CA2764983A1

CA2764983A1 - 2- ( lh-pyrazol-4 -ylamino ) -pyrimidine as kinase inhibitors

2- ( lh-pyrazol-4 -ylamino ) -pyrimidine as kinase inhibitors Download PDF

Info

Publication number: CA2764983A1
Authority: CA; Canada
Prior art keywords: amino; pyrazol; pyrimidin; carboxamide; bicyclo
Prior art date: 2009-06-10
Legal status : Abandoned

Application number

CA2764983A

Other languages

English (en)

French (fr)

Inventor

Michael L. Curtin

Michael R. Michaelides

Howard Robin Heyman

Robin R. Frey

Current Assignee

AbbVie Inc

Original Assignee

Abbott Laboratories

Priority date

2009-06-10

Filing date

2010-06-08

Publication date

2010-12-16

2010-06-08 Application filed by Abbott Laboratories filed Critical Abbott Laboratories

2010-12-16 Publication of CA2764983A1 publication Critical patent/CA2764983A1/en

Status Abandoned legal-status Critical Current

Links

229940043355 kinase inhibitor Drugs 0.000 title description 9
239000003757 phosphotransferase inhibitor Substances 0.000 title description 9
150000001875 compounds Chemical class 0.000 claims abstract description 285
150000003839 salts Chemical class 0.000 claims abstract description 45
238000000034 method Methods 0.000 claims abstract description 21
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 257
125000001424 substituent group Chemical group 0.000 claims description 253
-1 -OH Chemical group 0.000 claims description 239
229910052736 halogen Inorganic materials 0.000 claims description 216
150000002367 halogens Chemical class 0.000 claims description 207
125000000217 alkyl group Chemical group 0.000 claims description 142
125000000753 cycloalkyl group Chemical group 0.000 claims description 129
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 118
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 110
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 104
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 85
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 82
125000003118 aryl group Chemical group 0.000 claims description 78
125000003386 piperidinyl group Chemical group 0.000 claims description 74
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 74
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 74
125000002393 azetidinyl group Chemical group 0.000 claims description 73
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 73
125000004093 cyano group Chemical group *C#N 0.000 claims description 71
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 70
229910052739 hydrogen Inorganic materials 0.000 claims description 63
206010028980 Neoplasm Diseases 0.000 claims description 55
239000001257 hydrogen Substances 0.000 claims description 53
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 50
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 49
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 48
ZTUUVDYQBLRAAC-UHFFFAOYSA-N bicyclo[2.2.1]hept-2-ene-5-carboxamide Chemical compound C1C2C(C(=O)N)CC1C=C2 ZTUUVDYQBLRAAC-UHFFFAOYSA-N 0.000 claims description 46
201000011510 cancer Diseases 0.000 claims description 42
229910052801 chlorine Inorganic materials 0.000 claims description 40
229910052731 fluorine Inorganic materials 0.000 claims description 39
125000002757 morpholinyl group Chemical group 0.000 claims description 38
125000004193 piperazinyl group Chemical group 0.000 claims description 38
125000001072 heteroaryl group Chemical group 0.000 claims description 34
125000000623 heterocyclic group Chemical group 0.000 claims description 33
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 31
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 31
125000000392 cycloalkenyl group Chemical group 0.000 claims description 30
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 30
125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 23
125000003342 alkenyl group Chemical group 0.000 claims description 22
229910052794 bromium Inorganic materials 0.000 claims description 20
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
208000026310 Breast neoplasm Diseases 0.000 claims description 11
206010006187 Breast cancer Diseases 0.000 claims description 10
229910006074 SO2NH2 Inorganic materials 0.000 claims description 10
239000000546 pharmaceutical excipient Substances 0.000 claims description 9
206010005003 Bladder cancer Diseases 0.000 claims description 8
241000124008 Mammalia Species 0.000 claims description 8
206010060862 Prostate cancer Diseases 0.000 claims description 8
208000000236 Prostatic Neoplasms Diseases 0.000 claims description 8
OMCDXKNVARSHIM-XXSPCDMZSA-N (1r,2s,3r,4s)-3-[[2-[(1-ethylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]bicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@H]1[C@H]([C@]2([H])CC[C@]1(C2)[H])C(N)=O)C(C(=CN=1)C(F)(F)F)=NC=1NC=1C=NN(CC)C=1 OMCDXKNVARSHIM-XXSPCDMZSA-N 0.000 claims description 7
206010033128 Ovarian cancer Diseases 0.000 claims description 7
208000024770 Thyroid neoplasm Diseases 0.000 claims description 7
208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 7
208000008443 pancreatic carcinoma Diseases 0.000 claims description 7
201000002510 thyroid cancer Diseases 0.000 claims description 7
201000005112 urinary bladder cancer Diseases 0.000 claims description 7
WBVVEHDODCFLBV-XXSPCDMZSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CC)C=1 WBVVEHDODCFLBV-XXSPCDMZSA-N 0.000 claims description 6
206010009944 Colon cancer Diseases 0.000 claims description 6
206010014733 Endometrial cancer Diseases 0.000 claims description 6
206010014759 Endometrial neoplasm Diseases 0.000 claims description 6
208000000461 Esophageal Neoplasms Diseases 0.000 claims description 6
206010058467 Lung neoplasm malignant Diseases 0.000 claims description 6
206010030155 Oesophageal carcinoma Diseases 0.000 claims description 6
208000005718 Stomach Neoplasms Diseases 0.000 claims description 6
201000004101 esophageal cancer Diseases 0.000 claims description 6
206010017758 gastric cancer Diseases 0.000 claims description 6
201000005202 lung cancer Diseases 0.000 claims description 6
208000020816 lung neoplasm Diseases 0.000 claims description 6
201000011549 stomach cancer Diseases 0.000 claims description 6
MWVXACVVOSGAKF-FIDNZITISA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(C)C=1 MWVXACVVOSGAKF-FIDNZITISA-N 0.000 claims description 5
125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 claims description 5
125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 5
206010061535 Ovarian neoplasm Diseases 0.000 claims description 5
206010061902 Pancreatic neoplasm Diseases 0.000 claims description 5
125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims description 5
125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 claims description 5
125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 5
208000029742 colonic neoplasm Diseases 0.000 claims description 5
125000002541 furyl group Chemical group 0.000 claims description 5
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 5
125000001786 isothiazolyl group Chemical group 0.000 claims description 5
125000000842 isoxazolyl group Chemical group 0.000 claims description 5
208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 5
125000002971 oxazolyl group Chemical group 0.000 claims description 5
201000002528 pancreatic cancer Diseases 0.000 claims description 5
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 5
125000003226 pyrazolyl group Chemical group 0.000 claims description 5
125000004076 pyridyl group Chemical group 0.000 claims description 5
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 5
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
238000001959 radiotherapy Methods 0.000 claims description 5
125000000335 thiazolyl group Chemical group 0.000 claims description 5
125000001544 thienyl group Chemical group 0.000 claims description 5
VWNWNXCVJAUZBJ-JFTQMJAMSA-N (1r,2r,3s,4s)-3-[[5-chloro-2-[[1-(2-morpholin-4-ylethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1CCN1CCOCC1 VWNWNXCVJAUZBJ-JFTQMJAMSA-N 0.000 claims description 4
