ES2393215T3 - Derivados de morfolino pirimidina útiles en el tratamiento de trastornos proliferativos - Google Patents

Derivados de morfolino pirimidina útiles en el tratamiento de trastornos proliferativos Download PDF

Info

Publication number: ES2393215T3
Authority: ES; Spain
Prior art keywords: phenyl; pyrimidine; urea; methylmorpholin; alkyl
Prior art date: 2006-08-24
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.): Active

Application number

ES07789273T

Other languages

English (en)

Spanish (es)

Inventor

Maurice Raymond Verschoyle Finlay

Jeffrey Morris

Kurt Gordon Pike

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

AstraZeneca AB

Original Assignee

AstraZeneca AB

Priority date (The priority date 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 date listed.)

2006-08-24

Filing date

2007-08-21

Publication date

2012-12-19

2007-08-21 Application filed by AstraZeneca AB filed Critical AstraZeneca AB

2007-08-21 Priority claimed from PCT/GB2007/003173 external-priority patent/WO2008023159A1/en

2012-12-19 Application granted granted Critical

2012-12-19 Publication of ES2393215T3 publication Critical patent/ES2393215T3/es

Status Active legal-status Critical Current

2027-08-21 Anticipated expiration legal-status Critical

Links

238000011282 treatment Methods 0.000 title claims description 25
230000002062 proliferating effect Effects 0.000 title claims description 16
DUIMWXDLDBNUFD-UHFFFAOYSA-N 4-pyrimidin-2-ylmorpholine Chemical class C1COCCN1C1=NC=CC=N1 DUIMWXDLDBNUFD-UHFFFAOYSA-N 0.000 title description 6
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 1071
125000000217 alkyl group Chemical group 0.000 claims abstract description 501
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 230
125000001424 substituent group Chemical group 0.000 claims abstract description 210
150000001875 compounds Chemical class 0.000 claims abstract description 200
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 193
239000001257 hydrogen Substances 0.000 claims abstract description 193
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 125
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 107
125000004452 carbocyclyl group Chemical group 0.000 claims abstract description 96
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 89
150000003839 salts Chemical class 0.000 claims abstract description 67
125000005647 linker group Chemical group 0.000 claims abstract description 51
125000004415 heterocyclylalkyl group Chemical group 0.000 claims abstract description 46
125000005884 carbocyclylalkyl group Chemical group 0.000 claims abstract description 43
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 14
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 14
125000001475 halogen functional group Chemical group 0.000 claims abstract 12
-1 nitro, hydroxy Chemical group 0.000 claims description 512
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 178
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 152
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 141
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 120
125000003545 alkoxy group Chemical group 0.000 claims description 118
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 107
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 93
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 92
229910052757 nitrogen Inorganic materials 0.000 claims description 85
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 84
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 83
125000004103 aminoalkyl group Chemical group 0.000 claims description 65
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 64
125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 58
125000004043 oxo group Chemical group O=* 0.000 claims description 57
125000004429 atom Chemical group 0.000 claims description 54
125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 53
125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 51
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 51
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 48
125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 45
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 45
125000005236 alkanoylamino group Chemical group 0.000 claims description 42
229910052717 sulfur Inorganic materials 0.000 claims description 40
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 38
125000001589 carboacyl group Chemical group 0.000 claims description 37
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 37
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 36
229910052760 oxygen Inorganic materials 0.000 claims description 36
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 35
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 32
125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 29
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 29
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 29
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 28
125000004432 carbon atom Chemical group C* 0.000 claims description 28
201000010099 disease Diseases 0.000 claims description 27
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 27
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 24
125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
125000004966 cyanoalkyl group Chemical group 0.000 claims description 19
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 19
239000003814 drug Substances 0.000 claims description 16
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 14
125000002837 carbocyclic group Chemical group 0.000 claims description 13
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 13
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 12
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 10
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 9
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 9
UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 8
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 7
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 7
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 7
125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 7
125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 7
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 5
125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 3
239000004202 carbamide Substances 0.000 claims 50
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 10
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 6
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 4
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 3
150000002431 hydrogen Chemical class 0.000 claims 3
HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims 2
125000006317 cyclopropyl amino group Chemical group 0.000 claims 2
JSPCTNUQYWIIOT-UHFFFAOYSA-N piperidine-1-carboxamide Chemical compound NC(=O)N1CCCCC1 JSPCTNUQYWIIOT-UHFFFAOYSA-N 0.000 claims 2
125000002653 sulfanylmethyl group Chemical group [H]SC([H])([H])[*] 0.000 claims 2
KRZJRNZICWNMOA-GXSJLCMTSA-N (3s,4r)-4,8-dihydroxy-3-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=CC=C2[C@@H](O)[C@@H](OC)CC(=O)C2=C1O KRZJRNZICWNMOA-GXSJLCMTSA-N 0.000 claims 1
DASJEQDXHOIOTI-HNNXBMFYSA-N 1,1-dimethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(C)(=O)=O)=NC(C=2C=CC(NC(=O)N(C)C)=CC=2)=N1 DASJEQDXHOIOTI-HNNXBMFYSA-N 0.000 claims 1
GLBYMLVUJJSZIL-INIZCTEOSA-N 1,1-dimethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(propan-2-ylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound N=1C(CS(=O)(=O)C(C)C)=CC(N2[C@H](COCC2)C)=NC=1C1=CC=C(NC(=O)N(C)C)C=C1 GLBYMLVUJJSZIL-INIZCTEOSA-N 0.000 claims 1
IVEBOWKPIPBKKT-INIZCTEOSA-N 1-(1-hydroxy-2-methylpropan-2-yl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(C)(=O)=O)=NC(C=2C=CC(NC(=O)NC(C)(C)CO)=CC=2)=N1 IVEBOWKPIPBKKT-INIZCTEOSA-N 0.000 claims 1
APCXCZKDYRJHIH-KRWDZBQOSA-N 1-(1-hydroxy-2-methylpropan-2-yl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(propan-2-ylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound N=1C(CS(=O)(=O)C(C)C)=CC(N2[C@H](COCC2)C)=NC=1C1=CC=C(NC(=O)NC(C)(C)CO)C=C1 APCXCZKDYRJHIH-KRWDZBQOSA-N 0.000 claims 1
FQRXABJLQMGIFE-LOACHALJSA-N 1-(1-hydroxypropan-2-yl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC(CO)C)=CC=C1C1=NC(CS(C)(=O)=O)=CC(N2[C@H](COCC2)C)=N1 FQRXABJLQMGIFE-LOACHALJSA-N 0.000 claims 1
BQTGQNWOMPGPOC-UHFFFAOYSA-N 1-(1-methoxypropan-2-yl)-3-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC(C)COC)=CC=C1C1=NC(CS(C)(=O)=O)=CC(N2CCOCC2)=N1 BQTGQNWOMPGPOC-UHFFFAOYSA-N 0.000 claims 1
LDAIPXIBPRZFSY-UHFFFAOYSA-N 1-(1-methylpiperidin-4-yl)-3-[4-[4-(2-methylsulfonylpropan-2-yl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound C1CN(C)CCC1NC(=O)NC1=CC=C(C=2N=C(C=C(N=2)N2CCOCC2)C(C)(C)S(C)(=O)=O)C=C1 LDAIPXIBPRZFSY-UHFFFAOYSA-N 0.000 claims 1
PCKVIKAZKQVHDG-UHFFFAOYSA-N 1-(1-methylpiperidin-4-yl)-3-[4-[4-morpholin-4-yl-6-(propan-2-ylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound N=1C(CS(=O)(=O)C(C)C)=CC(N2CCOCC2)=NC=1C(C=C1)=CC=C1NC(=O)NC1CCN(C)CC1 PCKVIKAZKQVHDG-UHFFFAOYSA-N 0.000 claims 1
JHVJOENRLBIRCW-UHFFFAOYSA-N 1-(1-methylpyrazol-3-yl)-3-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound CN1C=CC(NC(=O)NC=2C=CC(=CC=2)C=2N=C(C=C(CS(C)(=O)=O)N=2)N2CCOCC2)=N1 JHVJOENRLBIRCW-UHFFFAOYSA-N 0.000 claims 1
RAXRNZQSSCJIHC-UHFFFAOYSA-N 1-(1h-imidazol-2-ylmethyl)-3-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound N=1C(CS(=O)(=O)C)=CC(N2CCOCC2)=NC=1C(C=C1)=CC=C1NC(=O)NCC1=NC=CN1 RAXRNZQSSCJIHC-UHFFFAOYSA-N 0.000 claims 1
UHMNQHRQPHFQSM-INIZCTEOSA-N 1-(1h-imidazol-2-ylmethyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(C)(=O)=O)=NC(C=2C=CC(NC(=O)NCC=3NC=CN=3)=CC=2)=N1 UHMNQHRQPHFQSM-INIZCTEOSA-N 0.000 claims 1
NEZDWPZOVZIRNS-HNNXBMFYSA-N 1-(1h-imidazol-2-ylmethyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=CC(NC(=O)NCC=3NC=CN=3)=CC=2)=N1 NEZDWPZOVZIRNS-HNNXBMFYSA-N 0.000 claims 1
RKAMWNUBFJDTGS-UHFFFAOYSA-N 1-(2,2-dimethylpropyl)-3-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC(C)(C)C)=CC=C1C1=NC(CS(C)(=O)=O)=CC(N2CCOCC2)=N1 RKAMWNUBFJDTGS-UHFFFAOYSA-N 0.000 claims 1
ASGDFTITXQPUTP-IBGZPJMESA-N 1-(2,6-dimethylphenyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=CC(NC(=O)NC=3C(=CC=CC=3C)C)=CC=2)=N1 ASGDFTITXQPUTP-IBGZPJMESA-N 0.000 claims 1
WWRUNUZEBZBQTQ-UHFFFAOYSA-N 1-(2-ethoxyethyl)-3-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCCOCC)=CC=C1C1=NC(CS(C)(=O)=O)=CC(N2CCOCC2)=N1 WWRUNUZEBZBQTQ-UHFFFAOYSA-N 0.000 claims 1
UDLUMDPUEYVHTN-UHFFFAOYSA-N 1-(2-hydroxyethyl)-1-methyl-3-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)N(CCO)C)=CC=C1C1=NC(CS(C)(=O)=O)=CC(N2CCOCC2)=N1 UDLUMDPUEYVHTN-UHFFFAOYSA-N 0.000 claims 1
HNWQWATVPPSZFQ-UHFFFAOYSA-N 1-(2-hydroxyethyl)-3-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound N=1C(CS(=O)(=O)C)=CC(N2CCOCC2)=NC=1C1=CC=C(NC(=O)NCCO)C=C1 HNWQWATVPPSZFQ-UHFFFAOYSA-N 0.000 claims 1
QBESDNFFKLRQHS-HNNXBMFYSA-N 1-(2-hydroxyethyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(C)(=O)=O)=NC(C=2C=CC(NC(=O)NCCO)=CC=2)=N1 QBESDNFFKLRQHS-HNNXBMFYSA-N 0.000 claims 1
XPCDEHZANGVCHI-KRWDZBQOSA-N 1-(2-hydroxyethyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-propan-2-ylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]urea Chemical compound N=1C(C(C)(C)S(=O)(=O)C(C)C)=CC(N2[C@H](COCC2)C)=NC=1C1=CC=C(NC(=O)NCCO)C=C1 XPCDEHZANGVCHI-KRWDZBQOSA-N 0.000 claims 1
BOCRJQCHTWYDMJ-SFHVURJKSA-N 1-(2-hydroxyethyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-pyridin-4-ylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(=O)(=O)C=2C=CN=CC=2)=NC(C=2C=CC(NC(=O)NCCO)=CC=2)=N1 BOCRJQCHTWYDMJ-SFHVURJKSA-N 0.000 claims 1
YAXRRKMRIXNADF-AWEZNQCLSA-N 1-(2-hydroxyethyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=CC(NC(=O)NCCO)=CC=2)=N1 YAXRRKMRIXNADF-AWEZNQCLSA-N 0.000 claims 1
CHHRHACGSFGTBF-KRWDZBQOSA-N 1-(2-hydroxyethyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-[2-[(4-methyl-1,3-thiazol-2-yl)sulfonyl]propan-2-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(=O)(=O)C=2SC=C(C)N=2)=NC(C=2C=CC(NC(=O)NCCO)=CC=2)=N1 CHHRHACGSFGTBF-KRWDZBQOSA-N 0.000 claims 1
ZVEWIVQHTLZEJM-SFHVURJKSA-N 1-(2-hydroxyethyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-[2-[2-(trifluoromethyl)phenyl]sulfonylpropan-2-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=NC(C=2C=CC(NC(=O)NCCO)=CC=2)=N1 ZVEWIVQHTLZEJM-SFHVURJKSA-N 0.000 claims 1
AEPUKCQIUVKETP-INIZCTEOSA-N 1-(2-methoxyethyl)-1-methyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)N(C)CCOC)=CC=C1C1=NC(CS(C)(=O)=O)=CC(N2[C@H](COCC2)C)=N1 AEPUKCQIUVKETP-INIZCTEOSA-N 0.000 claims 1
YZVASHBMZHJWAW-HNNXBMFYSA-N 1-(2-methoxyethyl)-3-[2-methoxy-4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C1=C(OC)C(NC(=O)NCCOC)=CC=C1C1=NC(CS(C)(=O)=O)=CC(N2[C@H](COCC2)C)=N1 YZVASHBMZHJWAW-HNNXBMFYSA-N 0.000 claims 1
MPADPOORHXXQKB-UHFFFAOYSA-N 1-(2-methoxyethyl)-3-[4-[4-(2-methylsulfonylpropan-2-yl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCCOC)=CC=C1C1=NC(N2CCOCC2)=CC(C(C)(C)S(C)(=O)=O)=N1 MPADPOORHXXQKB-UHFFFAOYSA-N 0.000 claims 1
IFLVJWDDRXJCJX-UHFFFAOYSA-N 1-(2-methoxyethyl)-3-[4-[4-morpholin-4-yl-6-(propan-2-ylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCCOC)=CC=C1C1=NC(CS(=O)(=O)C(C)C)=CC(N2CCOCC2)=N1 IFLVJWDDRXJCJX-UHFFFAOYSA-N 0.000 claims 1
CWDURVOIJAUTGC-UHFFFAOYSA-N 1-(2-methylpropyl)-3-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC(C)C)=CC=C1C1=NC(CS(C)(=O)=O)=CC(N2CCOCC2)=N1 CWDURVOIJAUTGC-UHFFFAOYSA-N 0.000 claims 1
ZPRDDAHXUARHLW-UHFFFAOYSA-N 1-(3,4-difluorophenyl)-3-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound N=1C(CS(=O)(=O)C)=CC(N2CCOCC2)=NC=1C(C=C1)=CC=C1NC(=O)NC1=CC=C(F)C(F)=C1 ZPRDDAHXUARHLW-UHFFFAOYSA-N 0.000 claims 1
CLPJGPQDSSVVGM-AWEZNQCLSA-N 1-(3,5-dimethyl-1h-pyrazol-4-yl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=CC(NC(=O)NC3=C(NN=C3C)C)=CC=2)=N1 CLPJGPQDSSVVGM-AWEZNQCLSA-N 0.000 claims 1
ICLBANKACUPIEV-UHFFFAOYSA-N 1-(3,5-dimethylphenyl)-3-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound CC1=CC(C)=CC(NC(=O)NC=2C=CC(=CC=2)C=2N=C(C=C(CS(C)(=O)=O)N=2)N2CCOCC2)=C1 ICLBANKACUPIEV-UHFFFAOYSA-N 0.000 claims 1
WERHSJFBIWMCMY-UHFFFAOYSA-N 1-(3-chloro-4-fluorophenyl)-3-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound N=1C(CS(=O)(=O)C)=CC(N2CCOCC2)=NC=1C(C=C1)=CC=C1NC(=O)NC1=CC=C(F)C(Cl)=C1 WERHSJFBIWMCMY-UHFFFAOYSA-N 0.000 claims 1
ITCQDWFGHDGJLK-UHFFFAOYSA-N 1-(3-ethylphenyl)-3-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound CCC1=CC=CC(NC(=O)NC=2C=CC(=CC=2)C=2N=C(C=C(CS(C)(=O)=O)N=2)N2CCOCC2)=C1 ITCQDWFGHDGJLK-UHFFFAOYSA-N 0.000 claims 1
OCKQYUWLHXUQEP-UHFFFAOYSA-N 1-(3-hydroxypropyl)-3-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound N=1C(CS(=O)(=O)C)=CC(N2CCOCC2)=NC=1C1=CC=C(NC(=O)NCCCO)C=C1 OCKQYUWLHXUQEP-UHFFFAOYSA-N 0.000 claims 1
FUOLCYUIIRPWEC-SFHVURJKSA-N 1-(3-hydroxypropyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-propan-2-ylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]urea Chemical compound N=1C(C(C)(C)S(=O)(=O)C(C)C)=CC(N2[C@H](COCC2)C)=NC=1C1=CC=C(NC(=O)NCCCO)C=C1 FUOLCYUIIRPWEC-SFHVURJKSA-N 0.000 claims 1
KBQFSURRAHZVHO-KRWDZBQOSA-N 1-(3-hydroxypropyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(propan-2-ylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound N=1C(CS(=O)(=O)C(C)C)=CC(N2[C@H](COCC2)C)=NC=1C1=CC=C(NC(=O)NCCCO)C=C1 KBQFSURRAHZVHO-KRWDZBQOSA-N 0.000 claims 1
PMIMFXVKLALUJT-UHFFFAOYSA-N 1-(3-methoxypropyl)-3-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCCCOC)=CC=C1C1=NC(CS(C)(=O)=O)=CC(N2CCOCC2)=N1 PMIMFXVKLALUJT-UHFFFAOYSA-N 0.000 claims 1
IWXXYMRCRVVPKR-INIZCTEOSA-N 1-(3-methoxypropyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCCCOC)=CC=C1C1=NC(CS(C)(=O)=O)=CC(N2[C@H](COCC2)C)=N1 IWXXYMRCRVVPKR-INIZCTEOSA-N 0.000 claims 1
SISBSDLWUJJKTP-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound N=1C(CS(=O)(=O)C)=CC(N2CCOCC2)=NC=1C(C=C1)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1 SISBSDLWUJJKTP-UHFFFAOYSA-N 0.000 claims 1
BWVQICCEDUXOGN-INIZCTEOSA-N 1-(4-fluorophenyl)-3-[2-methoxy-4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound COC1=CC(C=2N=C(C=C(CS(C)(=O)=O)N=2)N2[C@H](COCC2)C)=CC=C1NC(=O)NC1=CC=C(F)C=C1 BWVQICCEDUXOGN-INIZCTEOSA-N 0.000 claims 1
CTTXJIASTBIXRL-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound N=1C(CS(=O)(=O)C)=CC(N2CCOCC2)=NC=1C(C=C1)=CC=C1NC(=O)NC1=CC=C(F)C=C1 CTTXJIASTBIXRL-UHFFFAOYSA-N 0.000 claims 1
ZGTVIPBFKINCKK-INIZCTEOSA-N 1-(4-fluorophenyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=CC(NC(=O)NC=3C=CC(F)=CC=3)=CC=2)=N1 ZGTVIPBFKINCKK-INIZCTEOSA-N 0.000 claims 1
JKCBYRAGTMHSAS-ZDUSSCGKSA-N 1-(4-fluorophenyl)-3-[5-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]-1,3-thiazol-2-yl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2SC(NC(=O)NC=3C=CC(F)=CC=3)=NC=2)=N1 JKCBYRAGTMHSAS-ZDUSSCGKSA-N 0.000 claims 1
HUZCAUWLKCUNDP-HNNXBMFYSA-N 1-(4-fluorophenyl)-3-[5-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]pyridin-2-yl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=NC(NC(=O)NC=3C=CC(F)=CC=3)=CC=2)=N1 HUZCAUWLKCUNDP-HNNXBMFYSA-N 0.000 claims 1
ZUPWQLQYFZEGLA-HNNXBMFYSA-N 1-(4-methoxyphenyl)-3-[1-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]pyrazol-3-yl]urea Chemical compound C1=CC(OC)=CC=C1NC(=O)NC1=NN(C=2N=C(C=C(CS(C)(=O)=O)N=2)N2[C@H](COCC2)C)C=C1 ZUPWQLQYFZEGLA-HNNXBMFYSA-N 0.000 claims 1
SZHVQTZJGBLEBW-UHFFFAOYSA-N 1-(4-methoxyphenyl)-3-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(OC)=CC=C1NC(=O)NC1=CC=C(C=2N=C(C=C(CS(C)(=O)=O)N=2)N2CCOCC2)C=C1 SZHVQTZJGBLEBW-UHFFFAOYSA-N 0.000 claims 1
NQBNUOGVLSHAST-KRWDZBQOSA-N 1-(4-methoxyphenyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(OC)=CC=C1NC(=O)NC1=CC=C(C=2N=C(C=C(CS(C)(=O)=O)N=2)N2[C@H](COCC2)C)C=C1 NQBNUOGVLSHAST-KRWDZBQOSA-N 0.000 claims 1
IMPFVNXEFVWXIP-AWEZNQCLSA-N 1-(4-methoxyphenyl)-3-[5-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]-1,3-thiazol-2-yl]urea Chemical compound C1=CC(OC)=CC=C1NC(=O)NC1=NC=C(C=2N=C(C=C(CS(C)(=O)=O)N=2)N2[C@H](COCC2)C)S1 IMPFVNXEFVWXIP-AWEZNQCLSA-N 0.000 claims 1
DNJSRTDVOBOERF-UHFFFAOYSA-N 1-(4-methylphenyl)-3-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(C)=CC=C1NC(=O)NC1=CC=C(C=2N=C(C=C(CS(C)(=O)=O)N=2)N2CCOCC2)C=C1 DNJSRTDVOBOERF-UHFFFAOYSA-N 0.000 claims 1
HXGKUEHGVHQWFE-UHFFFAOYSA-N 1-(5-methyl-1,2-oxazol-3-yl)-3-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound O1C(C)=CC(NC(=O)NC=2C=CC(=CC=2)C=2N=C(C=C(CS(C)(=O)=O)N=2)N2CCOCC2)=N1 HXGKUEHGVHQWFE-UHFFFAOYSA-N 0.000 claims 1
FPMXPEUTGOAKPV-INIZCTEOSA-N 1-(cyclopropylmethyl)-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(C)(=O)=O)=NC(C=2C=CC(NC(=O)NCC3CC3)=CC=2)=N1 FPMXPEUTGOAKPV-INIZCTEOSA-N 0.000 claims 1
NETXUNPEZUEUTI-UHFFFAOYSA-N 1-(furan-2-ylmethyl)-3-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound N=1C(CS(=O)(=O)C)=CC(N2CCOCC2)=NC=1C(C=C1)=CC=C1NC(=O)NCC1=CC=CO1 NETXUNPEZUEUTI-UHFFFAOYSA-N 0.000 claims 1
