CA3055602A1 - Bruton's tyrosine kinase inhibitors - Google Patents

Info

Publication number

CA3055602A1

CA3055602A1 CA3055602A CA3055602A CA3055602A1 CA 3055602 A1 CA3055602 A1 CA 3055602A1 CA 3055602 A CA3055602 A CA 3055602A CA 3055602 A CA3055602 A CA 3055602A CA 3055602 A1 CA3055602 A1 CA 3055602A1

Authority

CA

Canada

Prior art keywords

pyrazin

phenyl

imidazo

pyrrolidin

methoxyphenoxy

Prior art date

2017-03-22

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Pending

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 102000001714 Agammaglobulinaemia Tyrosine Kinase Human genes 0.000 title abstract description 6
• 108010029445 Agammaglobulinaemia Tyrosine Kinase Proteins 0.000 title abstract description 6
• 229940121358 tyrosine kinase inhibitor Drugs 0.000 title description 5
• 239000005483 tyrosine kinase inhibitor Substances 0.000 title description 4
• -1 imidazo[1,5-a]pyrazin-3-yl Chemical group 0.000 claims description 166
• 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 164
• 150000001875 compounds Chemical class 0.000 claims description 118
• 239000000203 mixture Substances 0.000 claims description 115
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 100
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 83
• HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 46
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 43
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
• 238000000034 method Methods 0.000 claims description 27
• 235000019000 fluorine Nutrition 0.000 claims description 18
• 229910052739 hydrogen Inorganic materials 0.000 claims description 18
• 239000001257 hydrogen Substances 0.000 claims description 18
• SSYZCZMNTIFVDJ-IBGZPJMESA-N 1-[(2S)-2-[1-(6-phenoxypyridin-3-yl)imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound O(C1=CC=CC=C1)C1=CC=C(C=N1)C=1N=C(N2C=1C=NC=C2)[C@H]1N(CCC1)C(C=C)=O SSYZCZMNTIFVDJ-IBGZPJMESA-N 0.000 claims description 17
• 229910052757 nitrogen Inorganic materials 0.000 claims description 17
• 125000001153 fluoro group Chemical group F* 0.000 claims description 15
• 150000002431 hydrogen Chemical group 0.000 claims description 15
• HXYZVCWSHYGZBD-FQEVSTJZSA-N 1-[(2S)-2-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCCC2)C(C=C)=O)C=CC=C1OC HXYZVCWSHYGZBD-FQEVSTJZSA-N 0.000 claims description 12
• 150000002367 halogens Chemical group 0.000 claims description 12
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
• 229910052760 oxygen Inorganic materials 0.000 claims description 12
• 125000003118 aryl group Chemical group 0.000 claims description 10
• 229910052736 halogen Inorganic materials 0.000 claims description 10
• 125000001072 heteroaryl group Chemical group 0.000 claims description 10
• 125000000623 heterocyclic group Chemical group 0.000 claims description 10
• 229920006395 saturated elastomer Polymers 0.000 claims description 10
• 229910052717 sulfur Chemical group 0.000 claims description 10
• 206010028980 Neoplasm Diseases 0.000 claims description 9
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
• 239000003814 drug Substances 0.000 claims description 9
• 125000005842 heteroatom Chemical group 0.000 claims description 9
• 239000001301 oxygen Chemical group 0.000 claims description 9
• 208000023275 Autoimmune disease Diseases 0.000 claims description 8
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
• 239000011593 sulfur Chemical group 0.000 claims description 8
• UULCMWFOJYIYAC-LJQANCHMSA-N 1-[(3R)-3-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2CN(CCC2)C(C=C)=O)C=CC=C1OC UULCMWFOJYIYAC-LJQANCHMSA-N 0.000 claims description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
• 201000010099 disease Diseases 0.000 claims description 6
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
• 229910052731 fluorine Inorganic materials 0.000 claims description 6
• 229940002612 prodrug Drugs 0.000 claims description 6
• 239000000651 prodrug Substances 0.000 claims description 6
• URHMZJXXCSDYMN-MRTLOADZSA-N (6R)-6-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]-2,5,6,7,8,8a-hexahydro-1H-indolizin-3-one Chemical compound COC1=CC=CC(OC2=CC=C(C=C2)C2=C3C=NC=CN3C(=N2)[C@@H]2CCC3CCC(=O)N3C2)=C1F URHMZJXXCSDYMN-MRTLOADZSA-N 0.000 claims description 5
• CKZUKEVWQAZFBC-NRFANRHFSA-N 1-[(2S)-2-[1-[4-[(2,3-difluorophenyl)methoxy]phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound FC1=C(COC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCC2)C(C=C)=O)C=CC=C1F CKZUKEVWQAZFBC-NRFANRHFSA-N 0.000 claims description 5
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
• 229940079593 drug Drugs 0.000 claims description 5
• 208000027866 inflammatory disease Diseases 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• 125000001424 substituent group Chemical group 0.000 claims description 5
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
• LEEWZFMVOTUQDG-NRFANRHFSA-N 1-[(2S)-2-[1-[4-[(2-fluorophenoxy)methyl]phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound FC1=C(OCC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCC2)C(C=C)=O)C=CC=C1 LEEWZFMVOTUQDG-NRFANRHFSA-N 0.000 claims description 4
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
• 125000005037 alkyl phenyl group Chemical group 0.000 claims description 4
• 125000002619 bicyclic group Chemical group 0.000 claims description 4
• 239000011737 fluorine Chemical group 0.000 claims description 4
• 230000001404 mediated effect Effects 0.000 claims description 4
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
• 229940124597 therapeutic agent Drugs 0.000 claims description 4
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
• 239000012453 solvate Substances 0.000 claims description 3
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 3
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 2
• FDVCLKSZGDCNHZ-NRFANRHFSA-N 1-[(2S)-2-[1-(2-chloro-4-phenoxyphenyl)imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound ClC1=C(C=CC(=C1)OC1=CC=CC=C1)C=1N=C(N2C=1C=NC=C2)[C@H]1N(CCC1)C(C=C)=O FDVCLKSZGDCNHZ-NRFANRHFSA-N 0.000 claims description 2
• ZOASDAPXBDSGDS-FQEVSTJZSA-N 1-[(2S)-2-[1-(3-chloro-4-phenoxyphenyl)imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C(C=CC=1OC1=CC=CC=C1)C=1N=C(N2C=1C=NC=C2)[C@H]1N(CCC1)C(C=C)=O ZOASDAPXBDSGDS-FQEVSTJZSA-N 0.000 claims description 2
• CHFVKQLCNBSKGE-NRFANRHFSA-N 1-[(2S)-2-[1-(5-phenoxypyridin-2-yl)imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound O(C1=CC=CC=C1)C=1C=CC(=NC=1)C=1N=C(N2C=1C=NC=C2)[C@H]1N(CCC1)C(C#CC)=O CHFVKQLCNBSKGE-NRFANRHFSA-N 0.000 claims description 2
• OGVBISBIDDHLMR-FQEVSTJZSA-N 1-[(2S)-2-[1-(6-phenoxypyridin-3-yl)imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound O(C1=CC=CC=C1)C1=CC=C(C=N1)C=1N=C(N2C=1C=NC=C2)[C@H]1N(CCC1)C(C#CC)=O OGVBISBIDDHLMR-FQEVSTJZSA-N 0.000 claims description 2
• KEVGNTLGNXQCTI-IBGZPJMESA-N 1-[(2S)-2-[1-[4-(2,3-difluorophenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCC2)C(C=C)=O)C=CC=C1F KEVGNTLGNXQCTI-IBGZPJMESA-N 0.000 claims description 2
• ADMCZFZVXVCJOO-QFIPXVFZSA-N 1-[(2S)-2-[1-[4-(2,3-dimethylphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound CC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCC2)C(C=C)=O)C=CC=C1C ADMCZFZVXVCJOO-QFIPXVFZSA-N 0.000 claims description 2
• PHPMJHNKOPXOJB-NRFANRHFSA-N 1-[(2S)-2-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCCC2)C(C#CC)=O)C=CC=C1OC PHPMJHNKOPXOJB-NRFANRHFSA-N 0.000 claims description 2
• NUUIGSUDORJKRR-FQEVSTJZSA-N 1-[(2S)-2-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound COc1cccc(Oc2ccc(cc2)-c2nc([C@@H]3CCCN3C(=O)C#CC)n3ccncc23)c1F NUUIGSUDORJKRR-FQEVSTJZSA-N 0.000 claims description 2
• CFYBPLINLQYRJH-IBGZPJMESA-N 1-[(2S)-2-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCC2)C(C=C)=O)C=CC=C1OC CFYBPLINLQYRJH-IBGZPJMESA-N 0.000 claims description 2
