AU2009251863B2 - 2, 6-diamino-pyrimidin- 5-yl-carboxamides as syk or JAK kinases inhibitors - Google Patents

2, 6-diamino-pyrimidin- 5-yl-carboxamides as syk or JAK kinases inhibitors Download PDF

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Publication number: AU2009251863B2
Authority: AU; Australia
Prior art keywords: carboxamide; pyrimidine; phenylamino; cyclopropylamino; ylamino
Prior art date: 2008-04-16
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

AU2009251863A

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English (en)

Other versions

AU2009251863A1 (en

AU2009251863A2 (en

Inventor

Shawn M. Bauer

Wolin Huang

Zhaozhong J. Jia

Mukund Mehrotra

Anjali Pandey

Jack W. Rose

Yonghong Song

Chandrasekar Venkataramani

Qing Xu

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.)

Alexion Pharmaceuticals Inc

Original Assignee

Alexion Pharmaceuticals Inc

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.)

2008-04-16

Filing date

2009-04-16

Publication date

2014-09-25

2009-04-16 Application filed by Alexion Pharmaceuticals Inc filed Critical Alexion Pharmaceuticals Inc

2009-04-16 Priority claimed from PCT/US2009/002420 external-priority patent/WO2009145856A1/en

2009-12-03 Publication of AU2009251863A1 publication Critical patent/AU2009251863A1/en

2011-06-09 Publication of AU2009251863A2 publication Critical patent/AU2009251863A2/en

2014-09-25 Application granted granted Critical

2014-09-25 Publication of AU2009251863B2 publication Critical patent/AU2009251863B2/en

2023-06-15 Assigned to ALEXION PHARMACEUTICALS, INC. reassignment ALEXION PHARMACEUTICALS, INC. Request for Assignment Assignors: PORTOLA PHARMACEUTICALS, INC.

