCONW-UHFFFAOYSA-N 1-[4-[7-(2,6-dimethylpyrimidin-4-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=C(C)N=C(C)C=1)C2 KOMAHRDUTXCONW-UHFFFAOYSA-N 0.000 description 1
- UVJBHAWYVOIGOA-INIZCTEOSA-N 1-[4-[7-(2-amino-2-methylpropanoyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)C(C)(C)N)C2 UVJBHAWYVOIGOA-INIZCTEOSA-N 0.000 description 1
- TVNKOPSJAIZIHT-HNNXBMFYSA-N 1-[4-[7-(2-aminoacetyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)CN)C2 TVNKOPSJAIZIHT-HNNXBMFYSA-N 0.000 description 1
- HVUSNPXZGYRIMT-INIZCTEOSA-N 1-[4-[7-(2-aminopyrimidin-4-yl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=C(N)N=CC=1)C2 HVUSNPXZGYRIMT-INIZCTEOSA-N 0.000 description 1
- ZXBJZDUOHKHGEB-UHFFFAOYSA-N 1-[4-[7-(2-aminopyrimidin-4-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=C(N)N=CC=1)C2 ZXBJZDUOHKHGEB-UHFFFAOYSA-N 0.000 description 1
- RPLKQQBOEPWFCP-KRWDZBQOSA-N 1-[4-[7-(2-chloro-6-methylpyrimidin-4-yl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(1,2-oxazol-3-yl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3=NOC=C3)=CC=2)=NC2=C1CCN(C=1N=C(Cl)N=C(C)C=1)C2 RPLKQQBOEPWFCP-KRWDZBQOSA-N 0.000 description 1
- LKYSEFZAXALNIJ-UHFFFAOYSA-N 1-[4-[7-(2-chloro-6-methylpyrimidin-4-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=C(Cl)N=C(C)C=1)C2 LKYSEFZAXALNIJ-UHFFFAOYSA-N 0.000 description 1
- WNUXYNGUFCJADD-INIZCTEOSA-N 1-[4-[7-(2-cyanoacetyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)CC#N)C2 WNUXYNGUFCJADD-INIZCTEOSA-N 0.000 description 1
- LGRLSCIPOCTHOH-KRWDZBQOSA-N 1-[4-[7-(2-cyanoethyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CCC#N)C2 LGRLSCIPOCTHOH-KRWDZBQOSA-N 0.000 description 1
- ALSMLUSPPOLUKQ-SFHVURJKSA-N 1-[4-[7-(2-cyclopropylethyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CCC1CC1)C2 ALSMLUSPPOLUKQ-SFHVURJKSA-N 0.000 description 1
- CAWRSMUWTMWVRL-SFHVURJKSA-N 1-[4-[7-(2-ethoxyethyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CCOCC)C2 CAWRSMUWTMWVRL-SFHVURJKSA-N 0.000 description 1
- CANWTKMXMMLXBL-INIZCTEOSA-N 1-[4-[7-(2-hydroxy-2-methylpropanoyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(1,2-oxazol-3-yl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3=NOC=C3)=CC=2)=NC2=C1CCN(C(=O)C(C)(C)O)C2 CANWTKMXMMLXBL-INIZCTEOSA-N 0.000 description 1
- BCGJHVSCYMVPHY-KRWDZBQOSA-N 1-[4-[7-(2-hydroxy-2-methylpropanoyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(1-methylpyrazol-3-yl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3=NN(C)C=C3)=CC=2)=NC2=C1CCN(C(=O)C(C)(C)O)C2 BCGJHVSCYMVPHY-KRWDZBQOSA-N 0.000 description 1
- SGUGICJEEKHSAV-KRWDZBQOSA-N 1-[4-[7-(2-hydroxy-2-methylpropanoyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(2-methylpyrazol-3-yl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC=3N(N=CC=3)C)=CC=2)=NC2=C1CCN(C(=O)C(C)(C)O)C2 SGUGICJEEKHSAV-KRWDZBQOSA-N 0.000 description 1
- YWIHTNDAEZFLMR-KRWDZBQOSA-N 1-[4-[7-(2-hydroxy-2-methylpropanoyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(3-methyl-1,2-oxazol-5-yl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC=3ON=C(C)C=3)=CC=2)=NC2=C1CCN(C(=O)C(C)(C)O)C2 YWIHTNDAEZFLMR-KRWDZBQOSA-N 0.000 description 1
- ZHFZULAISKELOH-IBGZPJMESA-N 1-[4-[7-(3,3-dimethylbutyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CCC(C)(C)C)C2 ZHFZULAISKELOH-IBGZPJMESA-N 0.000 description 1
- PZCWRUNAEWIYGP-UHFFFAOYSA-N 1-[4-[7-(3-chloropyrazin-2-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1C(=NC=CN=1)Cl)C2 PZCWRUNAEWIYGP-UHFFFAOYSA-N 0.000 description 1
- DRTQRYGPJLZZMP-UHFFFAOYSA-N 1-[4-[7-(3-chloropyrazine-2-carbonyl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)C=1C(=NC=CN=1)Cl)C2 DRTQRYGPJLZZMP-UHFFFAOYSA-N 0.000 description 1
- JVPWJEXBSGEEQD-UHFFFAOYSA-N 1-[4-[7-(3-cyanopyrazin-2-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1C(=NC=CN=1)C#N)C2 JVPWJEXBSGEEQD-UHFFFAOYSA-N 0.000 description 1
- YTJHJWTYQUIWRQ-SFHVURJKSA-N 1-[4-[7-(3-cyanopyridin-2-yl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1C(=CC=CN=1)C#N)C2 YTJHJWTYQUIWRQ-SFHVURJKSA-N 0.000 description 1
- NSOSEUKLQCQDOH-UHFFFAOYSA-N 1-[4-[7-(3-cyanopyridin-2-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1C(=CC=CN=1)C#N)C2 NSOSEUKLQCQDOH-UHFFFAOYSA-N 0.000 description 1
- WXKXALAJQUYMME-UHFFFAOYSA-N 1-[4-[7-(4,6-dimethoxypyrimidin-2-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=C(OC)C=C(OC)N=1)C2 WXKXALAJQUYMME-UHFFFAOYSA-N 0.000 description 1
- RXLBZRLEABZGNX-UHFFFAOYSA-N 1-[4-[7-(4,6-dimethylpyrimidin-2-yl)-4-(1,4-oxazepan-4-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCCC2)=NC2=C1CCN(C=1N=C(C)C=C(C)N=1)C2 RXLBZRLEABZGNX-UHFFFAOYSA-N 0.000 description 1
- XVQLJOKWTBCFGH-IBGZPJMESA-N 1-[4-[7-(4,6-dimethylpyrimidin-2-yl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=C(C)C=C(C)N=1)C2 XVQLJOKWTBCFGH-IBGZPJMESA-N 0.000 description 1
- SAYFKJBELASAIY-UHFFFAOYSA-N 1-[4-[7-(4,6-dimethylpyrimidin-2-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=C(C)C=C(C)N=1)C2 SAYFKJBELASAIY-UHFFFAOYSA-N 0.000 description 1
- ZOABCCWEODHVPL-UHFFFAOYSA-N 1-[4-[7-(4-amino-5-cyanopyrimidin-2-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=C(N)C(C#N)=CN=1)C2 ZOABCCWEODHVPL-UHFFFAOYSA-N 0.000 description 1
- GEOXGGXUMMCWQT-UHFFFAOYSA-N 1-[4-[7-(4-amino-5-methylpyrimidin-2-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=C(N)C(C)=CN=1)C2 GEOXGGXUMMCWQT-UHFFFAOYSA-N 0.000 description 1
- RVLQRSHPZHWKKB-UHFFFAOYSA-N 1-[4-[7-(4-amino-5-nitropyrimidin-2-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=C(N)C(=CN=1)[N+]([O-])=O)C2 RVLQRSHPZHWKKB-UHFFFAOYSA-N 0.000 description 1
- BHYGTRTVJIMPRP-HNNXBMFYSA-N 1-[4-[7-(4-chloro-1,3,5-triazin-2-yl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=C(Cl)N=CN=1)C2 BHYGTRTVJIMPRP-HNNXBMFYSA-N 0.000 description 1
- UZFVWZYRRJUBSN-UHFFFAOYSA-N 1-[4-[7-(4-chloro-6-methylpyrimidin-2-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=C(Cl)C=C(C)N=1)C2 UZFVWZYRRJUBSN-UHFFFAOYSA-N 0.000 description 1
- CAAOBEFEYOXOJB-UHFFFAOYSA-N 1-[4-[7-(4-chlorobenzoyl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)C=1C=CC(Cl)=CC=1)C2 CAAOBEFEYOXOJB-UHFFFAOYSA-N 0.000 description 1
- PKROBZXEKAQOQL-SFHVURJKSA-N 1-[4-[7-(4-cyanopyridin-2-yl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=CC=C(C=1)C#N)C2 PKROBZXEKAQOQL-SFHVURJKSA-N 0.000 description 1
- JGJGFPPOHYJPNR-UHFFFAOYSA-N 1-[4-[7-(4-cyanopyridin-2-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CC=C(C=1)C#N)C2 JGJGFPPOHYJPNR-UHFFFAOYSA-N 0.000 description 1
- YATONOIECSUYSM-UHFFFAOYSA-N 1-[4-[7-(5-aminopyrimidin-2-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CC(N)=CN=1)C2 YATONOIECSUYSM-UHFFFAOYSA-N 0.000 description 1
- HSBSHCNXQDSHGS-UHFFFAOYSA-N 1-[4-[7-(5-chloropyrazin-2-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CC(Cl)=NC=1)C2 HSBSHCNXQDSHGS-UHFFFAOYSA-N 0.000 description 1
- SIBHNYGMTAFZGV-INIZCTEOSA-N 1-[4-[7-(5-cyano-1,3-thiazol-2-yl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1SC(=CN=1)C#N)C2 SIBHNYGMTAFZGV-INIZCTEOSA-N 0.000 description 1
- INPCASIBVFCDMQ-SFHVURJKSA-N 1-[4-[7-(5-cyanopyridin-2-yl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=CC(=CC=1)C#N)C2 INPCASIBVFCDMQ-SFHVURJKSA-N 0.000 description 1
- PDAIASYTWVJCBU-UHFFFAOYSA-N 1-[4-[7-(5-cyanopyridin-2-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CC(=CC=1)C#N)C2 PDAIASYTWVJCBU-UHFFFAOYSA-N 0.000 description 1
- DCNQXWCKKPOADA-INIZCTEOSA-N 1-[4-[7-(5-fluoropyrimidin-2-yl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(1,2-oxazol-3-yl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3=NOC=C3)=CC=2)=NC2=C1CCN(C=1N=CC(F)=CN=1)C2 DCNQXWCKKPOADA-INIZCTEOSA-N 0.000 description 1
- FKPCQPYNUFJSCV-HNNXBMFYSA-N 1-[4-[7-(5-fluoropyrimidin-2-yl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=CC(F)=CN=1)C2 FKPCQPYNUFJSCV-HNNXBMFYSA-N 0.000 description 1
- GOBOEFNDFYQYNT-INIZCTEOSA-N 1-[4-[7-(6-chloro-2-methylpyrimidin-4-yl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(1,2-oxazol-3-yl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3=NOC=C3)=CC=2)=NC2=C1CCN(C=1N=C(C)N=C(Cl)C=1)C2 GOBOEFNDFYQYNT-INIZCTEOSA-N 0.000 description 1
- MHUODGXFMPHMOE-HNNXBMFYSA-N 1-[4-[7-(6-chloro-2-methylpyrimidin-4-yl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=C(C)N=C(Cl)C=1)C2 MHUODGXFMPHMOE-HNNXBMFYSA-N 0.000 description 1
- SOFZJNOGSLYGEZ-UHFFFAOYSA-N 1-[4-[7-(6-chloropyrazin-2-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=C(Cl)C=NC=1)C2 SOFZJNOGSLYGEZ-UHFFFAOYSA-N 0.000 description 1
- ZYTKJUHHRJMYQA-INIZCTEOSA-N 1-[4-[7-(6-chloropyridazin-3-yl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=NC(Cl)=CC=1)C2 ZYTKJUHHRJMYQA-INIZCTEOSA-N 0.000 description 1
- WKSYPIHWVWUQSL-INIZCTEOSA-N 1-[4-[7-(6-chloropyrimidin-4-yl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=CN=C(Cl)C=1)C2 WKSYPIHWVWUQSL-INIZCTEOSA-N 0.000 description 1
- ODBDNECPPRCBNM-UHFFFAOYSA-N 1-[4-[7-(6-cyanopyrazin-2-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=C(C=NC=1)C#N)C2 ODBDNECPPRCBNM-UHFFFAOYSA-N 0.000 description 1
- CXYMRYKYXKXAJS-UHFFFAOYSA-N 1-[4-[7-(6-cyclopropylpyrimidin-4-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CN=C(C=1)C1CC1)C2 CXYMRYKYXKXAJS-UHFFFAOYSA-N 0.000 description 1
- JBUMJMURIDWKGN-INIZCTEOSA-N 1-[4-[7-(azetidin-3-yl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C1CNC1)C2 JBUMJMURIDWKGN-INIZCTEOSA-N 0.000 description 1
- AJXLUYVXXBGMCG-UHFFFAOYSA-N 1-[4-[7-(benzenesulfonyl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(S(=O)(=O)C=1C=CC=CC=1)C2 AJXLUYVXXBGMCG-UHFFFAOYSA-N 0.000 description 1
- ZNZVPQLXDGUJGJ-KRWDZBQOSA-N 1-[4-[7-(cyclopropylmethyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC1CC1)C2 ZNZVPQLXDGUJGJ-KRWDZBQOSA-N 0.000 description 1
- JMPQRSLBPHZEPW-JKSUJKDBSA-N 1-[4-[7-[(2r)-2-aminopropanoyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)[C@@H](C)N)C2 JMPQRSLBPHZEPW-JKSUJKDBSA-N 0.000 description 1
- JMPQRSLBPHZEPW-HOTGVXAUSA-N 1-[4-[7-[(2s)-2-aminopropanoyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)[C@H](C)N)C2 JMPQRSLBPHZEPW-HOTGVXAUSA-N 0.000 description 1
- WBOWVYOJNZTFMV-SFHVURJKSA-N 1-[4-[7-[2-(3,3-difluoropyrrolidin-1-yl)-2-oxoethyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC(=O)N1CC(F)(F)CC1)C2 WBOWVYOJNZTFMV-SFHVURJKSA-N 0.000 description 1
- WCQHVFRSPMLPCH-GHTZIAJQSA-N 1-[4-[7-[[(4r)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C[C@H]1OC(C)(C)OC1)C2 WCQHVFRSPMLPCH-GHTZIAJQSA-N 0.000 description 1
- XZKLRQCNOMOTSB-UHFFFAOYSA-N 1-[4-[7-acetyl-4-(1,4-oxazepan-4-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCCC2)=NC2=C1CCN(C(C)=O)C2 XZKLRQCNOMOTSB-UHFFFAOYSA-N 0.000 description 1
- POMYOFXSUPNSDM-IBGZPJMESA-N 1-[4-[7-acetyl-4-[(3s)-3-ethylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)CC)=NC2=C1CCN(C(C)=O)C2 POMYOFXSUPNSDM-IBGZPJMESA-N 0.000 description 1
- FTNWYYVDFGJQKI-AWEZNQCLSA-N 1-[4-[7-acetyl-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(2,2,2-trifluoroethyl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCC(F)(F)F)=CC=2)=NC2=C1CCN(C(C)=O)C2 FTNWYYVDFGJQKI-AWEZNQCLSA-N 0.000 description 1
- SNCQRJZIHWNPRH-HNNXBMFYSA-N 1-[4-[7-acetyl-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(2-hydroxyethyl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCCO)=CC=2)=NC2=C1CCN(C(C)=O)C2 SNCQRJZIHWNPRH-HNNXBMFYSA-N 0.000 description 1
- ZJEDGGWJFHHDPY-HNNXBMFYSA-N 1-[4-[7-acetyl-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(C)=O)C2 ZJEDGGWJFHHDPY-HNNXBMFYSA-N 0.000 description 1
- KVKVKIZBOCWZHQ-IBGZPJMESA-N 1-[4-[7-cyclohexyl-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C1CCCCC1)C2 KVKVKIZBOCWZHQ-IBGZPJMESA-N 0.000 description 1
- DVGJQKJHFIBNOB-SFHVURJKSA-N 1-[4-[7-cyclopentyl-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C1CCCC1)C2 DVGJQKJHFIBNOB-SFHVURJKSA-N 0.000 description 1
- ZKOIDYLQWIVFGR-INIZCTEOSA-N 1-[4-[7-cyclopropylsulfonyl-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(S(=O)(=O)C1CC1)C2 ZKOIDYLQWIVFGR-INIZCTEOSA-N 0.000 description 1
- AOTNCBMUGODTFV-INIZCTEOSA-N 1-[4-[7-ethyl-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(1,2-oxazol-3-yl)urea Chemical compound C1N(CC)CCC2=C1N=C(C=1C=CC(NC(=O)NC3=NOC=C3)=CC=1)N=C2N1CCOC[C@@H]1C AOTNCBMUGODTFV-INIZCTEOSA-N 0.000 description 1
- NRPAPDKYVXDAIU-KRWDZBQOSA-N 1-[4-[7-ethyl-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(1-methylpyrazol-4-yl)urea Chemical compound C1N(CC)CCC2=C1N=C(C=1C=CC(NC(=O)NC3=CN(C)N=C3)=CC=1)N=C2N1CCOC[C@@H]1C NRPAPDKYVXDAIU-KRWDZBQOSA-N 0.000 description 1
- BFPKVZMVOYTPBX-INIZCTEOSA-N 1-[4-[7-ethyl-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(5-methyl-1,2-oxazol-3-yl)urea Chemical compound C1N(CC)CCC2=C1N=C(C=1C=CC(NC(=O)NC3=NOC(C)=C3)=CC=1)N=C2N1CCOC[C@@H]1C BFPKVZMVOYTPBX-INIZCTEOSA-N 0.000 description 1
- DDUROLKLTCSGJY-HNNXBMFYSA-N 1-[4-[7-ethyl-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(5-methyl-1,3,4-oxadiazol-2-yl)urea Chemical compound C1N(CC)CCC2=C1N=C(C=1C=CC(NC(=O)NC=3OC(C)=NN=3)=CC=1)N=C2N1CCOC[C@@H]1C DDUROLKLTCSGJY-HNNXBMFYSA-N 0.000 description 1
- KPPRTXKHNKTZSC-AWEZNQCLSA-N 1-[4-[7-formyl-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(2,2,2-trifluoroethyl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCC(F)(F)F)=CC=2)=NC2=C1CCN(C=O)C2 KPPRTXKHNKTZSC-AWEZNQCLSA-N 0.000 description 1
- AOPLCWPORBWYGS-HNNXBMFYSA-N 1-[4-[7-formyl-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(2-hydroxyethyl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCCO)=CC=2)=NC2=C1CCN(C=O)C2 AOPLCWPORBWYGS-HNNXBMFYSA-N 0.000 description 1
- KPTADQXUHBUWBU-HNNXBMFYSA-N 1-[4-[7-methyl-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(1,2-oxazol-3-yl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3=NOC=C3)=CC=2)=NC2=C1CCN(C)C2 KPTADQXUHBUWBU-HNNXBMFYSA-N 0.000 description 1
- KCZIJRMLGCCLTH-INIZCTEOSA-N 1-[4-[7-methyl-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(1-methylpyrazol-4-yl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3=CN(C)N=C3)=CC=2)=NC2=C1CCN(C)C2 KCZIJRMLGCCLTH-INIZCTEOSA-N 0.000 description 1
- XYIZUZUCCUQQIP-HNNXBMFYSA-N 1-[4-[7-methyl-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(5-methyl-1,2-oxazol-3-yl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3=NOC(C)=C3)=CC=2)=NC2=C1CCN(C)C2 XYIZUZUCCUQQIP-HNNXBMFYSA-N 0.000 description 1
- SMNYANOEPNYXAV-AWEZNQCLSA-N 1-[4-[7-methyl-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-(5-methyl-1,3,4-oxadiazol-2-yl)urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC=3OC(C)=NN=3)=CC=2)=NC2=C1CCN(C)C2 SMNYANOEPNYXAV-AWEZNQCLSA-N 0.000 description 1
- YPHHTSOYKSVXNA-HNNXBMFYSA-N 1-[4-[8,8-dimethyl-4-[(3s)-3-methylmorpholin-4-yl]-6,7-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2[C@H](COCC2)C)=C(CCNC2(C)C)C2=N1 YPHHTSOYKSVXNA-HNNXBMFYSA-N 0.000 description 1
- 102100025573 1-alkyl-2-acetylglycerophosphocholine esterase Human genes 0.000 description 1
- HHIRBXHEYVDUAM-UHFFFAOYSA-N 1-chloro-3-isocyanatobenzene Chemical compound ClC1=CC=CC(N=C=O)=C1 HHIRBXHEYVDUAM-UHFFFAOYSA-N 0.000 description 1
- NNEPCCCIPRJSGD-UHFFFAOYSA-N 1-cyano-2-ethyl-3-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]guanidine Chemical compound C1=CC(NC(/NCC)=N/C#N)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CC=CN=1)C2 NNEPCCCIPRJSGD-UHFFFAOYSA-N 0.000 description 1
- QCSHHLCLJANJSR-SFHVURJKSA-N 1-cyano-2-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]guanidine Chemical compound C1=CC(NC(NCC)=NC#N)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=CC=CN=1)C2 QCSHHLCLJANJSR-SFHVURJKSA-N 0.000 description 1
- REARXSRCYZJXIT-UHFFFAOYSA-N 1-cyano-2-methyl-3-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]guanidine Chemical compound C1=CC(NC(/NC)=N\C#N)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CC=CN=1)C2 REARXSRCYZJXIT-UHFFFAOYSA-N 0.000 description 1
- KSJJMSKNZVXAND-UHFFFAOYSA-N 1-cyanocyclopropane-1-carboxylic acid Chemical compound OC(=O)C1(C#N)CC1 KSJJMSKNZVXAND-UHFFFAOYSA-N 0.000 description 1
- NUMXNKHYQMLDEK-UHFFFAOYSA-N 1-cyclobutyl-3-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]urea Chemical compound C=1C=C(C=2N=C(C=3CCN(CC=3N=2)C=2N=CC=CN=2)N2CCOCC2)C=CC=1NC(=O)NC1CCC1 NUMXNKHYQMLDEK-UHFFFAOYSA-N 0.000 description 1
- GVSIVGLVKPRSHB-QHCPKHFHSA-N 1-cyclobutyl-3-[4-[4-[(3s)-3-ethylmorpholin-4-yl]-7-(2-methylpyrimidin-4-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound CC[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3CCC3)=CC=2)=NC2=C1CCN(C=1N=C(C)N=CC=1)C2 GVSIVGLVKPRSHB-QHCPKHFHSA-N 0.000 description 1
- QYNVMQHNDJMHRQ-HNNXBMFYSA-N 1-cyclobutyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3CCC3)=CC=2)=NC2=C1CCNC2 QYNVMQHNDJMHRQ-HNNXBMFYSA-N 0.000 description 1
- NYTPMDOYIQPORF-HNNXBMFYSA-N 1-cyclobutyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3CCC3)=CC=2)=NC2=C1CNCC2 NYTPMDOYIQPORF-HNNXBMFYSA-N 0.000 description 1
- XJBPJWMEWYZCMC-IBGZPJMESA-N 1-cyclobutyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(pyridine-3-carbonyl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3CCC3)=CC=2)=NC2=C1CN(C(=O)C=1C=NC=CC=1)CC2 XJBPJWMEWYZCMC-IBGZPJMESA-N 0.000 description 1
- CLJBXBSYKMAHMT-SFHVURJKSA-N 1-cyclobutyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-pyrimidin-2-yl-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3CCC3)=CC=2)=NC2=C1CN(C=1N=CC=CN=1)CC2 CLJBXBSYKMAHMT-SFHVURJKSA-N 0.000 description 1
- TZIMAPMNJVFWEH-IBGZPJMESA-N 1-cyclobutyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(pyridine-3-carbonyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3CCC3)=CC=2)=NC2=C1CCN(C(=O)C=1C=NC=CC=1)C2 TZIMAPMNJVFWEH-IBGZPJMESA-N 0.000 description 1
- FRLHWPNVASPRGU-SFHVURJKSA-N 1-cyclobutyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-pyrazin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3CCC3)=CC=2)=NC2=C1CCN(C=1N=CC=NC=1)C2 FRLHWPNVASPRGU-SFHVURJKSA-N 0.000 description 1
- BEPZUMMGJHUYKA-SFHVURJKSA-N 1-cyclobutyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3CCC3)=CC=2)=NC2=C1CCN(C=1N=CC=CN=1)C2 BEPZUMMGJHUYKA-SFHVURJKSA-N 0.000 description 1
- KACQECAXPNDQRH-SFHVURJKSA-N 1-cyclobutyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-pyrimidin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3CCC3)=CC=2)=NC2=C1CCN(C=1N=CN=CC=1)C2 KACQECAXPNDQRH-SFHVURJKSA-N 0.000 description 1
- WTVUGMVMNRPOEF-KRWDZBQOSA-N 1-cyclobutyl-3-[4-[6-(2-hydroxy-2-methylpropanoyl)-4-[(3s)-3-methylmorpholin-4-yl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3CCC3)=CC=2)=NC2=C1CN(C(=O)C(C)(C)O)CC2 WTVUGMVMNRPOEF-KRWDZBQOSA-N 0.000 description 1
- KDSQENPUJWGXLC-KRWDZBQOSA-N 1-cyclobutyl-3-[4-[7-(2-hydroxy-2-methylpropanoyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3CCC3)=CC=2)=NC2=C1CCN(C(=O)C(C)(C)O)C2 KDSQENPUJWGXLC-KRWDZBQOSA-N 0.000 description 1
- XIRYAWDMLJRGHR-UHFFFAOYSA-N 1-cyclopentyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea Chemical compound O1C(C)(C)C(C)(C)OB1C(C=C1)=CC=C1NC(=O)NC1CCCC1 XIRYAWDMLJRGHR-UHFFFAOYSA-N 0.000 description 1
- KEYMFEMRYORMSB-UHFFFAOYSA-N 1-cyclopentyl-3-[4-(4-morpholin-4-yl-6-pyrimidin-2-yl-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-yl)phenyl]urea Chemical compound C=1C=C(C=2N=C(C=3CN(CC=3N=2)C=2N=CC=CN=2)N2CCOCC2)C=CC=1NC(=O)NC1CCCC1 KEYMFEMRYORMSB-UHFFFAOYSA-N 0.000 description 1
- FDUSYBSFUXQUPB-UHFFFAOYSA-N 1-cyclopentyl-3-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]urea Chemical compound C=1C=C(C=2N=C(C=3CCN(CC=3N=2)C=2N=CC=CN=2)N2CCOCC2)C=CC=1NC(=O)NC1CCCC1 FDUSYBSFUXQUPB-UHFFFAOYSA-N 0.000 description 1
- QGHKMWUAZMCPIB-UHFFFAOYSA-N 1-cyclopropyl-3-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]urea Chemical compound C=1C=C(C=2N=C(C=3CCN(CC=3N=2)C=2N=CC=CN=2)N2CCOCC2)C=CC=1NC(=O)NC1CC1 QGHKMWUAZMCPIB-UHFFFAOYSA-N 0.000 description 1
- MAFPUZOQSDXUQI-UHFFFAOYSA-N 1-ethyl-3-[2-fluoro-4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]urea Chemical compound C1=C(F)C(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CC=CN=1)C2 MAFPUZOQSDXUQI-UHFFFAOYSA-N 0.000 description 1
- ROSPVOKXEIUKPD-SFHVURJKSA-N 1-ethyl-3-[2-methyl-4-[4-[(3s)-3-methylmorpholin-4-yl]-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=C(C)C(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=CC=CN=1)C2 ROSPVOKXEIUKPD-SFHVURJKSA-N 0.000 description 1
- PITUAFPHQAKRKP-UHFFFAOYSA-N 1-ethyl-3-[4-(4-morpholin-4-yl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCNC2 PITUAFPHQAKRKP-UHFFFAOYSA-N 0.000 description 1
- ORDVRWLPSLCSOI-UHFFFAOYSA-N 1-ethyl-3-[4-(4-morpholin-4-yl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl]urea;hydrochloride Chemical compound Cl.C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCNC2 ORDVRWLPSLCSOI-UHFFFAOYSA-N 0.000 description 1
- XUKBTRPUZIWHIG-UHFFFAOYSA-N 1-ethyl-3-[4-(4-morpholin-4-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CNCC2 XUKBTRPUZIWHIG-UHFFFAOYSA-N 0.000 description 1
- SJYDAILMGCNNFR-UHFFFAOYSA-N 1-ethyl-3-[4-(4-morpholin-4-yl-6-pyrazin-2-yl-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl)phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(C=1N=CC=NC=1)CC2 SJYDAILMGCNNFR-UHFFFAOYSA-N 0.000 description 1
- HSTOUIMRKOEGJK-UHFFFAOYSA-N 1-ethyl-3-[4-(4-morpholin-4-yl-6-pyrimidin-2-yl-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl)phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(C=1N=CC=CN=1)CC2 HSTOUIMRKOEGJK-UHFFFAOYSA-N 0.000 description 1
- ANGLRRNFDQEMOI-UHFFFAOYSA-N 1-ethyl-3-[4-(4-morpholin-4-yl-7-piperidin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C1CCNCC1)C2 ANGLRRNFDQEMOI-UHFFFAOYSA-N 0.000 description 1
- WAOYOTAWAFPMKA-UHFFFAOYSA-N 1-ethyl-3-[4-(4-morpholin-4-yl-7-propanoyl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)CC)C2 WAOYOTAWAFPMKA-UHFFFAOYSA-N 0.000 description 1
- DXKSCWKPRQTLGV-UHFFFAOYSA-N 1-ethyl-3-[4-(4-morpholin-4-yl-7-pyridin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CC=CC=1)C2 DXKSCWKPRQTLGV-UHFFFAOYSA-N 0.000 description 1
- QRWVDTPKDVYXGE-UHFFFAOYSA-N 1-ethyl-3-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-2-yl)phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CC=CN=1)CC2 QRWVDTPKDVYXGE-UHFFFAOYSA-N 0.000 description 1
- GONDQBGXBXPIQL-UHFFFAOYSA-N 1-ethyl-3-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CC=CN=1)C2 GONDQBGXBXPIQL-UHFFFAOYSA-N 0.000 description 1
- AIIRZUPOXXVTIM-UHFFFAOYSA-N 1-ethyl-3-[4-(4-morpholin-4-yl-7-pyrimidin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CN=CC=1)C2 AIIRZUPOXXVTIM-UHFFFAOYSA-N 0.000 description 1
- LLROFXKMFAJSRE-UHFFFAOYSA-N 1-ethyl-3-[4-(4-morpholin-4-yl-7-quinolin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=C3C=CC=CC3=CC=1)C2 LLROFXKMFAJSRE-UHFFFAOYSA-N 0.000 description 1
- IXLNEPGLJLXCQL-UHFFFAOYSA-N 1-ethyl-3-[4-(4-morpholin-4-yl-8-oxo-6,7-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2CCOCC2)=C(CCNC2=O)C2=N1 IXLNEPGLJLXCQL-UHFFFAOYSA-N 0.000 description 1
- YLPSBZMSYMRETR-UHFFFAOYSA-N 1-ethyl-3-[4-(4-morpholin-4-ylspiro[6,8-dihydro-5h-pyrido[4,3-d]pyrimidine-7,3'-oxetane]-2-yl)phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CNC1(COC1)C2 YLPSBZMSYMRETR-UHFFFAOYSA-N 0.000 description 1
- DDNIRQXHIPCKKO-UHFFFAOYSA-N 1-ethyl-3-[4-(6-ethyl-4-morpholin-4-ylspiro[5,8-dihydropyrido[4,3-d]pyrimidine-7,3'-oxetane]-2-yl)phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(CC)C1(COC1)C2 DDNIRQXHIPCKKO-UHFFFAOYSA-N 0.000 description 1