• UYMGAYXWGMNGKT-NRFANRHFSA-N 1-[(2S)-2-[1-[4-(2-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound COC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCC2)C(C#CC)=O)C=CC=C1 UYMGAYXWGMNGKT-NRFANRHFSA-N 0.000 claims description 2
• OGQIUBDFALKWBG-FQEVSTJZSA-N 1-[(2S)-2-[1-[4-(2-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound COC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCC2)C(C=C)=O)C=CC=C1 OGQIUBDFALKWBG-FQEVSTJZSA-N 0.000 claims description 2
• ZXHDMYQJZRCOMG-NRFANRHFSA-N 1-[(2S)-2-[1-[4-(3-chloro-2-fluorophenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound ClC=1C(=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCCC2)C(C#CC)=O)C=CC=1)F ZXHDMYQJZRCOMG-NRFANRHFSA-N 0.000 claims description 2
• XCHUWLYZXJKNSH-IBGZPJMESA-N 1-[(2S)-2-[1-[4-(3-chloro-2-fluorophenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound ClC=1C(=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCC2)C(C=C)=O)C=CC=1)F XCHUWLYZXJKNSH-IBGZPJMESA-N 0.000 claims description 2
• AHMRDGGMOAZUNG-NRFANRHFSA-N 1-[(2S)-2-[1-[4-(3-chlorophenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound ClC=1C=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCC2)C(C=C)=O)C=CC=1 AHMRDGGMOAZUNG-NRFANRHFSA-N 0.000 claims description 2
• MKEYMXUUPICWPW-QFIPXVFZSA-N 1-[(2S)-2-[1-[4-(3-fluorophenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound FC=1C=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCCC2)C(C=C)=O)C=CC=1 MKEYMXUUPICWPW-QFIPXVFZSA-N 0.000 claims description 2
• IRGZCRZHQHEKJW-QFIPXVFZSA-N 1-[(2S)-2-[1-[4-(3-fluorophenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound FC=1C=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCC2)C(C#CC)=O)C=CC=1 IRGZCRZHQHEKJW-QFIPXVFZSA-N 0.000 claims description 2
• ZSNNZNAPAFPYOR-NRFANRHFSA-N 1-[(2S)-2-[1-[4-(3-fluorophenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound FC=1C=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCC2)C(C=C)=O)C=CC=1 ZSNNZNAPAFPYOR-NRFANRHFSA-N 0.000 claims description 2
• RJCQWKWYJJUATE-NRFANRHFSA-N 1-[(2S)-2-[1-[4-(3-methoxy-2-methylphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound COC=1C(=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCC2)C(C=C)=O)C=CC=1)C RJCQWKWYJJUATE-NRFANRHFSA-N 0.000 claims description 2
• BKKJIUUEKPPIIK-DEOSSOPVSA-N 1-[(2S)-2-[1-[4-(3-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound COC=1C=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCCC2)C(C#CC)=O)C=CC=1 BKKJIUUEKPPIIK-DEOSSOPVSA-N 0.000 claims description 2
• ZWCOAZIWRLDHGP-QHCPKHFHSA-N 1-[(2S)-2-[1-[4-(3-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound COC=1C=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCCC2)C(C=C)=O)C=CC=1 ZWCOAZIWRLDHGP-QHCPKHFHSA-N 0.000 claims description 2
• PGVGTJDOYNQGLQ-QFIPXVFZSA-N 1-[(2S)-2-[1-[4-(3-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound COC=1C=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCC2)C(C=C)=O)C=CC=1 PGVGTJDOYNQGLQ-QFIPXVFZSA-N 0.000 claims description 2
• HTSOZSFANPRUOV-DEOSSOPVSA-N 1-[(2S)-2-[1-[4-(3-methylphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound C1(=CC(=CC=C1)OC1=CC=C(C=C1)C=1N=C(N2C=1C=NC=C2)[C@H]1N(CCCC1)C(C#CC)=O)C HTSOZSFANPRUOV-DEOSSOPVSA-N 0.000 claims description 2
• OUCWSWNWPYKSLV-QHCPKHFHSA-N 1-[(2S)-2-[1-[4-(3-methylphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound C1(=CC(=CC=C1)OC1=CC=C(C=C1)C=1N=C(N2C=1C=NC=C2)[C@H]1N(CCCC1)C(C=C)=O)C OUCWSWNWPYKSLV-QHCPKHFHSA-N 0.000 claims description 2
• IRAUOVRNSDUIES-QHCPKHFHSA-N 1-[(2S)-2-[1-[4-(3-methylphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound C1(=CC(=CC=C1)OC1=CC=C(C=C1)C=1N=C(N2C=1C=NC=C2)[C@H]1N(CCC1)C(C#CC)=O)C IRAUOVRNSDUIES-QHCPKHFHSA-N 0.000 claims description 2
• NMPMNTXOSOSTEY-QFIPXVFZSA-N 1-[(2S)-2-[1-[4-(3-methylphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound C1(=CC(=CC=C1)OC1=CC=C(C=C1)C=1N=C(N2C=1C=NC=C2)[C@H]1N(CCC1)C(C=C)=O)C NMPMNTXOSOSTEY-QFIPXVFZSA-N 0.000 claims description 2
• PRKBXPYKMKFYCL-VWLOTQADSA-N 1-[(2S)-2-[1-[4-(3-propan-2-yloxyphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound C(C)(C)OC=1C=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCC2)C(C#CC)=O)C=CC=1 PRKBXPYKMKFYCL-VWLOTQADSA-N 0.000 claims description 2
• FFHQEZBIIRZIGL-QHCPKHFHSA-N 1-[(2S)-2-[1-[4-(4-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound COC1=CC=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCC2)C(C#CC)=O)C=C1 FFHQEZBIIRZIGL-QHCPKHFHSA-N 0.000 claims description 2
• OUXULLVBOXHILT-QHCPKHFHSA-N 1-[(2S)-2-[1-[4-(phenoxymethyl)phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound O(C1=CC=CC=C1)CC1=CC=C(C=C1)C=1N=C(N2C=1C=NC=C2)[C@H]1N(CCC1)C(C#CC)=O OUXULLVBOXHILT-QHCPKHFHSA-N 0.000 claims description 2
• NBCAUAHWWWXHNR-QFIPXVFZSA-N 1-[(2S)-2-[1-[4-(phenoxymethyl)phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound O(C1=CC=CC=C1)CC1=CC=C(C=C1)C=1N=C(N2C=1C=NC=C2)[C@H]1N(CCC1)C(C=C)=O NBCAUAHWWWXHNR-QFIPXVFZSA-N 0.000 claims description 2
• SSEKGNXPUWYQNF-QFIPXVFZSA-N 1-[(2S)-2-[1-[4-[(2,3-difluorophenoxy)methyl]phenyl]imidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound FC1=C(OCC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCCC2)C(C#CC)=O)C=CC=C1F SSEKGNXPUWYQNF-QFIPXVFZSA-N 0.000 claims description 2
• SELBOKWPOUGADD-NRFANRHFSA-N 1-[(2S)-2-[1-[4-[(2,3-difluorophenoxy)methyl]phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound FC1=C(OCC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCC2)C(C#CC)=O)C=CC=C1F SELBOKWPOUGADD-NRFANRHFSA-N 0.000 claims description 2
• MJQPPHQYIZZCLH-FQEVSTJZSA-N 1-[(2S)-2-[1-[4-[(2,3-difluorophenoxy)methyl]phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound FC1=C(OCC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCC2)C(C=C)=O)C=CC=C1F MJQPPHQYIZZCLH-FQEVSTJZSA-N 0.000 claims description 2
• HJMXCWRLAFZJKL-QFIPXVFZSA-N 1-[(2S)-2-[1-[4-[(2,3-difluorophenyl)methoxy]phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound FC1=C(COC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCC2)C(C#CC)=O)C=CC=C1F HJMXCWRLAFZJKL-QFIPXVFZSA-N 0.000 claims description 2
• ANHBARXSPJWSFP-QHCPKHFHSA-N 1-[(2S)-2-[1-[4-[(2,6-difluorophenyl)methoxy]phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound FC1=C(COC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCC2)C(C#CC)=O)C(=CC=C1)F ANHBARXSPJWSFP-QHCPKHFHSA-N 0.000 claims description 2
• CSMJFQYPKDVUEM-DEOSSOPVSA-N 1-[(2S)-2-[1-[4-[(3,4-difluorophenoxy)methyl]phenyl]imidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound FC=1C=C(OCC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCCC2)C(C#CC)=O)C=CC=1F CSMJFQYPKDVUEM-DEOSSOPVSA-N 0.000 claims description 2
• YELXBDWJJYMVBX-QHCPKHFHSA-N 1-[(2S)-2-[1-[4-[(3,4-difluorophenoxy)methyl]phenyl]imidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound Fc1ccc(OCc2ccc(cc2)-c2nc([C@@H]3CCCCN3C(=O)C=C)n3ccncc23)cc1F YELXBDWJJYMVBX-QHCPKHFHSA-N 0.000 claims description 2
• KGSQFIHUZLQRRG-QHCPKHFHSA-N 1-[(2S)-2-[1-[4-[(3,4-difluorophenoxy)methyl]phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound FC=1C=C(OCC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCC2)C(C#CC)=O)C=CC=1F KGSQFIHUZLQRRG-QHCPKHFHSA-N 0.000 claims description 2
• WDDPHUZRZJXARE-QFIPXVFZSA-N 1-[(2S)-2-[1-[4-[(3,4-difluorophenoxy)methyl]phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound FC=1C=C(OCC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCC2)C(C=C)=O)C=CC=1F WDDPHUZRZJXARE-QFIPXVFZSA-N 0.000 claims description 2
• ZXARJOZIWRAZEU-QHCPKHFHSA-N 1-[(2S)-2-[1-[4-[(3,4-difluorophenyl)methoxy]phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound FC=1C=C(COC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCC2)C(C#CC)=O)C=CC=1F ZXARJOZIWRAZEU-QHCPKHFHSA-N 0.000 claims description 2