Status Active legal-status Critical Current

2029-04-16 Anticipated expiration legal-status Critical

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239000003112 inhibitor Substances 0.000 title abstract description 37
108010024121 Janus Kinases Proteins 0.000 title description 23
102000015617 Janus Kinases Human genes 0.000 title description 23
108010016672 Syk Kinase Proteins 0.000 title description 18
102000000551 Syk Kinase Human genes 0.000 title description 18
VULZVYGZVOMUKU-UHFFFAOYSA-N 2,4-diaminopyrimidine-5-carboxamide Chemical class NC(=O)C1=CN=C(N)N=C1N VULZVYGZVOMUKU-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 351
102000042838 JAK family Human genes 0.000 claims abstract description 120
108091082332 JAK family Proteins 0.000 claims abstract description 120
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 115
238000000034 method Methods 0.000 claims abstract description 102
150000003839 salts Chemical class 0.000 claims abstract description 74
230000000694 effects Effects 0.000 claims abstract description 70
230000001404 mediated effect Effects 0.000 claims abstract description 65
208000035475 disorder Diseases 0.000 claims abstract description 57
208000023275 Autoimmune disease Diseases 0.000 claims abstract description 35
206010020751 Hypersensitivity Diseases 0.000 claims abstract description 21
208000032839 leukemia Diseases 0.000 claims abstract description 17
208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims abstract description 16
208000007536 Thrombosis Diseases 0.000 claims abstract description 15
208000006673 asthma Diseases 0.000 claims abstract description 12
230000002062 proliferating effect Effects 0.000 claims abstract description 12
206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 12
230000007815 allergy Effects 0.000 claims abstract description 11
208000027866 inflammatory disease Diseases 0.000 claims abstract description 10
208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 8
208000026935 allergic disease Diseases 0.000 claims abstract description 7
238000002360 preparation method Methods 0.000 claims abstract description 7
-1 amino, hydroxy Chemical group 0.000 claims description 184
101150110875 Syk gene Proteins 0.000 claims description 179
239000000203 mixture Substances 0.000 claims description 121
125000000217 alkyl group Chemical group 0.000 claims description 117
210000004027 cell Anatomy 0.000 claims description 104
125000000623 heterocyclic group Chemical group 0.000 claims description 92
125000001424 substituent group Chemical group 0.000 claims description 85
125000003118 aryl group Chemical group 0.000 claims description 74
QDXGKRWDQCEABB-UHFFFAOYSA-N pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=CN=C1 QDXGKRWDQCEABB-UHFFFAOYSA-N 0.000 claims description 60
201000010099 disease Diseases 0.000 claims description 57
125000000753 cycloalkyl group Chemical group 0.000 claims description 51
229910052739 hydrogen Inorganic materials 0.000 claims description 43
201000006417 multiple sclerosis Diseases 0.000 claims description 43
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 39
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
125000004043 oxo group Chemical group O=* 0.000 claims description 35
125000003545 alkoxy group Chemical group 0.000 claims description 30
125000000304 alkynyl group Chemical group 0.000 claims description 30
125000003342 alkenyl group Chemical group 0.000 claims description 27
239000003814 drug Substances 0.000 claims description 27
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 27
210000003719 b-lymphocyte Anatomy 0.000 claims description 26
229910052757 nitrogen Inorganic materials 0.000 claims description 26
230000019491 signal transduction Effects 0.000 claims description 24
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 23
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 21
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
230000002401 inhibitory effect Effects 0.000 claims description 19
108091000080 Phosphotransferase Proteins 0.000 claims description 17
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 17
102000020233 phosphotransferase Human genes 0.000 claims description 17
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 16
125000002947 alkylene group Chemical group 0.000 claims description 14
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 14
125000004093 cyano group Chemical group *C#N 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
208000037803 restenosis Diseases 0.000 claims description 12
208000002250 Hematologic Neoplasms Diseases 0.000 claims description 11
239000003937 drug carrier Substances 0.000 claims description 11
206010025323 Lymphomas Diseases 0.000 claims description 10
125000006356 alkylene carbonyl group Chemical group 0.000 claims description 9
239000003085 diluting agent Substances 0.000 claims description 9
208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 claims description 8
208000010125 myocardial infarction Diseases 0.000 claims description 8
208000007056 sickle cell anemia Diseases 0.000 claims description 8
208000028622 Immune thrombocytopenia Diseases 0.000 claims description 6
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
NDQROJWWYNXXBY-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(piperidin-4-ylmethylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCC2CCNCC2)=N1 NDQROJWWYNXXBY-UHFFFAOYSA-N 0.000 claims description 5
208000004476 Acute Coronary Syndrome Diseases 0.000 claims description 5
206010002388 Angina unstable Diseases 0.000 claims description 5
201000001320 Atherosclerosis Diseases 0.000 claims description 5
206010062506 Heparin-induced thrombocytopenia Diseases 0.000 claims description 5
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208000021386 Sjogren Syndrome Diseases 0.000 claims description 5
208000007814 Unstable Angina Diseases 0.000 claims description 5
208000007475 hemolytic anemia Diseases 0.000 claims description 5
201000004332 intermediate coronary syndrome Diseases 0.000 claims description 5
206010025135 lupus erythematosus Diseases 0.000 claims description 5
208000035868 Vascular inflammations Diseases 0.000 claims description 4
NWSQMSSJOTZBLY-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(piperidin-3-ylmethylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCC2CNCCC2)=N1 NWSQMSSJOTZBLY-UHFFFAOYSA-N 0.000 claims description 3
208000014767 Myeloproliferative disease Diseases 0.000 claims description 3
208000020832 chronic kidney disease Diseases 0.000 claims description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
208000028208 end stage renal disease Diseases 0.000 claims description 3
201000000523 end stage renal failure Diseases 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
TWINKIYWPUHSLK-UHFFFAOYSA-N 2,4-bis[4-(4-acetylpiperazin-1-yl)anilino]pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC=2C=CC(=CC=2)N2CCN(CC2)C(C)=O)=N1 TWINKIYWPUHSLK-UHFFFAOYSA-N 0.000 claims description 2
CULNFFVRPDWXDC-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)-3-chloroanilino]-4-(cyclobutylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C(=C1)Cl)=CC=C1NC1=NC=C(C(N)=O)C(NC2CCC2)=N1 CULNFFVRPDWXDC-UHFFFAOYSA-N 0.000 claims description 2
SZDDQPRVZVVJRE-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)-3-chloroanilino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C(=C1)Cl)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 SZDDQPRVZVVJRE-UHFFFAOYSA-N 0.000 claims description 2
NNCYKJMNCXLNIP-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(5-hydroxypentylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCCCCCO)=N1 NNCYKJMNCXLNIP-UHFFFAOYSA-N 0.000 claims description 2
UBNOYEGKTNHLES-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(cyclobutylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CCC2)=N1 UBNOYEGKTNHLES-UHFFFAOYSA-N 0.000 claims description 2
DIQRQHSVKYZYQJ-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-[(1-acetylpiperidin-4-yl)methylamino]pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCC1CNC1=NC(NC=2C=CC(=CC=2)N2CCN(CC2)C(C)=O)=NC=C1C(N)=O DIQRQHSVKYZYQJ-UHFFFAOYSA-N 0.000 claims description 2
SYAIHPHAYGOQIX-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-[(1-methylsulfonylpiperidin-4-yl)methylamino]pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCC2CCN(CC2)S(C)(=O)=O)=N1 SYAIHPHAYGOQIX-UHFFFAOYSA-N 0.000 claims description 2
DPXRUDBEHDDDTH-UHFFFAOYSA-N 2-[4-[4-(cyclopropanecarbonyl)piperazin-1-yl]anilino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1N(CC1)CCN1C(=O)C1CC1 DPXRUDBEHDDDTH-UHFFFAOYSA-N 0.000 claims description 2
BFCMZNDHPTWHRE-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-(4-propanoylpiperazin-1-yl)anilino]pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)CC)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 BFCMZNDHPTWHRE-UHFFFAOYSA-N 0.000 claims description 2
AKRODORBCFIPKJ-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-[4-(2-methoxyacetyl)piperazin-1-yl]anilino]pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)COC)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 AKRODORBCFIPKJ-UHFFFAOYSA-N 0.000 claims description 2
208000003343 Antiphospholipid Syndrome Diseases 0.000 claims description 2
206010056370 Congestive cardiomyopathy Diseases 0.000 claims description 2
208000011231 Crohn disease Diseases 0.000 claims description 2
201000010046 Dilated cardiomyopathy Diseases 0.000 claims description 2
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 2
208000003476 primary myelofibrosis Diseases 0.000 claims description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 4
125000001475 halogen functional group Chemical group 0.000 claims 3
SCWKRWCUMCMVPW-UHFFFAOYSA-N phenyl n-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC=C1 SCWKRWCUMCMVPW-UHFFFAOYSA-N 0.000 claims 3
TYUMAKRCBIZVER-KRWDZBQOSA-N 4-(2-methoxyethylamino)-2-[4-[(2s)-2-(methylcarbamoyl)piperidin-1-yl]anilino]pyrimidine-5-carboxamide Chemical compound CNC(=O)[C@@H]1CCCCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCCOC)=N1 TYUMAKRCBIZVER-KRWDZBQOSA-N 0.000 claims 2