- QGMJLQWLABEDML-UHFFFAOYSA-N 1-ethyl-3-[4-(6-methyl-4-morpholin-4-ylspiro[5,8-dihydropyrido[4,3-d]pyrimidine-7,3'-oxetane]-2-yl)phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(C)C1(COC1)C2 QGMJLQWLABEDML-UHFFFAOYSA-N 0.000 description 1
- SEKIFRCYOFMYMZ-UHFFFAOYSA-N 1-ethyl-3-[4-(6-methylsulfonyl-4-morpholin-4-yl-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-yl)phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(S(C)(=O)=O)C2 SEKIFRCYOFMYMZ-UHFFFAOYSA-N 0.000 description 1
- QHAFUCUKJCHENF-UHFFFAOYSA-N 1-ethyl-3-[4-(7-ethylsulfonyl-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(S(=O)(=O)CC)C2 QHAFUCUKJCHENF-UHFFFAOYSA-N 0.000 description 1
- YBQQKZNALVVLKI-UHFFFAOYSA-N 1-ethyl-3-[4-(7-formyl-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=O)C2 YBQQKZNALVVLKI-UHFFFAOYSA-N 0.000 description 1
- FIPDNVBPIVBENA-UHFFFAOYSA-N 1-ethyl-3-[4-(7-methylsulfonyl-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(S(C)(=O)=O)C2 FIPDNVBPIVBENA-UHFFFAOYSA-N 0.000 description 1
- LTDOPQAVCQDQPT-UHFFFAOYSA-N 1-ethyl-3-[4-(8-methyl-4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CC=CN=1)C2C LTDOPQAVCQDQPT-UHFFFAOYSA-N 0.000 description 1
- MNDVMWHWTORNOC-MRXNPFEDSA-N 1-ethyl-3-[4-[(8r)-7-(5-fluoropyrimidin-2-yl)-8-methyl-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CC(F)=CN=1)[C@@H]2C MNDVMWHWTORNOC-MRXNPFEDSA-N 0.000 description 1
- UNZROQNYUHMDLS-DLBZAZTESA-N 1-ethyl-3-[4-[(8r)-7-ethyl-8-methyl-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC)[C@@H]2C UNZROQNYUHMDLS-DLBZAZTESA-N 0.000 description 1
- UKTSLHQACPLECV-GOSISDBHSA-N 1-ethyl-3-[4-[(8r)-8-(2-hydroxyethyl)-4-morpholin-4-yl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN[C@@H]2CCO UKTSLHQACPLECV-GOSISDBHSA-N 0.000 description 1
- PZFXDKFPILQZMV-OAQYLSRUSA-N 1-ethyl-3-[4-[(8r)-8-(2-hydroxyethyl)-7-(2-methoxyethyl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(CCOC)[C@@H]2CCO PZFXDKFPILQZMV-OAQYLSRUSA-N 0.000 description 1
- RISIKBBPPVYYEF-JOCHJYFZSA-N 1-ethyl-3-[4-[(8r)-8-(2-hydroxyethyl)-7-(2-methylpyrimidin-4-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=C(C)N=CC=1)[C@@H]2CCO RISIKBBPPVYYEF-JOCHJYFZSA-N 0.000 description 1
- VVWKJUZAOQZJLR-MRXNPFEDSA-N 1-ethyl-3-[4-[(8r)-8-methyl-4-morpholin-4-yl-7-(oxetan-3-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C1COC1)[C@@H]2C VVWKJUZAOQZJLR-MRXNPFEDSA-N 0.000 description 1
- XFAGCZLLEULQGA-GOSISDBHSA-N 1-ethyl-3-[4-[(8r)-8-methyl-4-morpholin-4-yl-7-(pyrimidin-2-ylmethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(CC=1N=CC=CN=1)[C@@H]2C XFAGCZLLEULQGA-GOSISDBHSA-N 0.000 description 1
- BKNRFDFUYGYHBC-KRWDZBQOSA-N 1-ethyl-3-[4-[(8s)-7-(2-methoxyethyl)-8-methyl-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(CCOC)[C@H]2C BKNRFDFUYGYHBC-KRWDZBQOSA-N 0.000 description 1
- MNDVMWHWTORNOC-INIZCTEOSA-N 1-ethyl-3-[4-[(8s)-7-(5-fluoropyrimidin-2-yl)-8-methyl-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CC(F)=CN=1)[C@H]2C MNDVMWHWTORNOC-INIZCTEOSA-N 0.000 description 1
- UNZROQNYUHMDLS-IRXDYDNUSA-N 1-ethyl-3-[4-[(8s)-7-ethyl-8-methyl-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC)[C@H]2C UNZROQNYUHMDLS-IRXDYDNUSA-N 0.000 description 1
- UKTSLHQACPLECV-SFHVURJKSA-N 1-ethyl-3-[4-[(8s)-8-(2-hydroxyethyl)-4-morpholin-4-yl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN[C@H]2CCO UKTSLHQACPLECV-SFHVURJKSA-N 0.000 description 1
- PZFXDKFPILQZMV-NRFANRHFSA-N 1-ethyl-3-[4-[(8s)-8-(2-hydroxyethyl)-7-(2-methoxyethyl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(CCOC)[C@H]2CCO PZFXDKFPILQZMV-NRFANRHFSA-N 0.000 description 1
- RISIKBBPPVYYEF-QFIPXVFZSA-N 1-ethyl-3-[4-[(8s)-8-(2-hydroxyethyl)-7-(2-methylpyrimidin-4-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=C(C)N=CC=1)[C@H]2CCO RISIKBBPPVYYEF-QFIPXVFZSA-N 0.000 description 1
- ASVMDFSTCJKVSG-GJZGRUSLSA-N 1-ethyl-3-[4-[(8s)-8-methyl-4-[(3s)-3-methylmorpholin-4-yl]-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN[C@H]2C ASVMDFSTCJKVSG-GJZGRUSLSA-N 0.000 description 1
- UWICNJLFXGQKPH-ROUUACIJSA-N 1-ethyl-3-[4-[(8s)-8-methyl-4-[(3s)-3-methylmorpholin-4-yl]-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=CC=CN=1)[C@H]2C UWICNJLFXGQKPH-ROUUACIJSA-N 0.000 description 1
- VVWKJUZAOQZJLR-INIZCTEOSA-N 1-ethyl-3-[4-[(8s)-8-methyl-4-morpholin-4-yl-7-(oxetan-3-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C1COC1)[C@H]2C VVWKJUZAOQZJLR-INIZCTEOSA-N 0.000 description 1
- XFAGCZLLEULQGA-SFHVURJKSA-N 1-ethyl-3-[4-[(8s)-8-methyl-4-morpholin-4-yl-7-(pyrimidin-2-ylmethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(CC=1N=CC=CN=1)[C@H]2C XFAGCZLLEULQGA-SFHVURJKSA-N 0.000 description 1
- KXDSUNZZDKKHPE-UHFFFAOYSA-N 1-ethyl-3-[4-[4-(1,4-oxazepan-4-yl)-6-pyrimidin-2-yl-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCCC2)=NC2=C1CN(C=1N=CC=CN=1)C2 KXDSUNZZDKKHPE-UHFFFAOYSA-N 0.000 description 1
- ZHEVUMQAYMMUOB-UHFFFAOYSA-N 1-ethyl-3-[4-[4-(1,4-oxazepan-4-yl)-7-[4-(trifluoromethyl)pyrimidin-2-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCCC2)=NC2=C1CCN(C=1N=C(C=CN=1)C(F)(F)F)C2 ZHEVUMQAYMMUOB-UHFFFAOYSA-N 0.000 description 1
- UGQRZEVAIWITFK-UHFFFAOYSA-N 1-ethyl-3-[4-[4-(1,4-oxazepan-4-yl)-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCCC2)=NC2=C1CCN(C=1N=CC=CN=1)C2 UGQRZEVAIWITFK-UHFFFAOYSA-N 0.000 description 1
- OKLQOMGOWWZPQR-UHFFFAOYSA-N 1-ethyl-3-[4-[4-(2-methylmorpholin-4-yl)-7-(1,3-thiazole-5-carbonyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CC(C)OCC2)=NC2=C1CCN(C(=O)C=1SC=NC=1)C2 OKLQOMGOWWZPQR-UHFFFAOYSA-N 0.000 description 1
- HHKKPWUGMZOUFU-UHFFFAOYSA-N 1-ethyl-3-[4-[4-(2-methylmorpholin-4-yl)-7-(oxetan-3-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CC(C)OCC2)=NC2=C1CCN(C1COC1)C2 HHKKPWUGMZOUFU-UHFFFAOYSA-N 0.000 description 1
- ULTDDJQATAYSNM-UHFFFAOYSA-N 1-ethyl-3-[4-[4-(oxan-4-yl)-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1C2CCOCC2)=NC2=C1CCN(C=1N=CC=CN=1)C2 ULTDDJQATAYSNM-UHFFFAOYSA-N 0.000 description 1
- PGGSPBGGSFJQBA-KDURUIRLSA-N 1-ethyl-3-[4-[4-[(1r,5s)-3-oxa-8-azabicyclo[3.2.1]octan-8-yl]-7-(oxetan-3-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound N1([C@]2([H])CC[C@]1(COC2)[H])C(C=1CC2)=NC(C=3C=CC(NC(=O)NCC)=CC=3)=NC=1CN2C1COC1 PGGSPBGGSFJQBA-KDURUIRLSA-N 0.000 description 1
- MEYLWEILYQGQQH-BGYRXZFFSA-N 1-ethyl-3-[4-[4-[(1r,5s)-3-oxa-8-azabicyclo[3.2.1]octan-8-yl]-7-propan-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound N1([C@]2([H])CC[C@]1(COC2)[H])C(C=1CCN(CC=1N=1)C(C)C)=NC=1C1=CC=C(NC(=O)NCC)C=C1 MEYLWEILYQGQQH-BGYRXZFFSA-N 0.000 description 1
- GTESUHPJGSIADF-OALUTQOASA-N 1-ethyl-3-[4-[4-[(1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C([C@]1(OC[C@]2([H])C1)[H])N2C(C=1CC2)=NC(C=3C=CC(NC(=O)NCC)=CC=3)=NC=1CN2C1=NC=CC=N1 GTESUHPJGSIADF-OALUTQOASA-N 0.000 description 1
- NJALXOLAXUVMFY-BGYRXZFFSA-N 1-ethyl-3-[4-[4-[(1s,5r)-8-oxa-3-azabicyclo[3.2.1]octan-3-yl]-7-(oxetan-3-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C([C@]1(CC[C@@](C2)(O1)[H])[H])N2C(C=1CC2)=NC(C=3C=CC(NC(=O)NCC)=CC=3)=NC=1CN2C1COC1 NJALXOLAXUVMFY-BGYRXZFFSA-N 0.000 description 1
- BHCAYEAZLNNTDV-BGYRXZFFSA-N 1-ethyl-3-[4-[4-[(1s,5r)-8-oxa-3-azabicyclo[3.2.1]octan-3-yl]-7-propan-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C([C@]1(CC[C@@](C2)(O1)[H])[H])N2C(C=1CCN(CC=1N=1)C(C)C)=NC=1C1=CC=C(NC(=O)NCC)C=C1 BHCAYEAZLNNTDV-BGYRXZFFSA-N 0.000 description 1
- OKBASMBUIJJATA-BGYRXZFFSA-N 1-ethyl-3-[4-[4-[(1s,5r)-8-oxa-3-azabicyclo[3.2.1]octan-3-yl]-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C([C@]1(CC[C@@](C2)(O1)[H])[H])N2C(C=1CC2)=NC(C=3C=CC(NC(=O)NCC)=CC=3)=NC=1CN2C1=NC=CC=N1 OKBASMBUIJJATA-BGYRXZFFSA-N 0.000 description 1
- INFDOHHQVOPVBB-MRXNPFEDSA-N 1-ethyl-3-[4-[4-[(3r)-3-methylmorpholin-4-yl]-6-(1,3-thiazole-2-carbonyl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@@H](COCC2)C)=NC2=C1CN(C(=O)C=1SC=CN=1)CC2 INFDOHHQVOPVBB-MRXNPFEDSA-N 0.000 description 1
- UWJDGAYHMWOJRE-GOSISDBHSA-N 1-ethyl-3-[4-[4-[(3r)-3-methylmorpholin-4-yl]-6-(pyridine-3-carbonyl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@@H](COCC2)C)=NC2=C1CN(C(=O)C=1C=NC=CC=1)CC2 UWJDGAYHMWOJRE-GOSISDBHSA-N 0.000 description 1
- FTIIAXJKRYXXDV-CQSZACIVSA-N 1-ethyl-3-[4-[4-[(3r)-3-methylmorpholin-4-yl]-6-methylsulfonyl-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@@H](COCC2)C)=NC2=C1CN(S(C)(=O)=O)C2 FTIIAXJKRYXXDV-CQSZACIVSA-N 0.000 description 1
- KWQYBYMJBCSAOM-QGZVFWFLSA-N 1-ethyl-3-[4-[4-[(3r)-3-methylmorpholin-4-yl]-6-pyrimidin-2-yl-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@@H](COCC2)C)=NC2=C1CN(C=1N=CC=CN=1)CC2 KWQYBYMJBCSAOM-QGZVFWFLSA-N 0.000 description 1
- NOBOMMMEODGDGV-MRXNPFEDSA-N 1-ethyl-3-[4-[4-[(3r)-3-methylmorpholin-4-yl]-7-(1,3-thiazole-2-carbonyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@@H](COCC2)C)=NC2=C1CCN(C(=O)C=1SC=CN=1)C2 NOBOMMMEODGDGV-MRXNPFEDSA-N 0.000 description 1
- CEUZIUWDFOOCOK-GOSISDBHSA-N 1-ethyl-3-[4-[4-[(3r)-3-methylmorpholin-4-yl]-7-(pyridine-3-carbonyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@@H](COCC2)C)=NC2=C1CCN(C(=O)C=1C=NC=CC=1)C2 CEUZIUWDFOOCOK-GOSISDBHSA-N 0.000 description 1
- WQBAZXIQANTUOY-QGZVFWFLSA-N 1-ethyl-3-[4-[4-[(3r)-3-methylmorpholin-4-yl]-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@@H](COCC2)C)=NC2=C1CCN(C=1N=CC=CN=1)C2 WQBAZXIQANTUOY-QGZVFWFLSA-N 0.000 description 1
- OVIDHWMXFBKIOS-QGZVFWFLSA-N 1-ethyl-3-[4-[4-[(3r)-3-methylmorpholin-4-yl]-7-pyrimidin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@@H](COCC2)C)=NC2=C1CCN(C=1N=CN=CC=1)C2 OVIDHWMXFBKIOS-QGZVFWFLSA-N 0.000 description 1
- MMJUOGJCRDMYBI-SFHVURJKSA-N 1-ethyl-3-[4-[4-[(3s)-3-ethylmorpholin-4-yl]-7-(2,2,2-trifluoroethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)CC)=NC2=C1CCN(CC(F)(F)F)C2 MMJUOGJCRDMYBI-SFHVURJKSA-N 0.000 description 1
- UWMNQDIABSIXEO-FQEVSTJZSA-N 1-ethyl-3-[4-[4-[(3s)-3-ethylmorpholin-4-yl]-7-(5-fluoropyrimidin-2-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)CC)=NC2=C1CCN(C=1N=CC(F)=CN=1)C2 UWMNQDIABSIXEO-FQEVSTJZSA-N 0.000 description 1
- BSJUVKOZRUJXCU-NRFANRHFSA-N 1-ethyl-3-[4-[4-[(3s)-3-ethylmorpholin-4-yl]-7-(oxan-4-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)CC)=NC2=C1CCN(C1CCOCC1)C2 BSJUVKOZRUJXCU-NRFANRHFSA-N 0.000 description 1
- CKHSZDYRGSLRMH-IBGZPJMESA-N 1-ethyl-3-[4-[4-[(3s)-3-ethylmorpholin-4-yl]-7-(oxetan-3-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)CC)=NC2=C1CCN(C1COC1)C2 CKHSZDYRGSLRMH-IBGZPJMESA-N 0.000 description 1
- IIGKVRRWMTXWQJ-KRWDZBQOSA-N 1-ethyl-3-[4-[4-[(3s)-3-ethylmorpholin-4-yl]-7-(trifluoromethylsulfonyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)CC)=NC2=C1CCN(S(=O)(=O)C(F)(F)F)C2 IIGKVRRWMTXWQJ-KRWDZBQOSA-N 0.000 description 1
- LXIQSBGXYNJMHT-SFHVURJKSA-N 1-ethyl-3-[4-[4-[(3s)-3-ethylmorpholin-4-yl]-7-formyl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)CC)=NC2=C1CCN(C=O)C2 LXIQSBGXYNJMHT-SFHVURJKSA-N 0.000 description 1
- YQNFKEPZUZOFRJ-KRWDZBQOSA-N 1-ethyl-3-[4-[4-[(3s)-3-ethylmorpholin-4-yl]-7-methyl-8-oxo-5,6-dihydropyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2[C@H](COCC2)CC)=C(CCN(C)C2=O)C2=N1 YQNFKEPZUZOFRJ-KRWDZBQOSA-N 0.000 description 1
- DEAIZNDRKLRSDG-SFHVURJKSA-N 1-ethyl-3-[4-[4-[(3s)-3-ethylmorpholin-4-yl]-7-methylsulfonyl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)CC)=NC2=C1CCN(S(C)(=O)=O)C2 DEAIZNDRKLRSDG-SFHVURJKSA-N 0.000 description 1
- CAZWRWYIOZSMEL-FQEVSTJZSA-N 1-ethyl-3-[4-[4-[(3s)-3-ethylmorpholin-4-yl]-7-propan-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)CC)=NC2=C1CCN(C(C)C)C2 CAZWRWYIOZSMEL-FQEVSTJZSA-N 0.000 description 1
- PIZQRDRWFRZBOU-FQEVSTJZSA-N 1-ethyl-3-[4-[4-[(3s)-3-ethylmorpholin-4-yl]-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)CC)=NC2=C1CCN(C=1N=CC=CN=1)C2 PIZQRDRWFRZBOU-FQEVSTJZSA-N 0.000 description 1
- QDKPBKXVBMMALJ-HNNXBMFYSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6,7,8,9-tetrahydro-5h-pyrimido[4,5-d]azepin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCNCC2 QDKPBKXVBMMALJ-HNNXBMFYSA-N 0.000 description 1
- JMSAHKAMCSWFDX-KRWDZBQOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylpyrimidin-4-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CN(C=1N=C(C)N=CC=1)CC2 JMSAHKAMCSWFDX-KRWDZBQOSA-N 0.000 description 1
- FAFVCLBKYIWHMR-KRWDZBQOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(3-methyloxetane-3-carbonyl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CN(C(=O)C1(C)COC1)CC2 FAFVCLBKYIWHMR-KRWDZBQOSA-N 0.000 description 1
- PWCVWVKSRNNYKA-SFHVURJKSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(6-methylpyrimidin-4-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CN(C=1N=CN=C(C)C=1)CC2 PWCVWVKSRNNYKA-SFHVURJKSA-N 0.000 description 1
- GKVOTXQBCIYYJV-INIZCTEOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(oxetan-3-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CN(C1COC1)CC2 GKVOTXQBCIYYJV-INIZCTEOSA-N 0.000 description 1
- BWKDRZOXXXRSCV-ZDUSSCGKSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(trifluoromethylsulfonyl)-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CN(S(=O)(=O)C(F)(F)F)C2 BWKDRZOXXXRSCV-ZDUSSCGKSA-N 0.000 description 1
- FTIIAXJKRYXXDV-AWEZNQCLSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-methylsulfonyl-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CN(S(C)(=O)=O)C2 FTIIAXJKRYXXDV-AWEZNQCLSA-N 0.000 description 1
- NSMZIMGRQWNLOV-HNNXBMFYSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-methylsulfonyl-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CN(S(C)(=O)=O)CC2 NSMZIMGRQWNLOV-HNNXBMFYSA-N 0.000 description 1
- AFTNBFPWLCGBFC-KRWDZBQOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-pyrazin-2-yl-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CN(C=1N=CC=NC=1)CC2 AFTNBFPWLCGBFC-KRWDZBQOSA-N 0.000 description 1
- KWQYBYMJBCSAOM-KRWDZBQOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-pyrimidin-2-yl-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CN(C=1N=CC=CN=1)CC2 KWQYBYMJBCSAOM-KRWDZBQOSA-N 0.000 description 1
- WJVWIJFCYSAUBO-INIZCTEOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(1,3,5-triazin-2-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=CN=CN=1)C2 WJVWIJFCYSAUBO-INIZCTEOSA-N 0.000 description 1
- KQOMJXPJSHEDIE-INIZCTEOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(1,3-thiazol-2-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1SC=CN=1)C2 KQOMJXPJSHEDIE-INIZCTEOSA-N 0.000 description 1
- NOBOMMMEODGDGV-INIZCTEOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(1,3-thiazole-2-carbonyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)C=1SC=CN=1)C2 NOBOMMMEODGDGV-INIZCTEOSA-N 0.000 description 1
- YIMYACKJHRFUDU-SFHVURJKSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(1-methyl-2-oxopyridin-4-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C1=CC(=O)N(C)C=C1)C2 YIMYACKJHRFUDU-SFHVURJKSA-N 0.000 description 1
- GGBIJLHPDJOBBN-SFHVURJKSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(1-methyl-6-oxopyridin-2-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N(C(=O)C=CC=1)C)C2 GGBIJLHPDJOBBN-SFHVURJKSA-N 0.000 description 1
- VMNVWMNICPWSGM-SFHVURJKSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(1-methyl-6-oxopyridin-3-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C1=CN(C)C(=O)C=C1)C2 VMNVWMNICPWSGM-SFHVURJKSA-N 0.000 description 1
- LNRDQUYXEAONDR-IBGZPJMESA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(1-methylpiperidin-4-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C1CCN(C)CC1)C2 LNRDQUYXEAONDR-IBGZPJMESA-N 0.000 description 1
- GJGZNKWGPXBKQR-XJDOXCRVSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(1-pyridin-3-ylethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(C)C=1C=NC=CC=1)C2 GJGZNKWGPXBKQR-XJDOXCRVSA-N 0.000 description 1
- ZLNTYBOBIPJSSF-HNNXBMFYSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(2,2,2-trifluoroethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC(F)(F)F)C2 ZLNTYBOBIPJSSF-HNNXBMFYSA-N 0.000 description 1
- FLHZJOFALAWJAH-SFHVURJKSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(2-methylpropyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC(C)C)C2 FLHZJOFALAWJAH-SFHVURJKSA-N 0.000 description 1
- SSAYMYMTSUJLAI-SFHVURJKSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(2-methylpropylsulfonyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(S(=O)(=O)CC(C)C)C2 SSAYMYMTSUJLAI-SFHVURJKSA-N 0.000 description 1
- OESWUISVDCHYDK-KRWDZBQOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(2-methylpyrimidin-4-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=C(C)N=CC=1)C2 OESWUISVDCHYDK-KRWDZBQOSA-N 0.000 description 1
- ILGSVUKMUAAUDX-IBGZPJMESA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(2-morpholin-4-yl-2-oxoethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC(=O)N1CCOCC1)C2 ILGSVUKMUAAUDX-IBGZPJMESA-N 0.000 description 1
- YZFLJHOFKUJLER-IBGZPJMESA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(2-oxo-2-pyrrolidin-1-ylethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC(=O)N1CCCC1)C2 YZFLJHOFKUJLER-IBGZPJMESA-N 0.000 description 1
- BHQVZJBRLXMAGL-HNNXBMFYSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(3-methyl-1,2,4-thiadiazol-5-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1SN=C(C)N=1)C2 BHQVZJBRLXMAGL-HNNXBMFYSA-N 0.000 description 1
- JTLBICJRDXMTBQ-KRWDZBQOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(3-methyloxetane-3-carbonyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)C1(C)COC1)C2 JTLBICJRDXMTBQ-KRWDZBQOSA-N 0.000 description 1
- ITAIJQLNCGAQKM-SFHVURJKSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(3-oxocyclohexen-1-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1CCCC(=O)C=1)C2 ITAIJQLNCGAQKM-SFHVURJKSA-N 0.000 description 1
- GJBQOQYVHRMDRI-KRWDZBQOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(3-oxocyclopenten-1-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1CCC(=O)C=1)C2 GJBQOQYVHRMDRI-KRWDZBQOSA-N 0.000 description 1
- LCOCKZDKCKMWDJ-KRWDZBQOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(4-methyl-1,3-thiazol-2-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1SC=C(C)N=1)C2 LCOCKZDKCKMWDJ-KRWDZBQOSA-N 0.000 description 1
- LVGNJTOYOJYFMW-HNNXBMFYSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(5-methyl-1,3,4-oxadiazol-2-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1OC(C)=NN=1)C2 LVGNJTOYOJYFMW-HNNXBMFYSA-N 0.000 description 1
- KWVVCUWBVNUVJW-HNNXBMFYSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(5-methyl-1,3,4-oxadiazole-2-carbonyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)C=1OC(C)=NN=1)C2 KWVVCUWBVNUVJW-HNNXBMFYSA-N 0.000 description 1
- YTALTNPKIHUGBM-SFHVURJKSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(5-methylpyrimidin-2-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=CC(C)=CN=1)C2 YTALTNPKIHUGBM-SFHVURJKSA-N 0.000 description 1
- PRRUKSACBLTWQS-INIZCTEOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(5-oxo-2h-furan-3-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1COC(=O)C=1)C2 PRRUKSACBLTWQS-INIZCTEOSA-N 0.000 description 1
- ZLUZKYLYTXEBHB-SFHVURJKSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(6-methylpyridazin-3-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=NC(C)=CC=1)C2 ZLUZKYLYTXEBHB-SFHVURJKSA-N 0.000 description 1
- JFXLXTLDGUAURJ-SFHVURJKSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(6-methylpyrimidin-4-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=CN=C(C)C=1)C2 JFXLXTLDGUAURJ-SFHVURJKSA-N 0.000 description 1
- JKZDDUYOSZWIQA-IBGZPJMESA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(oxan-4-ylmethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC1CCOCC1)C2 JKZDDUYOSZWIQA-IBGZPJMESA-N 0.000 description 1
- RGJOJUGRHPQXGF-INIZCTEOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(oxetan-3-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C1COC1)C2 RGJOJUGRHPQXGF-INIZCTEOSA-N 0.000 description 1
- VOSAEYQHGSZZBF-YMXDCFFPSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(oxolan-2-ylmethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC1OCCC1)C2 VOSAEYQHGSZZBF-YMXDCFFPSA-N 0.000 description 1
- RPBUVQMKWYMUKC-DIMJTDRSSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(oxolan-3-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C1COCC1)C2 RPBUVQMKWYMUKC-DIMJTDRSSA-N 0.000 description 1
- KILMPEAWHPLJJQ-OYKVQYDMSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(oxolan-3-ylmethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC1COCC1)C2 KILMPEAWHPLJJQ-OYKVQYDMSA-N 0.000 description 1
- BWOQUIUERUBZBJ-KRWDZBQOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(pyrazine-2-carbonyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)C=1N=CC=NC=1)C2 BWOQUIUERUBZBJ-KRWDZBQOSA-N 0.000 description 1
- LQRUKINDZFKKGG-IBGZPJMESA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(pyridin-3-ylmethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC=1C=NC=CC=1)C2 LQRUKINDZFKKGG-IBGZPJMESA-N 0.000 description 1
- WSDSTEQFXJKMKE-IBGZPJMESA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(pyridin-4-ylmethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC=1C=CN=CC=1)C2 WSDSTEQFXJKMKE-IBGZPJMESA-N 0.000 description 1
- CEUZIUWDFOOCOK-SFHVURJKSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(pyridine-3-carbonyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)C=1C=NC=CC=1)C2 CEUZIUWDFOOCOK-SFHVURJKSA-N 0.000 description 1
- NICYXMDAAHSJBL-SFHVURJKSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(pyrimidin-2-ylmethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC=1N=CC=CN=1)C2 NICYXMDAAHSJBL-SFHVURJKSA-N 0.000 description 1
- CLBUMWXSGBBQMN-AWEZNQCLSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(trifluoromethylsulfonyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(S(=O)(=O)C(F)(F)F)C2 CLBUMWXSGBBQMN-AWEZNQCLSA-N 0.000 description 1
- GBEPSOLQANLUCG-SFHVURJKSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-[(2-methylpyrazol-3-yl)methyl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC=1N(N=CC=1)C)C2 GBEPSOLQANLUCG-SFHVURJKSA-N 0.000 description 1
- CDHWAYZWWOSNKJ-FQEVSTJZSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-[(2-methylpyridin-4-yl)methyl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC=1C=C(C)N=CC=1)C2 CDHWAYZWWOSNKJ-FQEVSTJZSA-N 0.000 description 1
- ZGFJKBNHCSKPFR-SFHVURJKSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-[(2-methylpyrimidin-5-yl)methyl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC=1C=NC(C)=NC=1)C2 ZGFJKBNHCSKPFR-SFHVURJKSA-N 0.000 description 1
- LIRUUVZOCVVAGI-SFHVURJKSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-[(3-methyloxetan-3-yl)methyl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC1(C)COC1)C2 LIRUUVZOCVVAGI-SFHVURJKSA-N 0.000 description 1
- RPBUVQMKWYMUKC-FXAWDEMLSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-[(3r)-oxolan-3-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN([C@H]1COCC1)C2 RPBUVQMKWYMUKC-FXAWDEMLSA-N 0.000 description 1
- NUNRWBXNLAYFBD-FQEVSTJZSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-[(6-methylpyridin-2-yl)methyl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC=1N=C(C)C=CC=1)C2 NUNRWBXNLAYFBD-FQEVSTJZSA-N 0.000 description 1
- CTUMDHPUEMFZFG-FQEVSTJZSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-[(6-methylpyridin-3-yl)methyl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC=1C=NC(C)=CC=1)C2 CTUMDHPUEMFZFG-FQEVSTJZSA-N 0.000 description 1
- ANUGXYJYYZEZTO-QHCPKHFHSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-[1-(pyridin-3-ylmethyl)piperidin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C1CCN(CC=3C=NC=CC=3)CC1)C2 ANUGXYJYYZEZTO-QHCPKHFHSA-N 0.000 description 1
