SG177454A1 - Pyrazolopyrimidine jak inhibitor compounds and methods - Google Patents

Info

Publication number

SG177454A1

SG177454A1 SG2011097623A SG2011097623A SG177454A1 SG 177454 A1 SG177454 A1 SG 177454A1 SG 2011097623 A SG2011097623 A SG 2011097623A SG 2011097623 A SG2011097623 A SG 2011097623A SG 177454 A1 SG177454 A1 SG 177454A1

Authority

SG

Singapore

Prior art keywords

alkyl

optionally substituted

halogen

oxo

pyrazolo

Prior art date

2009-07-02

Links

• Espacenet
• Global Dossier
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims abstract description 273
• 238000000034 method Methods 0.000 title claims abstract description 70
• 229940122245 Janus kinase inhibitor Drugs 0.000 title description 9
• OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical compound C12=NC(NCCCC)=NC=C2C(C=2C=CC(F)=CC=2)=NN1C[C@H]1CC[C@H](N)CC1 OGEBRHQLRGFBNV-RZDIXWSQSA-N 0.000 title description 5
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• 108010024121 Janus Kinases Proteins 0.000 claims abstract description 32
• 230000000694 effects Effects 0.000 claims abstract description 30
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 24
• 150000003839 salts Chemical class 0.000 claims abstract description 23
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 17
• 230000005764 inhibitory process Effects 0.000 claims abstract description 14
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• 125000000623 heterocyclic group Chemical group 0.000 claims description 89
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• 229910052739 hydrogen Inorganic materials 0.000 claims description 53
• 239000001257 hydrogen Substances 0.000 claims description 46
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 43
• 229910052792 caesium Inorganic materials 0.000 claims description 41
• 125000004043 oxo group Chemical group O=* 0.000 claims description 38
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
• 238000011282 treatment Methods 0.000 claims description 32
• 125000004429 atom Chemical group 0.000 claims description 31
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• 125000003226 pyrazolyl group Chemical group 0.000 claims description 23
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 21
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• MCBSZIDQUDBWTG-UHFFFAOYSA-N n-(5-methyl-2-phenylpyrazol-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound N1=C(C)C=C(NC(=O)C2=C3N=CC=CN3N=C2)N1C1=CC=CC=C1 MCBSZIDQUDBWTG-UHFFFAOYSA-N 0.000 claims description 3
• VLHYMDDYRUYYLE-UHFFFAOYSA-N n-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=CSC(NC(=O)C2=C3N=CC=CN3N=C2)=N1 VLHYMDDYRUYYLE-UHFFFAOYSA-N 0.000 claims description 3
• ZZIWHWXPXNFRSR-UHFFFAOYSA-N n-[5-methyl-4-(4-propylphenyl)-1,3-thiazol-2-yl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC(CCC)=CC=C1C1=C(C)SC(NC(=O)C2=C3N=CC=CN3N=C2)=N1 ZZIWHWXPXNFRSR-UHFFFAOYSA-N 0.000 claims description 3
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• 238000003818 flash chromatography Methods 0.000 description 26
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 24
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• 239000007787 solid Substances 0.000 description 22
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• 230000015572 biosynthetic process Effects 0.000 description 21
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• 229910000024 caesium carbonate Inorganic materials 0.000 description 21
• PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 21
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