INZYDVYKHSHCMB-CVEARBPZSA-N 1-[(2r)-1-hydroxypropan-2-yl]-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)N[C@@H](CO)C)=CC=C1C1=NC(N2[C@H](COCC2)C)=CC(C(C)(C)S(C)(=O)=O)=N1 INZYDVYKHSHCMB-CVEARBPZSA-N 0.000 claims 1
KZAQHIMXNDHDBP-SFHVURJKSA-N 1-[(4-methoxyphenyl)methyl]-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(OC)=CC=C1CNC(=O)NC1=CC=C(C=2N=C(C=C(CS(C)(=O)=O)N=2)N2[C@H](COCC2)C)C=C1 KZAQHIMXNDHDBP-SFHVURJKSA-N 0.000 claims 1
IFAIENRRZVKBCK-HNNXBMFYSA-N 1-[1-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]pyrazol-3-yl]-3-phenylurea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(N2N=C(NC(=O)NC=3C=CC=CC=3)C=C2)=N1 IFAIENRRZVKBCK-HNNXBMFYSA-N 0.000 claims 1
HMNOVIARXFNHAT-INIZCTEOSA-N 1-[2-(1h-imidazol-5-yl)ethyl]-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=CC(NC(=O)NCCC=3N=CNC=3)=CC=2)=N1 HMNOVIARXFNHAT-INIZCTEOSA-N 0.000 claims 1
NJNFFKBEVFGQPX-UHFFFAOYSA-N 1-[2-(4-methylpiperazin-1-yl)ethyl]-3-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound C1CN(C)CCN1CCNC(=O)NC1=CC=C(C=2N=C(C=C(CS(C)(=O)=O)N=2)N2CCOCC2)C=C1 NJNFFKBEVFGQPX-UHFFFAOYSA-N 0.000 claims 1
DZTCWEQPTZTIMX-UHFFFAOYSA-N 1-[2-(difluoromethoxy)phenyl]-3-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound N=1C(CS(=O)(=O)C)=CC(N2CCOCC2)=NC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1OC(F)F DZTCWEQPTZTIMX-UHFFFAOYSA-N 0.000 claims 1
QKBXBTSQNHQGIJ-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-1-methyl-3-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)N(C)CCN(C)C)=CC=C1C1=NC(CS(C)(=O)=O)=CC(N2CCOCC2)=N1 QKBXBTSQNHQGIJ-UHFFFAOYSA-N 0.000 claims 1
ZCEMYFUSZCRPIS-KRWDZBQOSA-N 1-[2-(dimethylamino)ethyl]-1-methyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=CC(NC(=O)N(C)CCN(C)C)=CC=2)=N1 ZCEMYFUSZCRPIS-KRWDZBQOSA-N 0.000 claims 1
GACKEMWVVSQBLA-KRWDZBQOSA-N 1-[2-(dimethylamino)ethyl]-3-[4-[4-(2-hydroxyethylsulfonylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)CCO)=NC(C=2C=CC(NC(=O)NCCN(C)C)=CC=2)=N1 GACKEMWVVSQBLA-KRWDZBQOSA-N 0.000 claims 1
AWKGAWNBTDLOTJ-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-3-[4-[4-(2-methylsulfonylpropan-2-yl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCCN(C)C)=CC=C1C1=NC(N2CCOCC2)=CC(C(C)(C)S(C)(=O)=O)=N1 AWKGAWNBTDLOTJ-UHFFFAOYSA-N 0.000 claims 1
PWRKKDLBDKHVLH-KRWDZBQOSA-N 1-[2-(dimethylamino)ethyl]-3-[4-[4-(ethylsulfonylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound N=1C(CS(=O)(=O)CC)=CC(N2[C@H](COCC2)C)=NC=1C1=CC=C(NC(=O)NCCN(C)C)C=C1 PWRKKDLBDKHVLH-KRWDZBQOSA-N 0.000 claims 1
XJFOKPHLLJQYQM-KRWDZBQOSA-N 1-[2-(dimethylamino)ethyl]-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(C)(=O)=O)=NC(C=2C=CC(NC(=O)NCCN(C)C)=CC=2)=N1 XJFOKPHLLJQYQM-KRWDZBQOSA-N 0.000 claims 1
WHTKEOGWTDPAMG-FQEVSTJZSA-N 1-[2-(dimethylamino)ethyl]-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-pyridin-4-ylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(=O)(=O)C=2C=CN=CC=2)=NC(C=2C=CC(NC(=O)NCCN(C)C)=CC=2)=N1 WHTKEOGWTDPAMG-FQEVSTJZSA-N 0.000 claims 1
WSQASKQHPDRTHP-INIZCTEOSA-N 1-[2-(dimethylamino)ethyl]-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=CC(NC(=O)NCCN(C)C)=CC=2)=N1 WSQASKQHPDRTHP-INIZCTEOSA-N 0.000 claims 1
OIVVYLULUYZVEL-SFHVURJKSA-N 1-[2-(dimethylamino)ethyl]-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(propan-2-ylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound N=1C(CS(=O)(=O)C(C)C)=CC(N2[C@H](COCC2)C)=NC=1C1=CC=C(NC(=O)NCCN(C)C)C=C1 OIVVYLULUYZVEL-SFHVURJKSA-N 0.000 claims 1
WSZHBWYYWWDWDD-IBGZPJMESA-N 1-[2-(dimethylamino)ethyl]-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(pyridin-4-ylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)C=2C=CN=CC=2)=NC(C=2C=CC(NC(=O)NCCN(C)C)=CC=2)=N1 WSZHBWYYWWDWDD-IBGZPJMESA-N 0.000 claims 1
AFORECSODDHZKV-FQEVSTJZSA-N 1-[2-(dimethylamino)ethyl]-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-[2-[2-(trifluoromethyl)phenyl]sulfonylpropan-2-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=NC(C=2C=CC(NC(=O)NCCN(C)C)=CC=2)=N1 AFORECSODDHZKV-FQEVSTJZSA-N 0.000 claims 1
MQEZAJAIAIOMIE-IBGZPJMESA-N 1-[2-(dimethylamino)ethyl]-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-[[2-(trifluoromethyl)phenyl]sulfonylmethyl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=NC(C=2C=CC(NC(=O)NCCN(C)C)=CC=2)=N1 MQEZAJAIAIOMIE-IBGZPJMESA-N 0.000 claims 1
WBMKUYGEZIGGHP-IBGZPJMESA-N 1-[2-(dimethylamino)ethyl]-3-[4-[4-[(4-fluorophenyl)sulfonylmethyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)C=2C=CC(F)=CC=2)=NC(C=2C=CC(NC(=O)NCCN(C)C)=CC=2)=N1 WBMKUYGEZIGGHP-IBGZPJMESA-N 0.000 claims 1
UMGDSOJYCGUVEH-FQEVSTJZSA-N 1-[2-(dimethylamino)ethyl]-3-[4-[4-[2-(4-fluorophenyl)sulfonylpropan-2-yl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(=O)(=O)C=2C=CC(F)=CC=2)=NC(C=2C=CC(NC(=O)NCCN(C)C)=CC=2)=N1 UMGDSOJYCGUVEH-FQEVSTJZSA-N 0.000 claims 1
DABURPDWKWEUQS-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-3-[4-[4-morpholin-4-yl-6-(propan-2-ylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound N=1C(CS(=O)(=O)C(C)C)=CC(N2CCOCC2)=NC=1C1=CC=C(NC(=O)NCCN(C)C)C=C1 DABURPDWKWEUQS-UHFFFAOYSA-N 0.000 claims 1
GFUUENHWYJZZJN-ZDUSSCGKSA-N 1-[2-(dimethylamino)ethyl]-3-[5-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]-1,3-thiazol-2-yl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2SC(NC(=O)NCCN(C)C)=NC=2)=N1 GFUUENHWYJZZJN-ZDUSSCGKSA-N 0.000 claims 1
YQAGAXQDIGKENJ-ZDUSSCGKSA-N 1-[2-chloro-4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=C(Cl)C(NC(=O)NCC)=CC=C1C1=NC(CS(C)(=O)=O)=CC(N2[C@H](COCC2)C)=N1 YQAGAXQDIGKENJ-ZDUSSCGKSA-N 0.000 claims 1
DJPKDWDEPSCWCS-INIZCTEOSA-N 1-[2-chloro-4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]-3-phenylurea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=C(Cl)C(NC(=O)NC=3C=CC=CC=3)=CC=2)=N1 DJPKDWDEPSCWCS-INIZCTEOSA-N 0.000 claims 1
YVUHSPWBTRIGLP-HNNXBMFYSA-N 1-[2-fluoro-4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]-3-(4-fluorophenyl)urea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=C(F)C(NC(=O)NC=3C=CC(F)=CC=3)=CC=2)=N1 YVUHSPWBTRIGLP-HNNXBMFYSA-N 0.000 claims 1
CDIWPIVFIKRXMY-LBPRGKRZSA-N 1-[2-fluoro-4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]-3-methylurea Chemical compound C1=C(F)C(NC(=O)NC)=CC=C1C1=NC(CS(C)(=O)=O)=CC(N2[C@H](COCC2)C)=N1 CDIWPIVFIKRXMY-LBPRGKRZSA-N 0.000 claims 1
JFDPOWZHAZRLHU-INIZCTEOSA-N 1-[2-fluoro-4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]-3-phenylurea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=C(F)C(NC(=O)NC=3C=CC=CC=3)=CC=2)=N1 JFDPOWZHAZRLHU-INIZCTEOSA-N 0.000 claims 1
BXNWPWRQTWNDNC-KRWDZBQOSA-N 1-[2-methoxy-4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]-3-(4-methoxyphenyl)urea Chemical compound C1=CC(OC)=CC=C1NC(=O)NC1=CC=C(C=2N=C(C=C(CS(C)(=O)=O)N=2)N2[C@H](COCC2)C)C=C1OC BXNWPWRQTWNDNC-KRWDZBQOSA-N 0.000 claims 1
KONFACDZZBFNSJ-SFHVURJKSA-N 1-[2-methyl-4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]-3-phenylurea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=C(C)C(NC(=O)NC=3C=CC=CC=3)=CC=2)=N1 KONFACDZZBFNSJ-SFHVURJKSA-N 0.000 claims 1
RHRJGYWUGBZFRO-KRWDZBQOSA-N 1-[3-(dimethylamino)propyl]-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=CC(NC(=O)NCCCN(C)C)=CC=2)=N1 RHRJGYWUGBZFRO-KRWDZBQOSA-N 0.000 claims 1
MVRLIJFJOKWSFW-KRWDZBQOSA-N 1-[3-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]-3-phenylurea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=C(NC(=O)NC=3C=CC=CC=3)C=CC=2)=N1 MVRLIJFJOKWSFW-KRWDZBQOSA-N 0.000 claims 1
SVDVPQBYVOYJRN-HNNXBMFYSA-N 1-[3-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]-3-propan-2-ylurea Chemical compound CC(C)NC(=O)NC1=CC=CC(C=2N=C(C=C(CS(C)(=O)=O)N=2)N2[C@H](COCC2)C)=C1 SVDVPQBYVOYJRN-HNNXBMFYSA-N 0.000 claims 1
CXPULTIEWIFTHS-UHFFFAOYSA-N 1-[4-(dimethylamino)butyl]-3-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCCCCN(C)C)=CC=C1C1=NC(CS(C)(=O)=O)=CC(N2CCOCC2)=N1 CXPULTIEWIFTHS-UHFFFAOYSA-N 0.000 claims 1
LBJDMQJOKQVDCD-BLNXRSMSSA-N 1-[4-[4-(1-adamantylsulfonylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-cyclopropylurea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)C23CC4CC(CC(C4)C2)C3)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 LBJDMQJOKQVDCD-BLNXRSMSSA-N 0.000 claims 1
XFEIAWQYSDKDER-AWEZNQCLSA-N 1-[4-[4-(1h-imidazol-2-ylsulfonylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(CS(=O)(=O)C=2NC=CN=2)=CC(N2[C@H](COCC2)C)=N1 XFEIAWQYSDKDER-AWEZNQCLSA-N 0.000 claims 1
VVNSSOMAEPPTBD-IBGZPJMESA-N 1-[4-[4-(2-cyclohexylsulfonylpropan-2-yl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-(2-hydroxyethyl)urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(=O)(=O)C2CCCCC2)=NC(C=2C=CC(NC(=O)NCCO)=CC=2)=N1 VVNSSOMAEPPTBD-IBGZPJMESA-N 0.000 claims 1
DNYGDPKKRCSEQM-NRFANRHFSA-N 1-[4-[4-(2-cyclohexylsulfonylpropan-2-yl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-[2-(dimethylamino)ethyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(=O)(=O)C2CCCCC2)=NC(C=2C=CC(NC(=O)NCCN(C)C)=CC=2)=N1 DNYGDPKKRCSEQM-NRFANRHFSA-N 0.000 claims 1
DBFAANAHGHWNER-IBGZPJMESA-N 1-[4-[4-(2-cyclohexylsulfonylpropan-2-yl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2[C@H](COCC2)C)=CC(C(C)(C)S(=O)(=O)C2CCCCC2)=N1 DBFAANAHGHWNER-IBGZPJMESA-N 0.000 claims 1
SDIBIKRXRTXMMM-SFHVURJKSA-N 1-[4-[4-(2-cyclopentylsulfonylpropan-2-yl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-(2-hydroxyethyl)urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(=O)(=O)C2CCCC2)=NC(C=2C=CC(NC(=O)NCCO)=CC=2)=N1 SDIBIKRXRTXMMM-SFHVURJKSA-N 0.000 claims 1
OFILJRWGRWBGQU-FQEVSTJZSA-N 1-[4-[4-(2-cyclopentylsulfonylpropan-2-yl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-[2-(dimethylamino)ethyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(=O)(=O)C2CCCC2)=NC(C=2C=CC(NC(=O)NCCN(C)C)=CC=2)=N1 OFILJRWGRWBGQU-FQEVSTJZSA-N 0.000 claims 1
OTPJUYCDMXOTLQ-SFHVURJKSA-N 1-[4-[4-(2-cyclopentylsulfonylpropan-2-yl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-cyclopropylurea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(=O)(=O)C2CCCC2)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 OTPJUYCDMXOTLQ-SFHVURJKSA-N 0.000 claims 1
CZWHXPCXPGQFDN-SFHVURJKSA-N 1-[4-[4-(2-cyclopentylsulfonylpropan-2-yl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2[C@H](COCC2)C)=CC(C(C)(C)S(=O)(=O)C2CCCC2)=N1 CZWHXPCXPGQFDN-SFHVURJKSA-N 0.000 claims 1
JKSCTYIFRJFQOQ-KRWDZBQOSA-N 1-[4-[4-(2-cyclopentylsulfonylpropan-2-yl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2[C@H](COCC2)C)=CC(C(C)(C)S(=O)(=O)C2CCCC2)=N1 JKSCTYIFRJFQOQ-KRWDZBQOSA-N 0.000 claims 1
OHTPYNDSKZCIAV-KRWDZBQOSA-N 1-[4-[4-(2-cyclopropylsulfonylpropan-2-yl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-(1-hydroxy-2-methylpropan-2-yl)urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(=O)(=O)C2CC2)=NC(C=2C=CC(NC(=O)NC(C)(C)CO)=CC=2)=N1 OHTPYNDSKZCIAV-KRWDZBQOSA-N 0.000 claims 1
WMEWGPALKBZXNX-KRWDZBQOSA-N 1-[4-[4-(2-cyclopropylsulfonylpropan-2-yl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-(1-methylpyrazol-4-yl)urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(=O)(=O)C2CC2)=NC(C=2C=CC(NC(=O)NC3=CN(C)N=C3)=CC=2)=N1 WMEWGPALKBZXNX-KRWDZBQOSA-N 0.000 claims 1
NOINGWNJTOTKSL-INIZCTEOSA-N 1-[4-[4-(2-cyclopropylsulfonylpropan-2-yl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-(2-hydroxyethyl)urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(=O)(=O)C2CC2)=NC(C=2C=CC(NC(=O)NCCO)=CC=2)=N1 NOINGWNJTOTKSL-INIZCTEOSA-N 0.000 claims 1
POODHXSOLJBDIZ-SFHVURJKSA-N 1-[4-[4-(2-cyclopropylsulfonylpropan-2-yl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-[2-(dimethylamino)ethyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(=O)(=O)C2CC2)=NC(C=2C=CC(NC(=O)NCCN(C)C)=CC=2)=N1 POODHXSOLJBDIZ-SFHVURJKSA-N 0.000 claims 1
WAXVCBJHRWZWKQ-INIZCTEOSA-N 1-[4-[4-(2-cyclopropylsulfonylpropan-2-yl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2[C@H](COCC2)C)=CC(C(C)(C)S(=O)(=O)C2CC2)=N1 WAXVCBJHRWZWKQ-INIZCTEOSA-N 0.000 claims 1
ZNGMCQPYYRGYPD-INIZCTEOSA-N 1-[4-[4-(2-ethylsulfonylpropan-2-yl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-(2-hydroxyethyl)urea Chemical compound N=1C(C(C)(C)S(=O)(=O)CC)=CC(N2[C@H](COCC2)C)=NC=1C1=CC=C(NC(=O)NCCO)C=C1 ZNGMCQPYYRGYPD-INIZCTEOSA-N 0.000 claims 1
KFNDXYMSUDVWRT-HNNXBMFYSA-N 1-[4-[4-(2-ethylsulfonylpropan-2-yl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-methylurea Chemical compound N=1C(C(C)(C)S(=O)(=O)CC)=CC(N2[C@H](COCC2)C)=NC=1C1=CC=C(NC(=O)NC)C=C1 KFNDXYMSUDVWRT-HNNXBMFYSA-N 0.000 claims 1
CCRIEIVGMWRJAB-KRWDZBQOSA-N 1-[4-[4-(2-hydroxyethylsulfonylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-[(1-methylpyrazol-4-yl)methyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)CCO)=NC(C=2C=CC(NC(=O)NCC3=CN(C)N=C3)=CC=2)=N1 CCRIEIVGMWRJAB-KRWDZBQOSA-N 0.000 claims 1
CSMXWPJZMQUOHG-AWEZNQCLSA-N 1-[4-[4-(2-hydroxyethylsulfonylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(CS(=O)(=O)CCO)=CC(N2[C@H](COCC2)C)=N1 CSMXWPJZMQUOHG-AWEZNQCLSA-N 0.000 claims 1
ADSJRHKMNABZPP-AWEZNQCLSA-N 1-[4-[4-(2-hydroxypropan-2-yl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-(1,2-oxazol-3-yl)urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)O)=NC(C=2C=CC(NC(=O)NC3=NOC=C3)=CC=2)=N1 ADSJRHKMNABZPP-AWEZNQCLSA-N 0.000 claims 1
FXUUZFGVABBCRU-INIZCTEOSA-N 1-[4-[4-(2-hydroxypropan-2-yl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-[(1-methylpyrazol-4-yl)methyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)O)=NC(C=2C=CC(NC(=O)NCC3=CN(C)N=C3)=CC=2)=N1 FXUUZFGVABBCRU-INIZCTEOSA-N 0.000 claims 1
CKZSYPFTDYPSIG-IBGZPJMESA-N 1-[4-[4-(2-tert-butylsulfonylpropan-2-yl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-[2-(dimethylamino)ethyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(=O)(=O)C(C)(C)C)=NC(C=2C=CC(NC(=O)NCCN(C)C)=CC=2)=N1 CKZSYPFTDYPSIG-IBGZPJMESA-N 0.000 claims 1
FXUDFACTRIRDPL-SFHVURJKSA-N 1-[4-[4-(2-tert-butylsulfonylpropan-2-yl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-cyclobutylurea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(=O)(=O)C(C)(C)C)=NC(C=2C=CC(NC(=O)NC3CCC3)=CC=2)=N1 FXUDFACTRIRDPL-SFHVURJKSA-N 0.000 claims 1
AZZBLRJZEGNJRB-KRWDZBQOSA-N 1-[4-[4-(2-tert-butylsulfonylpropan-2-yl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-cyclopropylurea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(=O)(=O)C(C)(C)C)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 AZZBLRJZEGNJRB-KRWDZBQOSA-N 0.000 claims 1
WETZBSQRUHDIIG-KRWDZBQOSA-N 1-[4-[4-(2-tert-butylsulfonylpropan-2-yl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2[C@H](COCC2)C)=CC(C(C)(C)S(=O)(=O)C(C)(C)C)=N1 WETZBSQRUHDIIG-KRWDZBQOSA-N 0.000 claims 1
UPYJAKIIEVXRHA-INIZCTEOSA-N 1-[4-[4-(2-tert-butylsulfonylpropan-2-yl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2[C@H](COCC2)C)=CC(C(C)(C)S(=O)(=O)C(C)(C)C)=N1 UPYJAKIIEVXRHA-INIZCTEOSA-N 0.000 claims 1
UHTQWDYORFGMDD-SFHVURJKSA-N 1-[4-[4-(azepane-1-carbonyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-cyclopropylurea Chemical compound C[C@H]1COCCN1C1=CC(C(=O)N2CCCCCC2)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 UHTQWDYORFGMDD-SFHVURJKSA-N 0.000 claims 1
DILAYZBVHPHWNN-NRFANRHFSA-N 1-[4-[4-(benzenesulfonylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-(1-methylpiperidin-4-yl)urea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)C=2C=CC=CC=2)=NC(C=2C=CC(NC(=O)NC3CCN(C)CC3)=CC=2)=N1 DILAYZBVHPHWNN-NRFANRHFSA-N 0.000 claims 1
JTIBSDJIWPCRAM-IBGZPJMESA-N 1-[4-[4-(benzenesulfonylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-(2-methoxyethyl)urea Chemical compound C1=CC(NC(=O)NCCOC)=CC=C1C1=NC(CS(=O)(=O)C=2C=CC=CC=2)=CC(N2[C@H](COCC2)C)=N1 JTIBSDJIWPCRAM-IBGZPJMESA-N 0.000 claims 1
QWWUYYOOQLAANR-FQEVSTJZSA-N 1-[4-[4-(benzenesulfonylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-[2-(dimethylamino)ethyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)C=2C=CC=CC=2)=NC(C=2C=CC(NC(=O)NCCN(C)C)=CC=2)=N1 QWWUYYOOQLAANR-FQEVSTJZSA-N 0.000 claims 1
FZOVSMTZLOQRDS-SFHVURJKSA-N 1-[4-[4-(benzenesulfonylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-cyclopropylurea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)C=2C=CC=CC=2)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 FZOVSMTZLOQRDS-SFHVURJKSA-N 0.000 claims 1
GTHNAHNOUJLLJA-SFHVURJKSA-N 1-[4-[4-(benzenesulfonylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(CS(=O)(=O)C=2C=CC=CC=2)=CC(N2[C@H](COCC2)C)=N1 GTHNAHNOUJLLJA-SFHVURJKSA-N 0.000 claims 1
QYBUQRBNDZWLCQ-KRWDZBQOSA-N 1-[4-[4-(benzenesulfonylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(CS(=O)(=O)C=2C=CC=CC=2)=CC(N2[C@H](COCC2)C)=N1 QYBUQRBNDZWLCQ-KRWDZBQOSA-N 0.000 claims 1
ACVUOTPAASOOTB-NRFANRHFSA-N 1-[4-[4-(benzenesulfonylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-phenylurea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)C=2C=CC=CC=2)=NC(C=2C=CC(NC(=O)NC=3C=CC=CC=3)=CC=2)=N1 ACVUOTPAASOOTB-NRFANRHFSA-N 0.000 claims 1
UGPOVSHXAHVNTA-UHFFFAOYSA-N 1-[4-[4-(benzenesulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]-3-[2-(dimethylamino)ethyl]urea Chemical compound C1=CC(NC(=O)NCCN(C)C)=CC=C1C1=NC(CS(=O)(=O)C=2C=CC=CC=2)=CC(N2CCOCC2)=N1 UGPOVSHXAHVNTA-UHFFFAOYSA-N 0.000 claims 1
LAVKCCJJEIATCC-UHFFFAOYSA-N 1-[4-[4-(benzenesulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]-3-cyclopropylurea Chemical compound C=1C=C(C=2N=C(C=C(CS(=O)(=O)C=3C=CC=CC=3)N=2)N2CCOCC2)C=CC=1NC(=O)NC1CC1 LAVKCCJJEIATCC-UHFFFAOYSA-N 0.000 claims 1
ANAZBSKBNMTSJE-UHFFFAOYSA-N 1-[4-[4-(benzenesulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(CS(=O)(=O)C=2C=CC=CC=2)=CC(N2CCOCC2)=N1 ANAZBSKBNMTSJE-UHFFFAOYSA-N 0.000 claims 1
DGWGLTIOQGMJEB-FQEVSTJZSA-N 1-[4-[4-(cyclohexylsulfonylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-[2-(dimethylamino)ethyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)C2CCCCC2)=NC(C=2C=CC(NC(=O)NCCN(C)C)=CC=2)=N1 DGWGLTIOQGMJEB-FQEVSTJZSA-N 0.000 claims 1
UNBMFXYJZYOIRH-SFHVURJKSA-N 1-[4-[4-(cyclohexylsulfonylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(CS(=O)(=O)C2CCCCC2)=CC(N2[C@H](COCC2)C)=N1 UNBMFXYJZYOIRH-SFHVURJKSA-N 0.000 claims 1
SBBHUNIYYBLVTE-KRWDZBQOSA-N 1-[4-[4-(cyclohexylsulfonylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(CS(=O)(=O)C2CCCCC2)=CC(N2[C@H](COCC2)C)=N1 SBBHUNIYYBLVTE-KRWDZBQOSA-N 0.000 claims 1
ALCBKLBQKQJAIF-IBGZPJMESA-N 1-[4-[4-(cyclopentylsulfonylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-[2-(dimethylamino)ethyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)C2CCCC2)=NC(C=2C=CC(NC(=O)NCCN(C)C)=CC=2)=N1 ALCBKLBQKQJAIF-IBGZPJMESA-N 0.000 claims 1
QJFQODKWFOTQIJ-INIZCTEOSA-N 1-[4-[4-(cyclopropylsulfonylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-(1-hydroxy-2-methylpropan-2-yl)urea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)C2CC2)=NC(C=2C=CC(NC(=O)NC(C)(C)CO)=CC=2)=N1 QJFQODKWFOTQIJ-INIZCTEOSA-N 0.000 claims 1