TUWUHYAHQFSQIB-UHFFFAOYSA-N 4-(cyclobutylamino)-2-(4-methylsulfonylanilino)pyrimidine-5-carboxamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1NC1=NC=C(C(N)=O)C(NC2CCC2)=N1 TUWUHYAHQFSQIB-UHFFFAOYSA-N 0.000 claims 2
WMXCQMPHRJRDHY-UHFFFAOYSA-N 4-(cyclobutylamino)-2-(4-piperazin-1-ylanilino)pyrimidine-5-carboxamide Chemical compound N1=C(NC2CCC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1N1CCNCC1 WMXCQMPHRJRDHY-UHFFFAOYSA-N 0.000 claims 2
RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 2
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
JKRJYAKPRGBXGS-UHFFFAOYSA-N 1-[4-[[5-carbamoyl-4-(cyclopropylamino)pyrimidin-2-yl]amino]phenyl]piperidine-4-carboxylic acid Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1N1CCC(C(O)=O)CC1 JKRJYAKPRGBXGS-UHFFFAOYSA-N 0.000 claims 1
OGQSAZZFJWBFAU-UHFFFAOYSA-N 2-(1,3-benzothiazol-5-ylamino)-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=C(NC=2C=C3N=CSC3=CC=2)N=C1NC1CC1 OGQSAZZFJWBFAU-UHFFFAOYSA-N 0.000 claims 1
OMQTXRAOVUDBME-UHFFFAOYSA-N 2-(2,1,3-benzothiadiazol-5-ylamino)-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=C(NC2=CC3=NSN=C3C=C2)N=C1NC1CC1 OMQTXRAOVUDBME-UHFFFAOYSA-N 0.000 claims 1
FQRZDZDDKDLPOZ-UHFFFAOYSA-N 2-(2h-benzotriazol-5-ylamino)-4-(cyclobutylamino)pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=C(NC=2C=C3NN=NC3=CC=2)N=C1NC1CCC1 FQRZDZDDKDLPOZ-UHFFFAOYSA-N 0.000 claims 1
LSKHRBUCLXYXIQ-UHFFFAOYSA-N 2-(2h-benzotriazol-5-ylamino)-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=C(NC=2C=C3NN=NC3=CC=2)N=C1NC1CC1 LSKHRBUCLXYXIQ-UHFFFAOYSA-N 0.000 claims 1
HUNGUDOJTFZWEZ-UHFFFAOYSA-N 2-(3-chloro-4-morpholin-4-ylanilino)-4-(cyclobutylamino)pyrimidine-5-carboxamide Chemical compound N1=C(NC2CCC2)C(C(=O)N)=CN=C1NC(C=C1Cl)=CC=C1N1CCOCC1 HUNGUDOJTFZWEZ-UHFFFAOYSA-N 0.000 claims 1
IRTSSLDSBHCJSQ-UHFFFAOYSA-N 2-(3h-benzimidazol-5-ylamino)-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=C(NC=2C=C3NC=NC3=CC=2)N=C1NC1CC1 IRTSSLDSBHCJSQ-UHFFFAOYSA-N 0.000 claims 1
VQIBVMLABQVROU-UHFFFAOYSA-N 2-(4-acetamidoanilino)-4-(cyclobutylamino)pyrimidine-5-carboxamide Chemical compound C1=CC(NC(=O)C)=CC=C1NC1=NC=C(C(N)=O)C(NC2CCC2)=N1 VQIBVMLABQVROU-UHFFFAOYSA-N 0.000 claims 1
ZCHSWTARBWRWDR-UHFFFAOYSA-N 2-(4-carbamoylanilino)-4-(2,2,2-trifluoroethylamino)pyrimidine-5-carboxamide Chemical compound C1=CC(C(=O)N)=CC=C1NC1=NC=C(C(N)=O)C(NCC(F)(F)F)=N1 ZCHSWTARBWRWDR-UHFFFAOYSA-N 0.000 claims 1
ARZOHYMLPRJOJP-UHFFFAOYSA-N 2-(4-carbamoylanilino)-4-(cyclobutylamino)pyrimidine-5-carboxamide Chemical compound C1=CC(C(=O)N)=CC=C1NC1=NC=C(C(N)=O)C(NC2CCC2)=N1 ARZOHYMLPRJOJP-UHFFFAOYSA-N 0.000 claims 1
GEMCNDWVKBDTCT-UHFFFAOYSA-N 2-(4-methoxyanilino)-4-(2,2,2-trifluoroethylamino)pyrimidine-5-carboxamide Chemical compound C1=CC(OC)=CC=C1NC1=NC=C(C(N)=O)C(NCC(F)(F)F)=N1 GEMCNDWVKBDTCT-UHFFFAOYSA-N 0.000 claims 1
SMNBTDKUMCQJIE-UHFFFAOYSA-N 2-(cyclobutylamino)pyrimidine-5-carboxamide Chemical compound N1=CC(C(=O)N)=CN=C1NC1CCC1 SMNBTDKUMCQJIE-UHFFFAOYSA-N 0.000 claims 1
LFJBIFUYVPMIPU-UHFFFAOYSA-N 2-[(3-chloro-2h-indazol-5-yl)amino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=C(NC=2C=C3C(Cl)=NNC3=CC=2)N=C1NC1CC1 LFJBIFUYVPMIPU-UHFFFAOYSA-N 0.000 claims 1
KAAMZEKNIGJFLE-UHFFFAOYSA-N 2-[(7-chloro-1h-indazol-6-yl)amino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=C(NC=2C(=C3NN=CC3=CC=2)Cl)N=C1NC1CC1 KAAMZEKNIGJFLE-UHFFFAOYSA-N 0.000 claims 1
NGCDJKRYFXYSQN-UHFFFAOYSA-N 2-[2-methyl-4-(4-methylsulfonylpiperazin-1-yl)anilino]-4-(2,2,2-trifluoroethylamino)pyrimidine-5-carboxamide Chemical compound CC1=CC(N2CCN(CC2)S(C)(=O)=O)=CC=C1NC1=NC=C(C(N)=O)C(NCC(F)(F)F)=N1 NGCDJKRYFXYSQN-UHFFFAOYSA-N 0.000 claims 1
ZIYCCEXTBSCMAH-UHFFFAOYSA-N 2-[4-(1-acetyl-3,6-dihydro-2h-pyridin-4-yl)anilino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound C1N(C(=O)C)CCC(C=2C=CC(NC=3N=C(NC4CC4)C(C(N)=O)=CN=3)=CC=2)=C1 ZIYCCEXTBSCMAH-UHFFFAOYSA-N 0.000 claims 1
BEEDZGOFSWTSCA-UHFFFAOYSA-N 2-[4-(1-acetylpiperidin-4-yl)anilino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCC1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 BEEDZGOFSWTSCA-UHFFFAOYSA-N 0.000 claims 1
DKUPSTAPGKQUGK-UHFFFAOYSA-N 2-[4-(2-cyanoethylsulfonyl)anilino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC1=CC=C(S(=O)(=O)CCC#N)C=C1 DKUPSTAPGKQUGK-UHFFFAOYSA-N 0.000 claims 1
CVIFEHXUMWPAKA-UHFFFAOYSA-N 2-[4-(2-hydroxyethylcarbamoyl)anilino]-4-(2,2,2-trifluoroethylamino)pyrimidine-5-carboxamide Chemical compound N1=C(NCC(F)(F)F)C(C(=O)N)=CN=C1NC1=CC=C(C(=O)NCCO)C=C1 CVIFEHXUMWPAKA-UHFFFAOYSA-N 0.000 claims 1
ZHPZPRXMMPRJOT-UHFFFAOYSA-N 2-[4-(2-methoxyethoxy)anilino]-4-(3-methylanilino)pyrimidine-5-carboxamide Chemical compound C1=CC(OCCOC)=CC=C1NC1=NC=C(C(N)=O)C(NC=2C=C(C)C=CC=2)=N1 ZHPZPRXMMPRJOT-UHFFFAOYSA-N 0.000 claims 1
MUAMPZBQBWJFFQ-UHFFFAOYSA-N 2-[4-(4-acetamidopiperidin-1-yl)anilino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound C1CC(NC(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 MUAMPZBQBWJFFQ-UHFFFAOYSA-N 0.000 claims 1
NAGPTSYMMKZNMG-UHFFFAOYSA-N 2-[4-(4-acetyl-1,4-diazepan-1-yl)anilino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 NAGPTSYMMKZNMG-UHFFFAOYSA-N 0.000 claims 1
PSSHWNRPVJAAGC-UHFFFAOYSA-N 2-[4-(4-acetyl-2-carbamoylpiperazin-1-yl)anilino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound NC(=O)C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 PSSHWNRPVJAAGC-UHFFFAOYSA-N 0.000 claims 1
BKXMDROHVJQXLF-UHFFFAOYSA-N 2-[4-(4-acetyl-2-oxopiperazin-1-yl)anilino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound O=C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 BKXMDROHVJQXLF-UHFFFAOYSA-N 0.000 claims 1
RMYPNAKAASQAFR-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)-3-fluoroanilino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C(=C1)F)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 RMYPNAKAASQAFR-UHFFFAOYSA-N 0.000 claims 1
WWFWIKFEJIUUSW-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(2,2,2-trifluoroethylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCC(F)(F)F)=N1 WWFWIKFEJIUUSW-UHFFFAOYSA-N 0.000 claims 1
FUDXGTLHDAKFNO-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(2-cyanoethylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCCC#N)=N1 FUDXGTLHDAKFNO-UHFFFAOYSA-N 0.000 claims 1
ACHNIWMUTPBTEZ-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(2-methoxyethylamino)pyrimidine-5-carboxamide Chemical compound C1=C(C(N)=O)C(NCCOC)=NC(NC=2C=CC(=CC=2)N2CCN(CC2)C(C)=O)=N1 ACHNIWMUTPBTEZ-UHFFFAOYSA-N 0.000 claims 1
AIAVDXRUEVJAEN-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(2-morpholin-4-ylethylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCCN2CCOCC2)=N1 AIAVDXRUEVJAEN-UHFFFAOYSA-N 0.000 claims 1
HLACSGCYKSELSD-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(3-hydroxypropylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCCCO)=N1 HLACSGCYKSELSD-UHFFFAOYSA-N 0.000 claims 1
FJUKIPMCEFHCDC-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(3-methoxyanilino)pyrimidine-5-carboxamide Chemical compound COC1=CC=CC(NC=2C(=CN=C(NC=3C=CC(=CC=3)N3CCN(CC3)C(C)=O)N=2)C(N)=O)=C1 FJUKIPMCEFHCDC-UHFFFAOYSA-N 0.000 claims 1
HWEJHLLMTLRJPQ-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(3-methoxypropylamino)pyrimidine-5-carboxamide Chemical compound C1=C(C(N)=O)C(NCCCOC)=NC(NC=2C=CC(=CC=2)N2CCN(CC2)C(C)=O)=N1 HWEJHLLMTLRJPQ-UHFFFAOYSA-N 0.000 claims 1
NUUXTUXBJCQMFL-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(3-methylanilino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC=2C=C(C)C=CC=2)=N1 NUUXTUXBJCQMFL-UHFFFAOYSA-N 0.000 claims 1
DJWHBWAXGQKJQW-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(4-hydroxybutylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCCCCO)=N1 DJWHBWAXGQKJQW-UHFFFAOYSA-N 0.000 claims 1
OOLHGIXQKHOIBU-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(benzylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCC=2C=CC=CC=2)=N1 OOLHGIXQKHOIBU-UHFFFAOYSA-N 0.000 claims 1
GQFDCZJGRAIYDY-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(butylamino)pyrimidine-5-carboxamide Chemical compound C1=C(C(N)=O)C(NCCCC)=NC(NC=2C=CC(=CC=2)N2CCN(CC2)C(C)=O)=N1 GQFDCZJGRAIYDY-UHFFFAOYSA-N 0.000 claims 1
ODOCPUAAXZORNM-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(cyanomethylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCC#N)=N1 ODOCPUAAXZORNM-UHFFFAOYSA-N 0.000 claims 1
PWUNLPDAMZWBHF-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(cyclopentylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CCCC2)=N1 PWUNLPDAMZWBHF-UHFFFAOYSA-N 0.000 claims 1
YMYMCGLMYUMRBN-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 YMYMCGLMYUMRBN-UHFFFAOYSA-N 0.000 claims 1
CSMVRSJEKXAWIG-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(ethylamino)pyrimidine-5-carboxamide Chemical compound C1=C(C(N)=O)C(NCC)=NC(NC=2C=CC(=CC=2)N2CCN(CC2)C(C)=O)=N1 CSMVRSJEKXAWIG-UHFFFAOYSA-N 0.000 claims 1
WSUQOCVWNARVBD-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(methylamino)pyrimidine-5-carboxamide Chemical compound C1=C(C(N)=O)C(NC)=NC(NC=2C=CC(=CC=2)N2CCN(CC2)C(C)=O)=N1 WSUQOCVWNARVBD-UHFFFAOYSA-N 0.000 claims 1
TXHWEXILMZNBJM-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(oxan-4-ylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CCOCC2)=N1 TXHWEXILMZNBJM-UHFFFAOYSA-N 0.000 claims 1
LEHYLXBIKVDZLA-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(prop-2-ynylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCC#C)=N1 LEHYLXBIKVDZLA-UHFFFAOYSA-N 0.000 claims 1
SVRYVBWAMMJFJT-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(propan-2-ylamino)pyrimidine-5-carboxamide Chemical compound C1=C(C(N)=O)C(NC(C)C)=NC(NC=2C=CC(=CC=2)N2CCN(CC2)C(C)=O)=N1 SVRYVBWAMMJFJT-UHFFFAOYSA-N 0.000 claims 1
HHQGTMZTKZVVHN-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(tert-butylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC(C)(C)C)=N1 HHQGTMZTKZVVHN-UHFFFAOYSA-N 0.000 claims 1
CIEZDTIPELGSDQ-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-[(1-carbamoylcyclopropyl)amino]pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2(CC2)C(N)=O)=N1 CIEZDTIPELGSDQ-UHFFFAOYSA-N 0.000 claims 1