- NFTNLYSRSKEKCY-FQEVSTJZSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC(=O)N1CCN(C)CC1)C2 NFTNLYSRSKEKCY-FQEVSTJZSA-N 0.000 description 1
- MMWQQNUEORDNTP-INIZCTEOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-[2-(trifluoromethyl)pyrimidin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=C(N=CC=1)C(F)(F)F)C2 MMWQQNUEORDNTP-INIZCTEOSA-N 0.000 description 1
- ALFXSAKFBJRZMK-IBGZPJMESA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-[2-[(2-methylpropan-2-yl)oxy]ethyl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CCOC(C)(C)C)C2 ALFXSAKFBJRZMK-IBGZPJMESA-N 0.000 description 1
- VRMCIHPRJUBFJP-INIZCTEOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-[4-(trifluoromethyl)pyrimidin-2-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=C(C=CN=1)C(F)(F)F)C2 VRMCIHPRJUBFJP-INIZCTEOSA-N 0.000 description 1
- VOSAEYQHGSZZBF-GHTZIAJQSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-[[(2r)-oxolan-2-yl]methyl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C[C@@H]1OCCC1)C2 VOSAEYQHGSZZBF-GHTZIAJQSA-N 0.000 description 1
- VOSAEYQHGSZZBF-RXVVDRJESA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-[[(2s)-oxolan-2-yl]methyl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C[C@H]1OCCC1)C2 VOSAEYQHGSZZBF-RXVVDRJESA-N 0.000 description 1
- KILMPEAWHPLJJQ-RBUKOAKNSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-[[(3r)-oxolan-3-yl]methyl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C[C@@H]1COCC1)C2 KILMPEAWHPLJJQ-RBUKOAKNSA-N 0.000 description 1
- PKGSKACLMSVGOU-INIZCTEOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-methylsulfonyl-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(S(C)(=O)=O)CC2 PKGSKACLMSVGOU-INIZCTEOSA-N 0.000 description 1
- RWSCHRBISRWGQQ-KRWDZBQOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-propan-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(C)C)C2 RWSCHRBISRWGQQ-KRWDZBQOSA-N 0.000 description 1
- OPHLZZUPYGMXSK-KRWDZBQOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-propan-2-ylsulfonyl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(S(=O)(=O)C(C)C)C2 OPHLZZUPYGMXSK-KRWDZBQOSA-N 0.000 description 1
- UVJOBNLVQHIBQH-INIZCTEOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-propanoyl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)CC)C2 UVJOBNLVQHIBQH-INIZCTEOSA-N 0.000 description 1
- VPULWAYXSQVWNJ-KRWDZBQOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-propylsulfonyl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1N(S(=O)(=O)CCC)CCC2=C1N=C(C=1C=CC(NC(=O)NCC)=CC=1)N=C2N1CCOC[C@@H]1C VPULWAYXSQVWNJ-KRWDZBQOSA-N 0.000 description 1
- UHBBECJRCILYHF-KRWDZBQOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-pyrazin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=CC=NC=1)C2 UHBBECJRCILYHF-KRWDZBQOSA-N 0.000 description 1
- FAUUWGBRPQXEOZ-KRWDZBQOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-pyridazin-3-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=NC=CC=1)C2 FAUUWGBRPQXEOZ-KRWDZBQOSA-N 0.000 description 1
- WQBAZXIQANTUOY-KRWDZBQOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=CC=CN=1)C2 WQBAZXIQANTUOY-KRWDZBQOSA-N 0.000 description 1
- HRMYKZJADLVFPF-DIMJTDRSSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-pyrrolidin-3-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C1CNCC1)C2 HRMYKZJADLVFPF-DIMJTDRSSA-N 0.000 description 1
- KPNSWQKAUYODAU-INIZCTEOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-8-oxo-7-propan-2-yl-5,6-dihydropyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2[C@H](COCC2)C)=C(CCN(C(C)C)C2=O)C2=N1 KPNSWQKAUYODAU-INIZCTEOSA-N 0.000 description 1
- WCQXNWVPUYSEOW-UHFFFAOYSA-N 1-ethyl-3-[4-[4-morpholin-4-yl-6-(pyridine-4-carbonyl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(C(=O)C=1C=CN=CC=1)CC2 WCQXNWVPUYSEOW-UHFFFAOYSA-N 0.000 description 1
- FDQXDVXWQZRSOM-MDWZMJQESA-N 1-ethyl-3-[4-[4-morpholin-4-yl-6-[(e)-3-phenylprop-2-enoyl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(C(=O)\C=C\C=1C=CC=CC=1)CC2 FDQXDVXWQZRSOM-MDWZMJQESA-N 0.000 description 1
- WQHDUTHWBQGUIM-UHFFFAOYSA-N 1-ethyl-3-[4-[4-morpholin-4-yl-7-(1,3-oxazole-4-carbonyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)C=1N=COC=1)C2 WQHDUTHWBQGUIM-UHFFFAOYSA-N 0.000 description 1
- YRHKHFMWYCLLTM-UHFFFAOYSA-N 1-ethyl-3-[4-[4-morpholin-4-yl-7-(1,3-oxazole-5-carbonyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)C=1OC=NC=1)C2 YRHKHFMWYCLLTM-UHFFFAOYSA-N 0.000 description 1
- KVXNIXMOPZZFLR-UHFFFAOYSA-N 1-ethyl-3-[4-[4-morpholin-4-yl-7-(1,3-thiazole-2-carbonyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)C=1SC=CN=1)C2 KVXNIXMOPZZFLR-UHFFFAOYSA-N 0.000 description 1
- YQHFRHWOSQWERW-UHFFFAOYSA-N 1-ethyl-3-[4-[4-morpholin-4-yl-7-(2,2,2-trifluoroethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(CC(F)(F)F)C2 YQHFRHWOSQWERW-UHFFFAOYSA-N 0.000 description 1
- RCVHEYZLGJTRNF-UHFFFAOYSA-N 1-ethyl-3-[4-[4-morpholin-4-yl-7-(4-morpholin-4-ylpyrimidin-2-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=C(C=CN=1)N1CCOCC1)C2 RCVHEYZLGJTRNF-UHFFFAOYSA-N 0.000 description 1
- UECLEMCDBQTEFE-UHFFFAOYSA-N 1-ethyl-3-[4-[4-morpholin-4-yl-7-(5-nitropyrimidin-2-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CC(=CN=1)[N+]([O-])=O)C2 UECLEMCDBQTEFE-UHFFFAOYSA-N 0.000 description 1
- CNHNOCUFAIDRCU-UHFFFAOYSA-N 1-ethyl-3-[4-[4-morpholin-4-yl-7-(6-oxo-1h-pyridin-2-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1NC(=O)C=CC=1)C2 CNHNOCUFAIDRCU-UHFFFAOYSA-N 0.000 description 1
- NSQUXBZGRLBDGQ-UHFFFAOYSA-N 1-ethyl-3-[4-[4-morpholin-4-yl-7-(6-phenylmethoxypyridin-2-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=C(OCC=3C=CC=CC=3)C=CC=1)C2 NSQUXBZGRLBDGQ-UHFFFAOYSA-N 0.000 description 1
- YNYXLWSTEPYZQL-UHFFFAOYSA-N 1-ethyl-3-[4-[4-morpholin-4-yl-7-(oxetan-3-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C1COC1)C2 YNYXLWSTEPYZQL-UHFFFAOYSA-N 0.000 description 1
- VCTVGQYYVQEUQA-UHFFFAOYSA-N 1-ethyl-3-[4-[4-morpholin-4-yl-7-(pyrazine-2-carbonyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)C=1N=CC=NC=1)C2 VCTVGQYYVQEUQA-UHFFFAOYSA-N 0.000 description 1
- BWJUPWKUUXTVSN-UHFFFAOYSA-N 1-ethyl-3-[4-[4-morpholin-4-yl-7-(pyridine-4-carbonyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)C=1C=CN=CC=1)C2 BWJUPWKUUXTVSN-UHFFFAOYSA-N 0.000 description 1
- CLTJTBGGOMFXLC-UHFFFAOYSA-N 1-ethyl-3-[4-[4-morpholin-4-yl-7-(pyrimidine-2-carbonyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)C=1N=CC=CN=1)C2 CLTJTBGGOMFXLC-UHFFFAOYSA-N 0.000 description 1
- FOUBCZVCXYINHV-UHFFFAOYSA-N 1-ethyl-3-[4-[4-morpholin-4-yl-7-[4-(trifluoromethyl)pyrimidin-2-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=C(C=CN=1)C(F)(F)F)C2 FOUBCZVCXYINHV-UHFFFAOYSA-N 0.000 description 1
- OQMOGHISCTYPIQ-INIZCTEOSA-N 1-ethyl-3-[4-[6-(1-methylimidazol-2-yl)-4-[(3s)-3-methylmorpholin-4-yl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CN(C=1N(C=CN=1)C)C2 OQMOGHISCTYPIQ-INIZCTEOSA-N 0.000 description 1
- RUNAMALIVBITMK-MRXNPFEDSA-N 1-ethyl-3-[4-[6-(2-hydroxy-2-methylpropanoyl)-4-[(3r)-3-methylmorpholin-4-yl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@@H](COCC2)C)=NC2=C1CN(C(=O)C(C)(C)O)CC2 RUNAMALIVBITMK-MRXNPFEDSA-N 0.000 description 1
- ORNAKRJYPJEXGV-INIZCTEOSA-N 1-ethyl-3-[4-[6-(2-methoxyacetyl)-4-[(3s)-3-methylmorpholin-4-yl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CN(C(=O)COC)CC2 ORNAKRJYPJEXGV-INIZCTEOSA-N 0.000 description 1
- JFQNPCWSALNASE-HNNXBMFYSA-N 1-ethyl-3-[4-[6-(5-fluoropyrimidin-2-yl)-4-[(3s)-3-methylmorpholin-4-yl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CN(C=1N=CC(F)=CN=1)C2 JFQNPCWSALNASE-HNNXBMFYSA-N 0.000 description 1
- MHGDTNDUEXGFLY-SFHVURJKSA-N 1-ethyl-3-[4-[6-[2-(2-methoxyethoxy)acetyl]-4-[(3s)-3-methylmorpholin-4-yl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CN(C(=O)COCCOC)CC2 MHGDTNDUEXGFLY-SFHVURJKSA-N 0.000 description 1
- XQLGIXZWCSPJND-HNNXBMFYSA-N 1-ethyl-3-[4-[6-ethylsulfonyl-4-[(3s)-3-methylmorpholin-4-yl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CN(S(=O)(=O)CC)C2 XQLGIXZWCSPJND-HNNXBMFYSA-N 0.000 description 1
- MCNRYYSFTAIDOU-UHFFFAOYSA-N 1-ethyl-3-[4-[6-methylsulfonyl-4-(1,4-oxazepan-4-yl)-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCCC2)=NC2=C1CN(S(C)(=O)=O)C2 MCNRYYSFTAIDOU-UHFFFAOYSA-N 0.000 description 1
- RMRMUPPTMKFPLV-SFHVURJKSA-N 1-ethyl-3-[4-[7-(1-ethylimidazol-2-yl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N(C=CN=1)CC)C2 RMRMUPPTMKFPLV-SFHVURJKSA-N 0.000 description 1
- STPZNRZOLBJDOF-ZVAWYAOSSA-N 1-ethyl-3-[4-[7-(1-methoxypropan-2-yl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(C)COC)C2 STPZNRZOLBJDOF-ZVAWYAOSSA-N 0.000 description 1
- YDBFJNKKPRABKX-UHFFFAOYSA-N 1-ethyl-3-[4-[7-(1-methyl-6-oxopyridin-2-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N(C(=O)C=CC=1)C)C2 YDBFJNKKPRABKX-UHFFFAOYSA-N 0.000 description 1
- RSOZDPHLUHFRGI-UHFFFAOYSA-N 1-ethyl-3-[4-[7-(1-methyl-6-oxopyridin-3-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C1=CN(C)C(=O)C=C1)C2 RSOZDPHLUHFRGI-UHFFFAOYSA-N 0.000 description 1
- WKWQCAVPNSVKPK-KRWDZBQOSA-N 1-ethyl-3-[4-[7-(1-methylazetidin-3-yl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C1CN(C)C1)C2 WKWQCAVPNSVKPK-KRWDZBQOSA-N 0.000 description 1
- GSJFNCRHKGEDIO-KRWDZBQOSA-N 1-ethyl-3-[4-[7-(1-methylcyclopropanecarbonyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)C1(C)CC1)C2 GSJFNCRHKGEDIO-KRWDZBQOSA-N 0.000 description 1
- FXMGSWKMLDLHHE-UHFFFAOYSA-N 1-ethyl-3-[4-[7-(1-methylcyclopropanecarbonyl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)C1(C)CC1)C2 FXMGSWKMLDLHHE-UHFFFAOYSA-N 0.000 description 1
- BALVINFSPVZXGT-KRWDZBQOSA-N 1-ethyl-3-[4-[7-(1-methylimidazol-2-yl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N(C=CN=1)C)C2 BALVINFSPVZXGT-KRWDZBQOSA-N 0.000 description 1
- VIOXIDYOKVUCPY-UHFFFAOYSA-N 1-ethyl-3-[4-[7-(1-methylimidazol-2-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N(C=CN=1)C)C2 VIOXIDYOKVUCPY-UHFFFAOYSA-N 0.000 description 1
- SOTZAMAPCAIEJP-UHFFFAOYSA-N 1-ethyl-3-[4-[7-(1-methylpiperidin-4-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C1CCN(C)CC1)C2 SOTZAMAPCAIEJP-UHFFFAOYSA-N 0.000 description 1
- JXHPDYIYFSVDHJ-UHFFFAOYSA-N 1-ethyl-3-[4-[7-(1-methylpyrazol-4-yl)sulfonyl-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(S(=O)(=O)C1=CN(C)N=C1)C2 JXHPDYIYFSVDHJ-UHFFFAOYSA-N 0.000 description 1
- CBHCURCXOOINRN-UHFFFAOYSA-N 1-ethyl-3-[4-[7-(1-methylsulfonylpiperidin-4-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C1CCN(CC1)S(C)(=O)=O)C2 CBHCURCXOOINRN-UHFFFAOYSA-N 0.000 description 1
- PPPKEUGIYRHNRA-KRWDZBQOSA-N 1-ethyl-3-[4-[7-(2-fluoro-2-methylpropyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC(C)(C)F)C2 PPPKEUGIYRHNRA-KRWDZBQOSA-N 0.000 description 1
- PAJRPQATMSQJDB-MRXNPFEDSA-N 1-ethyl-3-[4-[7-(2-hydroxy-2-methylpropanoyl)-4-[(3r)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@@H](COCC2)C)=NC2=C1CCN(C(=O)C(C)(C)O)C2 PAJRPQATMSQJDB-MRXNPFEDSA-N 0.000 description 1
- PAJRPQATMSQJDB-INIZCTEOSA-N 1-ethyl-3-[4-[7-(2-hydroxy-2-methylpropanoyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)C(C)(C)O)C2 PAJRPQATMSQJDB-INIZCTEOSA-N 0.000 description 1
- SGBMEGKYYIPAHH-UHFFFAOYSA-N 1-ethyl-3-[4-[7-(2-hydroxy-2-methylpropanoyl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)C(C)(C)O)C2 SGBMEGKYYIPAHH-UHFFFAOYSA-N 0.000 description 1
- CDHXPBYVSRDILO-KRWDZBQOSA-N 1-ethyl-3-[4-[7-(2-hydroxy-2-methylpropyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC(C)(C)O)C2 CDHXPBYVSRDILO-KRWDZBQOSA-N 0.000 description 1
- YYHJOFGLKLNOMJ-INIZCTEOSA-N 1-ethyl-3-[4-[7-(2-hydroxyethyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CCO)C2 YYHJOFGLKLNOMJ-INIZCTEOSA-N 0.000 description 1
- NEPIAWARVCBMHC-INIZCTEOSA-N 1-ethyl-3-[4-[7-(2-methoxyacetyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)COC)C2 NEPIAWARVCBMHC-INIZCTEOSA-N 0.000 description 1
- HDVPDAATLZGPRR-KRWDZBQOSA-N 1-ethyl-3-[4-[7-(2-methoxyethyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CCOC)C2 HDVPDAATLZGPRR-KRWDZBQOSA-N 0.000 description 1
- XMSWYDUJTANTLB-UHFFFAOYSA-N 1-ethyl-3-[4-[7-(2-methoxyethyl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(CCOC)C2 XMSWYDUJTANTLB-UHFFFAOYSA-N 0.000 description 1
- BKNRFDFUYGYHBC-UHFFFAOYSA-N 1-ethyl-3-[4-[7-(2-methoxyethyl)-8-methyl-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(CCOC)C2C BKNRFDFUYGYHBC-UHFFFAOYSA-N 0.000 description 1
- HPYUULXWSSUDER-KRWDZBQOSA-N 1-ethyl-3-[4-[7-(2-methoxypyrimidin-4-yl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=C(OC)N=CC=1)C2 HPYUULXWSSUDER-KRWDZBQOSA-N 0.000 description 1
- SWYDRAXHQDAVFI-UHFFFAOYSA-N 1-ethyl-3-[4-[7-(2-methoxypyrimidin-4-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=C(OC)N=CC=1)C2 SWYDRAXHQDAVFI-UHFFFAOYSA-N 0.000 description 1
- ZTWNSMRYYSTDFC-UHFFFAOYSA-N 1-ethyl-3-[4-[7-(2-methylpyrazole-3-carbonyl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)C=1N(N=CC=1)C)C2 ZTWNSMRYYSTDFC-UHFFFAOYSA-N 0.000 description 1
- NIDLMSWUMTYHNT-UHFFFAOYSA-N 1-ethyl-3-[4-[7-(2-methylpyridine-3-carbonyl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)C=1C(=NC=CC=1)C)C2 NIDLMSWUMTYHNT-UHFFFAOYSA-N 0.000 description 1
- JTZWKNGRBFQLNZ-PMACEKPBSA-N 1-ethyl-3-[4-[7-(2-methylpyrimidin-4-yl)-4-[(1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C([C@]1(OC[C@]2([H])C1)[H])N2C(C=1CC2)=NC(C=3C=CC(NC(=O)NCC)=CC=3)=NC=1CN2C1=CC=NC(C)=N1 JTZWKNGRBFQLNZ-PMACEKPBSA-N 0.000 description 1
- FNSZHWMNYKQGDA-UHFFFAOYSA-N 1-ethyl-3-[4-[7-(2-methylpyrimidin-4-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=C(C)N=CC=1)C2 FNSZHWMNYKQGDA-UHFFFAOYSA-N 0.000 description 1
- MGGWIXIAZCQCTN-KRWDZBQOSA-N 1-ethyl-3-[4-[7-(3-fluoropropyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CCCF)C2 MGGWIXIAZCQCTN-KRWDZBQOSA-N 0.000 description 1
- XPWRPAAMCXIGFY-KRWDZBQOSA-N 1-ethyl-3-[4-[7-(3-hydroxy-2,2-dimethylpropanoyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)C(C)(C)CO)C2 XPWRPAAMCXIGFY-KRWDZBQOSA-N 0.000 description 1
- ZFACTYXJKWNMLO-SFHVURJKSA-N 1-ethyl-3-[4-[7-(3-hydroxy-2,2-dimethylpropyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC(C)(C)CO)C2 ZFACTYXJKWNMLO-SFHVURJKSA-N 0.000 description 1
- XQNIGVBRJKXBFW-SFHVURJKSA-N 1-ethyl-3-[4-[7-(3-hydroxy-3-methylbutyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CCC(C)(C)O)C2 XQNIGVBRJKXBFW-SFHVURJKSA-N 0.000 description 1
- UURZSGBKOJLGHS-KRWDZBQOSA-N 1-ethyl-3-[4-[7-(3-hydroxypropyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CCCO)C2 UURZSGBKOJLGHS-KRWDZBQOSA-N 0.000 description 1
- KAAHMQKZZNNJSK-SFHVURJKSA-N 1-ethyl-3-[4-[7-(3-methoxypropyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CCCOC)C2 KAAHMQKZZNNJSK-SFHVURJKSA-N 0.000 description 1
- LGFWCOYTEZADCQ-UHFFFAOYSA-N 1-ethyl-3-[4-[7-(3-methyloxetane-3-carbonyl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)C1(C)COC1)C2 LGFWCOYTEZADCQ-UHFFFAOYSA-N 0.000 description 1
- BTJMFWOJAPJDFD-UHFFFAOYSA-N 1-ethyl-3-[4-[7-(3-methylpyrazine-2-carbonyl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)C=1C(=NC=CN=1)C)C2 BTJMFWOJAPJDFD-UHFFFAOYSA-N 0.000 description 1
- VKVCRPJINBZSKM-UHFFFAOYSA-N 1-ethyl-3-[4-[7-(4-fluorobenzoyl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)C=1C=CC(F)=CC=1)C2 VKVCRPJINBZSKM-UHFFFAOYSA-N 0.000 description 1
- FPBYWTSDAWBDPF-UHFFFAOYSA-N 1-ethyl-3-[4-[7-(4-hydroxycyclohexyl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C1CCC(O)CC1)C2 FPBYWTSDAWBDPF-UHFFFAOYSA-N 0.000 description 1
- JXMQEHFZEMBQTL-UHFFFAOYSA-N 1-ethyl-3-[4-[7-(4-methoxypyrimidin-2-yl)-4-(1,4-oxazepan-4-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCCC2)=NC2=C1CCN(C=1N=C(OC)C=CN=1)C2 JXMQEHFZEMBQTL-UHFFFAOYSA-N 0.000 description 1
- NPSBXOZCJCPJPR-KRWDZBQOSA-N 1-ethyl-3-[4-[7-(4-methoxypyrimidin-2-yl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=C(OC)C=CN=1)C2 NPSBXOZCJCPJPR-KRWDZBQOSA-N 0.000 description 1
- KTIOCMSHVFZRLS-UHFFFAOYSA-N 1-ethyl-3-[4-[7-(4-methoxypyrimidin-2-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=C(OC)C=CN=1)C2 KTIOCMSHVFZRLS-UHFFFAOYSA-N 0.000 description 1
- HOWQBIKEEUYPOK-UHFFFAOYSA-N 1-ethyl-3-[4-[7-(5-ethylpyrimidin-2-yl)-4-(1,4-oxazepan-4-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCCC2)=NC2=C1CCN(C=1N=CC(CC)=CN=1)C2 HOWQBIKEEUYPOK-UHFFFAOYSA-N 0.000 description 1
- HHJGPGDNHWQVED-SFHVURJKSA-N 1-ethyl-3-[4-[7-(5-ethylpyrimidin-2-yl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=CC(CC)=CN=1)C2 HHJGPGDNHWQVED-SFHVURJKSA-N 0.000 description 1
- AMGWQEUNDDGXMM-UHFFFAOYSA-N 1-ethyl-3-[4-[7-(5-ethylpyrimidin-2-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CC(CC)=CN=1)C2 AMGWQEUNDDGXMM-UHFFFAOYSA-N 0.000 description 1
- LXRXYNOYAIGUEW-UHFFFAOYSA-N 1-ethyl-3-[4-[7-(5-fluoro-6-oxo-1h-pyrimidin-2-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=C(O)C(F)=CN=1)C2 LXRXYNOYAIGUEW-UHFFFAOYSA-N 0.000 description 1
- MZWZMTXIIGRMDH-UHFFFAOYSA-N 1-ethyl-3-[4-[7-(5-fluoropyrimidin-2-yl)-4-(1,4-oxazepan-4-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCCC2)=NC2=C1CCN(C=1N=CC(F)=CN=1)C2 MZWZMTXIIGRMDH-UHFFFAOYSA-N 0.000 description 1
- KNWRKJNDBZXKMT-UHFFFAOYSA-N 1-ethyl-3-[4-[7-(5-fluoropyrimidin-2-yl)-4-(4-methoxypiperidin-1-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCC(CC2)OC)=NC2=C1CCN(C=1N=CC(F)=CN=1)C2 KNWRKJNDBZXKMT-UHFFFAOYSA-N 0.000 description 1
- JBFQBNLTFJUHDW-OALUTQOASA-N 1-ethyl-3-[4-[7-(5-fluoropyrimidin-2-yl)-4-[(1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C([C@]1(OC[C@]2([H])C1)[H])N2C(C=1CC2)=NC(C=3C=CC(NC(=O)NCC)=CC=3)=NC=1CN2C1=NC=C(F)C=N1 JBFQBNLTFJUHDW-OALUTQOASA-N 0.000 description 1
- DEQRJEPSLGPYFN-INIZCTEOSA-N 1-ethyl-3-[4-[7-(5-fluoropyrimidin-2-yl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=CC(F)=CN=1)C2 DEQRJEPSLGPYFN-INIZCTEOSA-N 0.000 description 1
- RELQTVYWLFDRCW-UHFFFAOYSA-N 1-ethyl-3-[4-[7-(5-fluoropyrimidin-2-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CC(F)=CN=1)C2 RELQTVYWLFDRCW-UHFFFAOYSA-N 0.000 description 1
- LGEQGSUSADLBCF-INIZCTEOSA-N 1-ethyl-3-[4-[7-(5-fluoropyrimidin-4-yl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1C(=CN=CN=1)F)C2 LGEQGSUSADLBCF-INIZCTEOSA-N 0.000 description 1
- NKEBAYBAJGQYJK-UHFFFAOYSA-N 1-ethyl-3-[4-[7-(5-methylpyrazine-2-carbonyl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)C=1N=CC(C)=NC=1)C2 NKEBAYBAJGQYJK-UHFFFAOYSA-N 0.000 description 1
- KSRJPYCLVDQLBT-KRWDZBQOSA-N 1-ethyl-3-[4-[7-(6-methoxypyridazin-3-yl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=NC(OC)=CC=1)C2 KSRJPYCLVDQLBT-KRWDZBQOSA-N 0.000 description 1
- BNYRMSJDCWQSBA-UHFFFAOYSA-N 1-ethyl-3-[4-[7-(6-methylpyridine-3-carbonyl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)C=1C=NC(C)=CC=1)C2 BNYRMSJDCWQSBA-UHFFFAOYSA-N 0.000 description 1
- WVAIMBYJSLWHFA-OYRHEFFESA-N 1-ethyl-3-[4-[7-(6-methylpyrimidin-4-yl)-4-[(1r,5s)-3-oxa-8-azabicyclo[3.2.1]octan-8-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound N1([C@]2([H])CC[C@]1(COC2)[H])C(C=1CC2)=NC(C=3C=CC(NC(=O)NCC)=CC=3)=NC=1CN2C1=CC(C)=NC=N1 WVAIMBYJSLWHFA-OYRHEFFESA-N 0.000 description 1
- REBVLBYMQDSPPZ-PMACEKPBSA-N 1-ethyl-3-[4-[7-(6-methylpyrimidin-4-yl)-4-[(1s,4s)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C([C@]1(OC[C@]2([H])C1)[H])N2C(C=1CC2)=NC(C=3C=CC(NC(=O)NCC)=CC=3)=NC=1CN2C1=CC(C)=NC=N1 REBVLBYMQDSPPZ-PMACEKPBSA-N 0.000 description 1
- YYZQRDZMKIZNCS-OYRHEFFESA-N 1-ethyl-3-[4-[7-(6-methylpyrimidin-4-yl)-4-[(1s,5r)-8-oxa-3-azabicyclo[3.2.1]octan-3-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C([C@]1(CC[C@@](C2)(O1)[H])[H])N2C(C=1CC2)=NC(C=3C=CC(NC(=O)NCC)=CC=3)=NC=1CN2C1=CC(C)=NC=N1 YYZQRDZMKIZNCS-OYRHEFFESA-N 0.000 description 1
- ICMOJPGGTRQOEE-UHFFFAOYSA-N 1-ethyl-3-[4-[7-(6-methylpyrimidin-4-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CN=C(C)C=1)C2 ICMOJPGGTRQOEE-UHFFFAOYSA-N 0.000 description 1
- OOLISFXQLPCYRN-UHFFFAOYSA-N 1-ethyl-3-[4-[7-(morpholine-4-carbonyl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)N1CCOCC1)C2 OOLISFXQLPCYRN-UHFFFAOYSA-N 0.000 description 1
- MNODJYQOWOACOF-IBGZPJMESA-N 1-ethyl-3-[4-[7-[(2-ethylpyrazol-3-yl)methyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC=1N(N=CC=1)CC)C2 MNODJYQOWOACOF-IBGZPJMESA-N 0.000 description 1
- SYKZPWVPCXNGQJ-SFHVURJKSA-N 1-ethyl-3-[4-[7-[(2-methyl-1,3-dioxolan-2-yl)methyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC1(C)OCCO1)C2 SYKZPWVPCXNGQJ-SFHVURJKSA-N 0.000 description 1
- UMDJZPBQXGMXFD-XMMPIXPASA-N 1-ethyl-3-[4-[7-[(2r)-2-hydroxy-2-phenylacetyl]-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)[C@H](O)C=1C=CC=CC=1)C2 UMDJZPBQXGMXFD-XMMPIXPASA-N 0.000 description 1
- RJPVGUZQZVQQRD-HTAPYJJXSA-N 1-ethyl-3-[4-[7-[(2r)-2-hydroxy-3-methylbutanoyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)[C@H](O)C(C)C)C2 RJPVGUZQZVQQRD-HTAPYJJXSA-N 0.000 description 1
- SIUVCYUVKSWHCM-DLBZAZTESA-N 1-ethyl-3-[4-[7-[(2r)-2-hydroxypropyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C[C@@H](C)O)C2 SIUVCYUVKSWHCM-DLBZAZTESA-N 0.000 description 1
- UMDJZPBQXGMXFD-DEOSSOPVSA-N 1-ethyl-3-[4-[7-[(2s)-2-hydroxy-2-phenylacetyl]-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)[C@@H](O)C=1C=CC=CC=1)C2 UMDJZPBQXGMXFD-DEOSSOPVSA-N 0.000 description 1
- RJPVGUZQZVQQRD-JTSKRJEESA-N 1-ethyl-3-[4-[7-[(2s)-2-hydroxy-3-methylbutanoyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)[C@@H](O)C(C)C)C2 RJPVGUZQZVQQRD-JTSKRJEESA-N 0.000 description 1
- PDFRMPVYVIBRIV-HOTGVXAUSA-N 1-ethyl-3-[4-[7-[(2s)-2-hydroxypropanoyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)[C@H](C)O)C2 PDFRMPVYVIBRIV-HOTGVXAUSA-N 0.000 description 1
- VSGSMSAYTABFMO-HNNXBMFYSA-N 1-ethyl-3-[4-[7-[(2s)-2-hydroxypropanoyl]-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)[C@H](C)O)C2 VSGSMSAYTABFMO-HNNXBMFYSA-N 0.000 description 1
- SIUVCYUVKSWHCM-IRXDYDNUSA-N 1-ethyl-3-[4-[7-[(2s)-2-hydroxypropyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C[C@H](C)O)C2 SIUVCYUVKSWHCM-IRXDYDNUSA-N 0.000 description 1
- WKYQMUKZDQJGBH-ROUUACIJSA-N 1-ethyl-3-[4-[7-[(2s)-2-methoxypropyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C[C@H](C)OC)C2 WKYQMUKZDQJGBH-ROUUACIJSA-N 0.000 description 1
- ILDHUCSXFVZSFE-SFHVURJKSA-N 1-ethyl-3-[4-[7-[2-(2-methoxyethoxy)acetyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)COCCOC)C2 ILDHUCSXFVZSFE-SFHVURJKSA-N 0.000 description 1
- UEENEAVBGJPZGH-BHWOMJMDSA-N 1-ethyl-3-[4-[7-[2-(methylamino)propanoyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)C(C)NC)C2 UEENEAVBGJPZGH-BHWOMJMDSA-N 0.000 description 1
- WPCRFISMGFEOEM-AZUAARDMSA-N 1-ethyl-3-[4-[7-[2-[(3r)-3-fluoropyrrolidin-1-yl]-2-oxoethyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC(=O)N1C[C@H](F)CC1)C2 WPCRFISMGFEOEM-AZUAARDMSA-N 0.000 description 1
- WPCRFISMGFEOEM-ICSRJNTNSA-N 1-ethyl-3-[4-[7-[2-[(3s)-3-fluoropyrrolidin-1-yl]-2-oxoethyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC(=O)N1C[C@@H](F)CC1)C2 WPCRFISMGFEOEM-ICSRJNTNSA-N 0.000 description 1
- XYTTYYVZHYBWJR-SFHVURJKSA-N 1-ethyl-3-[4-[7-ethyl-4-[(3s)-3-ethylmorpholin-4-yl]-8-oxo-5,6-dihydropyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2[C@H](COCC2)CC)=C(CCN(CC)C2=O)C2=N1 XYTTYYVZHYBWJR-SFHVURJKSA-N 0.000 description 1
- BDKPHNLITSDEQD-HNNXBMFYSA-N 1-ethyl-3-[4-[7-ethyl-4-[(3s)-3-methylmorpholin-4-yl]-8-oxo-5,6-dihydropyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2[C@H](COCC2)C)=C(CCN(CC)C2=O)C2=N1 BDKPHNLITSDEQD-HNNXBMFYSA-N 0.000 description 1