FFHHQGYPWPNTOR-INIZCTEOSA-N 1-[4-[4-(cyclopropylsulfonylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-(1-methylpyrazol-4-yl)urea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)C2CC2)=NC(C=2C=CC(NC(=O)NC3=CN(C)N=C3)=CC=2)=N1 FFHHQGYPWPNTOR-INIZCTEOSA-N 0.000 claims 1
HGWQAKUXSFTMMQ-KRWDZBQOSA-N 1-[4-[4-(cyclopropylsulfonylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-[2-(dimethylamino)ethyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)C2CC2)=NC(C=2C=CC(NC(=O)NCCN(C)C)=CC=2)=N1 HGWQAKUXSFTMMQ-KRWDZBQOSA-N 0.000 claims 1
OUCWUYFBSCDQBR-HNNXBMFYSA-N 1-[4-[4-(cyclopropylsulfonylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(CS(=O)(=O)C2CC2)=CC(N2[C@H](COCC2)C)=N1 OUCWUYFBSCDQBR-HNNXBMFYSA-N 0.000 claims 1
WIGLDOFZVMGZJM-AWEZNQCLSA-N 1-[4-[4-(cyclopropylsulfonylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(CS(=O)(=O)C2CC2)=CC(N2[C@H](COCC2)C)=N1 WIGLDOFZVMGZJM-AWEZNQCLSA-N 0.000 claims 1
OOYUBHDHJMPWSZ-ZDUSSCGKSA-N 1-[4-[4-(hydroxymethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-(1,2-oxazol-3-yl)urea Chemical compound C[C@H]1COCCN1C1=CC(CO)=NC(C=2C=CC(NC(=O)NC3=NOC=C3)=CC=2)=N1 OOYUBHDHJMPWSZ-ZDUSSCGKSA-N 0.000 claims 1
YQQFYUANUJZTEF-HNNXBMFYSA-N 1-[4-[4-(hydroxymethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-[(1-methylpyrazol-4-yl)methyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CO)=NC(C=2C=CC(NC(=O)NCC3=CN(C)N=C3)=CC=2)=N1 YQQFYUANUJZTEF-HNNXBMFYSA-N 0.000 claims 1
GFKSGOJBUYBTKM-LBPRGKRZSA-N 1-[4-[4-(hydroxymethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(CO)=CC(N2[C@H](COCC2)C)=N1 GFKSGOJBUYBTKM-LBPRGKRZSA-N 0.000 claims 1
OWJPORUXPOAQQG-INIZCTEOSA-N 1-[4-[4-(hydroxymethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-phenylurea Chemical compound C[C@H]1COCCN1C1=CC(CO)=NC(C=2C=CC(NC(=O)NC=3C=CC=CC=3)=CC=2)=N1 OWJPORUXPOAQQG-INIZCTEOSA-N 0.000 claims 1
DEZBYKARHQDASH-KRWDZBQOSA-N 1-[4-[4-(methoxymethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-phenylurea Chemical compound N=1C(COC)=CC(N2[C@H](COCC2)C)=NC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1 DEZBYKARHQDASH-KRWDZBQOSA-N 0.000 claims 1
VCKVUDULJVVTDP-UHFFFAOYSA-N 1-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]-3-(1,2-oxazol-3-yl)urea Chemical compound N=1C(CS(=O)(=O)C)=CC(N2CCOCC2)=NC=1C(C=C1)=CC=C1NC(=O)NC=1C=CON=1 VCKVUDULJVVTDP-UHFFFAOYSA-N 0.000 claims 1
ASACMSBARHIFFO-UHFFFAOYSA-N 1-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]-3-(2-morpholin-4-ylethyl)urea Chemical compound N=1C(CS(=O)(=O)C)=CC(N2CCOCC2)=NC=1C(C=C1)=CC=C1NC(=O)NCCN1CCOCC1 ASACMSBARHIFFO-UHFFFAOYSA-N 0.000 claims 1
WZQXRQNFRALUDT-UHFFFAOYSA-N 1-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]-3-(2-thiophen-2-ylethyl)urea Chemical compound N=1C(CS(=O)(=O)C)=CC(N2CCOCC2)=NC=1C(C=C1)=CC=C1NC(=O)NCCC1=CC=CS1 WZQXRQNFRALUDT-UHFFFAOYSA-N 0.000 claims 1
IURXWXLUFYHLJA-UHFFFAOYSA-N 1-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]-3-(oxan-4-yl)urea Chemical compound N=1C(CS(=O)(=O)C)=CC(N2CCOCC2)=NC=1C(C=C1)=CC=C1NC(=O)NC1CCOCC1 IURXWXLUFYHLJA-UHFFFAOYSA-N 0.000 claims 1
HCTRISCGYGPNFQ-UHFFFAOYSA-N 1-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]-3-[2-(2-oxoimidazolidin-1-yl)ethyl]urea Chemical compound N=1C(CS(=O)(=O)C)=CC(N2CCOCC2)=NC=1C(C=C1)=CC=C1NC(=O)NCCN1CCNC1=O HCTRISCGYGPNFQ-UHFFFAOYSA-N 0.000 claims 1
YFKMIADYQGZZNO-UHFFFAOYSA-N 1-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound N=1C(CS(=O)(=O)C)=CC(N2CCOCC2)=NC=1C(C=C1)=CC=C1NC(=O)NC1=CC=C(C(F)(F)F)C=C1 YFKMIADYQGZZNO-UHFFFAOYSA-N 0.000 claims 1
RFNDQOYBEANZJZ-UHFFFAOYSA-N 1-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]-3-pentylurea Chemical compound C1=CC(NC(=O)NCCCCC)=CC=C1C1=NC(CS(C)(=O)=O)=CC(N2CCOCC2)=N1 RFNDQOYBEANZJZ-UHFFFAOYSA-N 0.000 claims 1
ZMLACPVRINOLLD-UHFFFAOYSA-N 1-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]-3-phenylurea Chemical compound N=1C(CS(=O)(=O)C)=CC(N2CCOCC2)=NC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1 ZMLACPVRINOLLD-UHFFFAOYSA-N 0.000 claims 1
USAFYFFXVOMAFQ-UHFFFAOYSA-N 1-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]-3-propylurea Chemical compound C1=CC(NC(=O)NCCC)=CC=C1C1=NC(CS(C)(=O)=O)=CC(N2CCOCC2)=N1 USAFYFFXVOMAFQ-UHFFFAOYSA-N 0.000 claims 1
LSXUKQZDLLRLGQ-UHFFFAOYSA-N 1-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]-3-thiophen-2-ylurea Chemical compound N=1C(CS(=O)(=O)C)=CC(N2CCOCC2)=NC=1C(C=C1)=CC=C1NC(=O)NC1=CC=CS1 LSXUKQZDLLRLGQ-UHFFFAOYSA-N 0.000 claims 1
XSXMKTBIIJDUDF-KRWDZBQOSA-N 1-[4-[4-(tert-butylsulfonylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-cyclobutylurea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)C(C)(C)C)=NC(C=2C=CC(NC(=O)NC3CCC3)=CC=2)=N1 XSXMKTBIIJDUDF-KRWDZBQOSA-N 0.000 claims 1
XOWMGWJLWFRZDR-INIZCTEOSA-N 1-[4-[4-(tert-butylsulfonylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(CS(=O)(=O)C(C)(C)C)=CC(N2[C@H](COCC2)C)=N1 XOWMGWJLWFRZDR-INIZCTEOSA-N 0.000 claims 1
UYRBJQGLIVVDRN-INIZCTEOSA-N 1-[4-[4-[(2-chlorophenyl)sulfanylmethyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(CSC=2C(=CC=CC=2)Cl)=CC(N2[C@H](COCC2)C)=N1 UYRBJQGLIVVDRN-INIZCTEOSA-N 0.000 claims 1
NTFHKEZDHQKLGQ-KRWDZBQOSA-N 1-[4-[4-[(2-methoxyphenyl)sulfanylmethyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(CSC=2C(=CC=CC=2)OC)=CC(N2[C@H](COCC2)C)=N1 NTFHKEZDHQKLGQ-KRWDZBQOSA-N 0.000 claims 1
ICZGTTIRHNBKRV-SFHVURJKSA-N 1-[4-[4-[(3,5-difluorophenyl)sulfonylmethyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-[2-(dimethylamino)ethyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)C=2C=C(F)C=C(F)C=2)=NC(C=2C=CC(NC(=O)NCCN(C)C)=CC=2)=N1 ICZGTTIRHNBKRV-SFHVURJKSA-N 0.000 claims 1
LWCGRGANDIERJT-INIZCTEOSA-N 1-[4-[4-[(3,5-difluorophenyl)sulfonylmethyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(CS(=O)(=O)C=2C=C(F)C=C(F)C=2)=CC(N2[C@H](COCC2)C)=N1 LWCGRGANDIERJT-INIZCTEOSA-N 0.000 claims 1
BXQUULKBFBPJTQ-SFHVURJKSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]-3-(1-methylpiperidin-4-yl)urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(C)(=O)=O)=NC(C=2C=CC(NC(=O)NC3CCN(C)CC3)=CC=2)=N1 BXQUULKBFBPJTQ-SFHVURJKSA-N 0.000 claims 1
XYIYUPOBBOQXBI-INIZCTEOSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]-3-(1h-pyrazol-5-ylmethyl)urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(C)(=O)=O)=NC(C=2C=CC(NC(=O)NCC3=NNC=C3)=CC=2)=N1 XYIYUPOBBOQXBI-INIZCTEOSA-N 0.000 claims 1
CGEHEIKICCFHLP-KRWDZBQOSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]-3-(2-methylpropyl)urea Chemical compound C1=CC(NC(=O)NCC(C)C)=CC=C1C1=NC(N2[C@H](COCC2)C)=CC(C(C)(C)S(C)(=O)=O)=N1 CGEHEIKICCFHLP-KRWDZBQOSA-N 0.000 claims 1
OPMUVPCHUOEYTR-SFHVURJKSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]-3-(pyridin-4-ylmethyl)urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(C)(=O)=O)=NC(C=2C=CC(NC(=O)NCC=3C=CN=CC=3)=CC=2)=N1 OPMUVPCHUOEYTR-SFHVURJKSA-N 0.000 claims 1
CETMLWSPWLMABQ-KRWDZBQOSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]-3-[(1-methylpyrazol-3-yl)methyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(C)(=O)=O)=NC(C=2C=CC(NC(=O)NCC3=NN(C)C=C3)=CC=2)=N1 CETMLWSPWLMABQ-KRWDZBQOSA-N 0.000 claims 1
KPAQILVSMZLPQZ-KRWDZBQOSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]-3-[(1-methylpyrazol-4-yl)methyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(C)(=O)=O)=NC(C=2C=CC(NC(=O)NCC3=CN(C)N=C3)=CC=2)=N1 KPAQILVSMZLPQZ-KRWDZBQOSA-N 0.000 claims 1
DGHVZGZXFSVGCC-INIZCTEOSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]-3-[(5-methyl-1,2-oxazol-3-yl)methyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(C)(=O)=O)=NC(C=2C=CC(NC(=O)NCC3=NOC(C)=C3)=CC=2)=N1 DGHVZGZXFSVGCC-INIZCTEOSA-N 0.000 claims 1
BEFAEYHZHBLCFB-INIZCTEOSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]-3-propan-2-ylurea Chemical compound C1=CC(NC(=O)NC(C)C)=CC=C1C1=NC(N2[C@H](COCC2)C)=CC(C(C)(C)S(C)(=O)=O)=N1 BEFAEYHZHBLCFB-INIZCTEOSA-N 0.000 claims 1
XYLRMQKCSAQOHU-INIZCTEOSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]-3-propylurea Chemical compound C1=CC(NC(=O)NCCC)=CC=C1C1=NC(N2[C@H](COCC2)C)=CC(C(C)(C)S(C)(=O)=O)=N1 XYLRMQKCSAQOHU-INIZCTEOSA-N 0.000 claims 1
SWZSACACGJMLFY-SFHVURJKSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-propan-2-ylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]-3-(1-methylpyrazol-4-yl)urea Chemical compound N=1C(C(C)(C)S(=O)(=O)C(C)C)=CC(N2[C@H](COCC2)C)=NC=1C(C=C1)=CC=C1NC(=O)NC=1C=NN(C)C=1 SWZSACACGJMLFY-SFHVURJKSA-N 0.000 claims 1
MCFFLISOIOYQQK-IBGZPJMESA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-propan-2-ylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]-3-(2-methylpropyl)urea Chemical compound C1=CC(NC(=O)NCC(C)C)=CC=C1C1=NC(N2[C@H](COCC2)C)=CC(C(C)(C)S(=O)(=O)C(C)C)=N1 MCFFLISOIOYQQK-IBGZPJMESA-N 0.000 claims 1
ZUHPAUCFIDXXAN-IBGZPJMESA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-propan-2-ylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound N=1C(C(C)(C)S(=O)(=O)C(C)C)=CC(N2[C@H](COCC2)C)=NC=1C(C=C1)=CC=C1NC(=O)NC1=CC=C(C(F)(F)F)C=C1 ZUHPAUCFIDXXAN-IBGZPJMESA-N 0.000 claims 1
JRRQXYNYJMTENV-SFHVURJKSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-propan-2-ylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]-3-propan-2-ylurea Chemical compound C1=CC(NC(=O)NC(C)C)=CC=C1C1=NC(N2[C@H](COCC2)C)=CC(C(C)(C)S(=O)(=O)C(C)C)=N1 JRRQXYNYJMTENV-SFHVURJKSA-N 0.000 claims 1
NBPGSMKTPYSQMG-SFHVURJKSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-propan-2-ylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]-3-propylurea Chemical compound C1=CC(NC(=O)NCCC)=CC=C1C1=NC(N2[C@H](COCC2)C)=CC(C(C)(C)S(=O)(=O)C(C)C)=N1 NBPGSMKTPYSQMG-SFHVURJKSA-N 0.000 claims 1
LKZKNYQRKOHXAM-AWEZNQCLSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]-3-(1,2-oxazol-3-yl)urea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=CC(NC(=O)NC3=NOC=C3)=CC=2)=N1 LKZKNYQRKOHXAM-AWEZNQCLSA-N 0.000 claims 1
MVYLHNNMIGOXIV-HNNXBMFYSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]-3-(1,3-thiazol-5-ylmethyl)urea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=CC(NC(=O)NCC=3SC=NC=3)=CC=2)=N1 MVYLHNNMIGOXIV-HNNXBMFYSA-N 0.000 claims 1
JGYAEKZESLTYSC-HNNXBMFYSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]-3-(1-methylpyrazol-4-yl)urea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=CC(NC(=O)NC3=CN(C)N=C3)=CC=2)=N1 JGYAEKZESLTYSC-HNNXBMFYSA-N 0.000 claims 1
XZRFXYOQUQCDPF-INIZCTEOSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]-3-(2-methylpropyl)urea Chemical compound C1=CC(NC(=O)NCC(C)C)=CC=C1C1=NC(CS(C)(=O)=O)=CC(N2[C@H](COCC2)C)=N1 XZRFXYOQUQCDPF-INIZCTEOSA-N 0.000 claims 1
YURFRHMUNNUYQF-SFHVURJKSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]-3-(2-morpholin-4-ylethyl)urea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=CC(NC(=O)NCCN3CCOCC3)=CC=2)=N1 YURFRHMUNNUYQF-SFHVURJKSA-N 0.000 claims 1
SFNVTSCILFLWLW-HNNXBMFYSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]-3-(2-oxo-1h-pyridin-4-yl)urea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=CC(NC(=O)NC3=CC(=O)NC=C3)=CC=2)=N1 SFNVTSCILFLWLW-HNNXBMFYSA-N 0.000 claims 1
SGFUKRIVRLQPCF-SFHVURJKSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]-3-(2-pyridin-2-ylethyl)urea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=CC(NC(=O)NCCC=3N=CC=CC=3)=CC=2)=N1 SGFUKRIVRLQPCF-SFHVURJKSA-N 0.000 claims 1
PWKJFRFHXIPNGB-AWEZNQCLSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]-3-(5-methyl-1,2-oxazol-3-yl)urea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=CC(NC(=O)NC3=NOC(C)=C3)=CC=2)=N1 PWKJFRFHXIPNGB-AWEZNQCLSA-N 0.000 claims 1
WVUPAMGYKJHGSB-HNNXBMFYSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]-3-(6-oxo-1h-pyridin-2-yl)urea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=CC(NC(=O)NC=3NC(=O)C=CC=3)=CC=2)=N1 WVUPAMGYKJHGSB-HNNXBMFYSA-N 0.000 claims 1
IUSQRRNQSUITKA-KRWDZBQOSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]-3-(pyridin-2-ylmethyl)urea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=CC(NC(=O)NCC=3N=CC=CC=3)=CC=2)=N1 IUSQRRNQSUITKA-KRWDZBQOSA-N 0.000 claims 1
CCDPJLDJNZYUPF-KRWDZBQOSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]-3-(pyridin-3-ylmethyl)urea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=CC(NC(=O)NCC=3C=NC=CC=3)=CC=2)=N1 CCDPJLDJNZYUPF-KRWDZBQOSA-N 0.000 claims 1
FHWGCPAUGLPPNG-KRWDZBQOSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]-3-(pyridin-4-ylmethyl)urea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=CC(NC(=O)NCC=3C=CN=CC=3)=CC=2)=N1 FHWGCPAUGLPPNG-KRWDZBQOSA-N 0.000 claims 1
BFEDHYCCHWSSLE-HNNXBMFYSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]-3-[(5-methyl-1,2-oxazol-3-yl)methyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=CC(NC(=O)NCC3=NOC(C)=C3)=CC=2)=N1 BFEDHYCCHWSSLE-HNNXBMFYSA-N 0.000 claims 1
BSYJWJPSLPCKAW-KRWDZBQOSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]-3-[(5-methylpyrazin-2-yl)methyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=CC(NC(=O)NCC=3N=CC(C)=NC=3)=CC=2)=N1 BSYJWJPSLPCKAW-KRWDZBQOSA-N 0.000 claims 1
NYPFEBBGVJOMNR-KRWDZBQOSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]-3-phenylurea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=CC(NC(=O)NC=3C=CC=CC=3)=CC=2)=N1 NYPFEBBGVJOMNR-KRWDZBQOSA-N 0.000 claims 1
AZQHFDKNKSLZSM-HNNXBMFYSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]-3-propan-2-ylurea Chemical compound C1=CC(NC(=O)NC(C)C)=CC=C1C1=NC(CS(C)(=O)=O)=CC(N2[C@H](COCC2)C)=N1 AZQHFDKNKSLZSM-HNNXBMFYSA-N 0.000 claims 1
BHALISJOSNGTTF-HNNXBMFYSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]-3-pyrimidin-2-ylurea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=CC(NC(=O)NC=3N=CC=CN=3)=CC=2)=N1 BHALISJOSNGTTF-HNNXBMFYSA-N 0.000 claims 1
WOHFEKYIVUQWEC-IBGZPJMESA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(propan-2-ylsulfonylmethyl)pyrimidin-2-yl]phenyl]-3-(1-methylpiperidin-4-yl)urea Chemical compound N=1C(CS(=O)(=O)C(C)C)=CC(N2[C@H](COCC2)C)=NC=1C(C=C1)=CC=C1NC(=O)NC1CCN(C)CC1 WOHFEKYIVUQWEC-IBGZPJMESA-N 0.000 claims 1
JZJRNDIKWODSNS-KRWDZBQOSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(propan-2-ylsulfonylmethyl)pyrimidin-2-yl]phenyl]-3-(1-methylpyrazol-4-yl)urea Chemical compound N=1C(CS(=O)(=O)C(C)C)=CC(N2[C@H](COCC2)C)=NC=1C(C=C1)=CC=C1NC(=O)NC=1C=NN(C)C=1 JZJRNDIKWODSNS-KRWDZBQOSA-N 0.000 claims 1
PWKKCTBZKPVCQZ-SFHVURJKSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(propan-2-ylsulfonylmethyl)pyrimidin-2-yl]phenyl]-3-(2-methylpropyl)urea Chemical compound C1=CC(NC(=O)NCC(C)C)=CC=C1C1=NC(CS(=O)(=O)C(C)C)=CC(N2[C@H](COCC2)C)=N1 PWKKCTBZKPVCQZ-SFHVURJKSA-N 0.000 claims 1
ZPJPVMATVRVKAG-SFHVURJKSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(propan-2-ylsulfonylmethyl)pyrimidin-2-yl]phenyl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound N=1C(CS(=O)(=O)C(C)C)=CC(N2[C@H](COCC2)C)=NC=1C(C=C1)=CC=C1NC(=O)NC1=CC=C(C(F)(F)F)C=C1 ZPJPVMATVRVKAG-SFHVURJKSA-N 0.000 claims 1
LWPHMGVLZJLTHM-KRWDZBQOSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(propan-2-ylsulfonylmethyl)pyrimidin-2-yl]phenyl]-3-propylurea Chemical compound C1=CC(NC(=O)NCCC)=CC=C1C1=NC(CS(=O)(=O)C(C)C)=CC(N2[C@H](COCC2)C)=N1 LWPHMGVLZJLTHM-KRWDZBQOSA-N 0.000 claims 1
WIGYSWWAEXPASX-IBGZPJMESA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(pyridin-4-ylsulfonylmethyl)pyrimidin-2-yl]phenyl]-3-[(1-methylpyrazol-4-yl)methyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)C=2C=CN=CC=2)=NC(C=2C=CC(NC(=O)NCC3=CN(C)N=C3)=CC=2)=N1 WIGYSWWAEXPASX-IBGZPJMESA-N 0.000 claims 1
OQJARORYDKIAFK-NRFANRHFSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-[(1-methylpiperidin-4-yl)oxymethyl]pyrimidin-2-yl]phenyl]-3-phenylurea Chemical compound C[C@H]1COCCN1C1=CC(COC2CCN(C)CC2)=NC(C=2C=CC(NC(=O)NC=3C=CC=CC=3)=CC=2)=N1 OQJARORYDKIAFK-NRFANRHFSA-N 0.000 claims 1
MACZVVKKJOLABN-FQEVSTJZSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-[(4-methylpiperazin-1-yl)methyl]pyrimidin-2-yl]phenyl]-3-[(1-methylpyrazol-4-yl)methyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CN2CCN(C)CC2)=NC(C=2C=CC(NC(=O)NCC3=CN(C)N=C3)=CC=2)=N1 MACZVVKKJOLABN-FQEVSTJZSA-N 0.000 claims 1
OFZVYFMMDUYCDP-NRFANRHFSA-N 1-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-[[(1-methylpiperidin-4-yl)amino]methyl]pyrimidin-2-yl]phenyl]-3-phenylurea Chemical compound C[C@H]1COCCN1C1=CC(CNC2CCN(C)CC2)=NC(C=2C=CC(NC(=O)NC=3C=CC=CC=3)=CC=2)=N1 OFZVYFMMDUYCDP-NRFANRHFSA-N 0.000 claims 1
FXEUPHFDPVLQLT-INIZCTEOSA-N 1-[4-[4-[(4-aminophenyl)sulfanylmethyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(CSC=2C=CC(N)=CC=2)=CC(N2[C@H](COCC2)C)=N1 FXEUPHFDPVLQLT-INIZCTEOSA-N 0.000 claims 1
WWASZSMYDFHBDD-INIZCTEOSA-N 1-[4-[4-[(4-aminophenyl)sulfonylmethyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(CS(=O)(=O)C=2C=CC(N)=CC=2)=CC(N2[C@H](COCC2)C)=N1 WWASZSMYDFHBDD-INIZCTEOSA-N 0.000 claims 1
OOYFVBRITDLKHP-SFHVURJKSA-N 1-[4-[4-[(4-chlorophenyl)sulfonylmethyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-cyclobutylurea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)C=2C=CC(Cl)=CC=2)=NC(C=2C=CC(NC(=O)NC3CCC3)=CC=2)=N1 OOYFVBRITDLKHP-SFHVURJKSA-N 0.000 claims 1
XJUBNWIHNZLQJH-KRWDZBQOSA-N 1-[4-[4-[(4-chlorophenyl)sulfonylmethyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(CS(=O)(=O)C=2C=CC(Cl)=CC=2)=CC(N2[C@H](COCC2)C)=N1 XJUBNWIHNZLQJH-KRWDZBQOSA-N 0.000 claims 1
YVGHSECCSUNERT-SFHVURJKSA-N 1-[4-[4-[(4-fluorophenyl)sulfonylmethyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-(1-hydroxy-2-methylpropan-2-yl)urea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)C=2C=CC(F)=CC=2)=NC(C=2C=CC(NC(=O)NC(C)(C)CO)=CC=2)=N1 YVGHSECCSUNERT-SFHVURJKSA-N 0.000 claims 1
SAYOKJPUAZEHEC-KRWDZBQOSA-N 1-[4-[4-[(4-fluorophenyl)sulfonylmethyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-(2-hydroxyethyl)urea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)C=2C=CC(F)=CC=2)=NC(C=2C=CC(NC(=O)NCCO)=CC=2)=N1 SAYOKJPUAZEHEC-KRWDZBQOSA-N 0.000 claims 1
HTBQVJZMCZPPJZ-IBGZPJMESA-N 1-[4-[4-[(4-fluorophenyl)sulfonylmethyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-(2-methylpropyl)urea Chemical compound C1=CC(NC(=O)NCC(C)C)=CC=C1C1=NC(CS(=O)(=O)C=2C=CC(F)=CC=2)=CC(N2[C@H](COCC2)C)=N1 HTBQVJZMCZPPJZ-IBGZPJMESA-N 0.000 claims 1
XJJDVKJGDUMXGO-IBGZPJMESA-N 1-[4-[4-[(4-fluorophenyl)sulfonylmethyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)C=2C=CC(F)=CC=2)=NC(C=2C=CC(NC(=O)NC=3C=CC(=CC=3)C(F)(F)F)=CC=2)=N1 XJJDVKJGDUMXGO-IBGZPJMESA-N 0.000 claims 1
QEVXCJDBFGCZQY-INIZCTEOSA-N 1-[4-[4-[(4-fluorophenyl)sulfonylmethyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(CS(=O)(=O)C=2C=CC(F)=CC=2)=CC(N2[C@H](COCC2)C)=N1 QEVXCJDBFGCZQY-INIZCTEOSA-N 0.000 claims 1
LJDYFYDICCNWRZ-SFHVURJKSA-N 1-[4-[4-[(4-fluorophenyl)sulfonylmethyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-propan-2-ylurea Chemical compound C1=CC(NC(=O)NC(C)C)=CC=C1C1=NC(CS(=O)(=O)C=2C=CC(F)=CC=2)=CC(N2[C@H](COCC2)C)=N1 LJDYFYDICCNWRZ-SFHVURJKSA-N 0.000 claims 1
MRYSDJONKLKQLF-SFHVURJKSA-N 1-[4-[4-[(4-fluorophenyl)sulfonylmethyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-propylurea Chemical compound C1=CC(NC(=O)NCCC)=CC=C1C1=NC(CS(=O)(=O)C=2C=CC(F)=CC=2)=CC(N2[C@H](COCC2)C)=N1 MRYSDJONKLKQLF-SFHVURJKSA-N 0.000 claims 1
