AU2009276339B2 - Pyrimidine compounds, compositions and methods of use - Google Patents

Info

Publication number

AU2009276339B2

AU2009276339B2 AU2009276339A AU2009276339A AU2009276339B2 AU 2009276339 B2 AU2009276339 B2 AU 2009276339B2 AU 2009276339 A AU2009276339 A AU 2009276339A AU 2009276339 A AU2009276339 A AU 2009276339A AU 2009276339 B2 AU2009276339 B2 AU 2009276339B2

Authority

AU

Australia

Prior art keywords

phenyl

pyrimidin

tetrahydropyrido

urea

ethyl

Prior art date

2008-07-31

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Ceased

Links

• Espacenet
• Global Dossier
• Discuss

• 238000000034 method Methods 0.000 title claims description 109
• 239000000203 mixture Substances 0.000 title description 83
• 150000003230 pyrimidines Chemical class 0.000 title description 8
• 150000001875 compounds Chemical class 0.000 claims abstract description 329
• 102000013530 TOR Serine-Threonine Kinases Human genes 0.000 claims abstract description 47
• 108010065917 TOR Serine-Threonine Kinases Proteins 0.000 claims abstract description 47
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 44
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 43
• 201000011510 cancer Diseases 0.000 claims abstract description 35
• 150000003839 salts Chemical class 0.000 claims abstract description 34
• 238000011282 treatment Methods 0.000 claims abstract description 27
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 813
• 239000004202 carbamide Substances 0.000 claims description 572
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 463
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 255
• -1 3-methyl-morpholin-4-yl Chemical group 0.000 claims description 209
• 125000000217 alkyl group Chemical group 0.000 claims description 90
• 229910052740 iodine Inorganic materials 0.000 claims description 83
• 125000001424 substituent group Chemical group 0.000 claims description 73
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 67
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 66
• 229910052739 hydrogen Inorganic materials 0.000 claims description 66
• 229910052757 nitrogen Inorganic materials 0.000 claims description 62
• 239000001257 hydrogen Substances 0.000 claims description 59
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 58
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 57
• 125000001188 haloalkyl group Chemical group 0.000 claims description 53
• 125000003118 aryl group Chemical group 0.000 claims description 46
• 125000003342 alkenyl group Chemical group 0.000 claims description 43
• 150000002431 hydrogen Chemical class 0.000 claims description 37
• 125000001072 heteroaryl group Chemical group 0.000 claims description 35
• 125000005842 heteroatom Chemical group 0.000 claims description 35
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 35
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 34
• 125000000304 alkynyl group Chemical group 0.000 claims description 32
• 229910052731 fluorine Inorganic materials 0.000 claims description 28
• 125000004429 atom Chemical group 0.000 claims description 27
• 229910052799 carbon Inorganic materials 0.000 claims description 27
• 229910052801 chlorine Inorganic materials 0.000 claims description 27
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
• 229910052794 bromium Inorganic materials 0.000 claims description 26
• UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 25
• 229910052736 halogen Inorganic materials 0.000 claims description 24
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 22
• 208000035475 disorder Diseases 0.000 claims description 22
• 150000002367 halogens Chemical class 0.000 claims description 22
• 125000000623 heterocyclic group Chemical group 0.000 claims description 21
• 239000008194 pharmaceutical composition Substances 0.000 claims description 20
• 241000124008 Mammalia Species 0.000 claims description 19
• 125000002947 alkylene group Chemical group 0.000 claims description 17
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 16
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 15
• 239000003814 drug Substances 0.000 claims description 15
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 14
• 230000000694 effects Effects 0.000 claims description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
• 229910052701 rubidium Inorganic materials 0.000 claims description 12
• DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims description 11
• 239000003085 diluting agent Substances 0.000 claims description 11
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 10
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 10
• 125000004474 heteroalkylene group Chemical group 0.000 claims description 10
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
• 229910003827 NRaRb Inorganic materials 0.000 claims description 9
• 239000002253 acid Substances 0.000 claims description 9
• 125000004450 alkenylene group Chemical group 0.000 claims description 9
• 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 9
• 238000002360 preparation method Methods 0.000 claims description 9
• 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 8
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 7
• 241000282414 Homo sapiens Species 0.000 claims description 7
• 239000002246 antineoplastic agent Substances 0.000 claims description 7
• 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 7
• 229910052760 oxygen Inorganic materials 0.000 claims description 7
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 6
• 201000009030 Carcinoma Diseases 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 230000002401 inhibitory effect Effects 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
• BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 claims description 6
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 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
• 125000005551 pyridylene 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