• PVLSBBBLEUZIJP-QFIPXVFZSA-N 1-[(2S)-2-[1-[4-[(3,4-difluorophenyl)methoxy]phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound FC=1C=C(COC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCC2)C(C=C)=O)C=CC=1F PVLSBBBLEUZIJP-QFIPXVFZSA-N 0.000 claims description 2
• IHZAKQWTSSBKKB-QHCPKHFHSA-N 1-[(2S)-2-[1-[4-[(3-fluorophenoxy)methyl]phenyl]imidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound FC1=CC=CC(OCC2=CC=C(C=C2)C2=C3C=NC=CN3C(=N2)[C@@H]2CCCCN2C(=O)C=C)=C1 IHZAKQWTSSBKKB-QHCPKHFHSA-N 0.000 claims description 2
• FQZGTFWZDOZCCV-QHCPKHFHSA-N 1-[(2S)-2-[1-[4-[(3-fluorophenoxy)methyl]phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound FC=1C=C(OCC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCC2)C(C#CC)=O)C=CC=1 FQZGTFWZDOZCCV-QHCPKHFHSA-N 0.000 claims description 2
• LIMBBGFIWCUFDT-QFIPXVFZSA-N 1-[(2S)-2-[1-[4-[(3-fluorophenoxy)methyl]phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound FC1=CC=CC(OCC2=CC=C(C=C2)C2=C3C=NC=CN3C(=N2)[C@@H]2CCCN2C(=O)C=C)=C1 LIMBBGFIWCUFDT-QFIPXVFZSA-N 0.000 claims description 2
• UANOKEHRBPWMEV-DEOSSOPVSA-N 1-[(2S)-2-[1-[4-[(3-fluorophenyl)methoxy]phenyl]imidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound FC=1C=C(COC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCCC2)C(C#CC)=O)C=CC=1 UANOKEHRBPWMEV-DEOSSOPVSA-N 0.000 claims description 2
• WQHILVZFIKLFNR-QHCPKHFHSA-N 1-[(2S)-2-[1-[4-[(3-fluorophenyl)methoxy]phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound FC=1C=C(COC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCC2)C(C#CC)=O)C=CC=1 WQHILVZFIKLFNR-QHCPKHFHSA-N 0.000 claims description 2
• DLVJIQAJWYDDEM-QFIPXVFZSA-N 1-[(2S)-2-[1-[4-[(3-fluorophenyl)methoxy]phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound FC=1C=C(COC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCC2)C(C=C)=O)C=CC=1 DLVJIQAJWYDDEM-QFIPXVFZSA-N 0.000 claims description 2
• VEJJFMFJXNHISE-LJQANCHMSA-N 1-[(3R)-3-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2CN(CC2)C(C#CC)=O)C=CC=C1OC VEJJFMFJXNHISE-LJQANCHMSA-N 0.000 claims description 2
• HQCQWRAAODQDQJ-GOSISDBHSA-N 1-[(3R)-3-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2CN(CC2)C(C=C)=O)C=CC=C1OC HQCQWRAAODQDQJ-GOSISDBHSA-N 0.000 claims description 2
• DWIBBYMSBCWNLT-HXUWFJFHSA-N 1-[(3R)-3-[1-[4-(3-fluorophenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound FC=1C=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2CN(CCC2)C(C#CC)=O)C=CC=1 DWIBBYMSBCWNLT-HXUWFJFHSA-N 0.000 claims description 2
• QNEBMMFQEVAHJI-OAQYLSRUSA-N 1-[(3R)-3-[1-[4-(3-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound COC=1C=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2CN(CCC2)C(C#CC)=O)C=CC=1 QNEBMMFQEVAHJI-OAQYLSRUSA-N 0.000 claims description 2
• UFAUIQBDQOAXRI-JOCHJYFZSA-N 1-[(3R)-3-[5-[2-(dimethylamino)ethoxy]-1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound CN(CCOC1=CN=CC=2N1C(=NC=2C1=CC=C(C=C1)OC1=C(C(=CC=C1)OC)F)[C@H]1CN(CC1)C(C#CC)=O)C UFAUIQBDQOAXRI-JOCHJYFZSA-N 0.000 claims description 2
• WDOYWXMKELNSFG-OAQYLSRUSA-N 1-[(3R)-3-[5-[2-(dimethylamino)ethoxy]-1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound CN(CCOC1=CN=CC=2N1C(=NC=2C1=CC=C(C=C1)OC1=C(C(=CC=C1)OC)F)[C@H]1CN(CC1)C(C=C)=O)C WDOYWXMKELNSFG-OAQYLSRUSA-N 0.000 claims description 2
• GSXQTAGTXBIJPX-JOCHJYFZSA-N 1-[(3R)-3-[5-butoxy-1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound CCCCOC1=CN=CC2=C(N=C([C@@H]3CCN(C3)C(=O)C#CC)N12)C1=CC=C(OC2=C(F)C(OC)=CC=C2)C=C1 GSXQTAGTXBIJPX-JOCHJYFZSA-N 0.000 claims description 2
• YVZVHJDRBDBNKF-HXUWFJFHSA-N 1-[(3R)-3-[5-ethoxy-1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound C(C)OC1=CN=CC=2N1C(=NC=2C1=CC=C(C=C1)OC1=C(C(=CC=C1)OC)F)[C@H]1CN(CC1)C(C#CC)=O YVZVHJDRBDBNKF-HXUWFJFHSA-N 0.000 claims description 2
• MTZGKIUVTHAEHA-LJQANCHMSA-N 1-[(3R)-3-[5-ethoxy-1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound C(C)OC1=CN=CC=2N1C(=NC=2C1=CC=C(C=C1)OC1=C(C(=CC=C1)OC)F)[C@H]1CN(CC1)C(C=C)=O MTZGKIUVTHAEHA-LJQANCHMSA-N 0.000 claims description 2
• CGRLJGFNQBTLSK-HXUWFJFHSA-N 1-[(3R)-3-[8-ethoxy-1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound C(C)OC=1C=2N(C=CN=1)C(=NC=2C1=CC=C(C=C1)OC1=C(C(=CC=C1)OC)F)[C@H]1CN(CC1)C(C#CC)=O CGRLJGFNQBTLSK-HXUWFJFHSA-N 0.000 claims description 2
• HGJMRLYCSFNHPU-HXUWFJFHSA-N 1-[(3R)-3-[8-ethyl-1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound CCC1=NC=CN2C(=NC(=C12)C1=CC=C(OC2=C(F)C(OC)=CC=C2)C=C1)[C@@H]1CCN(C1)C(=O)C#CC HGJMRLYCSFNHPU-HXUWFJFHSA-N 0.000 claims description 2
• VJFYKBMXKUSEHO-LJQANCHMSA-N 1-[(3R)-3-[8-ethyl-1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound C(C)C=1C=2N(C=CN=1)C(=NC=2C1=CC=C(C=C1)OC1=C(C(=CC=C1)OC)F)[C@H]1CN(CC1)C(C=C)=O VJFYKBMXKUSEHO-LJQANCHMSA-N 0.000 claims description 2
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
• 125000004414 alkyl thio group Chemical group 0.000 claims description 2
• 230000001387 anti-histamine Effects 0.000 claims description 2
• 239000000739 antihistaminic agent Substances 0.000 claims description 2
• 239000002246 antineoplastic agent Substances 0.000 claims description 2
• 229940041181 antineoplastic drug Drugs 0.000 claims description 2
• 229940046731 calcineurin inhibitors Drugs 0.000 claims description 2
• 125000002837 carbocyclic group Chemical group 0.000 claims description 2
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 2
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
• 239000003795 chemical substances by application Substances 0.000 claims description 2
• 150000003431 steroids Chemical class 0.000 claims description 2
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
• NUUPFGWPWWKFJD-FQEVSTJZSA-N 1-[(2S)-2-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-5-methylimidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3C)[C@H]2N(CCC2)C(C=C)=O)C=CC=C1OC NUUPFGWPWWKFJD-FQEVSTJZSA-N 0.000 claims 2
• FVQPPVMSCHMIKP-IBGZPJMESA-N (2S)-N,N-dimethyl-2-[1-[4-(pyridin-2-ylcarbamoyl)phenyl]-8-(trifluoromethyl)imidazo[1,5-a]pyrazin-3-yl]piperidine-1-carboxamide Chemical compound CN(C)C(=O)N1CCCC[C@H]1c1nc(-c2ccc(cc2)C(=O)Nc2ccccn2)c2c(nccn12)C(F)(F)F FVQPPVMSCHMIKP-IBGZPJMESA-N 0.000 claims 1
• NKZINEMIBDKICC-IBGZPJMESA-N (2S)-N,N-dimethyl-2-[8-(trifluoromethyl)-1-[4-[[4-(trifluoromethyl)pyridin-2-yl]carbamoyl]phenyl]imidazo[1,5-a]pyrazin-3-yl]piperidine-1-carboxamide Chemical compound CN(C(=O)N1[C@@H](CCCC1)C1=NC(=C2N1C=CN=C2C(F)(F)F)C1=CC=C(C=C1)C(NC1=NC=CC(=C1)C(F)(F)F)=O)C NKZINEMIBDKICC-IBGZPJMESA-N 0.000 claims 1
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
• WHRMYOHREPCBCY-WTKRLXQWSA-N (E)-2-[(2S)-2-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidine-1-carbonyl]-4,4-dimethylpent-2-enenitrile Chemical compound COC1=CC=CC(OC2=CC=C(C=C2)C2=C3C=NC=CN3C(=N2)[C@@H]2CCCN2C(=O)C(=C\C(C)(C)C)\C#N)=C1F WHRMYOHREPCBCY-WTKRLXQWSA-N 0.000 claims 1
• SQMVODBQXOPEHZ-PLPWKKLYSA-N (E)-2-[(3R)-3-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-8-methylimidazo[1,5-a]pyrazin-3-yl]pyrrolidine-1-carbonyl]-4,4-dimethylpent-2-enenitrile Chemical compound COC1=CC=CC(OC2=CC=C(C=C2)C2=C3N(C=CN=C3C)C(=N2)[C@@H]2CCN(C2)C(=O)C(=C\C(C)(C)C)\C#N)=C1F SQMVODBQXOPEHZ-PLPWKKLYSA-N 0.000 claims 1
• YUUMOSQDRPMRPM-PLPWKKLYSA-N (E)-2-[(3R)-3-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]piperidine-1-carbonyl]-4,4-dimethylpent-2-enenitrile Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2CN(CCC2)C(=O)\C(\C#N)=C\C(C)(C)C)C=CC=C1OC YUUMOSQDRPMRPM-PLPWKKLYSA-N 0.000 claims 1
• PDUFXWDCWMANTO-NPOAWEEOSA-N (E)-4-[cyclopropyl(methyl)amino]-1-[(3R)-3-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-8-methylimidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-en-1-one Chemical compound COC1=CC=CC(OC2=CC=C(C=C2)C2=C3N(C=CN=C3C)C(=N2)[C@@H]2CCN(C2)C(=O)\C=C\CN(C)C2CC2)=C1F PDUFXWDCWMANTO-NPOAWEEOSA-N 0.000 claims 1