HAZRMCHWJZOQHI-IBGZPJMESA-N 1-[4-[4-[(4-fluorophenyl)sulfonylmethyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-pyridin-2-ylurea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)C=2C=CC(F)=CC=2)=NC(C=2C=CC(NC(=O)NC=3N=CC=CC=3)=CC=2)=N1 HAZRMCHWJZOQHI-IBGZPJMESA-N 0.000 claims 1
RZMPDQDRXTZEQM-KRWDZBQOSA-N 1-[4-[4-[2-(3,5-difluorophenyl)sulfonylpropan-2-yl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-(2-hydroxyethyl)urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(=O)(=O)C=2C=C(F)C=C(F)C=2)=NC(C=2C=CC(NC(=O)NCCO)=CC=2)=N1 RZMPDQDRXTZEQM-KRWDZBQOSA-N 0.000 claims 1
GZQVULUIPHTYJU-IBGZPJMESA-N 1-[4-[4-[2-(3,5-difluorophenyl)sulfonylpropan-2-yl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-[2-(dimethylamino)ethyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(=O)(=O)C=2C=C(F)C=C(F)C=2)=NC(C=2C=CC(NC(=O)NCCN(C)C)=CC=2)=N1 GZQVULUIPHTYJU-IBGZPJMESA-N 0.000 claims 1
PKNOWYGVQGSHSZ-KRWDZBQOSA-N 1-[4-[4-[2-(3,5-difluorophenyl)sulfonylpropan-2-yl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-ethylurea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2[C@H](COCC2)C)=CC(C(C)(C)S(=O)(=O)C=2C=C(F)C=C(F)C=2)=N1 PKNOWYGVQGSHSZ-KRWDZBQOSA-N 0.000 claims 1
YTYYFEXVWRGXTB-INIZCTEOSA-N 1-[4-[4-[2-(3,5-difluorophenyl)sulfonylpropan-2-yl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2[C@H](COCC2)C)=CC(C(C)(C)S(=O)(=O)C=2C=C(F)C=C(F)C=2)=N1 YTYYFEXVWRGXTB-INIZCTEOSA-N 0.000 claims 1
UTKXJQSLGVIJQM-IBGZPJMESA-N 1-[4-[4-[2-(4-chlorophenyl)sulfonylpropan-2-yl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-cyclobutylurea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(=O)(=O)C=2C=CC(Cl)=CC=2)=NC(C=2C=CC(NC(=O)NC3CCC3)=CC=2)=N1 UTKXJQSLGVIJQM-IBGZPJMESA-N 0.000 claims 1
IKCYBTQIFRJYFR-SFHVURJKSA-N 1-[4-[4-[2-(4-chlorophenyl)sulfonylpropan-2-yl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-cyclopropylurea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(=O)(=O)C=2C=CC(Cl)=CC=2)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 IKCYBTQIFRJYFR-SFHVURJKSA-N 0.000 claims 1
SIGCJZKYRFORNZ-KRWDZBQOSA-N 1-[4-[4-[2-(4-chlorophenyl)sulfonylpropan-2-yl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2[C@H](COCC2)C)=CC(C(C)(C)S(=O)(=O)C=2C=CC(Cl)=CC=2)=N1 SIGCJZKYRFORNZ-KRWDZBQOSA-N 0.000 claims 1
WXYMKIUAKADOLJ-SFHVURJKSA-N 1-[4-[4-[2-(4-fluorophenyl)sulfonylpropan-2-yl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-(2-hydroxyethyl)urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(=O)(=O)C=2C=CC(F)=CC=2)=NC(C=2C=CC(NC(=O)NCCO)=CC=2)=N1 WXYMKIUAKADOLJ-SFHVURJKSA-N 0.000 claims 1
RDWJWTLGPWGQDD-KRWDZBQOSA-N 1-[4-[4-[2-(4-fluorophenyl)sulfonylpropan-2-yl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2[C@H](COCC2)C)=CC(C(C)(C)S(=O)(=O)C=2C=CC(F)=CC=2)=N1 RDWJWTLGPWGQDD-KRWDZBQOSA-N 0.000 claims 1
SIRSZROEJKQLSO-IBGZPJMESA-N 1-[4-[4-[2-(4-fluorophenyl)sulfonylpropan-2-yl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-propan-2-ylurea Chemical compound C1=CC(NC(=O)NC(C)C)=CC=C1C1=NC(N2[C@H](COCC2)C)=CC(C(C)(C)S(=O)(=O)C=2C=CC(F)=CC=2)=N1 SIRSZROEJKQLSO-IBGZPJMESA-N 0.000 claims 1
BLHQJCGRVAUEMK-SFHVURJKSA-N 1-[4-[4-[[cyclopropyl(methyl)amino]methyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-[(1-methylpyrazol-4-yl)methyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CN(C)C2CC2)=NC(C=2C=CC(NC(=O)NCC3=CN(C)N=C3)=CC=2)=N1 BLHQJCGRVAUEMK-SFHVURJKSA-N 0.000 claims 1
VPWHIDBKJNNFFL-ZDUSSCGKSA-N 1-[5-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]-1,3-thiazol-2-yl]-3-(1-methylpyrazol-4-yl)urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(C)(=O)=O)=NC(C=2SC(NC(=O)NC3=CN(C)N=C3)=NC=2)=N1 VPWHIDBKJNNFFL-ZDUSSCGKSA-N 0.000 claims 1
VTWALCCITCHLPT-AWEZNQCLSA-N 1-[5-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]-1,3-thiazol-2-yl]-3-[(1-methylpyrazol-4-yl)methyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(C)(=O)=O)=NC(C=2SC(NC(=O)NCC3=CN(C)N=C3)=NC=2)=N1 VTWALCCITCHLPT-AWEZNQCLSA-N 0.000 claims 1
DQVFEXNAIWXUCY-AWEZNQCLSA-N 1-[5-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]-1,3-thiazol-2-yl]-3-phenylurea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2SC(NC(=O)NC=3C=CC=CC=3)=NC=2)=N1 DQVFEXNAIWXUCY-AWEZNQCLSA-N 0.000 claims 1
KAMYLDCUXVVVKQ-LBPRGKRZSA-N 1-[5-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]-1,3-thiazol-2-yl]-3-propan-2-ylurea Chemical compound S1C(NC(=O)NC(C)C)=NC=C1C1=NC(CS(C)(=O)=O)=CC(N2[C@H](COCC2)C)=N1 KAMYLDCUXVVVKQ-LBPRGKRZSA-N 0.000 claims 1
XENSVNBCEPFONT-IBGZPJMESA-N 1-[[3-(dimethylamino)phenyl]methyl]-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=CC(NC(=O)NCC=3C=C(C=CC=3)N(C)C)=CC=2)=N1 XENSVNBCEPFONT-IBGZPJMESA-N 0.000 claims 1
QXUJTTCYAWVTPK-UHFFFAOYSA-N 1-benzyl-1-methyl-3-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound C=1C=C(C=2N=C(C=C(CS(C)(=O)=O)N=2)N2CCOCC2)C=CC=1NC(=O)N(C)CC1=CC=CC=C1 QXUJTTCYAWVTPK-UHFFFAOYSA-N 0.000 claims 1
KOHACNOEQVANFX-FQEVSTJZSA-N 1-cyclobutyl-3-[4-[4-(2-cyclohexylsulfonylpropan-2-yl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(=O)(=O)C2CCCCC2)=NC(C=2C=CC(NC(=O)NC3CCC3)=CC=2)=N1 KOHACNOEQVANFX-FQEVSTJZSA-N 0.000 claims 1
GTALWRZPYLCZND-IBGZPJMESA-N 1-cyclobutyl-3-[4-[4-(2-cyclopentylsulfonylpropan-2-yl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(=O)(=O)C2CCCC2)=NC(C=2C=CC(NC(=O)NC3CCC3)=CC=2)=N1 GTALWRZPYLCZND-IBGZPJMESA-N 0.000 claims 1
IYFCLJIWMFXSRO-KRWDZBQOSA-N 1-cyclobutyl-3-[4-[4-(2-cyclopropylsulfonylpropan-2-yl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(=O)(=O)C2CC2)=NC(C=2C=CC(NC(=O)NC3CCC3)=CC=2)=N1 IYFCLJIWMFXSRO-KRWDZBQOSA-N 0.000 claims 1
HYDRXVAQRWPYMG-KRWDZBQOSA-N 1-cyclobutyl-3-[4-[4-(2-ethylsulfonylpropan-2-yl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound N=1C(C(C)(C)S(=O)(=O)CC)=CC(N2[C@H](COCC2)C)=NC=1C(C=C1)=CC=C1NC(=O)NC1CCC1 HYDRXVAQRWPYMG-KRWDZBQOSA-N 0.000 claims 1
FBYTYPYYPIBDQO-INIZCTEOSA-N 1-cyclobutyl-3-[4-[4-(2-hydroxyethylsulfonylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)CCO)=NC(C=2C=CC(NC(=O)NC3CCC3)=CC=2)=N1 FBYTYPYYPIBDQO-INIZCTEOSA-N 0.000 claims 1
KBHNQJDDBKGNTR-SFHVURJKSA-N 1-cyclobutyl-3-[4-[4-(cyclopentylsulfonylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)C2CCCC2)=NC(C=2C=CC(NC(=O)NC3CCC3)=CC=2)=N1 KBHNQJDDBKGNTR-SFHVURJKSA-N 0.000 claims 1
VPKQKTMKSWGOMY-INIZCTEOSA-N 1-cyclobutyl-3-[4-[4-(cyclopropylsulfonylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)C2CC2)=NC(C=2C=CC(NC(=O)NC3CCC3)=CC=2)=N1 VPKQKTMKSWGOMY-INIZCTEOSA-N 0.000 claims 1
RTRRLWWUHBRYEW-INIZCTEOSA-N 1-cyclobutyl-3-[4-[4-(ethylsulfonylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound N=1C(CS(=O)(=O)CC)=CC(N2[C@H](COCC2)C)=NC=1C(C=C1)=CC=C1NC(=O)NC1CCC1 RTRRLWWUHBRYEW-INIZCTEOSA-N 0.000 claims 1
HSLFXCAUMUIALI-KRWDZBQOSA-N 1-cyclobutyl-3-[4-[4-[(3,5-difluorophenyl)sulfonylmethyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)C=2C=C(F)C=C(F)C=2)=NC(C=2C=CC(NC(=O)NC3CCC3)=CC=2)=N1 HSLFXCAUMUIALI-KRWDZBQOSA-N 0.000 claims 1
FUUIHDLZROEDHG-INIZCTEOSA-N 1-cyclobutyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(C)(=O)=O)=NC(C=2C=CC(NC(=O)NC3CCC3)=CC=2)=N1 FUUIHDLZROEDHG-INIZCTEOSA-N 0.000 claims 1
CRLCCTGVBZYDHD-SFHVURJKSA-N 1-cyclobutyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-propan-2-ylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]urea Chemical compound N=1C(C(C)(C)S(=O)(=O)C(C)C)=CC(N2[C@H](COCC2)C)=NC=1C(C=C1)=CC=C1NC(=O)NC1CCC1 CRLCCTGVBZYDHD-SFHVURJKSA-N 0.000 claims 1
RQGQYYRMWHCOMV-IBGZPJMESA-N 1-cyclobutyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-pyridin-4-ylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(=O)(=O)C=2C=CN=CC=2)=NC(C=2C=CC(NC(=O)NC3CCC3)=CC=2)=N1 RQGQYYRMWHCOMV-IBGZPJMESA-N 0.000 claims 1
VTSIRGKYOHTOJO-SFHVURJKSA-N 1-cyclobutyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(pyridin-4-ylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)C=2C=CN=CC=2)=NC(C=2C=CC(NC(=O)NC3CCC3)=CC=2)=N1 VTSIRGKYOHTOJO-SFHVURJKSA-N 0.000 claims 1
NGRWZPUPDWRMKW-SFHVURJKSA-N 1-cyclobutyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-[2-[(4-methyl-1,3-thiazol-2-yl)sulfonyl]propan-2-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(=O)(=O)C=2SC=C(C)N=2)=NC(C=2C=CC(NC(=O)NC3CCC3)=CC=2)=N1 NGRWZPUPDWRMKW-SFHVURJKSA-N 0.000 claims 1
PKKSPGDBZHLTPV-IBGZPJMESA-N 1-cyclobutyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-[2-[2-(trifluoromethyl)phenyl]sulfonylpropan-2-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=NC(C=2C=CC(NC(=O)NC3CCC3)=CC=2)=N1 PKKSPGDBZHLTPV-IBGZPJMESA-N 0.000 claims 1
IKOUYSVBCQDCDY-SFHVURJKSA-N 1-cyclobutyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-[[2-(trifluoromethyl)phenyl]sulfonylmethyl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=NC(C=2C=CC(NC(=O)NC3CCC3)=CC=2)=N1 IKOUYSVBCQDCDY-SFHVURJKSA-N 0.000 claims 1
WTKLIJFGVSVTKV-SFHVURJKSA-N 1-cyclobutyl-3-[4-[4-[2-(3,5-difluorophenyl)sulfonylpropan-2-yl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(=O)(=O)C=2C=C(F)C=C(F)C=2)=NC(C=2C=CC(NC(=O)NC3CCC3)=CC=2)=N1 WTKLIJFGVSVTKV-SFHVURJKSA-N 0.000 claims 1
RERAZGMJRHEMBR-IBGZPJMESA-N 1-cyclobutyl-3-[4-[4-[2-(4-fluorophenyl)sulfonylpropan-2-yl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(=O)(=O)C=2C=CC(F)=CC=2)=NC(C=2C=CC(NC(=O)NC3CCC3)=CC=2)=N1 RERAZGMJRHEMBR-IBGZPJMESA-N 0.000 claims 1
TXPMYCOWPMAODM-UHFFFAOYSA-N 1-cyclohexyl-3-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound N=1C(CS(=O)(=O)C)=CC(N2CCOCC2)=NC=1C(C=C1)=CC=C1NC(=O)NC1CCCCC1 TXPMYCOWPMAODM-UHFFFAOYSA-N 0.000 claims 1
JXOQUGKUFHFTKO-UHFFFAOYSA-N 1-cyclopropyl-1-methyl-3-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound C=1C=C(C=2N=C(C=C(CS(C)(=O)=O)N=2)N2CCOCC2)C=CC=1NC(=O)N(C)C1CC1 JXOQUGKUFHFTKO-UHFFFAOYSA-N 0.000 claims 1
QPAGANGGLCCHEF-INIZCTEOSA-N 1-cyclopropyl-1-methyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(C)(=O)=O)=NC(C=2C=CC(NC(=O)N(C)C3CC3)=CC=2)=N1 QPAGANGGLCCHEF-INIZCTEOSA-N 0.000 claims 1
JOYOSAPDHCTWLI-HNNXBMFYSA-N 1-cyclopropyl-1-methyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=CC(NC(=O)N(C)C3CC3)=CC=2)=N1 JOYOSAPDHCTWLI-HNNXBMFYSA-N 0.000 claims 1
CCTWESQATGGHCV-LBPRGKRZSA-N 1-cyclopropyl-1-methyl-3-[5-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]-1,3-thiazol-2-yl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2SC(NC(=O)N(C)C3CC3)=NC=2)=N1 CCTWESQATGGHCV-LBPRGKRZSA-N 0.000 claims 1
URVSRBDPPJSRIM-LBPRGKRZSA-N 1-cyclopropyl-3-[1-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]pyrazol-3-yl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(N2N=C(NC(=O)NC3CC3)C=C2)=N1 URVSRBDPPJSRIM-LBPRGKRZSA-N 0.000 claims 1
XNKJLUJTNIEWQJ-INIZCTEOSA-N 1-cyclopropyl-3-[4-[4-(1,1-dioxo-1,4-thiazinane-4-carbonyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(=O)N2CCS(=O)(=O)CC2)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 XNKJLUJTNIEWQJ-INIZCTEOSA-N 0.000 claims 1
TVCIHPUDBMAAPG-KRWDZBQOSA-N 1-cyclopropyl-3-[4-[4-(1,4-diazepane-1-carbonyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(=O)N2CCNCCC2)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 TVCIHPUDBMAAPG-KRWDZBQOSA-N 0.000 claims 1
HBONJRFACWYMAI-INIZCTEOSA-N 1-cyclopropyl-3-[4-[4-(2-cyclopropylsulfonylpropan-2-yl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(=O)(=O)C2CC2)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 HBONJRFACWYMAI-INIZCTEOSA-N 0.000 claims 1
ZDMNIZSTBPLZTQ-INIZCTEOSA-N 1-cyclopropyl-3-[4-[4-(2-ethylsulfonylpropan-2-yl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound N=1C(C(C)(C)S(=O)(=O)CC)=CC(N2[C@H](COCC2)C)=NC=1C(C=C1)=CC=C1NC(=O)NC1CC1 ZDMNIZSTBPLZTQ-INIZCTEOSA-N 0.000 claims 1
SNWZJCYMBOADSJ-HNNXBMFYSA-N 1-cyclopropyl-3-[4-[4-(2-hydroxyethylsulfonylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)CCO)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 SNWZJCYMBOADSJ-HNNXBMFYSA-N 0.000 claims 1
VSESEPMMBMBTHH-AWEZNQCLSA-N 1-cyclopropyl-3-[4-[4-(3-hydroxyazetidine-1-carbonyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(=O)N2CC(O)C2)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 VSESEPMMBMBTHH-AWEZNQCLSA-N 0.000 claims 1
VWTQCHFXRZTVBR-INIZCTEOSA-N 1-cyclopropyl-3-[4-[4-(3-hydroxypropylsulfanylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CSCCCO)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 VWTQCHFXRZTVBR-INIZCTEOSA-N 0.000 claims 1
FIIOZNQARSQIQQ-INIZCTEOSA-N 1-cyclopropyl-3-[4-[4-(3-hydroxypropylsulfonylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)CCCO)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 FIIOZNQARSQIQQ-INIZCTEOSA-N 0.000 claims 1
UQTNESYADLBWKW-INIZCTEOSA-N 1-cyclopropyl-3-[4-[4-(4-hydroxypiperidine-1-carbonyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(=O)N2CCC(O)CC2)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 UQTNESYADLBWKW-INIZCTEOSA-N 0.000 claims 1
AYGRQBVXVAGJRQ-HNNXBMFYSA-N 1-cyclopropyl-3-[4-[4-(cyclopropylsulfonylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)C2CC2)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 AYGRQBVXVAGJRQ-HNNXBMFYSA-N 0.000 claims 1
JWBCYZQJZVIZHK-ZDUSSCGKSA-N 1-cyclopropyl-3-[4-[4-(hydroxymethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CO)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 JWBCYZQJZVIZHK-ZDUSSCGKSA-N 0.000 claims 1
RAECGRQTUCDQSG-AWEZNQCLSA-N 1-cyclopropyl-3-[4-[4-(methoxymethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound N=1C(COC)=CC(N2[C@H](COCC2)C)=NC=1C(C=C1)=CC=C1NC(=O)NC1CC1 RAECGRQTUCDQSG-AWEZNQCLSA-N 0.000 claims 1
BMPIYLUKSQMBAN-UHFFFAOYSA-N 1-cyclopropyl-3-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound N=1C(CS(=O)(=O)C)=CC(N2CCOCC2)=NC=1C(C=C1)=CC=C1NC(=O)NC1CC1 BMPIYLUKSQMBAN-UHFFFAOYSA-N 0.000 claims 1
XBZSYENJVCXROM-KRWDZBQOSA-N 1-cyclopropyl-3-[4-[4-[(1,1-dioxo-1,4-thiazinan-4-yl)methyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CN2CCS(=O)(=O)CC2)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 XBZSYENJVCXROM-KRWDZBQOSA-N 0.000 claims 1
NDOIQLQEQMBYAA-INIZCTEOSA-N 1-cyclopropyl-3-[4-[4-[(2-methoxyethylamino)methyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound N=1C(CNCCOC)=CC(N2[C@H](COCC2)C)=NC=1C(C=C1)=CC=C1NC(=O)NC1CC1 NDOIQLQEQMBYAA-INIZCTEOSA-N 0.000 claims 1
FUGCJFTYMIPTJH-HNNXBMFYSA-N 1-cyclopropyl-3-[4-[4-[(3-hydroxyazetidin-1-yl)methyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CN2CC(O)C2)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 FUGCJFTYMIPTJH-HNNXBMFYSA-N 0.000 claims 1
HZKADGQNBWHOLZ-HNNXBMFYSA-N 1-cyclopropyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(1,3-thiazol-2-ylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)C=2SC=CN=2)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 HZKADGQNBWHOLZ-HNNXBMFYSA-N 0.000 claims 1
ITJZYMQJVMDMMV-HNNXBMFYSA-N 1-cyclopropyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(C)(=O)=O)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 ITJZYMQJVMDMMV-HNNXBMFYSA-N 0.000 claims 1
KBUOSLLTPHUHKH-KRWDZBQOSA-N 1-cyclopropyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-propan-2-ylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]urea Chemical compound N=1C(C(C)(C)S(=O)(=O)C(C)C)=CC(N2[C@H](COCC2)C)=NC=1C(C=C1)=CC=C1NC(=O)NC1CC1 KBUOSLLTPHUHKH-KRWDZBQOSA-N 0.000 claims 1
QRDMFBARIXAQPU-SFHVURJKSA-N 1-cyclopropyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-pyridin-4-ylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(=O)(=O)C=2C=CN=CC=2)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 QRDMFBARIXAQPU-SFHVURJKSA-N 0.000 claims 1
UOEYYNGBLJVDGA-KRWDZBQOSA-N 1-cyclopropyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(4-methylpiperazine-1-carbonyl)pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(=O)N2CCN(C)CC2)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 UOEYYNGBLJVDGA-KRWDZBQOSA-N 0.000 claims 1
PKPXFEDXJMVPGR-KRWDZBQOSA-N 1-cyclopropyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(morpholin-4-ylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CN2CCOCC2)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 PKPXFEDXJMVPGR-KRWDZBQOSA-N 0.000 claims 1
QOVYFIHVZIAIFE-INIZCTEOSA-N 1-cyclopropyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(morpholine-4-carbonyl)pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(=O)N2CCOCC2)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 QOVYFIHVZIAIFE-INIZCTEOSA-N 0.000 claims 1
RITAZOGFCCIYMA-INIZCTEOSA-N 1-cyclopropyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(propan-2-ylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound N=1C(CS(=O)(=O)C(C)C)=CC(N2[C@H](COCC2)C)=NC=1C(C=C1)=CC=C1NC(=O)NC1CC1 RITAZOGFCCIYMA-INIZCTEOSA-N 0.000 claims 1
KTNYPHOXTLEBCP-KRWDZBQOSA-N 1-cyclopropyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(pyridin-4-ylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)C=2C=CN=CC=2)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 KTNYPHOXTLEBCP-KRWDZBQOSA-N 0.000 claims 1
AKACSGMFIFPMJL-INIZCTEOSA-N 1-cyclopropyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-[(3-oxopiperazin-1-yl)methyl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CN2CC(=O)NCC2)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 AKACSGMFIFPMJL-INIZCTEOSA-N 0.000 claims 1
VAXRHHWOXYFWNE-INIZCTEOSA-N 1-cyclopropyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-[(4-methyl-1,3-thiazol-2-yl)sulfonylmethyl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)C=2SC=C(C)N=2)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 VAXRHHWOXYFWNE-INIZCTEOSA-N 0.000 claims 1
ALPCRNYBURTGBC-SFHVURJKSA-N 1-cyclopropyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-[(4-methylpiperazin-1-yl)methyl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CN2CCN(C)CC2)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 ALPCRNYBURTGBC-SFHVURJKSA-N 0.000 claims 1
AFIMKJOJTAWILA-AWEZNQCLSA-N 1-cyclopropyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfonylmethyl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)C=2SC(C)=NN=2)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 AFIMKJOJTAWILA-AWEZNQCLSA-N 0.000 claims 1
NIIOKOXWYBDDOW-KRWDZBQOSA-N 1-cyclopropyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-[2-[(4-methyl-1,3-thiazol-2-yl)sulfonyl]propan-2-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(=O)(=O)C=2SC=C(C)N=2)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 NIIOKOXWYBDDOW-KRWDZBQOSA-N 0.000 claims 1
UKBVEQTYSJMAGS-SFHVURJKSA-N 1-cyclopropyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-[2-[2-(trifluoromethyl)phenyl]sulfonylpropan-2-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 UKBVEQTYSJMAGS-SFHVURJKSA-N 0.000 claims 1
GERTUMHEUUYONF-ROUUACIJSA-N 1-cyclopropyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-[[(3s)-3-methylmorpholin-4-yl]methyl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1CC1=CC(N2[C@H](COCC2)C)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 GERTUMHEUUYONF-ROUUACIJSA-N 0.000 claims 1
