CA2729045A1 - Pyrimidine compounds, compositions and methods of use - Google Patents
Pyrimidine compounds, compositions and methods of use Download PDFInfo
- Publication number
- CA2729045A1 CA2729045A1 CA2729045A CA2729045A CA2729045A1 CA 2729045 A1 CA2729045 A1 CA 2729045A1 CA 2729045 A CA2729045 A CA 2729045A CA 2729045 A CA2729045 A CA 2729045A CA 2729045 A1 CA2729045 A1 CA 2729045A1
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- pyrimidin
- tetrahydropyrido
- group
- compound
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims description 225
- 239000000203 mixture Substances 0.000 title description 107
- 150000003230 pyrimidines Chemical class 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 453
- 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
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 44
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 43
- 201000011510 cancer Diseases 0.000 claims abstract description 34
- 150000003839 salts Chemical class 0.000 claims abstract description 34
- 238000011282 treatment Methods 0.000 claims abstract description 25
- -1 3-methyl-morpholin-4-yl Chemical group 0.000 claims description 164
- 229910052740 iodine Inorganic materials 0.000 claims description 98
- 125000001424 substituent group Chemical group 0.000 claims description 81
- 229910052757 nitrogen Inorganic materials 0.000 claims description 72
- 229910052739 hydrogen Inorganic materials 0.000 claims description 66
- 239000001257 hydrogen Substances 0.000 claims description 65
- 125000000217 alkyl group Chemical group 0.000 claims description 64
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 64
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 43
- 150000002431 hydrogen Chemical class 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 40
- 125000005842 heteroatom Chemical group 0.000 claims description 39
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 39
- 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
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 33
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 32
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 31
- 125000004429 atom Chemical group 0.000 claims description 29
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 208000035475 disorder Diseases 0.000 claims description 23
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 23
- 125000000623 heterocyclic group Chemical group 0.000 claims description 22
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims description 20
- 241000124008 Mammalia Species 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 17
- 125000001188 haloalkyl group Chemical group 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 16
- 125000002947 alkylene group Chemical group 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 230000000694 effects Effects 0.000 claims description 13
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 12
- 239000003085 diluting agent Substances 0.000 claims description 11
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 10
- 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 10
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 241000282414 Homo sapiens Species 0.000 claims description 7
- 239000002246 antineoplastic agent Substances 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
- 206010039491 Sarcoma Diseases 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 208000032839 leukemia Diseases 0.000 claims description 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
- 210000000214 mouth Anatomy 0.000 claims description 6
- 210000003800 pharynx Anatomy 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
- 206010041823 squamous cell carcinoma Diseases 0.000 claims description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 5
- 201000009030 Carcinoma Diseases 0.000 claims description 5
- 208000010667 Carcinoma of liver and intrahepatic biliary tract Diseases 0.000 claims description 5
- 206010073069 Hepatic cancer Diseases 0.000 claims description 5
- 206010038389 Renal cancer Diseases 0.000 claims description 5
- 210000000481 breast Anatomy 0.000 claims description 5
- 208000005017 glioblastoma Diseases 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- 201000002250 liver carcinoma Diseases 0.000 claims description 5
- 125000002950 monocyclic group Chemical group 0.000 claims description 5
- 210000001672 ovary Anatomy 0.000 claims description 5
- 210000000664 rectum Anatomy 0.000 claims description 5
- 208000000649 small cell carcinoma Diseases 0.000 claims description 5
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 4
- 206010005003 Bladder cancer Diseases 0.000 claims description 4
- 125000004450 alkenylene group Chemical group 0.000 claims description 4
- 125000002837 carbocyclic group Chemical group 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 229940127089 cytotoxic agent Drugs 0.000 claims description 4
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 4
- 210000004072 lung Anatomy 0.000 claims description 4
- 201000005249 lung adenocarcinoma Diseases 0.000 claims description 4
- 201000001441 melanoma Diseases 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 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
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 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
- 208000003200 Adenoma Diseases 0.000 claims description 3
- 206010001233 Adenoma benign Diseases 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 208000017604 Hodgkin disease Diseases 0.000 claims description 3
- 206010023347 Keratoacanthoma Diseases 0.000 claims description 3
- 206010029260 Neuroblastoma Diseases 0.000 claims description 3
- 201000010208 Seminoma Diseases 0.000 claims description 3
- 208000009956 adenocarcinoma Diseases 0.000 claims description 3
- 201000001531 bladder carcinoma Diseases 0.000 claims description 3
- 210000000988 bone and bone Anatomy 0.000 claims description 3
- 210000000133 brain stem Anatomy 0.000 claims description 3
- 210000003169 central nervous system Anatomy 0.000 claims description 3
- 210000003679 cervix uteri Anatomy 0.000 claims description 3
- 210000001072 colon Anatomy 0.000 claims description 3
- 210000003238 esophagus Anatomy 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
- 210000003734 kidney Anatomy 0.000 claims description 3
- 208000003849 large cell carcinoma Diseases 0.000 claims description 3
- 210000002429 large intestine Anatomy 0.000 claims description 3
- 210000000867 larynx Anatomy 0.000 claims description 3
- 210000000088 lip Anatomy 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- 210000000496 pancreas Anatomy 0.000 claims description 3
- 201000010198 papillary carcinoma Diseases 0.000 claims description 3
- 210000002307 prostate Anatomy 0.000 claims description 3
- 201000010174 renal carcinoma Diseases 0.000 claims description 3
- 210000000813 small intestine Anatomy 0.000 claims description 3
- 210000002784 stomach Anatomy 0.000 claims description 3
- 210000001550 testis Anatomy 0.000 claims description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
- 210000001685 thyroid gland Anatomy 0.000 claims description 3
- 208000030901 thyroid gland follicular carcinoma Diseases 0.000 claims description 3
- 210000002105 tongue Anatomy 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
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 2
- 125000006591 (C2-C6) alkynylene group Chemical group 0.000 claims description 2
- 125000001724 1,2,3-oxadiazol-4-yl group Chemical group [H]C1=C(*)N=NO1 0.000 claims description 2
- 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
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000005879 dioxolanyl group Chemical group 0.000 claims description 2
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 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
- 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 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
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 7
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims 2
- 102000008135 Mechanistic Target of Rapamycin Complex 1 Human genes 0.000 claims 2
- 108010035196 Mechanistic Target of Rapamycin Complex 1 Proteins 0.000 claims 2
- 102000009308 Mechanistic Target of Rapamycin Complex 2 Human genes 0.000 claims 2
- 108010034057 Mechanistic Target of Rapamycin Complex 2 Proteins 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 239000002207 metabolite Substances 0.000 abstract description 23
- 201000010099 disease Diseases 0.000 abstract description 21
- 239000012453 solvate Substances 0.000 abstract description 17
- 230000011664 signaling Effects 0.000 abstract description 10
- 108091000080 Phosphotransferase Proteins 0.000 abstract description 4
- 102000020233 phosphotransferase Human genes 0.000 abstract description 4
- 230000008482 dysregulation Effects 0.000 abstract description 3
- 230000001404 mediated effect Effects 0.000 abstract description 3
- 230000019491 signal transduction Effects 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 description 220
- 238000003786 synthesis reaction Methods 0.000 description 219
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 194
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 156
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 61
- 238000005481 NMR spectroscopy Methods 0.000 description 54
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 44
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 41
- 239000000047 product Substances 0.000 description 39
- 238000005160 1H NMR spectroscopy Methods 0.000 description 37
- 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 group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCNC2 DXVKXAXORGPVCN-AWEZNQCLSA-N 0.000 description 35
- 238000009472 formulation Methods 0.000 description 35
- DYJGIDGBGYPXFJ-UHFFFAOYSA-N 4-(2-chloro-7-pyrimidin-2-yl-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-4-yl)morpholine Chemical compound N=1C(Cl)=NC=2CCN(C=3N=CC=CN=3)CCC=2C=1N1CCOCC1 DYJGIDGBGYPXFJ-UHFFFAOYSA-N 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 31
- 229940002612 prodrug Drugs 0.000 description 29
- 239000000651 prodrug Substances 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 239000004480 active ingredient Substances 0.000 description 27
- 239000007787 solid Substances 0.000 description 26
- 229910001868 water Inorganic materials 0.000 description 26
- 239000003112 inhibitor Substances 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 22
- 229940113083 morpholine Drugs 0.000 description 22
- 229910052799 carbon Inorganic materials 0.000 description 21
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 21
- 229910052698 phosphorus Inorganic materials 0.000 description 21
- 125000003342 alkenyl group Chemical group 0.000 description 20
- 229910052796 boron Inorganic materials 0.000 description 20
- 239000000460 chlorine Substances 0.000 description 20
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 19
- 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 19
- 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 18
- 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 18
- 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 18
- 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 17
- 125000000304 alkynyl group Chemical group 0.000 description 16
- 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 group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCNC2 PITUAFPHQAKRKP-UHFFFAOYSA-N 0.000 description 15
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-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
- IGSKHXTUVXSOMB-UHFFFAOYSA-N cyclopropylmethanamine Chemical compound NCC1CC1 IGSKHXTUVXSOMB-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- RMXILJIWTCNMMH-AWEZNQCLSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl]phenyl]urea Chemical group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CNCC2 RMXILJIWTCNMMH-AWEZNQCLSA-N 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 13
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 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
- 239000000243 solution Substances 0.000 description 13
- QCGMEWVZBGQOFN-UHFFFAOYSA-N 1,3-oxazole-5-carboxylic acid Chemical compound OC(=O)C1=CN=CO1 QCGMEWVZBGQOFN-UHFFFAOYSA-N 0.000 description 12
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 12
- 229960005419 nitrogen Drugs 0.000 description 12
- 229960002930 sirolimus Drugs 0.000 description 12
- 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 11
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 239000003795 chemical substances by application 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
- UNCQVRBWJWWJBF-UHFFFAOYSA-N 2-chloropyrimidine Chemical compound ClC1=NC=CC=N1 UNCQVRBWJWWJBF-UHFFFAOYSA-N 0.000 description 10
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-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
- 238000013459 approach Methods 0.000 description 10
- 239000004202 carbamide Substances 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- SMLBTEJFDUUUOL-UHFFFAOYSA-N tert-butyl 2-[4-(ethylcarbamoylamino)phenyl]-4-morpholin-4-yl-7,8-dihydro-5h-pyrido[4,3-d]pyrimidine-6-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(C(=O)OC(C)(C)C)CC2 SMLBTEJFDUUUOL-UHFFFAOYSA-N 0.000 description 10
- BRSJCUDFXDVXFP-UHFFFAOYSA-N 2-(4-aminophenyl)-6-benzyl-4-morpholin-4-yl-5h-pyrrolo[3,4-d]pyrimidin-7-one Chemical group C1=CC(N)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(CC=1C=CC=CC=1)C2=O BRSJCUDFXDVXFP-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical class [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 9
- 239000000969 carrier Substances 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 239000003826 tablet Substances 0.000 description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- 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 group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CNC2 ICPFKVCUIBCOAP-UHFFFAOYSA-N 0.000 description 8
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 8
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 101150041968 CDC13 gene Proteins 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 231100000252 nontoxic Toxicity 0.000 description 8
- 230000003000 nontoxic effect Effects 0.000 description 8
- 229910052701 rubidium Inorganic materials 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 229940079593 drug Drugs 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
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 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 7
- 238000004007 reversed phase HPLC Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 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 6
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 6
- 229910003827 NRaRb Inorganic materials 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- 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
- 125000002619 bicyclic group Chemical group 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 238000001727 in vivo Methods 0.000 description 6
- 239000000543 intermediate Substances 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
- VGPJCPSNRASZFH-UHFFFAOYSA-N tert-butyl 2-(4-aminophenyl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical group C1N(C(=O)OC(C)(C)C)CCC2=C1N=C(C=1C=CC(N)=CC=1)N=C2N1CCOCC1 VGPJCPSNRASZFH-UHFFFAOYSA-N 0.000 description 6
- 230000001225 therapeutic effect Effects 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
- PYEQIBJLQHFWDP-OGFXRTJISA-N (3s)-3-propan-2-ylmorpholine;hydrobromide Chemical compound Br.CC(C)[C@H]1COCCN1 PYEQIBJLQHFWDP-OGFXRTJISA-N 0.000 description 5
