CA2753236A1

CA2753236A1 - Pyrrolopyrimidines used as kinase inhibitors

Pyrrolopyrimidines used as kinase inhibitors Download PDF

Info

Publication number: CA2753236A1
Authority: CA; Canada
Prior art keywords: pyrrolo; pyrimidin; propyl; amide; alkyl
Prior art date: 2009-03-04
Legal status : Abandoned

Application number

CA2753236A

Other languages

English (en)

French (fr)

Inventor

Edward Giles Mciver

Joane Hough

Current Assignee

LifeArc

Original Assignee

Medical Research Council Technology

Priority date

2009-03-04

Filing date

2010-03-04

Publication date

2010-09-10

2010-03-04 Application filed by Medical Research Council Technology filed Critical Medical Research Council Technology

2010-09-10 Publication of CA2753236A1 publication Critical patent/CA2753236A1/en

Status Abandoned legal-status Critical Current

Links

150000004944 pyrrolopyrimidines Chemical class 0.000 title description 4
229940043355 kinase inhibitor Drugs 0.000 title description 2
239000003757 phosphotransferase inhibitor Substances 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 194
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 59
238000000034 method Methods 0.000 claims abstract description 57
108091000080 Phosphotransferase Proteins 0.000 claims abstract description 55
102000020233 phosphotransferase Human genes 0.000 claims abstract description 55
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 53
101000665442 Homo sapiens Serine/threonine-protein kinase TBK1 Proteins 0.000 claims abstract description 52
102100038192 Serine/threonine-protein kinase TBK1 Human genes 0.000 claims abstract description 52
206010030348 Open-Angle Glaucoma Diseases 0.000 claims abstract description 40
201000006366 primary open angle glaucoma Diseases 0.000 claims abstract description 40
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 39
125000003118 aryl group Chemical group 0.000 claims abstract description 30
208000035475 disorder Diseases 0.000 claims abstract description 27
239000003814 drug Substances 0.000 claims abstract description 27
102000001284 I-kappa-B kinase Human genes 0.000 claims abstract description 23
108060006678 I-kappa-B kinase Proteins 0.000 claims abstract description 23
101001059429 Homo sapiens MAP/microtubule affinity-regulating kinase 3 Proteins 0.000 claims abstract description 22
102100028920 MAP/microtubule affinity-regulating kinase 3 Human genes 0.000 claims abstract description 22
229910052736 halogen Inorganic materials 0.000 claims abstract description 22
150000002367 halogens Chemical class 0.000 claims abstract description 22
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 22
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
102100023483 Mitogen-activated protein kinase 15 Human genes 0.000 claims abstract description 19
150000003839 salts Chemical class 0.000 claims abstract description 19
206010040070 Septic Shock Diseases 0.000 claims abstract description 18
230000000694 effects Effects 0.000 claims abstract description 18
230000036303 septic shock Effects 0.000 claims abstract description 18
238000002360 preparation method Methods 0.000 claims abstract description 17
206010028980 Neoplasm Diseases 0.000 claims abstract description 15
239000001257 hydrogen Substances 0.000 claims abstract description 15