CWGJYISESAKWED-KRWDZBQOSA-N 1-cyclopropyl-3-[4-[4-[(4-fluorophenyl)sulfonylmethyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)C=2C=CC(F)=CC=2)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 CWGJYISESAKWED-KRWDZBQOSA-N 0.000 claims 1
WWHMALYSYJFMNK-IBGZPJMESA-N 1-cyclopropyl-3-[4-[4-[(4-methyl-1,4-diazepan-1-yl)methyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CN2CCN(C)CCC2)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 WWHMALYSYJFMNK-IBGZPJMESA-N 0.000 claims 1
VUNRCAOCHUQRQO-HNNXBMFYSA-N 1-cyclopropyl-3-[4-[4-[(cyclopropylamino)methyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CNC2CC2)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 VUNRCAOCHUQRQO-HNNXBMFYSA-N 0.000 claims 1
CSMQFGBZSPDMDK-HNNXBMFYSA-N 1-cyclopropyl-3-[4-[4-[(dimethylamino)methyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CN(C)C)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 CSMQFGBZSPDMDK-HNNXBMFYSA-N 0.000 claims 1
GFJFYKMSMZHPCD-INIZCTEOSA-N 1-cyclopropyl-3-[4-[4-[[(1-hydroxy-2-methylpropan-2-yl)amino]methyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CNC(C)(C)CO)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 GFJFYKMSMZHPCD-INIZCTEOSA-N 0.000 claims 1
XMHOKUDSKVOASQ-KRWDZBQOSA-N 1-cyclopropyl-3-[4-[4-[[2-(dimethylamino)ethylamino]methyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CNCCN(C)C)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 XMHOKUDSKVOASQ-KRWDZBQOSA-N 0.000 claims 1
FDPDGBJNEJLPDY-INIZCTEOSA-N 1-cyclopropyl-3-[4-[4-[[2-hydroxyethyl(methyl)amino]methyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CN(C)CCO)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 FDPDGBJNEJLPDY-INIZCTEOSA-N 0.000 claims 1
NOSMBJFRAKKGAE-SFHVURJKSA-N 1-cyclopropyl-3-[4-[4-[[3-(dimethylamino)propylamino]methyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CNCCCN(C)C)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 NOSMBJFRAKKGAE-SFHVURJKSA-N 0.000 claims 1
QZDBMHJQSOKCGK-LBPRGKRZSA-N 1-cyclopropyl-3-[5-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]-1,3-thiazol-2-yl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(C)(=O)=O)=NC(C=2SC(NC(=O)NC3CC3)=NC=2)=N1 QZDBMHJQSOKCGK-LBPRGKRZSA-N 0.000 claims 1
PUIFIMUWUNBMMC-AWEZNQCLSA-N 1-cyclopropyl-3-[5-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]pyridin-2-yl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(C)(=O)=O)=NC(C=2C=NC(NC(=O)NC3CC3)=CC=2)=N1 PUIFIMUWUNBMMC-AWEZNQCLSA-N 0.000 claims 1
HNHHSPVPWXDZBU-ZDUSSCGKSA-N 1-cyclopropyl-3-[5-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]pyrimidin-2-yl]urea Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(C)(=O)=O)=NC(C=2C=NC(NC(=O)NC3CC3)=NC=2)=N1 HNHHSPVPWXDZBU-ZDUSSCGKSA-N 0.000 claims 1
CGNYDMZHBUUANW-NSHDSACASA-N 1-cyclopropyl-3-[5-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]-1,3-thiazol-2-yl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2SC(NC(=O)NC3CC3)=NC=2)=N1 CGNYDMZHBUUANW-NSHDSACASA-N 0.000 claims 1
ASDRPTKGJOVRKV-UHFFFAOYSA-N 1-ethyl-1-methyl-3-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)N(C)CC)=CC=C1C1=NC(CS(C)(=O)=O)=CC(N2CCOCC2)=N1 ASDRPTKGJOVRKV-UHFFFAOYSA-N 0.000 claims 1
WCNCMRTWCLGGEE-LBPRGKRZSA-N 1-ethyl-3-[1-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]pyrazol-3-yl]urea Chemical compound N1=C(NC(=O)NCC)C=CN1C1=NC(CS(C)(=O)=O)=CC(N2[C@H](COCC2)C)=N1 WCNCMRTWCLGGEE-LBPRGKRZSA-N 0.000 claims 1
YXCLMGAZZPERMR-ZDUSSCGKSA-N 1-ethyl-3-[2-fluoro-4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C1=C(F)C(NC(=O)NCC)=CC=C1C1=NC(CS(C)(=O)=O)=CC(N2[C@H](COCC2)C)=N1 YXCLMGAZZPERMR-ZDUSSCGKSA-N 0.000 claims 1
AXIHIOMZTUDMBR-AWEZNQCLSA-N 1-ethyl-3-[2-methoxy-4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C1=C(OC)C(NC(=O)NCC)=CC=C1C1=NC(CS(C)(=O)=O)=CC(N2[C@H](COCC2)C)=N1 AXIHIOMZTUDMBR-AWEZNQCLSA-N 0.000 claims 1
PEVKZKXVMZRMGM-INIZCTEOSA-N 1-ethyl-3-[4-[4-(2-ethylsulfonylpropan-2-yl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2[C@H](COCC2)C)=CC(C(C)(C)S(=O)(=O)CC)=N1 PEVKZKXVMZRMGM-INIZCTEOSA-N 0.000 claims 1
ICMVVYJNGREKBY-HNNXBMFYSA-N 1-ethyl-3-[4-[4-(2-hydroxyethylsulfonylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(CS(=O)(=O)CCO)=CC(N2[C@H](COCC2)C)=N1 ICMVVYJNGREKBY-HNNXBMFYSA-N 0.000 claims 1
BBPSBTHTHLMROY-UHFFFAOYSA-N 1-ethyl-3-[4-[4-(2-methylsulfonylpropan-2-yl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2CCOCC2)=CC(C(C)(C)S(C)(=O)=O)=N1 BBPSBTHTHLMROY-UHFFFAOYSA-N 0.000 claims 1
HJPQRLSLSSGXPG-HNNXBMFYSA-N 1-ethyl-3-[4-[4-(ethylsulfonylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(CS(=O)(=O)CC)=CC(N2[C@H](COCC2)C)=N1 HJPQRLSLSSGXPG-HNNXBMFYSA-N 0.000 claims 1
JRLOMEIGZPGLFJ-ZDUSSCGKSA-N 1-ethyl-3-[4-[4-(hydroxymethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(CO)=CC(N2[C@H](COCC2)C)=N1 JRLOMEIGZPGLFJ-ZDUSSCGKSA-N 0.000 claims 1
SQABLTLUVYXNAO-UHFFFAOYSA-N 1-ethyl-3-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(CS(C)(=O)=O)=CC(N2CCOCC2)=N1 SQABLTLUVYXNAO-UHFFFAOYSA-N 0.000 claims 1
MCTATMFKFBEJOT-HNNXBMFYSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2[C@H](COCC2)C)=CC(C(C)(C)S(C)(=O)=O)=N1 MCTATMFKFBEJOT-HNNXBMFYSA-N 0.000 claims 1
PBXYAVBJRSHVSR-KRWDZBQOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-propan-2-ylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2[C@H](COCC2)C)=CC(C(C)(C)S(=O)(=O)C(C)C)=N1 PBXYAVBJRSHVSR-KRWDZBQOSA-N 0.000 claims 1
HUOPHADFEZILBZ-SFHVURJKSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-pyridin-2-ylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2[C@H](COCC2)C)=CC(C(C)(C)S(=O)(=O)C=2N=CC=CC=2)=N1 HUOPHADFEZILBZ-SFHVURJKSA-N 0.000 claims 1
DVQJAIOBMGYWCL-AWEZNQCLSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(CS(C)(=O)=O)=CC(N2[C@H](COCC2)C)=N1 DVQJAIOBMGYWCL-AWEZNQCLSA-N 0.000 claims 1
ZGTXPVQCQUHFBE-INIZCTEOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(propan-2-ylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(CS(=O)(=O)C(C)C)=CC(N2[C@H](COCC2)C)=N1 ZGTXPVQCQUHFBE-INIZCTEOSA-N 0.000 claims 1
WQVYQGWXERZUDM-KRWDZBQOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(pyridin-2-ylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(CS(=O)(=O)C=2N=CC=CC=2)=CC(N2[C@H](COCC2)C)=N1 WQVYQGWXERZUDM-KRWDZBQOSA-N 0.000 claims 1
BGRYVYHBGWDYBX-KRWDZBQOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(pyridin-4-ylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(CS(=O)(=O)C=2C=CN=CC=2)=CC(N2[C@H](COCC2)C)=N1 BGRYVYHBGWDYBX-KRWDZBQOSA-N 0.000 claims 1
APKBOZLRVBRBFW-INIZCTEOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-[(4-methyl-1,3-thiazol-2-yl)sulfonylmethyl]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(CS(=O)(=O)C=2SC=C(C)N=2)=CC(N2[C@H](COCC2)C)=N1 APKBOZLRVBRBFW-INIZCTEOSA-N 0.000 claims 1
DRYBSOIOUXWAII-KRWDZBQOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-[2-[(4-methyl-1,3-thiazol-2-yl)sulfonyl]propan-2-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(N2[C@H](COCC2)C)=CC(C(C)(C)S(=O)(=O)C=2SC=C(C)N=2)=N1 DRYBSOIOUXWAII-KRWDZBQOSA-N 0.000 claims 1
DQCZEAPXLFLKIE-KRWDZBQOSA-N 1-ethyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-[[2-(trifluoromethyl)phenyl]sulfonylmethyl]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(CS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=CC(N2[C@H](COCC2)C)=N1 DQCZEAPXLFLKIE-KRWDZBQOSA-N 0.000 claims 1
DFABPPJQGRMANX-KRWDZBQOSA-N 1-ethyl-3-[4-[4-[(4-fluorophenyl)sulfonylmethyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(CS(=O)(=O)C=2C=CC(F)=CC=2)=CC(N2[C@H](COCC2)C)=N1 DFABPPJQGRMANX-KRWDZBQOSA-N 0.000 claims 1
OBCFRDDJWDKIBT-UHFFFAOYSA-N 1-ethyl-3-[4-[4-morpholin-4-yl-6-(propan-2-ylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1C1=NC(CS(=O)(=O)C(C)C)=CC(N2CCOCC2)=N1 OBCFRDDJWDKIBT-UHFFFAOYSA-N 0.000 claims 1
XHNRCLWTDFKTKY-LBPRGKRZSA-N 1-ethyl-3-[5-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]-1,3-thiazol-2-yl]urea Chemical compound S1C(NC(=O)NCC)=NC=C1C1=NC(N2[C@H](COCC2)C)=CC(C(C)(C)S(C)(=O)=O)=N1 XHNRCLWTDFKTKY-LBPRGKRZSA-N 0.000 claims 1
TYHBMOJLPHJVDT-AWEZNQCLSA-N 1-ethyl-3-[5-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]pyridin-2-yl]urea Chemical compound C1=NC(NC(=O)NCC)=CC=C1C1=NC(N2[C@H](COCC2)C)=CC(C(C)(C)S(C)(=O)=O)=N1 TYHBMOJLPHJVDT-AWEZNQCLSA-N 0.000 claims 1
VQKLDSLECFHQLM-ZDUSSCGKSA-N 1-ethyl-3-[5-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]pyrimidin-2-yl]urea Chemical compound C1=NC(NC(=O)NCC)=NC=C1C1=NC(N2[C@H](COCC2)C)=CC(C(C)(C)S(C)(=O)=O)=N1 VQKLDSLECFHQLM-ZDUSSCGKSA-N 0.000 claims 1
QFQIZZUVOVPSMD-NSHDSACASA-N 1-ethyl-3-[5-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]-1,3-thiazol-2-yl]urea Chemical compound S1C(NC(=O)NCC)=NC=C1C1=NC(CS(C)(=O)=O)=CC(N2[C@H](COCC2)C)=N1 QFQIZZUVOVPSMD-NSHDSACASA-N 0.000 claims 1
YUNWRANQZPCJQU-ZDUSSCGKSA-N 1-ethyl-3-[5-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]pyridin-2-yl]urea Chemical compound C1=NC(NC(=O)NCC)=CC=C1C1=NC(CS(C)(=O)=O)=CC(N2[C@H](COCC2)C)=N1 YUNWRANQZPCJQU-ZDUSSCGKSA-N 0.000 claims 1
ROXZCPFKIUPOIP-UHFFFAOYSA-N 1-methyl-1-(2-methylsulfonylethyl)-3-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)N(CCS(C)(=O)=O)C)=CC=C1C1=NC(CS(C)(=O)=O)=CC(N2CCOCC2)=N1 ROXZCPFKIUPOIP-UHFFFAOYSA-N 0.000 claims 1
LICZXRORFSZSQH-AWEZNQCLSA-N 1-methyl-3-[1-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]piperidin-4-yl]urea Chemical compound C1CC(NC(=O)NC)CCN1C1=NC(N2[C@H](COCC2)C)=CC(C(C)(C)S(C)(=O)=O)=N1 LICZXRORFSZSQH-AWEZNQCLSA-N 0.000 claims 1
SEEIAKBWZIWKBN-ZDUSSCGKSA-N 1-methyl-3-[1-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]piperidin-4-yl]urea Chemical compound C1CC(NC(=O)NC)CCN1C1=NC(CS(C)(=O)=O)=CC(N2[C@H](COCC2)C)=N1 SEEIAKBWZIWKBN-ZDUSSCGKSA-N 0.000 claims 1
GFJICTSLZNQMPU-NSHDSACASA-N 1-methyl-3-[1-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]pyrazol-3-yl]urea Chemical compound N1=C(NC(=O)NC)C=CN1C1=NC(CS(C)(=O)=O)=CC(N2[C@H](COCC2)C)=N1 GFJICTSLZNQMPU-NSHDSACASA-N 0.000 claims 1
KQRQMDJKCCLVFL-AWEZNQCLSA-N 1-methyl-3-[2-methyl-4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C1=C(C)C(NC(=O)NC)=CC=C1C1=NC(CS(C)(=O)=O)=CC(N2[C@H](COCC2)C)=N1 KQRQMDJKCCLVFL-AWEZNQCLSA-N 0.000 claims 1
JTOXMDFPNSMUIM-UHFFFAOYSA-N 1-methyl-3-[4-[4-(2-methylsulfonylpropan-2-yl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2CCOCC2)=CC(C(C)(C)S(C)(=O)=O)=N1 JTOXMDFPNSMUIM-UHFFFAOYSA-N 0.000 claims 1
HKYDSBSWAFZNNP-HNNXBMFYSA-N 1-methyl-3-[4-[4-[(1-methylimidazol-2-yl)sulfanylmethyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(CSC=2N(C=CN=2)C)=CC(N2[C@H](COCC2)C)=N1 HKYDSBSWAFZNNP-HNNXBMFYSA-N 0.000 claims 1
OWRUBEUDCVTADW-HNNXBMFYSA-N 1-methyl-3-[4-[4-[(1-methylimidazol-2-yl)sulfonylmethyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(CS(=O)(=O)C=2N(C=CN=2)C)=CC(N2[C@H](COCC2)C)=N1 OWRUBEUDCVTADW-HNNXBMFYSA-N 0.000 claims 1
NJDFQXJAPUEAHI-AWEZNQCLSA-N 1-methyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(1,3-thiazol-2-ylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(CS(=O)(=O)C=2SC=CN=2)=CC(N2[C@H](COCC2)C)=N1 NJDFQXJAPUEAHI-AWEZNQCLSA-N 0.000 claims 1
SOUXVVSBNVPUSB-AWEZNQCLSA-N 1-methyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2[C@H](COCC2)C)=CC(C(C)(C)S(C)(=O)=O)=N1 SOUXVVSBNVPUSB-AWEZNQCLSA-N 0.000 claims 1
RHFHNWVOBWTHNM-INIZCTEOSA-N 1-methyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-propan-2-ylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2[C@H](COCC2)C)=CC(C(C)(C)S(=O)(=O)C(C)C)=N1 RHFHNWVOBWTHNM-INIZCTEOSA-N 0.000 claims 1
URZRKZCBEBANOP-KRWDZBQOSA-N 1-methyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-pyridin-4-ylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2[C@H](COCC2)C)=CC(C(C)(C)S(=O)(=O)C=2C=CN=CC=2)=N1 URZRKZCBEBANOP-KRWDZBQOSA-N 0.000 claims 1
KMMVPPLBFHKLLS-ZDUSSCGKSA-N 1-methyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(CS(C)(=O)=O)=CC(N2[C@H](COCC2)C)=N1 KMMVPPLBFHKLLS-ZDUSSCGKSA-N 0.000 claims 1
JPRAUKIASIIQPN-HNNXBMFYSA-N 1-methyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(propan-2-ylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(CS(=O)(=O)C(C)C)=CC(N2[C@H](COCC2)C)=N1 JPRAUKIASIIQPN-HNNXBMFYSA-N 0.000 claims 1
JZEGINVEPGSNDL-INIZCTEOSA-N 1-methyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(pyridin-2-ylsulfanylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(CSC=2N=CC=CC=2)=CC(N2[C@H](COCC2)C)=N1 JZEGINVEPGSNDL-INIZCTEOSA-N 0.000 claims 1
WSMAJHCJKZZCAS-INIZCTEOSA-N 1-methyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(pyridin-2-ylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(CS(=O)(=O)C=2N=CC=CC=2)=CC(N2[C@H](COCC2)C)=N1 WSMAJHCJKZZCAS-INIZCTEOSA-N 0.000 claims 1
UDYWNZWJAWCVSM-INIZCTEOSA-N 1-methyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(pyridin-4-ylsulfanylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(CSC=2C=CN=CC=2)=CC(N2[C@H](COCC2)C)=N1 UDYWNZWJAWCVSM-INIZCTEOSA-N 0.000 claims 1
BYDVLIHZUFMNNC-INIZCTEOSA-N 1-methyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(pyridin-4-ylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(CS(=O)(=O)C=2C=CN=CC=2)=CC(N2[C@H](COCC2)C)=N1 BYDVLIHZUFMNNC-INIZCTEOSA-N 0.000 claims 1
MGLWIFSTOMQOIC-SFHVURJKSA-N 1-methyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-[(2-methylphenyl)sulfanylmethyl]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(CSC=2C(=CC=CC=2)C)=CC(N2[C@H](COCC2)C)=N1 MGLWIFSTOMQOIC-SFHVURJKSA-N 0.000 claims 1
AVAZYMAEAQBQHU-SFHVURJKSA-N 1-methyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-[(2-methylphenyl)sulfonylmethyl]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(CS(=O)(=O)C=2C(=CC=CC=2)C)=CC(N2[C@H](COCC2)C)=N1 AVAZYMAEAQBQHU-SFHVURJKSA-N 0.000 claims 1
KAJGYJPBWBXTHB-HNNXBMFYSA-N 1-methyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-[(4-methyl-1,3-thiazol-2-yl)sulfanylmethyl]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(CSC=2SC=C(C)N=2)=CC(N2[C@H](COCC2)C)=N1 KAJGYJPBWBXTHB-HNNXBMFYSA-N 0.000 claims 1
WGGKYXNLZMVVMX-HNNXBMFYSA-N 1-methyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-[(4-methyl-1,3-thiazol-2-yl)sulfonylmethyl]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(CS(=O)(=O)C=2SC=C(C)N=2)=CC(N2[C@H](COCC2)C)=N1 WGGKYXNLZMVVMX-HNNXBMFYSA-N 0.000 claims 1
OOKYVFKQIWSPQW-INIZCTEOSA-N 1-methyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-[2-[(4-methyl-1,3-thiazol-2-yl)sulfonyl]propan-2-yl]pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(N2[C@H](COCC2)C)=CC(C(C)(C)S(=O)(=O)C=2SC=C(C)N=2)=N1 OOKYVFKQIWSPQW-INIZCTEOSA-N 0.000 claims 1
QFTLOOMYWKSBGO-UHFFFAOYSA-N 1-methyl-3-[4-[4-morpholin-4-yl-6-(propan-2-ylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(CS(=O)(=O)C(C)C)=CC(N2CCOCC2)=N1 QFTLOOMYWKSBGO-UHFFFAOYSA-N 0.000 claims 1
YLURRARMCWJSCF-NSHDSACASA-N 1-methyl-3-[5-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]-1,3-thiazol-2-yl]urea Chemical compound S1C(NC(=O)NC)=NC=C1C1=NC(N2[C@H](COCC2)C)=CC(C(C)(C)S(C)(=O)=O)=N1 YLURRARMCWJSCF-NSHDSACASA-N 0.000 claims 1
NJHAXWFYGIUFFQ-ZDUSSCGKSA-N 1-methyl-3-[5-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]pyridin-2-yl]urea Chemical compound C1=NC(NC(=O)NC)=CC=C1C1=NC(N2[C@H](COCC2)C)=CC(C(C)(C)S(C)(=O)=O)=N1 NJHAXWFYGIUFFQ-ZDUSSCGKSA-N 0.000 claims 1
PYGRFJFJYJVRKR-LBPRGKRZSA-N 1-methyl-3-[5-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]pyrimidin-2-yl]urea Chemical compound C1=NC(NC(=O)NC)=NC=C1C1=NC(N2[C@H](COCC2)C)=CC(C(C)(C)S(C)(=O)=O)=N1 PYGRFJFJYJVRKR-LBPRGKRZSA-N 0.000 claims 1
BIPMYQOLMGRLEJ-JTQLQIEISA-N 1-methyl-3-[5-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]-1,3-thiazol-2-yl]urea Chemical compound S1C(NC(=O)NC)=NC=C1C1=NC(CS(C)(=O)=O)=CC(N2[C@H](COCC2)C)=N1 BIPMYQOLMGRLEJ-JTQLQIEISA-N 0.000 claims 1
JLXCZJBZKGQDMU-UHFFFAOYSA-N 1-tert-butyl-3-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NC(C)(C)C)=CC=C1C1=NC(CS(C)(=O)=O)=CC(N2CCOCC2)=N1 JLXCZJBZKGQDMU-UHFFFAOYSA-N 0.000 claims 1
HKQSTSJEFXRKFX-HNNXBMFYSA-N 1-tert-butyl-3-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]urea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=CC(NC(=O)NC(C)(C)C)=CC=2)=N1 HKQSTSJEFXRKFX-HNNXBMFYSA-N 0.000 claims 1
DXPVFXOACKTCNI-AWEZNQCLSA-N 2-[4-(cyclopropylcarbamoylamino)phenyl]-n,n-dimethyl-6-[(3s)-3-methylmorpholin-4-yl]pyrimidine-4-carboxamide Chemical compound C[C@H]1COCCN1C1=CC(C(=O)N(C)C)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 DXPVFXOACKTCNI-AWEZNQCLSA-N 0.000 claims 1
PQUMTHLIHKREFI-HNNXBMFYSA-N 2-[4-(cyclopropylcarbamoylamino)phenyl]-n-(2-hydroxyethyl)-n-methyl-6-[(3s)-3-methylmorpholin-4-yl]pyrimidine-4-carboxamide Chemical compound C[C@H]1COCCN1C1=CC(C(=O)N(C)CCO)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 PQUMTHLIHKREFI-HNNXBMFYSA-N 0.000 claims 1
OWGYJDICMIPGTF-HNNXBMFYSA-N 2-[4-(cyclopropylcarbamoylamino)phenyl]-n-(2-methoxyethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidine-4-carboxamide Chemical compound N=1C(C(=O)NCCOC)=CC(N2[C@H](COCC2)C)=NC=1C(C=C1)=CC=C1NC(=O)NC1CC1 OWGYJDICMIPGTF-HNNXBMFYSA-N 0.000 claims 1
JTHLLRFZNBHGEN-INIZCTEOSA-N 2-[4-(cyclopropylcarbamoylamino)phenyl]-n-(2-methoxyethyl)-n-methyl-6-[(3s)-3-methylmorpholin-4-yl]pyrimidine-4-carboxamide Chemical compound N=1C(C(=O)N(C)CCOC)=CC(N2[C@H](COCC2)C)=NC=1C(C=C1)=CC=C1NC(=O)NC1CC1 JTHLLRFZNBHGEN-INIZCTEOSA-N 0.000 claims 1
VHBZXBDDBPPHHP-INIZCTEOSA-N 2-[4-(cyclopropylcarbamoylamino)phenyl]-n-(cyclopropylmethyl)-n-methyl-6-[(3s)-3-methylmorpholin-4-yl]pyrimidine-4-carboxamide Chemical compound C[C@H]1COCCN1C1=CC(C(=O)N(C)CC2CC2)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 VHBZXBDDBPPHHP-INIZCTEOSA-N 0.000 claims 1
PKNWCMDATQMAJR-INIZCTEOSA-N 2-[4-(cyclopropylcarbamoylamino)phenyl]-n-[(3-methylimidazol-4-yl)methyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidine-4-carboxamide Chemical compound C[C@H]1COCCN1C1=CC(C(=O)NCC=2N(C=NC=2)C)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 PKNWCMDATQMAJR-INIZCTEOSA-N 0.000 claims 1
DLVOADDUGLYXCD-AWEZNQCLSA-N 2-[4-(cyclopropylcarbamoylamino)phenyl]-n-ethyl-6-[(3s)-3-methylmorpholin-4-yl]pyrimidine-4-carboxamide Chemical compound N=1C(C(=O)NCC)=CC(N2[C@H](COCC2)C)=NC=1C(C=C1)=CC=C1NC(=O)NC1CC1 DLVOADDUGLYXCD-AWEZNQCLSA-N 0.000 claims 1
HGQZXFJDZYEKAM-HNNXBMFYSA-N 2-[[2-[4-(cyclopropylcarbamoylamino)phenyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-4-yl]methylsulfonyl]-n-methylacetamide Chemical compound N=1C(CS(=O)(=O)CC(=O)NC)=CC(N2[C@H](COCC2)C)=NC=1C(C=C1)=CC=C1NC(=O)NC1CC1 HGQZXFJDZYEKAM-HNNXBMFYSA-N 0.000 claims 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
ZDULHUHNYHJYKA-UHFFFAOYSA-N 2-propan-2-ylsulfonylpropane Chemical compound CC(C)S(=O)(=O)C(C)C ZDULHUHNYHJYKA-UHFFFAOYSA-N 0.000 claims 1
OUIMQXBBSKFEGF-ZDUSSCGKSA-N 3-[2-fluoro-4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]-1,1-dimethylurea Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=C(F)C(NC(=O)N(C)C)=CC=2)=N1 OUIMQXBBSKFEGF-ZDUSSCGKSA-N 0.000 claims 1