- LNDFOZVERUIHGC-UHFFFAOYSA-N 1-[4-(6-benzoyl-4-morpholin-4-yl-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-yl)phenyl]-3-ethylurea Chemical group 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 5
- 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 5
- 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 5
- 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 5
- 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 5
- XBGOWDJFVNGPHG-UQKRIMTDSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-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=C1N2[C@H](COCC2)C)=NC2=C1CCNC2 XBGOWDJFVNGPHG-UQKRIMTDSA-N 0.000 description 5
- 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 5
- 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 group 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 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
- 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 group 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 5
- 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 5
- 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 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 5
- 108091007960 PI3Ks Proteins 0.000 description 5
- 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 description 5
- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 239000006071 cream Substances 0.000 description 5
- 238000003818 flash chromatography Methods 0.000 description 5
- 125000001841 imino group Chemical group [H]N=* 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 238000012986 modification Methods 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
- 238000002560 therapeutic procedure Methods 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- SFWWGMKXCYLZEG-YFKPBYRVSA-N (3s)-3-methylmorpholine Chemical compound C[C@H]1COCCN1 SFWWGMKXCYLZEG-YFKPBYRVSA-N 0.000 description 4
- 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 group C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCC(F)F)=CC=2)=NC2=C1CNCC2 QCISZMOMTHHKKA-ZDUSSCGKSA-N 0.000 description 4
- 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 4
- 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 4
- 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 4
- 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 group 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 4
- 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 4
- 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 4
- 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 4
- 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 4
- 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 4
- 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 4
- ZCUBGPIXAMSJIP-KRWDZBQOSA-N 1-cyclobutyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(1,3-oxazole-5-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=1OC=NC=1)CC2 ZCUBGPIXAMSJIP-KRWDZBQOSA-N 0.000 description 4
- ZYRUJDSQBZIRCB-KRWDZBQOSA-N 1-cyclobutyl-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)NC3CCC3)=CC=2)=NC2=C1CN(C(=O)C=1SC=CN=1)CC2 ZYRUJDSQBZIRCB-KRWDZBQOSA-N 0.000 description 4
- 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 4
- 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 4
- 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 4
- 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 group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(C=1N=CC=CN=1)C2 ZXQOTUSTYCUIBX-UHFFFAOYSA-N 0.000 description 4
- 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 group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CN=CC=1)C2 AIIRZUPOXXVTIM-UHFFFAOYSA-N 0.000 description 4
- DXVKXAXORGPVCN-CQSZACIVSA-N 1-ethyl-3-[4-[4-[(3r)-3-methylmorpholin-4-yl]-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@@H](COCC2)C)=NC2=C1CCNC2 DXVKXAXORGPVCN-CQSZACIVSA-N 0.000 description 4
- RMXILJIWTCNMMH-CQSZACIVSA-N 1-ethyl-3-[4-[4-[(3r)-3-methylmorpholin-4-yl]-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl]phenyl]urea Chemical group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@@H](COCC2)C)=NC2=C1CNCC2 RMXILJIWTCNMMH-CQSZACIVSA-N 0.000 description 4
- 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 4
- 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 4
- 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 4
- 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 group 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 4
- 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 4
- 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 group 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 4
- 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 4
- 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 4
- 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 4
- 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 group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CN(C1COC1)CC2 GKVOTXQBCIYYJV-INIZCTEOSA-N 0.000 description 4
- 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 4
- 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 4
- 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 4
- 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 4
- 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 4
- 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 4
- 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 group 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 4
- 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 4
- 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 4
- 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 4
- 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 4
- 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 4
- 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 4
- 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 group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)C1(C)CC1)C2 FXMGSWKMLDLHHE-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 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 4
- 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 4
- 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 4
- 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 4
- 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 4
- 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 4
- 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 4
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 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 group 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 4
- 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 group 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 4
- UZGLOGCJCWBBIV-UHFFFAOYSA-N 3-(chloromethyl)pyridin-1-ium;chloride Chemical compound Cl.ClCC1=CC=CN=C1 UZGLOGCJCWBBIV-UHFFFAOYSA-N 0.000 description 4
- 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 group C1N(C(C)C)CCC2=C1N=C(C=1C=NC(N)=NC=1)N=C2N1CCOC[C@@H]1C BEXAKUWVGIIQKQ-ZDUSSCGKSA-N 0.000 description 4
- 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 group 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 4
- 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 4
- 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 group 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 4
- 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 4
- 230000007730 Akt signaling Effects 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
- 241000282412 Homo Species 0.000 description 4
- 108010000817 Leuprolide Proteins 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
- 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
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
- 229930006000 Sucrose Natural products 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
- 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
- 230000001594 aberrant effect Effects 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
- 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
- 239000007900 aqueous suspension Substances 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 238000002648 combination therapy Methods 0.000 description 4
- 239000013058 crude material Substances 0.000 description 4
- 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 group 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 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
- 235000019197 fats Nutrition 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
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 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 4
- 239000003094 microcapsule Substances 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
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 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
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 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
- 208000024891 symptom Diseases 0.000 description 4
- 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 group 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 4
- 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 group 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 4
- NLPOHPJVDDEGHU-QGZVFWFLSA-N tert-butyl 2-[4-(ethylcarbamoylamino)phenyl]-4-[(3r)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@@H](COCC2)C)=NC2=C1CCN(C(=O)OC(C)(C)C)C2 NLPOHPJVDDEGHU-QGZVFWFLSA-N 0.000 description 4
- HMKOBOLUIOUHOS-QGZVFWFLSA-N tert-butyl 2-[4-(ethylcarbamoylamino)phenyl]-4-[(3r)-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)C)CC2 HMKOBOLUIOUHOS-QGZVFWFLSA-N 0.000 description 4
- WVVAQMKMASYMOW-FQEVSTJZSA-N tert-butyl 2-[4-(ethylcarbamoylamino)phenyl]-4-[(3s)-3-ethylmorpholin-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)CC)=NC2=C1CCN(C(=O)OC(C)(C)C)C2 WVVAQMKMASYMOW-FQEVSTJZSA-N 0.000 description 4
- 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 4
- 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 4
- 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 group 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 4
- 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 4
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 4
- 239000003981 vehicle Substances 0.000 description 4
- 239000003039 volatile agent Substances 0.000 description 4
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 3
- 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
- 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 3
- HKZCFGQSWLWNQA-UHFFFAOYSA-N 1,3-thiazole-2-carbonyl chloride Chemical compound ClC(=O)C1=NC=CS1 HKZCFGQSWLWNQA-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- 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 group 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 3
- FNEQBMPZQMEHDM-KRWDZBQOSA-N 1-ethyl-3-[4-[4-[(3s)-3-ethylmorpholin-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)CC)=NC2=C1CCNC2 FNEQBMPZQMEHDM-KRWDZBQOSA-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 group 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
- OVIDHWMXFBKIOS-KRWDZBQOSA-N 1-ethyl-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)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=CN=CC=1)C2 OVIDHWMXFBKIOS-KRWDZBQOSA-N 0.000 description 3
- 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 3
- JUTGFKKDKHHONK-KRWDZBQOSA-N 2-[2-[4-(ethylcarbamoylamino)phenyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-n,n-dimethylacetamide Chemical group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC(=O)N(C)C)C2 JUTGFKKDKHHONK-KRWDZBQOSA-N 0.000 description 3
- 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 3
- GELVZYOEQVJIRR-UHFFFAOYSA-N 2-chloropyrazine Chemical compound ClC1=CN=CC=N1 GELVZYOEQVJIRR-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 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 3
- 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 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
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- 208000024172 Cardiovascular disease Diseases 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
- 206010014759 Endometrial neoplasm Diseases 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 102000009465 Growth Factor Receptors Human genes 0.000 description 3
- 108010009202 Growth Factor Receptors Proteins 0.000 description 3
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 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
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 108010006877 Tacrolimus Binding Protein 1A Proteins 0.000 description 3
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 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
- 229960000583 acetic acid Drugs 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
- 150000001408 amides Chemical class 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
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
- 239000000872 buffer Substances 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
- 230000010261 cell growth Effects 0.000 description 3
- 230000005754 cellular signaling Effects 0.000 description 3
- 238000002512 chemotherapy Methods 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- KZZKOVLJUKWSKX-UHFFFAOYSA-N cyclobutanamine Chemical compound NC1CCC1 KZZKOVLJUKWSKX-UHFFFAOYSA-N 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
- SLIKWVTWIGHFJE-UHFFFAOYSA-N diphenoxymethylidenecyanamide Chemical compound C=1C=CC=CC=1OC(=NC#N)OC1=CC=CC=C1 SLIKWVTWIGHFJE-UHFFFAOYSA-N 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 229940088598 enzyme Drugs 0.000 description 3
- AAKJLRGGTJKAMG-UHFFFAOYSA-N erlotinib Chemical compound C=12C=C(OCCOC)C(OCCOC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 AAKJLRGGTJKAMG-UHFFFAOYSA-N 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
- 239000000796 flavoring agent Substances 0.000 description 3
- 229960002074 flutamide Drugs 0.000 description 3
- 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 3
- 235000013355 food flavoring agent Nutrition 0.000 description 3
- 235000003599 food sweetener Nutrition 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
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- GFIJNRVAKGFPGQ-LIJARHBVSA-N leuprolide Chemical compound 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 GFIJNRVAKGFPGQ-LIJARHBVSA-N 0.000 description 3
- 229960004338 leuprorelin Drugs 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 239000003628 mammalian target of rapamycin inhibitor Substances 0.000 description 3
- 230000002503 metabolic effect Effects 0.000 description 3
- 230000004060 metabolic process Effects 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
- 238000002156 mixing Methods 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
- 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
- 230000008569 process Effects 0.000 description 3
- 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 3
- 235000018102 proteins Nutrition 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 235000017550 sodium carbonate Nutrition 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 239000003765 sweetening agent Substances 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- 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 group 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 3
- ZBHMIZVRJZFENC-UHFFFAOYSA-N tert-butyl 2,4-dichloro-8-oxo-5,6-dihydropyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound N1=C(Cl)N=C2C(=O)N(C(=O)OC(C)(C)C)CCC2=C1Cl ZBHMIZVRJZFENC-UHFFFAOYSA-N 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 group 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
- ODAXEZVHUVQDSG-UHFFFAOYSA-N tert-butyl 2-[4-[(3-chlorophenyl)carbamoylamino]phenyl]-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(NC(=O)NC=3C=C(Cl)C=CC=3)=CC=1)N=C2N1CCOCC1 ODAXEZVHUVQDSG-UHFFFAOYSA-N 0.000 description 3