SYPCCMJYEOWKPO-SFUIVIKGSA-N (1r,2r,3s,4s)-3-[[5-chloro-2-[[1-(2-piperidin-1-ylethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1CCN1CCCCC1 SYPCCMJYEOWKPO-SFUIVIKGSA-N 0.000 claims description 4
LDQOJMLOGCBLQT-KTJYFRGRSA-N (1r,2s,3r,4s)-3-[[5-chloro-2-[[1-[2-(methylamino)-2-oxoethyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@H]1[C@H]([C@]2([H])CC[C@]1(C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CC(=O)NC)C=1 LDQOJMLOGCBLQT-KTJYFRGRSA-N 0.000 claims description 4
MENUIGPUGBMCMV-OBPYKSBLSA-N (1s,2s,3r,4r)-3-[[2-[[1-(2-amino-2-oxoethyl)pyrazol-4-yl]amino]-5-chloropyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CC(N)=O)C=1 MENUIGPUGBMCMV-OBPYKSBLSA-N 0.000 claims description 4
MWTDJNYNWATGMS-KTJYFRGRSA-N (1s,2s,3r,4r)-3-[[2-[[1-(azetidin-3-yl)pyrazol-4-yl]amino]-5-chloropyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1C1CNC1 MWTDJNYNWATGMS-KTJYFRGRSA-N 0.000 claims description 4
NPJVSEXPCJZQAI-XXSPCDMZSA-N (1s,2s,3r,4r)-3-[[5-bromo-2-[(1-ethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Br)=NC=1NC=1C=NN(CC)C=1 NPJVSEXPCJZQAI-XXSPCDMZSA-N 0.000 claims description 4
GQUVPTFFAHYFFV-LZJQFABFSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-cyclobutylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1C1CCC1 GQUVPTFFAHYFFV-LZJQFABFSA-N 0.000 claims description 4
RAVOJQLJGOGZMT-FCLUMBPUSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-piperidin-4-ylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1C1CCNCC1 RAVOJQLJGOGZMT-FCLUMBPUSA-N 0.000 claims description 4
RZGZSPBNSZDTFJ-FDRIWYBQSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[1-(2-methoxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CCOC)C=1 RZGZSPBNSZDTFJ-FDRIWYBQSA-N 0.000 claims description 4
FUVCKJYFOFPYSZ-UHFFFAOYSA-N 1-[2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]phenyl]cyclobutan-1-ol Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC=2C(=CC=CC=2)C2(O)CCC2)=N1 FUVCKJYFOFPYSZ-UHFFFAOYSA-N 0.000 claims description 4
206010008342 Cervix carcinoma Diseases 0.000 claims description 4
ZAHXYMFVNNUHCP-UHFFFAOYSA-N Naphazoline nitrate Chemical group O[N+]([O-])=O.C=1C=CC2=CC=CC=C2C=1CC1=NCCN1 ZAHXYMFVNNUHCP-UHFFFAOYSA-N 0.000 claims description 4
208000015634 Rectal Neoplasms Diseases 0.000 claims description 4
208000000453 Skin Neoplasms Diseases 0.000 claims description 4
208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 4
125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
201000010881 cervical cancer Diseases 0.000 claims description 4
125000005412 pyrazyl group Chemical group 0.000 claims description 4
125000002098 pyridazinyl group Chemical group 0.000 claims description 4
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206010038038 rectal cancer Diseases 0.000 claims description 4
201000001275 rectum cancer Diseases 0.000 claims description 4
201000000849 skin cancer Diseases 0.000 claims description 4
MANTWCDJRBWNFR-PJQZNRQZSA-N (1r,2r,3s,4s)-3-[[2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(N=1)=CC=NC=1NC=1C=NN(C)C=1 MANTWCDJRBWNFR-PJQZNRQZSA-N 0.000 claims description 3
CQGVEPWUGYBHNE-SFUIVIKGSA-N (1r,2r,3s,4s)-3-[[5-bromo-2-[[1-(2-piperidin-1-ylethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Br)=NC=1NC(=C1)C=NN1CCN1CCCCC1 CQGVEPWUGYBHNE-SFUIVIKGSA-N 0.000 claims description 3
NJEJIUSXRRPGIL-DTVLGXAZSA-N (1r,2r,3s,4s)-3-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])CC[C@]1(C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(C)C=1 NJEJIUSXRRPGIL-DTVLGXAZSA-N 0.000 claims description 3
WHDZRHLPGYRKOD-MDSNHJATSA-N (1r,2r,3s,4s)-3-[[5-fluoro-2-(1h-pyrazol-4-ylamino)pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=CN=1)F)=NC=1NC=1C=NNC=1 WHDZRHLPGYRKOD-MDSNHJATSA-N 0.000 claims description 3
ZHZCSRZWFSLVJK-KOLCDFICSA-N (1r,2s)-2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]cyclopentane-1-carboxamide Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(N[C@@H]2[C@@H](CCC2)C(N)=O)=N1 ZHZCSRZWFSLVJK-KOLCDFICSA-N 0.000 claims description 3
UXXGXZAZZIYQFC-KOLCDFICSA-N (1r,2s)-2-[[5-fluoro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]cyclopentane-1-carboxamide Chemical compound C1=NN(C)C=C1NC1=NC=C(F)C(N[C@@H]2[C@@H](CCC2)C(N)=O)=N1 UXXGXZAZZIYQFC-KOLCDFICSA-N 0.000 claims description 3
CLPWEIYJUQKGRS-XXSPCDMZSA-N (1r,2s,3r,4s)-3-[[2-[(1-ethylpyrazol-4-yl)amino]-5-fluoropyrimidin-4-yl]amino]bicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@H]1[C@H]([C@]2([H])CC[C@]1(C2)[H])C(N)=O)C(C(=CN=1)F)=NC=1NC=1C=NN(CC)C=1 CLPWEIYJUQKGRS-XXSPCDMZSA-N 0.000 claims description 3
HFGWJQCDWDPUHN-XXSPCDMZSA-N (1r,2s,3r,4s)-3-[[5-chloro-2-[(1-ethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@H]1[C@H]([C@]2([H])CC[C@]1(C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CC)C=1 HFGWJQCDWDPUHN-XXSPCDMZSA-N 0.000 claims description 3
NJEJIUSXRRPGIL-FIDNZITISA-N (1r,2s,3r,4s)-3-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@H]1[C@H]([C@]2([H])CC[C@]1(C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(C)C=1 NJEJIUSXRRPGIL-FIDNZITISA-N 0.000 claims description 3
BCRSULZZWCMCCI-XXSPCDMZSA-N (1r,2s,3r,4s)-3-[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@H]1[C@H]([C@]2([H])CC[C@]1(C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CCO)C=1 BCRSULZZWCMCCI-XXSPCDMZSA-N 0.000 claims description 3
ZHZCSRZWFSLVJK-GXSJLCMTSA-N (1s,2r)-2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]cyclopentane-1-carboxamide Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(N[C@H]2[C@H](CCC2)C(N)=O)=N1 ZHZCSRZWFSLVJK-GXSJLCMTSA-N 0.000 claims description 3
WBVVEHDODCFLBV-QOBDMFJFSA-N (1s,2r,3s,4r)-3-[[5-chloro-2-[(1-ethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CC)C=1 WBVVEHDODCFLBV-QOBDMFJFSA-N 0.000 claims description 3
BBLIGVOVXFAKMZ-XXSPCDMZSA-N (1s,2s,3r,4r)-3-[[2-[(1-ethylpyrazol-4-yl)amino]-5-fluoropyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)F)=NC=1NC=1C=NN(CC)C=1 BBLIGVOVXFAKMZ-XXSPCDMZSA-N 0.000 claims description 3
XNLHVDPDSQODGM-PAPYEOQZSA-N (1s,2s,3r,4r)-3-[[2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]-5-methylpyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)C)=NC=1NC=1C=NN(CCO)C=1 XNLHVDPDSQODGM-PAPYEOQZSA-N 0.000 claims description 3
GSBFYFGYNFREOE-REJLFOLJSA-N (1s,2s,3r,4r)-3-[[5-bromo-2-[(1,3,5-trimethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Br)=NC=1NC=1C(C)=NN(C)C=1C GSBFYFGYNFREOE-REJLFOLJSA-N 0.000 claims description 3
MNRGYCFPHJFBGH-XXSPCDMZSA-N (1s,2s,3r,4r)-3-[[5-bromo-2-[(1,3-dimethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Br)=NC=1NC1=CN(C)N=C1C MNRGYCFPHJFBGH-XXSPCDMZSA-N 0.000 claims description 3
NOUKGAGXHDCVPH-FDRIWYBQSA-N (1s,2s,3r,4r)-3-[[5-bromo-2-[(1-propan-2-ylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Br)=NC=1NC=1C=NN(C(C)C)C=1 NOUKGAGXHDCVPH-FDRIWYBQSA-N 0.000 claims description 3
CHLWDCULZGHGAS-FDRIWYBQSA-N (1s,2s,3r,4r)-3-[[5-bromo-2-[[1-(2-methoxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Br)=NC=1NC=1C=NN(CCOC)C=1 CHLWDCULZGHGAS-FDRIWYBQSA-N 0.000 claims description 3
CQGVEPWUGYBHNE-LVFSCSRESA-N (1s,2s,3r,4r)-3-[[5-bromo-2-[[1-(2-piperidin-1-ylethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Br)=NC=1NC(=C1)C=NN1CCN1CCCCC1 CQGVEPWUGYBHNE-LVFSCSRESA-N 0.000 claims description 3
MSCWBFQHNIWCJE-REJLFOLJSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1,3,5-trimethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C(C)=NN(C)C=1C MSCWBFQHNIWCJE-REJLFOLJSA-N 0.000 claims description 3
UMHCKHKYDVBMBJ-XXSPCDMZSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1,3-dimethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC1=CN(C)N=C1C UMHCKHKYDVBMBJ-XXSPCDMZSA-N 0.000 claims description 3
SFXBHFZUSIUICI-XXSPCDMZSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CCO)C=1 SFXBHFZUSIUICI-XXSPCDMZSA-N 0.000 claims description 3
SYPCCMJYEOWKPO-LVFSCSRESA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[1-(2-piperidin-1-ylethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1CCN1CCCCC1 SYPCCMJYEOWKPO-LVFSCSRESA-N 0.000 claims description 3