UBELLOHJEVWXDI-HNNXBMFYSA-N 3-[2-fluoro-4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]-1-(2-methoxyethyl)-1-methylurea Chemical compound C1=C(F)C(NC(=O)N(C)CCOC)=CC=C1C1=NC(CS(C)(=O)=O)=CC(N2[C@H](COCC2)C)=N1 UBELLOHJEVWXDI-HNNXBMFYSA-N 0.000 claims 1
RWYYWEWJXXIULB-AWEZNQCLSA-N 3-[2-methoxy-4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]-1,1-dimethylurea Chemical compound C1=C(NC(=O)N(C)C)C(OC)=CC(C=2N=C(C=C(CS(C)(=O)=O)N=2)N2[C@H](COCC2)C)=C1 RWYYWEWJXXIULB-AWEZNQCLSA-N 0.000 claims 1
RORFNJNLKMBNGV-SFHVURJKSA-N 3-[4-[4-(benzenesulfonylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-1,1-dimethylurea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)C=2C=CC=CC=2)=NC(C=2C=CC(NC(=O)N(C)C)=CC=2)=N1 RORFNJNLKMBNGV-SFHVURJKSA-N 0.000 claims 1
IQNMVKKSLCIFGC-HNNXBMFYSA-N 3-[4-[4-(cyanomethylsulfonylmethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-1,1-dimethylurea Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)CC#N)=NC(C=2C=CC(NC(=O)N(C)C)=CC=2)=N1 IQNMVKKSLCIFGC-HNNXBMFYSA-N 0.000 claims 1
MZEUKOHDDSHQOP-ZDUSSCGKSA-N 3-[4-[4-(hydroxymethyl)-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-1,1-dimethylurea Chemical compound C[C@H]1COCCN1C1=CC(CO)=NC(C=2C=CC(NC(=O)N(C)C)=CC=2)=N1 MZEUKOHDDSHQOP-ZDUSSCGKSA-N 0.000 claims 1
OASLHVJTSQOOIF-INIZCTEOSA-N 4-methyl-n-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]-3-oxopiperazine-1-carboxamide Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=CC(NC(=O)N3CC(=O)N(C)CC3)=CC=2)=N1 OASLHVJTSQOOIF-INIZCTEOSA-N 0.000 claims 1
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
ZPXIXVRAJGCVLR-UHFFFAOYSA-N [4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]urea Chemical compound N=1C(CS(=O)(=O)C)=CC(N2CCOCC2)=NC=1C1=CC=C(NC(N)=O)C=C1 ZPXIXVRAJGCVLR-UHFFFAOYSA-N 0.000 claims 1
METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims 1
PVXOUGHWLCBJOW-UHFFFAOYSA-N azetidine-1-carboxamide Chemical compound NC(=O)N1CCC1 PVXOUGHWLCBJOW-UHFFFAOYSA-N 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims 1
ZKWFSTHEYLJLEL-UHFFFAOYSA-N morpholine-4-carboxamide Chemical compound NC(=O)N1CCOCC1 ZKWFSTHEYLJLEL-UHFFFAOYSA-N 0.000 claims 1
LXYXTVVFNNTNAV-INIZCTEOSA-N n-[2-[[2-[4-(cyclopropylcarbamoylamino)phenyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-4-yl]methylsulfonyl]ethyl]acetamide Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)CCNC(C)=O)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 LXYXTVVFNNTNAV-INIZCTEOSA-N 0.000 claims 1
VQGAMPPPFJYJEO-INIZCTEOSA-N n-[2-[[2-[4-(dimethylcarbamoylamino)phenyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-4-yl]methylsulfonyl]ethyl]acetamide Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)CCNC(C)=O)=NC(C=2C=CC(NC(=O)N(C)C)=CC=2)=N1 VQGAMPPPFJYJEO-INIZCTEOSA-N 0.000 claims 1
MOCKHYVHACIMOX-UHFFFAOYSA-N n-[2-[[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]carbamoylamino]ethyl]acetamide Chemical compound C1=CC(NC(=O)NCCNC(=O)C)=CC=C1C1=NC(CS(C)(=O)=O)=CC(N2CCOCC2)=N1 MOCKHYVHACIMOX-UHFFFAOYSA-N 0.000 claims 1
PGGKVWYTJAQGRY-INIZCTEOSA-N n-[2-[[6-[(3s)-3-methylmorpholin-4-yl]-2-[4-(1,2-oxazol-3-ylcarbamoylamino)phenyl]pyrimidin-4-yl]methylsulfonyl]ethyl]acetamide Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)CCNC(C)=O)=NC(C=2C=CC(NC(=O)NC3=NOC=C3)=CC=2)=N1 PGGKVWYTJAQGRY-INIZCTEOSA-N 0.000 claims 1
YTEMMVSQGGWIAQ-IBGZPJMESA-N n-[2-[[6-[(3s)-3-methylmorpholin-4-yl]-2-[4-(phenylcarbamoylamino)phenyl]pyrimidin-4-yl]methylsulfonyl]ethyl]acetamide Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)CCNC(C)=O)=NC(C=2C=CC(NC(=O)NC=3C=CC=CC=3)=CC=2)=N1 YTEMMVSQGGWIAQ-IBGZPJMESA-N 0.000 claims 1
ZJYHVLRWZPNDFE-SFHVURJKSA-N n-[2-[[6-[(3s)-3-methylmorpholin-4-yl]-2-[4-[(1-methylpyrazol-4-yl)methylcarbamoylamino]phenyl]pyrimidin-4-yl]methylsulfanyl]ethyl]acetamide Chemical compound C[C@H]1COCCN1C1=CC(CSCCNC(C)=O)=NC(C=2C=CC(NC(=O)NCC3=CN(C)N=C3)=CC=2)=N1 ZJYHVLRWZPNDFE-SFHVURJKSA-N 0.000 claims 1
JGWGVLQFWFRBDG-SFHVURJKSA-N n-[2-[[6-[(3s)-3-methylmorpholin-4-yl]-2-[4-[(1-methylpyrazol-4-yl)methylcarbamoylamino]phenyl]pyrimidin-4-yl]methylsulfonyl]ethyl]acetamide Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)CCNC(C)=O)=NC(C=2C=CC(NC(=O)NCC3=CN(C)N=C3)=CC=2)=N1 JGWGVLQFWFRBDG-SFHVURJKSA-N 0.000 claims 1
QQBFRAUPVILXSJ-AWEZNQCLSA-N n-[2-fluoro-4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]azetidine-1-carboxamide Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=C(F)C(NC(=O)N3CCC3)=CC=2)=N1 QQBFRAUPVILXSJ-AWEZNQCLSA-N 0.000 claims 1
WHODPWIOCOJQJM-UHFFFAOYSA-N n-[4-[4-(methylsulfonylmethyl)-6-morpholin-4-ylpyrimidin-2-yl]phenyl]-3-oxopiperazine-1-carboxamide Chemical compound N=1C(CS(=O)(=O)C)=CC(N2CCOCC2)=NC=1C(C=C1)=CC=C1NC(=O)N1CCNC(=O)C1 WHODPWIOCOJQJM-UHFFFAOYSA-N 0.000 claims 1
QPMYJUZURQPZLK-KRWDZBQOSA-N n-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidin-2-yl]phenyl]morpholine-4-carboxamide Chemical compound C[C@H]1COCCN1C1=CC(C(C)(C)S(C)(=O)=O)=NC(C=2C=CC(NC(=O)N3CCOCC3)=CC=2)=N1 QPMYJUZURQPZLK-KRWDZBQOSA-N 0.000 claims 1
LCORXRJNMLUIEZ-HNNXBMFYSA-N n-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]azetidine-1-carboxamide Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=CC(NC(=O)N3CCC3)=CC=2)=N1 LCORXRJNMLUIEZ-HNNXBMFYSA-N 0.000 claims 1
BMEIOXXELFKDPQ-INIZCTEOSA-N n-[4-[4-[(3s)-3-methylmorpholin-4-yl]-6-(methylsulfonylmethyl)pyrimidin-2-yl]phenyl]morpholine-4-carboxamide Chemical compound C[C@H]1COCCN1C1=CC(CS(C)(=O)=O)=NC(C=2C=CC(NC(=O)N3CCOCC3)=CC=2)=N1 BMEIOXXELFKDPQ-INIZCTEOSA-N 0.000 claims 1
UKNBYYWRVZPMBG-SFHVURJKSA-N n-[4-[[2-[4-(cyclopropylcarbamoylamino)phenyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-4-yl]methylsulfonyl]phenyl]acetamide Chemical compound C[C@H]1COCCN1C1=CC(CS(=O)(=O)C=2C=CC(NC(C)=O)=CC=2)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 UKNBYYWRVZPMBG-SFHVURJKSA-N 0.000 claims 1
JANFZDIZIGEWJE-KRWDZBQOSA-N n-[4-[[2-[4-(methylcarbamoylamino)phenyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidin-4-yl]methylsulfonyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)NC)=CC=C1C1=NC(CS(=O)(=O)C=2C=CC(NC(C)=O)=CC=2)=CC(N2[C@H](COCC2)C)=N1 JANFZDIZIGEWJE-KRWDZBQOSA-N 0.000 claims 1
GJHWHPICHUCJGS-AWEZNQCLSA-N n-cyclopropyl-2-[4-(cyclopropylcarbamoylamino)phenyl]-6-[(3s)-3-methylmorpholin-4-yl]pyrimidine-4-carboxamide Chemical compound C[C@H]1COCCN1C1=CC(C(=O)NC2CC2)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 GJHWHPICHUCJGS-AWEZNQCLSA-N 0.000 claims 1
HYSCCLRQRNBYRS-HNNXBMFYSA-N n-cyclopropyl-2-[4-(cyclopropylcarbamoylamino)phenyl]-n-methyl-6-[(3s)-3-methylmorpholin-4-yl]pyrimidine-4-carboxamide Chemical compound C[C@H]1COCCN1C1=CC(C(=O)N(C)C2CC2)=NC(C=2C=CC(NC(=O)NC3CC3)=CC=2)=N1 HYSCCLRQRNBYRS-HNNXBMFYSA-N 0.000 claims 1
125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims 1
HKSQZEGSMBFHGC-UHFFFAOYSA-N pyrimidine-4-carboxamide Chemical compound NC(=O)C1=CC=NC=N1 HKSQZEGSMBFHGC-UHFFFAOYSA-N 0.000 claims 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
125000005843 halogen group Chemical group 0.000 description 272
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 69
108091007960 PI3Ks Proteins 0.000 description 60
102000038030 PI3Ks Human genes 0.000 description 60
108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 description 58
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
125000004076 pyridyl group Chemical group 0.000 description 43
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 35
150000003905 phosphatidylinositols Chemical class 0.000 description 34
239000002904 solvent Substances 0.000 description 34
108010065917 TOR Serine-Threonine Kinases Proteins 0.000 description 33
102000013530 TOR Serine-Threonine Kinases Human genes 0.000 description 33
206010028980 Neoplasm Diseases 0.000 description 32
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
125000002887 hydroxy group Chemical group [H]O* 0.000 description 29
125000000714 pyrimidinyl group Chemical group 0.000 description 28
125000003118 aryl group Chemical group 0.000 description 27
125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 description 24
239000002585 base Substances 0.000 description 24
125000001072 heteroaryl group Chemical group 0.000 description 24
125000001544 thienyl group Chemical group 0.000 description 24
125000003226 pyrazolyl group Chemical group 0.000 description 23
125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
229910052799 carbon Inorganic materials 0.000 description 20
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 20
238000006243 chemical reaction Methods 0.000 description 19
201000011510 cancer Diseases 0.000 description 18
125000004070 6 membered heterocyclic group Chemical group 0.000 description 17
150000001721 carbon Chemical group 0.000 description 17
125000002541 furyl group Chemical group 0.000 description 17
125000002883 imidazolyl group Chemical group 0.000 description 17
125000000168 pyrrolyl group Chemical group 0.000 description 17
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 15
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 15
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 15
229960005419 nitrogen Drugs 0.000 description 15
210000004027 cell Anatomy 0.000 description 14
230000000694 effects Effects 0.000 description 14
125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 14
108091000080 Phosphotransferase Proteins 0.000 description 13
239000003153 chemical reaction reagent Substances 0.000 description 13
150000002148 esters Chemical class 0.000 description 13
125000001153 fluoro group Chemical group F* 0.000 description 13
102000020233 phosphotransferase Human genes 0.000 description 13
125000002098 pyridazinyl group Chemical group 0.000 description 13
102000004190 Enzymes Human genes 0.000 description 12
108090000790 Enzymes Proteins 0.000 description 12
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
229940088598 enzyme Drugs 0.000 description 12
125000000719 pyrrolidinyl group Chemical group 0.000 description 12
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 11
238000000034 method Methods 0.000 description 11
125000002524 organometallic group Chemical group 0.000 description 11
230000011664 signaling Effects 0.000 description 11
125000000335 thiazolyl group Chemical group 0.000 description 11
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 11
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
230000001225 therapeutic effect Effects 0.000 description 10
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 10
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
230000004913 activation Effects 0.000 description 9
230000002401 inhibitory effect Effects 0.000 description 9
125000000842 isoxazolyl group Chemical group 0.000 description 9
239000001301 oxygen Substances 0.000 description 9
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 9
125000002373 5 membered heterocyclic group Chemical group 0.000 description 8
125000002619 bicyclic group Chemical group 0.000 description 8
125000004438 haloalkoxy group Chemical group 0.000 description 8
150000002632 lipids Chemical class 0.000 description 8
230000001404 mediated effect Effects 0.000 description 8
125000002950 monocyclic group Chemical group 0.000 description 8
230000001105 regulatory effect Effects 0.000 description 8
125000006413 ring segment Chemical group 0.000 description 8
125000005302 thiazolylmethyl group Chemical group [H]C1=C([H])N=C(S1)C([H])([H])* 0.000 description 8
108091008611 Protein Kinase B Proteins 0.000 description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
150000001412 amines Chemical class 0.000 description 7
230000003197 catalytic effect Effects 0.000 description 7
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 7
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 7
229960002930 sirolimus Drugs 0.000 description 7
239000011593 sulfur Substances 0.000 description 7
125000003341 7 membered heterocyclic group Chemical group 0.000 description 6
102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 6
108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
125000003566 oxetanyl group Chemical group 0.000 description 6
108090000623 proteins and genes Proteins 0.000 description 6
125000003373 pyrazinyl group Chemical group 0.000 description 6
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 6
238000012552 review Methods 0.000 description 6
125000004434 sulfur atom Chemical group 0.000 description 6
230000004083 survival effect Effects 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
125000001963 4 membered heterocyclic group Chemical group 0.000 description 5
208000005623 Carcinogenesis Diseases 0.000 description 5
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
241000699670 Mus sp. Species 0.000 description 5
102100023085 Serine/threonine-protein kinase mTOR Human genes 0.000 description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 5
230000036952 cancer formation Effects 0.000 description 5
231100000504 carcinogenesis Toxicity 0.000 description 5
230000004663 cell proliferation Effects 0.000 description 5
239000010949 copper Substances 0.000 description 5
229910052802 copper Inorganic materials 0.000 description 5
230000003831 deregulation Effects 0.000 description 5
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 5
230000005764 inhibitory process Effects 0.000 description 5
229910052751 metal Inorganic materials 0.000 description 5
239000002184 metal Substances 0.000 description 5
229910052763 palladium Inorganic materials 0.000 description 5
230000037361 pathway Effects 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
230000035755 proliferation Effects 0.000 description 5
102000004169 proteins and genes Human genes 0.000 description 5
230000004044 response Effects 0.000 description 5
230000019491 signal transduction Effects 0.000 description 5
230000000638 stimulation Effects 0.000 description 5
125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 5
150000003573 thiols Chemical class 0.000 description 5
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
208000024172 Cardiovascular disease Diseases 0.000 description 4
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 4
241000282414 Homo sapiens Species 0.000 description 4
208000008770 Multiple Hamartoma Syndrome Diseases 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 4
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 4
230000001419 dependent effect Effects 0.000 description 4
229940079593 drug Drugs 0.000 description 4
238000001727 in vivo Methods 0.000 description 4
239000003112 inhibitor Substances 0.000 description 4
239000003628 mammalian target of rapamycin inhibitor Substances 0.000 description 4
239000000203 mixture Substances 0.000 description 4
210000000440 neutrophil Anatomy 0.000 description 4
230000003389 potentiating effect Effects 0.000 description 4
229940002612 prodrug Drugs 0.000 description 4
239000000651 prodrug Substances 0.000 description 4
125000006513 pyridinyl methyl group Chemical group 0.000 description 4
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 3
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
206010058467 Lung neoplasm malignant Diseases 0.000 description 3
108700020796 Oncogene Proteins 0.000 description 3
102000001253 Protein Kinase Human genes 0.000 description 3
102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 3
108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 3
102100033810 RAC-alpha serine/threonine-protein kinase Human genes 0.000 description 3
230000029936 alkylation Effects 0.000 description 3
238000005804 alkylation reaction Methods 0.000 description 3
XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 3
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 3
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
210000000481 breast Anatomy 0.000 description 3
210000004413 cardiac myocyte Anatomy 0.000 description 3
210000003679 cervix uteri Anatomy 0.000 description 3
125000000753 cycloalkyl group Chemical group 0.000 description 3
210000002889 endothelial cell Anatomy 0.000 description 3
230000006870 function Effects 0.000 description 3
230000014509 gene expression Effects 0.000 description 3
239000003102 growth factor Substances 0.000 description 3
208000026278 immune system disease Diseases 0.000 description 3
125000001041 indolyl group Chemical group 0.000 description 3
230000002757 inflammatory effect Effects 0.000 description 3
210000000265 leukocyte Anatomy 0.000 description 3
239000003446 ligand Substances 0.000 description 3
201000005202 lung cancer Diseases 0.000 description 3
208000020816 lung neoplasm Diseases 0.000 description 3
230000003211 malignant effect Effects 0.000 description 3
108020004999 messenger RNA Proteins 0.000 description 3
230000035772 mutation Effects 0.000 description 3
125000001624 naphthyl group Chemical group 0.000 description 3
230000000414 obstructive effect Effects 0.000 description 3
230000002018 overexpression Effects 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
230000002265 prevention Effects 0.000 description 3
108060006633 protein kinase Proteins 0.000 description 3
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 3
102000005962 receptors Human genes 0.000 description 3
108020003175 receptors Proteins 0.000 description 3
238000006268 reductive amination reaction Methods 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000000758 substrate Substances 0.000 description 3
208000011580 syndromic disease Diseases 0.000 description 3
210000001519 tissue Anatomy 0.000 description 3
238000013519 translation Methods 0.000 description 3
210000004881 tumor cell Anatomy 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
208000024893 Acute lymphoblastic leukemia Diseases 0.000 description 2
208000014697 Acute lymphocytic leukaemia Diseases 0.000 description 2
208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 description 2
201000007815 Bannayan-Riley-Ruvalcaba syndrome Diseases 0.000 description 2
206010005949 Bone cancer Diseases 0.000 description 2
208000018084 Bone neoplasm Diseases 0.000 description 2
201000009030 Carcinoma Diseases 0.000 description 2
208000010833 Chronic myeloid leukaemia Diseases 0.000 description 2
108091007958 Class I PI3Ks Proteins 0.000 description 2
108091007963 Class III PI3Ks Proteins 0.000 description 2
201000002847 Cowden syndrome Diseases 0.000 description 2
239000007821 HATU Substances 0.000 description 2
102100031561 Hamartin Human genes 0.000 description 2
208000002927 Hamartoma Diseases 0.000 description 2
206010021143 Hypoxia Diseases 0.000 description 2
108090001007 Interleukin-8 Proteins 0.000 description 2
206010025323 Lymphomas Diseases 0.000 description 2
208000034578 Multiple myelomas Diseases 0.000 description 2
208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 description 2
239000012828 PI3K inhibitor Substances 0.000 description 2
108010011536 PTEN Phosphohydrolase Proteins 0.000 description 2
102000014160 PTEN Phosphohydrolase Human genes 0.000 description 2