HIHRKVOOMGCUMO-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-[(2-amino-2-oxoethyl)amino]pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCC(N)=O)=N1 HIHRKVOOMGCUMO-UHFFFAOYSA-N 0.000 claims 1
VCHOHJKMTRVCPL-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-[(2-oxo-3,4-dihydro-1h-quinolin-6-yl)amino]pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC=2C=C3CCC(=O)NC3=CC=2)=N1 VCHOHJKMTRVCPL-UHFFFAOYSA-N 0.000 claims 1
BQFJJLXJRXMRAY-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-[(3,4-dichlorophenyl)methylamino]pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCC=2C=C(Cl)C(Cl)=CC=2)=N1 BQFJJLXJRXMRAY-UHFFFAOYSA-N 0.000 claims 1
URSSCMDGVGWMCV-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-[(3-amino-3-oxopropyl)amino]pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCCC(N)=O)=N1 URSSCMDGVGWMCV-UHFFFAOYSA-N 0.000 claims 1
AIXZFNJDQBLOAN-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-[(4-amino-4-oxobutyl)amino]pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCCCC(N)=O)=N1 AIXZFNJDQBLOAN-UHFFFAOYSA-N 0.000 claims 1
KKDBOBCVCSYSOD-UHFFFAOYSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-[(4-chlorophenyl)methylamino]pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCC=2C=CC(Cl)=CC=2)=N1 KKDBOBCVCSYSOD-UHFFFAOYSA-N 0.000 claims 1
GYAKYIBOCULXFI-QGZVFWFLSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-[[(1r)-1-phenylethyl]amino]pyrimidine-5-carboxamide Chemical compound N([C@H](C)C=1C=CC=CC=1)C(C(=CN=1)C(N)=O)=NC=1NC(C=C1)=CC=C1N1CCN(C(C)=O)CC1 GYAKYIBOCULXFI-QGZVFWFLSA-N 0.000 claims 1
GZBHKAYXCQJJHF-IEBWSBKVSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-[[(1r,2r)-2-carbamoylcyclopentyl]amino]pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(N[C@H]2[C@@H](CCC2)C(N)=O)=N1 GZBHKAYXCQJJHF-IEBWSBKVSA-N 0.000 claims 1
SFSLQICHBBEJQS-NVXWUHKLSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-[[(1r,3r)-3-carbamoylcyclopentyl]amino]pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(N[C@H]2C[C@@H](CC2)C(N)=O)=N1 SFSLQICHBBEJQS-NVXWUHKLSA-N 0.000 claims 1
GYAKYIBOCULXFI-KRWDZBQOSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-[[(1s)-1-phenylethyl]amino]pyrimidine-5-carboxamide Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(C(=CN=1)C(N)=O)=NC=1NC(C=C1)=CC=C1N1CCN(C(C)=O)CC1 GYAKYIBOCULXFI-KRWDZBQOSA-N 0.000 claims 1
LJBRYSDQEXGEDY-CYBMUJFWSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-[[(2r)-1-hydroxypropan-2-yl]amino]pyrimidine-5-carboxamide Chemical compound C1=C(C(N)=O)C(N[C@@H](CO)C)=NC(NC=2C=CC(=CC=2)N2CCN(CC2)C(C)=O)=N1 LJBRYSDQEXGEDY-CYBMUJFWSA-N 0.000 claims 1
QDYPBTWFTIADRM-MRXNPFEDSA-N 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-[[(2r)-2,3-dihydroxypropyl]amino]pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC[C@@H](O)CO)=N1 QDYPBTWFTIADRM-MRXNPFEDSA-N 0.000 claims 1
MBZPIYCLHFTESL-UHFFFAOYSA-N 2-[4-(4-acetylpiperazine-1-carbonyl)anilino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 MBZPIYCLHFTESL-UHFFFAOYSA-N 0.000 claims 1
YSWXQLFCNONZOX-UHFFFAOYSA-N 2-[4-(4-carbamoylpiperazin-1-yl)anilino]-4-(cyclobutylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)N)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CCC2)=N1 YSWXQLFCNONZOX-UHFFFAOYSA-N 0.000 claims 1
HOVAVHGVEAOMAO-UHFFFAOYSA-N 2-[4-(4-carbamoylpiperazin-1-yl)anilino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)N)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 HOVAVHGVEAOMAO-UHFFFAOYSA-N 0.000 claims 1
YSRDYJWFCIHHCN-UHFFFAOYSA-N 2-[4-(4-carbamoylpiperidin-1-yl)anilino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound C1CC(C(=O)N)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 YSRDYJWFCIHHCN-UHFFFAOYSA-N 0.000 claims 1
DNHQTNICFICFCV-UHFFFAOYSA-N 2-[4-(4-methylpiperazin-1-yl)anilino]pyrimidine-5-carboxamide Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C=N1 DNHQTNICFICFCV-UHFFFAOYSA-N 0.000 claims 1
INJXCQQITMUACY-UHFFFAOYSA-N 2-[4-(5,6-dihydro-4h-1,3-oxazin-2-yl)anilino]-4-(2,2,2-trifluoroethylamino)pyrimidine-5-carboxamide Chemical compound N1=C(NCC(F)(F)F)C(C(=O)N)=CN=C1NC1=CC=C(C=2OCCCN=2)C=C1 INJXCQQITMUACY-UHFFFAOYSA-N 0.000 claims 1
NYLYRELUOWSPLX-UHFFFAOYSA-N 2-[4-(cyclobutylcarbamoyl)anilino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1C(=O)NC1CCC1 NYLYRELUOWSPLX-UHFFFAOYSA-N 0.000 claims 1
TWKPUJBGKBUEJI-OAHLLOKOSA-N 2-[4-[(2r)-2-carbamoylpyrrolidin-1-yl]anilino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound NC(=O)[C@H]1CCCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 TWKPUJBGKBUEJI-OAHLLOKOSA-N 0.000 claims 1
ATMMUPGLPOUHAF-GFCCVEGCSA-N 2-[4-[(2r)-2-methyl-4-methylsulfonylpiperazin-1-yl]anilino]-4-(2,2,2-trifluoroethylamino)pyrimidine-5-carboxamide Chemical compound C[C@@H]1CN(S(C)(=O)=O)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCC(F)(F)F)=N1 ATMMUPGLPOUHAF-GFCCVEGCSA-N 0.000 claims 1
NQMKSQSMVGAAFH-GFCCVEGCSA-N 2-[4-[(2r)-4-acetyl-2-methylpiperazin-1-yl]anilino]-4-(2,2,2-trifluoroethylamino)pyrimidine-5-carboxamide Chemical compound C[C@@H]1CN(C(C)=O)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCC(F)(F)F)=N1 NQMKSQSMVGAAFH-GFCCVEGCSA-N 0.000 claims 1
SHKPAGCKSWICRR-CYBMUJFWSA-N 2-[4-[(2r)-4-acetyl-2-methylpiperazin-1-yl]anilino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound C[C@@H]1CN(C(C)=O)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 SHKPAGCKSWICRR-CYBMUJFWSA-N 0.000 claims 1
SWCJUXJNIUUXRJ-INIZCTEOSA-N 2-[4-[(2s)-2-(dimethylcarbamoyl)piperidin-1-yl]anilino]-4-(2,2,2-trifluoroethylamino)pyrimidine-5-carboxamide Chemical compound CN(C)C(=O)[C@@H]1CCCCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCC(F)(F)F)=N1 SWCJUXJNIUUXRJ-INIZCTEOSA-N 0.000 claims 1
CGDDVVJZSTWXJQ-KRWDZBQOSA-N 2-[4-[(2s)-2-(methylcarbamoyl)piperidin-1-yl]anilino]-4-(propan-2-ylamino)pyrimidine-5-carboxamide Chemical compound CNC(=O)[C@@H]1CCCCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC(C)C)=N1 CGDDVVJZSTWXJQ-KRWDZBQOSA-N 0.000 claims 1
BSWGUAZLBKVXTK-FQEVSTJZSA-N 2-[4-[(2s)-2-(methylcarbamoyl)piperidin-1-yl]anilino]-4-[(2,3,6-trifluorophenyl)methylamino]pyrimidine-5-carboxamide Chemical compound CNC(=O)[C@@H]1CCCCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCC=2C(=C(F)C=CC=2F)F)=N1 BSWGUAZLBKVXTK-FQEVSTJZSA-N 0.000 claims 1
QRXKSMOMCMQPTR-AWEZNQCLSA-N 2-[4-[(2s)-2-carbamoylazetidin-1-yl]anilino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound NC(=O)[C@@H]1CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 QRXKSMOMCMQPTR-AWEZNQCLSA-N 0.000 claims 1
CXKIXVZQPJZZKX-AWEZNQCLSA-N 2-[4-[(2s)-2-carbamoylpiperidin-1-yl]anilino]-4-(2,2,2-trifluoroethylamino)pyrimidine-5-carboxamide Chemical compound NC(=O)[C@@H]1CCCCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCC(F)(F)F)=N1 CXKIXVZQPJZZKX-AWEZNQCLSA-N 0.000 claims 1
TWKPUJBGKBUEJI-HNNXBMFYSA-N 2-[4-[(2s)-2-carbamoylpyrrolidin-1-yl]anilino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound NC(=O)[C@@H]1CCCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 TWKPUJBGKBUEJI-HNNXBMFYSA-N 0.000 claims 1
ATMMUPGLPOUHAF-LBPRGKRZSA-N 2-[4-[(2s)-2-methyl-4-methylsulfonylpiperazin-1-yl]anilino]-4-(2,2,2-trifluoroethylamino)pyrimidine-5-carboxamide Chemical compound C[C@H]1CN(S(C)(=O)=O)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCC(F)(F)F)=N1 ATMMUPGLPOUHAF-LBPRGKRZSA-N 0.000 claims 1
NQMKSQSMVGAAFH-LBPRGKRZSA-N 2-[4-[(2s)-4-acetyl-2-methylpiperazin-1-yl]anilino]-4-(2,2,2-trifluoroethylamino)pyrimidine-5-carboxamide Chemical compound C[C@H]1CN(C(C)=O)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCC(F)(F)F)=N1 NQMKSQSMVGAAFH-LBPRGKRZSA-N 0.000 claims 1
HSEQRWWZDPZONI-ZDUSSCGKSA-N 2-[4-[(2s)-4-cyclopropylsulfonyl-2-methylpiperazin-1-yl]anilino]-4-(2,2,2-trifluoroethylamino)pyrimidine-5-carboxamide Chemical compound C([C@@H]1C)N(S(=O)(=O)C2CC2)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCC(F)(F)F)=N1 HSEQRWWZDPZONI-ZDUSSCGKSA-N 0.000 claims 1
FSMGPSUWQGKLIL-ZDUSSCGKSA-N 2-[4-[(2s)-4-ethylsulfonyl-2-methylpiperazin-1-yl]anilino]-4-(2,2,2-trifluoroethylamino)pyrimidine-5-carboxamide Chemical compound C[C@H]1CN(S(=O)(=O)CC)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCC(F)(F)F)=N1 FSMGPSUWQGKLIL-ZDUSSCGKSA-N 0.000 claims 1
NUPJPBPKMJNGQP-HIFRSBDPSA-N 2-[4-[(2s,4r)-2-carbamoyl-4-hydroxypyrrolidin-1-yl]anilino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound NC(=O)[C@@H]1C[C@@H](O)CN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 NUPJPBPKMJNGQP-HIFRSBDPSA-N 0.000 claims 1
NUPJPBPKMJNGQP-ZFWWWQNUSA-N 2-[4-[(2s,4s)-2-carbamoyl-4-hydroxypyrrolidin-1-yl]anilino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound NC(=O)[C@@H]1C[C@H](O)CN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 NUPJPBPKMJNGQP-ZFWWWQNUSA-N 0.000 claims 1
QXWGPDDNOFUMIM-GFCCVEGCSA-N 2-[4-[(3r)-3-(methylcarbamoyl)piperidin-1-yl]anilino]-4-(2,2,2-trifluoroethylamino)pyrimidine-5-carboxamide Chemical compound C1[C@H](C(=O)NC)CCCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCC(F)(F)F)=N1 QXWGPDDNOFUMIM-GFCCVEGCSA-N 0.000 claims 1
YHIJFHJJEXNYDC-LLVKDONJSA-N 2-[4-[(3r)-3-carbamoylpiperidin-1-yl]anilino]-4-(2,2,2-trifluoroethylamino)pyrimidine-5-carboxamide Chemical compound C1[C@H](C(=O)N)CCCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCC(F)(F)F)=N1 YHIJFHJJEXNYDC-LLVKDONJSA-N 0.000 claims 1
UNRTWZKXADNVLM-GFCCVEGCSA-N 2-[4-[(3r)-3-carbamoylpiperidin-1-yl]anilino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound C1[C@H](C(=O)N)CCCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 UNRTWZKXADNVLM-GFCCVEGCSA-N 0.000 claims 1
NEXZDOALKCAQGP-CYBMUJFWSA-N 2-[4-[(3r)-4-acetyl-3-methylpiperazin-1-yl]anilino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(C)=O)[C@H](C)CN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 NEXZDOALKCAQGP-CYBMUJFWSA-N 0.000 claims 1
UNRTWZKXADNVLM-LBPRGKRZSA-N 2-[4-[(3s)-3-carbamoylpiperidin-1-yl]anilino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound C1[C@@H](C(=O)N)CCCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 UNRTWZKXADNVLM-LBPRGKRZSA-N 0.000 claims 1
ZMDGDFZQHLEMGE-UHFFFAOYSA-N 2-[4-[4-(aminomethyl)piperidin-1-yl]anilino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound C1CC(CN)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 ZMDGDFZQHLEMGE-UHFFFAOYSA-N 0.000 claims 1