FEYZZDLGUROKMD-IUCKATPISA-N (1s,2s,3r,4r)-3-[[5-chloro-6-methyl-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=C(C)N=1)Cl)=NC=1NC=1C=NN(C)C=1 FEYZZDLGUROKMD-IUCKATPISA-N 0.000 claims description 3
QWYNGJJNJSVROV-IDCJVQTKSA-N (1s,2s,3r,4r)-3-[[5-fluoro-2-[[1-(2-pyrrolidin-1-ylethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)F)=NC=1NC(=C1)C=NN1CCN1CCCC1 QWYNGJJNJSVROV-IDCJVQTKSA-N 0.000 claims description 3
ACEMPAATJHNUIT-UHFFFAOYSA-N 1-[2-[[5-bromo-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]phenyl]cyclobutan-1-ol Chemical compound C1=NN(C)C=C1NC1=NC=C(Br)C(NC=2C(=CC=CC=2)C2(O)CCC2)=N1 ACEMPAATJHNUIT-UHFFFAOYSA-N 0.000 claims description 3
UKKNAPOKHCNTFA-PJQZNRQZSA-N 4-[[(1r,2r,3s,4s)-2-carbamoyl-3-bicyclo[2.2.1]hept-5-enyl]amino]-2-[(1-ethylpyrazol-4-yl)amino]pyrimidine-5-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=CN=1)C(N)=O)=NC=1NC=1C=NN(CC)C=1 UKKNAPOKHCNTFA-PJQZNRQZSA-N 0.000 claims description 3
MXTVKLJDGJCVDH-OPQQBVKSSA-N 4-n-[(1s,3r,4r)-3-bicyclo[2.2.1]heptanyl]-5-fluoro-2-n-(1-methylpyrazol-4-yl)pyrimidine-2,4-diamine Chemical compound N([C@H]1[C@]2([H])CC[C@@](C2)(C1)[H])C(C(=CN=1)F)=NC=1NC=1C=NN(C)C=1 MXTVKLJDGJCVDH-OPQQBVKSSA-N 0.000 claims description 3
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
BRLSBZVSFMZKHL-DRABBMOASA-N ethyl (1r,2r,3s,4s)-3-[[5-fluoro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxylate Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(=O)OCC)C(C(=CN=1)F)=NC=1NC=1C=NN(C)C=1 BRLSBZVSFMZKHL-DRABBMOASA-N 0.000 claims description 3
BRLSBZVSFMZKHL-FDRIWYBQSA-N ethyl (1s,2s,3r,4r)-3-[[5-fluoro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxylate Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(=O)OCC)C(C(=CN=1)F)=NC=1NC=1C=NN(C)C=1 BRLSBZVSFMZKHL-FDRIWYBQSA-N 0.000 claims description 3
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 3
ZGRUBCQSYPMBEM-PJQZNRQZSA-N (1r,2r,3s,4s)-3-[[2-[(1-ethylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=CN=1)C(F)(F)F)=NC=1NC=1C=NN(CC)C=1 ZGRUBCQSYPMBEM-PJQZNRQZSA-N 0.000 claims description 2
BBLIGVOVXFAKMZ-PJQZNRQZSA-N (1r,2r,3s,4s)-3-[[2-[(1-ethylpyrazol-4-yl)amino]-5-fluoropyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=CN=1)F)=NC=1NC=1C=NN(CC)C=1 BBLIGVOVXFAKMZ-PJQZNRQZSA-N 0.000 claims description 2
CLJUCVUFMWRGPQ-DRABBMOASA-N (1r,2r,3s,4s)-3-[[2-[(1-ethylpyrazol-4-yl)amino]-5-methoxypyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=CN=1)OC)=NC=1NC=1C=NN(CC)C=1 CLJUCVUFMWRGPQ-DRABBMOASA-N 0.000 claims description 2
QZOGIXIGMUOFQB-DTVLGXAZSA-N (1r,2r,3s,4s)-3-[[2-[(1-methylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]bicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])CC[C@]1(C2)[H])C(N)=O)C(C(=CN=1)C(F)(F)F)=NC=1NC=1C=NN(C)C=1 QZOGIXIGMUOFQB-DTVLGXAZSA-N 0.000 claims description 2
XNLHVDPDSQODGM-MXYBEHONSA-N (1r,2r,3s,4s)-3-[[2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]-5-methylpyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=CN=1)C)=NC=1NC=1C=NN(CCO)C=1 XNLHVDPDSQODGM-MXYBEHONSA-N 0.000 claims description 2
ABKPYKYMAYCYSR-DRABBMOASA-N (1r,2r,3s,4s)-3-[[5-bromo-2-[(1-ethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-n-methylbicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(=O)NC)C(C(=CN=1)Br)=NC=1NC=1C=NN(CC)C=1 ABKPYKYMAYCYSR-DRABBMOASA-N 0.000 claims description 2
CWGMUGAHFWGINC-PJQZNRQZSA-N (1r,2r,3s,4s)-3-[[5-bromo-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-n-methylbicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(=O)NC)C(C(=CN=1)Br)=NC=1NC=1C=NN(C)C=1 CWGMUGAHFWGINC-PJQZNRQZSA-N 0.000 claims description 2
GEATXDJAPAHPTP-ZFWZSOMGSA-N (1r,2r,3s,4s)-3-[[5-bromo-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Br)=NC=1NC=1C=NN(C)C=1 GEATXDJAPAHPTP-ZFWZSOMGSA-N 0.000 claims description 2
OWAQOZCUBJYFLS-JFTQMJAMSA-N (1r,2r,3s,4s)-3-[[5-bromo-2-[[1-(2-morpholin-4-ylethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Br)=NC=1NC(=C1)C=NN1CCN1CCOCC1 OWAQOZCUBJYFLS-JFTQMJAMSA-N 0.000 claims description 2
SLBMOFAXVDFCJG-JFTQMJAMSA-N (1r,2r,3s,4s)-3-[[5-bromo-2-[[1-(2-pyrrolidin-1-ylethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Br)=NC=1NC(=C1)C=NN1CCN1CCCC1 SLBMOFAXVDFCJG-JFTQMJAMSA-N 0.000 claims description 2
HFGWJQCDWDPUHN-QOBDMFJFSA-N (1r,2r,3s,4s)-3-[[5-chloro-2-[(1-ethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])CC[C@]1(C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CC)C=1 HFGWJQCDWDPUHN-QOBDMFJFSA-N 0.000 claims description 2
UWJZCHZNTUYAIM-PJQZNRQZSA-N (1r,2r,3s,4s)-3-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-n-methylbicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(=O)NC)C(C(=CN=1)Cl)=NC=1NC=1C=NN(C)C=1 UWJZCHZNTUYAIM-PJQZNRQZSA-N 0.000 claims description 2
MWVXACVVOSGAKF-ZFWZSOMGSA-N (1r,2r,3s,4s)-3-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(C)C=1 MWVXACVVOSGAKF-ZFWZSOMGSA-N 0.000 claims description 2
SIOVOFUZCZDZMI-DECQCQTCSA-N (1r,2r,3s,4s)-3-[[5-chloro-2-[[1-(1-methylpiperidin-4-yl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1C1CCN(C)CC1 SIOVOFUZCZDZMI-DECQCQTCSA-N 0.000 claims description 2
DHBAXUVVJZKEPD-JFTQMJAMSA-N (1r,2r,3s,4s)-3-[[5-chloro-2-[[1-(2-pyrrolidin-1-ylethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1CCN1CCCC1 DHBAXUVVJZKEPD-JFTQMJAMSA-N 0.000 claims description 2
FEYZZDLGUROKMD-SVBLFDIKSA-N (1r,2r,3s,4s)-3-[[5-chloro-6-methyl-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=C(C)N=1)Cl)=NC=1NC=1C=NN(C)C=1 FEYZZDLGUROKMD-SVBLFDIKSA-N 0.000 claims description 2
GAKPGDJOZZRZGE-PJQZNRQZSA-N (1r,2r,3s,4s)-3-[[5-fluoro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=CN=1)F)=NC=1NC=1C=NN(CCO)C=1 GAKPGDJOZZRZGE-PJQZNRQZSA-N 0.000 claims description 2
QWYNGJJNJSVROV-JFTQMJAMSA-N (1r,2r,3s,4s)-3-[[5-fluoro-2-[[1-(2-pyrrolidin-1-ylethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=CN=1)F)=NC=1NC(=C1)C=NN1CCN1CCCC1 QWYNGJJNJSVROV-JFTQMJAMSA-N 0.000 claims description 2
KWNQIKSDUIQHRX-PJQZNRQZSA-N (1r,2r,3s,4s)-3-[[5-methoxy-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=CN=1)OC)=NC=1NC=1C=NN(C)C=1 KWNQIKSDUIQHRX-PJQZNRQZSA-N 0.000 claims description 2
FXKGUMKUGJEBFI-UNJBNNCHSA-N (1r,2r,3s,4s)-3-[[5-methyl-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=CN=1)C)=NC=1NC=1C=NN(C)C=1 FXKGUMKUGJEBFI-UNJBNNCHSA-N 0.000 claims description 2
PLJWNSJCDIUAGM-SCZZXKLOSA-N (1r,2s)-2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]cyclobutane-1-carboxamide Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(N[C@@H]2[C@@H](CC2)C(N)=O)=N1 PLJWNSJCDIUAGM-SCZZXKLOSA-N 0.000 claims description 2
SRYOUBCWZIVZBY-PWSUYJOCSA-N (1r,2s)-2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]cyclohexane-1-carboxamide Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(N[C@@H]2[C@@H](CCCC2)C(N)=O)=N1 SRYOUBCWZIVZBY-PWSUYJOCSA-N 0.000 claims description 2
GLKZFXMRQZAEKL-HFLGISGGSA-N (1r,2s,3r,4s)-3-[[2-[[1-[(2r)-2-hydroxypropyl]pyrazol-4-yl]amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]bicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@H]1[C@H]([C@]2([H])CC[C@]1(C2)[H])C(N)=O)C(C(=CN=1)C(F)(F)F)=NC=1NC=1C=NN(C[C@@H](C)O)C=1 GLKZFXMRQZAEKL-HFLGISGGSA-N 0.000 claims description 2
XMAWJUOJKHIGND-XQHKEYJVSA-N (1r,2s,3r,4s)-3-[[5-chloro-2-[(1-ethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-7-oxabicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@@]2([H])CC[C@@]1(O2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CC)C=1 XMAWJUOJKHIGND-XQHKEYJVSA-N 0.000 claims description 2
WBVVEHDODCFLBV-GIFSMMMISA-N (1r,2s,3r,4s)-3-[[5-chloro-2-[(1-ethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CC)C=1 WBVVEHDODCFLBV-GIFSMMMISA-N 0.000 claims description 2
SCMNVDCXNVNNAF-KXNHARMFSA-N (1r,2s,3r,4s)-3-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-7-oxabicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@@]2([H])CC[C@@]1(O2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(C)C=1 SCMNVDCXNVNNAF-KXNHARMFSA-N 0.000 claims description 2