206010034764 Peutz-Jeghers syndrome Diseases 0.000 description 2
102100036056 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform Human genes 0.000 description 2
101710204747 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform Proteins 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
206010035226 Plasma cell myeloma Diseases 0.000 description 2
102000010995 Pleckstrin homology domains Human genes 0.000 description 2
108050001185 Pleckstrin homology domains Proteins 0.000 description 2
208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 description 2
102000001708 Protein Isoforms Human genes 0.000 description 2
108010029485 Protein Isoforms Proteins 0.000 description 2
206010039491 Sarcoma Diseases 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
108010040002 Tumor Suppressor Proteins Proteins 0.000 description 2
102000001742 Tumor Suppressor Proteins Human genes 0.000 description 2
208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
239000002253 acid Substances 0.000 description 2
230000003213 activating effect Effects 0.000 description 2
150000001263 acyl chlorides Chemical class 0.000 description 2
239000000556 agonist Substances 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
125000001769 aryl amino group Chemical group 0.000 description 2
125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 description 2
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 2
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
208000026900 bile duct neoplasm Diseases 0.000 description 2
230000027455 binding Effects 0.000 description 2
210000000988 bone and bone Anatomy 0.000 description 2
125000001246 bromo group Chemical group Br* 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
230000010261 cell growth Effects 0.000 description 2
230000001413 cellular effect Effects 0.000 description 2
230000033077 cellular process Effects 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
239000007822 coupling agent Substances 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
125000000392 cycloalkenyl group Chemical group 0.000 description 2
230000003436 cytoskeletal effect Effects 0.000 description 2
230000002950 deficient Effects 0.000 description 2
238000013461 design Methods 0.000 description 2
QPMLSUSACCOBDK-UHFFFAOYSA-N diazepane Chemical compound C1CCNNCC1 QPMLSUSACCOBDK-UHFFFAOYSA-N 0.000 description 2
210000003238 esophagus Anatomy 0.000 description 2
230000002496 gastric effect Effects 0.000 description 2
125000001188 haloalkyl group Chemical group 0.000 description 2
201000010536 head and neck cancer Diseases 0.000 description 2
208000014829 head and neck neoplasm Diseases 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
229960003444 immunosuppressant agent Drugs 0.000 description 2
239000003018 immunosuppressive agent Substances 0.000 description 2
208000027866 inflammatory disease Diseases 0.000 description 2
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
125000002346 iodo group Chemical group I* 0.000 description 2
210000003734 kidney Anatomy 0.000 description 2
208000032839 leukemia Diseases 0.000 description 2
210000004185 liver Anatomy 0.000 description 2
208000003747 lymphoid leukemia Diseases 0.000 description 2
208000019420 lymphoid neoplasm Diseases 0.000 description 2
230000005012 migration Effects 0.000 description 2
238000013508 migration Methods 0.000 description 2
230000004899 motility Effects 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
208000002154 non-small cell lung carcinoma Diseases 0.000 description 2
230000002611 ovarian Effects 0.000 description 2
210000001672 ovary Anatomy 0.000 description 2
210000000496 pancreas Anatomy 0.000 description 2
239000012660 pharmacological inhibitor Substances 0.000 description 2
229940043441 phosphoinositide 3-kinase inhibitor Drugs 0.000 description 2
230000026731 phosphorylation Effects 0.000 description 2
238000006366 phosphorylation reaction Methods 0.000 description 2
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
230000008569 process Effects 0.000 description 2
210000002307 prostate Anatomy 0.000 description 2
230000008521 reorganization Effects 0.000 description 2
238000011160 research Methods 0.000 description 2
210000002345 respiratory system Anatomy 0.000 description 2
208000023504 respiratory system disease Diseases 0.000 description 2
210000003491 skin Anatomy 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
239000012453 solvate Substances 0.000 description 2
210000002536 stromal cell Anatomy 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
210000001550 testis Anatomy 0.000 description 2
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 2
210000001685 thyroid gland Anatomy 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 2
239000000225 tumor suppressor protein Substances 0.000 description 2
238000011144 upstream manufacturing Methods 0.000 description 2
210000003932 urinary bladder Anatomy 0.000 description 2
210000004291 uterus Anatomy 0.000 description 2
210000005166 vasculature Anatomy 0.000 description 2
210000003905 vulva Anatomy 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
229910052727 yttrium Inorganic materials 0.000 description 2
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 1
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
IMYKAGLWJYIETB-UHFFFAOYSA-N 3-methyl-2h-1,3,4-thiadiazole Chemical compound CN1CSC=N1 IMYKAGLWJYIETB-UHFFFAOYSA-N 0.000 description 1
SFWWGMKXCYLZEG-UHFFFAOYSA-N 3-methylmorpholine Chemical compound CC1COCCN1 SFWWGMKXCYLZEG-UHFFFAOYSA-N 0.000 description 1
YHWWKRCQPVDEBT-UHFFFAOYSA-N 4-[6-(benzenesulfonylmethyl)-2-pyridin-2-ylpyrimidin-4-yl]morpholine Chemical compound C=1C=CC=CC=1S(=O)(=O)CC(N=1)=CC(N2CCOCC2)=NC=1C1=CC=CC=N1 YHWWKRCQPVDEBT-UHFFFAOYSA-N 0.000 description 1
NTDFJDVHECTHPT-UHFFFAOYSA-N 4-[6-(benzenesulfonylmethyl)-2-pyridin-4-ylpyrimidin-4-yl]morpholine Chemical compound C=1C=CC=CC=1S(=O)(=O)CC(N=1)=CC(N2CCOCC2)=NC=1C1=CC=NC=C1 NTDFJDVHECTHPT-UHFFFAOYSA-N 0.000 description 1
AGQOIYCTCOEHGR-UHFFFAOYSA-N 5-methyl-1,2-oxazole Chemical compound CC1=CC=NO1 AGQOIYCTCOEHGR-UHFFFAOYSA-N 0.000 description 1
102000007469 Actins Human genes 0.000 description 1
108010085238 Actins Proteins 0.000 description 1
230000007730 Akt signaling Effects 0.000 description 1
101100450705 Caenorhabditis elegans hif-1 gene Proteins 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
206010007572 Cardiac hypertrophy Diseases 0.000 description 1
208000006029 Cardiomegaly Diseases 0.000 description 1
102000014914 Carrier Proteins Human genes 0.000 description 1
102000000844 Cell Surface Receptors Human genes 0.000 description 1
108010001857 Cell Surface Receptors Proteins 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical class [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
208000012609 Cowden disease Diseases 0.000 description 1
108020004414 DNA Proteins 0.000 description 1
BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
102100022466 Eukaryotic translation initiation factor 4E-binding protein 1 Human genes 0.000 description 1
108050000946 Eukaryotic translation initiation factor 4E-binding protein 1 Proteins 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
108090000386 Fibroblast Growth Factor 1 Proteins 0.000 description 1
102100031706 Fibroblast growth factor 1 Human genes 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 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
102000009465 Growth Factor Receptors Human genes 0.000 description 1
108010009202 Growth Factor Receptors Proteins 0.000 description 1
206010019280 Heart failures Diseases 0.000 description 1
101000600756 Homo sapiens 3-phosphoinositide-dependent protein kinase 1 Proteins 0.000 description 1
101000795643 Homo sapiens Hamartin Proteins 0.000 description 1
101001059454 Homo sapiens Serine/threonine-protein kinase MARK2 Proteins 0.000 description 1
101000864057 Homo sapiens Serine/threonine-protein kinase SMG1 Proteins 0.000 description 1
101000796673 Homo sapiens Transformation/transcription domain-associated protein Proteins 0.000 description 1
101000795659 Homo sapiens Tuberin Proteins 0.000 description 1
101001117146 Homo sapiens [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 1, mitochondrial Proteins 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
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 1
102000000521 Immunophilins Human genes 0.000 description 1
108010016648 Immunophilins Proteins 0.000 description 1
102100023915 Insulin Human genes 0.000 description 1
108090001061 Insulin Proteins 0.000 description 1
102100025087 Insulin receptor substrate 1 Human genes 0.000 description 1
101710201824 Insulin receptor substrate 1 Proteins 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
208000022010 Lhermitte-Duclos disease Diseases 0.000 description 1
206010025102 Lung infiltration Diseases 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
206010027476 Metastases Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
206010027540 Microcytosis Diseases 0.000 description 1
101150097381 Mtor gene Proteins 0.000 description 1
241001529936 Murinae Species 0.000 description 1
HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
PRQROPMIIGLWRP-UHFFFAOYSA-N N-formyl-methionyl-leucyl-phenylalanin Chemical compound CSCCC(NC=O)C(=O)NC(CC(C)C)C(=O)NC(C(O)=O)CC1=CC=CC=C1 PRQROPMIIGLWRP-UHFFFAOYSA-N 0.000 description 1
102000043276 Oncogene Human genes 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
235000016067 Polianthes tuberosa Nutrition 0.000 description 1
244000014047 Polianthes tuberosa Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
208000007531 Proteus syndrome Diseases 0.000 description 1
101710194805 Putative repressor Proteins 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 description 1
101710100968 Receptor tyrosine-protein kinase erbB-2 Proteins 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
208000034189 Sclerosis Diseases 0.000 description 1
229940124639 Selective inhibitor Drugs 0.000 description 1
MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
102100028904 Serine/threonine-protein kinase MARK2 Human genes 0.000 description 1
102100029938 Serine/threonine-protein kinase SMG1 Human genes 0.000 description 1
102100026715 Serine/threonine-protein kinase STK11 Human genes 0.000 description 1
101710181599 Serine/threonine-protein kinase STK11 Proteins 0.000 description 1
206010041067 Small cell lung cancer Diseases 0.000 description 1
210000001744 T-lymphocyte Anatomy 0.000 description 1
102100032762 Transformation/transcription domain-associated protein Human genes 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
102100031638 Tuberin Human genes 0.000 description 1
102000044209 Tumor Suppressor Genes Human genes 0.000 description 1
108700025716 Tumor Suppressor Genes Proteins 0.000 description 1
102100024148 [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 1, mitochondrial Human genes 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
206010069351 acute lung injury Diseases 0.000 description 1
230000003044 adaptive effect Effects 0.000 description 1
238000012382 advanced drug delivery Methods 0.000 description 1
125000005083 alkoxyalkoxy group Chemical group 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
230000000172 allergic effect Effects 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
230000003321 amplification Effects 0.000 description 1
230000002491 angiogenic effect Effects 0.000 description 1
230000001093 anti-cancer Effects 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
230000001028 anti-proliverative effect Effects 0.000 description 1
230000001640 apoptogenic effect Effects 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
238000003556 assay Methods 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
230000002238 attenuated effect Effects 0.000 description 1
230000004900 autophagic degradation Effects 0.000 description 1
GMWFCJXSQQHBPI-UHFFFAOYSA-N azetidin-3-ol Chemical compound OC1CNC1 GMWFCJXSQQHBPI-UHFFFAOYSA-N 0.000 description 1
125000002393 azetidinyl group Chemical group 0.000 description 1
210000003719 b-lymphocyte Anatomy 0.000 description 1
230000008901 benefit Effects 0.000 description 1
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 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
108091008324 binding proteins Proteins 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
210000001185 bone marrow Anatomy 0.000 description 1
244000309464 bull Species 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
125000001721 carboxyacetyl group Chemical group 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
230000020411 cell activation Effects 0.000 description 1
230000003915 cell function Effects 0.000 description 1
230000004709 cell invasion Effects 0.000 description 1
230000005754 cellular signaling Effects 0.000 description 1
230000008859 change Effects 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
230000003399 chemotactic effect Effects 0.000 description 1
230000035605 chemotaxis Effects 0.000 description 1
210000001072 colon Anatomy 0.000 description 1
125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
150000004683 dihydrates Chemical class 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
230000007783 downstream signaling Effects 0.000 description 1
238000009510 drug design Methods 0.000 description 1
238000009509 drug development Methods 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
230000003511 endothelial effect Effects 0.000 description 1
239000002158 endotoxin Substances 0.000 description 1
239000002532 enzyme inhibitor Substances 0.000 description 1
210000002919 epithelial cell Anatomy 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
229960005167 everolimus Drugs 0.000 description 1
238000002376 fluorescence recovery after photobleaching Methods 0.000 description 1
239000008103 glucose Substances 0.000 description 1
210000003958 hematopoietic stem cell Anatomy 0.000 description 1
230000011132 hemopoiesis Effects 0.000 description 1
125000004446 heteroarylalkyl group Chemical group 0.000 description 1
125000005241 heteroarylamino group Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
210000003630 histaminocyte Anatomy 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000007954 hypoxia Effects 0.000 description 1
210000002865 immune cell Anatomy 0.000 description 1
210000000987 immune system Anatomy 0.000 description 1
230000036039 immunity Effects 0.000 description 1
230000016784 immunoglobulin production Effects 0.000 description 1
230000001861 immunosuppressant effect Effects 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
230000008595 infiltration Effects 0.000 description 1
238000001764 infiltration Methods 0.000 description 1
210000004969 inflammatory cell Anatomy 0.000 description 1
150000002485 inorganic esters Chemical class 0.000 description 1
229940125396 insulin Drugs 0.000 description 1
102000006495 integrins Human genes 0.000 description 1
108010044426 integrins Proteins 0.000 description 1
230000003993 interaction Effects 0.000 description 1
230000003834 intracellular effect Effects 0.000 description 1
210000004020 intracellular membrane Anatomy 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
229940124302 mTOR inhibitor Drugs 0.000 description 1
239000003120 macrolide antibiotic agent Substances 0.000 description 1
210000002540 macrophage Anatomy 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical class OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
210000004962 mammalian cell Anatomy 0.000 description 1
230000009401 metastasis Effects 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
125000002757 morpholinyl group Chemical group 0.000 description 1
JTSLALYXYSRPGW-UHFFFAOYSA-N n-[5-(4-cyanophenyl)-1h-pyrrolo[2,3-b]pyridin-3-yl]pyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(=O)NC(C1=C2)=CNC1=NC=C2C1=CC=C(C#N)C=C1 JTSLALYXYSRPGW-UHFFFAOYSA-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
125000004998 naphthylethyl group Chemical group C1(=CC=CC2=CC=CC=C12)CC* 0.000 description 1
125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000002547 new drug Substances 0.000 description 1
238000003199 nucleic acid amplification method Methods 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
230000007170 pathology Effects 0.000 description 1
210000003024 peritoneal macrophage Anatomy 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
150000003906 phosphoinositides Chemical class 0.000 description 1
DCWXELXMIBXGTH-QMMMGPOBSA-N phosphonotyrosine Chemical group OC(=O)[C@@H](N)CC1=CC=C(OP(O)(O)=O)C=C1 DCWXELXMIBXGTH-QMMMGPOBSA-N 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
125000001557 phthalyl group Chemical group C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
230000001023 pro-angiogenic effect Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
150000003244 quercetin derivatives Chemical class 0.000 description 1
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
108700042226 ras Genes Proteins 0.000 description 1
108091008598 receptor tyrosine kinases Proteins 0.000 description 1
102000027426 receptor tyrosine kinases Human genes 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
230000009712 regulation of translation Effects 0.000 description 1
230000008844 regulatory mechanism Effects 0.000 description 1
208000037803 restenosis Diseases 0.000 description 1
230000000284 resting effect Effects 0.000 description 1
210000003705 ribosome Anatomy 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
230000007781 signaling event Effects 0.000 description 1
230000009131 signaling function Effects 0.000 description 1
208000000587 small cell lung carcinoma Diseases 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
230000001629 suppression Effects 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 description 1
238000013518 transcription Methods 0.000 description 1
230000035897 transcription Effects 0.000 description 1
238000002054 transplantation Methods 0.000 description 1
230000032258 transport Effects 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
150000004684 trihydrates Chemical class 0.000 description 1
230000005747 tumor angiogenesis Effects 0.000 description 1
231100000588 tumorigenic Toxicity 0.000 description 1
230000000381 tumorigenic effect Effects 0.000 description 1
230000007306 turnover Effects 0.000 description 1
230000009750 upstream signaling Effects 0.000 description 1
230000002792 vascular Effects 0.000 description 1
210000003556 vascular endothelial cell Anatomy 0.000 description 1
QDLHCMPXEPAAMD-QAIWCSMKSA-N wortmannin Chemical compound C1([C@]2(C)C3=C(C4=O)OC=C3C(=O)O[C@@H]2COC)=C4[C@@H]2CCC(=O)[C@@]2(C)C[C@H]1OC(C)=O QDLHCMPXEPAAMD-QAIWCSMKSA-N 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