201000011510 cancer Diseases 0.000 claims abstract description 14
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 11
150000002148 esters Chemical class 0.000 claims abstract description 11
208000024827 Alzheimer disease Diseases 0.000 claims abstract description 10
201000009273 Endometriosis Diseases 0.000 claims abstract description 10
208000017442 Retinal disease Diseases 0.000 claims abstract description 10
206010038923 Retinopathy Diseases 0.000 claims abstract description 10
208000037976 chronic inflammation Diseases 0.000 claims abstract description 10
230000006020 chronic inflammation Effects 0.000 claims abstract description 10
206010020718 hyperplasia Diseases 0.000 claims abstract description 10
206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 10
201000004681 Psoriasis Diseases 0.000 claims abstract description 8
230000002159 abnormal effect Effects 0.000 claims abstract description 6
150000002431 hydrogen Chemical group 0.000 claims abstract description 5
230000002265 prevention Effects 0.000 claims abstract description 5
108010024986 Cyclin-Dependent Kinase 2 Proteins 0.000 claims abstract 4
102100036239 Cyclin-dependent kinase 2 Human genes 0.000 claims abstract 4
101000976899 Homo sapiens Mitogen-activated protein kinase 15 Proteins 0.000 claims abstract 4
-1 cyano, hydroxyl Chemical group 0.000 claims description 153
TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 claims description 53
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 47
201000010099 disease Diseases 0.000 claims description 26
229910052757 nitrogen Inorganic materials 0.000 claims description 22
238000003556 assay Methods 0.000 claims description 19
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 16
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
239000001301 oxygen Substances 0.000 claims description 16
229910052760 oxygen Inorganic materials 0.000 claims description 16
101000820294 Homo sapiens Tyrosine-protein kinase Yes Proteins 0.000 claims description 15
102100021788 Tyrosine-protein kinase Yes Human genes 0.000 claims description 15
CAMSUDMBGHNVCS-UHFFFAOYSA-N n-[3-[2-[(1-methylindazol-5-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C=1C=C2N(C)N=CC2=CC=1NC(N=C12)=NC=C1C=CN2CCCNC(=O)C1CCC1 CAMSUDMBGHNVCS-UHFFFAOYSA-N 0.000 claims description 14
150000001412 amines Chemical class 0.000 claims description 13
JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 claims description 13
125000005843 halogen group Chemical group 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
125000001424 substituent group Chemical group 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
230000002401 inhibitory effect Effects 0.000 claims description 10
HXVAENCJCDIHDG-UHFFFAOYSA-N n-[3-[2-[3-(1,3-oxazol-5-yl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1CCC1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC(C=1)=CC=CC=1C1=CN=CO1 HXVAENCJCDIHDG-UHFFFAOYSA-N 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 9
201000008482 osteoarthritis Diseases 0.000 claims description 9
230000008569 process Effects 0.000 claims description 9
UNWGHJICAJXZAG-UHFFFAOYSA-N 2-cyclopropyl-n-[3-[2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]acetamide Chemical compound C1=CC2=CN=C(NC=3C=NC(=CC=3)N3CCOCC3)N=C2N1CCCNC(=O)CC1CC1 UNWGHJICAJXZAG-UHFFFAOYSA-N 0.000 claims description 8