MWVXACVVOSGAKF-GAQJKIJGSA-N (1r,2s,3r,4s)-3-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(C)C=1 MWVXACVVOSGAKF-GAQJKIJGSA-N 0.000 claims description 2
IYEAGLHMVUYANW-IDCJVQTKSA-N (1r,2s,3r,4s)-3-[[5-chloro-2-[[1-(2-morpholin-4-ylethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@H]1[C@H]([C@]2([H])CC[C@]1(C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1CCN1CCOCC1 IYEAGLHMVUYANW-IDCJVQTKSA-N 0.000 claims description 2
SFGQLEJUSUUIOA-LZJQFABFSA-N (1r,2s,3r,4s)-3-[[5-chloro-2-[[1-[2-(dimethylamino)-2-oxoethyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@H]1[C@H]([C@]2([H])CC[C@]1(C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CC(=O)N(C)C)C=1 SFGQLEJUSUUIOA-LZJQFABFSA-N 0.000 claims description 2
SFUSDOKTIFUSPL-FIDNZITISA-N (1r,2s,3r,4s)-3-[[5-fluoro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@H]1[C@H]([C@]2([H])CC[C@]1(C2)[H])C(N)=O)C(C(=CN=1)F)=NC=1NC=1C=NN(C)C=1 SFUSDOKTIFUSPL-FIDNZITISA-N 0.000 claims description 2
LYPACVWRTQUYFR-XXSPCDMZSA-N (1r,2s,3r,4s)-3-[[5-fluoro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@H]1[C@H]([C@]2([H])CC[C@]1(C2)[H])C(N)=O)C(C(=CN=1)F)=NC=1NC=1C=NN(CCO)C=1 LYPACVWRTQUYFR-XXSPCDMZSA-N 0.000 claims description 2
MBBPYWUJBMAFFE-NHULGOKLSA-N (1r,3s,4r,5r)-4-[[2-[(1-ethylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]-6,6-dimethylbicyclo[3.1.1]heptane-3-carboxamide Chemical compound N([C@@H]1[C@@]2(C[C@](C[C@@H]1C(N)=O)(C2(C)C)[H])[H])C(C(=CN=1)C(F)(F)F)=NC=1NC=1C=NN(CC)C=1 MBBPYWUJBMAFFE-NHULGOKLSA-N 0.000 claims description 2
KAUKYDYNYGPGFX-ASHKBJFXSA-N (1r,3s,4r,5r)-4-[[5-bromo-2-[(1,5-dimethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-6,6-dimethylbicyclo[3.1.1]heptane-3-carboxamide Chemical compound N([C@@H]1[C@@]2(C[C@](C[C@@H]1C(N)=O)(C2(C)C)[H])[H])C(C(=CN=1)Br)=NC=1NC=1C=NN(C)C=1C KAUKYDYNYGPGFX-ASHKBJFXSA-N 0.000 claims description 2
AFZYWEXDYRWRIE-ASHKBJFXSA-N (1r,3s,4r,5r)-4-[[5-chloro-2-[(1,5-dimethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-6,6-dimethylbicyclo[3.1.1]heptane-3-carboxamide Chemical compound N([C@@H]1[C@@]2(C[C@](C[C@@H]1C(N)=O)(C2(C)C)[H])[H])C(C(=CN=1)Cl)=NC=1NC=1C=NN(C)C=1C AFZYWEXDYRWRIE-ASHKBJFXSA-N 0.000 claims description 2
FTPFUQLJUKWYDQ-NHULGOKLSA-N (1r,3s,4r,5r)-4-[[5-chloro-2-[(1-ethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-6,6-dimethylbicyclo[3.1.1]heptane-3-carboxamide Chemical compound N([C@@H]1[C@@]2(C[C@](C[C@@H]1C(N)=O)(C2(C)C)[H])[H])C(C(=CN=1)Cl)=NC=1NC=1C=NN(CC)C=1 FTPFUQLJUKWYDQ-NHULGOKLSA-N 0.000 claims description 2
OOGNRCFCEZGCIB-HVTMNAMFSA-N (1r,3s,4r,5r)-4-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-6,6-dimethylbicyclo[3.1.1]heptane-3-carboxamide Chemical compound N([C@@H]1[C@@]2(C[C@](C[C@@H]1C(N)=O)(C2(C)C)[H])[H])C(C(=CN=1)Cl)=NC=1NC=1C=NN(C)C=1 OOGNRCFCEZGCIB-HVTMNAMFSA-N 0.000 claims description 2
QUBSSCKDMYODIH-WBKMXMRLSA-N (1r,3s,4r,5r)-4-[[5-chloro-2-[[1-(2-phenylethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]-6,6-dimethylbicyclo[3.1.1]heptane-3-carboxamide Chemical compound N([C@@H]1[C@@]2(C[C@](C[C@@H]1C(N)=O)(C2(C)C)[H])[H])C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1CCC1=CC=CC=C1 QUBSSCKDMYODIH-WBKMXMRLSA-N 0.000 claims description 2
PLJWNSJCDIUAGM-WCBMZHEXSA-N (1s,2r)-2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]cyclobutane-1-carboxamide Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(N[C@H]2[C@H](CC2)C(N)=O)=N1 PLJWNSJCDIUAGM-WCBMZHEXSA-N 0.000 claims description 2
DJASEHPUPBAANK-PKOBYXMFSA-N (1s,2r)-2-[[5-chloro-2-[[1-(2-morpholin-4-ylethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]-n-propan-2-ylcyclopentane-1-carboxamide Chemical compound CC(C)NC(=O)[C@H]1CCC[C@H]1NC1=NC(NC2=CN(CCN3CCOCC3)N=C2)=NC=C1Cl DJASEHPUPBAANK-PKOBYXMFSA-N 0.000 claims description 2
UXXGXZAZZIYQFC-GXSJLCMTSA-N (1s,2r)-2-[[5-fluoro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]cyclopentane-1-carboxamide Chemical compound C1=NN(C)C=C1NC1=NC=C(F)C(N[C@H]2[C@H](CCC2)C(N)=O)=N1 UXXGXZAZZIYQFC-GXSJLCMTSA-N 0.000 claims description 2
OMCDXKNVARSHIM-PJQZNRQZSA-N (1s,2r,3s,4r)-3-[[2-[(1-ethylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]bicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@@]2([H])CC[C@@]1(C2)[H])C(N)=O)C(C(=CN=1)C(F)(F)F)=NC=1NC=1C=NN(CC)C=1 OMCDXKNVARSHIM-PJQZNRQZSA-N 0.000 claims description 2
CLPWEIYJUQKGRS-PJQZNRQZSA-N (1s,2r,3s,4r)-3-[[2-[(1-ethylpyrazol-4-yl)amino]-5-fluoropyrimidin-4-yl]amino]bicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@@]2([H])CC[C@@]1(C2)[H])C(N)=O)C(C(=CN=1)F)=NC=1NC=1C=NN(CC)C=1 CLPWEIYJUQKGRS-PJQZNRQZSA-N 0.000 claims description 2
GLKZFXMRQZAEKL-YHXLARSLSA-N (1s,2r,3s,4r)-3-[[2-[[1-[(2r)-2-hydroxypropyl]pyrazol-4-yl]amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]bicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@@]2([H])CC[C@@]1(C2)[H])C(N)=O)C(C(=CN=1)C(F)(F)F)=NC=1NC=1C=NN(C[C@@H](C)O)C=1 GLKZFXMRQZAEKL-YHXLARSLSA-N 0.000 claims description 2
XMAWJUOJKHIGND-QNWHQSFQSA-N (1s,2r,3s,4r)-3-[[5-chloro-2-[(1-ethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-7-oxabicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@H]1[C@H]([C@]2([H])CC[C@]1(O2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CC)C=1 XMAWJUOJKHIGND-QNWHQSFQSA-N 0.000 claims description 2
SCMNVDCXNVNNAF-WHOHXGKFSA-N (1s,2r,3s,4r)-3-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-7-oxabicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@H]1[C@H]([C@]2([H])CC[C@]1(O2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(C)C=1 SCMNVDCXNVNNAF-WHOHXGKFSA-N 0.000 claims description 2
BCRSULZZWCMCCI-PJQZNRQZSA-N (1s,2r,3s,4r)-3-[[5-chloro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@@]2([H])CC[C@@]1(C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CCO)C=1 BCRSULZZWCMCCI-PJQZNRQZSA-N 0.000 claims description 2
LYPACVWRTQUYFR-PJQZNRQZSA-N (1s,2r,3s,4r)-3-[[5-fluoro-2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@@]2([H])CC[C@@]1(C2)[H])C(N)=O)C(C(=CN=1)F)=NC=1NC=1C=NN(CCO)C=1 LYPACVWRTQUYFR-PJQZNRQZSA-N 0.000 claims description 2
VYNGUWKDKUXEGX-YHXLARSLSA-N (1s,2r,3s,4r)-3-[[5-fluoro-2-[[1-[(2r)-2-hydroxypropyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@@]2([H])CC[C@@]1(C2)[H])C(N)=O)C(C(=CN=1)F)=NC=1NC=1C=NN(C[C@@H](C)O)C=1 VYNGUWKDKUXEGX-YHXLARSLSA-N 0.000 claims description 2
UANHXIDLXDOQFC-LVFSCSRESA-N (1s,2s,3r,4r)-3-[[2-[(1-benzylpyrazol-4-yl)amino]-5-bromopyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Br)=NC=1NC(=C1)C=NN1CC1=CC=CC=C1 UANHXIDLXDOQFC-LVFSCSRESA-N 0.000 claims description 2
ZGMGZBILRTWEQE-LVFSCSRESA-N (1s,2s,3r,4r)-3-[[2-[(1-benzylpyrazol-4-yl)amino]-5-chloropyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1CC1=CC=CC=C1 ZGMGZBILRTWEQE-LVFSCSRESA-N 0.000 claims description 2
CLJUCVUFMWRGPQ-FDRIWYBQSA-N (1s,2s,3r,4r)-3-[[2-[(1-ethylpyrazol-4-yl)amino]-5-methoxypyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)OC)=NC=1NC=1C=NN(CC)C=1 CLJUCVUFMWRGPQ-FDRIWYBQSA-N 0.000 claims description 2
PWKFHFJMEIOZJI-XXSPCDMZSA-N (1s,2s,3r,4r)-3-[[2-[(1-ethylpyrazol-4-yl)amino]-5-nitropyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)[N+]([O-])=O)=NC=1NC=1C=NN(CC)C=1 PWKFHFJMEIOZJI-XXSPCDMZSA-N 0.000 claims description 2
RKUJYVCXPDDJQR-FIDNZITISA-N (1s,2s,3r,4r)-3-[[2-[(1-methylpyrazol-4-yl)amino]-5-nitropyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)[N+]([O-])=O)=NC=1NC=1C=NN(C)C=1 RKUJYVCXPDDJQR-FIDNZITISA-N 0.000 claims description 2
UTENPHLXRWYSHC-OBPYKSBLSA-N (1s,2s,3r,4r)-3-[[2-[[1-(2-amino-2-oxoethyl)pyrazol-4-yl]amino]-5-bromopyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Br)=NC=1NC=1C=NN(CC(N)=O)C=1 UTENPHLXRWYSHC-OBPYKSBLSA-N 0.000 claims description 2
BLZWXBSUDSBCGN-LZJQFABFSA-N (1s,2s,3r,4r)-3-[[5-bromo-2-[(1-cyclobutylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Br)=NC=1NC(=C1)C=NN1C1CCC1 BLZWXBSUDSBCGN-LZJQFABFSA-N 0.000 claims description 2
ABKPYKYMAYCYSR-FDRIWYBQSA-N (1s,2s,3r,4r)-3-[[5-bromo-2-[(1-ethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-n-methylbicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(=O)NC)C(C(=CN=1)Br)=NC=1NC=1C=NN(CC)C=1 ABKPYKYMAYCYSR-FDRIWYBQSA-N 0.000 claims description 2