ES07789273T 2006-08-24 2007-08-21 Derivados de morfolino pirimidina útiles en el tratamiento de trastornos proliferativos Active ES2393215T3 (es)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
GB0616747A GB0616747D0 (en)	2006-08-24	2006-08-24	Novel compounds
GB0616747		2006-08-24
US94854407P	2007-07-09	2007-07-09
US948544P		2007-07-09
PCT/GB2007/003173 WO2008023159A1 (en)	2006-08-24	2007-08-21	Morpholino pyrimidine derivatives useful in the treatment of proliferative disorders

Publications (1)

Publication Number	Publication Date
ES2393215T3 true ES2393215T3 (es)	2012-12-19

Family

ID=37102735

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ES07789273T Active ES2393215T3 (es)	2006-08-24	2007-08-21	Derivados de morfolino pirimidina útiles en el tratamiento de trastornos proliferativos

Country Status (7)

Country	Link
CN (2)	CN101541781B (pt)
BR (1)	BRPI0715609A2 (pt)
ES (1)	ES2393215T3 (pt)
GB (1)	GB0616747D0 (pt)
RU (1)	RU2440349C2 (pt)
TW (1)	TW200817384A (pt)
ZA (1)	ZA200901015B (pt)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2659851C (en) *	2006-08-23	2014-02-25	Kudos Pharmaceuticals Limited	2-methylmorpholine pyrido-, pyrazo- and pyrimido-pyrimidine derivatives as mtor inhibitors
BR112012015827A2 (pt) *	2009-12-28	2016-12-06	Dcb Usa Llc	novos compostos de pirimidina como inibidores de mtor e p13k
US8618111B2 (en) *	2010-01-26	2013-12-31	Boehringer Ingelheim International Gmbh	5-alkynyl-pyrimidines
US8791107B2 (en) *	2011-02-25	2014-07-29	Takeda Pharmaceutical Company Limited	N-substituted oxazinopteridines and oxazinopteridinones
WO2013041652A1 (en) *	2011-09-21	2013-03-28	Cellzome Limited	Morpholino substituted urea or carbamate derivatives as mtor inhibitors
ES2624307T3 (es)	2012-05-15	2017-07-13	Cancer Research Technology Ltd	5-[[4-[[Morfolin-2-il]metilamino]-5-(trifluorometil)-2-piridil]amino]pirazin-2-carbonitrilo y usos terapéuticos del mismo
TW202204348A (zh)	2020-04-07	2022-02-01	美商西爾拉癌症醫學公司	Ｃｈｋ１抑制劑之合成方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19834044A1 (de) *	1998-07-29	2000-02-03	Bayer Ag	Neue substituierte Pyrazolderivate
KR100774855B1 (ko) *	2000-04-27	2007-11-08	아스텔라스세이야쿠 가부시키가이샤	축합 헤테로아릴 유도체
CN1473156A (zh) *	2000-11-10	2004-02-04	-	嘧啶衍生物及其作为神经肽y受体配体的用途
EA013811B1 (ru) *	2002-11-21	2010-08-30	Новартис Вэксинес Энд Дайэгностикс, Инк.	2,4,6-тризамещённые пиримидины, являющиеся ингибиторами фосфотидилинозитол(pi)-3-киназы, и их применение при лечении рака
GB0415364D0 (en) *	2004-07-09	2004-08-11	Astrazeneca Ab	Pyrimidine derivatives
GB0415367D0 (en) *	2004-07-09	2004-08-11	Astrazeneca Ab	Pyrimidine derivatives
WO2006053227A2 (en) *	2004-11-10	2006-05-18	Synta Pharmaceuticals Corp.	Il-12 modulatory compounds

2006
- 2006-08-24 GB GB0616747A patent/GB0616747D0/en not_active Ceased
2007
- 2007-08-21 TW TW96130916A patent/TW200817384A/zh unknown
- 2007-08-21 BR BRPI0715609-0A2A patent/BRPI0715609A2/pt not_active IP Right Cessation
- 2007-08-21 ES ES07789273T patent/ES2393215T3/es active Active
- 2007-08-21 RU RU2009110255/04A patent/RU2440349C2/ru not_active IP Right Cessation
- 2007-08-21 CN CN200780039262.7A patent/CN101541781B/zh not_active Expired - Fee Related
- 2007-08-22 CN CNA2007800392665A patent/CN101558046A/zh active Pending
2009
- 2009-02-12 ZA ZA200901015A patent/ZA200901015B/xx unknown

Also Published As

Publication number	Publication date
RU2009110255A (ru)	2010-09-27
RU2440349C2 (ru)	2012-01-20
BRPI0715609A2 (pt)	2013-10-08
CN101558046A (zh)	2009-10-14
CN101541781A (zh)	2009-09-23
GB0616747D0 (en)	2006-10-04
CN101541781B (zh)	2014-01-08
ZA200901015B (en)	2010-08-25
TW200817384A (en)	2008-04-16

Publication	Publication Date	Title
AU2007287428B2 (en)	2011-08-11	Morpholino pyrimidine derivatives useful in the treatment of proliferative disorders
JP7762957B2 (ja)	2025-10-31	Ｍｅｔｔｌ３阻害化合物
ES2385692T3 (es)	2012-07-30	Derivados de morfolino pirimidina usados en enfermedades relacionadas con mTOR quinasa y/o PI3K
US8017611B2 (en)	2011-09-13	Pyridine and pyrazine derivatives -083
JP5000726B2 (ja)	2012-08-15	新規化合物
JP2009538351A (ja)	2009-11-05	細胞増殖阻害剤としての２−ヘテロシクロアミノ−４−イミダゾリルピリミジン
CA2692725A1 (en)	2009-01-15	Compound - 946
JP2010503651A (ja)	2010-02-04	増殖性障害の治療用のＰＩ３Ｋ及びｍＴＯＲ阻害剤としての２−ベンゾイミダゾリル−６−モルホリノ−フェニルピリミジン誘導体
WO2009024825A1 (en)	2009-02-26	2-pyrazinylbenzimidazole derivatives as receptor tyrosine kinase inhibitors
US20080027076A1 (en)	2008-01-31	Pyrimidines With Tie2 (Tek) Activity
ES2393215T3 (es)	2012-12-19	Derivados de morfolino pirimidina útiles en el tratamiento de trastornos proliferativos
US20080153838A1 (en)	2008-06-26	Compounds Having Tie2 (Tek) Activity
ES2364864T3 (es)	2011-09-15	Acilaminopirazoles como inhibidores de fgfr.
KR20070032810A (ko)	2007-03-22	포스포티딜이노시톨（ｐｉ）３―키나제 저해제로서의２，４，６―삼치환 피리미딘 및 암 치료에서의 그의 용도
JP2007517007A (ja)	2007-06-28	Ｔｉｅ２（ＴＥＫ）活性を持つピリミジン
HK1130776B (en)	2013-05-10	Morpholino pyrimidine derivatives useful in the treatment of proliferative disorders
HK1139137B (en)	2012-01-06	Acylaminopyrazoles as fgfr inhibitors
MX2008008945A (en)	2008-09-26	Morpholino pyrimidine derivatives and their use in therapy
KR20070032064A (ko)	2007-03-20	포스포티딜이노시톨(ｐｉ) 3-키나제 저해제로서의2,4,6-삼치환 피리미딘 및 암 치료에 있어서의 이의 용도
RS51811B (sr)	2011-12-31	Acilaminopirazoli kao inhibitori fgfr