- XOXVRGRMSWSOLQ-INIZCTEOSA-N 1-ethyl-3-[4-[7-ethylsulfonyl-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(S(=O)(=O)CC)C2 XOXVRGRMSWSOLQ-INIZCTEOSA-N 0.000 description 1
- VZDGIVNALNEKFQ-HNNXBMFYSA-N 1-ethyl-3-[4-[7-formyl-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=O)C2 VZDGIVNALNEKFQ-HNNXBMFYSA-N 0.000 description 1
- LXWFSZBQJBZQQB-AWEZNQCLSA-N 1-ethyl-3-[4-[7-methyl-4-[(3s)-3-methylmorpholin-4-yl]-8-oxo-5,6-dihydropyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2[C@H](COCC2)C)=C(CCN(C)C2=O)C2=N1 LXWFSZBQJBZQQB-AWEZNQCLSA-N 0.000 description 1
- SSBXRBOVSCFBSE-UHFFFAOYSA-N 1-ethyl-3-[4-[8-(2-hydroxyethyl)-7-(6-methylpyrimidin-4-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CN=C(C)C=1)C2CCO SSBXRBOVSCFBSE-UHFFFAOYSA-N 0.000 description 1
- VVWKJUZAOQZJLR-UHFFFAOYSA-N 1-ethyl-3-[4-[8-methyl-4-morpholin-4-yl-7-(oxetan-3-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C1COC1)C2C VVWKJUZAOQZJLR-UHFFFAOYSA-N 0.000 description 1
- SWIMSWBWEIBPMI-UHFFFAOYSA-N 1-ethyl-3-[4-[8-methyl-7-(2-methylpyrimidin-4-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=C(C)N=CC=1)C2C SWIMSWBWEIBPMI-UHFFFAOYSA-N 0.000 description 1
- XAUPRBYJDPUMKG-MRXNPFEDSA-N 1-ethyl-3-[5-[4-[(3r)-3-methylmorpholin-4-yl]-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]pyridin-2-yl]urea Chemical compound C1=NC(NC(=O)NCC)=CC=C1C(N=C1N2[C@@H](COCC2)C)=NC2=C1CCN(C=1N=CC=CN=1)C2 XAUPRBYJDPUMKG-MRXNPFEDSA-N 0.000 description 1
- KQARHHLUSBXOQM-KRWDZBQOSA-N 1-ethyl-3-[5-[4-[(3s)-3-methylmorpholin-4-yl]-7-(6-methylpyrimidin-4-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]pyridin-2-yl]urea Chemical compound C1=NC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=CN=C(C)C=1)C2 KQARHHLUSBXOQM-KRWDZBQOSA-N 0.000 description 1
- XAUPRBYJDPUMKG-INIZCTEOSA-N 1-ethyl-3-[5-[4-[(3s)-3-methylmorpholin-4-yl]-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]pyridin-2-yl]urea Chemical compound C1=NC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=CC=CN=1)C2 XAUPRBYJDPUMKG-INIZCTEOSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- BKDGCHLEZWJOTK-INIZCTEOSA-N 1-methyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(2-methylpyrimidin-4-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=C(C)N=CC=1)C2 BKDGCHLEZWJOTK-INIZCTEOSA-N 0.000 description 1
- APZOJDUKORKLFW-KRWDZBQOSA-N 1-methyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(6-methylpyrimidin-4-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=CN=C(C)C=1)C2 APZOJDUKORKLFW-KRWDZBQOSA-N 0.000 description 1
- DYVMHSXWAIEUTG-HNNXBMFYSA-N 1-methyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(oxetan-3-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C1COC1)C2 DYVMHSXWAIEUTG-HNNXBMFYSA-N 0.000 description 1
- NDNHJYSZIARDNT-INIZCTEOSA-N 1-methyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=CC=CN=1)C2 NDNHJYSZIARDNT-INIZCTEOSA-N 0.000 description 1
- PCQSOHUAWFCSIS-INIZCTEOSA-N 1-methyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-pyrimidin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=CN=CC=1)C2 PCQSOHUAWFCSIS-INIZCTEOSA-N 0.000 description 1
- GICVCHIXTOUIIL-UHFFFAOYSA-N 1-methyl-n-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]benzimidazol-2-amine Chemical compound N=1C2=CC=CC=C2N(C)C=1NC(C=C1)=CC=C1C(N=1)=NC=2CN(C=3N=CC=CN=3)CCC=2C=1N1CCOCC1 GICVCHIXTOUIIL-UHFFFAOYSA-N 0.000 description 1
- DIZKLZKLNKQFGB-UHFFFAOYSA-N 1-methylcyclopropane-1-carboxylic acid Chemical compound OC(=O)C1(C)CC1 DIZKLZKLNKQFGB-UHFFFAOYSA-N 0.000 description 1
- GGYVTHJIUNGKFZ-UHFFFAOYSA-N 1-methylpiperidin-2-one Chemical compound CN1CCCCC1=O GGYVTHJIUNGKFZ-UHFFFAOYSA-N 0.000 description 1
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- ABEXEQSGABRUHS-UHFFFAOYSA-N 16-methylheptadecyl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC(C)C ABEXEQSGABRUHS-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical class C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- VHADYSUJZAPXOW-UHFFFAOYSA-N 1h-indol-5-ylboronic acid Chemical compound OB(O)C1=CC=C2NC=CC2=C1 VHADYSUJZAPXOW-UHFFFAOYSA-N 0.000 description 1
- BMKPSMACCQFEFO-UHFFFAOYSA-N 1h-phosphonine Chemical compound C=1C=CC=CPC=CC=1 BMKPSMACCQFEFO-UHFFFAOYSA-N 0.000 description 1
- KIPSRYDSZQRPEA-UHFFFAOYSA-N 2,2,2-trifluoroethanamine Chemical compound NCC(F)(F)F KIPSRYDSZQRPEA-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- LBHPCWOIHHEAJJ-UHFFFAOYSA-N 2-(2-aminopyrimidin-5-yl)-6-[(4-methoxyphenyl)methyl]-4-morpholin-4-yl-5h-pyrrolo[3,4-d]pyrimidin-7-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)C(N=C(N=C2N3CCOCC3)C=3C=NC(N)=NC=3)=C2C1 LBHPCWOIHHEAJJ-UHFFFAOYSA-N 0.000 description 1
- TXHAHOVNFDVCCC-UHFFFAOYSA-N 2-(tert-butylazaniumyl)acetate Chemical compound CC(C)(C)NCC(O)=O TXHAHOVNFDVCCC-UHFFFAOYSA-N 0.000 description 1
- 125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 description 1
- SFFSGPCYJCMDJM-UHFFFAOYSA-N 2-[2-(3-oxo-1,2-benzoselenazol-2-yl)ethyl]-1,2-benzoselenazol-3-one Chemical compound [se]1C2=CC=CC=C2C(=O)N1CCN1C(=O)C(C=CC=C2)=C2[se]1 SFFSGPCYJCMDJM-UHFFFAOYSA-N 0.000 description 1
- LSIVPZTUKHIJTR-UHFFFAOYSA-N 2-[2-[4-(ethylcarbamoylamino)phenyl]-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-6-methylpyrimidine-4-carboxylic acid Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=C(C=C(C)N=1)C(O)=O)C2 LSIVPZTUKHIJTR-UHFFFAOYSA-N 0.000 description 1
- CWEQYXZNTCARPA-UHFFFAOYSA-N 2-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)anilino]-1h-pyridin-4-one Chemical compound O=C1C=CNC(NC=2C=CC(=CC=2)C=2N=C(C=3CCN(CC=3N=2)C=2N=CC=CN=2)N2CCOCC2)=C1 CWEQYXZNTCARPA-UHFFFAOYSA-N 0.000 description 1
- COAMFNWRDNRPBM-UHFFFAOYSA-N 2-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)anilino]-1h-pyrimidin-6-one Chemical compound N1C(=O)C=CN=C1NC1=CC=C(C=2N=C(C=3CCN(CC=3N=2)C=2N=CC=CN=2)N2CCOCC2)C=C1 COAMFNWRDNRPBM-UHFFFAOYSA-N 0.000 description 1
- OTXHRRLNXBCFAX-FQEVSTJZSA-N 2-[4-[4-[(3s)-3-ethylmorpholin-4-yl]-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]anilino]-1h-pyrimidin-6-one Chemical compound CC[C@H]1COCCN1C1=NC(C=2C=CC(NC=3NC(=O)C=CN=3)=CC=2)=NC2=C1CCN(C=1N=CC=CN=1)C2 OTXHRRLNXBCFAX-FQEVSTJZSA-N 0.000 description 1
- WTGFSOBWGDKJDB-SFHVURJKSA-N 2-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(6-methylpyrimidin-4-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl]anilino]-1h-pyrimidin-6-one Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC=3NC(=O)C=CN=3)=CC=2)=NC2=C1CN(C=1N=CN=C(C)C=1)CC2 WTGFSOBWGDKJDB-SFHVURJKSA-N 0.000 description 1
- NWTRRRSJKPXUEI-AWEZNQCLSA-N 2-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-methylsulfonyl-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-yl]anilino]-1h-pyrimidin-6-one Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC=3NC(=O)C=CN=3)=CC=2)=NC2=C1CN(S(C)(=O)=O)C2 NWTRRRSJKPXUEI-AWEZNQCLSA-N 0.000 description 1
- HQBUTZRUXILRCZ-KRWDZBQOSA-N 2-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(1,4,5,6-tetrahydropyrimidin-2-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]anilino]-1h-pyrimidin-6-one Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC=3NC(=O)C=CN=3)=CC=2)=NC2=C1CCN(C=1NCCCN=1)C2 HQBUTZRUXILRCZ-KRWDZBQOSA-N 0.000 description 1
- HXIKMXCETFPFGV-SFHVURJKSA-N 2-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(6-methylpyrimidin-4-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]anilino]-1h-pyrimidin-6-one Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC=3NC(=O)C=CN=3)=CC=2)=NC2=C1CCN(C=1N=CN=C(C)C=1)C2 HXIKMXCETFPFGV-SFHVURJKSA-N 0.000 description 1
- OWJHVBPNEZOWTK-SFHVURJKSA-N 2-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(pyridine-3-carbonyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]anilino]-1h-pyrimidin-6-one Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC=3NC(=O)C=CN=3)=CC=2)=NC2=C1CCN(C(=O)C=1C=NC=CC=1)C2 OWJHVBPNEZOWTK-SFHVURJKSA-N 0.000 description 1
- JQEXBGQWLIYHDI-KRWDZBQOSA-N 2-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-propan-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]anilino]-1h-pyrimidin-6-one Chemical compound C1N(C(C)C)CCC2=C1N=C(C=1C=CC(NC=3NC(=O)C=CN=3)=CC=1)N=C2N1CCOC[C@@H]1C JQEXBGQWLIYHDI-KRWDZBQOSA-N 0.000 description 1
- XOVPWJKTKOAVEP-KRWDZBQOSA-N 2-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]anilino]-1h-pyrimidin-6-one Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC=3NC(=O)C=CN=3)=CC=2)=NC2=C1CCN(C=1N=CC=CN=1)C2 XOVPWJKTKOAVEP-KRWDZBQOSA-N 0.000 description 1
- OYQOSMPXJFDWFY-INIZCTEOSA-N 2-[4-[7-(2-hydroxy-2-methylpropanoyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]anilino]-1h-pyrimidin-6-one Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC=3NC(=O)C=CN=3)=CC=2)=NC2=C1CCN(C(=O)C(C)(C)O)C2 OYQOSMPXJFDWFY-INIZCTEOSA-N 0.000 description 1
- LJSWGKRIARPOAX-INIZCTEOSA-N 2-[4-[7-ethyl-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]anilino]-1h-pyrimidin-6-one Chemical compound C1N(CC)CCC2=C1N=C(C=1C=CC(NC=3NC(=O)C=CN=3)=CC=1)N=C2N1CCOC[C@@H]1C LJSWGKRIARPOAX-INIZCTEOSA-N 0.000 description 1
- YZBAXVICWUUHGG-UHFFFAOYSA-N 2-[[4-[2-[dimethyl(oxido)azaniumyl]ethylamino]-5,8-dihydroxy-9,10-dioxoanthracen-1-yl]amino]-n,n-dimethylethanamine oxide Chemical group O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCC[N+](C)(C)[O-])=CC=C2NCC[N+](C)([O-])C YZBAXVICWUUHGG-UHFFFAOYSA-N 0.000 description 1
- URWFVHWDXPDKCN-KRWDZBQOSA-N 2-[[5-[4-[(3s)-3-methylmorpholin-4-yl]-7-(6-methylpyrimidin-4-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]pyridin-2-yl]amino]-1h-pyrimidin-6-one Chemical compound C[C@H]1COCCN1C1=NC(C=2C=NC(NC=3NC(=O)C=CN=3)=CC=2)=NC2=C1CCN(C=1N=CN=C(C)C=1)C2 URWFVHWDXPDKCN-KRWDZBQOSA-N 0.000 description 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- XPBJPGMCFKYBBV-UHFFFAOYSA-N 2-bromoethyl-[2-hydroxy-3-(2-nitroimidazol-1-yl)propyl]azanium;bromide Chemical compound Br.BrCCNCC(O)CN1C=CN=C1[N+]([O-])=O XPBJPGMCFKYBBV-UHFFFAOYSA-N 0.000 description 1
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- COVGXNSRDOYAJD-UHFFFAOYSA-N 2-chloro-4,6-dimethylpyridine Chemical compound CC1=CC(C)=NC(Cl)=C1 COVGXNSRDOYAJD-UHFFFAOYSA-N 0.000 description 1
- WCZPTMALUBBXRK-UHFFFAOYSA-N 2-chloro-4-ethylpyridine Chemical compound CCC1=CC=NC(Cl)=C1 WCZPTMALUBBXRK-UHFFFAOYSA-N 0.000 description 1
- VXLYOURCUVQYLN-UHFFFAOYSA-N 2-chloro-5-methylpyridine Chemical compound CC1=CC=C(Cl)N=C1 VXLYOURCUVQYLN-UHFFFAOYSA-N 0.000 description 1
- XBPPLECAZBTMMK-UHFFFAOYSA-N 2-chloro-n,n-dimethylacetamide Chemical compound CN(C)C(=O)CCl XBPPLECAZBTMMK-UHFFFAOYSA-N 0.000 description 1
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 1
- OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical compound ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 description 1
- JAUPUQRPBNDMDT-UHFFFAOYSA-N 2-chloropyridine-3-carbonitrile Chemical compound ClC1=NC=CC=C1C#N JAUPUQRPBNDMDT-UHFFFAOYSA-N 0.000 description 1
- QRXBTPFMCTXCRD-UHFFFAOYSA-N 2-chloropyridine-4-carbonitrile Chemical compound ClC1=CC(C#N)=CC=N1 QRXBTPFMCTXCRD-UHFFFAOYSA-N 0.000 description 1
- FNRMMDCDHWCQTH-UHFFFAOYSA-N 2-chloropyridine;3-chloropyridine;4-chloropyridine Chemical compound ClC1=CC=NC=C1.ClC1=CC=CN=C1.ClC1=CC=CC=N1 FNRMMDCDHWCQTH-UHFFFAOYSA-N 0.000 description 1
- GEQZTCMVWVDEDF-UHFFFAOYSA-N 2-cyanoacetyl chloride Chemical compound ClC(=O)CC#N GEQZTCMVWVDEDF-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- 229940013085 2-diethylaminoethanol Drugs 0.000 description 1
- WAVYAFBQOXCGSZ-UHFFFAOYSA-N 2-fluoropyrimidine Chemical compound FC1=NC=CC=N1 WAVYAFBQOXCGSZ-UHFFFAOYSA-N 0.000 description 1
- GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 1
- JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 description 1
- KEJCUBBZDRDCRG-KRWDZBQOSA-N 2-methyl-5-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(6-methylpyrimidin-4-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]anilino]-1h-1,2,4-triazol-3-one Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC=3NC(=O)N(C)N=3)=CC=2)=NC2=C1CCN(C=1N=CN=C(C)C=1)C2 KEJCUBBZDRDCRG-KRWDZBQOSA-N 0.000 description 1
- LBURYTYEJALZAH-INIZCTEOSA-N 2-methyl-5-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]anilino]-1h-1,2,4-triazol-3-one Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC=3NC(=O)N(C)N=3)=CC=2)=NC2=C1CCN(C=1N=CC=CN=1)C2 LBURYTYEJALZAH-INIZCTEOSA-N 0.000 description 1
- KUAFQLVIEYVWBU-SFHVURJKSA-N 2-methylpropyl 2-[4-(ethylcarbamoylamino)phenyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)OCC(C)C)C2 KUAFQLVIEYVWBU-SFHVURJKSA-N 0.000 description 1
- HDYOWLRSBHUPKU-SFHVURJKSA-N 2-methylpropyl 2-[4-(ethylcarbamoylamino)phenyl]-4-[(3s)-3-methylmorpholin-4-yl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidine-6-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CN(C(=O)OCC(C)C)CC2 HDYOWLRSBHUPKU-SFHVURJKSA-N 0.000 description 1
- AJPMTHDRANLTII-UHFFFAOYSA-N 2-methylpropyl 2-[4-(ethylcarbamoylamino)phenyl]-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)OCC(C)C)C2 AJPMTHDRANLTII-UHFFFAOYSA-N 0.000 description 1
- CTRPRMNBTVRDFH-UHFFFAOYSA-N 2-n-methyl-1,3,5-triazine-2,4,6-triamine Chemical compound CNC1=NC(N)=NC(N)=N1 CTRPRMNBTVRDFH-UHFFFAOYSA-N 0.000 description 1
- BXVSAYBZSGIURM-UHFFFAOYSA-N 2-phenoxy-4h-1,3,2$l^{5}-benzodioxaphosphinine 2-oxide Chemical compound O1CC2=CC=CC=C2OP1(=O)OC1=CC=CC=C1 BXVSAYBZSGIURM-UHFFFAOYSA-N 0.000 description 1
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical group OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- NDMPLJNOPCLANR-UHFFFAOYSA-N 3,4-dihydroxy-15-(4-hydroxy-18-methoxycarbonyl-5,18-seco-ibogamin-18-yl)-16-methoxy-1-methyl-6,7-didehydro-aspidospermidine-3-carboxylic acid methyl ester Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 NDMPLJNOPCLANR-UHFFFAOYSA-N 0.000 description 1
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
- NUGLIYXAARVRPQ-UHFFFAOYSA-N 3-(2-nitroimidazol-1-yl)propane-1,2-diol Chemical compound OCC(O)CN1C=CN=C1[N+]([O-])=O NUGLIYXAARVRPQ-UHFFFAOYSA-N 0.000 description 1
- BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 1
- WQBQXDKHMCARPM-KRWDZBQOSA-N 3-(ethylamino)-4-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]anilino]cyclobut-3-ene-1,2-dione Chemical compound O=C1C(=O)C(NCC)=C1NC1=CC=C(C=2N=C(C=3CCN(CC=3N=2)C=2N=CC=CN=2)N2[C@H](COCC2)C)C=C1 WQBQXDKHMCARPM-KRWDZBQOSA-N 0.000 description 1
- BRMWTNUJHUMWMS-UHFFFAOYSA-N 3-Methylhistidine Natural products CN1C=NC(CC(N)C(O)=O)=C1 BRMWTNUJHUMWMS-UHFFFAOYSA-N 0.000 description 1
- WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- BXRLWGXPSRYJDZ-UHFFFAOYSA-N 3-cyanoalanine Chemical compound OC(=O)C(N)CC#N BXRLWGXPSRYJDZ-UHFFFAOYSA-N 0.000 description 1
- GJQMTSMWABTHGE-UHFFFAOYSA-N 3-methyl-6-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)anilino]-1h-pyrimidine-2,4-dione Chemical compound N1C(=O)N(C)C(=O)C=C1NC1=CC=C(C=2N=C(C=3CCN(CC=3N=2)C=2N=CC=CN=2)N2CCOCC2)C=C1 GJQMTSMWABTHGE-UHFFFAOYSA-N 0.000 description 1
- GESYRIRPXHIAQL-INIZCTEOSA-N 3-methyl-6-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(1,3-thiazole-2-carbonyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]anilino]-1h-pyrimidine-2,4-dione Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC=3NC(=O)N(C)C(=O)C=3)=CC=2)=NC2=C1CCN(C(=O)C=1SC=CN=1)C2 GESYRIRPXHIAQL-INIZCTEOSA-N 0.000 description 1
- AUYUMYNVQJARFX-KRWDZBQOSA-N 3-methyl-6-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]anilino]-1h-pyrimidine-2,4-dione Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC=3NC(=O)N(C)C(=O)C=3)=CC=2)=NC2=C1CCN(C=1N=CC=CN=1)C2 AUYUMYNVQJARFX-KRWDZBQOSA-N 0.000 description 1
- PMPZEEUNGQSAIQ-UHFFFAOYSA-N 3-methyloxetane-3-carboxylic acid Chemical compound OC(=O)C1(C)COC1 PMPZEEUNGQSAIQ-UHFFFAOYSA-N 0.000 description 1
- JVQIKJMSUIMUDI-UHFFFAOYSA-N 3-pyrroline Chemical compound C1NCC=C1 JVQIKJMSUIMUDI-UHFFFAOYSA-N 0.000 description 1
- FIAZCVSPNZQDRY-UHFFFAOYSA-N 3h-azepine-2-carboxylic acid Chemical compound OC(=O)C1=NC=CC=CC1 FIAZCVSPNZQDRY-UHFFFAOYSA-N 0.000 description 1
- AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 description 1
- FQMSSTZJKSWSMP-UHFFFAOYSA-N 4,5-dioxo-1-(phenylmethyl)-3-pyrrolidinecarboxylic acid ethyl ester Chemical compound O=C1C(=O)C(C(=O)OCC)CN1CC1=CC=CC=C1 FQMSSTZJKSWSMP-UHFFFAOYSA-N 0.000 description 1
- DUFGYCAXVIUXIP-UHFFFAOYSA-N 4,6-dihydroxypyrimidine Chemical compound OC1=CC(O)=NC=N1 DUFGYCAXVIUXIP-UHFFFAOYSA-N 0.000 description 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 description 1
- ROJGNWWTVWLXOU-UHFFFAOYSA-N 4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)aniline Chemical compound C1=CC(N)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CC=CN=1)C2 ROJGNWWTVWLXOU-UHFFFAOYSA-N 0.000 description 1
- LEKXDIYYKNLBCL-UHFFFAOYSA-N 4-(5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-yl)morpholine Chemical compound C1NCCC2=C1N=CN=C2N1CCOCC1 LEKXDIYYKNLBCL-UHFFFAOYSA-N 0.000 description 1
- HMWILCBUYMZUBX-UHFFFAOYSA-N 4-(7-benzyl-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)aniline Chemical compound C1=CC(N)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(CC=1C=CC=CC=1)C2 HMWILCBUYMZUBX-UHFFFAOYSA-N 0.000 description 1
- WIZCXFNNUPFZSL-INIZCTEOSA-N 4-[(3s)-3-methylmorpholin-4-yl]-2-[4-[(6-oxo-1h-pyridin-2-yl)amino]phenyl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carbaldehyde Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC=3NC(=O)C=CC=3)=CC=2)=NC2=C1CCN(C=O)C2 WIZCXFNNUPFZSL-INIZCTEOSA-N 0.000 description 1
- MBJFCQGIOLSXRY-UHFFFAOYSA-N 4-[2-(2-chloro-3h-benzimidazol-5-yl)-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-4-yl]morpholine Chemical compound C=1C=C2NC(Cl)=NC2=CC=1C(N=1)=NC=2CN(C=3N=CC=CN=3)CCC=2C=1N1CCOCC1 MBJFCQGIOLSXRY-UHFFFAOYSA-N 0.000 description 1
- SKIVWCDVTBSRKL-UHFFFAOYSA-N 4-[2-(4-methylsulfonylphenyl)-6,7-dihydro-5h-pyrrolo[3,4-d]pyrimidin-4-yl]morpholine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CNC2 SKIVWCDVTBSRKL-UHFFFAOYSA-N 0.000 description 1
- NLBVSUWSNMMSCL-UHFFFAOYSA-N 4-[2-(4-pyrazol-1-ylphenyl)-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-4-yl]morpholine Chemical compound C1COCCN1C1=NC(C=2C=CC(=CC=2)N2N=CC=C2)=NC2=C1CCN(C=1N=CC=CN=1)C2 NLBVSUWSNMMSCL-UHFFFAOYSA-N 0.000 description 1
- DBFDZMNJARSUCK-UHFFFAOYSA-N 4-[2-[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-4-yl]morpholine Chemical compound O1C(C)=NN=C1C1=CC=C(C=2N=C(C=3CCN(CC=3N=2)C=2N=CC=CN=2)N2CCOCC2)C=C1 DBFDZMNJARSUCK-UHFFFAOYSA-N 0.000 description 1
- HHFBDROWDBDFBR-UHFFFAOYSA-N 4-[[9-chloro-7-(2,6-difluorophenyl)-5H-pyrimido[5,4-d][2]benzazepin-2-yl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=NC=C(CN=C(C=2C3=CC=C(Cl)C=2)C=2C(=CC=CC=2F)F)C3=N1 HHFBDROWDBDFBR-UHFFFAOYSA-N 0.000 description 1
- HZYLVYNCWLAIGF-UHFFFAOYSA-N 4-[[[2-(cyclohexylamino)-2-oxoethyl]-(4-propan-2-ylbenzoyl)amino]methyl]-N-hydroxybenzamide Chemical compound CC(C)c1ccc(cc1)C(=O)N(CC(=O)NC1CCCCC1)Cc1ccc(cc1)C(=O)NO HZYLVYNCWLAIGF-UHFFFAOYSA-N 0.000 description 1
- KISUPFXQEHWGAR-RRKCRQDMSA-N 4-amino-5-bromo-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one Chemical compound C1=C(Br)C(N)=NC(=O)N1[C@@H]1O[C@H](CO)[C@@H](O)C1 KISUPFXQEHWGAR-RRKCRQDMSA-N 0.000 description 1
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 1
- WTDUQQXDOAPXAQ-UHFFFAOYSA-N 4-chloro-2-methoxypyridine Chemical compound COC1=CC(Cl)=CC=N1 WTDUQQXDOAPXAQ-UHFFFAOYSA-N 0.000 description 1
- MVAXKFAQKTWRAH-UHFFFAOYSA-N 4-chloro-6-methylpyrimidine Chemical compound CC1=CC(Cl)=NC=N1 MVAXKFAQKTWRAH-UHFFFAOYSA-N 0.000 description 1
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
- PVMNPAUTCMBOMO-UHFFFAOYSA-N 4-chloropyridine Chemical compound ClC1=CC=NC=C1 PVMNPAUTCMBOMO-UHFFFAOYSA-N 0.000 description 1
- DBPKMSBWOKAKLA-UHFFFAOYSA-N 4-chloropyrimidine Chemical compound ClC1=CC=NC=N1 DBPKMSBWOKAKLA-UHFFFAOYSA-N 0.000 description 1
- LLUBNVPOWFLMEO-NSHDSACASA-N 4-ethyl-n-[(2s)-1-hydroxybutan-2-yl]benzenesulfonamide Chemical compound CC[C@@H](CO)NS(=O)(=O)C1=CC=C(CC)C=C1 LLUBNVPOWFLMEO-NSHDSACASA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 1
- MWVKLRSIDOXBSE-UHFFFAOYSA-N 5-(1-piperidin-4-ylpyrazol-4-yl)-3-(6-pyrrolidin-1-yl-1,3-benzoxazol-2-yl)pyridin-2-amine Chemical compound NC1=NC=C(C2=CN(N=C2)C2CCNCC2)C=C1C(OC1=C2)=NC1=CC=C2N1CCCC1 MWVKLRSIDOXBSE-UHFFFAOYSA-N 0.000 description 1
- AJCHMAHMDCSRDM-UHFFFAOYSA-N 5-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)-1,3-dihydrobenzimidazol-2-one Chemical compound C1=C2NC(=O)NC2=CC=C1C(N=1)=NC=2CN(C=3N=CC=CN=3)CCC=2C=1N1CCOCC1 AJCHMAHMDCSRDM-UHFFFAOYSA-N 0.000 description 1
- KKLFGMWLNRWOBR-UHFFFAOYSA-N 5-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)-1,3-dihydroindol-2-one Chemical compound C=1C=C2NC(=O)CC2=CC=1C(N=1)=NC=2CN(C=3N=CC=CN=3)CCC=2C=1N1CCOCC1 KKLFGMWLNRWOBR-UHFFFAOYSA-N 0.000 description 1
- NMUSYJAQQFHJEW-UHFFFAOYSA-N 5-Azacytidine Natural products O=C1N=C(N)N=CN1C1C(O)C(O)C(CO)O1 NMUSYJAQQFHJEW-UHFFFAOYSA-N 0.000 description 1
- IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
- QSDREJNFZPIFHO-JTQLQIEISA-N 5-[4-[(3s)-3-methylmorpholin-4-yl]-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C[C@H]1COCCN1C1=NC(C=2C=NC(N)=NC=2)=NC2=C1CCNC2 QSDREJNFZPIFHO-JTQLQIEISA-N 0.000 description 1
- QKYUTKCRNBXLLL-ZDUSSCGKSA-N 5-[4-[(3s)-3-methylmorpholin-4-yl]-7-(2-methylpyrimidin-4-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C[C@H]1COCCN1C1=NC(C=2C=NC(N)=NC=2)=NC2=C1CCN(C=1N=C(C)N=CC=1)C2 QKYUTKCRNBXLLL-ZDUSSCGKSA-N 0.000 description 1
- BEXAKUWVGIIQKQ-ZDUSSCGKSA-N 5-[4-[(3s)-3-methylmorpholin-4-yl]-7-propan-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C1N(C(C)C)CCC2=C1N=C(C=1C=NC(N)=NC=1)N=C2N1CCOC[C@@H]1C BEXAKUWVGIIQKQ-ZDUSSCGKSA-N 0.000 description 1
- BKMPHLVSIMSNRI-LBPRGKRZSA-N 5-[7-(5-fluoropyrimidin-2-yl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]pyrimidin-2-amine Chemical compound C[C@H]1COCCN1C1=NC(C=2C=NC(N)=NC=2)=NC2=C1CCN(C=1N=CC(F)=CN=1)C2 BKMPHLVSIMSNRI-LBPRGKRZSA-N 0.000 description 1
- NMUSYJAQQFHJEW-KVTDHHQDSA-N 5-azacytidine Chemical compound O=C1N=C(N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NMUSYJAQQFHJEW-KVTDHHQDSA-N 0.000 description 1
- WOVKYSAHUYNSMH-RRKCRQDMSA-N 5-bromodeoxyuridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(Br)=C1 WOVKYSAHUYNSMH-RRKCRQDMSA-N 0.000 description 1
- UENOZIAUSQAFKH-UHFFFAOYSA-N 5-methyl-n-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]-4,5-dihydro-1h-imidazol-2-amine Chemical compound N1C(C)CN=C1NC1=CC=C(C=2N=C(C=3CCN(CC=3N=2)C=2N=CC=CN=2)N2CCOCC2)C=C1 UENOZIAUSQAFKH-UHFFFAOYSA-N 0.000 description 1
- JRKJSHZDXAXVNR-UHFFFAOYSA-N 6-(7-benzyl-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)quinazolin-2-amine Chemical compound C1=CC2=NC(N)=NC=C2C=C1C(N=C(C=1CC2)N3CCOCC3)=NC=1CN2CC1=CC=CC=C1 JRKJSHZDXAXVNR-UHFFFAOYSA-N 0.000 description 1
- NURPBWMIYGFDJF-UHFFFAOYSA-N 6-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)anilino]-1h-pyrimidine-2,4-dione Chemical compound N1C(=O)NC(=O)C=C1NC1=CC=C(C=2N=C(C=3CCN(CC=3N=2)C=2N=CC=CN=2)N2CCOCC2)C=C1 NURPBWMIYGFDJF-UHFFFAOYSA-N 0.000 description 1
- MXYXTJQGFQIKBX-INIZCTEOSA-N 6-[4-[(3s)-3-methylmorpholin-4-yl]-7-propan-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]-1h-quinolin-2-one Chemical compound C1N(C(C)C)CCC2=C1N=C(C=1C=C3C=CC(=O)NC3=CC=1)N=C2N1CCOC[C@@H]1C MXYXTJQGFQIKBX-INIZCTEOSA-N 0.000 description 1
- WRADKXLYOIOBJR-IBGZPJMESA-N 6-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(6-methylpyrimidin-4-yl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl]anilino]-1h-pyridin-2-one Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC=3NC(=O)C=CC=3)=CC=2)=NC2=C1CN(C=1N=CN=C(C)C=1)CC2 WRADKXLYOIOBJR-IBGZPJMESA-N 0.000 description 1