WRPPDGMHYOTTHF-XLQHLMKVSA-N (1s,2s,3r,4r)-3-[[5-bromo-2-[(1-phenylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Br)=NC=1NC(=C1)C=NN1C1=CC=CC=C1 WRPPDGMHYOTTHF-XLQHLMKVSA-N 0.000 claims description 2
OWAQOZCUBJYFLS-IDCJVQTKSA-N (1s,2s,3r,4r)-3-[[5-bromo-2-[[1-(2-morpholin-4-ylethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Br)=NC=1NC(=C1)C=NN1CCN1CCOCC1 OWAQOZCUBJYFLS-IDCJVQTKSA-N 0.000 claims description 2
AFGBUZJUAJPTIJ-OSRSDYAFSA-N (1s,2s,3r,4r)-3-[[5-bromo-2-[[1-(3-methylbutyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Br)=NC=1NC=1C=NN(CCC(C)C)C=1 AFGBUZJUAJPTIJ-OSRSDYAFSA-N 0.000 claims description 2
SWQJVWHJSHOBLM-BBNYVJOESA-N (1s,2s,3r,4r)-3-[[5-bromo-2-[[1-[(3-fluoro-4-methoxyphenyl)methyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Br)=NC=1NC(=C1)C=NN1CC1=CC=C(OC)C(F)=C1 SWQJVWHJSHOBLM-BBNYVJOESA-N 0.000 claims description 2
FOVGZVOGVFBAAL-SPLQCWDRSA-N (1s,2s,3r,4r)-3-[[5-bromo-2-[[1-[(4-chlorophenyl)methyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Br)=NC=1NC(=C1)C=NN1CC1=CC=C(Cl)C=C1 FOVGZVOGVFBAAL-SPLQCWDRSA-N 0.000 claims description 2
HFGWJQCDWDPUHN-GIFSMMMISA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])CC[C@@]1(C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CC)C=1 HFGWJQCDWDPUHN-GIFSMMMISA-N 0.000 claims description 2
NJEJIUSXRRPGIL-GAQJKIJGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])CC[C@@]1(C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(C)C=1 NJEJIUSXRRPGIL-GAQJKIJGSA-N 0.000 claims description 2
OMWMPZGMUGILKY-XLQHLMKVSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-phenylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1C1=CC=CC=C1 OMWMPZGMUGILKY-XLQHLMKVSA-N 0.000 claims description 2
SIOVOFUZCZDZMI-XLQHLMKVSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[1-(1-methylpiperidin-4-yl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1C1CCN(C)CC1 SIOVOFUZCZDZMI-XLQHLMKVSA-N 0.000 claims description 2
HJDPGFOOQDBCFV-FIDNZITISA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[1-(2,2,2-trifluoroethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CC(F)(F)F)C=1 HJDPGFOOQDBCFV-FIDNZITISA-N 0.000 claims description 2
VWNWNXCVJAUZBJ-IDCJVQTKSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[1-(2-morpholin-4-ylethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1CCN1CCOCC1 VWNWNXCVJAUZBJ-IDCJVQTKSA-N 0.000 claims description 2
WVFYPDLSPLCZON-CQIJRDABSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[1-(naphthalen-2-ylmethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound C1=CC=CC2=CC(CN3N=CC(=C3)NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 WVFYPDLSPLCZON-CQIJRDABSA-N 0.000 claims description 2
QHRBKEQGUHLWCZ-XHNXPPCKSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[1-(oxetan-2-ylmethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1CC1CCO1 QHRBKEQGUHLWCZ-XHNXPPCKSA-N 0.000 claims description 2
CWHDUSLJLYNZNZ-MTZMYHNQSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[1-[(2-chlorophenyl)methyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1CC1=CC=CC=C1Cl CWHDUSLJLYNZNZ-MTZMYHNQSA-N 0.000 claims description 2
HYIKMTXGNDEFBK-SPLQCWDRSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[1-[(3-chlorophenyl)methyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1CC1=CC=CC(Cl)=C1 HYIKMTXGNDEFBK-SPLQCWDRSA-N 0.000 claims description 2
PGBNFIBSIHDVLJ-GIYDNNGJSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[1-[(3-methylphenyl)methyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1CC1=CC=CC(C)=C1 PGBNFIBSIHDVLJ-GIYDNNGJSA-N 0.000 claims description 2
ZRVAUKWSHYGLFI-SPLQCWDRSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[1-[(4-chlorophenyl)methyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1CC1=CC=C(Cl)C=C1 ZRVAUKWSHYGLFI-SPLQCWDRSA-N 0.000 claims description 2
AFOBLTYAFYZQBR-UGCQDJOBSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[1-[1-[2-(dimethylamino)acetyl]piperidin-4-yl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1C1CCN(C(=O)CN(C)C)CC1 AFOBLTYAFYZQBR-UGCQDJOBSA-N 0.000 claims description 2
WHDZRHLPGYRKOD-UFGYURQFSA-N (1s,2s,3r,4r)-3-[[5-fluoro-2-(1h-pyrazol-4-ylamino)pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)F)=NC=1NC=1C=NNC=1 WHDZRHLPGYRKOD-UFGYURQFSA-N 0.000 claims description 2
HWPSHUSYXFAEGR-FIDNZITISA-N (1s,2s,3r,4r)-3-[[5-fluoro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)F)=NC=1NC=1C=NN(C)C=1 HWPSHUSYXFAEGR-FIDNZITISA-N 0.000 claims description 2
KWNQIKSDUIQHRX-XXSPCDMZSA-N (1s,2s,3r,4r)-3-[[5-methoxy-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)OC)=NC=1NC=1C=NN(C)C=1 KWNQIKSDUIQHRX-XXSPCDMZSA-N 0.000 claims description 2
FXKGUMKUGJEBFI-UVLXDEKHSA-N (1s,2s,3r,4r)-3-[[5-methyl-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)C)=NC=1NC=1C=NN(C)C=1 FXKGUMKUGJEBFI-UVLXDEKHSA-N 0.000 claims description 2
YWZGAGXMSIOYIX-UHFFFAOYSA-N 1-[2-[[2-[(1-methylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]phenyl]cyclobutan-1-ol Chemical compound C1=NN(C)C=C1NC1=NC=C(C(F)(F)F)C(NC=2C(=CC=CC=2)C2(O)CCC2)=N1 YWZGAGXMSIOYIX-UHFFFAOYSA-N 0.000 claims description 2
CKTOGCUGKAJSJR-UHFFFAOYSA-N 1-methyl-4-[[2-[(1-methylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]pyrazole-3-carboxamide Chemical compound C1=NN(C)C=C1NC1=NC=C(C(F)(F)F)C(NC=2C(=NN(C)C=2)C(N)=O)=N1 CKTOGCUGKAJSJR-UHFFFAOYSA-N 0.000 claims description 2
QYQLAHVYGBJXDH-OBPYKSBLSA-N 2-[4-[[4-[[(1s,2s,3r,4r)-2-carbamoyl-3-bicyclo[2.2.1]hept-5-enyl]amino]-5-chloropyrimidin-2-yl]amino]pyrazol-1-yl]acetic acid Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CC(O)=O)C=1 QYQLAHVYGBJXDH-OBPYKSBLSA-N 0.000 claims description 2
IGIOOVRVTXQENG-UHFFFAOYSA-N 2-[[2-[(1-methylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]thiophene-3-carboxamide Chemical compound C1=NN(C)C=C1NC1=NC=C(C(F)(F)F)C(NC2=C(C=CS2)C(N)=O)=N1 IGIOOVRVTXQENG-UHFFFAOYSA-N 0.000 claims description 2
HYNAMEOYEGNYAC-UHFFFAOYSA-N 3-[2-[[2-[(1-methylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]phenyl]azetidin-3-ol Chemical compound C1=NN(C)C=C1NC1=NC=C(C(F)(F)F)C(NC=2C(=CC=CC=2)C2(O)CNC2)=N1 HYNAMEOYEGNYAC-UHFFFAOYSA-N 0.000 claims description 2
RCYQPRWVJXRKLU-UHFFFAOYSA-N 3-[[2-[(1-methylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]thiophene-2-carboxamide Chemical compound C1=NN(C)C=C1NC1=NC=C(C(F)(F)F)C(NC2=C(SC=C2)C(N)=O)=N1 RCYQPRWVJXRKLU-UHFFFAOYSA-N 0.000 claims description 2
ZOFMFMNMMNYFRG-UHFFFAOYSA-N 4-[2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]phenyl]oxan-4-ol Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC=2C(=CC=CC=2)C2(O)CCOCC2)=N1 ZOFMFMNMMNYFRG-UHFFFAOYSA-N 0.000 claims description 2
LEYQOXSFRMBVRT-ZFWZSOMGSA-N 4-[[(1r,2r,3s,4s)-2-carbamoyl-3-bicyclo[2.2.1]hept-5-enyl]amino]-2-[(1-methylpyrazol-4-yl)amino]pyrimidine-5-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=CN=1)C(N)=O)=NC=1NC=1C=NN(C)C=1 LEYQOXSFRMBVRT-ZFWZSOMGSA-N 0.000 claims description 2
UKKNAPOKHCNTFA-XXSPCDMZSA-N 4-[[(1s,2s,3r,4r)-2-carbamoyl-3-bicyclo[2.2.1]hept-5-enyl]amino]-2-[(1-ethylpyrazol-4-yl)amino]pyrimidine-5-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)C(N)=O)=NC=1NC=1C=NN(CC)C=1 UKKNAPOKHCNTFA-XXSPCDMZSA-N 0.000 claims description 2
LEYQOXSFRMBVRT-FIDNZITISA-N 4-[[(1s,2s,3r,4r)-2-carbamoyl-3-bicyclo[2.2.1]hept-5-enyl]amino]-2-[(1-methylpyrazol-4-yl)amino]pyrimidine-5-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)C(N)=O)=NC=1NC=1C=NN(C)C=1 LEYQOXSFRMBVRT-FIDNZITISA-N 0.000 claims description 2
RDFBXLTVSCZKAQ-NRUUGDAUSA-N 4-n-[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]-2-n-(1-methylpyrazol-4-yl)-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(C(=CN=1)C(F)(F)F)=NC=1NC=1C=NN(C)C=1 RDFBXLTVSCZKAQ-NRUUGDAUSA-N 0.000 claims description 2
MXTVKLJDGJCVDH-NRUUGDAUSA-N 4-n-[(1r,3s,4s)-3-bicyclo[2.2.1]heptanyl]-5-fluoro-2-n-(1-methylpyrazol-4-yl)pyrimidine-2,4-diamine Chemical compound N([C@@H]1[C@@]2([H])CC[C@](C2)(C1)[H])C(C(=CN=1)F)=NC=1NC=1C=NN(C)C=1 MXTVKLJDGJCVDH-NRUUGDAUSA-N 0.000 claims description 2