• NRJNMMLXSFYQJU-QFIPXVFZSA-N 1-[(2S)-2-[1-(2-chloro-4-phenoxyphenyl)imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound ClC1=C(C=CC(=C1)OC1=CC=CC=C1)C=1N=C(N2C=1C=NC=C2)[C@H]1N(CCC1)C(C#CC)=O NRJNMMLXSFYQJU-QFIPXVFZSA-N 0.000 claims 1
• UDBPOULXBVHMDF-NRFANRHFSA-N 1-[(2S)-2-[1-(3-chloro-4-phenoxyphenyl)imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound ClC=1C=C(C=CC=1OC1=CC=CC=C1)C=1N=C(N2C=1C=NC=C2)[C@H]1N(CCC1)C(C#CC)=O UDBPOULXBVHMDF-NRFANRHFSA-N 0.000 claims 1
• CZTATRSYRGQCSC-QFIPXVFZSA-N 1-[(2S)-2-[1-[4-(2,3-difluorophenoxy)phenyl]-8-methylimidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C(=NC=C3)C)[C@H]2N(CCCC2)C(C#CC)=O)C=CC=C1F CZTATRSYRGQCSC-QFIPXVFZSA-N 0.000 claims 1
• XPPADZOXSOQVPU-QHCPKHFHSA-N 1-[(2S)-2-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-5,8-dimethylimidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C(=NC=C3C)C)[C@H]2N(CCCC2)C(C#CC)=O)C=CC=C1OC XPPADZOXSOQVPU-QHCPKHFHSA-N 0.000 claims 1
• YDWAXCKDAWKUKA-QFIPXVFZSA-N 1-[(2S)-2-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-5,8-dimethylimidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound COC1=CC=CC(OC2=CC=C(C=C2)C2=C3N(C(=N2)[C@@H]2CCCCN2C(=O)C=C)C(C)=CN=C3C)=C1F YDWAXCKDAWKUKA-QFIPXVFZSA-N 0.000 claims 1
• ULVYLLZCZTYBCL-QFIPXVFZSA-N 1-[(2S)-2-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-5,8-dimethylimidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C(=NC=C3C)C)[C@H]2N(CCC2)C(C#CC)=O)C=CC=C1OC ULVYLLZCZTYBCL-QFIPXVFZSA-N 0.000 claims 1
• RIAQUKQQWBGILP-NRFANRHFSA-N 1-[(2S)-2-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-5,8-dimethylimidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C(=NC=C3C)C)[C@H]2N(CCC2)C(C=C)=O)C=CC=C1OC RIAQUKQQWBGILP-NRFANRHFSA-N 0.000 claims 1
• RUOKSYHBICMNEH-IBGZPJMESA-N 1-[(2S)-2-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-5-methoxyimidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3OC)[C@H]2N(CCC2)C(C=C)=O)C=CC=C1OC RUOKSYHBICMNEH-IBGZPJMESA-N 0.000 claims 1
• TZMAYKHHVLVWNY-QFIPXVFZSA-N 1-[(2S)-2-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-5-methylimidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3C)[C@H]2N(CCCC2)C(C#CC)=O)C=CC=C1OC TZMAYKHHVLVWNY-QFIPXVFZSA-N 0.000 claims 1
• SEVFUFHYUVEYAI-NRFANRHFSA-N 1-[(2S)-2-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-5-methylimidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3C)[C@H]2N(CCCC2)C(C=C)=O)C=CC=C1OC SEVFUFHYUVEYAI-NRFANRHFSA-N 0.000 claims 1
• UJRVARYOAANQOP-NRFANRHFSA-N 1-[(2S)-2-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-5-methylimidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3C)[C@H]2N(CCC2)C(C#CC)=O)C=CC=C1OC UJRVARYOAANQOP-NRFANRHFSA-N 0.000 claims 1
• MBNYQMVZHTXHAC-FQEVSTJZSA-N 1-[(2S)-2-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-6-methylimidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC(=C3)C)[C@H]2N(CCC2)C(C=C)=O)C=CC=C1OC MBNYQMVZHTXHAC-FQEVSTJZSA-N 0.000 claims 1
• ACVXPYLUEICODY-NRFANRHFSA-N 1-[(2S)-2-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-8-(hydroxymethyl)imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound COC1=CC=CC(OC2=CC=C(C=C2)C2=C3N(C=CN=C3CO)C(=N2)[C@@H]2CCCN2C(=O)C#CC)=C1F ACVXPYLUEICODY-NRFANRHFSA-N 0.000 claims 1
• ATHBIZVLJDFNSG-FQEVSTJZSA-N 1-[(2S)-2-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-8-(trifluoromethyl)imidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C(=NC=C3)C(F)(F)F)[C@H]2N(CCCC2)C(C#CC)=O)C=CC=C1OC ATHBIZVLJDFNSG-FQEVSTJZSA-N 0.000 claims 1
• CBPBIDLOWQVSCA-IBGZPJMESA-N 1-[(2S)-2-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-8-(trifluoromethyl)imidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C(=NC=C3)C(F)(F)F)[C@H]2N(CCCC2)C(C=C)=O)C=CC=C1OC CBPBIDLOWQVSCA-IBGZPJMESA-N 0.000 claims 1
• LJKHVTUWGNPBJV-QFIPXVFZSA-N 1-[(2S)-2-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-8-methylimidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C(=NC=C3)C)[C@H]2N(CCCC2)C(C#CC)=O)C=CC=C1OC LJKHVTUWGNPBJV-QFIPXVFZSA-N 0.000 claims 1
• LAVICBXNQHDFND-NRFANRHFSA-N 1-[(2S)-2-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-8-methylimidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound COC1=CC=CC(OC2=CC=C(C=C2)C2=C3N(C=CN=C3C)C(=N2)[C@@H]2CCCCN2C(=O)C=C)=C1F LAVICBXNQHDFND-NRFANRHFSA-N 0.000 claims 1
• ZQYLVZCLCRGVFC-NRFANRHFSA-N 1-[(2S)-2-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-8-methylimidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C(=NC=C3)C)[C@H]2N(CCC2)C(C#CC)=O)C=CC=C1OC ZQYLVZCLCRGVFC-NRFANRHFSA-N 0.000 claims 1
• CUAPTGWHVZTHAR-FQEVSTJZSA-N 1-[(2S)-2-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-8-methylimidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C(=NC=C3)C)[C@H]2N(CCC2)C(C=C)=O)C=CC=C1OC CUAPTGWHVZTHAR-FQEVSTJZSA-N 0.000 claims 1
• ZTCLHDOBTZHJDZ-QFIPXVFZSA-N 1-[(2S)-2-[1-[4-(3-chloro-2-fluorophenoxy)phenyl]-8-methylimidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound ClC=1C(=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C(=NC=C3)C)[C@H]2N(CCCC2)C(C#CC)=O)C=CC=1)F ZTCLHDOBTZHJDZ-QFIPXVFZSA-N 0.000 claims 1
• NKODSCHFCMUWEZ-NRFANRHFSA-N 1-[(2S)-2-[1-[4-(3-chloro-2-fluorophenoxy)phenyl]-8-methylimidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound ClC=1C(=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C(=NC=C3)C)[C@H]2N(CCCC2)C(C=C)=O)C=CC=1)F NKODSCHFCMUWEZ-NRFANRHFSA-N 0.000 claims 1
• LSQBZIAUTORCAW-FQEVSTJZSA-N 1-[(2S)-2-[1-[4-(3-chloro-2-fluorophenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound ClC=1C(=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCC2)C(C#CC)=O)C=CC=1)F LSQBZIAUTORCAW-FQEVSTJZSA-N 0.000 claims 1
• NLDIWSOTEQOPOR-DEOSSOPVSA-N 1-[(2S)-2-[1-[4-(3-fluorophenoxy)phenyl]-8-methylimidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound FC=1C=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C(=NC=C3)C)[C@H]2N(CCCC2)C(C#CC)=O)C=CC=1 NLDIWSOTEQOPOR-DEOSSOPVSA-N 0.000 claims 1
• FHKOZZGOCBKKEJ-QHCPKHFHSA-N 1-[(2S)-2-[1-[4-(3-fluorophenoxy)phenyl]-8-methylimidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound FC=1C=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C(=NC=C3)C)[C@H]2N(CCCC2)C(C=C)=O)C=CC=1 FHKOZZGOCBKKEJ-QHCPKHFHSA-N 0.000 claims 1
• DJPHPQUZLZRFOG-QHCPKHFHSA-N 1-[(2S)-2-[1-[4-(3-fluorophenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound FC=1C=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCCC2)C(C#CC)=O)C=CC=1 DJPHPQUZLZRFOG-QHCPKHFHSA-N 0.000 claims 1
• DCMGSURXIVZBNG-QFIPXVFZSA-N 1-[(2S)-2-[1-[4-(3-methoxy-2-methylphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound COC=1C(=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCC2)C(C#CC)=O)C=CC=1)C DCMGSURXIVZBNG-QFIPXVFZSA-N 0.000 claims 1
• SCPVGOBEOZQNBZ-VWLOTQADSA-N 1-[(2S)-2-[1-[4-(3-methoxyphenoxy)phenyl]-8-methylimidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound COC=1C=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C(=NC=C3)C)[C@H]2N(CCCC2)C(C#CC)=O)C=CC=1 SCPVGOBEOZQNBZ-VWLOTQADSA-N 0.000 claims 1
• WAABGVUIOUVQLG-DEOSSOPVSA-N 1-[(2S)-2-[1-[4-(3-methoxyphenoxy)phenyl]-8-methylimidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound COC1=CC=CC(OC2=CC=C(C=C2)C2=C3N(C=CN=C3C)C(=N2)[C@@H]2CCCCN2C(=O)C=C)=C1 WAABGVUIOUVQLG-DEOSSOPVSA-N 0.000 claims 1
• MIPUPNYIFFSPKR-QFIPXVFZSA-N 1-[(2S)-2-[1-[4-(4-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound COC1=CC=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCC2)C(C=C)=O)C=C1 MIPUPNYIFFSPKR-QFIPXVFZSA-N 0.000 claims 1
• ZFLCLGLAONJVIG-NRFANRHFSA-N 1-[(2S)-2-[1-[4-[(2,3-difluorophenoxy)methyl]phenyl]imidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound FC1=C(OCC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCCC2)C(C=C)=O)C=CC=C1F ZFLCLGLAONJVIG-NRFANRHFSA-N 0.000 claims 1