- SRZSJBIQRBSKCB-HNNXBMFYSA-N 6-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-methylsulfonyl-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-yl]anilino]-1h-pyridin-2-one Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC=3NC(=O)C=CC=3)=CC=2)=NC2=C1CN(S(C)(=O)=O)C2 SRZSJBIQRBSKCB-HNNXBMFYSA-N 0.000 description 1
- HGIAWWVRBGKCRX-INIZCTEOSA-N 6-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(2,2,2-trifluoroethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]anilino]-1h-pyridin-2-one Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC=3NC(=O)C=CC=3)=CC=2)=NC2=C1CCN(CC(F)(F)F)C2 HGIAWWVRBGKCRX-INIZCTEOSA-N 0.000 description 1
- HLNCSVISJRRCTC-SFHVURJKSA-N 6-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(2-methylpyrimidin-4-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]anilino]-1h-pyridin-2-one Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC=3NC(=O)C=CC=3)=CC=2)=NC2=C1CCN(C=1N=C(C)N=CC=1)C2 HLNCSVISJRRCTC-SFHVURJKSA-N 0.000 description 1
- QNCYHKWFPUPYQG-IBGZPJMESA-N 6-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(6-methylpyrimidin-4-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]anilino]-1h-pyridin-2-one Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC=3NC(=O)C=CC=3)=CC=2)=NC2=C1CCN(C=1N=CN=C(C)C=1)C2 QNCYHKWFPUPYQG-IBGZPJMESA-N 0.000 description 1
- AGMXYNJDAAZGMP-IBGZPJMESA-N 6-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(pyridine-3-carbonyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]anilino]-1h-pyridin-2-one Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC=3NC(=O)C=CC=3)=CC=2)=NC2=C1CCN(C(=O)C=1C=NC=CC=1)C2 AGMXYNJDAAZGMP-IBGZPJMESA-N 0.000 description 1
- RVYWAQSNXXFOBG-SFHVURJKSA-N 6-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-propan-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]anilino]-1h-pyridin-2-one Chemical compound C1N(C(C)C)CCC2=C1N=C(C=1C=CC(NC=3NC(=O)C=CC=3)=CC=1)N=C2N1CCOC[C@@H]1C RVYWAQSNXXFOBG-SFHVURJKSA-N 0.000 description 1
- DIUYKNNEISIXEO-KRWDZBQOSA-N 6-[4-[7-(2-hydroxy-2-methylpropanoyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]anilino]-1h-pyridin-2-one Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC=3NC(=O)C=CC=3)=CC=2)=NC2=C1CCN(C(=O)C(C)(C)O)C2 DIUYKNNEISIXEO-KRWDZBQOSA-N 0.000 description 1
- XNYRGMREFLKWIW-INIZCTEOSA-N 6-[4-[7-(2-hydroxy-2-methylpropanoyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]anilino]-3-methyl-1h-pyrimidine-2,4-dione Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC=3NC(=O)N(C)C(=O)C=3)=CC=2)=NC2=C1CCN(C(=O)C(C)(C)O)C2 XNYRGMREFLKWIW-INIZCTEOSA-N 0.000 description 1
- YHRBSCRXBQSHBI-KRWDZBQOSA-N 6-[4-[7-(2-hydroxyethyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]anilino]-1h-pyridin-2-one Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC=3NC(=O)C=CC=3)=CC=2)=NC2=C1CCN(CCO)C2 YHRBSCRXBQSHBI-KRWDZBQOSA-N 0.000 description 1
- HLAISOZRCHKVSU-SFHVURJKSA-N 6-[4-[7-(2-methoxyethyl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]anilino]-1h-pyridin-2-one Chemical compound C1N(CCOC)CCC2=C1N=C(C=1C=CC(NC=3NC(=O)C=CC=3)=CC=1)N=C2N1CCOC[C@@H]1C HLAISOZRCHKVSU-SFHVURJKSA-N 0.000 description 1
- QAUKMVINRHEOHD-KRWDZBQOSA-N 6-[4-[7-(5-fluoropyrimidin-2-yl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]anilino]-1h-pyridin-2-one Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC=3NC(=O)C=CC=3)=CC=2)=NC2=C1CCN(C=1N=CC(F)=CN=1)C2 QAUKMVINRHEOHD-KRWDZBQOSA-N 0.000 description 1
- UNTDCXPHBFCXRG-INIZCTEOSA-N 6-[4-[7-acetyl-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]anilino]-1h-pyridin-2-one Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC=3NC(=O)C=CC=3)=CC=2)=NC2=C1CCN(C(C)=O)C2 UNTDCXPHBFCXRG-INIZCTEOSA-N 0.000 description 1
- BCRWUCQNSJJYFG-FQEVSTJZSA-N 6-[4-[7-benzyl-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]anilino]-3-methyl-1h-pyrimidine-2,4-dione Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC=3NC(=O)N(C)C(=O)C=3)=CC=2)=NC2=C1CCN(CC=1C=CC=CC=1)C2 BCRWUCQNSJJYFG-FQEVSTJZSA-N 0.000 description 1
- BZVINPDDRBPIKP-SFHVURJKSA-N 6-[[5-[4-[(3s)-3-methylmorpholin-4-yl]-7-(6-methylpyrimidin-4-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]pyridin-2-yl]amino]-1h-pyridin-2-one Chemical compound C[C@H]1COCCN1C1=NC(C=2C=NC(NC=3NC(=O)C=CC=3)=CC=2)=NC2=C1CCN(C=1N=CN=C(C)C=1)C2 BZVINPDDRBPIKP-SFHVURJKSA-N 0.000 description 1
- DTMFNXOBHMZXAW-KRWDZBQOSA-N 6-[[5-[4-[(3s)-3-methylmorpholin-4-yl]-7-propan-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]pyridin-2-yl]amino]-1h-pyridin-2-one Chemical compound C1N(C(C)C)CCC2=C1N=C(C=1C=NC(NC=3NC(=O)C=CC=3)=CC=1)N=C2N1CCOC[C@@H]1C DTMFNXOBHMZXAW-KRWDZBQOSA-N 0.000 description 1
- LKPGNRMNMMQFSZ-UHFFFAOYSA-N 6-benzyl-1,4a,5,7,8,8a-hexahydropyrido[4,3-d]pyrimidine-2,4-dione Chemical compound C1C2C(=O)NC(=O)NC2CCN1CC1=CC=CC=C1 LKPGNRMNMMQFSZ-UHFFFAOYSA-N 0.000 description 1
- RZSMZEYQFCOUKN-UHFFFAOYSA-N 6-benzyl-2,4-dichloro-5,7-dihydropyrrolo[3,4-d]pyrimidine Chemical compound C1C=2C(Cl)=NC(Cl)=NC=2CN1CC1=CC=CC=C1 RZSMZEYQFCOUKN-UHFFFAOYSA-N 0.000 description 1
- JLFFQICEMQMXPY-UHFFFAOYSA-N 6-benzyl-2-chloro-4-morpholin-4-yl-5h-pyrrolo[3,4-d]pyrimidin-7-one Chemical compound C1C=2C(N3CCOCC3)=NC(Cl)=NC=2C(=O)N1CC1=CC=CC=C1 JLFFQICEMQMXPY-UHFFFAOYSA-N 0.000 description 1
- OZASLISSGAODKW-IBGZPJMESA-N 6-bromo-2-[4-[4-[(3s)-3-ethylmorpholin-4-yl]-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]anilino]-1h-pyrimidin-4-one Chemical compound CC[C@H]1COCCN1C1=NC(C=2C=CC(NC=3NC(=O)C=C(Br)N=3)=CC=2)=NC2=C1CCN(C=1N=CC=CN=1)C2 OZASLISSGAODKW-IBGZPJMESA-N 0.000 description 1
- ORIQLMBUPMABDV-UHFFFAOYSA-N 6-chloropyridine-3-carbonitrile Chemical compound ClC1=CC=C(C#N)C=N1 ORIQLMBUPMABDV-UHFFFAOYSA-N 0.000 description 1
- CTNDGYOJDNSZMQ-UHFFFAOYSA-N 7-benzyl-2,4-dichloro-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine Chemical compound C1C2=NC(Cl)=NC(Cl)=C2CCN1CC1=CC=CC=C1 CTNDGYOJDNSZMQ-UHFFFAOYSA-N 0.000 description 1
- OTYFBULLQUNSJI-IBGZPJMESA-N 7-ethyl-4-[(3s)-3-ethylmorpholin-4-yl]-2-[4-[(6-oxo-1h-pyridin-2-yl)amino]phenyl]-5,6-dihydropyrido[3,4-d]pyrimidin-8-one Chemical compound CC[C@H]1COCCN1C1=NC(C=2C=CC(NC=3NC(=O)C=CC=3)=CC=2)=NC2=C1CCN(CC)C2=O OTYFBULLQUNSJI-IBGZPJMESA-N 0.000 description 1
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
- VZRXGNMWNJILDB-UHFFFAOYSA-N 8H-pyrido[3,4-d]pyrimidine-7-carboxylic acid Chemical compound C1C2=NC=NC=C2C=CN1C(=O)O VZRXGNMWNJILDB-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- HPLNQCPCUACXLM-PGUFJCEWSA-N ABT-737 Chemical compound C([C@@H](CCN(C)C)NC=1C(=CC(=CC=1)S(=O)(=O)NC(=O)C=1C=CC(=CC=1)N1CCN(CC=2C(=CC=CC=2)C=2C=CC(Cl)=CC=2)CC1)[N+]([O-])=O)SC1=CC=CC=C1 HPLNQCPCUACXLM-PGUFJCEWSA-N 0.000 description 1
- BUROJSBIWGDYCN-GAUTUEMISA-N AP 23573 Chemical compound C1C[C@@H](OP(C)(C)=O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 BUROJSBIWGDYCN-GAUTUEMISA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 235000006491 Acacia senegal Nutrition 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 102000007469 Actins Human genes 0.000 description 1
- 108010085238 Actins Proteins 0.000 description 1
- YCIPQJTZJGUXND-UHFFFAOYSA-N Aglaia odorata Alkaloid Natural products C1=CC(OC)=CC=C1C1(C(C=2C(=O)N3CCCC3=NC=22)C=3C=CC=CC=3)C2(O)C2=C(OC)C=C(OC)C=C2O1 YCIPQJTZJGUXND-UHFFFAOYSA-N 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 206010061424 Anal cancer Diseases 0.000 description 1
- MXPOCMVWFLDDLZ-NSCUHMNNSA-N Apaziquone Chemical compound CN1C(\C=C\CO)=C(CO)C(C2=O)=C1C(=O)C=C2N1CC1 MXPOCMVWFLDDLZ-NSCUHMNNSA-N 0.000 description 1
- BFYIZQONLCFLEV-DAELLWKTSA-N Aromasine Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC(=C)C2=C1 BFYIZQONLCFLEV-DAELLWKTSA-N 0.000 description 1
- 108010024976 Asparaginase Proteins 0.000 description 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- 102000036365 BRCA1 Human genes 0.000 description 1
- 108700020463 BRCA1 Proteins 0.000 description 1
- 101150072950 BRCA1 gene Proteins 0.000 description 1
- 102000052609 BRCA2 Human genes 0.000 description 1
- 108700020462 BRCA2 Proteins 0.000 description 1
- WOVKYSAHUYNSMH-UHFFFAOYSA-N BROMODEOXYURIDINE Natural products C1C(O)C(CO)OC1N1C(=O)NC(=O)C(Br)=C1 WOVKYSAHUYNSMH-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 108010039209 Blood Coagulation Factors Proteins 0.000 description 1
- 102000015081 Blood Coagulation Factors Human genes 0.000 description 1
- 208000020084 Bone disease Diseases 0.000 description 1
- 201000006474 Brain Ischemia Diseases 0.000 description 1
- 101150008921 Brca2 gene Proteins 0.000 description 1
- 108010037003 Buserelin Proteins 0.000 description 1
- 239000004358 Butane-1, 3-diol Substances 0.000 description 1
- FVLVBPDQNARYJU-XAHDHGMMSA-N C[C@H]1CCC(CC1)NC(=O)N(CCCl)N=O Chemical compound C[C@H]1CCC(CC1)NC(=O)N(CCCl)N=O FVLVBPDQNARYJU-XAHDHGMMSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 1
- 206010007559 Cardiac failure congestive Diseases 0.000 description 1
- 206010007572 Cardiac hypertrophy Diseases 0.000 description 1
- 208000006029 Cardiomegaly Diseases 0.000 description 1
- 102000014914 Carrier Proteins Human genes 0.000 description 1
- 206010008120 Cerebral ischaemia Diseases 0.000 description 1
- JWBOIMRXGHLCPP-UHFFFAOYSA-N Chloditan Chemical compound C=1C=CC=C(Cl)C=1C(C(Cl)Cl)C1=CC=C(Cl)C=C1 JWBOIMRXGHLCPP-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- HVXBOLULGPECHP-WAYWQWQTSA-N Combretastatin A4 Chemical compound C1=C(O)C(OC)=CC=C1\C=C/C1=CC(OC)=C(OC)C(OC)=C1 HVXBOLULGPECHP-WAYWQWQTSA-N 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 229920002785 Croscarmellose sodium Polymers 0.000 description 1
- 108010024986 Cyclin-Dependent Kinase 2 Proteins 0.000 description 1
- 108010025464 Cyclin-Dependent Kinase 4 Proteins 0.000 description 1
- 102100036239 Cyclin-dependent kinase 2 Human genes 0.000 description 1
- 102100036252 Cyclin-dependent kinase 4 Human genes 0.000 description 1
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
- 201000003883 Cystic fibrosis Diseases 0.000 description 1
- 102000000311 Cytosine Deaminase Human genes 0.000 description 1
- 108010080611 Cytosine Deaminase Proteins 0.000 description 1
- AEMOLEFTQBMNLQ-YMDCURPLSA-N D-galactopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-YMDCURPLSA-N 0.000 description 1
- AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 description 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
- 229940123780 DNA topoisomerase I inhibitor Drugs 0.000 description 1
- 206010011968 Decreased immune responsiveness Diseases 0.000 description 1
- 206010012442 Dermatitis contact Diseases 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 206010061818 Disease progression Diseases 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 102400001368 Epidermal growth factor Human genes 0.000 description 1
- 101800003838 Epidermal growth factor Proteins 0.000 description 1
- HTIJFSOGRVMCQR-UHFFFAOYSA-N Epirubicin Natural products COc1cccc2C(=O)c3c(O)c4CC(O)(CC(OC5CC(N)C(=O)C(C)O5)c4c(O)c3C(=O)c12)C(=O)CO HTIJFSOGRVMCQR-UHFFFAOYSA-N 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- BFPYWIDHMRZLRN-SLHNCBLASA-N Ethinyl estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 BFPYWIDHMRZLRN-SLHNCBLASA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- RYECOJGRJDOGPP-UHFFFAOYSA-N Ethylurea Chemical compound CCNC(N)=O RYECOJGRJDOGPP-UHFFFAOYSA-N 0.000 description 1
- 108050000946 Eukaryotic translation initiation factor 4E-binding protein 1 Proteins 0.000 description 1
- 102100022466 Eukaryotic translation initiation factor 4E-binding protein 1 Human genes 0.000 description 1
- HKVAMNSJSFKALM-GKUWKFKPSA-N Everolimus Chemical compound C1C[C@@H](OCCO)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 HKVAMNSJSFKALM-GKUWKFKPSA-N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- VWUXBMIQPBEWFH-WCCTWKNTSA-N Fulvestrant Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3[C@H](CCCCCCCCCS(=O)CCCC(F)(F)C(F)(F)F)CC2=C1 VWUXBMIQPBEWFH-WCCTWKNTSA-N 0.000 description 1
- 206010017993 Gastrointestinal neoplasms Diseases 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- BLCLNMBMMGCOAS-URPVMXJPSA-N Goserelin Chemical compound C([C@@H](C(=O)N[C@H](COC(C)(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1[C@@H](CCC1)C(=O)NNC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 BLCLNMBMMGCOAS-URPVMXJPSA-N 0.000 description 1
- 108010069236 Goserelin Proteins 0.000 description 1
- 108010017080 Granulocyte Colony-Stimulating Factor Proteins 0.000 description 1
- 102000004269 Granulocyte Colony-Stimulating Factor Human genes 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 239000007821 HATU Substances 0.000 description 1
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 102100024025 Heparanase Human genes 0.000 description 1
- 206010019695 Hepatic neoplasm Diseases 0.000 description 1
- 206010019842 Hepatomegaly Diseases 0.000 description 1
- 208000017605 Hodgkin disease nodular sclerosis Diseases 0.000 description 1
- 208000021519 Hodgkin lymphoma Diseases 0.000 description 1
- 101000904173 Homo sapiens Progonadoliberin-1 Proteins 0.000 description 1
- 101000652747 Homo sapiens Target of rapamycin complex 2 subunit MAPKAP1 Proteins 0.000 description 1
- 208000023105 Huntington disease Diseases 0.000 description 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical class [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
- LCWXJXMHJVIJFK-UHFFFAOYSA-N Hydroxylysine Natural products NCC(O)CC(N)CC(O)=O LCWXJXMHJVIJFK-UHFFFAOYSA-N 0.000 description 1
- DOMWKUIIPQCAJU-LJHIYBGHSA-N Hydroxyprogesterone caproate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)CCCCC)[C@@]1(C)CC2 DOMWKUIIPQCAJU-LJHIYBGHSA-N 0.000 description 1
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 description 1
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- 208000029462 Immunodeficiency disease Diseases 0.000 description 1
- 108060003951 Immunoglobulin Proteins 0.000 description 1
- 108010016648 Immunophilins Proteins 0.000 description 1
- 102000000521 Immunophilins Human genes 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 108090000723 Insulin-Like Growth Factor I Proteins 0.000 description 1
- 102000014429 Insulin-like growth factor Human genes 0.000 description 1
- 102100037852 Insulin-like growth factor I Human genes 0.000 description 1
- 238000012695 Interfacial polymerization Methods 0.000 description 1
- 102000006992 Interferon-alpha Human genes 0.000 description 1
- 108010047761 Interferon-alpha Proteins 0.000 description 1
- 102000014150 Interferons Human genes 0.000 description 1
- 108010050904 Interferons Proteins 0.000 description 1
- 102000000588 Interleukin-2 Human genes 0.000 description 1
- 108010002350 Interleukin-2 Proteins 0.000 description 1
- 102000004388 Interleukin-4 Human genes 0.000 description 1
- 108090000978 Interleukin-4 Proteins 0.000 description 1
- 102000015696 Interleukins Human genes 0.000 description 1
- 108010063738 Interleukins Proteins 0.000 description 1
- 241000764238 Isis Species 0.000 description 1
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
- SNDPXSYFESPGGJ-BYPYZUCNSA-N L-2-aminopentanoic acid Chemical compound CCC[C@H](N)C(O)=O SNDPXSYFESPGGJ-BYPYZUCNSA-N 0.000 description 1
- ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 description 1
- 150000008575 L-amino acids Chemical class 0.000 description 1
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 1
- RHGKLRLOHDJJDR-BYPYZUCNSA-N L-citrulline Chemical compound NC(=O)NCCC[C@H]([NH3+])C([O-])=O RHGKLRLOHDJJDR-BYPYZUCNSA-N 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- FFFHZYDWPBMWHY-VKHMYHEASA-N L-homocysteine Chemical compound OC(=O)[C@@H](N)CCS FFFHZYDWPBMWHY-VKHMYHEASA-N 0.000 description 1
- UKAUYVFTDYCKQA-VKHMYHEASA-N L-homoserine Chemical compound OC(=O)[C@@H](N)CCO UKAUYVFTDYCKQA-VKHMYHEASA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- UCUNFLYVYCGDHP-BYPYZUCNSA-N L-methionine sulfone Chemical compound CS(=O)(=O)CC[C@H](N)C(O)=O UCUNFLYVYCGDHP-BYPYZUCNSA-N 0.000 description 1
- SNDPXSYFESPGGJ-UHFFFAOYSA-N L-norVal-OH Natural products CCCC(N)C(O)=O SNDPXSYFESPGGJ-UHFFFAOYSA-N 0.000 description 1
- DGYHPLMPMRKMPD-UHFFFAOYSA-N L-propargyl glycine Natural products OC(=O)C(N)CC#C DGYHPLMPMRKMPD-UHFFFAOYSA-N 0.000 description 1
- 239000005517 L01XE01 - Imatinib Substances 0.000 description 1
- 239000005411 L01XE02 - Gefitinib Substances 0.000 description 1
- 239000002136 L01XE07 - Lapatinib Substances 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 108010000817 Leuprolide Proteins 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229940124041 Luteinizing hormone releasing hormone (LHRH) antagonist Drugs 0.000 description 1
- 206010025323 Lymphomas Diseases 0.000 description 1
- 239000004907 Macro-emulsion Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 208000002720 Malnutrition Diseases 0.000 description 1
- 208000025205 Mantle-Cell Lymphoma Diseases 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- 206010048723 Multiple-drug resistance Diseases 0.000 description 1
- 101100087591 Mus musculus Rictor gene Proteins 0.000 description 1
- HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 1
- JDHILDINMRGULE-LURJTMIESA-N N(pros)-methyl-L-histidine Chemical compound CN1C=NC=C1C[C@H](N)C(O)=O JDHILDINMRGULE-LURJTMIESA-N 0.000 description 1
- FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical class CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
- GDFAOVXKHJXLEI-VKHMYHEASA-N N-methyl-L-alanine Chemical compound C[NH2+][C@@H](C)C([O-])=O GDFAOVXKHJXLEI-VKHMYHEASA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- RHGKLRLOHDJJDR-UHFFFAOYSA-N Ndelta-carbamoyl-DL-ornithine Natural products OC(=O)C(N)CCCNC(N)=O RHGKLRLOHDJJDR-UHFFFAOYSA-N 0.000 description 1
- 206010029350 Neurotoxicity Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 102000004459 Nitroreductase Human genes 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- 229910003849 O-Si Inorganic materials 0.000 description 1
- BZQFBWGGLXLEPQ-UHFFFAOYSA-N O-phosphoryl-L-serine Natural products OC(=O)C(N)COP(O)(O)=O BZQFBWGGLXLEPQ-UHFFFAOYSA-N 0.000 description 1
- IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 229910003872 O—Si Inorganic materials 0.000 description 1
- 102000014160 PTEN Phosphohydrolase Human genes 0.000 description 1
- 108010011536 PTEN Phosphohydrolase Proteins 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 description 1
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 1
- 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 1
- 102000010780 Platelet-Derived Growth Factor Human genes 0.000 description 1
- 108010038512 Platelet-Derived Growth Factor Proteins 0.000 description 1
- 108030005449 Polo kinases Proteins 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920002556 Polyethylene Glycol 300 Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical class C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 1
- 102100024028 Progonadoliberin-1 Human genes 0.000 description 1
- 101710124303 Proline-rich protein 5 Proteins 0.000 description 1
- 102100034733 Proline-rich protein 5 Human genes 0.000 description 1
- 229940079156 Proteasome inhibitor Drugs 0.000 description 1
- 102000001253 Protein Kinase Human genes 0.000 description 1
- 108010090931 Proto-Oncogene Proteins c-bcl-2 Proteins 0.000 description 1
- 102000013535 Proto-Oncogene Proteins c-bcl-2 Human genes 0.000 description 1
- 102000016971 Proto-Oncogene Proteins c-kit Human genes 0.000 description 1
- 108010014608 Proto-Oncogene Proteins c-kit Proteins 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 108010029031 Regulatory-Associated Protein of mTOR Proteins 0.000 description 1
- 102100040969 Regulatory-associated protein of mTOR Human genes 0.000 description 1
- 108010034782 Ribosomal Protein S6 Kinases Proteins 0.000 description 1
- 102000009738 Ribosomal Protein S6 Kinases Human genes 0.000 description 1
- 102100024908 Ribosomal protein S6 kinase beta-1 Human genes 0.000 description 1
- 101710108924 Ribosomal protein S6 kinase beta-1 Proteins 0.000 description 1
- 102100024917 Ribosomal protein S6 kinase beta-2 Human genes 0.000 description 1
- 101710108923 Ribosomal protein S6 kinase beta-2 Proteins 0.000 description 1
- 102000001332 SRC Human genes 0.000 description 1
- 108060006706 SRC Proteins 0.000 description 1
- 206010061934 Salivary gland cancer Diseases 0.000 description 1
- 108010077895 Sarcosine Proteins 0.000 description 1
- 108010071390 Serum Albumin Proteins 0.000 description 1
- 102000007562 Serum Albumin Human genes 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 206010041067 Small cell lung cancer Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 101000996723 Sus scrofa Gonadotropin-releasing hormone receptor Proteins 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 230000006044 T cell activation Effects 0.000 description 1
- 102100030904 Target of rapamycin complex 2 subunit MAPKAP1 Human genes 0.000 description 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 description 1
- BPEGJWRSRHCHSN-UHFFFAOYSA-N Temozolomide Chemical compound O=C1N(C)N=NC2=C(C(N)=O)N=CN21 BPEGJWRSRHCHSN-UHFFFAOYSA-N 0.000 description 1
- CBPNZQVSJQDFBE-FUXHJELOSA-N Temsirolimus Chemical compound C1C[C@@H](OC(=O)C(C)(CO)CO)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 CBPNZQVSJQDFBE-FUXHJELOSA-N 0.000 description 1
- PDMMFKSKQVNJMI-BLQWBTBKSA-N Testosterone propionate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CC)[C@@]1(C)CC2 PDMMFKSKQVNJMI-BLQWBTBKSA-N 0.000 description 1
- 108090000190 Thrombin Proteins 0.000 description 1
- 102000006601 Thymidine Kinase Human genes 0.000 description 1
- 108020004440 Thymidine kinase Proteins 0.000 description 1
- IVTVGDXNLFLDRM-HNNXBMFYSA-N Tomudex Chemical compound C=1C=C2NC(C)=NC(=O)C2=CC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)S1 IVTVGDXNLFLDRM-HNNXBMFYSA-N 0.000 description 1
- 239000000365 Topoisomerase I Inhibitor Substances 0.000 description 1
- 206010044221 Toxic encephalopathy Diseases 0.000 description 1
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 206010053613 Type IV hypersensitivity reaction Diseases 0.000 description 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 1
- 208000008385 Urogenital Neoplasms Diseases 0.000 description 1
- 102000004504 Urokinase Plasminogen Activator Receptors Human genes 0.000 description 1
- 108010042352 Urokinase Plasminogen Activator Receptors Proteins 0.000 description 1
- 206010047741 Vulval cancer Diseases 0.000 description 1
- 208000004354 Vulvar Neoplasms Diseases 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 1
- IWTYTFSSTWXZFU-QPJJXVBHSA-N [(e)-3-chloroprop-1-enyl]benzene Chemical compound ClC\C=C\C1=CC=CC=C1 IWTYTFSSTWXZFU-QPJJXVBHSA-N 0.000 description 1
- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 description 1
- ZYDJSVLXMTWCEH-UHFFFAOYSA-N [4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]urea Chemical compound C1=CC(NC(=O)N)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CC=CN=1)C2 ZYDJSVLXMTWCEH-UHFFFAOYSA-N 0.000 description 1