HKEWKAKSJMXONQ-UHFFFAOYSA-N 2-[4-[4-acetyl-2-(methylcarbamoyl)piperazin-1-yl]anilino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound CNC(=O)C1CN(C(C)=O)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 HKEWKAKSJMXONQ-UHFFFAOYSA-N 0.000 claims 1
ODONSQFVCCSVME-ZDUSSCGKSA-N 2-[4-[[(2s)-1-amino-3-methyl-1-oxobutan-2-yl]amino]anilino]-4-(2,2,2-trifluoroethylamino)pyrimidine-5-carboxamide Chemical compound C1=CC(N[C@@H](C(C)C)C(N)=O)=CC=C1NC1=NC=C(C(N)=O)C(NCC(F)(F)F)=N1 ODONSQFVCCSVME-ZDUSSCGKSA-N 0.000 claims 1
CKBFCBOIEWIJNQ-UHFFFAOYSA-N 2-[4-[acetyl(methyl)amino]-3-chloroanilino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound C1=C(Cl)C(N(C(C)=O)C)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 CKBFCBOIEWIJNQ-UHFFFAOYSA-N 0.000 claims 1
XNGHEAQNWZTIEZ-UHFFFAOYSA-N 2-[4-[acetyl(methyl)amino]anilino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound C1=CC(N(C(C)=O)C)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 XNGHEAQNWZTIEZ-UHFFFAOYSA-N 0.000 claims 1
DDDRCWVBDHBPIJ-UHFFFAOYSA-N 2-[4-[carbamoyl(methyl)amino]anilino]-4-(cyclobutylamino)pyrimidine-5-carboxamide Chemical compound C1=CC(N(C(N)=O)C)=CC=C1NC1=NC=C(C(N)=O)C(NC2CCC2)=N1 DDDRCWVBDHBPIJ-UHFFFAOYSA-N 0.000 claims 1
PTUIOQXDADQRPN-UHFFFAOYSA-N 2-[4-[carbamoyl(methyl)amino]anilino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound C1=CC(N(C(N)=O)C)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 PTUIOQXDADQRPN-UHFFFAOYSA-N 0.000 claims 1
FIFSVDLRHHJSDN-UHFFFAOYSA-N 2-[4-[cyclobutyl(methyl)carbamoyl]anilino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound C=1C=C(NC=2N=C(NC3CC3)C(C(N)=O)=CN=2)C=CC=1C(=O)N(C)C1CCC1 FIFSVDLRHHJSDN-UHFFFAOYSA-N 0.000 claims 1
OSDKWHXTHRSYFE-UHFFFAOYSA-N 2-[[1-(2-amino-2-oxoethyl)indazol-6-yl]amino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound C1=C2N(CC(=O)N)N=CC2=CC=C1NC(N=1)=NC=C(C(N)=O)C=1NC1CC1 OSDKWHXTHRSYFE-UHFFFAOYSA-N 0.000 claims 1
SMHAOHOUHZPHET-UHFFFAOYSA-N 2-[[6-(4-acetylpiperazin-1-yl)pyridin-3-yl]amino]-4-(2,2,2-trifluoroethylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(N=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCC(F)(F)F)=N1 SMHAOHOUHZPHET-UHFFFAOYSA-N 0.000 claims 1
AKQVRZFPXRHIKV-UHFFFAOYSA-N 2-[[6-(4-acetylpiperazin-1-yl)pyridin-3-yl]amino]-4-(cyclopropylamino)pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)C)CCN1C(N=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 AKQVRZFPXRHIKV-UHFFFAOYSA-N 0.000 claims 1
FEOZAUOLCXCHGY-UHFFFAOYSA-N 2-anilino-4-(cyclobutylamino)pyrimidine-5-carboxamide Chemical compound N1=C(NC2CCC2)C(C(=O)N)=CN=C1NC1=CC=CC=C1 FEOZAUOLCXCHGY-UHFFFAOYSA-N 0.000 claims 1
NFRAMAAXUSYSSF-UHFFFAOYSA-N 4-(3,5-dimethylanilino)-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]pyrimidine-5-carboxamide Chemical compound CC1=CC(C)=CC(NC=2C(=CN=C(NC=3C=CC(OCCN4CCCC4)=CC=3)N=2)C(N)=O)=C1 NFRAMAAXUSYSSF-UHFFFAOYSA-N 0.000 claims 1
OZXXLLYFWJXRPD-UHFFFAOYSA-N 4-(3-methylanilino)-2-[4-(2-morpholin-4-yl-2-oxoethoxy)anilino]pyrimidine-5-carboxamide Chemical compound CC1=CC=CC(NC=2C(=CN=C(NC=3C=CC(OCC(=O)N4CCOCC4)=CC=3)N=2)C(N)=O)=C1 OZXXLLYFWJXRPD-UHFFFAOYSA-N 0.000 claims 1
YXDONSSJZFMDIP-UHFFFAOYSA-N 4-(3-methylanilino)-2-[4-(2-morpholin-4-ylethoxy)anilino]pyrimidine-5-carboxamide Chemical compound CC1=CC=CC(NC=2C(=CN=C(NC=3C=CC(OCCN4CCOCC4)=CC=3)N=2)C(N)=O)=C1 YXDONSSJZFMDIP-UHFFFAOYSA-N 0.000 claims 1
LUCQPJRATKKJBO-UHFFFAOYSA-N 4-(4-methylsulfonylanilino)-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]pyrimidine-5-carboxamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1NC1=NC(NC=2C=CC(OCCN3CCCC3)=CC=2)=NC=C1C(N)=O LUCQPJRATKKJBO-UHFFFAOYSA-N 0.000 claims 1
QVYQEZQWYDXQOS-UHFFFAOYSA-N 4-(benzylamino)-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]pyrimidine-5-carboxamide Chemical compound N1=C(NCC=2C=CC=CC=2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1OCCN1CCCC1 QVYQEZQWYDXQOS-UHFFFAOYSA-N 0.000 claims 1
HPLUDPNDPNMVDZ-NRFANRHFSA-N 4-(benzylamino)-2-[4-[(2s)-2-(methylcarbamoyl)piperidin-1-yl]anilino]pyrimidine-5-carboxamide Chemical compound CNC(=O)[C@@H]1CCCCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCC=2C=CC=CC=2)=N1 HPLUDPNDPNMVDZ-NRFANRHFSA-N 0.000 claims 1
NVUDKPWWCKXFSL-UHFFFAOYSA-N 4-(cyclobutylamino)-2-(2,3-dihydro-1,4-benzodioxin-6-ylamino)pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=C(NC=2C=C3OCCOC3=CC=2)N=C1NC1CCC1 NVUDKPWWCKXFSL-UHFFFAOYSA-N 0.000 claims 1
CKXXNGXJRXNCJN-UHFFFAOYSA-N 4-(cyclobutylamino)-2-(4-piperidin-1-ylanilino)pyrimidine-5-carboxamide Chemical compound N1=C(NC2CCC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1N1CCCCC1 CKXXNGXJRXNCJN-UHFFFAOYSA-N 0.000 claims 1
RRGRXLIJXLRXGH-UHFFFAOYSA-N 4-(cyclobutylamino)-2-(4-sulfamoylanilino)pyrimidine-5-carboxamide Chemical compound N1=C(NC2CCC2)C(C(=O)N)=CN=C1NC1=CC=C(S(N)(=O)=O)C=C1 RRGRXLIJXLRXGH-UHFFFAOYSA-N 0.000 claims 1
RKBLDEARFOBJNW-UHFFFAOYSA-N 4-(cyclobutylamino)-2-(imidazo[1,2-a]pyridin-6-ylamino)pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=C(NC2=CN3C=CN=C3C=C2)N=C1NC1CCC1 RKBLDEARFOBJNW-UHFFFAOYSA-N 0.000 claims 1
SMHCCPYPLZGWDU-UHFFFAOYSA-N 4-(cyclobutylamino)-2-[(2,2,4-trimethyl-3-oxo-1,4-benzoxazin-7-yl)amino]pyrimidine-5-carboxamide Chemical compound C=1C=C2N(C)C(=O)C(C)(C)OC2=CC=1NC(N=1)=NC=C(C(N)=O)C=1NC1CCC1 SMHCCPYPLZGWDU-UHFFFAOYSA-N 0.000 claims 1
MKDPVDQDYCEBEI-UHFFFAOYSA-N 4-(cyclobutylamino)-2-[(2,2-difluoro-1,3-benzodioxol-5-yl)amino]pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=C(NC=2C=C3OC(F)(F)OC3=CC=2)N=C1NC1CCC1 MKDPVDQDYCEBEI-UHFFFAOYSA-N 0.000 claims 1
QDRZJOHUFIAAAV-UHFFFAOYSA-N 4-(cyclobutylamino)-2-[(2-oxo-1,3-dihydroindol-5-yl)amino]pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=C(NC=2C=C3CC(=O)NC3=CC=2)N=C1NC1CCC1 QDRZJOHUFIAAAV-UHFFFAOYSA-N 0.000 claims 1
CHKKNVVDPNMEIM-UHFFFAOYSA-N 4-(cyclobutylamino)-2-[(2-oxo-3h-1-benzofuran-5-yl)amino]pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=C(NC=2C=C3CC(=O)OC3=CC=2)N=C1NC1CCC1 CHKKNVVDPNMEIM-UHFFFAOYSA-N 0.000 claims 1
NLKITEMJABKGDY-UHFFFAOYSA-N 4-(cyclobutylamino)-2-[(3-oxo-4h-1,4-benzoxazin-6-yl)amino]pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=C(NC=2C=C3NC(=O)COC3=CC=2)N=C1NC1CCC1 NLKITEMJABKGDY-UHFFFAOYSA-N 0.000 claims 1
FIKXJMWFRVFVTL-UHFFFAOYSA-N 4-(cyclobutylamino)-2-[4-(3,3-difluoropiperidin-1-yl)anilino]pyrimidine-5-carboxamide Chemical compound N1=C(NC2CCC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1N1CCCC(F)(F)C1 FIKXJMWFRVFVTL-UHFFFAOYSA-N 0.000 claims 1
ZROBTLDDRUTGQJ-UHFFFAOYSA-N 4-(cyclobutylamino)-2-[4-(3,3-difluoropyrrolidin-1-yl)anilino]pyrimidine-5-carboxamide Chemical compound N1=C(NC2CCC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1N1CCC(F)(F)C1 ZROBTLDDRUTGQJ-UHFFFAOYSA-N 0.000 claims 1
HBZNWODJMUPRHC-UHFFFAOYSA-N 4-(cyclobutylamino)-2-[4-(4,4-difluoropiperidin-1-yl)anilino]pyrimidine-5-carboxamide Chemical compound N1=C(NC2CCC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1N1CCC(F)(F)CC1 HBZNWODJMUPRHC-UHFFFAOYSA-N 0.000 claims 1
KCQOFXUYPVKJPS-UHFFFAOYSA-N 4-(cyclobutylamino)-2-[4-(4-fluoropiperidin-1-yl)anilino]pyrimidine-5-carboxamide Chemical compound N1=C(NC2CCC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1N1CCC(F)CC1 KCQOFXUYPVKJPS-UHFFFAOYSA-N 0.000 claims 1
HRXZHBOWBDSXDE-UHFFFAOYSA-N 4-(cyclobutylamino)-2-[4-(4-hydroxypiperidin-1-yl)anilino]pyrimidine-5-carboxamide Chemical compound N1=C(NC2CCC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1N1CCC(O)CC1 HRXZHBOWBDSXDE-UHFFFAOYSA-N 0.000 claims 1
AHMAJTHJFJZADS-UHFFFAOYSA-N 4-(cyclobutylamino)-2-[4-(4-methylpiperazin-1-yl)anilino]pyrimidine-5-carboxamide Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CCC2)=N1 AHMAJTHJFJZADS-UHFFFAOYSA-N 0.000 claims 1
JKSCADGEJBGYAM-UHFFFAOYSA-N 4-(cyclobutylamino)-2-[4-(4-methylsulfonylpiperazin-1-yl)anilino]pyrimidine-5-carboxamide Chemical compound C1CN(S(=O)(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CCC2)=N1 JKSCADGEJBGYAM-UHFFFAOYSA-N 0.000 claims 1
GPOQKVUJOPWFGH-UHFFFAOYSA-N 4-(cyclobutylamino)-2-[4-(diethylamino)anilino]pyrimidine-5-carboxamide Chemical compound C1=CC(N(CC)CC)=CC=C1NC1=NC=C(C(N)=O)C(NC2CCC2)=N1 GPOQKVUJOPWFGH-UHFFFAOYSA-N 0.000 claims 1
ROCDTLVQIVIKFA-UHFFFAOYSA-N 4-(cyclobutylamino)-2-[4-(dimethylamino)anilino]pyrimidine-5-carboxamide Chemical compound C1=CC(N(C)C)=CC=C1NC1=NC=C(C(N)=O)C(NC2CCC2)=N1 ROCDTLVQIVIKFA-UHFFFAOYSA-N 0.000 claims 1
TWRNXCQFXIJECQ-UHFFFAOYSA-N 4-(cyclobutylamino)-2-[4-(dimethylcarbamoyl)anilino]pyrimidine-5-carboxamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1NC1=NC=C(C(N)=O)C(NC2CCC2)=N1 TWRNXCQFXIJECQ-UHFFFAOYSA-N 0.000 claims 1
FTLPLWJSEFREBY-UHFFFAOYSA-N 4-(cyclobutylamino)-2-[4-(dimethylsulfamoyl)anilino]pyrimidine-5-carboxamide Chemical compound C1=CC(S(=O)(=O)N(C)C)=CC=C1NC1=NC=C(C(N)=O)C(NC2CCC2)=N1 FTLPLWJSEFREBY-UHFFFAOYSA-N 0.000 claims 1
SFFPIQKRDVRQPY-UHFFFAOYSA-N 4-(cyclobutylamino)-2-[4-(methylcarbamoyl)anilino]pyrimidine-5-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1NC1=NC=C(C(N)=O)C(NC2CCC2)=N1 SFFPIQKRDVRQPY-UHFFFAOYSA-N 0.000 claims 1
MHGKIMUPXQVGQL-UHFFFAOYSA-N 4-(cyclobutylamino)-2-[4-(trifluoromethoxy)anilino]pyrimidine-5-carboxamide Chemical compound N1=C(NC2CCC2)C(C(=O)N)=CN=C1NC1=CC=C(OC(F)(F)F)C=C1 MHGKIMUPXQVGQL-UHFFFAOYSA-N 0.000 claims 1
FKHNCBAAOWRPTH-UHFFFAOYSA-N 4-(cyclobutylamino)-2-[4-[4-(2-hydroxyethyl)piperazin-1-yl]anilino]pyrimidine-5-carboxamide Chemical compound N1=C(NC2CCC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1N1CCN(CCO)CC1 FKHNCBAAOWRPTH-UHFFFAOYSA-N 0.000 claims 1
RURSWQQSZWSTMV-UHFFFAOYSA-N 4-(cyclobutylamino)-2-[4-[4-(dimethylcarbamoyl)piperazin-1-yl]anilino]pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)N(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CCC2)=N1 RURSWQQSZWSTMV-UHFFFAOYSA-N 0.000 claims 1
VLYZXKNIUUTHRF-UHFFFAOYSA-N 4-(cyclobutylamino)-2-[4-[4-(dimethylcarbamoyl)piperidin-1-yl]anilino]pyrimidine-5-carboxamide Chemical compound C1CC(C(=O)N(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CCC2)=N1 VLYZXKNIUUTHRF-UHFFFAOYSA-N 0.000 claims 1