• GJINTRGPLMBSTG-DEOSSOPVSA-N 1-[(2S)-2-[1-[4-[(2,3-difluorophenyl)methoxy]phenyl]-8-methylimidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound FC1=C(COC2=CC=C(C=C2)C=2N=C(N3C=2C(=NC=C3)C)[C@H]2N(CCCC2)C(C#CC)=O)C=CC=C1F GJINTRGPLMBSTG-DEOSSOPVSA-N 0.000 claims 1
• VICGMWDPSAQRCL-QHCPKHFHSA-N 1-[(2S)-2-[1-[4-[(2,3-difluorophenyl)methoxy]phenyl]-8-methylimidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound CC1=NC=CN2C(=NC(=C12)C1=CC=C(OCC2=C(F)C(F)=CC=C2)C=C1)[C@@H]1CCCCN1C(=O)C=C VICGMWDPSAQRCL-QHCPKHFHSA-N 0.000 claims 1
• WHDBLZNVKJCRHY-NRFANRHFSA-N 1-[(2S)-2-[1-[4-[(2-fluoro-3-methoxyphenoxy)methyl]phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound COC1=CC=CC(OCC2=CC=C(C=C2)C2=C3C=NC=CN3C(=N2)[C@@H]2CCCN2C(=O)C#CC)=C1F WHDBLZNVKJCRHY-NRFANRHFSA-N 0.000 claims 1
• FVTYNIQXCRWCSH-FQEVSTJZSA-N 1-[(2S)-2-[1-[4-[(2-fluoro-3-methoxyphenoxy)methyl]phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound COC1=CC=CC(OCC2=CC=C(C=C2)C2=C3C=NC=CN3C(=N2)[C@@H]2CCCN2C(=O)C=C)=C1F FVTYNIQXCRWCSH-FQEVSTJZSA-N 0.000 claims 1
• YEBVLKZXIAYRLM-QFIPXVFZSA-N 1-[(2S)-2-[1-[4-[(2-fluorophenoxy)methyl]phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound FC1=C(OCC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCC2)C(C#CC)=O)C=CC=C1 YEBVLKZXIAYRLM-QFIPXVFZSA-N 0.000 claims 1
• NPMFULRAZWBOCN-VWLOTQADSA-N 1-[(2S)-2-[1-[4-[(3,4-difluorophenoxy)methyl]phenyl]-8-methylimidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound FC=1C=C(OCC2=CC=C(C=C2)C=2N=C(N3C=2C(=NC=C3)C)[C@H]2N(CCCC2)C(C#CC)=O)C=CC=1F NPMFULRAZWBOCN-VWLOTQADSA-N 0.000 claims 1
• MKUQQPCMHRTNBS-DEOSSOPVSA-N 1-[(2S)-2-[1-[4-[(3,4-difluorophenoxy)methyl]phenyl]-8-methylimidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound CC1=NC=CN2C(=NC(=C12)C1=CC=C(COC2=CC(F)=C(F)C=C2)C=C1)[C@@H]1CCCCN1C(=O)C=C MKUQQPCMHRTNBS-DEOSSOPVSA-N 0.000 claims 1
• QKUUPOHFMIRGDM-QHCPKHFHSA-N 1-[(2S)-2-[1-[4-[(3-chlorophenyl)methoxy]phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound ClC=1C=C(COC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2N(CCC2)C(C#CC)=O)C=CC=1 QKUUPOHFMIRGDM-QHCPKHFHSA-N 0.000 claims 1
• DYQBGWASCMBAGJ-QFIPXVFZSA-N 1-[(2S)-2-[1-[4-[(3-chlorophenyl)methoxy]phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound ClC1=CC=CC(COC2=CC=C(C=C2)C2=C3C=NC=CN3C(=N2)[C@@H]2CCCN2C(=O)C=C)=C1 DYQBGWASCMBAGJ-QFIPXVFZSA-N 0.000 claims 1
• YCATYKOBRFPVPP-VWLOTQADSA-N 1-[(2S)-2-[1-[4-[(3-fluorophenoxy)methyl]phenyl]-8-methylimidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound CC#CC(=O)N1CCCC[C@H]1C1=NC(=C2N1C=CN=C2C)C1=CC=C(COC2=CC(F)=CC=C2)C=C1 YCATYKOBRFPVPP-VWLOTQADSA-N 0.000 claims 1
• LJGQVSNJOCMSKM-DEOSSOPVSA-N 1-[(2S)-2-[1-[4-[(3-fluorophenoxy)methyl]phenyl]-8-methylimidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound FC=1C=C(OCC2=CC=C(C=C2)C=2N=C(N3C=2C(=NC=C3)C)[C@H]2N(CCCC2)C(C=C)=O)C=CC=1 LJGQVSNJOCMSKM-DEOSSOPVSA-N 0.000 claims 1
• MNNPNIXYMOOWHM-DEOSSOPVSA-N 1-[(2S)-2-[1-[4-[(3-fluorophenyl)methoxy]phenyl]-8-methylimidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound FC=1C=C(COC2=CC=C(C=C2)C=2N=C(N3C=2C(=NC=C3)C)[C@H]2N(CCCC2)C(C=C)=O)C=CC=1 MNNPNIXYMOOWHM-DEOSSOPVSA-N 0.000 claims 1
• RGPWUXXVCRCEJP-QHCPKHFHSA-N 1-[(2S)-2-[8-cyclopropyl-1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound C1(CC1)C=1C=2N(C=CN=1)C(=NC=2C1=CC=C(C=C1)OC1=C(C(=CC=C1)OC)F)[C@H]1N(CCCC1)C(C#CC)=O RGPWUXXVCRCEJP-QHCPKHFHSA-N 0.000 claims 1
• UBCYHNKQAXSQGX-DEOSSOPVSA-N 1-[(2S)-2-[8-methyl-1-[3-[[3-(trifluoromethyl)phenyl]methoxy]phenyl]imidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound CC=1C=2N(C=CN=1)C(=NC=2C1=CC(=CC=C1)OCC1=CC(=CC=C1)C(F)(F)F)[C@H]1N(CCCC1)C(C=C)=O UBCYHNKQAXSQGX-DEOSSOPVSA-N 0.000 claims 1
• GVOHVCBAKNUZSV-VWLOTQADSA-N 1-[(2S)-2-[8-methyl-1-[4-(3-methylphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound CC=1C=2N(C=CN=1)C(=NC=2C1=CC=C(C=C1)OC=1C=C(C=CC=1)C)[C@H]1N(CCCC1)C(C#CC)=O GVOHVCBAKNUZSV-VWLOTQADSA-N 0.000 claims 1
• XEZCIZQOCGMSEV-DEOSSOPVSA-N 1-[(2S)-2-[8-methyl-1-[4-(3-methylphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound CC=1C=2N(C=CN=1)C(=NC=2C1=CC=C(C=C1)OC=1C=C(C=CC=1)C)[C@H]1N(CCCC1)C(C=C)=O XEZCIZQOCGMSEV-DEOSSOPVSA-N 0.000 claims 1
• WIRXZTUQUZHNCD-JOCHJYFZSA-N 1-[(3R)-3-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-5,8-dimethylimidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound COC1=CC=CC(OC2=CC=C(C=C2)C2=C3N(C(=N2)[C@@H]2CCCN(C2)C(=O)C#CC)C(C)=CN=C3C)=C1F WIRXZTUQUZHNCD-JOCHJYFZSA-N 0.000 claims 1
• UWKLXSZJGZIJAD-OAQYLSRUSA-N 1-[(3R)-3-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-5,8-dimethylimidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C(=NC=C3C)C)[C@H]2CN(CCC2)C(C=C)=O)C=CC=C1OC UWKLXSZJGZIJAD-OAQYLSRUSA-N 0.000 claims 1
• LBFASZUDMJMURW-OAQYLSRUSA-N 1-[(3R)-3-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-5,8-dimethylimidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C(=NC=C3C)C)[C@H]2CN(CC2)C(C#CC)=O)C=CC=C1OC LBFASZUDMJMURW-OAQYLSRUSA-N 0.000 claims 1
• NOBIRPBXYGVLTL-HXUWFJFHSA-N 1-[(3R)-3-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-5,8-dimethylimidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound COC1=CC=CC(OC2=CC=C(C=C2)C2=C3N(C(=N2)[C@@H]2CCN(C2)C(=O)C=C)C(C)=CN=C3C)=C1F NOBIRPBXYGVLTL-HXUWFJFHSA-N 0.000 claims 1
• AFOJSKCUABNUSA-OAQYLSRUSA-N 1-[(3R)-3-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-5-(2-methoxyethoxy)imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3OCCOC)[C@H]2CN(CC2)C(C#CC)=O)C=CC=C1OC AFOJSKCUABNUSA-OAQYLSRUSA-N 0.000 claims 1
• OYRNQIDIUGTZLE-HXUWFJFHSA-N 1-[(3R)-3-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-5-(2-methoxyethoxy)imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3OCCOC)[C@H]2CN(CC2)C(C=C)=O)C=CC=C1OC OYRNQIDIUGTZLE-HXUWFJFHSA-N 0.000 claims 1
• GVQDSEVKCNBLCR-FKHAVUOCSA-N 1-[(3R)-3-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-5-(oxolan-3-yloxy)imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound COC1=CC=CC(OC2=CC=C(C=C2)C2=C3C=NC=C(OC4CCOC4)N3C(=N2)[C@@H]2CCN(C2)C(=O)C#CC)=C1F GVQDSEVKCNBLCR-FKHAVUOCSA-N 0.000 claims 1
• AJFDDZMPHRNMJM-PSDZMVHGSA-N 1-[(3R)-3-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-5-(oxolan-3-yloxy)imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3OC2COCC2)[C@H]2CN(CC2)C(C=C)=O)C=CC=C1OC AJFDDZMPHRNMJM-PSDZMVHGSA-N 0.000 claims 1
• GGGALSGSFSRJCD-LJQANCHMSA-N 1-[(3R)-3-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-5-methoxyimidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3OC)[C@H]2CN(CC2)C(C#CC)=O)C=CC=C1OC GGGALSGSFSRJCD-LJQANCHMSA-N 0.000 claims 1
• RTVOVKRAIJKDGZ-GOSISDBHSA-N 1-[(3R)-3-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-5-methoxyimidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3OC)[C@H]2CN(CC2)C(C=C)=O)C=CC=C1OC RTVOVKRAIJKDGZ-GOSISDBHSA-N 0.000 claims 1
• CTBQFTLEGVRJKG-OAQYLSRUSA-N 1-[(3R)-3-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-5-methylimidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]but-2-yn-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3C)[C@H]2CN(CCC2)C(C#CC)=O)C=CC=C1OC CTBQFTLEGVRJKG-OAQYLSRUSA-N 0.000 claims 1
• CRTHFWWZJKGMQS-HXUWFJFHSA-N 1-[(3R)-3-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-5-methylimidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound COC1=CC=CC(OC2=CC=C(C=C2)C2=C3C=NC=C(C)N3C(=N2)[C@@H]2CCCN(C2)C(=O)C=C)=C1F CRTHFWWZJKGMQS-HXUWFJFHSA-N 0.000 claims 1
• LNUOCSMCVDKFAD-HXUWFJFHSA-N 1-[(3R)-3-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-5-methylimidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3C)[C@H]2CN(CC2)C(C#CC)=O)C=CC=C1OC LNUOCSMCVDKFAD-HXUWFJFHSA-N 0.000 claims 1