239000005864 Sulphur Substances 0.000 claims description 8
239000003085 diluting agent Substances 0.000 claims description 8
CTUNVQYSBNVSSI-UHFFFAOYSA-N n-[3-[5-bromo-2-(3-fluoroanilino)pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound FC1=CC=CC(NC=2N=C3N(CCCNC(=O)C4CCC4)C=C(Br)C3=CN=2)=C1 CTUNVQYSBNVSSI-UHFFFAOYSA-N 0.000 claims description 8
239000000546 pharmaceutical excipient Substances 0.000 claims description 8
125000004076 pyridyl group Chemical group 0.000 claims description 8
229910052717 sulfur Inorganic materials 0.000 claims description 8
239000011593 sulfur Substances 0.000 claims description 8
QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 claims description 8
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
241000124008 Mammalia Species 0.000 claims description 7
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 7
UXBFGLMTWRQROK-UHFFFAOYSA-N n-[3-[2-[(1-methylpyrazol-4-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1=NN(C)C=C1NC1=NC=C(C=CN2CCCNC(=O)C3CCC3)C2=N1 UXBFGLMTWRQROK-UHFFFAOYSA-N 0.000 claims description 7
XLGHMHOCMLFSOF-UHFFFAOYSA-N n-[3-[2-[4-(1,3-oxazol-5-yl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1CCC1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC(C=C1)=CC=C1C1=CN=CO1 XLGHMHOCMLFSOF-UHFFFAOYSA-N 0.000 claims description 7
125000003226 pyrazolyl group Chemical group 0.000 claims description 7
229920006395 saturated elastomer Polymers 0.000 claims description 7
IGXIMFJXKCORFY-UHFFFAOYSA-N 2-methyl-n-[3-[2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]propanamide Chemical compound N1=C2N(CCCNC(=O)C(C)C)C=CC2=CN=C1NC(C=N1)=CC=C1N1CCOCC1 IGXIMFJXKCORFY-UHFFFAOYSA-N 0.000 claims description 6
JBDXZYCZTGLKSE-UHFFFAOYSA-N 3-methyl-n-[3-[2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]butanamide Chemical compound N1=C2N(CCCNC(=O)CC(C)C)C=CC2=CN=C1NC(C=N1)=CC=C1N1CCOCC1 JBDXZYCZTGLKSE-UHFFFAOYSA-N 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 6
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
230000005764 inhibitory process Effects 0.000 claims description 6
GBMZUVCNKNAKAG-UHFFFAOYSA-N n-[3-[2-(3-cyanoanilino)pyrrolo[2,3-d]pyrimidin-7-yl]propyl]thiophene-2-carboxamide Chemical compound C=1C=CSC=1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC1=CC=CC(C#N)=C1 GBMZUVCNKNAKAG-UHFFFAOYSA-N 0.000 claims description 6
LJNCBWDMHFJNTM-UHFFFAOYSA-N n-[3-[2-(3-fluoroanilino)pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound FC1=CC=CC(NC=2N=C3N(CCCNC(=O)C4CCC4)C=CC3=CN=2)=C1 LJNCBWDMHFJNTM-UHFFFAOYSA-N 0.000 claims description 6
VNYOEBQUJAUUFG-UHFFFAOYSA-N n-[3-[2-(4-morpholin-4-ylanilino)pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1CCC1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC(C=C1)=CC=C1N1CCOCC1 VNYOEBQUJAUUFG-UHFFFAOYSA-N 0.000 claims description 6
SVMVLQNRBXGIIV-UHFFFAOYSA-N n-[3-[2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]-1,3-thiazole-5-carboxamide Chemical compound C=1N=CSC=1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC(C=N1)=CC=C1N1CCOCC1 SVMVLQNRBXGIIV-UHFFFAOYSA-N 0.000 claims description 6