- SCECFHIIYVDCSA-UHFFFAOYSA-N tert-butyl 2-chloro-4-(3,6-dihydro-2h-pyran-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(Cl)N=C2C1=CCOCC1 SCECFHIIYVDCSA-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- 239000001993 wax Substances 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
- 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 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
- 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
- KUGYCHLSGIIOHV-ZRCAFCQKSA-N 1-[(1s,2s)-2-hydroxycyclopentyl]-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)N[C@@H]3[C@H](CCC3)O)=CC=2)=NC2=C1CCNC2 KUGYCHLSGIIOHV-ZRCAFCQKSA-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
- 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 2
- 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 2
- 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 2
- 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 2
- KWRMWSOLLBNFMI-YMXDCFFPSA-N 1-[4-[7-(5,5-dimethyloxolan-3-yl)-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C1CC(C)(C)OC1)C2 KWRMWSOLLBNFMI-YMXDCFFPSA-N 0.000 description 2
- 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 2
- 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 2
- 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 group C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2CCOCC2)=C(CCNC2=O)C2=N1 IXLNEPGLJLXCQL-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
- 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 2
- 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 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
- 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 group 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
- RHBCJIOPYOFMIJ-UHFFFAOYSA-N 1-ethyl-3-[4-[4-morpholin-4-yl-7-(pyridine-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=CC=1)C2 RHBCJIOPYOFMIJ-UHFFFAOYSA-N 0.000 description 2
- ALRSFZUTVHDFMT-UHFFFAOYSA-N 1-ethyl-3-[4-[6-[(3-hydroxyphenyl)methyl]-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(CC=1C=C(O)C=CC=1)C2 ALRSFZUTVHDFMT-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
- 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 group 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 2
- UXMVBMILZYUHQN-HRAATJIYSA-N 1-ethyl-3-[4-[7-[(2r)-2-hydroxybutanoyl]-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)CC)C2 UXMVBMILZYUHQN-HRAATJIYSA-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
- OQURWGJAWSLGQG-UHFFFAOYSA-N 1-isocyanatopropane Chemical compound CCCN=C=O OQURWGJAWSLGQG-UHFFFAOYSA-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
- OZJZCCMIOZPPIT-UHFFFAOYSA-N 2-(2-methoxyethoxy)acetyl chloride Chemical compound COCCOCC(Cl)=O OZJZCCMIOZPPIT-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
- OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical compound ClC1=CC=CC=N1 OKDGRDCXVWSXDC-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
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 2
- ROADCYAOHVSOLQ-UHFFFAOYSA-N 3-oxetanone Chemical compound O=C1COC1 ROADCYAOHVSOLQ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- GDZNUFZXDSVZSU-UHFFFAOYSA-N 4-(4-morpholin-4-yl-6-pyrimidin-2-yl-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl)aniline Chemical compound C1=CC(N)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(C=1N=CC=CN=1)CC2 GDZNUFZXDSVZSU-UHFFFAOYSA-N 0.000 description 2
- NQKSDOBDIQZLNX-UHFFFAOYSA-N 4-[2-(1h-indazol-5-yl)-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-4-yl]morpholine Chemical group C1COCCN1C1=NC(C=2C=C3C=NNC3=CC=2)=NC2=C1CCN(C=1N=CC=CN=1)C2 NQKSDOBDIQZLNX-UHFFFAOYSA-N 0.000 description 2
- WTDUQQXDOAPXAQ-UHFFFAOYSA-N 4-chloro-2-methoxypyridine Chemical compound COC1=CC(Cl)=CC=N1 WTDUQQXDOAPXAQ-UHFFFAOYSA-N 0.000 description 2
- WDTVJRYCMIZPMX-UHFFFAOYSA-N 4-chloro-2-methylpyrimidine Chemical compound CC1=NC=CC(Cl)=N1 WDTVJRYCMIZPMX-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
- 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 group 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
- 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 2
- VYVJHDWZXQWAFS-UHFFFAOYSA-N 6-benzyl-2,4-dichloro-7,8-dihydro-5h-pyrido[4,3-d]pyrimidine Chemical compound C1CC2=NC(Cl)=NC(Cl)=C2CN1CC1=CC=CC=C1 VYVJHDWZXQWAFS-UHFFFAOYSA-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
- 208000024827 Alzheimer disease Diseases 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-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
- 108010006654 Bleomycin Proteins 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
- OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 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
- 241000282693 Cercopithecidae Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 206010009944 Colon cancer 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
- 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 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
- 206010061818 Disease progression Diseases 0.000 description 2
- 206010014733 Endometrial cancer Diseases 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-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
- 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
- 108090000100 Hepatocyte Growth Factor Proteins 0.000 description 2
- 102100021866 Hepatocyte growth factor Human genes 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-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
- 102000000588 Interleukin-2 Human genes 0.000 description 2
- 108010002350 Interleukin-2 Proteins 0.000 description 2
- 208000008839 Kidney Neoplasms Diseases 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
- 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
- 102000046985 LST8 Homolog mTOR Associated Human genes 0.000 description 2
- GQYIWUVLTXOXAJ-UHFFFAOYSA-N Lomustine Chemical compound ClCCN(N=O)C(=O)NC1CCCCC1 GQYIWUVLTXOXAJ-UHFFFAOYSA-N 0.000 description 2
- 206010058467 Lung neoplasm malignant Diseases 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
- 229930195725 Mannitol Natural products 0.000 description 2
- 101500025412 Mus musculus Processed cyclic AMP-responsive element-binding protein 3-like protein 1 Proteins 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
- QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 2
- 208000012902 Nervous system disease Diseases 0.000 description 2
- 208000025966 Neurological disease Diseases 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 229930012538 Paclitaxel Natural products 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 2
- 206010060862 Prostate cancer Diseases 0.000 description 2
- 208000000236 Prostatic Neoplasms Diseases 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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 208000005718 Stomach Neoplasms Diseases 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 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
- 229920001615 Tragacanth Polymers 0.000 description 2
- 229940122803 Vinca alkaloid Drugs 0.000 description 2
- 238000010521 absorption reaction Methods 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
- 150000007513 acids Chemical class 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- 239000008186 active pharmaceutical agent 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
- 238000012382 advanced drug delivery Methods 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 125000004419 alkynylene group Chemical group 0.000 description 2
- 125000000266 alpha-aminoacyl group Chemical group 0.000 description 2
- 229960000473 altretamine Drugs 0.000 description 2
- 229960003437 aminoglutethimide Drugs 0.000 description 2
- ROBVIMPUHSLWNV-UHFFFAOYSA-N aminoglutethimide Chemical compound C=1C=C(N)C=CC=1C1(CC)CCC(=O)NC1=O ROBVIMPUHSLWNV-UHFFFAOYSA-N 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
- 230000000340 anti-metabolite 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
- 229940100197 antimetabolite Drugs 0.000 description 2
- 239000002256 antimetabolite Substances 0.000 description 2
- 239000003080 antimitotic agent Substances 0.000 description 2
- 229940045719 antineoplastic alkylating agent nitrosoureas Drugs 0.000 description 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 2
- 229960003121 arginine Drugs 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
- 125000004321 azepin-2-yl group Chemical group [H]N1C([H])=C([H])C([H])=C([H])C([H])=C1* 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
- OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical class 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
- LYYAPEYYOHSTHY-UHFFFAOYSA-N butyl n-[4-[4-morpholin-4-yl-7-(4-phenylpyrimidin-2-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCCCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=C(C=CN=1)C=1C=CC=CC=1)C2 LYYAPEYYOHSTHY-UHFFFAOYSA-N 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
- 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
- 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
- 230000004663 cell proliferation Effects 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
- 229960004630 chlorambucil Drugs 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
- 229940125904 compound 1 Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 229960004397 cyclophosphamide Drugs 0.000 description 2
- 239000000824 cytostatic agent Substances 0.000 description 2
- 231100000433 cytotoxic Toxicity 0.000 description 2
- 230000001472 cytotoxic effect Effects 0.000 description 2
- 239000003405 delayed action preparation Substances 0.000 description 2
- 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 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
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000005750 disease progression Effects 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 238000009826 distribution Methods 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
- 150000002148 esters Chemical class 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
- 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
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 2
- 206010017758 gastric cancer Diseases 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
- 229960002584 gefitinib Drugs 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
- 238000010914 gene-directed enzyme pro-drug therapy Methods 0.000 description 2
- 235000011187 glycerol Nutrition 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
- 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
- 229910000042 hydrogen bromide Inorganic materials 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
- BNTRVUUJBGBGLZ-UHFFFAOYSA-N hydron;pyridine-4-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=NC=C1 BNTRVUUJBGBGLZ-UHFFFAOYSA-N 0.000 description 2
- 230000037417 hyperactivation Effects 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
- 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
- 201000010982 kidney cancer Diseases 0.000 description 2
- 229940043355 kinase inhibitor Drugs 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 125000005647 linker group Chemical group 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
- 239000012931 lyophilized formulation 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
- 235000010355 mannitol Nutrition 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 229960004961 mechlorethamine Drugs 0.000 description 2
- HAWPXGHAZFHHAD-UHFFFAOYSA-N mechlorethamine Chemical compound ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 description 2
- 229960004296 megestrol acetate Drugs 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
- 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
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 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 2
- XOGAMPZSMNBPGH-UHFFFAOYSA-N methyl 2-[4-(ethylcarbamoylamino)phenyl]-4-morpholin-4-yl-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylate Chemical group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(C(=O)OC)C2 XOGAMPZSMNBPGH-UHFFFAOYSA-N 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
- 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
- 229960001156 mitoxantrone Drugs 0.000 description 2
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical class CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 2
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 2
- 239000000346 nonvolatile oil Substances 0.000 description 2
- 239000003883 ointment base 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
- 239000012074 organic phase Substances 0.000 description 2
- 230000002018 overexpression Effects 0.000 description 2
- OJEOJUQOECNDND-UHFFFAOYSA-N oxetan-3-amine Chemical compound NC1COC1 OJEOJUQOECNDND-UHFFFAOYSA-N 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
- 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
- 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 2
- 239000010452 phosphate 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
- 239000003757 phosphotransferase inhibitor Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 230000004962 physiological condition 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
- 229920000642 polymer Polymers 0.000 description 2
- 229920001184 polypeptide Chemical group 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 108090000765 processed proteins & peptides Chemical group 0.000 description 2
- 102000004196 processed proteins & peptides Human genes 0.000 description 2
- 239000000583 progesterone congener Substances 0.000 description 2
- 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 2
- 238000011321 prophylaxis Methods 0.000 description 2
- 150000003212 purines Chemical class 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003235 pyrrolidines Chemical class 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 238000001959 radiotherapy Methods 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 102000005962 receptors Human genes 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
- 239000011369 resultant mixture Substances 0.000 description 2
- 125000006413 ring segment Chemical group 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
- 229910052710 silicon Inorganic materials 0.000 description 2
- 229910052708 sodium 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
- 208000017572 squamous cell neoplasm Diseases 0.000 description 2
- 201000011549 stomach cancer Diseases 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
- 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
- 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
- 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 2
- 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 group 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 2
- FYENGIZLDIXPSB-UHFFFAOYSA-N tert-butyl 2-[4-(ethylcarbamoylamino)phenyl]-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)OC(C)(C)C)C2 FYENGIZLDIXPSB-UHFFFAOYSA-N 0.000 description 2
- NJUGYZMTYXWULM-UHFFFAOYSA-N tert-butyl 2-chloro-4-morpholin-4-yl-7,8-dihydro-5h-pyrido[4,3-d]pyrimidine-6-carboxylate Chemical compound C=12CN(C(=O)OC(C)(C)C)CCC2=NC(Cl)=NC=1N1CCOCC1 NJUGYZMTYXWULM-UHFFFAOYSA-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 group 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
- 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
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 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
- 238000002054 transplantation Methods 0.000 description 2
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 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