NWXWUGBTGKLUSJ-UHFFFAOYSA-N 5-bromo-2-n-(1-ethylpyrazol-4-yl)-2-n-(1h-indazol-5-yl)pyrimidine-2,4-diamine Chemical compound C1=NN(CC)C=C1N(C=1N=C(N)C(Br)=CN=1)C1=CC=C(NN=C2)C2=C1 NWXWUGBTGKLUSJ-UHFFFAOYSA-N 0.000 claims description 2
IUIGCIYQEQMDLR-UHFFFAOYSA-N 5-chloro-2-n-(1-ethylpyrazol-4-yl)-4-n-(1h-indazol-5-yl)pyrimidine-2,4-diamine Chemical compound C1=NN(CC)C=C1NC1=NC=C(Cl)C(NC=2C=C3C=NNC3=CC=2)=N1 IUIGCIYQEQMDLR-UHFFFAOYSA-N 0.000 claims description 2
CQGUJQNQCRSZMD-UHFFFAOYSA-N 5-chloro-2-n-(1h-indazol-5-yl)-2-n-[1-(2-pyrrolidin-1-ylethyl)pyrazol-4-yl]pyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(N)=NC(N(C2=CN(CCN3CCCC3)N=C2)C=2C=C3C=NNC3=CC=2)=N1 CQGUJQNQCRSZMD-UHFFFAOYSA-N 0.000 claims description 2
DMHIOKGPIMIGBU-CYBMUJFWSA-N 5-chloro-2-n-(1h-indazol-5-yl)-2-n-[1-[(3r)-pyrrolidin-3-yl]pyrazol-4-yl]pyrimidine-2,4-diamine Chemical compound C1=C(Cl)C(N)=NC(N(C2=CN(N=C2)[C@H]2CNCC2)C=2C=C3C=NNC3=CC=2)=N1 DMHIOKGPIMIGBU-CYBMUJFWSA-N 0.000 claims description 2
BHNOJVWXPAIWCZ-UHFFFAOYSA-N 5-chloro-2-n-(1h-indazol-5-yl)-2-n-[1-[2-(4-methylpiperazin-1-yl)ethyl]pyrazol-4-yl]pyrimidine-2,4-diamine Chemical compound C1CN(C)CCN1CCN1N=CC(N(C=2C=C3C=NNC3=CC=2)C=2N=C(N)C(Cl)=CN=2)=C1 BHNOJVWXPAIWCZ-UHFFFAOYSA-N 0.000 claims description 2
OHIIDHVAVXSMDA-UHFFFAOYSA-N 5-chloro-4-n-(1h-indazol-5-yl)-2-n-(1-methylpyrazol-4-yl)pyrimidine-2,4-diamine Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC=2C=C3C=NNC3=CC=2)=N1 OHIIDHVAVXSMDA-UHFFFAOYSA-N 0.000 claims description 2
CRBHUUMFIXCJNV-UHFFFAOYSA-N [2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]phenyl]methanol Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC=2C(=CC=CC=2)CO)=N1 CRBHUUMFIXCJNV-UHFFFAOYSA-N 0.000 claims description 2
RHJVIGLEIFVHIJ-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1[CH]CCCC1 RHJVIGLEIFVHIJ-UHFFFAOYSA-N 0.000 claims description 2
230000003247 decreasing effect Effects 0.000 claims description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
HYZWBHXXZCXBBJ-SONRMIBWSA-N propan-2-yl 2-[4-[[5-bromo-4-[[(1S,2S,3R,4R)-3-carbamoyl-2-bicyclo[2.2.1]hept-5-enyl]amino]pyrimidin-2-yl]amino]pyrazol-1-yl]acetate Chemical compound C(C)(C)OC(CN1N=CC(=C1)NC1=NC=C(C(=N1)N[C@H]1[C@@H]2C=C[C@H]([C@H]1C(=O)N)C2)Br)=O HYZWBHXXZCXBBJ-SONRMIBWSA-N 0.000 claims description 2
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 17
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
YXTKSHOEFGQFDH-FIDNZITISA-N (1s,2s,3r,4r)-3-[[2-[[1-(2,2,2-trifluoroethyl)pyrazol-4-yl]amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)C(F)(F)F)=NC=1NC=1C=NN(CC(F)(F)F)C=1 YXTKSHOEFGQFDH-FIDNZITISA-N 0.000 claims 2
UYZYFDSCOORBNH-XXSPCDMZSA-N (1s,2s,3r,4r)-3-[[2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)C(F)(F)F)=NC=1NC=1C=NN(CCO)C=1 UYZYFDSCOORBNH-XXSPCDMZSA-N 0.000 claims 2
GFIISANGXWSSNI-HFLGISGGSA-N (1s,2s,3r,4r)-3-[[2-[[1-[(2r)-2-hydroxypropyl]pyrazol-4-yl]amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)C(F)(F)F)=NC=1NC=1C=NN(C[C@@H](C)O)C=1 GFIISANGXWSSNI-HFLGISGGSA-N 0.000 claims 2
ZRQVUHCWSMAPRC-ZFWZSOMGSA-N (1r,2r,3s,4s)-3-[[2-[(1-methylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=CN=1)C(F)(F)F)=NC=1NC=1C=NN(C)C=1 ZRQVUHCWSMAPRC-ZFWZSOMGSA-N 0.000 claims 1
YXTKSHOEFGQFDH-ZFWZSOMGSA-N (1r,2r,3s,4s)-3-[[2-[[1-(2,2,2-trifluoroethyl)pyrazol-4-yl]amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=CN=1)C(F)(F)F)=NC=1NC=1C=NN(CC(F)(F)F)C=1 YXTKSHOEFGQFDH-ZFWZSOMGSA-N 0.000 claims 1
UYZYFDSCOORBNH-PJQZNRQZSA-N (1r,2r,3s,4s)-3-[[2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=CN=1)C(F)(F)F)=NC=1NC=1C=NN(CCO)C=1 UYZYFDSCOORBNH-PJQZNRQZSA-N 0.000 claims 1
GFIISANGXWSSNI-YHXLARSLSA-N (1r,2r,3s,4s)-3-[[2-[[1-[(2r)-2-hydroxypropyl]pyrazol-4-yl]amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=CN=1)C(F)(F)F)=NC=1NC=1C=NN(C[C@@H](C)O)C=1 GFIISANGXWSSNI-YHXLARSLSA-N 0.000 claims 1
NPJVSEXPCJZQAI-PJQZNRQZSA-N (1r,2r,3s,4s)-3-[[5-bromo-2-[(1-ethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Br)=NC=1NC=1C=NN(CC)C=1 NPJVSEXPCJZQAI-PJQZNRQZSA-N 0.000 claims 1
NCIAUWBSJNZFII-MDHDOXDCSA-N (1r,2r,3s,4s)-3-[[5-chloro-2-[(1-ethylpyrazol-4-yl)amino]-6-methylpyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=C(C)N=1)Cl)=NC=1NC=1C=NN(CC)C=1 NCIAUWBSJNZFII-MDHDOXDCSA-N 0.000 claims 1
GWAODKLMHUOUEN-DRABBMOASA-N (1r,2r,3s,4s)-3-[[5-chloro-2-[(1-ethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-n-methylbicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(=O)NC)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CC)C=1 GWAODKLMHUOUEN-DRABBMOASA-N 0.000 claims 1
WBVVEHDODCFLBV-PJQZNRQZSA-N (1r,2r,3s,4s)-3-[[5-chloro-2-[(1-ethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CC)C=1 WBVVEHDODCFLBV-PJQZNRQZSA-N 0.000 claims 1
FPEVYKSDIDVQGW-JFTQMJAMSA-N (1r,2r,3s,4s)-3-[[5-chloro-2-[[1-[2-(diethylamino)ethyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CCN(CC)CC)C=1 FPEVYKSDIDVQGW-JFTQMJAMSA-N 0.000 claims 1
YDEMQAAYOCNYEP-TZCMFKBTSA-N (1r,2r,3s,4s)-3-[[5-chloro-2-[[1-[2-(dimethylamino)-2-oxoethyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CC(=O)N(C)C)C=1 YDEMQAAYOCNYEP-TZCMFKBTSA-N 0.000 claims 1
STBMZODYQLKFRA-OJDYBEQGSA-N (1r,2r,3s,4s)-3-[[5-chloro-2-[[1-[2-(dimethylamino)ethyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CCN(C)C)C=1 STBMZODYQLKFRA-OJDYBEQGSA-N 0.000 claims 1
MNGDJFQVLRLXMO-PJQZNRQZSA-N (1r,2r,3s,4s)-3-[[5-fluoro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-n-methylbicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(=O)NC)C(C(=CN=1)F)=NC=1NC=1C=NN(C)C=1 MNGDJFQVLRLXMO-PJQZNRQZSA-N 0.000 claims 1
HWPSHUSYXFAEGR-ZFWZSOMGSA-N (1r,2r,3s,4s)-3-[[5-fluoro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=CN=1)F)=NC=1NC=1C=NN(C)C=1 HWPSHUSYXFAEGR-ZFWZSOMGSA-N 0.000 claims 1
YVSLWXDYSJAARW-YHXLARSLSA-N (1r,2r,3s,4s)-3-[[5-fluoro-2-[[1-[(2r)-2-hydroxypropyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=CN=1)F)=NC=1NC=1C=NN(C[C@@H](C)O)C=1 YVSLWXDYSJAARW-YHXLARSLSA-N 0.000 claims 1
FENCJVFWPSBLSH-SONRMIBWSA-N (1r,2r,3s,4s)-n-cyclopropyl-3-[[2-[(1-ethylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(=O)NC1CC1)C(C(=CN=1)C(F)(F)F)=NC=1NC=1C=NN(CC)C=1 FENCJVFWPSBLSH-SONRMIBWSA-N 0.000 claims 1
CIXLLNNDLZVHIJ-TZCMFKBTSA-N (1r,2r,3s,4s)-n-cyclopropyl-3-[[2-[(1-methylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(=O)NC1CC1)C(C(=CN=1)C(F)(F)F)=NC=1NC=1C=NN(C)C=1 CIXLLNNDLZVHIJ-TZCMFKBTSA-N 0.000 claims 1
XXHKWYBEHKUWRK-PJQZNRQZSA-N (1r,2r,3s,4s)-n-methyl-3-[[2-[(1-methylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(=O)NC)C(C(=CN=1)C(F)(F)F)=NC=1NC=1C=NN(C)C=1 XXHKWYBEHKUWRK-PJQZNRQZSA-N 0.000 claims 1
UZIAHPQGCHFFCM-KOLCDFICSA-N (1r,2s)-2-[[2-[(1-methylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]cyclopentane-1-carboxamide Chemical compound C1=NN(C)C=C1NC1=NC=C(C(F)(F)F)C(N[C@@H]2[C@@H](CCC2)C(N)=O)=N1 UZIAHPQGCHFFCM-KOLCDFICSA-N 0.000 claims 1
GWMDBUDQQOBGQJ-AEFFLSMTSA-N (1r,2s)-2-[[5-chloro-2-[(1-piperidin-4-ylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-n-propan-2-ylcyclopentane-1-carboxamide Chemical compound CC(C)NC(=O)[C@@H]1CCC[C@@H]1NC1=NC(NC2=CN(N=C2)C2CCNCC2)=NC=C1Cl GWMDBUDQQOBGQJ-AEFFLSMTSA-N 0.000 claims 1
XMLNCRQQYIBBSN-HIFRSBDPSA-N (1r,2s)-2-[[5-chloro-2-[(1-piperidin-4-ylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]cyclopentane-1-carboxamide Chemical compound NC(=O)[C@@H]1CCC[C@@H]1NC1=NC(NC2=CN(N=C2)C2CCNCC2)=NC=C1Cl XMLNCRQQYIBBSN-HIFRSBDPSA-N 0.000 claims 1
YDNNPXSCJQXKJA-ZBFHGGJFSA-N (1r,2s)-2-[[5-chloro-2-[[1-(2-morpholin-4-ylethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]cyclopentane-1-carboxamide Chemical compound NC(=O)[C@@H]1CCC[C@@H]1NC1=NC(NC2=CN(CCN3CCOCC3)N=C2)=NC=C1Cl YDNNPXSCJQXKJA-ZBFHGGJFSA-N 0.000 claims 1
CSFTTYMQZRQSQW-HFLGISGGSA-N (1r,2s,3r,4s)-3-[[5-chloro-2-[[1-[(2r)-2-hydroxypropyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@H]1[C@H]([C@]2([H])CC[C@]1(C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(C[C@@H](C)O)C=1 CSFTTYMQZRQSQW-HFLGISGGSA-N 0.000 claims 1