IIHXGROJAPUAGM-UHFFFAOYSA-N n-[3-[2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]oxolane-3-carboxamide Chemical compound C1COCC1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC(C=N1)=CC=C1N1CCOCC1 IIHXGROJAPUAGM-UHFFFAOYSA-N 0.000 claims description 6
FFSBKFBLCYIJHD-UHFFFAOYSA-N n-[3-[2-[3-(trifluoromethyl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]thiophene-2-carboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=C3N(CCCNC(=O)C=4SC=CC=4)C=CC3=CN=2)=C1 FFSBKFBLCYIJHD-UHFFFAOYSA-N 0.000 claims description 6
GPQFNIZBUXAFRW-UHFFFAOYSA-N n-[3-[2-[4-(morpholine-4-carbonyl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1CCC1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC(C=C1)=CC=C1C(=O)N1CCOCC1 GPQFNIZBUXAFRW-UHFFFAOYSA-N 0.000 claims description 6
LRUOLZVEZLNTGN-UHFFFAOYSA-N n-[3-[2-[[1-(2-morpholin-4-ylethyl)pyrazol-4-yl]amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1CCC1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC(=C1)C=NN1CCN1CCOCC1 LRUOLZVEZLNTGN-UHFFFAOYSA-N 0.000 claims description 6
UIVUUYYWFTWMHH-UHFFFAOYSA-N n-[3-[5-chloro-2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C12=NC(NC=3C=NC(=CC=3)N3CCOCC3)=NC=C2C(Cl)=CN1CCCNC(=O)C1CCC1 UIVUUYYWFTWMHH-UHFFFAOYSA-N 0.000 claims description 6
DZHDIJJFQDEHDN-UHFFFAOYSA-N n-[3-[[7-[3-(thiophene-2-carbonylamino)propyl]pyrrolo[2,3-d]pyrimidin-2-yl]amino]phenyl]pyrrolidine-1-carboxamide Chemical compound C1CCCN1C(=O)NC(C=1)=CC=CC=1NC(N=C12)=NC=C1C=CN2CCCNC(=O)C1=CC=CS1 DZHDIJJFQDEHDN-UHFFFAOYSA-N 0.000 claims description 6
JVTMFKNWOUPAJH-UHFFFAOYSA-N 2-cyclopentyl-n-[3-[2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]acetamide Chemical compound C1=CC2=CN=C(NC=3C=NC(=CC=3)N3CCOCC3)N=C2N1CCCNC(=O)CC1CCCC1 JVTMFKNWOUPAJH-UHFFFAOYSA-N 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
NPGQUQIVGQHEAE-UHFFFAOYSA-N n-[3-[2-(3-morpholin-4-ylanilino)pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1CCC1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC(C=1)=CC=CC=1N1CCOCC1 NPGQUQIVGQHEAE-UHFFFAOYSA-N 0.000 claims description 5
FGYCJULFFFTMCW-UHFFFAOYSA-N n-[3-[2-(pyridin-3-ylamino)pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1CCC1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC1=CC=CN=C1 FGYCJULFFFTMCW-UHFFFAOYSA-N 0.000 claims description 5
IVOCKDRLDRCJKO-UHFFFAOYSA-N n-[3-[2-(pyridin-3-ylamino)pyrrolo[2,3-d]pyrimidin-7-yl]propyl]thiophene-2-carboxamide Chemical compound C=1C=CSC=1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC1=CC=CN=C1 IVOCKDRLDRCJKO-UHFFFAOYSA-N 0.000 claims description 5
SASKQCOPYLRNPM-UHFFFAOYSA-N n-[3-[2-(quinolin-6-ylamino)pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1=CC2=CN=C(NC=3C=C4C=CC=NC4=CC=3)N=C2N1CCCNC(=O)C1CCC1 SASKQCOPYLRNPM-UHFFFAOYSA-N 0.000 claims description 5
YMSKBSJRJRNOIR-UHFFFAOYSA-N n-[3-[2-(quinoxalin-6-ylamino)pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1=CC2=CN=C(NC=3C=C4N=CC=NC4=CC=3)N=C2N1CCCNC(=O)C1CCC1 YMSKBSJRJRNOIR-UHFFFAOYSA-N 0.000 claims description 5
SOCMOEBIHDQWNA-UHFFFAOYSA-N n-[3-[2-[(1-methylindazol-6-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1=C2N(C)N=CC2=CC=C1NC(N=C12)=NC=C1C=CN2CCCNC(=O)C1CCC1 SOCMOEBIHDQWNA-UHFFFAOYSA-N 0.000 claims description 5