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 5
• 206010038389 Renal cancer Diseases 0.000 claims description 5
• 206010039491 Sarcoma Diseases 0.000 claims description 5
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 5
• 208000005017 glioblastoma Diseases 0.000 claims description 5
• 125000002883 imidazolyl group Chemical group 0.000 claims description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• 208000032839 leukemia Diseases 0.000 claims description 5
• RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 claims description 5
• 125000002950 monocyclic group Chemical group 0.000 claims description 5
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 5
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
• 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 4
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 4
• 206010005003 Bladder cancer Diseases 0.000 claims description 4
• 208000010667 Carcinoma of liver and intrahepatic biliary tract Diseases 0.000 claims description 4
• 206010073069 Hepatic cancer Diseases 0.000 claims description 4
• 125000004419 alkynylene group Chemical group 0.000 claims description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
• 210000000481 breast Anatomy 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
• 201000002250 liver carcinoma Diseases 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
• 210000001672 ovary Anatomy 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
• 210000000664 rectum Anatomy 0.000 claims description 4
• 208000000649 small cell carcinoma Diseases 0.000 claims description 4
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 4
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
• 125000000335 thiazolyl group Chemical group 0.000 claims description 4
• 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims description 3
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
• DEPDDPLQZYCHOH-UHFFFAOYSA-N 1h-imidazol-2-amine Chemical compound NC1=NC=CN1 DEPDDPLQZYCHOH-UHFFFAOYSA-N 0.000 claims description 3
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 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
• 125000003601 C2-C6 alkynyl group Chemical group 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
• 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
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• 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
• 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 compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)OC(C)(C)C)C2 FYENGIZLDIXPSB-UHFFFAOYSA-N 0.000 claims description 3
• 210000001550 testis Anatomy 0.000 claims description 3
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 3
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
• 210000001685 thyroid gland Anatomy 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
• 125000005913 (C3-C6) cycloalkyl 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
• 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 claims description 2
• 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 claims 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 claims description 2
• 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 claims description 2
• ZJTUKGNZFLSUBN-UHFFFAOYSA-N 1-[4-(7-benzoyl-4-morpholin-4-yl-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl)phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C(=O)C=1C=CC=CC=1)C2 ZJTUKGNZFLSUBN-UHFFFAOYSA-N 0.000 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
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• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
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• 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
• 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 compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(CC=1C=CC=CC=1)CC2 DPFTWJSXPSZNKS-UHFFFAOYSA-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
• 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
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• 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
• 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
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• 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
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• 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
• 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
• LNRDQUYXEAONDR-IBGZPJMESA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(1-methylpiperidin-4-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C1CCN(C)CC1)C2 LNRDQUYXEAONDR-IBGZPJMESA-N 0.000 description 1
• GJGZNKWGPXBKQR-XJDOXCRVSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-7-(1-pyridin-3-ylethyl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@H](COCC2)C)=NC2=C1CCN(C(C)C=1C=NC=CC=1)C2 GJGZNKWGPXBKQR-XJDOXCRVSA-N 0.000 description 1
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• 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
• 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
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• 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
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• YNYXLWSTEPYZQL-UHFFFAOYSA-N 1-ethyl-3-[4-[4-morpholin-4-yl-7-(oxetan-3-yl)-6,8-dihydro-5h-pyrido[3,4-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2CCOCC2)=NC2=C1CCN(C1COC1)C2 YNYXLWSTEPYZQL-UHFFFAOYSA-N 0.000 description 1
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• 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
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• RUNAMALIVBITMK-MRXNPFEDSA-N 1-ethyl-3-[4-[6-(2-hydroxy-2-methylpropanoyl)-4-[(3r)-3-methylmorpholin-4-yl]-7,8-dihydro-5h-pyrido[4,3-d]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C(N=C1N2[C@@H](COCC2)C)=NC2=C1CN(C(=O)C(C)(C)O)CC2 RUNAMALIVBITMK-MRXNPFEDSA-N 0.000 description 1
• 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
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