- 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
- 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 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
- 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
- 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
- LJRDOKAZOAKLDU-UDXJMMFXSA-N (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(2r,3s,4r,5s)-5-[(1r,2r,3s,5r,6s)-3,5-diamino-2-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol;sulfuric ac Chemical compound OS(O)(=O)=O.N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO LJRDOKAZOAKLDU-UDXJMMFXSA-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 group 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
- 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
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-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
- WOGITNXCNOTRLK-VOTSOKGWSA-N (e)-3-phenylprop-2-enoyl chloride Chemical compound ClC(=O)\C=C\C1=CC=CC=C1 WOGITNXCNOTRLK-VOTSOKGWSA-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
- 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
- RKOUFQLNMRAACI-UHFFFAOYSA-N 1,1,1-trifluoro-2-iodoethane Chemical compound FC(F)(F)CI RKOUFQLNMRAACI-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
- ABXJCMCHRYJITH-UHFFFAOYSA-N 1,1-dimethyl-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)N(C)C)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CC=CN=1)C2 ABXJCMCHRYJITH-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
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RHFWLPWDOYJEAL-UHFFFAOYSA-N 1,2-oxazol-3-amine Chemical compound NC=1C=CON=1 RHFWLPWDOYJEAL-UHFFFAOYSA-N 0.000 description 1
- NEUOVUKOIWZBMH-UHFFFAOYSA-N 1,3-dimethyl-6-[4-(4-morpholin-4-yl-7-pyrimidin-2-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)anilino]pyrimidine-2,4-dione Chemical group O=C1N(C)C(=O)N(C)C(NC=2C=CC(=CC=2)C=2N=C(C=3CCN(CC=3N=2)C=2N=CC=CN=2)N2CCOCC2)=C1 NEUOVUKOIWZBMH-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- CQHYICHMGNSGQH-UHFFFAOYSA-N 1,3-oxazole-2-carboxylic acid Chemical compound OC(=O)C1=NC=CO1 CQHYICHMGNSGQH-UHFFFAOYSA-N 0.000 description 1
- YHIIJNLSGULWAA-UHFFFAOYSA-N 1,4-thiazinane 1-oxide Chemical compound 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
- 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
- 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 group 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 group 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 group C1=CC(NC(=O)NCCO)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CC=CN=1)C2 SYCDSFNZKJRMOZ-UHFFFAOYSA-N 0.000 description 1
- FYBANXJYXOESHM-AWEZNQCLSA-N 1-(2-hydroxyethyl)-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)NCCO)=CC=2)=NC2=C1CNCC2 FYBANXJYXOESHM-AWEZNQCLSA-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
- ZRFHJLGIHVRHJM-UHFFFAOYSA-N 1-(3-methyl-1,2-oxazol-5-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 O1N=C(C)C=C1NC(=O)NC1=CC=C(C=2N=C(C=3CCN(CC=3N=2)C=2N=CC=CN=2)N2CCOCC2)C=C1 ZRFHJLGIHVRHJM-UHFFFAOYSA-N 0.000 description 1
- MFYDBUFMJMVTIT-UHFFFAOYSA-N 1-(5-methyl-1,2-oxazol-3-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 O1C(C)=CC(NC(=O)NC=2C=CC(=CC=2)C=2N=C(C=3CCN(CC=3N=2)C=2N=CC=CN=2)N2CCOCC2)=N1 MFYDBUFMJMVTIT-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 group 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 group 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 group 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 group 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
- DPFTWJSXPSZNKS-UHFFFAOYSA-N 1-[4-(7-benzyl-4-morpholin-4-yl-5,6,8,9-tetrahydropyrimido[4,5-d]azepin-2-yl)phenyl]-3-ethylurea Chemical group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(CC=1C=CC=CC=1)CC2 DPFTWJSXPSZNKS-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
- HARAFAORTBTUMX-GOSISDBHSA-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-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN1C(=O)CC[C@@H]12 HARAFAORTBTUMX-GOSISDBHSA-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 group 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
- 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
- FIYQHTZROQXJCR-QGZVFWFLSA-N 1-[4-[(8r)-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)[C@@H]2C FIYQHTZROQXJCR-QGZVFWFLSA-N 0.000 description 1
- MQKMGSDPZMHVML-QGZVFWFLSA-N 1-[4-[(8r)-7-(2,6-dimethoxypyrimidin-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(OC)N=C(OC)C=1)[C@@H]2C MQKMGSDPZMHVML-QGZVFWFLSA-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
- FRUQUVXWHBMUBQ-QGZVFWFLSA-N 1-[4-[(8r)-7-(2-chloro-6-methylpyrimidin-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(Cl)N=C(C)C=1)[C@@H]2C FRUQUVXWHBMUBQ-QGZVFWFLSA-N 0.000 description 1
- AFVBLDYMJMROCL-QGZVFWFLSA-N 1-[4-[(8r)-7-(4-chloro-6-methylpyrimidin-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=C(Cl)C=C(C)N=1)[C@@H]2C AFVBLDYMJMROCL-QGZVFWFLSA-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
- LPMHDUQGEFMAGB-JKSUJKDBSA-N 1-[4-[(8r)-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 group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(C)=O)[C@@H]2C LPMHDUQGEFMAGB-JKSUJKDBSA-N 0.000 description 1
- NDPPHNMVTDSAFU-HNAYVOBHSA-N 1-[4-[(8r)-8-(cyanomethyl)-4-[(3s)-3-methylmorpholin-4-yl]-5,6,7,8-tetrahydropyrido[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@@H]2CC#N NDPPHNMVTDSAFU-HNAYVOBHSA-N 0.000 description 1
- UTMQCXASYVLQBJ-PGRDOPGGSA-N 1-[4-[(8r)-8-(cyanomethyl)-4-[(3s)-3-methylmorpholin-4-yl]-7-propan-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=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(C)C)[C@@H]2CC#N UTMQCXASYVLQBJ-PGRDOPGGSA-N 0.000 description 1
- KAOQIYYLGAOMIG-LAUBAEHRSA-N 1-[4-[(8r)-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-LAUBAEHRSA-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
- FIYQHTZROQXJCR-KRWDZBQOSA-N 1-[4-[(8s)-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)[C@H]2C FIYQHTZROQXJCR-KRWDZBQOSA-N 0.000 description 1
- MQKMGSDPZMHVML-KRWDZBQOSA-N 1-[4-[(8s)-7-(2,6-dimethoxypyrimidin-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(OC)N=C(OC)C=1)[C@H]2C MQKMGSDPZMHVML-KRWDZBQOSA-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
- FRUQUVXWHBMUBQ-KRWDZBQOSA-N 1-[4-[(8s)-7-(2-chloro-6-methylpyrimidin-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(Cl)N=C(C)C=1)[C@H]2C FRUQUVXWHBMUBQ-KRWDZBQOSA-N 0.000 description 1
- AFVBLDYMJMROCL-KRWDZBQOSA-N 1-[4-[(8s)-7-(4-chloro-6-methylpyrimidin-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=C(Cl)C=C(C)N=1)[C@H]2C AFVBLDYMJMROCL-KRWDZBQOSA-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
- NDPPHNMVTDSAFU-KXBFYZLASA-N 1-[4-[(8s)-8-(cyanomethyl)-4-[(3s)-3-methylmorpholin-4-yl]-5,6,7,8-tetrahydropyrido[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@H]2CC#N NDPPHNMVTDSAFU-KXBFYZLASA-N 0.000 description 1
- UTMQCXASYVLQBJ-AVRDEDQJSA-N 1-[4-[(8s)-8-(cyanomethyl)-4-[(3s)-3-methylmorpholin-4-yl]-7-propan-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=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(C)C)[C@H]2CC#N UTMQCXASYVLQBJ-AVRDEDQJSA-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 group 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
- 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
- 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
- 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 group 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
- 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
- CDCYWCCVSSVXMG-HNNXBMFYSA-N 1-[4-[6-cyclopropylsulfonyl-4-[(3s)-3-methylmorpholin-4-yl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CN(S(=O)(=O)C1CC1)C2 CDCYWCCVSSVXMG-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
- 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
- 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
- MLIGTOZJKGBENW-UHFFFAOYSA-N 1-[4-[7-(2,2-dimethylpropanoyl)-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(C)(C)C)C2 MLIGTOZJKGBENW-UHFFFAOYSA-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
- 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 group 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
- 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 group 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 group 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
- RKWLPWYDDRMAMC-QFBILLFUSA-N 1-[4-[7-[(2r)-2,3-dihydroxypropyl]-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](O)CO)C2 RKWLPWYDDRMAMC-QFBILLFUSA-N 0.000 description 1
- KGSRWHXYSLRQGX-OXJNMPFZSA-N 1-[4-[7-[(2r)-2-aminobutanoyl]-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](N)CC)C2 KGSRWHXYSLRQGX-OXJNMPFZSA-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
- KGSRWHXYSLRQGX-JXFKEZNVSA-N 1-[4-[7-[(2s)-2-aminobutanoyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(=O)[C@@H](N)CC)C2 KGSRWHXYSLRQGX-JXFKEZNVSA-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 group 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 group 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
- ODWGIJXBRTYRIK-SFHVURJKSA-N 1-[4-[7-[2-(dimethylamino)pyrimidin-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=CC=1)N(C)C)C2 ODWGIJXBRTYRIK-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 group 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
- 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 group 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
- KXTVXJQQSPKFQK-SFHVURJKSA-N 1-[4-[7-ethyl-4-[(3s)-3-ethylmorpholin-4-yl]-8-oxo-5,6-dihydropyrido[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(CC)C2=O KXTVXJQQSPKFQK-SFHVURJKSA-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 group 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 group 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
- NNFOVLFUGLWWCL-UHFFFAOYSA-N 1-acetylpiperidin-4-one Chemical compound CC(=O)N1CCC(=O)CC1 NNFOVLFUGLWWCL-UHFFFAOYSA-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 group 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 group 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
- 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
- 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
- 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
- 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
- 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
- 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 group 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
- 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
- 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 group 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
- 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
- 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 group 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
- SWIMSWBWEIBPMI-QGZVFWFLSA-N 1-ethyl-3-[4-[(8r)-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)[C@@H]2C SWIMSWBWEIBPMI-QGZVFWFLSA-N 0.000 description 1
- RBMNUMNJWJQJDN-GOSISDBHSA-N 1-ethyl-3-[4-[(8r)-8-methyl-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)[C@@H]2C RBMNUMNJWJQJDN-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 group 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 group 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 group 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
- SWIMSWBWEIBPMI-KRWDZBQOSA-N 1-ethyl-3-[4-[(8s)-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)[C@H]2C SWIMSWBWEIBPMI-KRWDZBQOSA-N 0.000 description 1
- RBMNUMNJWJQJDN-SFHVURJKSA-N 1-ethyl-3-[4-[(8s)-8-methyl-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)[C@H]2C RBMNUMNJWJQJDN-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
- GJDFCKHPPRPJCC-UHFFFAOYSA-N 1-ethyl-3-[4-[4-(1,4-oxazepan-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=C1N2CCOCCC2)=NC2=C1CCN(C=1N=CC=CN=1)CC2 GJDFCKHPPRPJCC-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 group 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
- AOZZVSNHLHYTPP-UGNFMNBCSA-N 1-ethyl-3-[4-[4-(3-methylmorpholin-4-yl)-7-[(2s)-oxolane-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=C1N2C(COCC2)C)=NC2=C1CCN(C(=O)[C@H]1OCCC1)C2 AOZZVSNHLHYTPP-UGNFMNBCSA-N 0.000 description 1
- JGOMMAYWJZYGEG-NNBQYGFHSA-N 1-ethyl-3-[4-[4-(3-methylmorpholin-4-yl)-7-[(3s)-oxolane-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=C1N2C(COCC2)C)=NC2=C1CCN(C(=O)[C@@H]1COCC1)C2 JGOMMAYWJZYGEG-NNBQYGFHSA-N 0.000 description 1
- CVPCKNSMNDCNND-UHFFFAOYSA-N 1-ethyl-3-[4-[4-(4-morpholin-4-ylpyridine-2-carbonyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl]phenyl]urea Chemical group C1=CC(NC(=O)NCC)=CC=C1C(N=C1C(=O)C=2N=CC=C(C=2)N2CCOCC2)=NC2=C1CNCC2 CVPCKNSMNDCNND-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 group 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 group 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
- 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
- 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 group 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
- 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 group 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
- 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
- TVYBHRVHBDROCJ-INIZCTEOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylpyrimidin-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(C)N=CC=1)C2 TVYBHRVHBDROCJ-INIZCTEOSA-N 0.000 description 1
- KJWXZOMDTLCUSX-KRWDZBQOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(6-methylpyrimidin-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=CN=C(C)C=1)C2 KJWXZOMDTLCUSX-KRWDZBQOSA-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
- 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
- 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 group 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
- IXXADZGWCMOVOD-KRWDZBQOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(2-methylsulfonylethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CCS(C)(=O)=O)C2 IXXADZGWCMOVOD-KRWDZBQOSA-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 group 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
- 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
- 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 group 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 group 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 group 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
- 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
- KZXJTAHMWTYOGU-PBVYKCSPSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(pyrrolidine-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)C1NCCC1)C2 KZXJTAHMWTYOGU-PBVYKCSPSA-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
- 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
- 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 group 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
- CYPSVXZNTGLADU-SFHVURJKSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-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=C1N2[C@H](COCC2)C)=NC2=C1CCN(C=1N=CC=CN=1)CC2 CYPSVXZNTGLADU-SFHVURJKSA-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 group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C1CNCC1)C2 HRMYKZJADLVFPF-DIMJTDRSSA-N 0.000 description 1
- AWEVQOHMVOACQS-INIZCTEOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-8-oxo-5,6-dihydropyrimido[4,5-a]quinolizin-2-yl]phenyl]urea Chemical group C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2[C@H](COCC2)C)=C(CCN2C(C=CC=C22)=O)C2=N1 AWEVQOHMVOACQS-INIZCTEOSA-N 0.000 description 1
- BYDCZUUNGIVWGC-ZDUSSCGKSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-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(N2[C@H](COCC2)C)=C(CCNC2=O)C2=N1 BYDCZUUNGIVWGC-ZDUSSCGKSA-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
- QQGRITSLMPKOBG-UHFFFAOYSA-N 1-ethyl-3-[4-[4-[2-(methoxymethyl)morpholin-4-yl]-7-methyl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CC(COC)OCC2)=NC2=C1CCN(C)C2 QQGRITSLMPKOBG-UHFFFAOYSA-N 0.000 description 1
- OFSVUGVOMXASBN-UHFFFAOYSA-N 1-ethyl-3-[4-[4-morpholin-4-yl-6-(2-phenylacetyl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl]phenyl]urea Chemical group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(C(=O)CC=1C=CC=CC=1)CC2 OFSVUGVOMXASBN-UHFFFAOYSA-N 0.000 description 1
- LBDCHTICVGQMJM-UHFFFAOYSA-N 1-ethyl-3-[4-[4-morpholin-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=C1N2CCOCC2)=NC2=C1CN(C(=O)C=1C=NC=CC=1)CC2 LBDCHTICVGQMJM-UHFFFAOYSA-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
- 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 group 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 group 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
- 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
- WALBKOCRCVWLLL-UHFFFAOYSA-N 1-ethyl-3-[4-[4-morpholin-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=C1N2CCOCC2)=NC2=C1CCN(C(=O)C=1C=NC=CC=1)C2 WALBKOCRCVWLLL-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 group 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
- 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
- ZYHAGPGMEHUNFO-UHFFFAOYSA-N 1-ethyl-3-[4-[6-[(4-methoxyphenyl)methyl]-4-morpholin-4-yl-7-oxo-5h-pyrrolo[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(CC=1C=CC(OC)=CC=1)C2=O ZYHAGPGMEHUNFO-UHFFFAOYSA-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 group 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 group 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 group 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
- 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 group 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-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 group 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
- 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
- LQZTWTLWALPNSN-UHFFFAOYSA-N 1-ethyl-3-[4-[7-(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)C2 LQZTWTLWALPNSN-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
- 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 group 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
- SOLMPTOWRBTKBX-UHFFFAOYSA-N 1-ethyl-3-[4-[7-(3-methyl-1,2,4-thiadiazol-5-yl)-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1SN=C(C)N=1)C2 SOLMPTOWRBTKBX-UHFFFAOYSA-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 group 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 group 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
- YPAXEWBTIGSMRV-IBGZPJMESA-N 1-ethyl-3-[4-[7-(4-hydroxybutyl)-4-[(3s)-3-methylmorpholin-4-yl]-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(CCCCO)CC2 YPAXEWBTIGSMRV-IBGZPJMESA-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
- 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
- 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 group 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 group 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 group 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 group 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 group 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
- UXMVBMILZYUHQN-KKSFZXQISA-N 1-ethyl-3-[4-[7-[(2s)-2-hydroxybutanoyl]-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)CC)C2 UXMVBMILZYUHQN-KKSFZXQISA-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 group 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
- 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 group 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 group 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
- ZIFVAALZQGJRRR-IBGZPJMESA-N 1-ethyl-3-[4-[7-ethyl-4-[(3s)-3-ethylmorpholin-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(CC)C2 ZIFVAALZQGJRRR-IBGZPJMESA-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
- VTYXHSDRIHEYHT-INIZCTEOSA-N 1-ethyl-3-[4-[7-ethyl-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)C2 VTYXHSDRIHEYHT-INIZCTEOSA-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
- CSYOHFLGGKLCIQ-HNNXBMFYSA-N 1-ethyl-3-[4-[7-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(C)C2 CSYOHFLGGKLCIQ-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 group 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
- JREJQAWGQCMSIY-UHFFFAOYSA-N 1-methyl-pyrazole-5-carboxylic acid Chemical compound CN1N=CC=C1C(O)=O JREJQAWGQCMSIY-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
- HUUPVABNAQUEJW-UHFFFAOYSA-N 1-methylpiperidin-4-one Chemical compound CN1CCC(=O)CC1 HUUPVABNAQUEJW-UHFFFAOYSA-N 0.000 description 1
- VSNHCAURESNICA-NJFSPNSNSA-N 1-oxidanylurea Chemical compound N[14C](=O)NO VSNHCAURESNICA-NJFSPNSNSA-N 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
- 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
- OVRWUZYZECPJOB-UHFFFAOYSA-N 2,2-difluoroethanamine Chemical compound NCC(F)F OVRWUZYZECPJOB-UHFFFAOYSA-N 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 group 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
- CRZWDCLOJWDOTA-KRWDZBQOSA-N 2-[2-[4-(ethylcarbamoylamino)phenyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-n-(2-hydroxyethyl)acetamide Chemical group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC(=O)NCCO)C2 CRZWDCLOJWDOTA-KRWDZBQOSA-N 0.000 description 1
- XGLFTJCVQXNKCZ-INIZCTEOSA-N 2-[2-[4-(ethylcarbamoylamino)phenyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-n-methylacetamide Chemical group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC(=O)NC)C2 XGLFTJCVQXNKCZ-INIZCTEOSA-N 0.000 description 1
- MPGLZGCPKPYXQG-SFHVURJKSA-N 2-[2-[4-(ethylcarbamoylamino)phenyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-n-propylacetamide Chemical group C1N(CC(=O)NCCC)CCC2=C1N=C(C=1C=CC(NC(=O)NCC)=CC=1)N=C2N1CCOC[C@@H]1C MPGLZGCPKPYXQG-SFHVURJKSA-N 0.000 description 1
- FGWIAICUKAVYHF-HNNXBMFYSA-N 2-[2-[4-(ethylcarbamoylamino)phenyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]acetamide Chemical group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC(N)=O)C2 FGWIAICUKAVYHF-HNNXBMFYSA-N 0.000 description 1
- GREXONRVLLEVMN-HNNXBMFYSA-N 2-[2-[4-(ethylcarbamoylamino)phenyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]acetic acid Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC(O)=O)C2 GREXONRVLLEVMN-HNNXBMFYSA-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 group 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
- MNQGLYPRGGHZAY-AWEZNQCLSA-N 2-[4-[4-[(3s)-3-methylmorpholin-4-yl]-5,6,7,8-tetrahydropyrido[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=C1CCNC2 MNQGLYPRGGHZAY-AWEZNQCLSA-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 group 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 group 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
- 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
- AGYUQBNABXVWMS-UHFFFAOYSA-N 2-chloro-5-fluoropyrimidine Chemical compound FC1=CN=C(Cl)N=C1 AGYUQBNABXVWMS-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
- 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
- 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
- GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical group 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 group 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 group 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
- 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 group 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
- 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
- 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
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-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
- 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 group 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
- SDHXVEMYAAINPO-AWEZNQCLSA-N 3-methyl-6-[4-[4-[(3s)-3-methylmorpholin-4-yl]-5,6,7,8-tetrahydropyrido[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=C1CCNC2 SDHXVEMYAAINPO-AWEZNQCLSA-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 group 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
- 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
- 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
- ZANPJXNYBVVNSD-UHFFFAOYSA-N 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(N)C=C1 ZANPJXNYBVVNSD-UHFFFAOYSA-N 0.000 description 1
- FMQKKTFNCDJUEW-UHFFFAOYSA-N 4-(4-morpholin-4-yl-6-pyrimidin-2-yl-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-yl)benzamide Chemical group C1=CC(C(=O)N)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(C=1N=CC=CN=1)C2 FMQKKTFNCDJUEW-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 group C1=CC(N)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=CC=CN=1)C2 ROJGNWWTVWLXOU-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 group 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
- ZDNPBIREKHGWPM-UHFFFAOYSA-N 4-[2-(4-nitrophenyl)-6-pyrimidin-2-yl-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]morpholine Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(C=1N=CC=CN=1)C2 ZDNPBIREKHGWPM-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
- YFCIFWOJYYFDQP-PTWZRHHISA-N 4-[3-amino-6-[(1S,3S,4S)-3-fluoro-4-hydroxycyclohexyl]pyrazin-2-yl]-N-[(1S)-1-(3-bromo-5-fluorophenyl)-2-(methylamino)ethyl]-2-fluorobenzamide Chemical compound CNC[C@@H](NC(=O)c1ccc(cc1F)-c1nc(cnc1N)[C@H]1CC[C@H](O)[C@@H](F)C1)c1cc(F)cc(Br)c1 YFCIFWOJYYFDQP-PTWZRHHISA-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
- 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
- JHNRTJRDRWKAIW-UHFFFAOYSA-N 4-chloro-2,6-dimethoxypyrimidine Chemical compound COC1=CC(Cl)=NC(OC)=N1 JHNRTJRDRWKAIW-UHFFFAOYSA-N 0.000 description 1
- FZINIBTZNSPWQR-UHFFFAOYSA-N 4-chloro-2-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC(Cl)=CC=N1 FZINIBTZNSPWQR-UHFFFAOYSA-N 0.000 description 1
- BEQUUSCRAKEKQM-UHFFFAOYSA-N 4-chloro-3-fluoropyridine Chemical compound FC1=CN=CC=C1Cl BEQUUSCRAKEKQM-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
- 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
- LQVSXEXWXILGBH-UHFFFAOYSA-N 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydrobenzimidazol-2-one Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(NC(=O)N2)C2=C1 LQVSXEXWXILGBH-UHFFFAOYSA-N 0.000 description 1
- BPQVMIDUTRJYSC-UHFFFAOYSA-N 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine Chemical compound O1C(C)(C)C(C)(C)OB1C1=CN=C(N)N=C1 BPQVMIDUTRJYSC-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 group 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
- 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
- QPXQPPXGTQABCW-UHFFFAOYSA-N 5-methyl-1,3,4-oxadiazole-2-carboxylic acid Chemical compound CC1=NN=C(C(O)=O)O1 QPXQPPXGTQABCW-UHFFFAOYSA-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 group 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
- PSVVTXRFDNVMNB-UHFFFAOYSA-N 5-methyloxadiazol-4-amine Chemical compound CC=1ON=NC=1N PSVVTXRFDNVMNB-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
- SJYYLFPZFXPYDO-LAUBAEHRSA-N 6-[4-[(10ar)-4-[(3s)-3-methylmorpholin-4-yl]-5,6,8,9,10,10a-hexahydropyrimido[5,4-g]indolizin-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=C1CCN1CCC[C@@H]12 SJYYLFPZFXPYDO-LAUBAEHRSA-N 0.000 description 1
- SJYYLFPZFXPYDO-UWJYYQICSA-N 6-[4-[(10as)-4-[(3s)-3-methylmorpholin-4-yl]-5,6,8,9,10,10a-hexahydropyrimido[5,4-g]indolizin-2-yl]anilino]-1h-pyridin-2-one Chemical group C[C@H]1COCCN1C1=NC(C=2C=CC(NC=3NC(=O)C=CC=3)=CC=2)=NC2=C1CCN1CCC[C@H]12 SJYYLFPZFXPYDO-UWJYYQICSA-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 group 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
- ONRUNGPKZMIFCE-HNNXBMFYSA-N 6-[4-[4-[(3s)-3-methylmorpholin-4-yl]-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl]anilino]-1h-pyridin-2-one Chemical group C[C@H]1COCCN1C1=NC(C=2C=CC(NC=3NC(=O)C=CC=3)=CC=2)=NC2=C1CCNC2 ONRUNGPKZMIFCE-HNNXBMFYSA-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 group 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 group 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
- DJDJGJVGAMOFFZ-IBGZPJMESA-N 6-[4-[7-(1-ethylimidazol-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 CCN1C=CN=C1N1CC(N=C(N=C2N3[C@H](COCC3)C)C=3C=CC(NC=4NC(=O)C=CC=4)=CC=3)=C2CC1 DJDJGJVGAMOFFZ-IBGZPJMESA-N 0.000 description 1
- ZIYQKVGBYIICBI-SFHVURJKSA-N 6-[4-[7-(1-methylimidazol-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(C=CN=1)C)C2 ZIYQKVGBYIICBI-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 group 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 group 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 group 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 group 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
- 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
- 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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-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
- 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
- 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
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 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
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 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
- 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
- 241000283690 Bos taurus Species 0.000 description 1
- 201000006474 Brain Ischemia Diseases 0.000 description 1
- 101150008921 Brca2 gene Proteins 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 108010037003 Buserelin Proteins 0.000 description 1
- 239000004358 Butane-1, 3-diol Substances 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 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 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
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 206010007559 Cardiac failure congestive Diseases 0.000 description 1
- 208000006029 Cardiomegaly Diseases 0.000 description 1
- 102000014914 Carrier Proteins Human genes 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 206010008120 Cerebral ischaemia Diseases 0.000 description 1
- 206010008342 Cervix carcinoma 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
- 108010066551 Cholestenone 5 alpha-Reductase Proteins 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
- 208000001333 Colorectal Neoplasms Diseases 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
- 229940123780 DNA topoisomerase I inhibitor Drugs 0.000 description 1
- 101000678286 Danio rerio Eukaryotic translation initiation factor 4E-binding protein 3-like Proteins 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
- 101000800913 Dictyostelium discoideum Eukaryotic translation initiation factor 4E-1A-binding protein homolog Proteins 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- ZQZFYGIXNQKOAV-OCEACIFDSA-N Droloxifene Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=C(O)C=CC=1)\C1=CC=C(OCCN(C)C)C=C1 ZQZFYGIXNQKOAV-OCEACIFDSA-N 0.000 description 1
- 101000800906 Drosophila melanogaster Eukaryotic translation initiation factor 4E-binding protein Proteins 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
- 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
- GISRWBROCYNDME-PELMWDNLSA-N F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C Chemical compound F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C GISRWBROCYNDME-PELMWDNLSA-N 0.000 description 1