- LVELZUANKBQOPX-HNNXBMFYSA-N [4-[4-[(3s)-3-methylmorpholin-4-yl]-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(N)=O)=CC=2)=NC2=C1CCN(C=1N=CC=CN=1)C2 LVELZUANKBQOPX-HNNXBMFYSA-N 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000008351 acetate buffer Substances 0.000 description 1
- VJHCJDRQFCCTHL-UHFFFAOYSA-N acetic acid 2,3,4,5,6-pentahydroxyhexanal Chemical compound CC(O)=O.OCC(O)C(O)C(O)C(O)C=O VJHCJDRQFCCTHL-UHFFFAOYSA-N 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000005042 acyloxymethyl group Chemical group 0.000 description 1
- 210000004404 adrenal cortex Anatomy 0.000 description 1
- 229940009456 adriamycin Drugs 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005206 alkoxycarbonyloxymethyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000005237 alkyleneamino group Chemical group 0.000 description 1
- 125000005238 alkylenediamino group Chemical group 0.000 description 1
- 125000005530 alkylenedioxy group Chemical group 0.000 description 1
- 125000005529 alkyleneoxy group Chemical group 0.000 description 1
- 125000004419 alkynylene group Chemical group 0.000 description 1
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical class OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 229960003437 aminoglutethimide Drugs 0.000 description 1
- ROBVIMPUHSLWNV-UHFFFAOYSA-N aminoglutethimide Chemical compound C=1C=C(N)C=CC=1C1(CC)CCC(=O)NC1=O ROBVIMPUHSLWNV-UHFFFAOYSA-N 0.000 description 1
- 229960001220 amsacrine Drugs 0.000 description 1
- XCPGHVQEEXUHNC-UHFFFAOYSA-N amsacrine Chemical compound COC1=CC(NS(C)(=O)=O)=CC=C1NC1=C(C=CC=C2)C2=NC2=CC=CC=C12 XCPGHVQEEXUHNC-UHFFFAOYSA-N 0.000 description 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 1
- 201000007538 anal carcinoma Diseases 0.000 description 1
- 229960002932 anastrozole Drugs 0.000 description 1
- YBBLVLTVTVSKRW-UHFFFAOYSA-N anastrozole Chemical compound N#CC(C)(C)C1=CC(C(C)(C#N)C)=CC(CN2N=CN=C2)=C1 YBBLVLTVTVSKRW-UHFFFAOYSA-N 0.000 description 1
- 239000003098 androgen Substances 0.000 description 1
- 229940030486 androgens Drugs 0.000 description 1
- RGHILYZRVFRRNK-UHFFFAOYSA-N anthracene-1,2-dione Chemical group C1=CC=C2C=C(C(C(=O)C=C3)=O)C3=CC2=C1 RGHILYZRVFRRNK-UHFFFAOYSA-N 0.000 description 1
- 229940045799 anthracyclines and related substance Drugs 0.000 description 1
- 230000003432 anti-folate effect Effects 0.000 description 1
- 230000003302 anti-idiotype Effects 0.000 description 1
- 230000001399 anti-metabolic effect Effects 0.000 description 1
- 230000000340 anti-metabolite Effects 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 229940127074 antifolate Drugs 0.000 description 1
- 229940100197 antimetabolite Drugs 0.000 description 1
- 239000002256 antimetabolite Substances 0.000 description 1
- 229940045687 antimetabolites folic acid analogs Drugs 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 229960003121 arginine Drugs 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000003886 aromatase inhibitor Substances 0.000 description 1
- 229940046844 aromatase inhibitors Drugs 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 125000005251 aryl acyl group Chemical group 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 235000009582 asparagine Nutrition 0.000 description 1
- 229960001230 asparagine Drugs 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 239000003719 aurora kinase inhibitor Substances 0.000 description 1
- 229940120638 avastin Drugs 0.000 description 1
- 229960002756 azacitidine Drugs 0.000 description 1
- LMEKQMALGUDUQG-UHFFFAOYSA-N azathioprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC=NC2=C1NC=N2 LMEKQMALGUDUQG-UHFFFAOYSA-N 0.000 description 1
- 229960002170 azathioprine Drugs 0.000 description 1
- 125000002393 azetidinyl group Chemical group 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000000022 bacteriostatic agent Substances 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229960000686 benzalkonium chloride Drugs 0.000 description 1
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- SEHICTXEIZXZEK-UHFFFAOYSA-N benzyl 2-[4-(ethylcarbamoylamino)phenyl]-4-(1,4-oxazepan-4-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCCC2)=NC2=C1CCN(C(=O)OCC=1C=CC=CC=1)C2 SEHICTXEIZXZEK-UHFFFAOYSA-N 0.000 description 1
- UZZUDLNECVNYKF-UHFFFAOYSA-N benzyl 2-[4-(ethylcarbamoylamino)phenyl]-4-morpholin-4-yl-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(C(=O)OCC=1C=CC=CC=1)C2 UZZUDLNECVNYKF-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 229940000635 beta-alanine Drugs 0.000 description 1
- AGSPXMVUFBBBMO-UHFFFAOYSA-N beta-aminopropionitrile Chemical compound NCCC#N AGSPXMVUFBBBMO-UHFFFAOYSA-N 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 229960000997 bicalutamide Drugs 0.000 description 1
- GPRLTFBKWDERLU-UHFFFAOYSA-N bicyclo[2.2.2]octane Chemical compound C1CC2CCC1CC2 GPRLTFBKWDERLU-UHFFFAOYSA-N 0.000 description 1
- 108091008324 binding proteins Proteins 0.000 description 1
- 238000002306 biochemical method Methods 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000008512 biological response Effects 0.000 description 1
- 239000012472 biological sample Substances 0.000 description 1
- 239000004305 biphenyl Chemical group 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- HUTDDBSSHVOYJR-UHFFFAOYSA-H bis[(2-oxo-1,3,2$l^{5},4$l^{2}-dioxaphosphaplumbetan-2-yl)oxy]lead Chemical compound [Pb+2].[Pb+2].[Pb+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O HUTDDBSSHVOYJR-UHFFFAOYSA-H 0.000 description 1
- 201000000053 blastoma Diseases 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 239000003114 blood coagulation factor Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- BGECDVWSWDRFSP-UHFFFAOYSA-N borazine Chemical compound B1NBNBN1 BGECDVWSWDRFSP-UHFFFAOYSA-N 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- GXJABQQUPOEUTA-RDJZCZTQSA-N bortezomib Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)B(O)O)NC(=O)C=1N=CC=NC=1)C1=CC=CC=C1 GXJABQQUPOEUTA-RDJZCZTQSA-N 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 201000000220 brain stem cancer Diseases 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229950004398 broxuridine Drugs 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- CUWODFFVMXJOKD-UVLQAERKSA-N buserelin Chemical compound CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](COC(C)(C)C)NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H]1NC(=O)CC1)CC1=CC=C(O)C=C1 CUWODFFVMXJOKD-UVLQAERKSA-N 0.000 description 1
- 229960002719 buserelin Drugs 0.000 description 1
- 229960002092 busulfan Drugs 0.000 description 1
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N butyl alcohol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 229960001948 caffeine Drugs 0.000 description 1
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 229950002826 canertinib Drugs 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- UHBYWPGGCSDKFX-UHFFFAOYSA-N carboxyglutamic acid Chemical compound OC(=O)C(N)CC(C(O)=O)C(O)=O UHBYWPGGCSDKFX-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 229960005243 carmustine Drugs 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000030833 cell death Effects 0.000 description 1
- 230000003915 cell function Effects 0.000 description 1
- 230000004637 cellular stress Effects 0.000 description 1
- 208000015114 central nervous system disease Diseases 0.000 description 1
- 206010008118 cerebral infarction Diseases 0.000 description 1
- 229940082500 cetostearyl alcohol Drugs 0.000 description 1
- 229960005395 cetuximab Drugs 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000010568 chiral column chromatography Methods 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- QOPVNWQGBQYBBP-UHFFFAOYSA-N chloroethyl chloroformate Chemical compound CC(Cl)OC(Cl)=O QOPVNWQGBQYBBP-UHFFFAOYSA-N 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 210000000349 chromosome Anatomy 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
- 229960002173 citrulline Drugs 0.000 description 1
- 235000013477 citrulline Nutrition 0.000 description 1
- 229960002436 cladribine Drugs 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000011260 co-administration Methods 0.000 description 1
- 238000005354 coacervation Methods 0.000 description 1
- 229960002271 cobimetinib Drugs 0.000 description 1
- BSMCAPRUBJMWDF-KRWDZBQOSA-N cobimetinib Chemical compound C1C(O)([C@H]2NCCCC2)CN1C(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F BSMCAPRUBJMWDF-KRWDZBQOSA-N 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 229940046044 combinations of antineoplastic agent Drugs 0.000 description 1
- 229960005537 combretastatin A-4 Drugs 0.000 description 1
- HVXBOLULGPECHP-UHFFFAOYSA-N combretastatin A4 Natural products C1=C(O)C(OC)=CC=C1C=CC1=CC(OC)=C(OC)C(OC)=C1 HVXBOLULGPECHP-UHFFFAOYSA-N 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 208000010247 contact dermatitis Diseases 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000012084 conversion product Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 229960005168 croscarmellose Drugs 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000001767 crosslinked sodium carboxy methyl cellulose Substances 0.000 description 1
- 239000002875 cyclin dependent kinase inhibitor Substances 0.000 description 1
- 229940043378 cyclin-dependent kinase inhibitor Drugs 0.000 description 1
- KZZKOVLJUKWSKX-UHFFFAOYSA-N cyclobutanamine Chemical compound NC1CCC1 KZZKOVLJUKWSKX-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- PFWWSGFPICCWGU-UHFFFAOYSA-N cyclopropanesulfonyl chloride Chemical compound ClS(=O)(=O)C1CC1 PFWWSGFPICCWGU-UHFFFAOYSA-N 0.000 description 1
- UWFYSQMTEOIJJG-FDTZYFLXSA-N cyproterone acetate Chemical compound C1=C(Cl)C2=CC(=O)[C@@H]3C[C@@H]3[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 UWFYSQMTEOIJJG-FDTZYFLXSA-N 0.000 description 1
- 229960000978 cyproterone acetate Drugs 0.000 description 1
- 208000031513 cyst Diseases 0.000 description 1
- 229960000684 cytarabine Drugs 0.000 description 1
- 230000003436 cytoskeletal effect Effects 0.000 description 1
- 230000001086 cytosolic effect Effects 0.000 description 1
- 239000000824 cytostatic agent Substances 0.000 description 1
- 230000001085 cytostatic effect Effects 0.000 description 1
- 229960003901 dacarbazine Drugs 0.000 description 1
- 229960000975 daunorubicin Drugs 0.000 description 1
- 230000006240 deamidation Effects 0.000 description 1
- 238000007257 deesterification reaction Methods 0.000 description 1
- 239000003405 delayed action preparation Substances 0.000 description 1
- YSMODUONRAFBET-UHFFFAOYSA-N delta-DL-hydroxylysine Natural products NCC(O)CCC(N)C(O)=O YSMODUONRAFBET-UHFFFAOYSA-N 0.000 description 1
- 210000004443 dendritic cell Anatomy 0.000 description 1
- CFCUWKMKBJTWLW-UHFFFAOYSA-N deoliosyl-3C-alpha-L-digitoxosyl-MTM Natural products CC=1C(O)=C2C(O)=C3C(=O)C(OC4OC(C)C(O)C(OC5OC(C)C(O)C(OC6OC(C)C(O)C(C)(O)C6)C5)C4)C(C(OC)C(=O)C(O)C(C)O)CC3=CC2=CC=1OC(OC(C)C1O)CC1OC1CC(O)C(O)C(C)O1 CFCUWKMKBJTWLW-UHFFFAOYSA-N 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 231100000223 dermal penetration Toxicity 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
- 229960003957 dexamethasone Drugs 0.000 description 1
- 229950006137 dexfosfoserine Drugs 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- RGLYKWWBQGJZGM-ISLYRVAYSA-N diethylstilbestrol Chemical compound C=1C=C(O)C=CC=1C(/CC)=C(\CC)C1=CC=C(O)C=C1 RGLYKWWBQGJZGM-ISLYRVAYSA-N 0.000 description 1
- 229960000452 diethylstilbestrol Drugs 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 125000005879 dioxolanyl group Chemical group 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 230000005750 disease progression Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 description 1
- 239000003534 dna topoisomerase inhibitor Substances 0.000 description 1
- 229960003668 docetaxel Drugs 0.000 description 1
- 229960004679 doxorubicin Drugs 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 238000009510 drug design Methods 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 230000036267 drug metabolism Effects 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
- 229940121647 egfr inhibitor Drugs 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000012039 electrophile Substances 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 201000008184 embryoma Diseases 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000008387 emulsifying waxe Substances 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- 230000002357 endometrial effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 229940116977 epidermal growth factor Drugs 0.000 description 1
- 102000052116 epidermal growth factor receptor activity proteins Human genes 0.000 description 1
- 108700015053 epidermal growth factor receptor activity proteins Proteins 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- YJGVMLPVUAXIQN-UHFFFAOYSA-N epipodophyllotoxin Natural products COC1=C(OC)C(OC)=CC(C2C3=CC=4OCOC=4C=C3C(O)C3C2C(OC3)=O)=C1 YJGVMLPVUAXIQN-UHFFFAOYSA-N 0.000 description 1
- 229960001904 epirubicin Drugs 0.000 description 1
- 229940082789 erbitux Drugs 0.000 description 1
- YSMODUONRAFBET-UHNVWZDZSA-N erythro-5-hydroxy-L-lysine Chemical compound NC[C@H](O)CC[C@H](N)C(O)=O YSMODUONRAFBET-UHNVWZDZSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- WCDWBPCFGJXFJZ-UHFFFAOYSA-N etanidazole Chemical compound OCCNC(=O)CN1C=CN=C1[N+]([O-])=O WCDWBPCFGJXFJZ-UHFFFAOYSA-N 0.000 description 1
- XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 1
- OKDGDBRZMJNKLV-UHFFFAOYSA-M ethenyl(diphenyl)sulfanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C=1C=CC=CC=1[S+](C=C)C1=CC=CC=C1 OKDGDBRZMJNKLV-UHFFFAOYSA-M 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229960002568 ethinylestradiol Drugs 0.000 description 1
- LJQQOJOCWYMZEW-UHFFFAOYSA-N ethyl 1-[(4-methoxyphenyl)methyl]-4,5-dioxopyrrolidine-3-carboxylate Chemical compound O=C1C(=O)C(C(=O)OCC)CN1CC1=CC=C(OC)C=C1 LJQQOJOCWYMZEW-UHFFFAOYSA-N 0.000 description 1
- NYPGUSWHIXFWSI-INIZCTEOSA-N ethyl 2-[4-(ethylcarbamoylamino)phenyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)OCC)C2 NYPGUSWHIXFWSI-INIZCTEOSA-N 0.000 description 1
- YXDXSBLZVORMOH-UHFFFAOYSA-N ethyl 2-[4-(ethylcarbamoylamino)phenyl]-4-morpholin-4-yl-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(C(=O)OCC)C2 YXDXSBLZVORMOH-UHFFFAOYSA-N 0.000 description 1
- HCTJHQFFNDLDPF-UHFFFAOYSA-N ethyl 3-(benzylamino)propanoate Chemical compound CCOC(=O)CCNCC1=CC=CC=C1 HCTJHQFFNDLDPF-UHFFFAOYSA-N 0.000 description 1
- RPGUZVBNBVXTFL-UHFFFAOYSA-N ethyl 4-amino-1-benzyl-5-oxo-2h-pyrrole-3-carboxylate Chemical compound C1C(C(=O)OCC)=C(N)C(=O)N1CC1=CC=CC=C1 RPGUZVBNBVXTFL-UHFFFAOYSA-N 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 102000022577 eukaryotic initiation factor 4E binding proteins Human genes 0.000 description 1
- 108091012329 eukaryotic initiation factor 4E binding proteins Proteins 0.000 description 1
- 229960005167 everolimus Drugs 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 229960000255 exemestane Drugs 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- DBEPLOCGEIEOCV-WSBQPABSSA-N finasteride Chemical compound N([C@@H]1CC2)C(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)NC(C)(C)C)[C@@]2(C)CC1 DBEPLOCGEIEOCV-WSBQPABSSA-N 0.000 description 1
- 229960004039 finasteride Drugs 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- ODKNJVUHOIMIIZ-RRKCRQDMSA-N floxuridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(F)=C1 ODKNJVUHOIMIIZ-RRKCRQDMSA-N 0.000 description 1
- 229960000390 fludarabine Drugs 0.000 description 1
- 229960005304 fludarabine phosphate Drugs 0.000 description 1
- YLRFCQOZQXIBAB-RBZZARIASA-N fluoxymesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)C[C@@H]2O YLRFCQOZQXIBAB-RBZZARIASA-N 0.000 description 1
- 229960001751 fluoxymesterone Drugs 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000004052 folic acid antagonist Substances 0.000 description 1
- 150000002224 folic acids Chemical class 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229960002258 fulvestrant Drugs 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 229960002584 gefitinib Drugs 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 238000010914 gene-directed enzyme pro-drug therapy Methods 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229940097043 glucuronic acid Drugs 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 229940074045 glyceryl distearate Drugs 0.000 description 1
- 125000003147 glycosyl group Chemical group 0.000 description 1
- XLXSAKCOAKORKW-AQJXLSMYSA-N gonadorelin Chemical class C([C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)NCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 XLXSAKCOAKORKW-AQJXLSMYSA-N 0.000 description 1
- XLXSAKCOAKORKW-UHFFFAOYSA-N gonadorelin Chemical compound C1CCC(C(=O)NCC(N)=O)N1C(=O)C(CCCN=C(N)N)NC(=O)C(CC(C)C)NC(=O)CNC(=O)C(NC(=O)C(CO)NC(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C(CC=1NC=NC=1)NC(=O)C1NC(=O)CC1)CC1=CC=C(O)C=C1 XLXSAKCOAKORKW-UHFFFAOYSA-N 0.000 description 1
- 229960002913 goserelin Drugs 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 229960000789 guanidine hydrochloride Drugs 0.000 description 1
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 1
- 210000002768 hair cell Anatomy 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 201000010536 head and neck cancer Diseases 0.000 description 1
- 208000014829 head and neck neoplasm Diseases 0.000 description 1
- 150000002373 hemiacetals Chemical group 0.000 description 1
- 108010037536 heparanase Proteins 0.000 description 1
- 229940022353 herceptin Drugs 0.000 description 1
- UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 229940091173 hydantoin Drugs 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- MSYBLBLAMDYKKZ-UHFFFAOYSA-N hydron;pyridine-3-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=CN=C1 MSYBLBLAMDYKKZ-UHFFFAOYSA-N 0.000 description 1
- 239000008309 hydrophilic cream Substances 0.000 description 1
- 229920001477 hydrophilic polymer Polymers 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 229920001600 hydrophobic polymer Polymers 0.000 description 1
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- QJHBJHUKURJDLG-UHFFFAOYSA-N hydroxy-L-lysine Natural products NCCCCC(NO)C(O)=O QJHBJHUKURJDLG-UHFFFAOYSA-N 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
- 229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
- 229950000801 hydroxyprogesterone caproate Drugs 0.000 description 1
- 229960002591 hydroxyproline Drugs 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 description 1
- 229960001101 ifosfamide Drugs 0.000 description 1
- 238000005417 image-selected in vivo spectroscopy Methods 0.000 description 1
- KTUFNOKKBVMGRW-UHFFFAOYSA-N imatinib Chemical compound C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 KTUFNOKKBVMGRW-UHFFFAOYSA-N 0.000 description 1
- 229960002411 imatinib Drugs 0.000 description 1
- 210000002865 immune cell Anatomy 0.000 description 1
- 208000026278 immune system disease Diseases 0.000 description 1
- 230000005847 immunogenicity Effects 0.000 description 1
- 102000018358 immunoglobulin Human genes 0.000 description 1
- 229940072221 immunoglobulins Drugs 0.000 description 1
- 238000002650 immunosuppressive therapy Methods 0.000 description 1
- 238000009169 immunotherapy Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000012739 integrated shape imaging system Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229940079322 interferon Drugs 0.000 description 1
- 229940028885 interleukin-4 Drugs 0.000 description 1
- 229940047122 interleukins Drugs 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- 230000031146 intracellular signal transduction Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229960004768 irinotecan Drugs 0.000 description 1
- GURKHSYORGJETM-WAQYZQTGSA-N irinotecan hydrochloride (anhydrous) Chemical compound Cl.C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 GURKHSYORGJETM-WAQYZQTGSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229960004891 lapatinib Drugs 0.000 description 1
- BCFGMOOMADDAQU-UHFFFAOYSA-N lapatinib Chemical compound O1C(CNCCS(=O)(=O)C)=CC=C1C1=CC=C(N=CN=C2NC=3C=C(Cl)C(OCC=4C=C(F)C=CC=4)=CC=3)C2=C1 BCFGMOOMADDAQU-UHFFFAOYSA-N 0.000 description 1
- 229940046892 lead acetate Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 229960003881 letrozole Drugs 0.000 description 1
- HPJKCIUCZWXJDR-UHFFFAOYSA-N letrozole Chemical compound C1=CC(C#N)=CC=C1C(N1N=CN=C1)C1=CC=C(C#N)C=C1 HPJKCIUCZWXJDR-UHFFFAOYSA-N 0.000 description 1
- 229960004338 leuprorelin Drugs 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 201000007270 liver cancer Diseases 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 201000005296 lung carcinoma Diseases 0.000 description 1
- 201000005243 lung squamous cell carcinoma Diseases 0.000 description 1
- 239000012931 lyophilized formulation Substances 0.000 description 1
- 239000008176 lyophilized powder Substances 0.000 description 1
- 229940123729 mTOR kinase inhibitor Drugs 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000036210 malignancy Effects 0.000 description 1
- 230000001071 malnutrition Effects 0.000 description 1
- 235000000824 malnutrition Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 229950008959 marimastat Drugs 0.000 description 1
- OCSMOTCMPXTDND-OUAUKWLOSA-N marimastat Chemical compound CNC(=O)[C@H](C(C)(C)C)NC(=O)[C@H](CC(C)C)[C@H](O)C(=O)NO OCSMOTCMPXTDND-OUAUKWLOSA-N 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229960001428 mercaptopurine Drugs 0.000 description 1
- 108020004999 messenger RNA Proteins 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 239000003475 metalloproteinase inhibitor Substances 0.000 description 1
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 1
- 230000009401 metastasis Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- ZBQNYNWPYXTUTB-UHFFFAOYSA-N methyl 1-benzyl-3-oxopiperidine-4-carboxylate Chemical compound C1C(=O)C(C(=O)OC)CCN1CC1=CC=CC=C1 ZBQNYNWPYXTUTB-UHFFFAOYSA-N 0.000 description 1
- PHTILULPLFUXPS-UHFFFAOYSA-N methyl 1-benzyl-4-oxopiperidine-3-carboxylate Chemical compound C1CC(=O)C(C(=O)OC)CN1CC1=CC=CC=C1 PHTILULPLFUXPS-UHFFFAOYSA-N 0.000 description 1
- WRRJUFVIUJAMNQ-UHFFFAOYSA-N methyl 2-[2-[4-(ethylcarbamoylamino)phenyl]-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-6-methylpyrimidine-4-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=C(C=C(C)N=1)C(=O)OC)C2 WRRJUFVIUJAMNQ-UHFFFAOYSA-N 0.000 description 1
- WUPUGZHGSRLBDH-HNNXBMFYSA-N methyl 2-[4-(ethylcarbamoylamino)phenyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)OC)C2 WUPUGZHGSRLBDH-HNNXBMFYSA-N 0.000 description 1
- GAIJXTJKNCULPJ-UHFFFAOYSA-N methyl 2-[4-(ethylcarbamoylamino)phenyl]-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)OC)C2 GAIJXTJKNCULPJ-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 229960002900 methylcellulose Drugs 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 229960000282 metronidazole Drugs 0.000 description 1
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229960000350 mitotane Drugs 0.000 description 1
- 239000007932 molded tablet Substances 0.000 description 1
- 125000006682 monohaloalkyl group Chemical group 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- XMWFMEYDRNJSOO-UHFFFAOYSA-N morpholine-4-carbonyl chloride Chemical compound ClC(=O)N1CCOCC1 XMWFMEYDRNJSOO-UHFFFAOYSA-N 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 229940043348 myristyl alcohol Drugs 0.000 description 1
- YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 description 1
- ANGKVUVZQVUVJO-UHFFFAOYSA-N n-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1B1OC(C)(C)C(C)(C)O1 ANGKVUVZQVUVJO-UHFFFAOYSA-N 0.000 description 1
- ZKKBJFMUPDPRCD-UHFFFAOYSA-N n-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]-1h-benzimidazol-2-amine Chemical compound C1COCCN1C1=NC(C=2C=CC(NC=3NC4=CC=CC=C4N=3)=CC=2)=NC2=C1CCN(C=1N=CC=CN=1)C2 ZKKBJFMUPDPRCD-UHFFFAOYSA-N 0.000 description 1
- UTDZRCFNFNIRSH-UHFFFAOYSA-N n-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]-1h-imidazol-2-amine Chemical compound C1COCCN1C1=NC(C=2C=CC(NC=3NC=CN=3)=CC=2)=NC2=C1CCN(C=1N=CC=CN=1)C2 UTDZRCFNFNIRSH-UHFFFAOYSA-N 0.000 description 1
- DKLNXNDBZAPKFH-UHFFFAOYSA-N n-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]pyrimidin-2-amine Chemical compound C1COCCN1C1=NC(C=2C=CC(NC=3N=CC=CN=3)=CC=2)=NC2=C1CCN(C=1N=CC=CN=1)C2 DKLNXNDBZAPKFH-UHFFFAOYSA-N 0.000 description 1
- SJCMKJKKCPWFAT-UHFFFAOYSA-N n-[4-(6-benzyl-4-morpholin-4-yl-7-oxo-5h-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(CC=1C=CC=CC=1)C2=O SJCMKJKKCPWFAT-UHFFFAOYSA-N 0.000 description 1
- UNCGTOKZRYUGQM-INIZCTEOSA-N n-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(oxetan-3-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-1h-imidazol-2-amine Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC=3NC=CN=3)=CC=2)=NC2=C1CCN(C1COC1)C2 UNCGTOKZRYUGQM-INIZCTEOSA-N 0.000 description 1
- WRAOGADMPFBEHY-KRWDZBQOSA-N n-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-propan-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-1h-imidazol-2-amine Chemical compound C1N(C(C)C)CCC2=C1N=C(C=1C=CC(NC=3NC=CN=3)=CC=1)N=C2N1CCOC[C@@H]1C WRAOGADMPFBEHY-KRWDZBQOSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- NQBKFULMFQMZBE-UHFFFAOYSA-N n-bz-3-benzanthronylpyrazolanthron Chemical compound C12=CC=CC(C(=O)C=3C4=CC=CC=3)=C2C4=NN1C1=CC=C2C3=C1C1=CC=CC=C1C(=O)C3=CC=C2 NQBKFULMFQMZBE-UHFFFAOYSA-N 0.000 description 1
- DGSJRYABRBQXGS-UHFFFAOYSA-N n-ethyl-2-[4-(ethylcarbamoylamino)phenyl]-4-morpholin-4-yl-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxamide Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(C(=O)NCC)C2 DGSJRYABRBQXGS-UHFFFAOYSA-N 0.000 description 1
- LSONTHVZQIRIRG-KRWDZBQOSA-N n-ethyl-4-[(3s)-3-methylmorpholin-4-yl]-2-[4-[(6-oxo-1h-pyridin-2-yl)amino]phenyl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxamide Chemical compound C1N(C(=O)NCC)CCC2=C1N=C(C=1C=CC(NC=3NC(=O)C=CC=3)=CC=1)N=C2N1CCOC[C@@H]1C LSONTHVZQIRIRG-KRWDZBQOSA-N 0.000 description 1
- FAKIMRZNVHJHAT-UHFFFAOYSA-N n-ethyl-6-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)-1h-benzimidazol-2-amine Chemical compound C=1C=C2NC(NCC)=NC2=CC=1C(N=1)=NC=2CN(C=3N=CC=CN=3)CCC=2C=1N1CCOCC1 FAKIMRZNVHJHAT-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002088 nanocapsule Substances 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- JLYAXFNOILIKPP-KXQOOQHDSA-N navitoclax Chemical compound C([C@@H](NC1=CC=C(C=C1S(=O)(=O)C(F)(F)F)S(=O)(=O)NC(=O)C1=CC=C(C=C1)N1CCN(CC1)CC1=C(CCC(C1)(C)C)C=1C=CC(Cl)=CC=1)CSC=1C=CC=CC=1)CN1CCOCC1 JLYAXFNOILIKPP-KXQOOQHDSA-N 0.000 description 1
- 229950004847 navitoclax Drugs 0.000 description 1
- 230000007135 neurotoxicity Effects 0.000 description 1
- 231100000228 neurotoxicity Toxicity 0.000 description 1
- XWXYUMMDTVBTOU-UHFFFAOYSA-N nilutamide Chemical compound O=C1C(C)(C)NC(=O)N1C1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 XWXYUMMDTVBTOU-UHFFFAOYSA-N 0.000 description 1
- 229960002653 nilutamide Drugs 0.000 description 1
- MDJFHRLTPRPZLY-UHFFFAOYSA-N nimorazole Chemical compound [O-][N+](=O)C1=CN=CN1CCN1CCOCC1 MDJFHRLTPRPZLY-UHFFFAOYSA-N 0.000 description 1
- 229960004918 nimorazole Drugs 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 108020001162 nitroreductase Proteins 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000003956 nonsteroidal anti androgen Substances 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 208000015380 nutritional deficiency disease Diseases 0.000 description 1
- GYCKQBWUSACYIF-UHFFFAOYSA-N o-hydroxybenzoic acid ethyl ester Natural products CCOC(=O)C1=CC=CC=C1O GYCKQBWUSACYIF-UHFFFAOYSA-N 0.000 description 1
- 229950006584 obatoclax Drugs 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- CQYBNXGHMBNGCG-RNJXMRFFSA-N octahydroindole-2-carboxylic acid Chemical compound C1CCC[C@H]2N[C@H](C(=O)O)C[C@@H]21 CQYBNXGHMBNGCG-RNJXMRFFSA-N 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 229940126701 oral medication Drugs 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- DWAFYCQODLXJNR-BNTLRKBRSA-L oxaliplatin Chemical compound O1C(=O)C(=O)O[Pt]11N[C@@H]2CCCC[C@H]2N1 DWAFYCQODLXJNR-BNTLRKBRSA-L 0.000 description 1
- 229960001756 oxaliplatin Drugs 0.000 description 1
- JMJRYTGVHCAYCT-UHFFFAOYSA-N oxan-4-one Chemical compound O=C1CCOCC1 JMJRYTGVHCAYCT-UHFFFAOYSA-N 0.000 description 1
- OJEOJUQOECNDND-UHFFFAOYSA-N oxetan-3-amine Chemical compound NC1COC1 OJEOJUQOECNDND-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N p-hydroxybenzoic acid methyl ester Natural products COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 229960001972 panitumumab Drugs 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 208000030940 penile carcinoma Diseases 0.000 description 1
- 201000008174 penis carcinoma Diseases 0.000 description 1
- FPVKHBSQESCIEP-JQCXWYLXSA-N pentostatin Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(N=CNC[C@H]2O)=C2N=C1 FPVKHBSQESCIEP-JQCXWYLXSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 201000002628 peritoneum cancer Diseases 0.000 description 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- DCWXELXMIBXGTH-UHFFFAOYSA-N phosphotyrosine Chemical compound OC(=O)C(N)CC1=CC=C(OP(O)(O)=O)C=C1 DCWXELXMIBXGTH-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- LHNIIDJUOCFXAP-UHFFFAOYSA-N pictrelisib Chemical compound C1CN(S(=O)(=O)C)CCN1CC1=CC2=NC(C=3C=4C=NNC=4C=CC=3)=NC(N3CCOCC3)=C2S1 LHNIIDJUOCFXAP-UHFFFAOYSA-N 0.000 description 1
- 229950010456 pimonidazole Drugs 0.000 description 1
- 229930006728 pinane Natural products 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 125000006684 polyhaloalkyl group Polymers 0.000 description 1
- 229920002338 polyhydroxyethylmethacrylate Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000002600 positron emission tomography Methods 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
- 229960004618 prednisone Drugs 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- CPTBDICYNRMXFX-UHFFFAOYSA-N procarbazine Chemical compound CNNCC1=CC=C(C(=O)NC(C)C)C=C1 CPTBDICYNRMXFX-UHFFFAOYSA-N 0.000 description 1
- 229960000624 procarbazine Drugs 0.000 description 1
- 229940095055 progestogen systemic hormonal contraceptives Drugs 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- IHPPCOHQZPLMBW-KRWDZBQOSA-N propan-2-yl 2-[4-(ethylcarbamoylamino)phenyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)OC(C)C)C2 IHPPCOHQZPLMBW-KRWDZBQOSA-N 0.000 description 1
- OKDLGTQFAGHPCY-KRWDZBQOSA-N propan-2-yl 2-[4-(ethylcarbamoylamino)phenyl]-4-[(3s)-3-methylmorpholin-4-yl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidine-6-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CN(C(=O)OC(C)C)CC2 OKDLGTQFAGHPCY-KRWDZBQOSA-N 0.000 description 1
- UIRUEPAOXJBSAX-UHFFFAOYSA-N propan-2-yl 2-[4-(ethylcarbamoylamino)phenyl]-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)OC(C)C)C2 UIRUEPAOXJBSAX-UHFFFAOYSA-N 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 239000003207 proteasome inhibitor Substances 0.000 description 1
- 239000003528 protein farnesyltransferase inhibitor Substances 0.000 description 1
- 229940121649 protein inhibitor Drugs 0.000 description 1
- 239000012268 protein inhibitor Substances 0.000 description 1
- 108060006633 protein kinase Proteins 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-YZRHJBSPSA-N pyrrolidin-2-one Chemical group O=C1CC[14CH2]N1 HNJBEVLQSNELDL-YZRHJBSPSA-N 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 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 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002534 radiation-sensitizing agent Substances 0.000 description 1
- GZUITABIAKMVPG-UHFFFAOYSA-N raloxifene Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 GZUITABIAKMVPG-UHFFFAOYSA-N 0.000 description 1
- 229960004622 raloxifene Drugs 0.000 description 1
- 229960004432 raltitrexed Drugs 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 210000003705 ribosome Anatomy 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 201000003804 salivary gland carcinoma Diseases 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229950009919 saracatinib Drugs 0.000 description 1
- 229940043230 sarcosine Drugs 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical class O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- 229960003440 semustine Drugs 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 208000000587 small cell lung carcinoma Diseases 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229910001467 sodium calcium phosphate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- IVDHYUQIDRJSTI-UHFFFAOYSA-N sorafenib tosylate Chemical compound [H+].CC1=CC=C(S([O-])(=O)=O)C=C1.C1=NC(C(=O)NC)=CC(OC=2C=CC(NC(=O)NC=3C=C(C(Cl)=CC=3)C(F)(F)F)=CC=2)=C1 IVDHYUQIDRJSTI-UHFFFAOYSA-N 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229940071182 stannate Drugs 0.000 description 1
- 125000005402 stannate group Chemical group 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- SFVFIFLLYFPGHH-UHFFFAOYSA-M stearalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SFVFIFLLYFPGHH-UHFFFAOYSA-M 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000011146 sterile filtration Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940120982 tarceva Drugs 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960004964 temozolomide Drugs 0.000 description 1
- 229960000235 temsirolimus Drugs 0.000 description 1
- SMPCLQCICDGOCB-WMZHIEFXSA-N tert-butyl (8r)-2-[4-(ethylcarbamoylamino)phenyl]-4-[(3s)-3-methylmorpholin-4-yl]-8-prop-2-enyl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)OC(C)(C)C)[C@@H]2CC=C SMPCLQCICDGOCB-WMZHIEFXSA-N 0.000 description 1
- RRKRYAGIWXSHBP-OAQYLSRUSA-N tert-butyl (8r)-2-[4-(ethylcarbamoylamino)phenyl]-8-(2-hydroxyethyl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)OC(C)(C)C)[C@@H]2CCO RRKRYAGIWXSHBP-OAQYLSRUSA-N 0.000 description 1
- FAAKQKSBGJQYFL-ZWKOTPCHSA-N tert-butyl (8r)-2-[4-(ethylcarbamoylamino)phenyl]-8-methyl-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)OC(C)(C)C)[C@@H]2C FAAKQKSBGJQYFL-ZWKOTPCHSA-N 0.000 description 1
- VVLSVTFDBACLMT-OAQYLSRUSA-N tert-butyl (8r)-8-(cyanomethyl)-2-[4-(ethylcarbamoylamino)phenyl]-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)OC(C)(C)C)[C@@H]2CC#N VVLSVTFDBACLMT-OAQYLSRUSA-N 0.000 description 1
- NOCAKDWPNQYSSR-PVOYRIJTSA-N tert-butyl (8r)-8-[(e)-4-ethoxy-4-oxobut-2-enyl]-2-[4-(ethylcarbamoylamino)phenyl]-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)OC(C)(C)C)[C@@H]2C\C=C\C(=O)OCC NOCAKDWPNQYSSR-PVOYRIJTSA-N 0.000 description 1
- AOSASMVTSWYSAW-OAQYLSRUSA-N tert-butyl (8r)-8-ethyl-2-[4-(ethylcarbamoylamino)phenyl]-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)OC(C)(C)C)[C@@H]2CC AOSASMVTSWYSAW-OAQYLSRUSA-N 0.000 description 1
- FAAKQKSBGJQYFL-ROUUACIJSA-N tert-butyl (8s)-2-[4-(ethylcarbamoylamino)phenyl]-8-methyl-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)OC(C)(C)C)[C@H]2C FAAKQKSBGJQYFL-ROUUACIJSA-N 0.000 description 1
- BJLBKGUJKOOVQC-AVRDEDQJSA-N tert-butyl (8s)-8-(cyanomethyl)-2-[4-(ethylcarbamoylamino)phenyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)OC(C)(C)C)[C@H]2CC#N BJLBKGUJKOOVQC-AVRDEDQJSA-N 0.000 description 1
- VVLSVTFDBACLMT-NRFANRHFSA-N tert-butyl (8s)-8-(cyanomethyl)-2-[4-(ethylcarbamoylamino)phenyl]-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)OC(C)(C)C)[C@H]2CC#N VVLSVTFDBACLMT-NRFANRHFSA-N 0.000 description 1
- NOCAKDWPNQYSSR-DRBUTMMVSA-N tert-butyl (8s)-8-[(e)-4-ethoxy-4-oxobut-2-enyl]-2-[4-(ethylcarbamoylamino)phenyl]-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)OC(C)(C)C)[C@H]2C\C=C\C(=O)OCC NOCAKDWPNQYSSR-DRBUTMMVSA-N 0.000 description 1
- AOSASMVTSWYSAW-NRFANRHFSA-N tert-butyl (8s)-8-ethyl-2-[4-(ethylcarbamoylamino)phenyl]-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)OC(C)(C)C)[C@H]2CC AOSASMVTSWYSAW-NRFANRHFSA-N 0.000 description 1
- YPTQBCCFRRAECZ-UHFFFAOYSA-N tert-butyl 2,4-dichloro-7,8-dihydro-5h-pyrido[4,3-d]pyrimidine-6-carboxylate Chemical compound ClC1=NC(Cl)=C2CN(C(=O)OC(C)(C)C)CCC2=N1 YPTQBCCFRRAECZ-UHFFFAOYSA-N 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- RINYDBZXKNWTFJ-INIZCTEOSA-N tert-butyl 2-(1h-indol-5-yl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C[C@H]1COCCN1C1=NC(C=2C=C3C=CNC3=CC=2)=NC2=C1CCN(C(=O)OC(C)(C)C)C2 RINYDBZXKNWTFJ-INIZCTEOSA-N 0.000 description 1
- APUDFYFECGKPIM-UHFFFAOYSA-N tert-butyl 2-(2-aminopyrimidin-5-yl)-4-(3,4-dihydro-2h-pyran-4-yl)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylate Chemical compound C=12CN(C(=O)OC(C)(C)C)CC2=NC(C=2C=NC(N)=NC=2)=NC=1C1CCOC=C1 APUDFYFECGKPIM-UHFFFAOYSA-N 0.000 description 1
- ZEAUGUMFPRQPIQ-UHFFFAOYSA-N tert-butyl 2-(2-aminopyrimidin-5-yl)-4-(oxan-4-yl)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylate Chemical compound C=12CN(C(=O)OC(C)(C)C)CC2=NC(C=2C=NC(N)=NC=2)=NC=1C1CCOCC1 ZEAUGUMFPRQPIQ-UHFFFAOYSA-N 0.000 description 1
- QFOFFCNUACPNKZ-ZDUSSCGKSA-N tert-butyl 2-(2-aminopyrimidin-5-yl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C[C@H]1COCCN1C1=NC(C=2C=NC(N)=NC=2)=NC2=C1CCN(C(=O)OC(C)(C)C)C2 QFOFFCNUACPNKZ-ZDUSSCGKSA-N 0.000 description 1
- FUNKWXUNRDQHAN-UHFFFAOYSA-N tert-butyl 2-(2-aminopyrimidin-5-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC2=C1N=C(C=1C=NC(N)=NC=1)N=C2N1CCOCC1 FUNKWXUNRDQHAN-UHFFFAOYSA-N 0.000 description 1
- MEWOFQDXWOUWEX-INIZCTEOSA-N tert-butyl 2-[3-(hydroxymethyl)-4-methoxyphenyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1=C(CO)C(OC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)OC(C)(C)C)C2 MEWOFQDXWOUWEX-INIZCTEOSA-N 0.000 description 1
- MUJGWSSYKVMFNR-KRWDZBQOSA-N tert-butyl 2-[4-(1h-imidazol-2-ylamino)phenyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC=3NC=CN=3)=CC=2)=NC2=C1CCN(C(=O)OC(C)(C)C)C2 MUJGWSSYKVMFNR-KRWDZBQOSA-N 0.000 description 1
- XEICHIHMRNRHCS-SFHVURJKSA-N tert-butyl 2-[4-(2-amino-5-methylimidazol-1-yl)phenyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(=CC=2)N2C(=NC=C2C)N)=NC2=C1CCN(C(=O)OC(C)(C)C)C2 XEICHIHMRNRHCS-SFHVURJKSA-N 0.000 description 1
- NCFNDCSMEDPVJY-KRWDZBQOSA-N tert-butyl 2-[4-(2-hydroxyethylcarbamoylamino)phenyl]-4-[(3s)-3-methylmorpholin-4-yl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidine-6-carboxylate Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCCO)=CC=2)=NC2=C1CN(C(=O)OC(C)(C)C)CC2 NCFNDCSMEDPVJY-KRWDZBQOSA-N 0.000 description 1
- GIJCGIFOWFKTPE-UHFFFAOYSA-N tert-butyl 2-[4-(ethylcarbamoylamino)phenyl]-4-(3-oxopiperazin-1-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CC(=O)NCC2)=NC2=C1CCN(C(=O)OC(C)(C)C)C2 GIJCGIFOWFKTPE-UHFFFAOYSA-N 0.000 description 1
- AYSSWCQKUIYQAL-BGYRXZFFSA-N tert-butyl 2-[4-(ethylcarbamoylamino)phenyl]-4-[(1s,5r)-8-oxa-3-azabicyclo[3.2.1]octan-3-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C([C@]1(CC[C@@](C2)(O1)[H])[H])N2C(C=1CCN(CC=1N=1)C(=O)OC(C)(C)C)=NC=1C1=CC=C(NC(=O)NCC)C=C1 AYSSWCQKUIYQAL-BGYRXZFFSA-N 0.000 description 1
- OIBGRGIJFNDIHS-IBGZPJMESA-N tert-butyl 2-[4-(ethylcarbamoylamino)phenyl]-4-[(3s)-3-(hydroxymethyl)morpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)CO)=NC2=C1CCN(C(=O)OC(C)(C)C)C2 OIBGRGIJFNDIHS-IBGZPJMESA-N 0.000 description 1
- NLPOHPJVDDEGHU-KRWDZBQOSA-N tert-butyl 2-[4-(ethylcarbamoylamino)phenyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)OC(C)(C)C)C2 NLPOHPJVDDEGHU-KRWDZBQOSA-N 0.000 description 1
- XBFSEWUFJMORKE-HSZRJFAPSA-N tert-butyl 2-[4-(ethylcarbamoylamino)phenyl]-4-[(3s)-3-propan-2-ylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C(C)C)=NC2=C1CCN(C(=O)OC(C)(C)C)C2 XBFSEWUFJMORKE-HSZRJFAPSA-N 0.000 description 1
- MXMYYCUMYNWNBL-UHFFFAOYSA-N tert-butyl 2-[4-(ethylcarbamoylamino)phenyl]-4-pyridin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1C=2C=CN=CC=2)=NC2=C1CCN(C(=O)OC(C)(C)C)C2 MXMYYCUMYNWNBL-UHFFFAOYSA-N 0.000 description 1
- QZPHUXZVUSPAOM-SFHVURJKSA-N tert-butyl 2-[4-(ethylcarbamoylamino)phenyl]-8,8-dimethyl-4-[(3s)-3-methylmorpholin-4-yl]-5,6-dihydropyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2[C@H](COCC2)C)=C(CCN(C(=O)OC(C)(C)C)C2(C)C)C2=N1 QZPHUXZVUSPAOM-SFHVURJKSA-N 0.000 description 1
- CVATYMBTGFIUPM-UHFFFAOYSA-N tert-butyl 2-[4-(ethylcarbamoylamino)phenyl]-8,8-dimethyl-4-morpholin-4-yl-5,6-dihydropyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2CCOCC2)=C(CCN(C(=O)OC(C)(C)C)C2(C)C)C2=N1 CVATYMBTGFIUPM-UHFFFAOYSA-N 0.000 description 1
- FAAKQKSBGJQYFL-ZENAZSQFSA-N tert-butyl 2-[4-(ethylcarbamoylamino)phenyl]-8-methyl-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)OC(C)(C)C)C2C FAAKQKSBGJQYFL-ZENAZSQFSA-N 0.000 description 1
- AOZQFLCLKSXYRA-UHFFFAOYSA-N tert-butyl 2-[4-(ethylcarbamoylamino)phenyl]-8-methyl-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)OC(C)(C)C)C2C AOZQFLCLKSXYRA-UHFFFAOYSA-N 0.000 description 1
- ZSCFCMGJXSFYGP-HNNXBMFYSA-N tert-butyl 2-[4-(ethylcarbamoylamino)pyrazol-1-yl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1=C(NC(=O)NCC)C=NN1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)OC(C)(C)C)C2 ZSCFCMGJXSFYGP-HNNXBMFYSA-N 0.000 description 1
- BNWUAPFLCOIYOA-UHFFFAOYSA-N tert-butyl 2-[4-(methylamino)phenyl]-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1=CC(NC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)OC(C)(C)C)C2 BNWUAPFLCOIYOA-UHFFFAOYSA-N 0.000 description 1
- MBLOQLGLZGMCSB-KRWDZBQOSA-N tert-butyl 2-[4-[(3-methyl-2,4-dioxo-1h-pyrimidin-6-yl)amino]phenyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC=3NC(=O)N(C)C(=O)C=3)=CC=2)=NC2=C1CCN(C(=O)OC(C)(C)C)C2 MBLOQLGLZGMCSB-KRWDZBQOSA-N 0.000 description 1
- WWTPIETUZPYYHT-UHFFFAOYSA-N tert-butyl 2-[4-[ethylcarbamoyl(methyl)amino]phenyl]-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C1=CC(N(C)C(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)OC(C)(C)C)C2 WWTPIETUZPYYHT-UHFFFAOYSA-N 0.000 description 1
- NTWRPUATNTZHMJ-UHFFFAOYSA-N tert-butyl 2-chloro-4-morpholin-4-yl-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylate Chemical compound C=12CN(C(=O)OC(C)(C)C)CC2=NC(Cl)=NC=1N1CCOCC1 NTWRPUATNTZHMJ-UHFFFAOYSA-N 0.000 description 1
- SYAPTYDHMNADTA-FQEVSTJZSA-N tert-butyl 4-[(3s)-3-ethylmorpholin-4-yl]-2-[4-(2-hydroxyethylcarbamoylamino)phenyl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound CC[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCCO)=CC=2)=NC2=C1CCN(C(=O)OC(C)(C)C)C2 SYAPTYDHMNADTA-FQEVSTJZSA-N 0.000 description 1
- MGJFICMMVOCTGU-INIZCTEOSA-N tert-butyl 4-[(3s)-3-methylmorpholin-4-yl]-2-(2-oxo-1h-quinolin-6-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C[C@H]1COCCN1C1=NC(C=2C=C3C=CC(=O)NC3=CC=2)=NC2=C1CCN(C(=O)OC(C)(C)C)C2 MGJFICMMVOCTGU-INIZCTEOSA-N 0.000 description 1
- HIGKEUWRKRPDQA-KRWDZBQOSA-N tert-butyl 4-[(3s)-3-methylmorpholin-4-yl]-2-[4-(oxetan-3-ylcarbamoylamino)phenyl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NC3COC3)=CC=2)=NC2=C1CCN(C(=O)OC(C)(C)C)C2 HIGKEUWRKRPDQA-KRWDZBQOSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229960001712 testosterone propionate Drugs 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- YJBKVPRVZAQTPY-UHFFFAOYSA-J tetrachlorostannane;dihydrate Chemical compound O.O.Cl[Sn](Cl)(Cl)Cl YJBKVPRVZAQTPY-UHFFFAOYSA-J 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229960004559 theobromine Drugs 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229960001196 thiotepa Drugs 0.000 description 1
- 229960004072 thrombin Drugs 0.000 description 1
- 229960003087 tioguanine Drugs 0.000 description 1
- 229950002376 tirapazamine Drugs 0.000 description 1
- QVMPZNRFXAKISM-UHFFFAOYSA-N tirapazamine Chemical compound C1=CC=C2[N+]([O-])=NC(=N)N(O)C2=C1 QVMPZNRFXAKISM-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000003354 tissue distribution assay Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229940100611 topical cream Drugs 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 229940100615 topical ointment Drugs 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 229940044693 topoisomerase inhibitor Drugs 0.000 description 1
- XFCLJVABOIYOMF-QPLCGJKRSA-N toremifene Chemical compound C1=CC(OCCN(C)C)=CC=C1C(\C=1C=CC=CC=1)=C(\CCCl)C1=CC=CC=C1 XFCLJVABOIYOMF-QPLCGJKRSA-N 0.000 description 1
- 229960005026 toremifene Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 238000001890 transfection Methods 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 229960000575 trastuzumab Drugs 0.000 description 1
- 230000008736 traumatic injury Effects 0.000 description 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229960001099 trimetrexate Drugs 0.000 description 1
- NOYPYLRCIDNJJB-UHFFFAOYSA-N trimetrexate Chemical compound COC1=C(OC)C(OC)=CC(NCC=2C(=C3C(N)=NC(N)=NC3=CC=2)C)=C1 NOYPYLRCIDNJJB-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- XLRPYZSEQKXZAA-OCAPTIKFSA-N tropane Chemical compound C1CC[C@H]2CC[C@@H]1N2C XLRPYZSEQKXZAA-OCAPTIKFSA-N 0.000 description 1
- 229930004006 tropane Natural products 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 230000005951 type IV hypersensitivity Effects 0.000 description 1
- 208000027930 type IV hypersensitivity disease Diseases 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- VBEQCZHXXJYVRD-GACYYNSASA-N uroanthelone Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CS)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(C)C)[C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C1=CC=C(O)C=C1 VBEQCZHXXJYVRD-GACYYNSASA-N 0.000 description 1
- 208000037964 urogenital cancer Diseases 0.000 description 1
- 206010046766 uterine cancer Diseases 0.000 description 1
- 208000012991 uterine carcinoma Diseases 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 229940099039 velcade Drugs 0.000 description 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
- UGGWPQSBPIFKDZ-KOTLKJBCSA-N vindesine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(N)=O)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1N=C1[C]2C=CC=C1 UGGWPQSBPIFKDZ-KOTLKJBCSA-N 0.000 description 1
- 229960004355 vindesine Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000000304 virulence factor Substances 0.000 description 1
- 230000007923 virulence factor Effects 0.000 description 1
- 201000005102 vulva cancer Diseases 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/18—Bridged systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- 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
- A61K31/495—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8530908P | 2008-07-31 | 2008-07-31 | |
| US61/085,309 | 2008-07-31 | ||
| PCT/US2009/052469 WO2010014939A1 (en) | 2008-07-31 | 2009-07-31 | Pyrimidine compounds, compositions and methods of use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20110046514A true KR20110046514A (ko) | 2011-05-04 |
Family
ID=41610758