• SSDAJIUOBMFETK-LJQANCHMSA-N 1-[(3R)-3-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-5-methylimidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3C)[C@H]2CN(CC2)C(C=C)=O)C=CC=C1OC SSDAJIUOBMFETK-LJQANCHMSA-N 0.000 claims 1
• WZAJZJNQRRTFNC-OAQYLSRUSA-N 1-[(3R)-3-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-5-propan-2-yloxyimidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound COC1=CC=CC(OC2=CC=C(C=C2)C2=C3C=NC=C(OC(C)C)N3C(=N2)[C@@H]2CCN(C2)C(=O)C#CC)=C1F WZAJZJNQRRTFNC-OAQYLSRUSA-N 0.000 claims 1
• VWPSQBZPACYPFU-HXUWFJFHSA-N 1-[(3R)-3-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-5-propan-2-yloxyimidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3OC(C)C)[C@H]2CN(CC2)C(C=C)=O)C=CC=C1OC VWPSQBZPACYPFU-HXUWFJFHSA-N 0.000 claims 1
• KEZKXKDOYRIFIR-OAQYLSRUSA-N 1-[(3R)-3-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-5-propoxyimidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3OCCC)[C@H]2CN(CC2)C(C#CC)=O)C=CC=C1OC KEZKXKDOYRIFIR-OAQYLSRUSA-N 0.000 claims 1
• XQYQCTODHOZZCL-HXUWFJFHSA-N 1-[(3R)-3-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-5-propoxyimidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound CCCOc1cncc2c(nc([C@@H]3CCN(C3)C(=O)C=C)n12)-c1ccc(Oc2cccc(OC)c2F)cc1 XQYQCTODHOZZCL-HXUWFJFHSA-N 0.000 claims 1
• RFPJNDDDCUJBMJ-LJQANCHMSA-N 1-[(3R)-3-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-8-(fluoromethyl)imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound COC1=CC=CC(OC2=CC=C(C=C2)C2=C3N(C=CN=C3CF)C(=N2)[C@@H]2CCN(C2)C(=O)C#CC)=C1F RFPJNDDDCUJBMJ-LJQANCHMSA-N 0.000 claims 1
• VJGULBOSGOYXBN-LJQANCHMSA-N 1-[(3R)-3-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-8-(hydroxymethyl)imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C(=NC=C3)CO)[C@H]2CN(CC2)C(C#CC)=O)C=CC=C1OC VJGULBOSGOYXBN-LJQANCHMSA-N 0.000 claims 1
• OCNZXLFCMUZDGU-LJQANCHMSA-N 1-[(3R)-3-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-8-methoxyimidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C(=NC=C3)OC)[C@H]2CN(CC2)C(C#CC)=O)C=CC=C1OC OCNZXLFCMUZDGU-LJQANCHMSA-N 0.000 claims 1
• DENRLPSVBYYQRM-HXUWFJFHSA-N 1-[(3R)-3-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-8-methylimidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound COC1=CC=CC(OC2=CC=C(C=C2)C2=C3N(C=CN=C3C)C(=N2)[C@@H]2CCN(C2)C(=O)C#CC)=C1F DENRLPSVBYYQRM-HXUWFJFHSA-N 0.000 claims 1
• NFFNDOKHFAKAKN-LJQANCHMSA-N 1-[(3R)-3-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-8-methylimidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]ethanone Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C(=NC=C3)C)[C@H]2CN(CC2)C(C)=O)C=CC=C1OC NFFNDOKHFAKAKN-LJQANCHMSA-N 0.000 claims 1
• XJJZFUJFJLGFJW-OAQYLSRUSA-N 1-[(3R)-3-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-8-propan-2-ylimidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C(=NC=C3)C(C)C)[C@H]2CN(CC2)C(C#CC)=O)C=CC=C1OC XJJZFUJFJLGFJW-OAQYLSRUSA-N 0.000 claims 1
• ZHEQENMKGFCKJG-HXUWFJFHSA-N 1-[(3R)-3-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-8-propan-2-ylimidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C(=NC=C3)C(C)C)[C@H]2CN(CC2)C(C=C)=O)C=CC=C1OC ZHEQENMKGFCKJG-HXUWFJFHSA-N 0.000 claims 1
• ZSEPBFJSXSLNHH-OAQYLSRUSA-N 1-[(3R)-3-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-8-propylimidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound CCCC1=NC=CN2C(=NC(=C12)C1=CC=C(OC2=C(F)C(OC)=CC=C2)C=C1)[C@@H]1CCN(C1)C(=O)C#CC ZSEPBFJSXSLNHH-OAQYLSRUSA-N 0.000 claims 1
• IIZVWFMVMLKIDV-HXUWFJFHSA-N 1-[(3R)-3-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-8-propylimidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound CCCC1=NC=CN2C(=NC(=C12)C1=CC=C(OC2=C(F)C(OC)=CC=C2)C=C1)[C@@H]1CCN(C1)C(=O)C=C IIZVWFMVMLKIDV-HXUWFJFHSA-N 0.000 claims 1
• OCUKDSIUMGTVDB-OAQYLSRUSA-N 1-[(3R)-3-[5-cyclobutyloxy-1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]but-2-yn-1-one Chemical compound C1(CCC1)OC1=CN=CC=2N1C(=NC=2C1=CC=C(C=C1)OC1=C(C(=CC=C1)OC)F)[C@H]1CN(CC1)C(C#CC)=O OCUKDSIUMGTVDB-OAQYLSRUSA-N 0.000 claims 1
• XCQNLVZZCDWLCV-HXUWFJFHSA-N 1-[(3R)-3-[5-cyclobutyloxy-1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound C1(CCC1)OC1=CN=CC=2N1C(=NC=2C1=CC=C(C=C1)OC1=C(C(=CC=C1)OC)F)[C@H]1CN(CC1)C(C=C)=O XCQNLVZZCDWLCV-HXUWFJFHSA-N 0.000 claims 1
• IXPQSVSLSIESNL-SFHVURJKSA-N 1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-3-[(2S)-1-prop-2-enoylpyrrolidin-2-yl]-7H-imidazo[1,5-a]pyrazin-8-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C(=NC=C3)O)[C@H]2N(CCC2)C(C=C)=O)C=CC=C1OC IXPQSVSLSIESNL-SFHVURJKSA-N 0.000 claims 1
• FLZZXGXTKSSZAP-SFHVURJKSA-N 1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-3-[(2S)-1-prop-2-enoylpyrrolidin-2-yl]imidazo[1,5-a]pyrazine-8-carboxamide Chemical compound COC1=CC=CC(OC2=CC=C(C=C2)C2=C3N(C=CN=C3C(N)=O)C(=N2)[C@@H]2CCCN2C(=O)C=C)=C1F FLZZXGXTKSSZAP-SFHVURJKSA-N 0.000 claims 1
• CMGAIASPWPRWSM-QGZVFWFLSA-N 1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-3-[(3R)-1-prop-2-enoylpyrrolidin-3-yl]-7H-imidazo[1,5-a]pyrazin-8-one Chemical compound COC1=CC=CC(OC2=CC=C(C=C2)C2=C3N(C=CN=C3O)C(=N2)[C@@H]2CCN(C2)C(=O)C=C)=C1F CMGAIASPWPRWSM-QGZVFWFLSA-N 0.000 claims 1
• KWPOJJXYYWFRTC-KRWDZBQOSA-N 2-[(2S)-2-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]pyrrolidin-1-yl]-2-oxoacetamide Chemical compound COC1=CC=CC(OC2=CC=C(C=C2)C2=C3C=NC=CN3C(=N2)[C@@H]2CCCN2C(=O)C(N)=O)=C1F KWPOJJXYYWFRTC-KRWDZBQOSA-N 0.000 claims 1
• CNXWNUSCUNULCE-QGZVFWFLSA-N 2-[(3R)-3-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]piperidin-1-yl]-2-oxoacetamide Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C=NC=C3)[C@H]2CN(CCC2)C(C(=O)N)=O)C=CC=C1OC CNXWNUSCUNULCE-QGZVFWFLSA-N 0.000 claims 1
• LLYWBODUXZZMDU-DEOSSOPVSA-N 3-[(2S)-1-benzylpyrrolidin-2-yl]-1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazine Chemical compound COC1=CC=CC(OC2=CC=C(C=C2)C2=C3C=NC=CN3C(=N2)[C@@H]2CCCN2CC2=CC=CC=C2)=C1F LLYWBODUXZZMDU-DEOSSOPVSA-N 0.000 claims 1
• GSGMNGKNRZMGMO-IBGZPJMESA-N 3-[(2S)-1-but-2-ynoylpyrrolidin-2-yl]-1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-7H-imidazo[1,5-a]pyrazin-8-one Chemical compound FC1=C(OC2=CC=C(C=C2)C=2N=C(N3C=2C(=NC=C3)O)[C@H]2N(CCC2)C(C#CC)=O)C=CC=C1OC GSGMNGKNRZMGMO-IBGZPJMESA-N 0.000 claims 1
• QEWBIBJWHWAFFT-IBGZPJMESA-N 3-[(2S)-1-but-2-ynoylpyrrolidin-2-yl]-1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazine-8-carboxamide Chemical compound COC1=CC=CC(OC2=CC=C(C=C2)C2=C3N(C=CN=C3C(N)=O)C(=N2)[C@@H]2CCCN2C(=O)C#CC)=C1F QEWBIBJWHWAFFT-IBGZPJMESA-N 0.000 claims 1
• NMOPANCSEQMFKE-AREMUKBSSA-N 3-[(3R)-1-benzylpyrrolidin-3-yl]-5-butoxy-1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazine Chemical compound CCCCOC1=CN=CC2=C(N=C([C@@H]3CCN(CC4=CC=CC=C4)C3)N12)C1=CC=C(OC2=C(F)C(OC)=CC=C2)C=C1 NMOPANCSEQMFKE-AREMUKBSSA-N 0.000 claims 1
• HGNZFINAVNJVON-GOSISDBHSA-N 3-[(3R)-1-but-2-ynoylpyrrolidin-3-yl]-1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazine-8-carboxamide Chemical compound COC1=CC=CC(OC2=CC=C(C=C2)C2=C3N(C=CN=C3C(N)=O)C(=N2)[C@@H]2CCN(C2)C(=O)C#CC)=C1F HGNZFINAVNJVON-GOSISDBHSA-N 0.000 claims 1
• VXUNIETWESYIAK-QGZVFWFLSA-N 3-fluoro-4-[5-(methoxymethyl)-3-[(3R)-1-prop-2-enoylpyrrolidin-3-yl]imidazo[1,5-a]pyrazin-1-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound COCC1=CN=CC2=C(N=C([C@@H]3CCN(C3)C(=O)C=C)N12)C1=C(F)C=C(C=C1)C(=O)NC1=NC=CC(=C1)C(F)(F)F VXUNIETWESYIAK-QGZVFWFLSA-N 0.000 claims 1
• CLPLPMGJKBRATR-QHCPKHFHSA-N 4-[3-[(2S)-1-but-2-ynoylpiperidin-2-yl]-5,8-dimethylimidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide Chemical compound CC#CC(=O)N1CCCC[C@H]1C1=NC(=C2N1C(C)=CN=C2C)C1=CC=C(C=C1)C(=O)NC1=NC=CC=C1 CLPLPMGJKBRATR-QHCPKHFHSA-N 0.000 claims 1