GYBIDWVELLPIOZ-UHFFFAOYSA-N 4-(cyclobutylamino)-2-[4-[4-(methylcarbamoyl)piperidin-1-yl]anilino]pyrimidine-5-carboxamide Chemical compound C1CC(C(=O)NC)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CCC2)=N1 GYBIDWVELLPIOZ-UHFFFAOYSA-N 0.000 claims 1
DJRMNLGNKKXXAY-IBGZPJMESA-N 4-(cyclopentylamino)-2-[4-[(2s)-2-(methylcarbamoyl)piperidin-1-yl]anilino]pyrimidine-5-carboxamide Chemical compound CNC(=O)[C@@H]1CCCCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CCCC2)=N1 DJRMNLGNKKXXAY-IBGZPJMESA-N 0.000 claims 1
OLNFMELGPAKTSL-UHFFFAOYSA-N 4-(cyclopropylamino)-2-(1h-indazol-5-ylamino)pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=C(NC=2C=C3C=NNC3=CC=2)N=C1NC1CC1 OLNFMELGPAKTSL-UHFFFAOYSA-N 0.000 claims 1
NNOYIZJBDKGRNN-UHFFFAOYSA-N 4-(cyclopropylamino)-2-(1h-indazol-6-ylamino)pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=C(NC=2C=C3NN=CC3=CC=2)N=C1NC1CC1 NNOYIZJBDKGRNN-UHFFFAOYSA-N 0.000 claims 1
YKYVBDDWMGCDGK-UHFFFAOYSA-N 4-(cyclopropylamino)-2-(1h-indol-5-ylamino)pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=C(NC=2C=C3C=CNC3=CC=2)N=C1NC1CC1 YKYVBDDWMGCDGK-UHFFFAOYSA-N 0.000 claims 1
UELXDLIIGONZKC-UHFFFAOYSA-N 4-(cyclopropylamino)-2-(1h-indol-6-ylamino)pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=C(NC=2C=C3NC=CC3=CC=2)N=C1NC1CC1 UELXDLIIGONZKC-UHFFFAOYSA-N 0.000 claims 1
CPEHPPLOCZRAMK-UHFFFAOYSA-N 4-(cyclopropylamino)-2-(2,3-dihydro-1,4-benzodioxin-6-ylamino)pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=C(NC=2C=C3OCCOC3=CC=2)N=C1NC1CC1 CPEHPPLOCZRAMK-UHFFFAOYSA-N 0.000 claims 1
SVCUIRPPYPPRFV-UHFFFAOYSA-N 4-(cyclopropylamino)-2-(4-ethoxyanilino)pyrimidine-5-carboxamide Chemical compound C1=CC(OCC)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 SVCUIRPPYPPRFV-UHFFFAOYSA-N 0.000 claims 1
WVOHPIDDYYHFEL-UHFFFAOYSA-N 4-(cyclopropylamino)-2-(4-ethylsulfonylanilino)pyrimidine-5-carboxamide Chemical compound C1=CC(S(=O)(=O)CC)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 WVOHPIDDYYHFEL-UHFFFAOYSA-N 0.000 claims 1
QCCSUGVDYGNJIR-UHFFFAOYSA-N 4-(cyclopropylamino)-2-(4-formamido-3-hydroxyanilino)pyrimidine-5-carboxamide Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC1=CC=C(NC=O)C(O)=C1 QCCSUGVDYGNJIR-UHFFFAOYSA-N 0.000 claims 1
BGGSICXOTGWBQN-UHFFFAOYSA-N 4-(cyclopropylamino)-2-(4-methylsulfanylanilino)pyrimidine-5-carboxamide Chemical compound C1=CC(SC)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 BGGSICXOTGWBQN-UHFFFAOYSA-N 0.000 claims 1
UZZAAUCYLNTAHC-UHFFFAOYSA-N 4-(cyclopropylamino)-2-(4-methylsulfinylanilino)pyrimidine-5-carboxamide Chemical compound C1=CC(S(=O)C)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 UZZAAUCYLNTAHC-UHFFFAOYSA-N 0.000 claims 1
DVAUUTROCVYAHA-UHFFFAOYSA-N 4-(cyclopropylamino)-2-(4-methylsulfonylanilino)pyrimidine-5-carboxamide Chemical compound C1=CC(S(=O)(=O)C)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 DVAUUTROCVYAHA-UHFFFAOYSA-N 0.000 claims 1
UTFFPNWHNPJSGV-UHFFFAOYSA-N 4-(cyclopropylamino)-2-(4-phenoxyanilino)pyrimidine-5-carboxamide Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1OC1=CC=CC=C1 UTFFPNWHNPJSGV-UHFFFAOYSA-N 0.000 claims 1
NSAHYWMPAZHGOK-UHFFFAOYSA-N 4-(cyclopropylamino)-2-(4-piperazin-1-ylanilino)pyrimidine-5-carboxamide Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1N1CCNCC1 NSAHYWMPAZHGOK-UHFFFAOYSA-N 0.000 claims 1
QXGVBTOUSGKQAJ-UHFFFAOYSA-N 4-(cyclopropylamino)-2-(4-piperidin-1-ylanilino)pyrimidine-5-carboxamide Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1N1CCCCC1 QXGVBTOUSGKQAJ-UHFFFAOYSA-N 0.000 claims 1
LGAMPPSYXHWVLG-UHFFFAOYSA-N 4-(cyclopropylamino)-2-(4-pyrazol-1-ylanilino)pyrimidine-5-carboxamide Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1N1C=CC=N1 LGAMPPSYXHWVLG-UHFFFAOYSA-N 0.000 claims 1
XUPIGDKZPIRZON-UHFFFAOYSA-N 4-(cyclopropylamino)-2-(4-pyridin-2-ylanilino)pyrimidine-5-carboxamide Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1C1=CC=CC=N1 XUPIGDKZPIRZON-UHFFFAOYSA-N 0.000 claims 1
YRQVHWVDLNVWHM-UHFFFAOYSA-N 4-(cyclopropylamino)-2-(4-pyridin-3-ylanilino)pyrimidine-5-carboxamide Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1C1=CC=CN=C1 YRQVHWVDLNVWHM-UHFFFAOYSA-N 0.000 claims 1
JTLMTZOHUOZKJJ-UHFFFAOYSA-N 4-(cyclopropylamino)-2-(4-pyridin-3-yloxyanilino)pyrimidine-5-carboxamide Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1OC1=CC=CN=C1 JTLMTZOHUOZKJJ-UHFFFAOYSA-N 0.000 claims 1
CIBLZKYVDWLHPP-UHFFFAOYSA-N 4-(cyclopropylamino)-2-(4-sulfamoylanilino)pyrimidine-5-carboxamide Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC1=CC=C(S(N)(=O)=O)C=C1 CIBLZKYVDWLHPP-UHFFFAOYSA-N 0.000 claims 1
BDTYDFBJDBQJSL-UHFFFAOYSA-N 4-(cyclopropylamino)-2-(4-thiophen-2-ylanilino)pyrimidine-5-carboxamide Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1C1=CC=CS1 BDTYDFBJDBQJSL-UHFFFAOYSA-N 0.000 claims 1
JKWQBSBQOZCQNS-UHFFFAOYSA-N 4-(cyclopropylamino)-2-(imidazo[1,2-a]pyridin-6-ylamino)pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=C(NC2=CN3C=CN=C3C=C2)N=C1NC1CC1 JKWQBSBQOZCQNS-UHFFFAOYSA-N 0.000 claims 1
LPBGPDKSWUGPBT-UHFFFAOYSA-N 4-(cyclopropylamino)-2-(quinolin-6-ylamino)pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=C(NC=2C=C3C=CC=NC3=CC=2)N=C1NC1CC1 LPBGPDKSWUGPBT-UHFFFAOYSA-N 0.000 claims 1
VCFNFSZYMKUDDS-UHFFFAOYSA-N 4-(cyclopropylamino)-2-(quinoxalin-6-ylamino)pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=C(NC=2C=C3N=CC=NC3=CC=2)N=C1NC1CC1 VCFNFSZYMKUDDS-UHFFFAOYSA-N 0.000 claims 1
DLHNBMFZYWTGRP-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[(2,2-difluoro-1,3-benzodioxol-5-yl)amino]pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=C(NC=2C=C3OC(F)(F)OC3=CC=2)N=C1NC1CC1 DLHNBMFZYWTGRP-UHFFFAOYSA-N 0.000 claims 1
XVYARVQKXOJAHD-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[(2-methyl-1,3-benzothiazol-5-yl)amino]pyrimidine-5-carboxamide Chemical compound C=1C=C2SC(C)=NC2=CC=1NC(N=1)=NC=C(C(N)=O)C=1NC1CC1 XVYARVQKXOJAHD-UHFFFAOYSA-N 0.000 claims 1
VLNMBPSHYBXUFL-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[(3-methyl-2h-indazol-6-yl)amino]pyrimidine-5-carboxamide Chemical compound C=1C=C2C(C)=NNC2=CC=1NC(N=1)=NC=C(C(N)=O)C=1NC1CC1 VLNMBPSHYBXUFL-UHFFFAOYSA-N 0.000 claims 1
CPJOAGWNDKKJGB-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-(1,2,4-triazol-1-yl)anilino]pyrimidine-5-carboxamide Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1N1C=NC=N1 CPJOAGWNDKKJGB-UHFFFAOYSA-N 0.000 claims 1
VDNAYMSEGNFTCD-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-(1,2-oxazol-3-yl)anilino]pyrimidine-5-carboxamide Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1C=1C=CON=1 VDNAYMSEGNFTCD-UHFFFAOYSA-N 0.000 claims 1
FVMBDOPKWFDZCC-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-(1,3-oxazol-5-yl)anilino]pyrimidine-5-carboxamide Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1C1=CN=CO1 FVMBDOPKWFDZCC-UHFFFAOYSA-N 0.000 claims 1
WRJYZDQGFSKFRM-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-(1,3-thiazol-2-ylsulfamoyl)anilino]pyrimidine-5-carboxamide Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1S(=O)(=O)NC1=NC=CS1 WRJYZDQGFSKFRM-UHFFFAOYSA-N 0.000 claims 1
MRKVTGWFUVHQOF-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-(1,3-thiazol-4-yl)anilino]pyrimidine-5-carboxamide Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1C1=CSC=N1 MRKVTGWFUVHQOF-UHFFFAOYSA-N 0.000 claims 1
IYUTVDUGMBXLNA-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-(1,3-thiazol-4-ylmethylsulfonyl)anilino]pyrimidine-5-carboxamide Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1S(=O)(=O)CC1=CSC=N1 IYUTVDUGMBXLNA-UHFFFAOYSA-N 0.000 claims 1
NNYCNNXZUPOPRL-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-(1-methylsulfonyl-3,6-dihydro-2h-pyridin-4-yl)anilino]pyrimidine-5-carboxamide Chemical compound C1N(S(=O)(=O)C)CCC(C=2C=CC(NC=3N=C(NC4CC4)C(C(N)=O)=CN=3)=CC=2)=C1 NNYCNNXZUPOPRL-UHFFFAOYSA-N 0.000 claims 1
MDLNYMJOJWRRBQ-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-(1-methylsulfonylpiperidin-4-yl)anilino]pyrimidine-5-carboxamide Chemical compound C1CN(S(=O)(=O)C)CCC1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 MDLNYMJOJWRRBQ-UHFFFAOYSA-N 0.000 claims 1
RYSKCTAISSFRBM-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-(2-hydroxyethylcarbamoyl)anilino]pyrimidine-5-carboxamide Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC1=CC=C(C(=O)NCCO)C=C1 RYSKCTAISSFRBM-UHFFFAOYSA-N 0.000 claims 1
YXQVTLSZASOYQR-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-(2-methoxyethylsulfamoyl)anilino]pyrimidine-5-carboxamide Chemical compound C1=CC(S(=O)(=O)NCCOC)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 YXQVTLSZASOYQR-UHFFFAOYSA-N 0.000 claims 1
MRMUHNIFXSEUDU-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-(2-methylpropoxy)anilino]pyrimidine-5-carboxamide Chemical compound C1=CC(OCC(C)C)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 MRMUHNIFXSEUDU-UHFFFAOYSA-N 0.000 claims 1
KNALDSQTJPPEKT-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-(3,3-difluoropiperidin-1-yl)anilino]pyrimidine-5-carboxamide Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1N1CCCC(F)(F)C1 KNALDSQTJPPEKT-UHFFFAOYSA-N 0.000 claims 1
RGOZWVYEQRUTTA-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-(3,3-difluoropyrrolidin-1-yl)anilino]pyrimidine-5-carboxamide Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1N1CCC(F)(F)C1 RGOZWVYEQRUTTA-UHFFFAOYSA-N 0.000 claims 1
NULJKCIHPNAGMM-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-(3,5-dimethylpyrazol-1-yl)anilino]pyrimidine-5-carboxamide Chemical compound N1=C(C)C=C(C)N1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 NULJKCIHPNAGMM-UHFFFAOYSA-N 0.000 claims 1
SMTTXMQMCRURAC-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-(4-cyclopropylsulfonylpiperazin-1-yl)anilino]pyrimidine-5-carboxamide Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1N(CC1)CCN1S(=O)(=O)C1CC1 SMTTXMQMCRURAC-UHFFFAOYSA-N 0.000 claims 1
BGLPECHZZQDNCD-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-(4-ethylsulfonylpiperazin-1-yl)anilino]pyrimidine-5-carboxamide Chemical compound C1CN(S(=O)(=O)CC)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 BGLPECHZZQDNCD-UHFFFAOYSA-N 0.000 claims 1
KOWLVRYHBXPKFN-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-(4-fluoropiperidin-1-yl)anilino]pyrimidine-5-carboxamide Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1N1CCC(F)CC1 KOWLVRYHBXPKFN-UHFFFAOYSA-N 0.000 claims 1