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020117004629A Ceased KR20110046514A (ko) | 2008-07-31 | 2009-07-31 | 피리미딘 화합물, 조성물 및 사용 방법 |
Country Status (23)
| Country | Link |
|---|---|
| US (2) | US8163763B2 (enExample) |
| EP (1) | EP2318377B1 (enExample) |
| JP (1) | JP2011529920A (enExample) |
| KR (1) | KR20110046514A (enExample) |
| CN (1) | CN102171194A (enExample) |
| AR (1) | AR073354A1 (enExample) |
| AU (1) | AU2009276339B2 (enExample) |
| BR (1) | BRPI0911688A2 (enExample) |
| CA (1) | CA2729045A1 (enExample) |
| CL (1) | CL2011000191A1 (enExample) |
| CO (1) | CO6311051A2 (enExample) |
| EC (1) | ECSP11010796A (enExample) |
| ES (1) | ES2432821T3 (enExample) |
| IL (1) | IL210462A0 (enExample) |
| MA (1) | MA32580B1 (enExample) |
| MX (1) | MX2011001196A (enExample) |
| NZ (1) | NZ590777A (enExample) |
| PE (1) | PE20110403A1 (enExample) |
| RU (1) | RU2473549C2 (enExample) |
| TW (1) | TW201018681A (enExample) |
| UA (1) | UA101676C2 (enExample) |
| WO (1) | WO2010014939A1 (enExample) |
| ZA (1) | ZA201100110B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017164705A1 (ko) * | 2016-03-24 | 2017-09-28 | 재단법인 대구경북첨단의료산업진흥재단 | 신규한 피리딘 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 fgfr 관련 질환의 예방 또는 치료용 약학적 조성물 |
Families Citing this family (56)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998010381A1 (en) * | 1996-09-04 | 1998-03-12 | Intertrust Technologies Corp. | Trusted infrastructure support systems, methods and techniques for secure electronic commerce, electronic transactions, commerce process control and automation, distributed computing, and rights management |
| AU2009260447B2 (en) | 2008-05-30 | 2012-03-29 | Amgen Inc. | Inhibitors of PI3 kinase |
| KR20110046514A (ko) | 2008-07-31 | 2011-05-04 | 제넨테크, 인크. | 피리미딘 화합물, 조성물 및 사용 방법 |
| WO2010043676A1 (en) * | 2008-10-17 | 2010-04-22 | Boehringer Ingelheim International Gmbh | Tetra-aza-heterocycles as phosphatidylinositol-3-kinases (pi3-kinases) inhibitor |
| CA2755061A1 (en) * | 2009-03-13 | 2010-09-16 | Cellzome Limited | Pyrimidine derivatives as mtor inhibitors |
| WO2010120991A1 (en) * | 2009-04-17 | 2010-10-21 | Wyeth Llc | 5, 6, 7, 8-tetrahydropyrido[4,3-d]pyrimidine compounds, their use as mtor, pi3, and hsmg-1 kinase inhibitors, and their syntheses |
| WO2010120996A1 (en) * | 2009-04-17 | 2010-10-21 | Wyeth Llc | 5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine compounds, their use as mtor kinase and pi3 kinase inhibitors, and their syntheses |
| UY32582A (es) | 2009-04-28 | 2010-11-30 | Amgen Inc | Inhibidores de fosfoinositida 3 cinasa y/u objetivo mamífero |
| SG176959A1 (en) * | 2009-06-24 | 2012-01-30 | Genentech Inc | Oxo-heterocycle fused pyrimidine compounds, compositions and methods of use |
| ES2567168T3 (es) * | 2009-11-12 | 2016-04-20 | F. Hoffmann-La Roche Ag | Compuestos purina y pirazolopirimidina N7-sustituidos, composiciones y métodos de utilización |
| US8288381B2 (en) * | 2009-11-12 | 2012-10-16 | Genentech, Inc. | N-9 substituted purine compounds, compositions and methods of use |
| US9249129B2 (en) | 2010-03-04 | 2016-02-02 | Cellzome Limited | Morpholino substituted urea derivatives as mTOR inhibitors |
| CN102803227B (zh) | 2010-03-16 | 2016-01-20 | 默克专利有限公司 | 吗啉基喹唑啉 |
| EP3075730B1 (en) | 2010-06-04 | 2018-10-24 | Genentech, Inc. | Aminopyrimidine derivatives as lrrk2 modulators |
| WO2012027234A1 (en) * | 2010-08-23 | 2012-03-01 | Schering Corporation | Fused tricyclic inhibitors of mammalian target of rapamycin |
| ES2746134T3 (es) | 2010-11-10 | 2020-03-04 | Genentech Inc | Derivados de pirazol aminopirimidina como moduladores de LRRK2 |
| KR20140099556A (ko) | 2010-12-16 | 2014-08-12 | 에프. 호프만-라 로슈 아게 | 트라이사이클릭 pi3k 억제제 화합물 및 이의 사용 방법 |
| ES2620644T3 (es) * | 2011-04-01 | 2017-06-29 | Genentech, Inc. | Combinaciones de compuestos inhibidores de AKT y agentes quimioterapéuticos, y métodos de uso |
| RU2013148817A (ru) * | 2011-04-01 | 2015-05-10 | Дженентек, Инк. | Комбинации соединений-ингибиторов акт и мек и способы их применения |
| JP2014510122A (ja) * | 2011-04-04 | 2014-04-24 | セルゾーム リミテッド | ｍＴＯＲ阻害剤としてのジヒドロピロロピリミジン誘導体 |
| US8846656B2 (en) | 2011-07-22 | 2014-09-30 | Novartis Ag | Tetrahydropyrido-pyridine and tetrahydropyrido-pyrimidine compounds and use thereof as C5a receptor modulators |
| US9101900B2 (en) | 2011-07-27 | 2015-08-11 | Res Usa, Llc | Gasification system and method |
| CN103917530B (zh) | 2011-09-21 | 2016-08-24 | 塞尔佐姆有限公司 | 作为mtor抑制剂的吗啉代取代的脲或氨基甲酸衍生物 |
| AU2012320465B2 (en) | 2011-10-07 | 2016-03-03 | Cellzome Limited | Morpholino substituted bicyclic pyrimidine urea or carbamate derivatives as mTOR inhibitors |
| AR089284A1 (es) | 2011-12-22 | 2014-08-13 | Galapagos Nv | Dihidropirimidinoisoquinolinonas y composiciones farmaceuticas de las mismas para el tratamiento de trastornos inflamatorios |
| WO2013134518A1 (en) | 2012-03-09 | 2013-09-12 | Amgen Inc. | Sulfamide sodium channel inhibitors |
| BR112014028881A2 (pt) | 2012-05-23 | 2017-06-27 | Hoffmann La Roche | populações de células, banco de células, métodos de obtenção de uma população de células, métodos de identificação de um fator, métodos de seleção, métodos de fornecimento de terapia, populações de hepatócitos e método de obtenção de células |
| AU2013380573B2 (en) * | 2013-03-08 | 2016-07-07 | Wockhardt Limited | A process for sodium salt of (2S, 5R)-2-carboxamido-7-oxo-6-sulfooxy -1,6-diaza-bicyclo[3.2.1]octane |
| RU2649141C2 (ru) * | 2015-04-20 | 2018-03-30 | государственное бюджетное образовательное учреждение высшего профессионального образования "Пермская государственная фармацевтическая академия" Министерства здравоохранения Российской Федерации (ГБОУ ВПО ПГФА Минздрава России) | 3,4-диметил-6-(3-пиридил)-N-фенил-2-оксо-1,2,3,6-тетрагидропиримидин-5-карбоксамид, проявляющий противогрибковое действие в отношении штамма Candida albicans |
| CN106467538B (zh) * | 2015-08-14 | 2019-03-05 | 沈阳中化农药化工研发有限公司 | 一种取代的四氢异喹啉化合物与用途 |
| MX382339B (es) | 2016-05-18 | 2025-03-13 | Mirati Therapeutics Inc | Inhibidores g12c de kras. |
| JOP20190257A1 (ar) | 2017-04-28 | 2019-10-28 | Novartis Ag | مركبات أريل غير متجانسة ثنائية الحلقة مندمجة 6-6 واستخدامها كمثبطات lats |
| JP7340519B2 (ja) * | 2017-11-06 | 2023-09-07 | メッドシャイン ディスカバリー インコーポレイテッド | ｍＴＯＲＣ１／２二重阻害剤としてのピリドピリミジン系化合物 |
| US10647715B2 (en) | 2017-11-15 | 2020-05-12 | Mirati Therapeutics, Inc. | KRas G12C inhibitors |
| EP3710439B1 (en) | 2017-11-15 | 2023-02-15 | Mirati Therapeutics, Inc. | Kras g12c inhibitors |
| JP7569688B2 (ja) | 2017-12-22 | 2024-10-18 | ハイバーセル，インコーポレイテッド | ホスファチジルイノシトールリン酸キナーゼ阻害剤としてのアミノピリジン誘導体 |
| HRP20220710T1 (hr) | 2018-04-24 | 2022-07-22 | Merck Patent Gmbh | Antiproliferacijski spojevi i njihova uporaba |
| US11932633B2 (en) | 2018-05-07 | 2024-03-19 | Mirati Therapeutics, Inc. | KRas G12C inhibitors |
| CN112955137B (zh) | 2018-09-10 | 2025-05-13 | 米拉蒂治疗股份有限公司 | 组合疗法 |
| WO2020055760A1 (en) | 2018-09-10 | 2020-03-19 | Mirati Therapeutics, Inc. | Combination therapies |
| LT3849537T (lt) | 2018-09-10 | 2025-02-10 | Mirati Therapeutics, Inc. | Kompleksinės terapijos |
| SG11202102357RA (en) | 2018-12-05 | 2021-04-29 | Mirati Therapeutics Inc | Combination therapies |
| JP7592601B2 (ja) | 2019-01-10 | 2024-12-02 | ミラティ セラピューティクス， インコーポレイテッド | Ｋｒａｓ ｇ１２ｃ阻害剤 |
| GB201905222D0 (en) * | 2019-04-12 | 2019-05-29 | Airspan Networks Inc | Air-to-ground (ATG) communication technologies |
| TW202112767A (zh) | 2019-06-17 | 2021-04-01 | 美商佩特拉製藥公司 | 作為磷脂酸肌醇磷酸激酶抑制劑之胺基吡啶衍生物 |
| WO2021041671A1 (en) | 2019-08-29 | 2021-03-04 | Mirati Therapeutics, Inc. | Kras g12d inhibitors |
| CA3152025A1 (en) | 2019-09-24 | 2021-04-01 | David BRIERE | Combination therapies |
| CN115135315B (zh) | 2019-12-20 | 2024-11-26 | 米拉蒂治疗股份有限公司 | Sos1抑制剂 |
| CA3190944A1 (en) | 2020-09-11 | 2022-03-17 | Mirati Therapeutics, Inc. | Crystalline forms of a kras g12c inhibitor |
| EP4214204A1 (en) | 2020-09-18 | 2023-07-26 | Bayer Aktiengesellschaft | Pyrido[2,3-d]pyrimidin-4-amines as sos1 inhibitors |
| EP4262807A4 (en) | 2020-12-15 | 2025-04-23 | Mirati Therapeutics, Inc. | Azachinazoline pan-KRAS inhibitors |
| US11999753B2 (en) | 2020-12-16 | 2024-06-04 | Mirati Therapeutics, Inc. | Tetrahydropyridopyrimidine pan-KRas inhibitors |
| EP4074317A1 (en) | 2021-04-14 | 2022-10-19 | Bayer AG | Phosphorus derivatives as novel sos1 inhibitors |
| CN115466258A (zh) * | 2021-06-11 | 2022-12-13 | 成都苑东生物制药股份有限公司 | Atr抑制剂及其用途 |
| CN117164590A (zh) * | 2022-05-25 | 2023-12-05 | 沈阳药科大学 | 稠合嘧啶类衍生物及其应用 |
| CN118538308B (zh) * | 2024-07-12 | 2024-11-22 | 碳氢数科(成都)信息技术有限公司 | 化学反应数据挖掘方法、系统、存储介质及终端 |
Family Cites Families (72)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1197466B (de) * | 1962-03-22 | 1965-07-29 | Thomae Gmbh Dr K | Verfahren zur Herstellung von neuen 5, 6, 7, 8-Tetrahydropyrido-[4, 3-d]pyrimidinen |
| JPH04224580A (ja) | 1990-12-25 | 1992-08-13 | Nippon Soda Co Ltd | ピリミジン誘導体、その製造方法及び農園芸用殺菌剤 |
| US5338740A (en) * | 1993-07-13 | 1994-08-16 | Pfizer Inc. | Angiotensin II receptor antagonists |
| ATE247469T1 (de) * | 1995-06-07 | 2003-09-15 | Pfizer | Heterocyclische kondensierte pyrimidin-derivate |
| US5942508A (en) * | 1997-02-04 | 1999-08-24 | Senju Pharmaceutical Co., Ltd. | Method for solubilizing pyridonecarboxylic acid solubilizer thereof and aqueous solution containing solubilized pyridonecarboxylic acid |
| US6187777B1 (en) * | 1998-02-06 | 2001-02-13 | Amgen Inc. | Compounds and methods which modulate feeding behavior and related diseases |
| PL204628B1 (pl) * | 1998-06-02 | 2010-01-29 | Osi Pharmaceuticals | Pochodna pirolo[2,3d]pirymidyny, jej zastosowanie i sposoby wytwarzania tej pochodnej i preparaty farmaceutyczne |
| 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 |
| KR100774855B1 (ko) * | 2000-04-27 | 2007-11-08 | 아스텔라스세이야쿠 가부시키가이샤 | 축합 헤테로아릴 유도체 |
| US6608053B2 (en) * | 2000-04-27 | 2003-08-19 | Yamanouchi Pharmaceutical Co., Ltd. | Fused heteroaryl derivatives |
| WO2002022605A1 (en) | 2000-09-15 | 2002-03-21 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| AP2003002825A0 (en) * | 2000-12-21 | 2003-09-30 | Vertex Pharma | Pyrazole compounds useful as protein kinase inhibitors |
| US7105667B2 (en) * | 2001-05-01 | 2006-09-12 | Bristol-Myers Squibb Co. | Fused heterocyclic compounds and use thereof |
| WO2002088079A2 (en) | 2001-05-01 | 2002-11-07 | Bristol-Myers Squibb Company | Dual inhibitors of pde 7 and pde 4 |
| PE20030008A1 (es) * | 2001-06-19 | 2003-01-22 | Bristol Myers Squibb Co | Inhibidores duales de pde 7 y pde 4 |
| AU2002364536B2 (en) * | 2001-12-07 | 2008-10-23 | Vertex Pharmaceuticals, Inc. | Pyrimidine-based compounds useful as GSK-3 inhibitors |
| US7091343B2 (en) * | 2002-03-15 | 2006-08-15 | Vertex Pharmaceuticals Incorporated | Compositions useful as inhibitors of protein kinases |
| US7524852B2 (en) * | 2002-06-07 | 2009-04-28 | Kyowa Hakko Kogyo Co., Ltd. | Bicyclic pyrimidine derivatives |
| JP4530852B2 (ja) * | 2002-07-15 | 2010-08-25 | メルク・シャープ・エンド・ドーム・コーポレイション | 糖尿病治療のためのピペリジノピリミジンジペプチジルペプチダーゼ阻害剤 |
| AU2003250475A1 (en) * | 2002-08-13 | 2004-02-25 | Warner-Lambert Company Llc | 5,6-fused 3,4-dihydropyrimidine-2-one derivatives as matrix metalloproteinase inhibitors |
| US7112676B2 (en) * | 2002-11-04 | 2006-09-26 | Hoffmann-La Roche Inc. | Pyrimido compounds having antiproliferative activity |
| US7223766B2 (en) * | 2003-03-28 | 2007-05-29 | Scios, Inc. | Bi-cyclic pyrimidine inhibitors of TGFβ |
| EP1646615B1 (en) * | 2003-06-06 | 2009-08-26 | Vertex Pharmaceuticals Incorporated | Pyrimidine derivatives as modulators of atp-binding cassette transporters |
| EP1663994B1 (en) * | 2003-08-05 | 2012-03-07 | Vertex Pharmaceuticals Incorporated | Tetrahydroquinazoline compounds as inhibitors of voltage-gated ion channels |
| US7312330B2 (en) | 2003-12-24 | 2007-12-25 | Renovis, Inc. | Bicycloheteroarylamine compounds as ion channel ligands and uses thereof |
| TW200530235A (en) | 2003-12-24 | 2005-09-16 | Renovis Inc | Bicycloheteroarylamine compounds as ion channel ligands and uses thereof |
| WO2005067546A2 (en) * | 2004-01-13 | 2005-07-28 | Ambit Biosciences Corporation | Pyrrolopyrimidine derivatives and analogs and their use in the treatment and prevention of diseases |
| AP2007003923A0 (en) | 2004-09-30 | 2007-02-28 | Tibotec Pharm Ltd | Hcv inhibiting bi-cyclic pyrimidines |
| US7906528B2 (en) * | 2004-10-05 | 2011-03-15 | Novartis International Pharmaceutical Ltd. | Pyrrolo-pyridine, pyrrolo-pyrimidine and related heterocyclic compounds |
| JP4862654B2 (ja) * | 2004-10-08 | 2012-01-25 | アステラス製薬株式会社 | 芳香環縮合ピリミジン誘導体 |
| TW200621257A (en) * | 2004-10-20 | 2006-07-01 | Astellas Pharma Inc | Pyrimidine derivative fused with nonaromatic ring |
| GB0423653D0 (en) * | 2004-10-25 | 2004-11-24 | Piramed Ltd | Pharmaceutical compounds |
| US20060128710A1 (en) * | 2004-12-09 | 2006-06-15 | Chih-Hung Lee | Antagonists to the vanilloid receptor subtype 1 (VR1) and uses thereof |
| JP2008525422A (ja) | 2004-12-23 | 2008-07-17 | ファイザー・プロダクツ・インク | 抗癌剤として有用な複素芳香族誘導体 |
| JP2008531538A (ja) | 2005-02-25 | 2008-08-14 | クドス ファーマシューティカルズ リミテッド | ２，４−ジアミノ−ピリドピリミジン誘導体とｍＴＯＲ阻害剤としてのその使用 |
| GB2431156A (en) | 2005-10-11 | 2007-04-18 | Piramed Ltd | 1-cyclyl-3-substituted- -benzenes and -azines as inhibitors of phosphatidylinositol 3-kinase |
| GB0520657D0 (en) * | 2005-10-11 | 2005-11-16 | Ludwig Inst Cancer Res | Pharmaceutical compounds |
| EP1954699B1 (en) * | 2005-11-22 | 2012-09-19 | Kudos Pharmaceuticals Ltd | PYRIDO-, PYRAZO- AND PYRIMIDOPYRIMIDINE DERIVATIVES AS mTOR INHIBITORS |
| KR20080083188A (ko) | 2006-01-11 | 2008-09-16 | 아스트라제네카 아베 | 모르폴리노 피리미딘 유도체 및 요법에서의 그 유도체의용도 |
| US7651687B2 (en) | 2006-03-13 | 2010-01-26 | Osi Pharmaceuticals, Inc. | Combined treatment with an EGFR kinase inhibitor and an agent that sensitizes tumor cells to the effects of EGFR kinase inhibitors |
| PE20080145A1 (es) * | 2006-03-21 | 2008-02-11 | Janssen Pharmaceutica Nv | Tetrahidro-pirimidoazepinas como moduladores de trpv1 |
| BRPI0710866A2 (pt) | 2006-04-26 | 2012-08-14 | Hoffmann La Roche | compostos farmacÊuticos |
| KR101402474B1 (ko) * | 2006-04-26 | 2014-06-19 | 제넨테크, 인크. | 포스포이노시티드 3-키나제 억제제 화합물 및 이를 포함하는 약학적 조성물 |
| MX2008013584A (es) * | 2006-04-26 | 2009-03-23 | Genentech Inc | Compuestos farmaceuticos. |
| BRPI0710874A2 (pt) * | 2006-04-26 | 2012-02-14 | Hoffmann La Roche | compostos de tienopirimidina, processos de produção dos referidos compostos, composições farmacêuticas contendo os mesmos, kit, produto, e usos dos compostos |
| GB0608820D0 (en) | 2006-05-04 | 2006-06-14 | Piramed Ltd | Pharmaceutical compounds |
| CN101511842B (zh) | 2006-07-06 | 2012-10-31 | 阵列生物制药公司 | 作为akt蛋白激酶抑制剂的二氢呋喃并嘧啶 |
| WO2008021456A2 (en) * | 2006-08-16 | 2008-02-21 | Cytovia, Inc. | N-aryl-5,7-dihydrofuro[3,4-d]pyrimidin-4-amines and analogs as activators of caspases and inducers of apoptosis and the use thereof |
| LT2057156T (lt) * | 2006-08-23 | 2017-05-25 | Kudos Pharmaceuticals Limited | 2-metilmorfolino pirido-, pirazo- ir pirimidopirimidino dariniai kaip mtor slopikliai |
| MX2009002046A (es) | 2006-08-24 | 2009-03-06 | Astrazeneca Ab | Derivados de morfolino pirimidina utiles en el tratamiento de trastornos proliferativos. |
| WO2008032072A1 (en) | 2006-09-14 | 2008-03-20 | Astrazeneca Ab | 2-benzimidaz0lyl-6-m0rph0lin0-4-piperidin-4-ylpyrimidine derivatives as pi3k and mtor inhibitors for the treatment of proliferative disorders |
| WO2008032033A1 (en) | 2006-09-14 | 2008-03-20 | Astrazeneca Ab | 4-benzimidazolyl-2-morpholino-6-piperazinylpyrimidine derivatives as pi3k and mtor inhibitors for the treatment of proliferative disorders |
| WO2008032036A1 (en) | 2006-09-14 | 2008-03-20 | Astrazeneca Ab | 6-benzimidaz0lyl-2-m0rph0lin0-4- (azetidine, pyrrolidine, piperidine or azepine) pyrimidine derivatives as pi3k and mtor inhibitors for the treatment of proliferative disorders |
| WO2008032089A1 (en) | 2006-09-14 | 2008-03-20 | Astrazeneca Ab | 4-benzimidaz0lyl-2-m0rph0lin0-6-piperidin-4-ylpyrimidine derivatives as pi3k and mtor inhibitors for the treatment of proliferative disorders |
| US20100022534A1 (en) | 2006-09-14 | 2010-01-28 | Astrazeneca | 2-benzimidazolyl-6-morpholino-4- (azetidine, pyrrolidine, piperidine or azepine) pyrimidine derivatives as pi3k and mtor inhibitors for the treatment of proliferative disorders |
| JP2010503651A (ja) | 2006-09-14 | 2010-02-04 | アストラゼネカ アクチボラグ | 増殖性障害の治療用のＰＩ３Ｋ及びｍＴＯＲ阻害剤としての２−ベンゾイミダゾリル−６−モルホリノ−フェニルピリミジン誘導体 |
| WO2008032060A1 (en) | 2006-09-14 | 2008-03-20 | Astrazeneca Ab | 4-benzimidaz0lyl-6-m0rph0lin0-2-piperazinylpyrimidine derivatives as p13k and mtor inhibitors for the treatment of proliferative disorders |
| ES2571028T3 (es) * | 2006-12-07 | 2016-05-23 | Genentech Inc | Compuestos inhibidores de fosfoinositida 3-cinasa y métodos de uso |
| AR064155A1 (es) * | 2006-12-07 | 2009-03-18 | Piramed Ltd | Compuestos de inhibidores de fosfoinositido-3 quinasa y metodos de uso |
| US20100034786A1 (en) * | 2006-12-14 | 2010-02-11 | Medical Research Council | Use of PI3K M-TOR and Akt Inhibitors to Induce FOXP3 Expression and Generate Regulatory T Cells |
| US20080233127A1 (en) | 2007-03-21 | 2008-09-25 | Wyeth | Imidazolopyrimidine analogs and their use as pi3 kinase and mtor inhibitors |
| US20080234262A1 (en) * | 2007-03-21 | 2008-09-25 | Wyeth | Pyrazolopyrimidine analogs and their use as mtor kinase and pi3 kinase inhibitors |
| DE602008004650D1 (de) | 2007-04-12 | 2011-03-03 | Hoffmann La Roche | Pyrimidinderivate als inhibitoren von phosphatidylinositol-3-kinase |
| WO2008125833A1 (en) | 2007-04-12 | 2008-10-23 | Piramed Limited | Pharmaceutical compounds |
| GB0707087D0 (en) | 2007-04-12 | 2007-05-23 | Piramed Ltd | Pharmaceutical compounds |
| WO2008152387A1 (en) | 2007-06-12 | 2008-12-18 | F.Hoffmann-La Roche Ag | Quinazoline derivatives as pi3 kinase inhibitors |
| WO2008152394A1 (en) | 2007-06-12 | 2008-12-18 | F.Hoffmann-La Roche Ag | Pharmaceutical compounds |
| CN101679456B (zh) | 2007-06-12 | 2012-09-05 | 霍夫曼-拉罗奇有限公司 | 噻唑并嘧啶类和它们作为磷脂酰肌醇3-激酶的抑制剂的应用 |
| CA2704711C (en) * | 2007-09-24 | 2016-07-05 | Genentech, Inc. | Thiazolopyrimidine p13k inhibitor compounds and methods of use |
| MX2010004260A (es) * | 2007-10-16 | 2010-04-30 | Wyeth Llc | Compuestos de tienopirimidina y pirazolopirimidina y su uso como inhibidores de mtor cinasa y pi3 cinasa. |
| US20090149458A1 (en) * | 2007-11-27 | 2009-06-11 | Wyeth | PYRROLO[3,2-d]PYRIMIDINE COMPOUNDS AND THEIR USE AS PI3 KINASE AND mTOR KINASE INHIBITORS |
| KR20110046514A (ko) | 2008-07-31 | 2011-05-04 | 제넨테크, 인크. | 피리미딘 화합물, 조성물 및 사용 방법 |
-
2009
- 2009-07-31 KR KR1020117004629A patent/KR20110046514A/ko not_active Ceased
- 2009-07-31 US US12/533,935 patent/US8163763B2/en not_active Expired - Fee Related
- 2009-07-31 NZ NZ590777A patent/NZ590777A/xx not_active IP Right Cessation
- 2009-07-31 EP EP09803674.2A patent/EP2318377B1/en active Active
- 2009-07-31 BR BRPI0911688-5A patent/BRPI0911688A2/pt not_active IP Right Cessation
- 2009-07-31 MX MX2011001196A patent/MX2011001196A/es active IP Right Grant
- 2009-07-31 AR ARP090102947A patent/AR073354A1/es unknown
- 2009-07-31 TW TW098125944A patent/TW201018681A/zh unknown
- 2009-07-31 ES ES09803674T patent/ES2432821T3/es active Active
- 2009-07-31 WO PCT/US2009/052469 patent/WO2010014939A1/en not_active Ceased
- 2009-07-31 RU RU2011107278/04A patent/RU2473549C2/ru not_active IP Right Cessation
- 2009-07-31 PE PE2010001222A patent/PE20110403A1/es not_active Application Discontinuation
- 2009-07-31 JP JP2011521363A patent/JP2011529920A/ja active Pending
- 2009-07-31 CA CA2729045A patent/CA2729045A1/en not_active Abandoned
- 2009-07-31 CN CN200980139005XA patent/CN102171194A/zh active Pending
- 2009-07-31 UA UAA201102282A patent/UA101676C2/uk unknown
- 2009-07-31 AU AU2009276339A patent/AU2009276339B2/en not_active Ceased
-
2011
- 2011-01-04 ZA ZA2011/00110A patent/ZA201100110B/en unknown
- 2011-01-05 IL IL210462A patent/IL210462A0/en unknown
- 2011-01-28 CL CL2011000191A patent/CL2011000191A1/es unknown
- 2011-01-31 EC EC2011010796A patent/ECSP11010796A/es unknown
- 2011-02-22 MA MA33637A patent/MA32580B1/fr unknown
- 2011-02-24 CO CO11022828A patent/CO6311051A2/es not_active Application Discontinuation
-
2012
- 2012-03-01 US US13/410,246 patent/US20120165313A1/en not_active Abandoned
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017164705A1 (ko) * | 2016-03-24 | 2017-09-28 | 재단법인 대구경북첨단의료산업진흥재단 | 신규한 피리딘 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 fgfr 관련 질환의 예방 또는 치료용 약학적 조성물 |
Also Published As
| Publication number | Publication date |
|---|---|
| ECSP11010796A (es) | 2011-02-28 |
| ZA201100110B (en) | 2012-04-25 |
| WO2010014939A1 (en) | 2010-02-04 |
| ES2432821T3 (es) | 2013-12-05 |
| EP2318377A4 (en) | 2012-05-09 |
| AU2009276339A1 (en) | 2010-02-04 |
| IL210462A0 (en) | 2011-03-31 |
| EP2318377A1 (en) | 2011-05-11 |
| CO6311051A2 (es) | 2011-08-22 |
| US20100069357A1 (en) | 2010-03-18 |
| BRPI0911688A2 (pt) | 2015-07-28 |
| AU2009276339B2 (en) | 2012-06-07 |
| EP2318377B1 (en) | 2013-08-21 |
| NZ590777A (en) | 2012-11-30 |
| RU2473549C2 (ru) | 2013-01-27 |
| CA2729045A1 (en) | 2010-02-04 |
| AR073354A1 (es) | 2010-11-03 |
| AU2009276339A8 (en) | 2011-03-03 |
| RU2011107278A (ru) | 2012-09-10 |
| US8163763B2 (en) | 2012-04-24 |
| UA101676C2 (uk) | 2013-04-25 |
| PE20110403A1 (es) | 2011-07-04 |
| MX2011001196A (es) | 2011-05-30 |
| US20120165313A1 (en) | 2012-06-28 |
| MA32580B1 (fr) | 2011-08-01 |
| CL2011000191A1 (es) | 2011-05-20 |
| TW201018681A (en) | 2010-05-16 |
| CN102171194A (zh) | 2011-08-31 |
| JP2011529920A (ja) | 2011-12-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP2318377B1 (en) | Pyrimidine compounds, compositions and methods of use | |
| AU2021309876B2 (en) | Rock inhibitor, and preparation method therefor and use thereof | |
| KR101659193B1 (ko) | Btk 활성의 억제제로서의 헤테로아릴 피리돈 및 아자-피리돈 화합물 | |
| EP3524603B1 (en) | Fgfr4 inhibitor, preparation method therefor and pharmaceutical use thereof | |
| JP6496376B2 (ja) | 阻害剤化合物 | |
| AU2019253510B2 (en) | BCL6 inhibitors | |
| EP2558468B1 (en) | 5, 7-substituted-imidazo [1,2-c] pyrimidines as inhibitors of jak kinases | |
| AU2018388406B2 (en) | Aryl-bipyridine amine derivatives as phosphatidylinositol phosphate kinase inhibitors | |
| JP2018150358A (ja) | Ｔａｎｋ結合キナーゼインヒビター化合物 | |
| JP2012526836A (ja) | Ｐｉｋｋ阻害薬としてのヘテロアリール化合物 | |
| WO2018215798A1 (en) | 2-quinolone derived inhibitors of bcl6 | |
| AU2017332839B2 (en) | Preparation and uses of pyrimidinone derivatives | |
| HK1160466A (en) | Pyrimidine compounds, compositions and methods of use | |
| HK40095873A (en) | Bcl6 inhibitors | |
| HK40046058A (en) | Bcl6 inhibitors | |
| HK40046058B (en) | Bcl6 inhibitors | |
| EA050300B1 (ru) | Ингибиторы bcl6 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A201 | Request for examination | ||
| PA0105 | International application |
Patent event date: 20110225 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PA0201 | Request for examination | ||
| PG1501 | Laying open of application | ||
| PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 20130131 Patent event code: PE09021S01D |
|
| E601 | Decision to refuse application | ||
| PE0601 | Decision on rejection of patent |
Patent event date: 20130731 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 20130131 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |