JPWO2020163544A5 - - Google Patents
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- JPWO2020163544A5 JPWO2020163544A5 JP2021546239A JP2021546239A JPWO2020163544A5 JP WO2020163544 A5 JPWO2020163544 A5 JP WO2020163544A5 JP 2021546239 A JP2021546239 A JP 2021546239A JP 2021546239 A JP2021546239 A JP 2021546239A JP WO2020163544 A5 JPWO2020163544 A5 JP WO2020163544A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- unsubstituted
- pharmaceutically acceptable
- alkyl
- hydrogen
- Prior art date
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 150
- 150000003839 salts Chemical class 0.000 claims description 149
- 239000012453 solvate Substances 0.000 claims description 142
- 229910052739 hydrogen Inorganic materials 0.000 claims description 115
- 239000001257 hydrogen Substances 0.000 claims description 115
- 150000002431 hydrogen Chemical class 0.000 claims description 73
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 70
- 229910052805 deuterium Inorganic materials 0.000 claims description 70
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
- 125000001072 heteroaryl group Chemical group 0.000 claims description 33
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 21
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 19
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 17
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000003566 oxetanyl group Chemical group 0.000 claims description 9
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims description 8
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 7
- -1 2-hydroxy-phenyl Chemical group 0.000 claims description 7
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000004406 C3-C8 cycloalkylene group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 5
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 108020004999 messenger RNA Proteins 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- NITSAQJPBJYMFL-UHFFFAOYSA-N pyridin-4-ol Chemical compound O=C1C=[C]NC=C1 NITSAQJPBJYMFL-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- SPRGQMPFYGHDMC-QQOZLPODSA-N 6-[5-[[(1R,3S,4S,5R)-4-fluoro-1-methyl-8-azabicyclo[3.2.1]oct-6-en-3-yl]-methylamino]pyrazin-2-yl]isoquinolin-7-ol Chemical compound F[C@@H]1[C@H](C[C@@]2(C=C[C@H]1N2)C)N(C=1N=CC(=NC=1)C=1C=C2C=CN=CC2=CC=1O)C SPRGQMPFYGHDMC-QQOZLPODSA-N 0.000 description 2
- 125000004450 alkenylene group Chemical group 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- 108091032973 (ribonucleotides)n+m Proteins 0.000 description 1
- QPSLZPFHAFIRND-MLAUGJPMSA-N 2-[5-[(E)-[(1S,2R,5R)-2-fluoro-1,5-dimethyl-9-azabicyclo[3.3.1]nonan-3-ylidene]methyl]pyrazin-2-yl]-5-imidazol-1-ylphenol Chemical compound F[C@H]\1[C@@]2(CCC[C@](C/C/1=C\C=1N=CC(=NC=1)C1=C(C=C(C=C1)N1C=NC=C1)O)(N2)C)C QPSLZPFHAFIRND-MLAUGJPMSA-N 0.000 description 1
- ZQSKPJARNCCCSP-NEJWMWPNSA-N 2-[5-[(E)-[(1S,2R,5R)-2-fluoro-1-methyl-9-azabicyclo[3.3.1]nonan-3-ylidene]methyl]pyrazin-2-yl]-5-imidazol-1-ylphenol Chemical compound F[C@H]\1[C@@]2(CCC[C@H](C/C/1=C\C=1N=CC(=NC=1)C1=C(C=C(C=C1)N1C=NC=C1)O)N2)C ZQSKPJARNCCCSP-NEJWMWPNSA-N 0.000 description 1
- BDGMLBJYDVKAOX-OXVVKLCVSA-N 2-[5-[(E)-[(1S,2R,5R)-2-fluoro-9-azabicyclo[3.3.1]nonan-3-ylidene]methyl]pyrazin-2-yl]-5-imidazol-1-ylphenol Chemical compound F[C@H]\1[C@@H]2CCC[C@H](C/C/1=C\C=1N=CC(=NC=1)C1=C(C=C(C=C1)N1C=NC=C1)O)N2 BDGMLBJYDVKAOX-OXVVKLCVSA-N 0.000 description 1
- VPCKKFFQTYTBQS-UHEIQRFUSA-N 2-[5-[(E)-[(1S,2R,5S)-2-fluoro-1,5-dimethyl-8-azabicyclo[3.2.1]oct-6-en-3-ylidene]methyl]pyrazin-2-yl]-5-(2-methoxypyridin-4-yl)phenol Chemical compound F[C@H]\1[C@@]2(C=C[C@](C/C/1=C\C=1N=CC(=NC=1)C1=C(C=C(C=C1)C1=CC(=NC=C1)OC)O)(N2)C)C VPCKKFFQTYTBQS-UHEIQRFUSA-N 0.000 description 1
- SDZJTTSCSKXQTL-WOSDYRLDSA-N 2-[5-[(E)-[(1S,2R,5S)-2-fluoro-1-methyl-8-azabicyclo[3.2.1]oct-6-en-3-ylidene]methyl]pyrazin-2-yl]-5-(2-methoxypyridin-4-yl)phenol Chemical compound F[C@H]\1[C@@]2(C=C[C@H](C/C/1=C\C=1N=CC(=NC=1)C1=C(C=C(C=C1)C1=CC(=NC=C1)OC)O)N2)C SDZJTTSCSKXQTL-WOSDYRLDSA-N 0.000 description 1
- XOGPROUXAALAHN-VAMZGIEHSA-N 2-[5-[(E)-[(1S,2R,5S)-2-fluoro-8-azabicyclo[3.2.1]oct-6-en-3-ylidene]methyl]pyrazin-2-yl]-5-(2-methoxypyridin-4-yl)phenol Chemical compound F[C@H]\1[C@@H]2C=C[C@H](C/C/1=C\C=1N=CC(=NC=1)C1=C(C=C(C=C1)C1=CC(=NC=C1)OC)O)N2 XOGPROUXAALAHN-VAMZGIEHSA-N 0.000 description 1
- LYKMRHWOZHGSOZ-NZVCLXNJSA-N 2-[5-[(E)-[(1S,2S,5R)-2-fluoro-1,5-dimethyl-8-azabicyclo[3.2.1]octan-3-ylidene]methyl]pyrazin-2-yl]-5-(5-methyltetrazol-2-yl)phenol Chemical compound F[C@@H]\1[C@@]2(CC[C@](C/C/1=C\C=1N=CC(=NC=1)C1=C(C=C(C=C1)N1N=C(N=N1)C)O)(N2)C)C LYKMRHWOZHGSOZ-NZVCLXNJSA-N 0.000 description 1
- FHCDRBPWJSSIES-XYPORCBCSA-N 2-[5-[(E)-[(1S,2S,5R)-2-fluoro-1-methyl-8-azabicyclo[3.2.1]octan-3-ylidene]methyl]pyrazin-2-yl]-5-(5-methyltetrazol-2-yl)phenol Chemical compound F[C@@H]\1[C@@]2(CC[C@H](C/C/1=C\C=1N=CC(=NC=1)C1=C(C=C(C=C1)N1N=C(N=N1)C)O)N2)C FHCDRBPWJSSIES-XYPORCBCSA-N 0.000 description 1
- BPKMIPJUNCZMMN-ZNXIFXFFSA-N 2-[5-[(E)-[(1S,2S,5R)-2-fluoro-8-azabicyclo[3.2.1]octan-3-ylidene]methyl]pyrazin-2-yl]-5-(5-methyltetrazol-2-yl)phenol Chemical compound F[C@@H]\1[C@@H]2CC[C@H](C/C/1=C\C=1N=CC(=NC=1)C1=C(C=C(C=C1)N1N=C(N=N1)C)O)N2 BPKMIPJUNCZMMN-ZNXIFXFFSA-N 0.000 description 1
- VWKVTHRSTQRUEF-YBXKOJPMSA-N 2-[5-[(E)-[(1S,2S,5S,6R)-1,5-dideuterio-2,6-difluoro-8-azabicyclo[3.2.1]octan-3-ylidene]methyl]pyrazin-2-yl]-5-imidazol-1-ylphenol Chemical compound F[C@@H]\1[C@@]2(C[C@H]([C@](C/C/1=C\C=1N=CC(=NC=1)C1=C(C=C(C=C1)N1C=NC=C1)O)(N2)[2H])F)[2H] VWKVTHRSTQRUEF-YBXKOJPMSA-N 0.000 description 1
- HHDIGQRAOFEALO-PIHQKDGRSA-N 2-[5-[(E)-[(1S,2S,5S,6R)-2,6-difluoro-1,5-dimethyl-8-azabicyclo[3.2.1]octan-3-ylidene]methyl]pyrazin-2-yl]-5-imidazol-1-ylphenol Chemical compound F[C@@H]\1[C@@]2(C[C@H]([C@](C/C/1=C\C=1N=CC(=NC=1)C1=C(C=C(C=C1)N1C=NC=C1)O)(N2)C)F)C HHDIGQRAOFEALO-PIHQKDGRSA-N 0.000 description 1
- OFOXHTJLYCFACU-TUTVWWFUSA-N 2-[5-[(E)-[(1S,2S,5S,6R)-2-fluoro-6-methoxy-1,5-dimethyl-8-azabicyclo[3.2.1]octan-3-ylidene]methyl]pyrazin-2-yl]-5-imidazol-1-ylphenol Chemical compound F[C@@H]\1[C@@]2(C[C@H]([C@](C/C/1=C\C=1N=CC(=NC=1)C1=C(C=C(C=C1)N1C=NC=C1)O)(N2)C)OC)C OFOXHTJLYCFACU-TUTVWWFUSA-N 0.000 description 1
- QXCWCSXJHTWRLP-IIFVTBLASA-N 2-[5-[(E)-[(1S,2S,5S,6R)-2-fluoro-6-methoxy-1-methyl-8-azabicyclo[3.2.1]octan-3-ylidene]methyl]pyrazin-2-yl]-5-imidazol-1-ylphenol Chemical compound F[C@@H]\1[C@@]2(C[C@H]([C@H](C/C/1=C\C=1N=CC(=NC=1)C1=C(C=C(C=C1)N1C=NC=C1)O)N2)OC)C QXCWCSXJHTWRLP-IIFVTBLASA-N 0.000 description 1
- FPJHNEUFLKFJBM-DFPXOIHOSA-N 2-[5-[(E)-[(1S,2S,5S,6R)-2-fluoro-6-methoxy-8-azabicyclo[3.2.1]octan-3-ylidene]methyl]pyrazin-2-yl]-5-imidazol-1-ylphenol Chemical compound F[C@@H]\1[C@@H]2C[C@H]([C@H](C/C/1=C\C=1N=CC(=NC=1)C1=C(C=C(C=C1)N1C=NC=C1)O)N2)OC FPJHNEUFLKFJBM-DFPXOIHOSA-N 0.000 description 1
- WABIUEWTGWOFBN-DQUHTYBESA-N 2-[5-[(E)-[(1S,2S,5S,6R)-5-deuterio-2,6-difluoro-1-methyl-8-azabicyclo[3.2.1]octan-3-ylidene]methyl]pyrazin-2-yl]-5-imidazol-1-ylphenol Chemical compound F[C@@H]\1[C@@]2(C[C@H]([C@](C/C/1=C\C=1N=CC(=NC=1)C1=C(C=C(C=C1)N1C=NC=C1)O)(N2)[2H])F)C WABIUEWTGWOFBN-DQUHTYBESA-N 0.000 description 1
- HHDIGQRAOFEALO-PGDBHTRUSA-N 2-[5-[(E)-[(1S,2S,5S,6S)-2,6-difluoro-1,5-dimethyl-8-azabicyclo[3.2.1]octan-3-ylidene]methyl]pyrazin-2-yl]-5-imidazol-1-ylphenol Chemical compound F[C@@H]\1[C@@]2(C[C@@H]([C@](C/C/1=C\C=1N=CC(=NC=1)C1=C(C=C(C=C1)N1C=NC=C1)O)(N2)C)F)C HHDIGQRAOFEALO-PGDBHTRUSA-N 0.000 description 1
- WABIUEWTGWOFBN-CIEDCVASSA-N 2-[5-[(E)-[(1S,2S,5S,6S)-2,6-difluoro-1-methyl-8-azabicyclo[3.2.1]octan-3-ylidene]methyl]pyrazin-2-yl]-5-imidazol-1-ylphenol Chemical compound F[C@@H]\1[C@@]2(C[C@@H]([C@H](C/C/1=C\C=1N=CC(=NC=1)C1=C(C=C(C=C1)N1C=NC=C1)O)N2)F)C WABIUEWTGWOFBN-CIEDCVASSA-N 0.000 description 1
- VWKVTHRSTQRUEF-BLVBZAOUSA-N 2-[5-[(E)-[(1S,2S,5S,6S)-2,6-difluoro-8-azabicyclo[3.2.1]octan-3-ylidene]methyl]pyrazin-2-yl]-5-imidazol-1-ylphenol Chemical compound F[C@@H]\1[C@@H]2C[C@@H]([C@H](C/C/1=C\C=1N=CC(=NC=1)C1=C(C=C(C=C1)N1C=NC=C1)O)N2)F VWKVTHRSTQRUEF-BLVBZAOUSA-N 0.000 description 1
- PTBOVFRWTZROKC-BZYPTDMQSA-N 2-[5-[(Z)-[(1R,2R,5R)-6,6-difluoro-2-methoxy-1,5-dimethyl-8-azabicyclo[3.2.1]octan-3-ylidene]methyl]pyrazin-2-yl]-5-imidazol-1-ylphenol Chemical compound FC1([C@]2(C/C(/[C@H]([C@@](C1)(N2)C)OC)=C/C=1N=CC(=NC=1)C1=C(C=C(C=C1)N1C=NC=C1)O)C)F PTBOVFRWTZROKC-BZYPTDMQSA-N 0.000 description 1
- SDQIBCOXZXSBDZ-MJZYEPHCSA-N 2-[5-[(Z)-[(1R,2R,5R)-6,6-difluoro-2-methoxy-8-azabicyclo[3.2.1]octan-3-ylidene]methyl]pyrazin-2-yl]-5-imidazol-1-ylphenol Chemical compound FC1([C@H]2C/C(/[C@H]([C@@H](C1)N2)OC)=C/C=1N=CC(=NC=1)C1=C(C=C(C=C1)N1C=NC=C1)O)F SDQIBCOXZXSBDZ-MJZYEPHCSA-N 0.000 description 1
- XMCPKWOIOKQYQJ-MBWAPPBDSA-N 2-[5-[(Z)-[(1R,2R,5S)-2-fluoro-7-methyl-9-azabicyclo[3.3.1]nonan-3-ylidene]methyl]pyrazin-2-yl]-5-imidazol-1-ylphenol Chemical compound F[C@H]\1[C@H]2CC(C[C@@H](C/C/1=C/C=1N=CC(=NC=1)C1=C(C=C(C=C1)N1C=NC=C1)O)N2)C XMCPKWOIOKQYQJ-MBWAPPBDSA-N 0.000 description 1
- KEAYAVFLNHSSHL-SZUFSFTISA-N 2-[5-[(Z)-[(1R,2R,5S,7R)-2-fluoro-1,5,7-trimethyl-9-azabicyclo[3.3.1]nonan-3-ylidene]methyl]pyrazin-2-yl]-5-imidazol-1-ylphenol Chemical compound F[C@H]\1[C@]2(C[C@@H](C[C@@](C/C/1=C/C=1N=CC(=NC=1)C1=C(C=C(C=C1)N1C=NC=C1)O)(N2)C)C)C KEAYAVFLNHSSHL-SZUFSFTISA-N 0.000 description 1
- ASYLBPVONQNTRV-MBTQBFQASA-N 2-[5-[(Z)-[(1R,2S,5S)-2-fluoro-1,5-dimethyl-8-azabicyclo[3.2.1]octan-3-ylidene]methyl]pyrazin-2-yl]-5-imidazol-1-ylphenol Chemical compound F[C@@H]\1[C@]2(CC[C@@](C/C/1=C/C=1N=CC(=NC=1)C1=C(C=C(C=C1)N1C=NC=C1)O)(N2)C)C ASYLBPVONQNTRV-MBTQBFQASA-N 0.000 description 1
- PBBASZDQCIJQRH-HQVWLEGGSA-N 2-[5-[(Z)-[(1R,2S,5S)-2-fluoro-8-azabicyclo[3.2.1]octan-3-ylidene]methyl]pyrazin-2-yl]-5-imidazol-1-ylphenol Chemical compound F[C@@H]\1[C@H]2CC[C@@H](C/C/1=C/C=1N=CC(=NC=1)C1=C(C=C(C=C1)N1C=NC=C1)O)N2 PBBASZDQCIJQRH-HQVWLEGGSA-N 0.000 description 1
- AATJXSYOJQAIJF-CNONJEMFSA-N 2-[5-[(Z)-[(1R,4R,5R)-7,7-difluoro-4-methoxy-1-methyl-8-azabicyclo[3.2.1]octan-3-ylidene]methyl]pyrazin-2-yl]-5-imidazol-1-ylphenol Chemical compound FC1(C[C@@H]2[C@@H](\C(\C[C@]1(N2)C)=C/C=1N=CC(=NC=1)C1=C(C=C(C=C1)N1C=NC=C1)O)OC)F AATJXSYOJQAIJF-CNONJEMFSA-N 0.000 description 1
- KZEYVMWSCRLVBT-CMZRASAVSA-N 2-[5-[(Z)-[(1S,4R,5R)-4-fluoro-1,7-dimethyl-9-azabicyclo[3.3.1]nonan-3-ylidene]methyl]pyrazin-2-yl]-5-imidazol-1-ylphenol Chemical compound F[C@@H]1\C(\C[C@@]2(CC(C[C@H]1N2)C)C)=C/C=1N=CC(=NC=1)C1=C(C=C(C=C1)N1C=NC=C1)O KZEYVMWSCRLVBT-CMZRASAVSA-N 0.000 description 1
- NWHJLSBTKXIHBP-DSMYXQPHSA-N 2-[5-[(Z)-[(1S,4S,5R)-4-fluoro-1-methyl-8-azabicyclo[3.2.1]octan-3-ylidene]methyl]pyrazin-2-yl]-5-imidazol-1-ylphenol Chemical compound F[C@H]1\C(\C[C@@]2(CC[C@H]1N2)C)=C/C=1N=CC(=NC=1)C1=C(C=C(C=C1)N1C=NC=C1)O NWHJLSBTKXIHBP-DSMYXQPHSA-N 0.000 description 1
- JWFQNAJEOIPMFW-RKNIQEAPSA-N 2-[5-[1-[(1R,2R,3R,5R)-6,6-difluoro-2-methoxy-1,5-dimethyl-8-azabicyclo[3.2.1]octan-3-yl]ethenyl]pyrazin-2-yl]-5-imidazol-1-ylphenol Chemical compound FC1([C@]2(C[C@@H]([C@H]([C@@](C1)(N2)C)OC)C(=C)C=1N=CC(=NC=1)C1=C(C=C(C=C1)N1C=NC=C1)O)C)F JWFQNAJEOIPMFW-RKNIQEAPSA-N 0.000 description 1
- JAJFLHJPIRVXMH-XWOARTFESA-N 2-[5-[1-[(1R,2R,3R,5R)-6,6-difluoro-2-methoxy-8-azabicyclo[3.2.1]octan-3-yl]ethenyl]pyrazin-2-yl]-5-imidazol-1-ylphenol Chemical compound FC1([C@H]2C[C@@H]([C@H]([C@@H](C1)N2)OC)C(=C)C=1N=CC(=NC=1)C1=C(C=C(C=C1)N1C=NC=C1)O)F JAJFLHJPIRVXMH-XWOARTFESA-N 0.000 description 1
- QQBFEYCXCKYQDD-VLCGAYIISA-N 2-[5-[1-[(1R,2R,3R,5S,7R)-2-fluoro-1,5,7-trimethyl-9-azabicyclo[3.3.1]nonan-3-yl]ethenyl]pyrazin-2-yl]-5-imidazol-1-ylphenol Chemical compound F[C@H]1[C@]2(C[C@@H](C[C@@](C[C@@H]1C(=C)C=1N=CC(=NC=1)C1=C(C=C(C=C1)N1C=NC=C1)O)(N2)C)C)C QQBFEYCXCKYQDD-VLCGAYIISA-N 0.000 description 1
- KEYZMVZHXNUGTP-PSEJGKGVSA-N 2-[5-[1-[(1R,2R,3R,5S,7R)-2-fluoro-7-methyl-9-azabicyclo[3.3.1]nonan-3-yl]ethenyl]pyrazin-2-yl]-5-imidazol-1-ylphenol Chemical compound F[C@H]1[C@H]2C[C@@H](C[C@@H](C[C@@H]1C(=C)C=1N=CC(=NC=1)C1=C(C=C(C=C1)N1C=NC=C1)O)N2)C KEYZMVZHXNUGTP-PSEJGKGVSA-N 0.000 description 1
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Applications Claiming Priority (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201962802059P | 2019-02-06 | 2019-02-06 | |
| US201962802075P | 2019-02-06 | 2019-02-06 | |
| US201962802071P | 2019-02-06 | 2019-02-06 | |
| US201962802072P | 2019-02-06 | 2019-02-06 | |
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| US201962802061P | 2019-02-06 | 2019-02-06 | |
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Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3728228A1 (en) | 2017-12-22 | 2020-10-28 | Ravenna Pharmaceuticals, Inc. | Aminopyridine derivatives as phosphatidylinositol phosphate kinase inhibitors |
| TWI721623B (zh) | 2018-10-31 | 2021-03-11 | 美商基利科學股份有限公司 | 經取代之6-氮雜苯并咪唑化合物 |
| TW202136261A (zh) | 2018-10-31 | 2021-10-01 | 美商基利科學股份有限公司 | 經取代之6-氮雜苯并咪唑化合物 |
| WO2020163405A1 (en) | 2019-02-05 | 2020-08-13 | Skyhawk Therapeutics, Inc. | Methods and compositions for modulating splicing |
| JP7551629B2 (ja) | 2019-02-05 | 2024-09-17 | スカイホーク・セラピューティクス・インコーポレーテッド | スプライシングを調節するための方法および組成物 |
| JP7603595B2 (ja) | 2019-02-06 | 2024-12-20 | スカイホーク・セラピューティクス・インコーポレーテッド | スプライシングを調節するための方法および組成物 |
| JP7603594B2 (ja) | 2019-02-06 | 2024-12-20 | スカイホーク・セラピューティクス・インコーポレーテッド | スプライシングを調節するための方法および組成物 |
| US11453681B2 (en) | 2019-05-23 | 2022-09-27 | Gilead Sciences, Inc. | Substituted eneoxindoles and uses thereof |
| TW202112767A (zh) | 2019-06-17 | 2021-04-01 | 美商佩特拉製藥公司 | 作為磷脂酸肌醇磷酸激酶抑制劑之胺基吡啶衍生物 |
| TW202131920A (zh) | 2019-11-01 | 2021-09-01 | 瑞士商諾華公司 | 剪接調節子用於減慢杭丁頓氏舞蹈症進展的治療之用途 |
| CA3182912A1 (en) | 2020-05-13 | 2021-11-18 | Chdi Foundation, Inc. | Htt modulators for treating huntington's disease |
| IL301964A (en) | 2020-10-08 | 2023-06-01 | Redona Therapeutics Inc | History of benzo[H]quinazoline-4-amine and thiano[2,3-H]quinazoline-4-amine for cancer treatment |
| MX2024005933A (es) | 2021-11-17 | 2024-08-06 | Chdi Foundation Inc | Moduladores de htt pata tratar la enfermedad de huntington. |
| JP2025183938A (ja) | 2024-06-05 | 2025-12-17 | 住友化学株式会社 | レジスト組成物、レジストパターンの製造方法及びめっき造形物の製造方法 |
Family Cites Families (145)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4873192A (en) | 1987-02-17 | 1989-10-10 | The United States Of America As Represented By The Department Of Health And Human Services | Process for site specific mutagenesis without phenotypic selection |
| NZ227684A (en) | 1988-01-30 | 1991-07-26 | Merck Sharp & Dohme | Pyrazine, pyridazine, and pyrimidine derivatives and pharmaceutical compositions |
| GB9005737D0 (en) | 1990-03-14 | 1990-05-09 | Beecham Group Plc | Novel compounds |
| FR2676444B1 (fr) | 1991-05-16 | 1995-03-10 | Sanofi Elf | Nouveaux derives d'amino-3 pyridazines actifs sur le systeme nerveux central, procede de preparation et compositions pharmaceutiques en contenant. |
| EP1191097A1 (en) | 2000-09-21 | 2002-03-27 | Leids Universitair Medisch Centrum | Induction of exon skipping in eukaryotic cells |
| ATE420351T1 (de) | 2001-08-31 | 2009-01-15 | Gen Probe Inc | Sonden mit affinitätsverschiebung zur quantifizierung von analytenpolynukleotiden |
| US6992087B2 (en) | 2001-11-21 | 2006-01-31 | Pfizer Inc | Substituted aryl 1,4-pyrazine derivatives |
| US7135484B2 (en) | 2002-08-14 | 2006-11-14 | Abbott Laboratories | Azabicyclic compounds are central nervous system active agents |
| US7220741B2 (en) | 2002-09-30 | 2007-05-22 | Neurosearch A/S | 1,4-diazabicycloalkane derivatives, their preparation and use |
| US8014953B2 (en) | 2003-08-08 | 2011-09-06 | The Regents Of The University Of California | RNA surveillance among curated proteins |
| US7399765B2 (en) | 2003-09-19 | 2008-07-15 | Abbott Laboratories | Substituted diazabicycloalkane derivatives |
| US7309699B2 (en) | 2003-12-22 | 2007-12-18 | Abbott Laboratories | 3-Quinuclidinyl amino-substituted biaryl derivatives |
| US7160876B2 (en) | 2003-12-22 | 2007-01-09 | Abbott Laboratories | Fused bicycloheterocycle substituted quinuclidine derivatives |
| US7655657B2 (en) | 2003-12-22 | 2010-02-02 | Abbott Laboratories | Fused bicycloheterocycle substituted quinuclidine derivatives |
| US7309487B2 (en) | 2004-02-09 | 2007-12-18 | George Inana | Methods and compositions for detecting and treating retinal diseases |
| PE20060437A1 (es) | 2004-06-18 | 2006-06-08 | Novartis Ag | COMPUESTOS AZA-BICICLONONANOS COMO LIGANDOS COLINERGICOS DE nAChR |
| GB0415746D0 (en) | 2004-07-14 | 2004-08-18 | Novartis Ag | Organic compounds |
| US7879882B2 (en) | 2004-10-07 | 2011-02-01 | Merck Sharp & Dohme Corp. | Thiazolyl mglur5 antagonists and methods for their use |
| EA012181B1 (ru) | 2004-10-18 | 2009-08-28 | Амген, Инк. | Соединения тиадиазола и их применение |
| US7838657B2 (en) | 2004-12-03 | 2010-11-23 | University Of Massachusetts | Spinal muscular atrophy (SMA) treatment via targeting of SMN2 splice site inhibitory sequences |
| DE602006010991D1 (de) | 2005-01-26 | 2010-01-21 | Schering Corp | 3-(indazol-5-yl)-(1,2,4)triazinderivate und verwandte verbindungen als proteinkinaseinhibitoren zur behandlung von krebs |
| CA2606288A1 (en) | 2005-04-18 | 2006-10-26 | Neurogen Corporation | Subtituted heteroaryl cb1 antagonists |
| US7598052B2 (en) | 2005-10-11 | 2009-10-06 | The Regents Of The University Of Michigan | Expression profile of thyroid cancer |
| US8603457B2 (en) | 2005-12-02 | 2013-12-10 | University Of Rochester | Nonsense suppression and genetic codon alteration by targeted modification |
| US7834178B2 (en) | 2006-03-01 | 2010-11-16 | Bristol-Myers Squibb Company | Triazine 11-beta hydroxysteroid dehydrogenase type 1 inhibitors |
| UA92083C2 (ru) | 2006-05-19 | 2010-09-27 | Эбботт Леборетриз | Азабициклические алкановые производные, замещенные конденсированным бициклогетероциклом |
| US8158619B2 (en) | 2006-05-30 | 2012-04-17 | Neurosearch A/S | 1,4-diaza-bicyclo[3.2.2]nonyl oxadiazolyl compounds and their medical use |
| US8314119B2 (en) | 2006-11-06 | 2012-11-20 | Abbvie Inc. | Azaadamantane derivatives and methods of use |
| US8343941B2 (en) | 2007-03-30 | 2013-01-01 | Rutgers, The State University Of New Jersey | Compositions and methods for gene silencing |
| US8283116B1 (en) | 2007-06-22 | 2012-10-09 | Ptc Therapeutics, Inc. | Methods of screening for compounds for treating spinal muscular atrophy using SMN mRNA translation regulation |
| DE102007032507A1 (de) | 2007-07-12 | 2009-04-02 | Merck Patent Gmbh | Pyridazinonderivate |
| AU2008317566B2 (en) | 2007-10-26 | 2014-05-01 | Academisch Ziekenhuis Leiden | Means and methods for counteracting muscle disorders |
| BRPI0820418A2 (pt) | 2007-11-21 | 2015-05-19 | Abbott Lab | "derivados de alcano azabicíclico substituído com biarila como moduladores da atividade do receptor nicotínico de acetilcolina" |
| WO2009116353A1 (ja) | 2008-03-18 | 2009-09-24 | コニカミノルタホールディングス株式会社 | 電気化学的表示素子 |
| WO2009151546A2 (en) | 2008-05-27 | 2009-12-17 | Ptc Therapeutics, Inc. | Methods for treating spinal muscular atrophy |
| US8133724B2 (en) | 2008-09-17 | 2012-03-13 | University Of Maryland, Baltimore | Human androgen receptor alternative splice variants as biomarkers and therapeutic targets |
| CA2740193A1 (en) | 2008-12-23 | 2010-07-01 | Abbott Laboratories | Anti-viral compounds |
| EP2408919B1 (en) | 2009-03-16 | 2017-10-18 | CuRNA, Inc. | Treatment of nuclear factor (erythroid-derived 2)-like 2 (nrf2) related diseases by inhibition of natural antisense transcript to nrf2 |
| US20120149756A1 (en) | 2009-04-10 | 2012-06-14 | Associatin Institut de Myologie | Tricyclo-dna antisense oligonucleotides, compositions, and methods for the treatment of disease |
| PT3305302T (pt) | 2009-06-17 | 2018-12-14 | Biogen Ma Inc | Composições e métodos de modulação de excisões de smn2 em um sujeito |
| JO3250B1 (ar) | 2009-09-22 | 2018-09-16 | Novartis Ag | إستعمال منشطات مستقبل نيكوتينيك أسيتيل كولين ألفا 7 |
| EP2305679A1 (en) | 2009-09-28 | 2011-04-06 | GenKyoTex SA | Pyrazoline dione derivatives as nadph oxidase inhibitors |
| AR079724A1 (es) | 2010-01-20 | 2012-02-15 | Abbott Lab | Metodos para el tratamiento del dolor |
| SI2531492T1 (sl) | 2010-02-05 | 2016-08-31 | Heptares Therapeutics Limited | Derivati 1,2,4-triazin-4-amina |
| AR081626A1 (es) | 2010-04-23 | 2012-10-10 | Cytokinetics Inc | Compuestos amino-piridazinicos, composiciones farmaceuticas que los contienen y uso de los mismos para tratar trastornos musculares cardiacos y esqueleticos |
| US9133123B2 (en) | 2010-04-23 | 2015-09-15 | Cytokinetics, Inc. | Certain amino-pyridines and amino-triazines, compositions thereof, and methods for their use |
| AR081331A1 (es) | 2010-04-23 | 2012-08-08 | Cytokinetics Inc | Amino- pirimidinas composiciones de las mismas y metodos para el uso de los mismos |
| US8802642B2 (en) | 2010-04-28 | 2014-08-12 | Iowa State University Research Foundation, Inc. | Spinal muscular atrophy treatment via targeting SMN2 catalytic core |
| JP6069661B2 (ja) | 2010-06-24 | 2017-02-01 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | 種々のアミロイドβペプチドアロフォームレベルの調節における組成物及びその使用 |
| BR112013002112B1 (pt) | 2010-07-29 | 2021-04-06 | Rigel Pharmaceuticals, Inc. | Composto, composição farmacêutica, e, uso de um composto, ou de um respectivo sal farmaceuticamente aceitável, ou de uma composição |
| CN103732258A (zh) | 2011-03-14 | 2014-04-16 | Nse产品公司 | 用于促进细胞纯化的口服制剂 |
| WO2012129562A2 (en) | 2011-03-24 | 2012-09-27 | The Scripps Research Institute | Compounds and methods for inducing chondrogenesis |
| US9447075B2 (en) | 2011-08-02 | 2016-09-20 | The Brigham And Women's Hospital, Inc. | Pyridazine derivatives as EAAT2 activators |
| WO2013063458A2 (en) | 2011-10-27 | 2013-05-02 | Mayo Foundation For Medical Education And Research | Inhibiting g protein coupled receptor 6 kinase polypeptides |
| MX352861B (es) | 2011-12-30 | 2017-12-13 | Ptc Therapeutics Inc | Compuestos para tratar la atrofia muscular espinal. |
| MX357834B (es) | 2012-01-26 | 2018-07-26 | Ptc Therapeutics Inc | Compuestos de tipo isocumarina sustituidos para tratar la atrofia muscular espinal. |
| WO2013117693A1 (en) | 2012-02-10 | 2013-08-15 | Glaxosmithkline Intellectual Property Development Limited | Pde4 inhibitor for treating huntington's disease |
| EP2812004B1 (en) | 2012-02-10 | 2018-06-27 | PTC Therapeutics, Inc. | Compounds for treating spinal muscular atrophy |
| CA2865957C (en) | 2012-03-01 | 2020-02-11 | F. Hoffmann-La Roche Ag | Compounds for treating spinal muscular atrophy |
| CA2868026C (en) | 2012-03-23 | 2021-02-16 | Ptc Therapeutics, Inc. | Compounds for treating spinal muscular atrophy |
| US8729263B2 (en) * | 2012-08-13 | 2014-05-20 | Novartis Ag | 1,4-disubstituted pyridazine analogs there of and methods for treating SMN-deficiency-related conditions |
| AU2013204200B2 (en) | 2012-10-11 | 2016-10-20 | Brandeis University | Treatment of amyotrophic lateral sclerosis |
| ES2762326T5 (es) | 2012-10-15 | 2023-04-27 | Ionis Pharmaceuticals Inc | Métodos para modular la expresión de C9ORF72 |
| CN105263492B (zh) | 2013-01-15 | 2018-04-10 | 诺华有限公司 | α7烟碱型乙酰胆碱受体激动剂在治疗发作性睡病中的应用 |
| EP2945633B1 (en) | 2013-01-15 | 2021-06-30 | Novartis AG | Use of alpha 7 nicotinic acetylcholine receptor agonists |
| BR112015016992A8 (pt) | 2013-01-15 | 2018-01-23 | Novartis Ag | uso de agonistas do receptor alfa 7 nicotínico de acetilcolina |
| US9040712B2 (en) | 2013-01-23 | 2015-05-26 | Novartis Ag | Thiadiazole analogs thereof and methods for treating SMN-deficiency-related-conditions |
| CA2913785C (en) | 2013-06-25 | 2021-08-31 | F. Hoffmann-La Roche Ag | Compounds for treating spinal muscular atrophy |
| EP4105208A1 (en) | 2013-07-31 | 2022-12-21 | Novartis AG | 1,4-disubstituted pyridazine derivatives and their use for treating smn-deficiency-related conditions |
| EP3035935B1 (en) | 2013-08-19 | 2020-03-11 | F. Hoffmann-La Roche AG | Compounds for use in the prophylaxis and treatment of cancer |
| US20230009804A1 (en) | 2013-08-23 | 2023-01-12 | Ateb, Inc. | Machine-learning techniques for generating entity instructions |
| WO2015031036A1 (en) | 2013-08-26 | 2015-03-05 | Purdue Pharma L.P. | Azaspiro[4.5] decane derivatives and use thereof |
| EP3052654A4 (en) | 2013-09-30 | 2017-05-03 | The Regents of the University of California | Identification of structurally similar small molecules that enhance therapeutic exon skipping |
| US11162096B2 (en) | 2013-10-14 | 2021-11-02 | Ionis Pharmaceuticals, Inc | Methods for modulating expression of C9ORF72 antisense transcript |
| JP6643545B2 (ja) | 2014-03-14 | 2020-02-12 | ラクオリア創薬株式会社 | Ｔｒｐｍ８拮抗剤としてのアザスピロ誘導体 |
| WO2015143245A1 (en) | 2014-03-19 | 2015-09-24 | Isis Pharmaceuticals, Inc. | Methods for modulating ataxin 2 expression |
| WO2015190921A2 (en) | 2014-06-10 | 2015-12-17 | Erasmus University Medical Center Rotterdam | Methods for characterizing alternatively or aberrantly spliced mrna isoforms |
| GB201410693D0 (en) | 2014-06-16 | 2014-07-30 | Univ Southampton | Splicing modulation |
| WO2016037039A1 (en) | 2014-09-04 | 2016-03-10 | Rutgers, The State University Of New Jersey | Compositions for increasing survival of motor neuron protein (smn) levels in target cells and methods of use thereof for the treatment of spinal muscular atrophy |
| WO2016064895A1 (en) | 2014-10-20 | 2016-04-28 | The Brigham And Women's Hospital, Inc. | Targeting apolipoprotein e (apoe) in neurologic disease |
| US10053697B1 (en) | 2015-01-09 | 2018-08-21 | The Board Of Trustees Of The Leland Stanford Junior University | Programmable alternative splicing devices and uses thereof |
| BR112017015273A2 (pt) | 2015-01-20 | 2018-01-09 | Merial Inc. | compostos e composições antihelmínticos e método de utilizações dos mesmos |
| EP3053577A1 (en) | 2015-02-09 | 2016-08-10 | F. Hoffmann-La Roche AG | Compounds for the treatment of cancer |
| EP3256126B1 (en) | 2015-02-09 | 2024-03-27 | F. Hoffmann-La Roche AG | Compounds for the treatment of cancer |
| US10668171B2 (en) | 2015-05-30 | 2020-06-02 | Ptc Therapeutics, Inc. | Methods for modulating RNA splicing |
| AR105392A1 (es) | 2015-07-20 | 2017-09-27 | Genzyme Corp | Inhibidores del receptor del factor estimulador de colonias 1 (csf-1r) |
| WO2017041036A1 (en) | 2015-09-02 | 2017-03-09 | Pathways Bioscience, Llc | Compositions and methods for treatment or prevention of oral mucositis |
| US10358427B2 (en) | 2015-09-24 | 2019-07-23 | Glaxosmithkline Intellectual Property Development Limited | Modulators of indoleamine 2,3-dioxygenase |
| WO2017062751A1 (en) | 2015-10-08 | 2017-04-13 | The Regents Of The University Of California | Compounds and methods for promoting stress resistance |
| EP3359685B1 (en) | 2015-10-09 | 2026-01-28 | University Of Southampton | Modulation of gene expression for deregulated protein expression |
| EA036399B1 (ru) | 2015-11-12 | 2020-11-06 | Ф. Хоффманн-Ля Рош Аг | Композиции для лечения спинальной мышечной атрофии |
| WO2017100276A1 (en) | 2015-12-08 | 2017-06-15 | The Arizona Board Of Regents On Behalf Of The University Of Arizona | Compositions and methods for treatment, amelioration, and prevention of diabetes-related skin ulcers |
| EA201800367A1 (ru) * | 2015-12-10 | 2019-02-28 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | Способы лечения болезни хантингтона |
| US11096956B2 (en) | 2015-12-14 | 2021-08-24 | Stoke Therapeutics, Inc. | Antisense oligomers and uses thereof |
| JP2019502753A (ja) | 2015-12-23 | 2019-01-31 | ムーンショット ファーマ エルエルシー | ナンセンス変異依存ｍＲＮＡ分解機構の抑制による免疫応答の誘導法 |
| WO2017123991A1 (en) | 2016-01-15 | 2017-07-20 | The Brigham And Women's Hospital, Inc. | Pyridazine derivatives as eaat2 activators |
| MX2018009325A (es) | 2016-02-01 | 2019-05-15 | Arrakis Therapeutics Inc | Compuestos y metodos para tratar enfermedades mediadas por el acido ribonucleico (arn). |
| MX2018010109A (es) | 2016-02-23 | 2018-12-17 | Univ Indiana Res & Tech Corp | Terapias de combinacion para tratamiento de atrofia muscular espinal. |
| CN109069870B (zh) | 2016-02-24 | 2022-04-29 | 洛克菲勒大学 | 基于胚胎细胞的用于亨廷顿氏病的治疗候选物筛选系统、模型及它们的应用 |
| US11066456B2 (en) | 2016-02-25 | 2021-07-20 | Washington University | Compositions comprising TREM2 and methods of use thereof |
| US20170268066A1 (en) | 2016-03-15 | 2017-09-21 | Chalmers Ventures Ab | Cancer biomarkers |
| JP6923551B2 (ja) | 2016-03-29 | 2021-08-18 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | ピルバートデヒドロゲナーゼキナーゼのインヒビターとしてのｎ１−（３，３，３−トリフルオロ−２−ヒドロキシ−２−メチルプロピオニル）−ピペリジン誘導体 |
| US10940161B2 (en) | 2016-04-04 | 2021-03-09 | University Of Florida Research Foundation, Incorporated | Manipulation of EIF3 to modulate repeat associated non-ATG (RAN) translation |
| US10577360B2 (en) | 2016-04-12 | 2020-03-03 | Esteve Pharmaceuticals, S.A. | Arylamide derivatives having multimodal activity against pain |
| AU2017283546C1 (en) | 2016-06-13 | 2020-11-19 | Scholar Rock, Inc. | Use of myostatin inhibitors and combination therapies |
| SG11201811643TA (en) | 2016-07-01 | 2019-01-30 | Arrakis Therapeutics Inc | Compounds and methods for modulating rna function |
| JP2019535789A (ja) | 2016-11-28 | 2019-12-12 | ピーティーシー セラピューティクス，インコーポレーテッド | Ｒｎａスプライシングを調節する方法 |
| WO2018151326A1 (ja) | 2017-02-20 | 2018-08-23 | 国立大学法人京都大学 | スプライシング異常に起因する遺伝性疾病のための医薬組成物及び治療方法 |
| US11715549B2 (en) | 2017-05-01 | 2023-08-01 | Thomas Jefferson University | Systems-level analysis of 32 TCGA cancers reveals disease-dependent tRNA fragmentation patterns and very selective associations with messenger RNAs and repeat elements |
| JP2020523365A (ja) | 2017-06-14 | 2020-08-06 | ピーティーシー セラピューティクス，インコーポレーテッド | Ｒｎａスプライシングを改変する方法 |
| CN111182898B (zh) | 2017-06-28 | 2024-04-16 | Ptc医疗公司 | 用于治疗亨廷顿氏病的方法 |
| MX2019015580A (es) | 2017-06-28 | 2020-07-28 | Ptc Therapeutics Inc | Metodos para tratar la enfermedad de huntington. |
| JP7312749B2 (ja) * | 2017-08-04 | 2023-07-21 | スカイホーク・セラピューティクス・インコーポレーテッド | スプライシングをモジュレートする方法および組成物 |
| EP3686196B1 (en) | 2017-09-20 | 2024-06-12 | Hangzhou Innogate Pharma Co., Ltd. | Polycyclic compound acting as ido inhibitor and/or ido-hdac dual inhibitor |
| MX2020003579A (es) | 2017-10-12 | 2020-07-22 | Revolution Medicines Inc | Compuestos de piridina, pirazina, y triazina como inhibidores de shp2 alostericos. |
| CA3079727A1 (en) | 2017-10-24 | 2019-05-02 | Sangamo Therapeutics, Inc. | Methods and compositions for the treatment of rare diseases |
| EP3479845A1 (en) | 2017-11-06 | 2019-05-08 | Stalicla S.A. | Challenge test for diagnosing subtype of autism spectrum disease |
| WO2019094694A1 (en) | 2017-11-10 | 2019-05-16 | University Of Massachusetts | Compositions and methods for the treatment of expanded repeat-associated disorders |
| EA202092001A1 (ru) | 2018-03-27 | 2021-01-29 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | Соединения для лечения болезни гентингтона |
| JP2021521200A (ja) | 2018-04-10 | 2021-08-26 | スカイホーク・セラピューティクス・インコーポレーテッド | 癌の処置のための化合物 |
| EP3814360B8 (en) | 2018-06-27 | 2024-11-06 | PTC Therapeutics, Inc. | Heteroaryl compounds for treating huntington's disease |
| HRP20240935T1 (hr) | 2018-06-27 | 2024-11-22 | Ptc Therapeutics, Inc. | Heterociklični i heteroaril spojevi za liječenje huntingtonove bolesti |
| WO2020005877A1 (en) | 2018-06-27 | 2020-01-02 | Ptc Therapeutics, Inc. | Heteroaryl compounds for treating huntington's disease |
| US11987568B2 (en) | 2018-08-03 | 2024-05-21 | H. Lee Moffitt Cancer Center And Research Institute, Inc. | Allosteric inhibitor of WEE1 kinase |
| TW202028183A (zh) | 2018-10-10 | 2020-08-01 | 大陸商江蘇豪森藥業集團有限公司 | 含氮雜芳類衍生物調節劑、其製備方法和應用 |
| EP3920910A4 (en) | 2019-02-04 | 2022-11-09 | Skyhawk Therapeutics, Inc. | METHODS AND COMPOSITIONS FOR MODULATION OF SPLICING |
| JP2022519637A (ja) | 2019-02-04 | 2022-03-24 | スカイホーク・セラピューティクス・インコーポレーテッド | スプライシングを調節するための方法および組成物 |
| WO2020163382A1 (en) | 2019-02-04 | 2020-08-13 | Skyhawk Therapeutics, Inc. | Methods and compositions for modulating splicing |
| KR102925387B1 (ko) | 2019-02-04 | 2026-02-10 | 스카이호크 테라퓨틱스, 인코포레이티드 | 스플라이싱을 조절하는 방법 및 조성물 |
| WO2020163405A1 (en) | 2019-02-05 | 2020-08-13 | Skyhawk Therapeutics, Inc. | Methods and compositions for modulating splicing |
| WO2020163401A1 (en) | 2019-02-05 | 2020-08-13 | Skyhawk Therapeutics, Inc. | Methods and compositions for modulating splicing |
| US20230008867A1 (en) | 2019-02-05 | 2023-01-12 | Skyhawk Therapeutics, Inc. | Methods and compositions for modulating splicing |
| WO2020163406A1 (en) | 2019-02-05 | 2020-08-13 | Skyhawk Therapeutics, Inc. | Methods and compositions for modulating splicing |
| JP2022519311A (ja) | 2019-02-05 | 2022-03-22 | スカイホーク・セラピューティクス・インコーポレーテッド | スプライシングを調節するための方法および組成物 |
| JP7551629B2 (ja) | 2019-02-05 | 2024-09-17 | スカイホーク・セラピューティクス・インコーポレーテッド | スプライシングを調節するための方法および組成物 |
| JP7603594B2 (ja) | 2019-02-06 | 2024-12-20 | スカイホーク・セラピューティクス・インコーポレーテッド | スプライシングを調節するための方法および組成物 |
| JP7603595B2 (ja) | 2019-02-06 | 2024-12-20 | スカイホーク・セラピューティクス・インコーポレーテッド | スプライシングを調節するための方法および組成物 |
| WO2020190793A1 (en) | 2019-03-15 | 2020-09-24 | Skyhawk Therapeutics, Inc. | Compositions and methods for correction of aberrant splicing |
| US11129829B2 (en) | 2019-06-17 | 2021-09-28 | Skyhawk Therapeutics, Inc. | Methods for modulating splicing |
| WO2021071984A1 (en) | 2019-10-08 | 2021-04-15 | Skyhawk Therapeutics, Inc. | Compounds for modulating splicing |
| WO2021174176A1 (en) | 2020-02-28 | 2021-09-02 | Remix Therapeutics Inc. | Pyridazine dervatives for modulating nucleic acid splicing |
| WO2022031998A2 (en) | 2020-08-05 | 2022-02-10 | Skyhawk Therapeutics, Inc. | Process for the preparation of intermediates useful in the preparation of compounds that modulate splicing |
| MX2023001558A (es) | 2020-08-05 | 2023-04-26 | Skyhawk Therapeutics Inc | Composiciones para modular el corte y empalme. |
| WO2022060951A1 (en) | 2020-09-16 | 2022-03-24 | Skyhawk Therapeutics, Inc. | Compositions for modulating splicing |
| US20240368163A1 (en) | 2021-08-30 | 2024-11-07 | Remix Therapeutics Inc. | Compounds and methods for modulating splicing |
-
2020
- 2020-02-06 JP JP2021546239A patent/JP7603595B2/ja active Active
- 2020-02-06 WO PCT/US2020/016897 patent/WO2020163544A1/en not_active Ceased
- 2020-02-06 CN CN202411652884.9A patent/CN119528905A/zh active Pending
- 2020-02-06 KR KR1020217027887A patent/KR102925385B1/ko active Active
- 2020-02-06 CN CN202080027261.6A patent/CN113677344A/zh active Pending
- 2020-02-06 EP EP20752604.7A patent/EP3920928A4/en active Pending
-
2021
- 2021-07-29 US US17/388,100 patent/US11964971B2/en active Active
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2024
- 2024-02-27 US US18/588,513 patent/US20250101016A1/en not_active Abandoned
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