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-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
- 239000004471 Glycine Substances 0.000 description 1
- 108010069236 Goserelin Proteins 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
- 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
- 108010081348 HRT1 protein Hairy Proteins 0.000 description 1
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 102100024025 Heparanase Human genes 0.000 description 1
- 206010019842 Hepatomegaly 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
- 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
- VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-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
- 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
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-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
- 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
- 108700041567 MDR Genes Proteins 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
- 235000019759 Maize starch Nutrition 0.000 description 1
- 208000025205 Mantle-Cell Lymphoma Diseases 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 101100087591 Mus musculus Rictor gene Proteins 0.000 description 1
- 241000699670 Mus sp. Species 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
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-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
- 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
- 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
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 1
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 1
- 206010033128 Ovarian cancer Diseases 0.000 description 1
- 206010061535 Ovarian neoplasm Diseases 0.000 description 1
- 229910003872 O—Si Inorganic materials 0.000 description 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 241001494479 Pecora Species 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
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- HCBIBCJNVBAKAB-UHFFFAOYSA-N Procaine hydrochloride Chemical compound Cl.CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 HCBIBCJNVBAKAB-UHFFFAOYSA-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
- 101710194805 Putative repressor Proteins 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 208000015634 Rectal Neoplasms Diseases 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
- 208000006265 Renal cell carcinoma Diseases 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
- 102000007562 Serum Albumin Human genes 0.000 description 1
- 108010071390 Serum Albumin Proteins 0.000 description 1
- 229910007161 Si(CH3)3 Inorganic materials 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
- NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 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
- 241000282887 Suidae Species 0.000 description 1
- 101000996723 Sus scrofa Gonadotropin-releasing hormone receptor Proteins 0.000 description 1
- 230000006044 T cell activation Effects 0.000 description 1
- 230000017274 T cell anergy Effects 0.000 description 1
- 102100030904 Target of rapamycin complex 2 subunit MAPKAP1 Human genes 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
- 101710173511 Tensin homolog Proteins 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
- 208000024770 Thyroid neoplasm Diseases 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 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
- 208000026911 Tuberous sclerosis complex Diseases 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- 208000007097 Urinary Bladder 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
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 1
- 206010047741 Vulval cancer 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
- 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
- SPSKFVHUUJWUPB-UHFFFAOYSA-N [4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]boronic acid Chemical compound O1C(C)=NN=C1C1=CC=C(B(O)O)C=C1 SPSKFVHUUJWUPB-UHFFFAOYSA-N 0.000 description 1
- PJUTWGKLVJYVSJ-UHFFFAOYSA-N [4-(7-benzoyl-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl] n-ethylcarbamate Chemical compound C1=CC(OC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)C=1C=CC=CC=1)C2 PJUTWGKLVJYVSJ-UHFFFAOYSA-N 0.000 description 1
- JSVGNHQHLLIRIQ-DEOSSOPVSA-N [4-[(3s)-3-methylmorpholin-4-yl]-2-[4-[(6-phenylmethoxypyrazin-2-yl)amino]phenyl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-pyridin-3-ylmethanone Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC=3N=C(OCC=4C=CC=CC=4)C=NC=3)=CC=2)=NC2=C1CCN(C(=O)C=1C=NC=CC=1)C2 JSVGNHQHLLIRIQ-DEOSSOPVSA-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
- NFMOBSIZJMBINS-UHFFFAOYSA-N [4-ethyl-4-(4-morpholin-4-yl-8-oxo-6,7-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)cyclohexa-1,5-dien-1-yl]urea Chemical compound N=1C(N2CCOCC2)=C2CCNC(=O)C2=NC=1C1(CC)CC=C(NC(N)=O)C=C1 NFMOBSIZJMBINS-UHFFFAOYSA-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
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000005042 acyloxymethyl group Chemical group 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000001780 adrenocortical effect Effects 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
- 125000005907 alkyl ester group Chemical group 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
- 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
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 230000003321 amplification Effects 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
- 229940046836 anti-estrogen Drugs 0.000 description 1
- 230000001833 anti-estrogenic effect Effects 0.000 description 1
- 230000003432 anti-folate effect Effects 0.000 description 1
- 230000001740 anti-invasion Effects 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 229940127074 antifolate Drugs 0.000 description 1
- 229940045687 antimetabolites folic acid analogs Drugs 0.000 description 1
- 229940041181 antineoplastic drug 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
- 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
- 229960001230 asparagine Drugs 0.000 description 1
- 235000009582 asparagine Nutrition 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 239000003719 aurora kinase inhibitor Substances 0.000 description 1
- 230000004900 autophagic degradation Effects 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
- 230000004888 barrier function Effects 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
- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 description 1
- 229960001950 benzethonium chloride Drugs 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
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
- 235000019445 benzyl alcohol Nutrition 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
- 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
- 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
- 229960001561 bleomycin Drugs 0.000 description 1
- 239000003114 blood coagulation factor Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 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
- 239000012267 brine Substances 0.000 description 1
- 239000012512 bulk drug substance Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 229960002719 buserelin Drugs 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
- 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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N butyl alcohol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 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
- 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 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
- 229960005243 carmustine Drugs 0.000 description 1
- 239000003054 catalyst Substances 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
- 201000010881 cervical cancer Diseases 0.000 description 1
- 229940082500 cetostearyl alcohol Drugs 0.000 description 1
- 229960005395 cetuximab Drugs 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 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
- 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
- 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
- 208000029742 colonic neoplasm Diseases 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
- 238000010668 complexation reaction Methods 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
- 229960005168 croscarmellose Drugs 0.000 description 1
- 239000001767 crosslinked sodium carboxy methyl cellulose Substances 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000002875 cyclin dependent kinase inhibitor Substances 0.000 description 1
- 229940043378 cyclin-dependent kinase inhibitor Drugs 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
- 229960000684 cytarabine Drugs 0.000 description 1
- 210000004292 cytoskeleton Anatomy 0.000 description 1
- 230000001086 cytosolic effect Effects 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
- 230000001934 delay Effects 0.000 description 1
- 230000002939 deleterious effect Effects 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
- 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
- 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
- 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
- PSHRANCNVXNITH-UHFFFAOYSA-N dimethylamino acetate Chemical compound CN(C)OC(C)=O PSHRANCNVXNITH-UHFFFAOYSA-N 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 238000004090 dissolution 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
- 229950004203 droloxifene Drugs 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
- 238000001035 drying Methods 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
- 201000003914 endometrial carcinoma Diseases 0.000 description 1
- 230000002357 endometrial effect Effects 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
- 229960001904 epirubicin Drugs 0.000 description 1
- 229940082789 erbitux Drugs 0.000 description 1
- 229960001433 erlotinib 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
- 229960001842 estramustine Drugs 0.000 description 1
- FRPJXPJMRWBBIH-RBRWEJTLSA-N estramustine Chemical compound ClCCN(CCCl)C(=O)OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 FRPJXPJMRWBBIH-RBRWEJTLSA-N 0.000 description 1
- 229960004750 estramustine phosphate Drugs 0.000 description 1
- ADFOJJHRTBFFOF-RBRWEJTLSA-N estramustine phosphate Chemical compound ClCCN(CCCl)C(=O)OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)OP(O)(O)=O)[C@@H]4[C@@H]3CCC2=C1 ADFOJJHRTBFFOF-RBRWEJTLSA-N 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- 239000000328 estrogen antagonist 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
- 229950006566 etanidazole Drugs 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
- 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
- YXDXSBLZVORMOH-UHFFFAOYSA-N ethyl 2-[4-(ethylcarbamoylamino)phenyl]-4-morpholin-4-yl-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylate Chemical group 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
- 108091012329 eukaryotic initiation factor 4E binding proteins Proteins 0.000 description 1
- 102000022577 eukaryotic initiation factor 4E binding proteins Human genes 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
- 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
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 description 1
- 150000005699 fluoropyrimidines Chemical class 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
- 235000019253 formic acid Nutrition 0.000 description 1
- 229960002258 fulvestrant Drugs 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000021474 generally recognized As safe (food) Nutrition 0.000 description 1
- 235000021473 generally recognized as safe (food ingredients) Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 229940049906 glutamate Drugs 0.000 description 1
- 229960002989 glutamic acid Drugs 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
- UHUSDOQQWJGJQS-UHFFFAOYSA-N glycerol 1,2-dioctadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCCCCCCCCCCCC UHUSDOQQWJGJQS-UHFFFAOYSA-N 0.000 description 1
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
- 229940075507 glyceryl monostearate 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
- 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
- 230000002440 hepatic effect Effects 0.000 description 1
- 231100000844 hepatocellular carcinoma Toxicity 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
- XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 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
- 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
- 229960001330 hydroxycarbamide Drugs 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
- 208000013403 hyperactivity Diseases 0.000 description 1
- 229960001101 ifosfamide Drugs 0.000 description 1
- HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 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
- 125000004857 imidazopyridinyl group Chemical class N1C(=NC2=C1C=CC=N2)* 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
- 239000000367 immunologic factor Substances 0.000 description 1
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 238000009169 immunotherapy Methods 0.000 description 1
- DBIGHPPNXATHOF-UHFFFAOYSA-N improsulfan Chemical compound CS(=O)(=O)OCCCNCCCOS(C)(=O)=O DBIGHPPNXATHOF-UHFFFAOYSA-N 0.000 description 1
- 229950008097 improsulfan Drugs 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 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
- 229940102223 injectable solution Drugs 0.000 description 1
- 229940102213 injectable suspension Drugs 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
- 230000002452 interceptive effect Effects 0.000 description 1
- 229940079322 interferon Drugs 0.000 description 1
- 229940028885 interleukin-4 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
- 238000007913 intrathecal administration Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 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
- 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
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 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
- NWYYWIJOWOLJNR-RXMQYKEDSA-N l-valinol Chemical compound CC(C)[C@H](N)CO NWYYWIJOWOLJNR-RXMQYKEDSA-N 0.000 description 1
- 239000008101 lactose Substances 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
- 229960004891 lapatinib 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
- 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
- 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 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- YTJXGDYAEOTOCG-UHFFFAOYSA-N lithium;di(propan-2-yl)azanide;oxolane Chemical compound [Li+].C1CCOC1.CC(C)[N-]C(C)C YTJXGDYAEOTOCG-UHFFFAOYSA-N 0.000 description 1
- 201000007270 liver cancer Diseases 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 229960002247 lomustine Drugs 0.000 description 1
- 230000004777 loss-of-function mutation Effects 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 201000005296 lung carcinoma Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 229940087857 lupron Drugs 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
- 208000015486 malignant pancreatic neoplasm Diseases 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
- 229960002985 medroxyprogesterone acetate Drugs 0.000 description 1
- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 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
- 210000004379 membrane Anatomy 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
- 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
- OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 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