• ZIKLLDSCSQOATF-QFIPXVFZSA-N 4-[3-[(2S)-1-but-2-ynoylpiperidin-2-yl]-5-methylimidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide Chemical compound CC#CC(=O)N1CCCC[C@H]1C1=NC(=C2C=NC=C(C)N12)C1=CC=C(C=C1)C(=O)NC1=NC=CC=C1 ZIKLLDSCSQOATF-QFIPXVFZSA-N 0.000 claims 1
• XWPGTRRXRHMABE-FQEVSTJZSA-N 4-[3-[(2S)-1-but-2-ynoylpiperidin-2-yl]-8-(trifluoromethyl)imidazo[1,5-a]pyrazin-1-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound CC#CC(=O)N1CCCC[C@H]1c1nc(-c2ccc(cc2)C(=O)Nc2cc(ccn2)C(F)(F)F)c2c(nccn12)C(F)(F)F XWPGTRRXRHMABE-FQEVSTJZSA-N 0.000 claims 1
• WYAPACJOIMWCMK-FQEVSTJZSA-N 4-[3-[(2S)-1-but-2-ynoylpiperidin-2-yl]-8-(trifluoromethyl)imidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide Chemical compound CC#CC(=O)N1CCCC[C@H]1C1=NC(=C2N1C=CN=C2C(F)(F)F)C1=CC=C(C=C1)C(=O)NC1=NC=CC=C1 WYAPACJOIMWCMK-FQEVSTJZSA-N 0.000 claims 1
• PLNGVXGSQYLWOL-QHCPKHFHSA-N 4-[3-[(2S)-1-but-2-ynoylpiperidin-2-yl]-8-cyclopropylimidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide Chemical compound CC#CC(=O)N1CCCC[C@H]1C1=NC(=C2N1C=CN=C2C1CC1)C1=CC=C(C=C1)C(=O)NC1=NC=CC=C1 PLNGVXGSQYLWOL-QHCPKHFHSA-N 0.000 claims 1
• KVAPZKFEPDXXBQ-QFIPXVFZSA-N 4-[3-[(2S)-1-but-2-ynoylpiperidin-2-yl]-8-methylimidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C#CC)(=O)N1[C@@H](CCCC1)C1=NC(=C2N1C=CN=C2C)C1=CC=C(C(=O)NC2=NC=CC=C2)C=C1 KVAPZKFEPDXXBQ-QFIPXVFZSA-N 0.000 claims 1
• PDRFQNVVCFHQDN-NRFANRHFSA-N 4-[3-[(2S)-1-but-2-ynoylpiperidin-2-yl]imidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide Chemical compound CC#CC(=O)N1CCCC[C@H]1C1=NC(=C2C=NC=CN12)C1=CC=C(C=C1)C(=O)NC1=NC=CC=C1 PDRFQNVVCFHQDN-NRFANRHFSA-N 0.000 claims 1
• YAAYJGFPYPWRRG-QFIPXVFZSA-N 4-[3-[(2S)-1-but-2-ynoylpyrrolidin-2-yl]-5,8-dimethylimidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide Chemical compound CC#CC(=O)N1CCC[C@H]1C1=NC(=C2N1C(C)=CN=C2C)C1=CC=C(C=C1)C(=O)NC1=NC=CC=C1 YAAYJGFPYPWRRG-QFIPXVFZSA-N 0.000 claims 1
• UEAYZHAQCIJXNO-QFIPXVFZSA-N 4-[3-[(2S)-1-but-2-ynoylpyrrolidin-2-yl]-5-(methoxymethyl)imidazo[1,5-a]pyrazin-1-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound COCC1=CN=CC2=C(N=C([C@@H]3CCCN3C(=O)C#CC)N12)C1=CC=C(C=C1)C(=O)NC1=NC=CC(=C1)C(F)(F)F UEAYZHAQCIJXNO-QFIPXVFZSA-N 0.000 claims 1
• DQPXJFITCZQRQP-NRFANRHFSA-N 4-[3-[(2S)-1-but-2-ynoylpyrrolidin-2-yl]-5-methylimidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide Chemical compound CC#CC(=O)N1CCC[C@H]1C1=NC(=C2C=NC=C(C)N12)C1=CC=C(C=C1)C(=O)NC1=NC=CC=C1 DQPXJFITCZQRQP-NRFANRHFSA-N 0.000 claims 1
• KICRCDVAYMFHNC-NRFANRHFSA-N 4-[3-[(2S)-1-but-2-ynoylpyrrolidin-2-yl]-8-(hydroxymethyl)imidazo[1,5-a]pyrazin-1-yl]-3-fluoro-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound CC#CC(=O)N1CCC[C@H]1C1=NC(=C2N1C=CN=C2CO)C1=C(F)C=C(C=C1)C(=O)NC1=NC=CC(=C1)C(F)(F)F KICRCDVAYMFHNC-NRFANRHFSA-N 0.000 claims 1
• LGUGLNIJQNSNTJ-NRFANRHFSA-N 4-[3-[(2S)-1-but-2-ynoylpyrrolidin-2-yl]-8-(hydroxymethyl)imidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide Chemical compound C1[C@@H](C=2N3C=CN=C(C3=C(N=2)C2=CC=C(C=C2)C(=O)NC2=NC=CC=C2)CO)N(CC1)C(=O)C#CC LGUGLNIJQNSNTJ-NRFANRHFSA-N 0.000 claims 1
• MLMBONPOGVHSAB-NRFANRHFSA-N 4-[3-[(2S)-1-but-2-ynoylpyrrolidin-2-yl]imidazo[1,5-a]pyrazin-1-yl]-N-(2-fluoro-3-methoxyphenyl)benzamide Chemical compound C(C#CC)(=O)N1[C@@H](CCC1)C1=NC(=C2N1C=CN=C2)C1=CC=C(C(=O)NC2=C(C(=CC=C2)OC)F)C=C1 MLMBONPOGVHSAB-NRFANRHFSA-N 0.000 claims 1
• MIJVGILLUHEVEW-FQEVSTJZSA-N 4-[3-[(2S)-1-but-2-ynoylpyrrolidin-2-yl]imidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide Chemical compound CC#CC(=O)N1CCC[C@H]1C1=NC(=C2C=NC=CN12)C1=CC=C(C=C1)C(=O)NC1=NC=CC=C1 MIJVGILLUHEVEW-FQEVSTJZSA-N 0.000 claims 1
• VKZGQGOTWDGBFW-IBGZPJMESA-N 4-[3-[(2S)-1-prop-2-enoylpiperidin-2-yl]-8-(trifluoromethyl)imidazo[1,5-a]pyrazin-1-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound FC(F)(F)C1=CC(NC(=O)C2=CC=C(C=C2)C2=C3N(C=CN=C3C(F)(F)F)C(=N2)[C@@H]2CCCCN2C(=O)C=C)=NC=C1 VKZGQGOTWDGBFW-IBGZPJMESA-N 0.000 claims 1
• NHWPWSGARXTBMC-IBGZPJMESA-N 4-[3-[(2S)-1-prop-2-enoylpiperidin-2-yl]-8-(trifluoromethyl)imidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide Chemical compound FC(F)(F)C1=NC=CN2C(=NC(=C12)C1=CC=C(C=C1)C(=O)NC1=NC=CC=C1)[C@@H]1CCCCN1C(=O)C=C NHWPWSGARXTBMC-IBGZPJMESA-N 0.000 claims 1
• OMYVZMIGRBHTBA-FQEVSTJZSA-N 4-[3-[(2S)-1-prop-2-enoylpiperidin-2-yl]imidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide Chemical compound C=CC(=O)N1CCCC[C@H]1C1=NC(=C2C=NC=CN12)C1=CC=C(C=C1)C(=O)NC1=NC=CC=C1 OMYVZMIGRBHTBA-FQEVSTJZSA-N 0.000 claims 1
• OUCBWTVMMFAYSY-HSZRJFAPSA-N 4-[3-[(3R)-1-but-2-ynoylpiperidin-3-yl]-5,8-dimethylimidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide Chemical compound CC#CC(=O)N1CCC[C@H](C1)C1=NC(=C2N1C(C)=CN=C2C)C1=CC=C(C=C1)C(=O)NC1=NC=CC=C1 OUCBWTVMMFAYSY-HSZRJFAPSA-N 0.000 claims 1
• QLSZDVJEMRFOSU-JOCHJYFZSA-N 4-[3-[(3R)-1-but-2-ynoylpiperidin-3-yl]-5-methylimidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide Chemical compound CC#CC(=O)N1CCC[C@H](C1)C1=NC(=C2C=NC=C(C)N12)C1=CC=C(C=C1)C(=O)NC1=NC=CC=C1 QLSZDVJEMRFOSU-JOCHJYFZSA-N 0.000 claims 1
• GOSOLPBVGCZZQA-OAQYLSRUSA-N 4-[3-[(3R)-1-but-2-ynoylpiperidin-3-yl]imidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide Chemical compound CC#CC(=O)N1CCC[C@H](C1)C1=NC(=C2C=NC=CN12)C1=CC=C(C=C1)C(=O)NC1=NC=CC=C1 GOSOLPBVGCZZQA-OAQYLSRUSA-N 0.000 claims 1
• RLMVBNZYDCXPPN-JOCHJYFZSA-N 4-[3-[(3R)-1-but-2-ynoylpyrrolidin-3-yl]-5,8-dimethylimidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide Chemical compound CC#CC(=O)N1CC[C@H](C1)C1=NC(=C2N1C(C)=CN=C2C)C1=CC=C(C=C1)C(=O)NC1=NC=CC=C1 RLMVBNZYDCXPPN-JOCHJYFZSA-N 0.000 claims 1
• LRDXPPNPQIFKMU-GOSISDBHSA-N 4-[3-[(3R)-1-but-2-ynoylpyrrolidin-3-yl]-5-(methoxymethyl)imidazo[1,5-a]pyrazin-1-yl]-3-fluoro-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound COCC1=CN=CC2=C(N=C([C@@H]3CCN(C3)C(=O)C#CC)N12)C1=C(F)C=C(C=C1)C(=O)NC1=NC=CC(=C1)C(F)(F)F LRDXPPNPQIFKMU-GOSISDBHSA-N 0.000 claims 1
• QJWYRBLPBAGNDL-HXUWFJFHSA-N 4-[3-[(3R)-1-but-2-ynoylpyrrolidin-3-yl]-5-(methoxymethyl)imidazo[1,5-a]pyrazin-1-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound COCC1=CN=CC2=C(N=C([C@@H]3CCN(C3)C(=O)C#CC)N12)C1=CC=C(C=C1)C(=O)NC1=NC=CC(=C1)C(F)(F)F QJWYRBLPBAGNDL-HXUWFJFHSA-N 0.000 claims 1
• NEZLYJBYSIMLDO-JOCHJYFZSA-N 4-[3-[(3R)-1-but-2-ynoylpyrrolidin-3-yl]-5-ethoxy-8-methylimidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide Chemical compound CCOC1=CN=C(C)C2=C(N=C([C@@H]3CCN(C3)C(=O)C#CC)N12)C1=CC=C(C=C1)C(=O)NC1=NC=CC=C1 NEZLYJBYSIMLDO-JOCHJYFZSA-N 0.000 claims 1
• XMISOYHSCKFWGA-OAQYLSRUSA-N 4-[3-[(3R)-1-but-2-ynoylpyrrolidin-3-yl]-5-ethoxyimidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide Chemical compound CCOC1=CN=CC2=C(N=C([C@@H]3CCN(C3)C(=O)C#CC)N12)C1=CC=C(C=C1)C(=O)NC1=NC=CC=C1 XMISOYHSCKFWGA-OAQYLSRUSA-N 0.000 claims 1
• GWPUQWFKLIKWAQ-OAQYLSRUSA-N 4-[3-[(3R)-1-but-2-ynoylpyrrolidin-3-yl]-5-methylimidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide Chemical compound CC#CC(=O)N1CC[C@H](C1)C1=NC(=C2C=NC=C(C)N12)C1=CC=C(C=C1)C(=O)NC1=NC=CC=C1 GWPUQWFKLIKWAQ-OAQYLSRUSA-N 0.000 claims 1
• NBLTXNQVNCCJKH-QGZVFWFLSA-N 4-[3-[(3R)-1-but-2-ynoylpyrrolidin-3-yl]imidazo[1,5-a]pyrazin-1-yl]-3-fluoro-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C(C#CC)(=O)N1C[C@@H](CC1)C1=NC(=C2N1C=CN=C2)C1=C(C=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)F NBLTXNQVNCCJKH-QGZVFWFLSA-N 0.000 claims 1
• IIZLCMZPUUGCFV-LJQANCHMSA-N 4-[3-[(3R)-1-but-2-ynoylpyrrolidin-3-yl]imidazo[1,5-a]pyrazin-1-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound CC#CC(=O)N1CC[C@H](C1)C1=NC(=C2C=NC=CN12)C1=CC=C(C=C1)C(=O)NC1=NC=CC(=C1)C(F)(F)F IIZLCMZPUUGCFV-LJQANCHMSA-N 0.000 claims 1
• QSKBYRCFAPFUKO-HXUWFJFHSA-N 4-[3-[(3R)-1-but-2-ynoylpyrrolidin-3-yl]imidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide Chemical compound CC#CC(=O)N1CC[C@H](C1)C1=NC(=C2C=NC=CN12)C1=CC=C(C=C1)C(=O)NC1=NC=CC=C1 QSKBYRCFAPFUKO-HXUWFJFHSA-N 0.000 claims 1