VYNGUWKDKUXEGX-HFLGISGGSA-N (1r,2s,3r,4s)-3-[[5-fluoro-2-[[1-[(2r)-2-hydroxypropyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@H]1[C@H]([C@]2([H])CC[C@]1(C2)[H])C(N)=O)C(C(=CN=1)F)=NC=1NC=1C=NN(C[C@@H](C)O)C=1 VYNGUWKDKUXEGX-HFLGISGGSA-N 0.000 claims 1
CJAJMGUMLOTWGT-CAIZAGQASA-N (1r,3s,4r,5r)-4-[[2-[(1-benzylpyrazol-4-yl)amino]-5-chloropyrimidin-4-yl]amino]-6,6-dimethylbicyclo[3.1.1]heptane-3-carboxamide Chemical compound N([C@@H]1[C@@]2(C[C@](C[C@@H]1C(N)=O)(C2(C)C)[H])[H])C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1CC1=CC=CC=C1 CJAJMGUMLOTWGT-CAIZAGQASA-N 0.000 claims 1
CIGRIEGEDCMUHK-NHULGOKLSA-N (1r,3s,4r,5r)-4-[[5-bromo-2-[(1-ethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-6,6-dimethylbicyclo[3.1.1]heptane-3-carboxamide Chemical compound N([C@@H]1[C@@]2(C[C@](C[C@@H]1C(N)=O)(C2(C)C)[H])[H])C(C(=CN=1)Br)=NC=1NC=1C=NN(CC)C=1 CIGRIEGEDCMUHK-NHULGOKLSA-N 0.000 claims 1
MLJXMKZJTKIICS-HVTMNAMFSA-N (1r,3s,4r,5r)-4-[[5-bromo-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-6,6-dimethylbicyclo[3.1.1]heptane-3-carboxamide Chemical compound N([C@@H]1[C@@]2(C[C@](C[C@@H]1C(N)=O)(C2(C)C)[H])[H])C(C(=CN=1)Br)=NC=1NC=1C=NN(C)C=1 MLJXMKZJTKIICS-HVTMNAMFSA-N 0.000 claims 1
YQNDYEMYIMOXGR-UHEFJODHSA-N (1r,3s,4r,5r)-4-[[5-chloro-2-[(1-phenylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-6,6-dimethylbicyclo[3.1.1]heptane-3-carboxamide Chemical compound N([C@@H]1[C@@]2(C[C@](C[C@@H]1C(N)=O)(C2(C)C)[H])[H])C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1C1=CC=CC=C1 YQNDYEMYIMOXGR-UHEFJODHSA-N 0.000 claims 1
VNQSHTJHQRSLAG-RPZXMPESSA-N (1r,3s,4r,5r)-4-[[5-chloro-2-[(1-piperidin-4-ylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-6,6-dimethylbicyclo[3.1.1]heptane-3-carboxamide Chemical compound N([C@@H]1[C@@]2(C[C@](C[C@@H]1C(N)=O)(C2(C)C)[H])[H])C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1C1CCNCC1 VNQSHTJHQRSLAG-RPZXMPESSA-N 0.000 claims 1
QGZHGDKWJHKAEZ-PWSUYJOCSA-N (1r,6s)-6-[[2-[(1-methylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]cyclohex-3-ene-1-carboxamide Chemical compound C1=NN(C)C=C1NC1=NC=C(C(F)(F)F)C(N[C@@H]2[C@@H](CC=CC2)C(N)=O)=N1 QGZHGDKWJHKAEZ-PWSUYJOCSA-N 0.000 claims 1
UZIAHPQGCHFFCM-GXSJLCMTSA-N (1s,2r)-2-[[2-[(1-methylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]cyclopentane-1-carboxamide Chemical compound C1=NN(C)C=C1NC1=NC=C(C(F)(F)F)C(N[C@H]2[C@H](CCC2)C(N)=O)=N1 UZIAHPQGCHFFCM-GXSJLCMTSA-N 0.000 claims 1
GWMDBUDQQOBGQJ-FUHWJXTLSA-N (1s,2r)-2-[[5-chloro-2-[(1-piperidin-4-ylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-n-propan-2-ylcyclopentane-1-carboxamide Chemical compound CC(C)NC(=O)[C@H]1CCC[C@H]1NC1=NC(NC2=CN(N=C2)C2CCNCC2)=NC=C1Cl GWMDBUDQQOBGQJ-FUHWJXTLSA-N 0.000 claims 1
YDNNPXSCJQXKJA-GOEBONIOSA-N (1s,2r)-2-[[5-chloro-2-[[1-(2-morpholin-4-ylethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]cyclopentane-1-carboxamide Chemical compound NC(=O)[C@H]1CCC[C@H]1NC1=NC(NC2=CN(CCN3CCOCC3)N=C2)=NC=C1Cl YDNNPXSCJQXKJA-GOEBONIOSA-N 0.000 claims 1
HFGWJQCDWDPUHN-PJQZNRQZSA-N (1s,2r,3s,4r)-3-[[5-chloro-2-[(1-ethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@@]2([H])CC[C@@]1(C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CC)C=1 HFGWJQCDWDPUHN-PJQZNRQZSA-N 0.000 claims 1
MWVXACVVOSGAKF-DTVLGXAZSA-N (1s,2r,3s,4r)-3-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(C)C=1 MWVXACVVOSGAKF-DTVLGXAZSA-N 0.000 claims 1
NJEJIUSXRRPGIL-ZFWZSOMGSA-N (1s,2r,3s,4r)-3-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@@]2([H])CC[C@@]1(C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(C)C=1 NJEJIUSXRRPGIL-ZFWZSOMGSA-N 0.000 claims 1
IYEAGLHMVUYANW-JFTQMJAMSA-N (1s,2r,3s,4r)-3-[[5-chloro-2-[[1-(2-morpholin-4-ylethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@@]2([H])CC[C@@]1(C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1CCN1CCOCC1 IYEAGLHMVUYANW-JFTQMJAMSA-N 0.000 claims 1
SFGQLEJUSUUIOA-TZCMFKBTSA-N (1s,2r,3s,4r)-3-[[5-chloro-2-[[1-[2-(dimethylamino)-2-oxoethyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@@]2([H])CC[C@@]1(C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CC(=O)N(C)C)C=1 SFGQLEJUSUUIOA-TZCMFKBTSA-N 0.000 claims 1
LDQOJMLOGCBLQT-RZCHIYRCSA-N (1s,2r,3s,4r)-3-[[5-chloro-2-[[1-[2-(methylamino)-2-oxoethyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@@]2([H])CC[C@@]1(C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CC(=O)NC)C=1 LDQOJMLOGCBLQT-RZCHIYRCSA-N 0.000 claims 1
SFUSDOKTIFUSPL-ZFWZSOMGSA-N (1s,2r,3s,4r)-3-[[5-fluoro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@@]2([H])CC[C@@]1(C2)[H])C(N)=O)C(C(=CN=1)F)=NC=1NC=1C=NN(C)C=1 SFUSDOKTIFUSPL-ZFWZSOMGSA-N 0.000 claims 1
ZGRUBCQSYPMBEM-XXSPCDMZSA-N (1s,2s,3r,4r)-3-[[2-[(1-ethylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)C(F)(F)F)=NC=1NC=1C=NN(CC)C=1 ZGRUBCQSYPMBEM-XXSPCDMZSA-N 0.000 claims 1
ZRQVUHCWSMAPRC-FIDNZITISA-N (1s,2s,3r,4r)-3-[[2-[(1-methylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)C(F)(F)F)=NC=1NC=1C=NN(C)C=1 ZRQVUHCWSMAPRC-FIDNZITISA-N 0.000 claims 1
QZOGIXIGMUOFQB-GAQJKIJGSA-N (1s,2s,3r,4r)-3-[[2-[(1-methylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]bicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])CC[C@@]1(C2)[H])C(N)=O)C(C(=CN=1)C(F)(F)F)=NC=1NC=1C=NN(C)C=1 QZOGIXIGMUOFQB-GAQJKIJGSA-N 0.000 claims 1
MANTWCDJRBWNFR-XXSPCDMZSA-N (1s,2s,3r,4r)-3-[[2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(N=1)=CC=NC=1NC=1C=NN(C)C=1 MANTWCDJRBWNFR-XXSPCDMZSA-N 0.000 claims 1
IWLYXZXCMJQSPM-XXSPCDMZSA-N (1s,2s,3r,4r)-3-[[5-bromo-2-[(1,5-dimethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Br)=NC=1NC=1C=NN(C)C=1C IWLYXZXCMJQSPM-XXSPCDMZSA-N 0.000 claims 1
CWGMUGAHFWGINC-XXSPCDMZSA-N (1s,2s,3r,4r)-3-[[5-bromo-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-n-methylbicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(=O)NC)C(C(=CN=1)Br)=NC=1NC=1C=NN(C)C=1 CWGMUGAHFWGINC-XXSPCDMZSA-N 0.000 claims 1
GEATXDJAPAHPTP-FIDNZITISA-N (1s,2s,3r,4r)-3-[[5-bromo-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Br)=NC=1NC=1C=NN(C)C=1 GEATXDJAPAHPTP-FIDNZITISA-N 0.000 claims 1
KYCMHUJTGBLLHL-FCLUMBPUSA-N (1s,2s,3r,4r)-3-[[5-bromo-2-[(1-piperidin-4-ylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Br)=NC=1NC(=C1)C=NN1C1CCNCC1 KYCMHUJTGBLLHL-FCLUMBPUSA-N 0.000 claims 1
IAZUGRWWIZOAEW-FDRIWYBQSA-N (1s,2s,3r,4r)-3-[[5-bromo-2-[[1-(2-methylsulfonylethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Br)=NC=1NC=1C=NN(CCS(C)(=O)=O)C=1 IAZUGRWWIZOAEW-FDRIWYBQSA-N 0.000 claims 1
VXPDAIADPMQBBR-GIYDNNGJSA-N (1s,2s,3r,4r)-3-[[5-bromo-2-[[1-(2-phenylethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Br)=NC=1NC(=C1)C=NN1CCC1=CC=CC=C1 VXPDAIADPMQBBR-GIYDNNGJSA-N 0.000 claims 1
YVFYECZGRSPZCZ-XBMQVOARSA-N (1s,2s,3r,4r)-3-[[5-bromo-2-[[1-[(2s)-2,3-dihydroxypropyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Br)=NC=1NC=1C=NN(C[C@H](O)CO)C=1 YVFYECZGRSPZCZ-XBMQVOARSA-N 0.000 claims 1
VOXCNTSFHVBEAX-VVVONTASSA-N (1s,2s,3r,4r)-3-[[5-bromo-2-[[1-[(3-methoxyphenyl)methyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Br)=NC=1NC(=C1)C=NN1CC1=CC=CC(OC)=C1 VOXCNTSFHVBEAX-VVVONTASSA-N 0.000 claims 1
MMHQHAFOPSWAEB-AYULTIFVSA-N (1s,2s,3r,4r)-3-[[5-bromo-2-[[1-[(3r)-oxolan-3-yl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Br)=NC=1NC(=C1)C=NN1[C@@H]1CCOC1 MMHQHAFOPSWAEB-AYULTIFVSA-N 0.000 claims 1
MMHQHAFOPSWAEB-WABRKEKUSA-N (1s,2s,3r,4r)-3-[[5-bromo-2-[[1-[(3s)-oxolan-3-yl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Br)=NC=1NC(=C1)C=NN1[C@H]1CCOC1 MMHQHAFOPSWAEB-WABRKEKUSA-N 0.000 claims 1
QBMLTVKJQMBADK-OSRSDYAFSA-N (1s,2s,3r,4r)-3-[[5-bromo-2-[[1-[2-(2-methoxyethoxy)ethyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Br)=NC=1NC=1C=NN(CCOCCOC)C=1 QBMLTVKJQMBADK-OSRSDYAFSA-N 0.000 claims 1
UALMTSDHIKMIPE-QMKUDKLTSA-N (1s,2s,3r,4r)-3-[[5-bromo-2-[[1-[2-(3-methoxyphenyl)ethyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Br)=NC=1NC(=C1)C=NN1CCC1=CC=CC(OC)=C1 UALMTSDHIKMIPE-QMKUDKLTSA-N 0.000 claims 1
JLHGVZCZENMOJO-LVFSCSRESA-N (1s,2s,3r,4r)-3-[[5-bromo-2-[[1-[2-(4-methylpiperazin-1-yl)ethyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Br)=NC=1NC(=C1)C=NN1CCN1CCN(C)CC1 JLHGVZCZENMOJO-LVFSCSRESA-N 0.000 claims 1