- TWSHCQUMWMPVOF-INIZCTEOSA-N methyl 2-[2-[4-(ethylcarbamoylamino)phenyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]acetate Chemical group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC(=O)OC)C2 TWSHCQUMWMPVOF-INIZCTEOSA-N 0.000 description 1
- TVGMVBFQUJBMAN-UHFFFAOYSA-N methyl 2-[2-[4-(ethylcarbamoylamino)phenyl]-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]-4-(trifluoromethyl)pyrimidine-5-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C=1N=C(C(C(=O)OC)=CN=1)C(F)(F)F)C2 TVGMVBFQUJBMAN-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
- 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
- YSXVDMJBOIWDNA-KRWDZBQOSA-N methyl 3-[2-[4-(ethylcarbamoylamino)phenyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]propanoate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CCC(=O)OC)C2 YSXVDMJBOIWDNA-KRWDZBQOSA-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
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 1
- 229960000282 metronidazole Drugs 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
- OBBCSXFCDPPXOL-UHFFFAOYSA-N misonidazole Chemical compound COCC(O)CN1C=CN=C1[N+]([O-])=O OBBCSXFCDPPXOL-UHFFFAOYSA-N 0.000 description 1
- 229950010514 misonidazole Drugs 0.000 description 1
- 229960000350 mitotane Drugs 0.000 description 1
- 239000007932 molded tablet Substances 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids 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
- 238000000465 moulding Methods 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 229940043348 myristyl alcohol Drugs 0.000 description 1
- FEMQXEDRCUEENP-IBGZPJMESA-N n,n-diethyl-2-[2-[4-(ethylcarbamoylamino)phenyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]acetamide Chemical group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC(=O)N(CC)CC)C2 FEMQXEDRCUEENP-IBGZPJMESA-N 0.000 description 1
- VDABGPAAUABIQN-UHFFFAOYSA-N n-[3-(4-morpholin-4-yl-6-pyrimidin-2-yl-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-yl)phenyl]acetamide Chemical group CC(=O)NC1=CC=CC(C=2N=C(C=3CN(CC=3N=2)C=2N=CC=CN=2)N2CCOCC2)=C1 VDABGPAAUABIQN-UHFFFAOYSA-N 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
- SOPXCFZHRCNMMU-UHFFFAOYSA-N n-[4-(4-morpholin-4-yl-6-pyrimidin-2-yl-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-yl)phenyl]acetamide Chemical group C1=CC(NC(=O)C)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(C=1N=CC=CN=1)C2 SOPXCFZHRCNMMU-UHFFFAOYSA-N 0.000 description 1
- CHYNEKMDBVCFNF-UHFFFAOYSA-N n-[4-(4-morpholin-4-yl-6-pyrimidin-2-yl-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-yl)phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(C=1N=CC=CN=1)C2 CHYNEKMDBVCFNF-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 group 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
- MDNKQBOJMBJGHD-UHFFFAOYSA-N n-[4-(6-benzyl-4-morpholin-4-yl-7-oxo-5h-pyrrolo[3,4-d]pyrimidin-2-yl)phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CN(CC=1C=CC=CC=1)C2=O MDNKQBOJMBJGHD-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 group 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
- UCTIGHNWVJGLGW-SFHVURJKSA-N n-cyclobutyl-2-[2-[4-(ethylcarbamoylamino)phenyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]acetamide Chemical group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC(=O)NC1CCC1)C2 UCTIGHNWVJGLGW-SFHVURJKSA-N 0.000 description 1
- PSJGOOMQMAJGBJ-IBGZPJMESA-N n-cyclopentyl-2-[2-[4-(ethylcarbamoylamino)phenyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]acetamide Chemical group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(CC(=O)NC1CCCC1)C2 PSJGOOMQMAJGBJ-IBGZPJMESA-N 0.000 description 1
- OUTJLIMBFOQTRI-KRWDZBQOSA-N n-ethyl-2-[2-[4-(ethylcarbamoylamino)phenyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]acetamide Chemical compound C1N(CC(=O)NCC)CCC2=C1N=C(C=1C=CC(NC(=O)NCC)=CC=1)N=C2N1CCOC[C@@H]1C OUTJLIMBFOQTRI-KRWDZBQOSA-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
- 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
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 235000015097 nutrients Nutrition 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
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 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
- 239000012053 oil suspension Substances 0.000 description 1
- 239000002674 ointment 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
- 229960003104 ornithine Drugs 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
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 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
- 201000002528 pancreatic cancer Diseases 0.000 description 1
- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
- 229960001972 panitumumab Drugs 0.000 description 1
- 238000007911 parenteral administration Methods 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
- 229960001639 penicillamine Drugs 0.000 description 1
- 208000030940 penile carcinoma Diseases 0.000 description 1
- 201000008174 penis carcinoma Diseases 0.000 description 1
- 229960002340 pentostatin Drugs 0.000 description 1
- 239000002304 perfume Substances 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
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 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
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- USRGIUJOYOXOQJ-GBXIJSLDSA-N phosphothreonine Chemical compound OP(=O)(O)O[C@H](C)[C@H](N)C(O)=O USRGIUJOYOXOQJ-GBXIJSLDSA-N 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
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 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
- NUKCGLDCWQXYOQ-UHFFFAOYSA-N piposulfan Chemical compound CS(=O)(=O)OCCC(=O)N1CCN(C(=O)CCOS(C)(=O)=O)CC1 NUKCGLDCWQXYOQ-UHFFFAOYSA-N 0.000 description 1
- 229950001100 piposulfan Drugs 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920000747 poly(lactic acid) 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
- 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
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229940069328 povidone Drugs 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
- 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
- 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 group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)OC(C)C)C2 UIRUEPAOXJBSAX-UHFFFAOYSA-N 0.000 description 1
- IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-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
- 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
- 229940121649 protein inhibitor Drugs 0.000 description 1
- 239000012268 protein inhibitor Substances 0.000 description 1
- 108060006633 protein kinase Proteins 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 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
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 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
- 206010038038 rectal cancer Diseases 0.000 description 1
- 201000001275 rectum cancer Diseases 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
- 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
- VHXNKPBCCMUMSW-FQEVSTJZSA-N rubitecan Chemical compound C1=CC([N+]([O-])=O)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VHXNKPBCCMUMSW-FQEVSTJZSA-N 0.000 description 1
- 229950009213 rubitecan Drugs 0.000 description 1
- 229910021481 rutherfordium Inorganic materials 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
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 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
- 150000003335 secondary amines Chemical class 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
- 238000011452 sequencing regimen Methods 0.000 description 1
- 238000007493 shaping process Methods 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
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate 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
- 229910000162 sodium phosphate Inorganic materials 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
- 238000001179 sorption measurement Methods 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
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- DFVFTMTWCUHJBL-BQBZGAKWSA-N statine Chemical compound CC(C)C[C@H](N)[C@@H](O)CC(O)=O DFVFTMTWCUHJBL-BQBZGAKWSA-N 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
- 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
- 230000002459 sustained effect Effects 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 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
- 230000008685 targeting Effects 0.000 description 1
- WFWLQNSHRPWKFK-ZCFIWIBFSA-N tegafur Chemical compound O=C1NC(=O)C(F)=CN1[C@@H]1OCCC1 WFWLQNSHRPWKFK-ZCFIWIBFSA-N 0.000 description 1
- 229960001674 tegafur Drugs 0.000 description 1
- 229960004964 temozolomide Drugs 0.000 description 1
- 229960000235 temsirolimus Drugs 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 group 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
- SXVQYBXFKFDBPF-XMMPIXPASA-N tert-butyl (8r)-8-(4-ethoxy-4-oxobutyl)-2-[4-(ethylcarbamoylamino)phenyl]-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)OC(C)(C)C)[C@@H]2CCCC(=O)OCC SXVQYBXFKFDBPF-XMMPIXPASA-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 group 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 group 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
- 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 group 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 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 group 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
- SXVQYBXFKFDBPF-DEOSSOPVSA-N tert-butyl (8s)-8-(4-ethoxy-4-oxobutyl)-2-[4-(ethylcarbamoylamino)phenyl]-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)OC(C)(C)C)[C@H]2CCCC(=O)OCC SXVQYBXFKFDBPF-DEOSSOPVSA-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 group 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
- 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
- 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
- PRYOQBNZPMUQOA-HNNXBMFYSA-N tert-butyl 2-(4-aminophenyl)-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(N)=CC=2)=NC2=C1CCN(C(=O)OC(C)(C)C)C2 PRYOQBNZPMUQOA-HNNXBMFYSA-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
- ZMISTEXYEUGOPQ-INIZCTEOSA-N tert-butyl 2-[4-(2,2-difluoroethylcarbamoylamino)phenyl]-4-[(3s)-3-methylmorpholin-4-yl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidine-6-carboxylate Chemical group C[C@H]1COCCN1C1=NC(C=2C=CC(NC(=O)NCC(F)F)=CC=2)=NC2=C1CN(C(=O)OC(C)(C)C)CC2 ZMISTEXYEUGOPQ-INIZCTEOSA-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 group 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
- BYKHNSNPUVAGDH-UHFFFAOYSA-N tert-butyl 2-[4-(ethylcarbamoylamino)phenyl]-4-(1,4-oxazepan-4-yl)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylate Chemical group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCCC2)=NC2=C1CN(C(=O)OC(C)(C)C)C2 BYKHNSNPUVAGDH-UHFFFAOYSA-N 0.000 description 1
- CZLSNOHCJIGMSY-UHFFFAOYSA-N tert-butyl 2-[4-(ethylcarbamoylamino)phenyl]-4-(2-oxomorpholin-4-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CC(=O)OCC2)=NC2=C1CCN(C(=O)OC(C)(C)C)C2 CZLSNOHCJIGMSY-UHFFFAOYSA-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
- NRWURMZRYUSNOP-UHFFFAOYSA-N tert-butyl 2-[4-(ethylcarbamoylamino)phenyl]-4-(oxan-4-yl)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carboxylate Chemical group C1=CC(NC(=O)NCC)=CC=C1C(N=C1C2CCOCC2)=NC2=C1CN(C(=O)OC(C)(C)C)C2 NRWURMZRYUSNOP-UHFFFAOYSA-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 group 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
- HMKOBOLUIOUHOS-KRWDZBQOSA-N tert-butyl 2-[4-(ethylcarbamoylamino)phenyl]-4-[(3s)-3-methylmorpholin-4-yl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidine-6-carboxylate Chemical group C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CN(C(=O)OC(C)(C)C)CC2 HMKOBOLUIOUHOS-KRWDZBQOSA-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 group 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
- GJILJOZJAIADLD-UHFFFAOYSA-N tert-butyl 2-chloro-4-(3,6-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(Cl)=NC=1C1=CCOCC1 GJILJOZJAIADLD-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
- MGEGTSQIBAMHGU-AJZOCDQUSA-N tert-butyl 3-[2-[4-(ethylcarbamoylamino)phenyl]-4-[(3s)-3-methylmorpholin-4-yl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-7-yl]pyrrolidine-1-carboxylate Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C1CN(CC1)C(=O)OC(C)(C)C)C2 MGEGTSQIBAMHGU-AJZOCDQUSA-N 0.000 description 1
- NBMJLUYBQXROKW-UHFFFAOYSA-N tert-butyl 4-(3,4-dihydro-2h-pyran-4-yl)-2-pyrimidin-5-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=NC=2)=NC=1C1CCOC=C1 NBMJLUYBQXROKW-UHFFFAOYSA-N 0.000 description 1
- UHIQCXZTLGGWLU-UHFFFAOYSA-N tert-butyl 4-(oxan-4-yl)-2-pyrimidin-5-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=NC=2)=NC=1C1CCOCC1 UHIQCXZTLGGWLU-UHFFFAOYSA-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
- WFEWERWRGSORDF-HNNXBMFYSA-N tert-butyl 4-[(3s)-3-methylmorpholin-4-yl]-2-(4-nitrophenyl)-7,8-dihydro-5h-pyrido[4,3-d]pyrimidine-6-carboxylate Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(=CC=2)[N+]([O-])=O)=NC2=C1CN(C(=O)OC(C)(C)C)CC2 WFEWERWRGSORDF-HNNXBMFYSA-N 0.000 description 1
- DGGHIYOOFXUMTP-QHCPKHFHSA-N tert-butyl 4-[(3s)-3-methylmorpholin-4-yl]-2-[4-[(6-phenylmethoxypyrazin-2-yl)amino]phenyl]-6,8-dihydro-5h-pyrido[3,4-d]pyrimidine-7-carboxylate Chemical compound C[C@H]1COCCN1C1=NC(C=2C=CC(NC=3N=C(OCC=4C=CC=CC=4)C=NC=3)=CC=2)=NC2=C1CCN(C(=O)OC(C)(C)C)C2 DGGHIYOOFXUMTP-QHCPKHFHSA-N 0.000 description 1
- ATIYWPANRZWDNK-HXBUSHRASA-N tert-butyl 8-(2-aminoethyl)-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)C2CCN ATIYWPANRZWDNK-HXBUSHRASA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229960001712 testosterone propionate Drugs 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 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
- 201000002510 thyroid cancer Diseases 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
- 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
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity 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
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 238000001890 transfection Methods 0.000 description 1
- 239000003558 transferase inhibitor Substances 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 229960000575 trastuzumab Drugs 0.000 description 1
- 230000008736 traumatic injury Effects 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- DQPBQTZZZCVCLD-UHFFFAOYSA-N tributyl(3,6-dihydro-2h-pyran-4-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CCOCC1 DQPBQTZZZCVCLD-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 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
- 229960001099 trimetrexate Drugs 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
- 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
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 230000007306 turnover 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
- 150000003672 ureas Chemical class 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
- 206010046766 uterine cancer Diseases 0.000 description 1
- 208000012991 uterine carcinoma Diseases 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 229940099039 velcade Drugs 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
- 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
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 |
|---|---|
| CA2729045A1 true CA2729045A1 (en) | 2010-02-04 |
Family
ID=41610758
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2729045A Abandoned CA2729045A1 (en) | 2008-07-31 | 2009-07-31 | Pyrimidine compounds, compositions and methods of use |