ORRUMRPFGASMIQ-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-(4-hydroxypiperidin-1-yl)anilino]pyrimidine-5-carboxamide Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1N1CCC(O)CC1 ORRUMRPFGASMIQ-UHFFFAOYSA-N 0.000 claims 1
UFMVEOGLXZVDME-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-(4-hydroxypiperidin-1-yl)sulfonylanilino]pyrimidine-5-carboxamide Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1S(=O)(=O)N1CCC(O)CC1 UFMVEOGLXZVDME-UHFFFAOYSA-N 0.000 claims 1
FVLPJFPAEKKUPP-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-(4-methylsulfonyl-1,4-diazepan-1-yl)anilino]pyrimidine-5-carboxamide Chemical compound C1CN(S(=O)(=O)C)CCCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 FVLPJFPAEKKUPP-UHFFFAOYSA-N 0.000 claims 1
PFDUPXGEXSITJW-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-(4-methylsulfonylpiperazin-1-yl)anilino]pyrimidine-5-carboxamide Chemical compound C1CN(S(=O)(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 PFDUPXGEXSITJW-UHFFFAOYSA-N 0.000 claims 1
QMILCSKOWQFFMF-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-(4-methylsulfonylpiperazine-1-carbonyl)anilino]pyrimidine-5-carboxamide Chemical compound C1CN(S(=O)(=O)C)CCN1C(=O)C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 QMILCSKOWQFFMF-UHFFFAOYSA-N 0.000 claims 1
AHNWHLFVWAMOET-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-(4-pyridin-2-ylpiperazin-1-yl)anilino]pyrimidine-5-carboxamide Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1N(CC1)CCN1C1=CC=CC=N1 AHNWHLFVWAMOET-UHFFFAOYSA-N 0.000 claims 1
ALNHDGRMLWRTIZ-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-(cyclopropylsulfamoyl)anilino]pyrimidine-5-carboxamide Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1S(=O)(=O)NC1CC1 ALNHDGRMLWRTIZ-UHFFFAOYSA-N 0.000 claims 1
VIKZLWYBCVCWGF-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-(dimethylcarbamoyl)anilino]pyrimidine-5-carboxamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 VIKZLWYBCVCWGF-UHFFFAOYSA-N 0.000 claims 1
YOHRMPQLIFCJQD-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-(methylcarbamoyl)anilino]pyrimidine-5-carboxamide Chemical compound C1=CC(C(=O)NC)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 YOHRMPQLIFCJQD-UHFFFAOYSA-N 0.000 claims 1
RFJOCHLDMCMRML-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-(tetrazol-1-yl)anilino]pyrimidine-5-carboxamide Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1N1C=NN=N1 RFJOCHLDMCMRML-UHFFFAOYSA-N 0.000 claims 1
GSKWJEHUOVNQBA-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-(trifluoromethoxy)anilino]pyrimidine-5-carboxamide Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC1=CC=C(OC(F)(F)F)C=C1 GSKWJEHUOVNQBA-UHFFFAOYSA-N 0.000 claims 1
CEWOXYZGVYNPJD-QGZVFWFLSA-N 4-(cyclopropylamino)-2-[4-[(2r)-2-(dimethylcarbamoyl)pyrrolidin-1-yl]anilino]pyrimidine-5-carboxamide Chemical compound CN(C)C(=O)[C@H]1CCCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 CEWOXYZGVYNPJD-QGZVFWFLSA-N 0.000 claims 1
DXHHGKKZXAXBBM-MRXNPFEDSA-N 4-(cyclopropylamino)-2-[4-[(2r)-2-(methoxymethyl)pyrrolidin-1-yl]anilino]pyrimidine-5-carboxamide Chemical compound COC[C@H]1CCCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 DXHHGKKZXAXBBM-MRXNPFEDSA-N 0.000 claims 1
XYWGVHXAHLXUJH-MRXNPFEDSA-N 4-(cyclopropylamino)-2-[4-[(2r)-2-(methylcarbamoyl)pyrrolidin-1-yl]anilino]pyrimidine-5-carboxamide Chemical compound CNC(=O)[C@H]1CCCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 XYWGVHXAHLXUJH-MRXNPFEDSA-N 0.000 claims 1
HYEBKXYMXANZMS-SFHVURJKSA-N 4-(cyclopropylamino)-2-[4-[(2s)-2-(dimethylcarbamoyl)piperidin-1-yl]anilino]pyrimidine-5-carboxamide Chemical compound CN(C)C(=O)[C@@H]1CCCCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 HYEBKXYMXANZMS-SFHVURJKSA-N 0.000 claims 1
CEWOXYZGVYNPJD-KRWDZBQOSA-N 4-(cyclopropylamino)-2-[4-[(2s)-2-(dimethylcarbamoyl)pyrrolidin-1-yl]anilino]pyrimidine-5-carboxamide Chemical compound CN(C)C(=O)[C@@H]1CCCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 CEWOXYZGVYNPJD-KRWDZBQOSA-N 0.000 claims 1
DXHHGKKZXAXBBM-INIZCTEOSA-N 4-(cyclopropylamino)-2-[4-[(2s)-2-(methoxymethyl)pyrrolidin-1-yl]anilino]pyrimidine-5-carboxamide Chemical compound COC[C@@H]1CCCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 DXHHGKKZXAXBBM-INIZCTEOSA-N 0.000 claims 1
FHDDYJFHUQMXPE-KRWDZBQOSA-N 4-(cyclopropylamino)-2-[4-[(2s)-2-(methylcarbamoyl)piperidin-1-yl]anilino]pyrimidine-5-carboxamide Chemical compound CNC(=O)[C@@H]1CCCCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 FHDDYJFHUQMXPE-KRWDZBQOSA-N 0.000 claims 1
XYWGVHXAHLXUJH-INIZCTEOSA-N 4-(cyclopropylamino)-2-[4-[(2s)-2-(methylcarbamoyl)pyrrolidin-1-yl]anilino]pyrimidine-5-carboxamide Chemical compound CNC(=O)[C@@H]1CCCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 XYWGVHXAHLXUJH-INIZCTEOSA-N 0.000 claims 1
PIPZSMASIQNSHM-WBVHZDCISA-N 4-(cyclopropylamino)-2-[4-[(2s,4r)-2-(dimethylcarbamoyl)-4-hydroxypyrrolidin-1-yl]anilino]pyrimidine-5-carboxamide Chemical compound CN(C)C(=O)[C@@H]1C[C@@H](O)CN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 PIPZSMASIQNSHM-WBVHZDCISA-N 0.000 claims 1
RMSSSHITXJRPPI-ZBFHGGJFSA-N 4-(cyclopropylamino)-2-[4-[(2s,4r)-4-hydroxy-2-(methylcarbamoyl)pyrrolidin-1-yl]anilino]pyrimidine-5-carboxamide Chemical compound CNC(=O)[C@@H]1C[C@@H](O)CN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 RMSSSHITXJRPPI-ZBFHGGJFSA-N 0.000 claims 1
RMSSSHITXJRPPI-HOCLYGCPSA-N 4-(cyclopropylamino)-2-[4-[(2s,4s)-4-hydroxy-2-(methylcarbamoyl)pyrrolidin-1-yl]anilino]pyrimidine-5-carboxamide Chemical compound CNC(=O)[C@@H]1C[C@H](O)CN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 RMSSSHITXJRPPI-HOCLYGCPSA-N 0.000 claims 1
MCYCUNWZLOVYKT-CQSZACIVSA-N 4-(cyclopropylamino)-2-[4-[(3r)-3-(dimethylcarbamoyl)piperidin-1-yl]anilino]pyrimidine-5-carboxamide Chemical compound C1[C@H](C(=O)N(C)C)CCCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 MCYCUNWZLOVYKT-CQSZACIVSA-N 0.000 claims 1
MCYCUNWZLOVYKT-AWEZNQCLSA-N 4-(cyclopropylamino)-2-[4-[(3s)-3-(dimethylcarbamoyl)piperidin-1-yl]anilino]pyrimidine-5-carboxamide Chemical compound C1[C@@H](C(=O)N(C)C)CCCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 MCYCUNWZLOVYKT-AWEZNQCLSA-N 0.000 claims 1
CQNHZTVKOGLVDJ-ZDUSSCGKSA-N 4-(cyclopropylamino)-2-[4-[(3s)-3-(methylcarbamoyl)piperidin-1-yl]anilino]pyrimidine-5-carboxamide Chemical compound C1[C@@H](C(=O)NC)CCCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 CQNHZTVKOGLVDJ-ZDUSSCGKSA-N 0.000 claims 1
HHQHGAVOLGVIOS-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-[(4-methylsulfonylpiperazin-1-yl)methyl]anilino]pyrimidine-5-carboxamide Chemical compound C1CN(S(=O)(=O)C)CCN1CC(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 HHQHGAVOLGVIOS-UHFFFAOYSA-N 0.000 claims 1
CCMFJUBOHNTXKN-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-[(5-methyl-1,2-oxazol-3-yl)sulfamoyl]anilino]pyrimidine-5-carboxamide Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C=CC(NC=3N=C(NC4CC4)C(C(N)=O)=CN=3)=CC=2)=N1 CCMFJUBOHNTXKN-UHFFFAOYSA-N 0.000 claims 1
LERGTGFPESKZDP-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-[3-(methylcarbamoyl)pyrrolidin-1-yl]anilino]pyrimidine-5-carboxamide Chemical compound C1C(C(=O)NC)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 LERGTGFPESKZDP-UHFFFAOYSA-N 0.000 claims 1
XGNMWAXFHUUTOC-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-[4-(1-methylcyclopropyl)piperazin-1-yl]anilino]pyrimidine-5-carboxamide Chemical compound C1CN(C=2C=CC(NC=3N=C(NC4CC4)C(C(N)=O)=CN=3)=CC=2)CCN1C1(C)CC1 XGNMWAXFHUUTOC-UHFFFAOYSA-N 0.000 claims 1
YEWSMGFVDCLCQN-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-[4-(2-hydroxyethyl)piperazin-1-yl]anilino]pyrimidine-5-carboxamide Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1N1CCN(CCO)CC1 YEWSMGFVDCLCQN-UHFFFAOYSA-N 0.000 claims 1
AJCOQAVJDPFVJB-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-[4-(2-methoxyethyl)piperazin-1-yl]anilino]pyrimidine-5-carboxamide Chemical compound C1CN(CCOC)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 AJCOQAVJDPFVJB-UHFFFAOYSA-N 0.000 claims 1
NUYBTOGZXWOVFV-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-[4-(dimethylcarbamoyl)piperazin-1-yl]anilino]pyrimidine-5-carboxamide Chemical compound C1CN(C(=O)N(C)C)CCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 NUYBTOGZXWOVFV-UHFFFAOYSA-N 0.000 claims 1
BSOFPQRDXQYEOO-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-[4-(morpholine-4-carbonyl)piperidin-1-yl]anilino]pyrimidine-5-carboxamide Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1N(CC1)CCC1C(=O)N1CCOCC1 BSOFPQRDXQYEOO-UHFFFAOYSA-N 0.000 claims 1
BISMJMGHNOUPOP-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-[4-(piperidine-1-carbonyl)piperidin-1-yl]anilino]pyrimidine-5-carboxamide Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1N(CC1)CCC1C(=O)N1CCCCC1 BISMJMGHNOUPOP-UHFFFAOYSA-N 0.000 claims 1
YXKBQKIMESQSGL-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-[4-(pyrrolidine-1-carbonyl)piperidin-1-yl]anilino]pyrimidine-5-carboxamide Chemical compound N1=C(NC2CC2)C(C(=O)N)=CN=C1NC(C=C1)=CC=C1N(CC1)CCC1C(=O)N1CCCC1 YXKBQKIMESQSGL-UHFFFAOYSA-N 0.000 claims 1
WWZRZHRXWUUKFR-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-[cyclopropyl(methyl)carbamoyl]anilino]pyrimidine-5-carboxamide Chemical compound C=1C=C(NC=2N=C(NC3CC3)C(C(N)=O)=CN=2)C=CC=1C(=O)N(C)C1CC1 WWZRZHRXWUUKFR-UHFFFAOYSA-N 0.000 claims 1
KJHHLNOWNYZUAI-UHFFFAOYSA-N 4-(cyclopropylamino)-2-[4-[methyl(propanoyl)amino]anilino]pyrimidine-5-carboxamide Chemical compound C1=CC(N(C)C(=O)CC)=CC=C1NC1=NC=C(C(N)=O)C(NC2CC2)=N1 KJHHLNOWNYZUAI-UHFFFAOYSA-N 0.000 claims 1
NWRVZMMNDSHDNA-SFHVURJKSA-N 4-(cyclopropylmethylamino)-2-[4-[(2s)-2-(methylcarbamoyl)piperidin-1-yl]anilino]pyrimidine-5-carboxamide Chemical compound CNC(=O)[C@@H]1CCCCN1C(C=C1)=CC=C1NC1=NC=C(C(N)=O)C(NCC2CC2)=N1 NWRVZMMNDSHDNA-SFHVURJKSA-N 0.000 claims 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
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AU2009251863A 2008-04-16 2009-04-16 2, 6-diamino-pyrimidin- 5-yl-carboxamides as syk or JAK kinases inhibitors Active AU2009251863B2 (en)