HYZFDZRTUAUVNS-UHFFFAOYSA-N n-[3-[2-[(1-methylpyrazolo[3,4-b]pyridin-5-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C=1N=C2N(C)N=CC2=CC=1NC(N=C12)=NC=C1C=CN2CCCNC(=O)C1CCC1 HYZFDZRTUAUVNS-UHFFFAOYSA-N 0.000 claims description 5
CQTLXLLUCCXTAH-UHFFFAOYSA-N n-[3-[2-[(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1=C2CN(C)CCC2=CC=C1NC(N=C12)=NC=C1C=CN2CCCNC(=O)C1CCC1 CQTLXLLUCCXTAH-UHFFFAOYSA-N 0.000 claims description 5
HHIWINYKIMADIE-UHFFFAOYSA-N n-[3-[2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1CCC1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC(C=N1)=CC=C1N1CCOCC1 HHIWINYKIMADIE-UHFFFAOYSA-N 0.000 claims description 5
BKRCADGEPNHIPK-UHFFFAOYSA-N n-[3-[2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclohexanecarboxamide Chemical compound C1CCCCC1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC(C=N1)=CC=C1N1CCOCC1 BKRCADGEPNHIPK-UHFFFAOYSA-N 0.000 claims description 5
TWPYVVZZLDOPKE-UHFFFAOYSA-N n-[3-[2-[3-(morpholin-4-ylmethyl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1CCC1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC(C=1)=CC=CC=1CN1CCOCC1 TWPYVVZZLDOPKE-UHFFFAOYSA-N 0.000 claims description 5
QQPOCQHJIBTSKM-UHFFFAOYSA-N n-[3-[2-[3-(pyrrolidin-1-ylmethyl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1CCC1C(=O)NCCCN(C1=N2)C=CC1=CN=C2NC(C=1)=CC=CC=1CN1CCCC1 QQPOCQHJIBTSKM-UHFFFAOYSA-N 0.000 claims description 5
PHBLKWNWRZWSOY-UHFFFAOYSA-N n-[3-[2-[4-(4-hydroxy-1-methylpiperidin-4-yl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1CN(C)CCC1(O)C(C=C1)=CC=C1NC1=NC=C(C=CN2CCCNC(=O)C3CCC3)C2=N1 PHBLKWNWRZWSOY-UHFFFAOYSA-N 0.000 claims description 5
QKBQBFGPMAXZLO-UHFFFAOYSA-N n-[3-[2-[4-(4-methoxy-1-methylpiperidin-4-yl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C=1C=C(NC=2N=C3N(CCCNC(=O)C4CCC4)C=CC3=CN=2)C=CC=1C1(OC)CCN(C)CC1 QKBQBFGPMAXZLO-UHFFFAOYSA-N 0.000 claims description 5
IAQZCAABGCPKQD-UHFFFAOYSA-N n-[3-[2-[4-(4-methylpiperazin-1-yl)anilino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C(C=CN2CCCNC(=O)C3CCC3)C2=N1 IAQZCAABGCPKQD-UHFFFAOYSA-N 0.000 claims description 5
VPPQZQLLVNZCJA-UHFFFAOYSA-N n-[3-[2-[4-[(dimethylamino)methyl]anilino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1=CC(CN(C)C)=CC=C1NC1=NC=C(C=CN2CCCNC(=O)C3CCC3)C2=N1 VPPQZQLLVNZCJA-UHFFFAOYSA-N 0.000 claims description 5
DXCQLKJTTKRJSX-UHFFFAOYSA-N n-[3-[2-[[6-(4-methyl-1,4-diazepan-1-yl)pyridin-3-yl]amino]pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound C1CN(C)CCCN1C(N=C1)=CC=C1NC1=NC=C(C=CN2CCCNC(=O)C3CCC3)C2=N1 DXCQLKJTTKRJSX-UHFFFAOYSA-N 0.000 claims description 5
CFYXSQVZWRIGKJ-UHFFFAOYSA-N n-[3-[5-cyano-2-(3-fluoroanilino)pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclobutanecarboxamide Chemical compound FC1=CC=CC(NC=2N=C3N(CCCNC(=O)C4CCC4)C=C(C3=CN=2)C#N)=C1 CFYXSQVZWRIGKJ-UHFFFAOYSA-N 0.000 claims description 5
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
SIKXIUWKPGWBBF-UHFFFAOYSA-N 5-bromo-2,4-dichloropyrimidine Chemical compound ClC1=NC=C(Br)C(Cl)=N1 SIKXIUWKPGWBBF-UHFFFAOYSA-N 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims description 4
SQZZHXLACIZYDV-UHFFFAOYSA-N n-[3-[2-(3-fluoroanilino)pyrrolo[2,3-d]pyrimidin-7-yl]propyl]cyclopentanecarboxamide Chemical compound FC1=CC=CC(NC=2N=C3N(CCCNC(=O)C4CCCC4)C=CC3=CN=2)=C1 SQZZHXLACIZYDV-UHFFFAOYSA-N 0.000 claims description 4
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