• UTAUXPZOCLZNEZ-GOSISDBHSA-N 4-[3-[(3R)-1-prop-2-enoylpyrrolidin-3-yl]imidazo[1,5-a]pyrazin-1-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound FC(F)(F)C1=CC(NC(=O)C2=CC=C(C=C2)C2=C3C=NC=CN3C(=N2)[C@@H]2CCN(C2)C(=O)C=C)=NC=C1 UTAUXPZOCLZNEZ-GOSISDBHSA-N 0.000 claims 1
• JWWQEEHPCNMZMX-LJQANCHMSA-N 4-[3-[(3R)-1-prop-2-enoylpyrrolidin-3-yl]imidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide Chemical compound C=CC(=O)N1CC[C@H](C1)C1=NC(=C2C=NC=CN12)C1=CC=C(C=C1)C(=O)NC1=NC=CC=C1 JWWQEEHPCNMZMX-LJQANCHMSA-N 0.000 claims 1
• OMYOGHDRWOVQFY-QFIPXVFZSA-N 4-[5,8-dimethyl-3-[(2S)-1-prop-2-enoylpiperidin-2-yl]imidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide Chemical compound Cc1cnc(C)c2c(nc([C@@H]3CCCCN3C(=O)C=C)n12)-c1ccc(cc1)C(=O)Nc1ccccn1 OMYOGHDRWOVQFY-QFIPXVFZSA-N 0.000 claims 1
• GDKKVMIRAZECBY-NRFANRHFSA-N 4-[5,8-dimethyl-3-[(2S)-1-prop-2-enoylpyrrolidin-2-yl]imidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide Chemical compound CC1=CN=C(C)C2=C(N=C([C@@H]3CCCN3C(=O)C=C)N12)C1=CC=C(C=C1)C(=O)NC1=NC=CC=C1 GDKKVMIRAZECBY-NRFANRHFSA-N 0.000 claims 1
• JROTZMHDRZUCBW-JOCHJYFZSA-N 4-[5,8-dimethyl-3-[(3R)-1-prop-2-enoylpiperidin-3-yl]imidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide Chemical compound CC1=CN=C(C)C2=C(N=C([C@@H]3CCCN(C3)C(=O)C=C)N12)C1=CC=C(C=C1)C(=O)NC1=NC=CC=C1 JROTZMHDRZUCBW-JOCHJYFZSA-N 0.000 claims 1
• KVZGUGZVCWSDIG-OAQYLSRUSA-N 4-[5,8-dimethyl-3-[(3R)-1-prop-2-enoylpyrrolidin-3-yl]imidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide Chemical compound C(=O)(C=C)N1C[C@@H](CC1)C=1N2C(=CN=C(C)C2=C(C2=CC=C(C(=O)NC3=CC=CC=N3)C=C2)N=1)C KVZGUGZVCWSDIG-OAQYLSRUSA-N 0.000 claims 1
• WMDRZMUBDHPJIQ-NRFANRHFSA-N 4-[5-(methoxymethyl)-3-[(2S)-1-prop-2-enoylpyrrolidin-2-yl]imidazo[1,5-a]pyrazin-1-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound COCC1=CN=CC2=C(N=C([C@@H]3CCCN3C(=O)C=C)N12)C1=CC=C(C=C1)C(=O)NC1=NC=CC(=C1)C(F)(F)F WMDRZMUBDHPJIQ-NRFANRHFSA-N 0.000 claims 1
• POHPCHVWUSCUTQ-HXUWFJFHSA-N 4-[5-ethoxy-3-[(3R)-1-prop-2-enoylpyrrolidin-3-yl]imidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide Chemical compound CCOC1=CN=CC2=C(N=C([C@@H]3CCN(C3)C(=O)C=C)N12)C1=CC=C(C=C1)C(=O)NC1=NC=CC=C1 POHPCHVWUSCUTQ-HXUWFJFHSA-N 0.000 claims 1
• GOVLELHLOJQRBR-OAQYLSRUSA-N 4-[5-ethoxy-8-methyl-3-[(3R)-1-prop-2-enoylpyrrolidin-3-yl]imidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide Chemical compound CCOC1=CN=C(C)C2=C(N=C([C@@H]3CCN(C3)C(=O)C=C)N12)C1=CC=C(C=C1)C(=O)NC1=NC=CC=C1 GOVLELHLOJQRBR-OAQYLSRUSA-N 0.000 claims 1
• QSVUOEKQLRWYDB-NRFANRHFSA-N 4-[5-methyl-3-[(2S)-1-prop-2-enoylpiperidin-2-yl]imidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide Chemical compound CC1=CN=CC2=C(N=C([C@@H]3CCCCN3C(=O)C=C)N12)C1=CC=C(C=C1)C(=O)NC1=NC=CC=C1 QSVUOEKQLRWYDB-NRFANRHFSA-N 0.000 claims 1
• BMFIRUJSFIMFJV-FQEVSTJZSA-N 4-[5-methyl-3-[(2S)-1-prop-2-enoylpyrrolidin-2-yl]imidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide Chemical compound CC1=CN=CC2=C(N=C([C@@H]3CCCN3C(=O)C=C)N12)C1=CC=C(C=C1)C(=O)NC1=NC=CC=C1 BMFIRUJSFIMFJV-FQEVSTJZSA-N 0.000 claims 1
• VGQNMNLJRDWJML-OAQYLSRUSA-N 4-[5-methyl-3-[(3R)-1-prop-2-enoylpiperidin-3-yl]imidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide Chemical compound CC1=CN=CC2=C(N=C([C@@H]3CCCN(C3)C(=O)C=C)N12)C1=CC=C(C=C1)C(=O)NC1=NC=CC=C1 VGQNMNLJRDWJML-OAQYLSRUSA-N 0.000 claims 1
• MKSKSTRQDMKXTD-HXUWFJFHSA-N 4-[5-methyl-3-[(3R)-1-prop-2-enoylpyrrolidin-3-yl]imidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide Chemical compound CC1=CN=CC2=C(N=C([C@@H]3CCN(C3)C(=O)C=C)N12)C1=CC=C(C=C1)C(=O)NC1=NC=CC=C1 MKSKSTRQDMKXTD-HXUWFJFHSA-N 0.000 claims 1
• BMLKFRTYCOFOCL-NRFANRHFSA-N 4-[8-(fluoromethyl)-3-[(2S)-1-prop-1-ynylpyrrolidin-2-yl]imidazo[1,5-a]pyrazin-1-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound FCC=1C=2N(C=CN=1)C(=NC=2C1=CC=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)[C@H]1N(CCC1)C#CC BMLKFRTYCOFOCL-NRFANRHFSA-N 0.000 claims 1
• CTMVVVFREXQDNI-NRFANRHFSA-N 4-[8-(hydroxymethyl)-3-[(2S)-1-prop-1-ynylpyrrolidin-2-yl]imidazo[1,5-a]pyrazin-1-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound OCC=1C=2N(C=CN=1)C(=NC=2C1=CC=C(C(=O)NC2=NC=CC(=C2)C(F)(F)F)C=C1)[C@H]1N(CCC1)C#CC CTMVVVFREXQDNI-NRFANRHFSA-N 0.000 claims 1
• BOCSASRUGIUWRT-QFIPXVFZSA-N 4-[8-cyclopropyl-3-[(2S)-1-prop-2-enoylpiperidin-2-yl]imidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide Chemical compound C(C=C)(=O)N1[C@@H](CCCC1)C1=NC(=C2N1C=CN=C2C1CC1)C1=CC=C(C(=O)NC2=NC=CC=C2)C=C1 BOCSASRUGIUWRT-QFIPXVFZSA-N 0.000 claims 1
• NLIRHAUCBPRVPV-NRFANRHFSA-N 4-[8-cyclopropyl-3-[(2S)-1-prop-2-enoylpyrrolidin-2-yl]imidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide Chemical compound C=CC(=O)N1CCC[C@H]1C1=NC(=C2N1C=CN=C2C1CC1)C1=CC=C(C=C1)C(=O)NC1=NC=CC=C1 NLIRHAUCBPRVPV-NRFANRHFSA-N 0.000 claims 1
• OHGLGGQUEYPLNM-NRFANRHFSA-N 4-[8-methyl-3-[(2S)-1-prop-2-enoylpiperidin-2-yl]imidazo[1,5-a]pyrazin-1-yl]-N-pyridin-2-ylbenzamide Chemical compound CC1=NC=CN2C(=NC(=C12)C1=CC=C(C=C1)C(=O)NC1=NC=CC=C1)[C@@H]1CCCCN1C(=O)C=C OHGLGGQUEYPLNM-NRFANRHFSA-N 0.000 claims 1
• QRJLTEOCLGOUEZ-UHFFFAOYSA-N 7-[1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazin-3-yl]-2-methyl-4,4a,5,6,7,8-hexahydro-3H-pyrido[1,2-c]pyrimidin-1-one Chemical compound COC1=CC=CC(OC2=CC=C(C=C2)C2=C3C=NC=CN3C(=N2)C2CCC3CCN(C)C(=O)N3C2)=C1F QRJLTEOCLGOUEZ-UHFFFAOYSA-N 0.000 claims 1
• AFVWJCHOBNTNID-FQEVSTJZSA-N N-(2-fluoro-3-methoxyphenyl)-4-[3-[(2S)-1-prop-2-enoylpyrrolidin-2-yl]imidazo[1,5-a]pyrazin-1-yl]benzamide Chemical compound C(C=C)(=O)N1[C@@H](CCC1)C1=NC(=C2N1C=CN=C2)C1=CC=C(C(=O)NC2=C(C(=CC=C2)OC)F)C=C1 AFVWJCHOBNTNID-FQEVSTJZSA-N 0.000 claims 1
• KDCHZHNXPWZUHB-OAQYLSRUSA-N [3-[(3R)-1-but-2-ynoylpyrrolidin-3-yl]-1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazin-8-yl]methyl acetate Chemical compound COc1cccc(Oc2ccc(cc2)-c2nc([C@@H]3CCN(C3)C(=O)C#CC)n3ccnc(COC(C)=O)c23)c1F KDCHZHNXPWZUHB-OAQYLSRUSA-N 0.000 claims 1
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
• PDTDBQPRWJBGOE-FQEVSTJZSA-N methyl 1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]-3-[(2S)-1-prop-2-enoylpiperidin-2-yl]imidazo[1,5-a]pyrazine-8-carboxylate Chemical compound COC(=O)C1=NC=CN2C(=NC(=C12)C1=CC=C(OC2=C(F)C(OC)=CC=C2)C=C1)[C@@H]1CCCCN1C(=O)C=C PDTDBQPRWJBGOE-FQEVSTJZSA-N 0.000 claims 1
• SUQYIWXLTWRDRC-NRFANRHFSA-N methyl 3-[(2S)-1-but-2-ynoylpiperidin-2-yl]-1-[4-(2-fluoro-3-methoxyphenoxy)phenyl]imidazo[1,5-a]pyrazine-8-carboxylate Chemical compound COC(=O)C1=NC=CN2C(=NC(=C12)C1=CC=C(OC2=C(F)C(OC)=CC=C2)C=C1)[C@@H]1CCCCN1C(=O)C#CC SUQYIWXLTWRDRC-NRFANRHFSA-N 0.000 claims 1
• 239000003112 inhibitor Substances 0.000 abstract description 5
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• 239000000243 solution Substances 0.000 description 70
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• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 47
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• 239000012044 organic layer Substances 0.000 description 41
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• 101150041968 CDC13 gene Proteins 0.000 description 35
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• 229910000027 potassium carbonate Inorganic materials 0.000 description 25
• 239000002904 solvent Substances 0.000 description 22
• 238000004809 thin layer chromatography Methods 0.000 description 21
• 239000000047 product Substances 0.000 description 20
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• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
• 230000000694 effects Effects 0.000 description 18
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