Applications Claiming Priority (13)

Application Number	Priority Date	Filing Date	Title
US4540608P	2008-04-16	2008-04-16
US4539908P	2008-04-16	2008-04-16
US4541708P	2008-04-16	2008-04-16
US61/045,417		2008-04-16
US61/045,399		2008-04-16
US61/045,406		2008-04-16
US12034108P	2008-12-05	2008-12-05
US12034808P	2008-12-05	2008-12-05
US12034408P	2008-12-05	2008-12-05
US61/120,348		2008-12-05
US61/120,344		2008-12-05
US61/120,341		2008-12-05
PCT/US2009/002420 WO2009145856A1 (en)	2008-04-16	2009-04-16	2, 6-diamino-pyrimidin- 5-yl-carboxamides as syk or jak kinases inhibitors

Publications (3)

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AU2009251863A1 AU2009251863A1 (en)	2009-12-03
AU2009251863A2 AU2009251863A2 (en)	2011-06-09
AU2009251863B2 true AU2009251863B2 (en)	2014-09-25

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AU (1)	AU2009251863B2 (hu)
BR (1)	BRPI0910560B8 (hu)
CO (1)	CO6331433A2 (hu)
CY (1)	CY1118559T1 (hu)
DK (1)	DK2321283T3 (hu)
ES (1)	ES2597441T3 (hu)
GT (1)	GT201000298A (hu)
HK (1)	HK1158179A1 (hu)
HU (1)	HUE031638T2 (hu)
IL (3)	IL208637A (hu)
LT (1)	LT2321283T (hu)
MX (1)	MX353206B (hu)
NI (1)	NI201000176A (hu)
NZ (1)	NZ589314A (hu)
PL (1)	PL2321283T3 (hu)
PT (1)	PT2321283T (hu)
SI (1)	SI2321283T1 (hu)
ZA (1)	ZA201007045B (hu)

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AU2013202496B2 (en) *	2008-06-27	2016-08-04	Celgene Car Llc	Heteroaryl compounds and uses thereof
KR101892989B1 (ko)	2008-06-27	2018-08-30	셀젠 카르 엘엘씨	헤테로아릴 화합물 및 이의 용도
US8338439B2 (en)	2008-06-27	2012-12-25	Celgene Avilomics Research, Inc.	2,4-disubstituted pyrimidines useful as kinase inhibitors
KR20130099040A (ko)	2010-08-10	2013-09-05	셀진 아빌로믹스 리서치, 인코포레이티드	Ｂｔｋ 억제제의 베실레이트 염
WO2014124230A2 (en)	2013-02-08	2014-08-14	Celgene Avilomics Research, Inc.	Erk inhibitors and uses thereof
DK3179858T3 (da)	2014-08-13	2019-07-22	Celgene Car Llc	Forme og sammensætninger af en ERK-inhibitor
EP4306172A4 (en) *	2021-03-09	2025-03-26	Cspc Zhongqi Pharmaceutical Tech Shijiazhuang Co Ltd	USE OF A COMPOUND CONTAINING A TRICYCLIC HETEROARYL
CN114196651B (zh) *	2021-12-15	2023-06-30	中国林业科学研究院亚热带林业研究所	D6蛋白激酶d6pkl2的新用途

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WO2008009458A1 (en) *	2006-07-21	2008-01-24	Novartis Ag	2, 4 -di (arylaminio) -pyrimidine-5-carboxamide compounds as jak kinases inhibitors

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Publication number	Publication date
BRPI0910560B8 (pt)	2023-03-21
CY1118559T1 (el)	2017-07-12
IL274522A (en)	2020-06-30
BRPI0910560B1 (pt)	2023-01-24
AU2009251863A1 (en)	2009-12-03
PL2321283T3 (pl)	2017-01-31
ES2597441T3 (es)	2017-01-18
AU2009251863A2 (en)	2011-06-09
NI201000176A (es)	2011-08-08
LT2321283T (lt)	2016-12-12
PT2321283T (pt)	2016-10-19
HK1158179A1 (zh)	2012-07-13
IL251655B (en)	2020-05-31
NZ589314A (en)	2012-10-26
IL251655A0 (en)	2017-06-29
HUE031638T2 (hu)	2017-07-28
GT201000298A (es)	2014-05-07
MX353206B (es)	2018-01-08
IL208637A (en)	2017-04-30
IL208637A0 (en)	2010-12-30
ZA201007045B (en)	2012-08-29
CO6331433A2 (es)	2011-10-20
DK2321283T3 (en)	2016-10-31
BRPI0910560A2 (pt)	2021-04-27
SI2321283T1 (sl)	2017-01-31
MX2010011464A (es)	2014-06-16

Publication	Publication Date	Title
US11414410B2 (en)	2022-08-16	Inhibitors of protein kinases
CA2960692C (en)	2019-09-24	2,6-diamino-pyrimidin-5-yl-carboxamides as syk or jak kinase inhibitors
US9139581B2 (en)	2015-09-22	Inhibitors of protein kinases
AU2009244897B2 (en)	2014-11-13	2, 6-diamino- pyrimidin- 5-yl-carboxamides as syk or JAK kinases inhibitors
CA2728893A1 (en)	2009-11-12	Inhibitors of syk protein kinase
AU2009251863B2 (en)	2014-09-25	2, 6-diamino-pyrimidin- 5-yl-carboxamides as syk or JAK kinases inhibitors

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2011-06-09	DA3	Amendments made section 104	Free format text: THE NATURE OF THE AMENDMENT IS AS SHOWN IN THE STATEMENT(S) FILED 19 MAY 2011
2015-01-22	FGA	Letters patent sealed or granted (standard patent)
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