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) |
Families Citing this family (57)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0974129B1 (en) * | 1996-09-04 | 2006-08-16 | 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 |
| CA2725014C (en) | 2008-05-30 | 2014-06-17 | Amgen Inc. | Inhibitors of pi3 kinase |
| EP2318377B1 (en) | 2008-07-31 | 2013-08-21 | Genentech, Inc. | Pyrimidine compounds, compositions and methods of use |
| JP5579724B2 (ja) * | 2008-10-17 | 2014-08-27 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | ホスファチジルイノシトール−３−キナーゼ（ｐｉ−３キナーゼ）阻害剤としてのテトラ−アザ−複素環 |
| ES2529205T3 (es) | 2009-03-13 | 2015-02-17 | Cellzome Limited | Derivados de pirimidina como inhibidores de mTOR |
| 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 |
| US20100331305A1 (en) * | 2009-06-24 | 2010-12-30 | Genentech, Inc. | Oxo-heterocycle fused pyrimidine compounds, compositions and methods of use |
| BR112012011188A2 (pt) * | 2009-11-12 | 2021-06-29 | F.Hoffmann - La Roche Ag | ''composto,composição farmacêutica e uso de um composto" |
| US8828990B2 (en) * | 2009-11-12 | 2014-09-09 | Genentech, Inc. | N-7 substituted purine and pyrazolopyrimine compounds, compositions and methods of use |
| ES2535116T3 (es) | 2010-03-04 | 2015-05-05 | Cellzome Limited | Derivados de urea sustituida con morfolino como inhibidores de mtor |
| WO2011113512A1 (de) | 2010-03-16 | 2011-09-22 | Merck Patent Gmbh | Morpholinylchinazoline |
| HUE029196T2 (en) | 2010-06-04 | 2017-02-28 | Hoffmann La Roche | Aminoprimidine derivatives as LRRK2 modulators |
| EP2608668B1 (en) * | 2010-08-23 | 2016-06-01 | Merck Sharp & Dohme Corp. | Fused tricyclic inhibitors of mammalian target of rapamycin |
| BR112013011600B1 (pt) | 2010-11-10 | 2022-01-11 | Genentech, Inc | Derivados de pirazol aminopirimidina, seu uso e composição que os compreende |
| MX2013006858A (es) | 2010-12-16 | 2013-07-29 | Hoffmann La Roche | Compuesto triciclicos inhibidores de la pi3k y metodos de uso. |
| TR201815685T4 (tr) * | 2011-04-01 | 2018-11-21 | Genentech Inc | Kanser tedavisi için akt ve mek inhibe edici bileşiklerin kombinasyonları. |
| SG10201504303SA (en) | 2011-04-01 | 2015-07-30 | Genentech Inc | Combinations Of AKT Inhibitor Compounds And Chemotherapeutic Agents, And Methods Of Use |
| EP2694511A1 (en) * | 2011-04-04 | 2014-02-12 | Cellzome Limited | Dihydropyrrolo pyrimidine derivatives as mtor inhibitors |
| US8846656B2 (en) * | 2011-07-22 | 2014-09-30 | Novartis Ag | Tetrahydropyrido-pyridine and tetrahydropyrido-pyrimidine compounds and use thereof as C5a receptor modulators |
| US20130025281A1 (en) | 2011-07-27 | 2013-01-31 | Rentech, Inc. | Gasification system and method |
| JP5995975B2 (ja) | 2011-09-21 | 2016-09-21 | セルゾーム リミテッド | Ｍｔｏｒ阻害剤としてのモルホリノ置換尿素またはカルバメート誘導体 |
| WO2013050508A1 (en) | 2011-10-07 | 2013-04-11 | 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 |
| US9051311B2 (en) | 2012-03-09 | 2015-06-09 | Amgen Inc. | Sulfamide sodium channel inhibitors |
| RU2014149145A (ru) | 2012-05-23 | 2016-07-20 | Ф. Хоффманн-Ля Рош Аг | Композиции и способы получения и применения эндодермальных клеток и гепатоцитов |
| 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 |
| 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 |
| AU2017266911B2 (en) | 2016-05-18 | 2021-09-02 | Array Biopharma, Inc. | KRas G12C inhibitors |
| JOP20190257A1 (ar) * | 2017-04-28 | 2019-10-28 | Novartis Ag | مركبات أريل غير متجانسة ثنائية الحلقة مندمجة 6-6 واستخدامها كمثبطات lats |
| CN111315750B (zh) | 2017-11-06 | 2022-12-23 | 南京明德新药研发有限公司 | 作为mTORC1/2双激酶抑制剂的吡啶并嘧啶类化合物 |
| SI3710439T1 (sl) * | 2017-11-15 | 2023-06-30 | Mirati Therapeutics, Inc., | Zaviralci mutacije kras g12c |
| US10647715B2 (en) | 2017-11-15 | 2020-05-12 | 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 |
| PT3784666T (pt) | 2018-04-24 | 2022-06-06 | Merck Patent Gmbh | Compostos antiproliferação e utilizações dos mesmos |
| WO2019217307A1 (en) | 2018-05-07 | 2019-11-14 | Mirati Therapeutics, Inc. | Kras g12c inhibitors |
| EP3849536A4 (en) | 2018-09-10 | 2022-06-29 | Mirati Therapeutics, Inc. | Combination therapies |
| EP3849538A4 (en) | 2018-09-10 | 2022-06-29 | Mirati Therapeutics, Inc. | Combination therapies |
| HRP20250059T1 (hr) | 2018-09-10 | 2025-03-28 | Mirati Therapeutics, Inc. | Kombinirane terapije |
| EA202190630A1 (ru) | 2018-12-05 | 2021-10-11 | Мирати Терапьютикс, Инк. | Способы комбинированной терапии |
| WO2020146613A1 (en) | 2019-01-10 | 2020-07-16 | Mirati Therapeutics, Inc. | Kras g12c inhibitors |
| 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 |
| JP7622043B2 (ja) | 2019-08-29 | 2025-01-27 | ミラティ セラピューティクス， インコーポレイテッド | Ｋｒａｓ ｇ１２ｄ阻害剤 |
| CA3152025A1 (en) | 2019-09-24 | 2021-04-01 | David BRIERE | Combination therapies |
| EP4076418A4 (en) | 2019-12-20 | 2024-01-24 | Mirati Therapeutics, Inc. | Sos1 inhibitors |
| JP2023540809A (ja) | 2020-09-11 | 2023-09-26 | 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阻害剤の結晶形態 |
| CN116323623B (zh) | 2020-09-18 | 2025-09-26 | 拜耳公司 | 作为SOS1抑制剂的吡啶并[2,3-d]嘧啶-4-胺 |
| IL303446A (en) | 2020-12-15 | 2023-08-01 | Mirati Therapeutics Inc | Azaquinazoline compounds as PAN-KRas inhibitors |
| WO2022133038A1 (en) | 2020-12-16 | 2022-06-23 | 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 |
| DK0831829T3 (da) * | 1995-06-07 | 2003-12-15 | Pfizer | Heterocykliske, ringkondenserede pyrimidinderivater |
| 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 |
| US6608053B2 (en) * | 2000-04-27 | 2003-08-19 | Yamanouchi Pharmaceutical Co., Ltd. | Fused heteroaryl derivatives |
| WO2001083456A1 (en) * | 2000-04-27 | 2001-11-08 | Yamanouchi Pharmaceutical Co., Ltd. | Condensed heteroaryl derivatives |
| ATE346064T1 (de) | 2000-09-15 | 2006-12-15 | Vertex Pharma | Pyrazolverbindungen als protein-kinasehemmer |
| ATE354573T1 (de) * | 2000-12-21 | 2007-03-15 | Vertex Pharma | ßPYRAZOLVERBINDUNGEN, DIE SICH ALS PROTEINKINASEINHIBITOREN EIGNENß |
| 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 |
| DE60236322D1 (de) * | 2001-12-07 | 2010-06-17 | Vertex Pharma | Verbindungen auf pyrimidin-basis als gsk-3-hemmer |
| US7091343B2 (en) * | 2002-03-15 | 2006-08-15 | Vertex Pharmaceuticals Incorporated | Compositions useful as inhibitors of protein kinases |
| EP1552842A1 (en) * | 2002-06-07 | 2005-07-13 | Kyowa Hakko Kogyo Co., Ltd. | Bicyclic pyrimidine derivatives |
| US7208498B2 (en) * | 2002-07-15 | 2007-04-24 | Merck & Co., Inc. | Piperidino pyrimidine dipeptidyl peptidase inhibitors for the treatment of diabetes |
| 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 |
| US7129351B2 (en) * | 2002-11-04 | 2006-10-31 | Hoffmann-La Roche Inc. | Pyrimido compounds having antiproliferative activity |
| EP1608631A4 (en) * | 2003-03-28 | 2008-08-20 | Scios Inc | BICYCLIC PYRIMIDININHIBITORS OF TGF BETA |
| ATE440825T1 (de) * | 2003-06-06 | 2009-09-15 | Vertex Pharma | Pyrimidin-derivate zur verwendung als modulatoren von atp-bindende kassette transportern |
| 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 |
| US20050187389A1 (en) * | 2004-01-13 | 2005-08-25 | Ambit Biosciences Corporation | Pyrrolopyrimidine derivatives and analogs and their use in the treatment and prevention of diseases |
| EP1799218A1 (en) | 2004-09-30 | 2007-06-27 | Tibotec Pharmaceuticals Ltd. | Hcv inhibiting bi-cyclic pyrimidines |
| WO2006042102A2 (en) * | 2004-10-05 | 2006-04-20 | Neurogen Corporation | Pyrrolo-pyridine, pyrrolo-pyrimidine and related heterocyclic compounds |
| EP1806347A4 (en) * | 2004-10-08 | 2009-07-01 | Astellas Pharma Inc | PYRIMIDINE DERIVATIVES FUSED WITH AN AROMATIC RING |
| 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 |
| CA2588220A1 (en) | 2004-12-23 | 2006-06-29 | Pfizer Products Inc. | Heteroaromatic derivatives useful as anticancer agents |
| KR20070113252A (ko) | 2005-02-25 | 2007-11-28 | 쿠도스 파마슈티칼스 리미티드 | 2,4-디아미노-피리도피리미딘 유도체 및 이의 ｍＴＯＲ억제제로서의 용도 |
| GB0520657D0 (en) * | 2005-10-11 | 2005-11-16 | Ludwig Inst Cancer Res | Pharmaceutical compounds |
| GB2431156A (en) | 2005-10-11 | 2007-04-18 | Piramed Ltd | 1-cyclyl-3-substituted- -benzenes and -azines as inhibitors of phosphatidylinositol 3-kinase |
| HRP20120963T1 (hr) * | 2005-11-22 | 2012-12-31 | Kudos Pharmaceuticals Ltd | PIRIDO-, PIRAZO- I PIRIMIDOPIRIMIDINSKI DERIVATI KAO mTOR INHIBITORI |
| US20110034454A1 (en) | 2006-01-11 | 2011-02-10 | Allan Paul Dishington | Morpholino pyrimidine derivatives and their use in therapy |
| EP1996193A2 (en) * | 2006-03-13 | 2008-12-03 | 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 |
| KR101402474B1 (ko) * | 2006-04-26 | 2014-06-19 | 제넨테크, 인크. | 포스포이노시티드 3-키나제 억제제 화합물 및 이를 포함하는 약학적 조성물 |
| 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 |
| MX2008013582A (es) | 2006-04-26 | 2009-01-19 | Hoffmann La Roche | Derivados de pirimidina como inhibidores de fosfatidilinositol-3-c inasa. |
| EP2041139B1 (en) * | 2006-04-26 | 2011-11-09 | F. Hoffmann-La Roche AG | Pharmaceutical compounds |
| GB0608820D0 (en) | 2006-05-04 | 2006-06-14 | Piramed Ltd | Pharmaceutical compounds |
| US8329701B2 (en) | 2006-07-06 | 2012-12-11 | Array Biopharma Inc. | Dihydrofuro pyrimidines as AKT protein kinase inhibitors |
| 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 |
| BRPI0715888B1 (pt) * | 2006-08-23 | 2021-11-03 | Kudos Pharmaceuticals Limited | Composto ou um sal farmaceuticamente aceitável do mesmo, composição farmacêutica, e, uso de um composto |
| MX2009002046A (es) | 2006-08-24 | 2009-03-06 | Astrazeneca Ab | Derivados de morfolino pirimidina utiles en el tratamiento de trastornos proliferativos. |
| US20090325954A1 (en) | 2006-09-14 | 2009-12-31 | Sam Butterworth | 2-benzimidazolyl-6-morpholino-4-phenylpyrimidine 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 |
| 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 |
| 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 |
| CN101563340A (zh) | 2006-09-14 | 2009-10-21 | 阿斯利康(瑞典)有限公司 | 用作pi3k和mtor抑制剂用于治疗增殖性疾病的2-苯并咪唑基-6-吗啉代-4-哌啶-4-基嘧啶衍生物 |
| EP2069330A1 (en) | 2006-09-14 | 2009-06-17 | AstraZeneca AB | 2 -benzimidazolyl- 6 -morpholino-4- (azetidine, pyrrolidine, piperidine or azepine) pyrimidine derivatives as pi3k and mtor inhibitors for the treatment of proliferative disorders |
| KR101507182B1 (ko) * | 2006-12-07 | 2015-03-30 | 제넨테크, 인크. | 포스포이노시타이드 3-키나제 억제제 화합물 및 그의 사용 방법 |
| TWI499420B (zh) * | 2006-12-07 | 2015-09-11 | Hoffmann La Roche | 肌醇磷脂３-激酶抑制劑化合物及使用方法 |
| EP2094837B1 (en) * | 2006-12-14 | 2012-04-25 | Medical Research Council | Use of pi3k, m-tor and akt inhibitors to induce foxp3 expression and generate regulatory t cells |
| US20080234262A1 (en) * | 2007-03-21 | 2008-09-25 | Wyeth | Pyrazolopyrimidine analogs and their use as mtor kinase and pi3 kinase inhibitors |
| US20080233127A1 (en) * | 2007-03-21 | 2008-09-25 | Wyeth | Imidazolopyrimidine analogs and their use as pi3 kinase and mtor inhibitors |
| EP2146981A1 (en) | 2007-04-12 | 2010-01-27 | F. Hoffmann-Roche AG | Pharmaceutical compounds |
| GB0707087D0 (en) | 2007-04-12 | 2007-05-23 | Piramed Ltd | Pharmaceutical compounds |
| WO2008125839A2 (en) | 2007-04-12 | 2008-10-23 | Piramed Limited | Pyrimidine derivatives as inhibitors of phosphatidylinositol-3-kinase |
| 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 |
| JP5539190B2 (ja) | 2007-06-12 | 2014-07-02 | エフ．ホフマン−ラ ロシュ アーゲー | チアゾロピリミジン類及びホスファチジルイノシトール−３キナーゼのインヒビターとしてのそれらの使用 |
| CA2704711C (en) * | 2007-09-24 | 2016-07-05 | Genentech, Inc. | Thiazolopyrimidine p13k inhibitor compounds and methods of use |
| AU2008312631A1 (en) * | 2007-10-16 | 2009-04-23 | Wyeth Llc | Thienopyrimidine and pyrazolopyrimidine compounds and their use as mTOR kinase and PI3 kinase inhibitors |
| WO2009070524A1 (en) | 2007-11-27 | 2009-06-04 | Wyeth | Pyrrolo[3,2-d]pyrimidine compounds and their use as pi3 kinase and mtor kinase inhibitors |
| EP2318377B1 (en) | 2008-07-31 | 2013-08-21 | Genentech, Inc. | Pyrimidine compounds, compositions and methods of use |
-
2009
- 2009-07-31 EP EP09803674.2A patent/EP2318377B1/en active Active
- 2009-07-31 ES ES09803674T patent/ES2432821T3/es active Active
- 2009-07-31 UA UAA201102282A patent/UA101676C2/uk unknown
- 2009-07-31 RU RU2011107278/04A patent/RU2473549C2/ru not_active IP Right Cessation
- 2009-07-31 WO PCT/US2009/052469 patent/WO2010014939A1/en not_active Ceased
- 2009-07-31 BR BRPI0911688-5A patent/BRPI0911688A2/pt not_active IP Right Cessation
- 2009-07-31 KR KR1020117004629A patent/KR20110046514A/ko not_active Ceased
- 2009-07-31 CN CN200980139005XA patent/CN102171194A/zh active Pending
- 2009-07-31 US US12/533,935 patent/US8163763B2/en not_active Expired - Fee Related
- 2009-07-31 TW TW098125944A patent/TW201018681A/zh unknown
- 2009-07-31 JP JP2011521363A patent/JP2011529920A/ja active Pending
- 2009-07-31 CA CA2729045A patent/CA2729045A1/en not_active Abandoned
- 2009-07-31 NZ NZ590777A patent/NZ590777A/xx 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 AU AU2009276339A patent/AU2009276339B2/en not_active Ceased
- 2009-07-31 PE PE2010001222A patent/PE20110403A1/es not_active Application Discontinuation
-
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
Also Published As
| Publication number | Publication date |
|---|---|
| ES2432821T3 (es) | 2013-12-05 |
| EP2318377B1 (en) | 2013-08-21 |
| EP2318377A4 (en) | 2012-05-09 |
| US20120165313A1 (en) | 2012-06-28 |
| IL210462A0 (en) | 2011-03-31 |
| JP2011529920A (ja) | 2011-12-15 |
| NZ590777A (en) | 2012-11-30 |
| RU2473549C2 (ru) | 2013-01-27 |
| AU2009276339A1 (en) | 2010-02-04 |
| CO6311051A2 (es) | 2011-08-22 |
| CL2011000191A1 (es) | 2011-05-20 |
| MX2011001196A (es) | 2011-05-30 |
| PE20110403A1 (es) | 2011-07-04 |
| ECSP11010796A (es) | 2011-02-28 |
| US20100069357A1 (en) | 2010-03-18 |
| ZA201100110B (en) | 2012-04-25 |
| WO2010014939A1 (en) | 2010-02-04 |
| UA101676C2 (uk) | 2013-04-25 |
| AU2009276339B2 (en) | 2012-06-07 |
| AR073354A1 (es) | 2010-11-03 |
| TW201018681A (en) | 2010-05-16 |
| KR20110046514A (ko) | 2011-05-04 |
| CN102171194A (zh) | 2011-08-31 |
| RU2011107278A (ru) | 2012-09-10 |
| US8163763B2 (en) | 2012-04-24 |
| BRPI0911688A2 (pt) | 2015-07-28 |
| EP2318377A1 (en) | 2011-05-11 |
| MA32580B1 (fr) | 2011-08-01 |
| AU2009276339A8 (en) | 2011-03-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2009276339B2 (en) | Pyrimidine compounds, compositions and methods of use | |
| AU2021309876B2 (en) | Rock inhibitor, and preparation method therefor and use thereof | |
| AU2019211485B2 (en) | GCN2 inhibitors and uses thereof | |
| KR101659193B1 (ko) | Btk 활성의 억제제로서의 헤테로아릴 피리돈 및 아자-피리돈 화합물 | |
| CA2927252C (en) | Ring-fused bicyclic pyridyl derivatives as fgfr4 inhibitors | |
| AU2011253057B2 (en) | Nitrogen heterocyclic compounds useful as PDE10 inhibitors | |
| JP6496376B2 (ja) | 阻害剤化合物 | |
| EP3524603B1 (en) | Fgfr4 inhibitor, preparation method therefor and pharmaceutical use thereof | |
| EP2558468B1 (en) | 5, 7-substituted-imidazo [1,2-c] pyrimidines as inhibitors of jak kinases | |
| JP6378785B2 (ja) | Ｔａｎｋ結合キナーゼインヒビター化合物 | |
| CA2728559A1 (en) | Cdk modulators | |
| WO2010118207A1 (en) | Pyrazolo [1, 5-a] pyrimidine derivatives as mtor inhibitors | |
| JP2014508145A (ja) | Ｐｉ３キナーゼ阻害剤としての複素環化合物 | |
| TW202204362A (zh) | 作為PI3K-γ抑制劑之雜環化合物 | |
| WO2006025567A1 (ja) | 新規置換イミダゾール誘導体 | |
| CA2766151A1 (en) | Oxo-heterocycle fused pyrimidine compounds, compositions and methods of use | |
| CN113683629B (zh) | 取代的杂芳基化合物及其组合物和用途 | |
| HK1160466A (en) | Pyrimidine compounds, compositions and methods of use | |
| HK1236197A1 (en) | Tank-binding kinase inhibitor compounds | |
| HK1236197B (en) | Tank-binding kinase inhibitor compounds |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20140731 |