SEGFKEBXPYKXEF-KTJYFRGRSA-N (1s,2s,3r,4r)-3-[[5-bromo-2-[[1-[2-(methylamino)-2-oxoethyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Br)=NC=1NC=1C=NN(CC(=O)NC)C=1 SEGFKEBXPYKXEF-KTJYFRGRSA-N 0.000 claims 1
NCIAUWBSJNZFII-REJLFOLJSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethylpyrazol-4-yl)amino]-6-methylpyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=C(C)N=1)Cl)=NC=1NC=1C=NN(CC)C=1 NCIAUWBSJNZFII-REJLFOLJSA-N 0.000 claims 1
GWAODKLMHUOUEN-FDRIWYBQSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-n-methylbicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(=O)NC)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CC)C=1 GWAODKLMHUOUEN-FDRIWYBQSA-N 0.000 claims 1
UWJZCHZNTUYAIM-XXSPCDMZSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-n-methylbicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(=O)NC)C(C(=CN=1)Cl)=NC=1NC=1C=NN(C)C=1 UWJZCHZNTUYAIM-XXSPCDMZSA-N 0.000 claims 1
HJBPCZMHQMQIJH-FDRIWYBQSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[1-(2-methylsulfonylethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CCS(C)(=O)=O)C=1 HJBPCZMHQMQIJH-FDRIWYBQSA-N 0.000 claims 1
KABAZFRNMIEGAI-GIYDNNGJSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[1-(2-phenylethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1CCC1=CC=CC=C1 KABAZFRNMIEGAI-GIYDNNGJSA-N 0.000 claims 1
BUDFXBPQZONFSQ-LVFSCSRESA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[1-[(1-methylpiperidin-4-yl)methyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1CC1CCN(C)CC1 BUDFXBPQZONFSQ-LVFSCSRESA-N 0.000 claims 1
DFGVHLXQKKXNQR-UCTJBKIYSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[1-[(2r)-2,3-dihydroxypropyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(C[C@@H](O)CO)C=1 DFGVHLXQKKXNQR-UCTJBKIYSA-N 0.000 claims 1
VCXHDHATPXNSIJ-HFLGISGGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[1-[(2r)-2-hydroxypropyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(C[C@@H](C)O)C=1 VCXHDHATPXNSIJ-HFLGISGGSA-N 0.000 claims 1
DFGVHLXQKKXNQR-XBMQVOARSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[1-[(2s)-2,3-dihydroxypropyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(C[C@H](O)CO)C=1 DFGVHLXQKKXNQR-XBMQVOARSA-N 0.000 claims 1
OPFYNRGXSOEQKZ-VVVONTASSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[1-[(3-methoxyphenyl)methyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1CC1=CC=CC(OC)=C1 OPFYNRGXSOEQKZ-VVVONTASSA-N 0.000 claims 1
ROHRJTWJYIWOPI-AYULTIFVSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[1-[(3r)-oxolan-3-yl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1[C@@H]1CCOC1 ROHRJTWJYIWOPI-AYULTIFVSA-N 0.000 claims 1
NUIGAOCWJPYVEO-BEANVFONSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[1-[(3r)-piperidin-3-yl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1[C@@H]1CCCNC1 NUIGAOCWJPYVEO-BEANVFONSA-N 0.000 claims 1
FZSVXZJKMQSLBF-AYULTIFVSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[1-[(3r)-pyrrolidin-3-yl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1[C@@H]1CCNC1 FZSVXZJKMQSLBF-AYULTIFVSA-N 0.000 claims 1
ROHRJTWJYIWOPI-WABRKEKUSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[1-[(3s)-oxolan-3-yl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1[C@H]1CCOC1 ROHRJTWJYIWOPI-WABRKEKUSA-N 0.000 claims 1
NUIGAOCWJPYVEO-RJFUSWPYSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[1-[(3s)-piperidin-3-yl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1[C@H]1CCCNC1 NUIGAOCWJPYVEO-RJFUSWPYSA-N 0.000 claims 1
FZSVXZJKMQSLBF-WABRKEKUSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[1-[(3s)-pyrrolidin-3-yl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1[C@H]1CCNC1 FZSVXZJKMQSLBF-WABRKEKUSA-N 0.000 claims 1
XAMAKWKZVDGUJT-OSRSDYAFSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[1-[2-(2-methoxyethoxy)ethyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CCOCCOC)C=1 XAMAKWKZVDGUJT-OSRSDYAFSA-N 0.000 claims 1
UQCSQFFVIBCXMX-VVVONTASSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[1-[2-(3-chlorophenyl)ethyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1CCC1=CC=CC(Cl)=C1 UQCSQFFVIBCXMX-VVVONTASSA-N 0.000 claims 1
GKBDOJWTVHZLLZ-QMKUDKLTSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[1-[2-(3-methoxyphenyl)ethyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1CCC1=CC=CC(OC)=C1 GKBDOJWTVHZLLZ-QMKUDKLTSA-N 0.000 claims 1
YDEMQAAYOCNYEP-LZJQFABFSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[1-[2-(dimethylamino)-2-oxoethyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CC(=O)N(C)C)C=1 YDEMQAAYOCNYEP-LZJQFABFSA-N 0.000 claims 1
STBMZODYQLKFRA-GUYJKWIASA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[1-[2-(dimethylamino)ethyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CCN(C)C)C=1 STBMZODYQLKFRA-GUYJKWIASA-N 0.000 claims 1
NUPQKBHSBNJYIP-KTJYFRGRSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[1-[2-(methylamino)-2-oxoethyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CC(=O)NC)C=1 NUPQKBHSBNJYIP-KTJYFRGRSA-N 0.000 claims 1
NZSZVQMHSLFGDA-BBAXIROVSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[1-[[(2r)-pyrrolidin-2-yl]methyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1C[C@H]1CCCN1 NZSZVQMHSLFGDA-BBAXIROVSA-N 0.000 claims 1
MNGDJFQVLRLXMO-XXSPCDMZSA-N (1s,2s,3r,4r)-3-[[5-fluoro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-n-methylbicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(=O)NC)C(C(=CN=1)F)=NC=1NC=1C=NN(C)C=1 MNGDJFQVLRLXMO-XXSPCDMZSA-N 0.000 claims 1
YVSLWXDYSJAARW-HFLGISGGSA-N (1s,2s,3r,4r)-3-[[5-fluoro-2-[[1-[(2r)-2-hydroxypropyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)F)=NC=1NC=1C=NN(C[C@@H](C)O)C=1 YVSLWXDYSJAARW-HFLGISGGSA-N 0.000 claims 1
CIXLLNNDLZVHIJ-LZJQFABFSA-N (1s,2s,3r,4r)-n-cyclopropyl-3-[[2-[(1-methylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(=O)NC1CC1)C(C(=CN=1)C(F)(F)F)=NC=1NC=1C=NN(C)C=1 CIXLLNNDLZVHIJ-LZJQFABFSA-N 0.000 claims 1
XXHKWYBEHKUWRK-XXSPCDMZSA-N (1s,2s,3r,4r)-n-methyl-3-[[2-[(1-methylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(=O)NC)C(C(=CN=1)C(F)(F)F)=NC=1NC=1C=NN(C)C=1 XXHKWYBEHKUWRK-XXSPCDMZSA-N 0.000 claims 1
QGZHGDKWJHKAEZ-CMPLNLGQSA-N (1s,6r)-6-[[2-[(1-methylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]cyclohex-3-ene-1-carboxamide Chemical compound C1=NN(C)C=C1NC1=NC=C(C(F)(F)F)C(N[C@H]2[C@H](CC=CC2)C(N)=O)=N1 QGZHGDKWJHKAEZ-CMPLNLGQSA-N 0.000 claims 1
KODLCCUPBUCARD-CMPLNLGQSA-N (1s,6r)-6-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]cyclohex-3-ene-1-carboxamide Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(N[C@H]2[C@H](CC=CC2)C(N)=O)=N1 KODLCCUPBUCARD-CMPLNLGQSA-N 0.000 claims 1
UIDWSNOOPHGNAG-UHFFFAOYSA-N 2-[2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]phenyl]propan-2-ol Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC=2C(=CC=CC=2)C(C)(C)O)=N1 UIDWSNOOPHGNAG-UHFFFAOYSA-N 0.000 claims 1
OJEYDZBIAYMFFD-UHFFFAOYSA-N cyclopentanecarboxamide Chemical compound NC(=O)C1C[CH]CC1 OJEYDZBIAYMFFD-UHFFFAOYSA-N 0.000 claims 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
INKBSSQMCNXVSE-SONRMIBWSA-N propan-2-yl 2-[4-[[4-[[(1r,2r,3s,4s)-2-carbamoyl-3-bicyclo[2.2.1]hept-5-enyl]amino]-5-fluoropyrimidin-2-yl]amino]pyrazol-1-yl]acetate Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=CN=1)F)=NC=1NC=1C=NN(CC(=O)OC(C)C)C=1 INKBSSQMCNXVSE-SONRMIBWSA-N 0.000 claims 1
NLYMESWNDCHLRG-FCLUMBPUSA-N propan-2-yl 2-[4-[[4-[[(1s,2s,3r,4r)-2-carbamoyl-3-bicyclo[2.2.1]hept-5-enyl]amino]-5-chloropyrimidin-2-yl]amino]pyrazol-1-yl]acetate Chemical compound C1=NN(CC(=O)OC(C)C)C=C1NC1=NC=C(Cl)C(N[C@H]2[C@H]([C@H]3C[C@@H]2C=C3)C(N)=O)=N1 NLYMESWNDCHLRG-FCLUMBPUSA-N 0.000 claims 1
HYZWBHXXZCXBBJ-FCLUMBPUSA-N propan-2-yl 2-[4-[[5-bromo-4-[[(1R,2R,3S,4S)-3-carbamoyl-2-bicyclo[2.2.1]hept-5-enyl]amino]pyrimidin-2-yl]amino]pyrazol-1-yl]acetate Chemical compound C(C)(C)OC(CN1N=CC(=C1)NC1=NC=C(C(=N1)N[C@@H]1[C@H]2C=C[C@@H]([C@@H]1C(=O)N)C2)Br)=O HYZWBHXXZCXBBJ-FCLUMBPUSA-N 0.000 claims 1
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