JP2019508467A5 - - Google Patents
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- Publication number
- JP2019508467A5 JP2019508467A5 JP2018548744A JP2018548744A JP2019508467A5 JP 2019508467 A5 JP2019508467 A5 JP 2019508467A5 JP 2018548744 A JP2018548744 A JP 2018548744A JP 2018548744 A JP2018548744 A JP 2018548744A JP 2019508467 A5 JP2019508467 A5 JP 2019508467A5
- Authority
- JP
- Japan
- Prior art keywords
- carbonitrile
- cyano
- dihydro
- pyrrolo
- isoindoline
- 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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- -1 cyano, amino Chemical group 0.000 claims 32
- 150000001875 compounds Chemical class 0.000 claims 18
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 229910052736 halogen Inorganic materials 0.000 claims 12
- 150000002367 halogens Chemical class 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 11
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- 230000007812 deficiency Effects 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000004043 oxo group Chemical group O=* 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 206010028980 Neoplasm Diseases 0.000 claims 5
- 125000004450 alkenylene group Chemical group 0.000 claims 5
- 201000011510 cancer Diseases 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 150000003573 thiols Chemical class 0.000 claims 5
- JIKNSBXBRVGCNU-UHFFFAOYSA-N 1,3-dihydroisoindole-2-carbonitrile Chemical compound C1=CC=C2CN(C#N)CC2=C1 JIKNSBXBRVGCNU-UHFFFAOYSA-N 0.000 claims 4
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 4
- 125000003368 amide group Chemical group 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 4
- 208000011580 syndromic disease Diseases 0.000 claims 4
- 208000006136 Leigh Disease Diseases 0.000 claims 3
- 208000017507 Leigh syndrome Diseases 0.000 claims 3
- 201000002169 Mitochondrial myopathy Diseases 0.000 claims 3
- 208000008955 Mucolipidoses Diseases 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- 208000014644 Brain disease Diseases 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 206010058892 Carnitine deficiency Diseases 0.000 claims 2
- 201000000915 Chronic Progressive External Ophthalmoplegia Diseases 0.000 claims 2
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 2
- 206010010904 Convulsion Diseases 0.000 claims 2
- 208000032274 Encephalopathy Diseases 0.000 claims 2
- 208000032087 Hereditary Leber Optic Atrophy Diseases 0.000 claims 2
- 201000000639 Leber hereditary optic neuropathy Diseases 0.000 claims 2
- 108010027062 Long-Chain Acyl-CoA Dehydrogenase Proteins 0.000 claims 2
- 102000018653 Long-Chain Acyl-CoA Dehydrogenase Human genes 0.000 claims 2
- 108700006159 Long-chain acyl-CoA dehydrogenase deficiency Proteins 0.000 claims 2
- 206010058799 Mitochondrial encephalomyopathy Diseases 0.000 claims 2
- 206010072930 Mucolipidosis type IV Diseases 0.000 claims 2
- 208000001769 Multiple Acyl Coenzyme A Dehydrogenase Deficiency Diseases 0.000 claims 2
- 208000000149 Multiple Sulfatase Deficiency Disease Diseases 0.000 claims 2
- 208000035032 Multiple sulfatase deficiency Diseases 0.000 claims 2
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims 2
- BENWJWZDAMYPBU-UHFFFAOYSA-N N-(2-cyano-7-phenyl-1,3-dihydroisoindol-5-yl)piperidine-4-carboxamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)C1CCNCC1)C1=CC=CC=C1 BENWJWZDAMYPBU-UHFFFAOYSA-N 0.000 claims 2
- 206010039491 Sarcoma Diseases 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- UCOHKZKRNWNULS-UHFFFAOYSA-N aminocyanamide Chemical compound NNC#N UCOHKZKRNWNULS-UHFFFAOYSA-N 0.000 claims 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 208000023692 inborn mitochondrial myopathy Diseases 0.000 claims 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 208000006443 lactic acidosis Diseases 0.000 claims 2
- 208000004687 long chain acyl-CoA dehydrogenase deficiency Diseases 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- ZIEWSZYVEDTXGH-UHFFFAOYSA-N pyrimidine-4-carbonitrile Chemical compound N#CC1=CC=NC=N1 ZIEWSZYVEDTXGH-UHFFFAOYSA-N 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- 208000016505 systemic primary carnitine deficiency disease Diseases 0.000 claims 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- VTWQLTIKQINFDK-MRXNPFEDSA-N (3R)-N-(2-cyano-7-pyridin-3-yl-1,3-dihydroisoindol-5-yl)-1-methylpiperidine-3-carboxamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)[C@H]1CN(CCC1)C)C=1C=NC=CC=1 VTWQLTIKQINFDK-MRXNPFEDSA-N 0.000 claims 1
- QNVJQEXVANWZAM-QGZVFWFLSA-N (3R)-N-[2-cyano-7-(2-methyl-1,3-benzoxazol-6-yl)-1,3-dihydroisoindol-5-yl]-1-methylpiperidine-3-carboxamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)[C@H]1CN(CCC1)C)C1=CC2=C(N=C(O2)C)C=C1 QNVJQEXVANWZAM-QGZVFWFLSA-N 0.000 claims 1
- MWRRWTYALQDOLU-GOSISDBHSA-N (3R)-N-[2-cyano-7-(3-cyanophenyl)-1,3-dihydroisoindol-5-yl]-1-methylpiperidine-3-carboxamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)[C@H]1CN(CCC1)C)C1=CC(=CC=C1)C#N MWRRWTYALQDOLU-GOSISDBHSA-N 0.000 claims 1
- IUOJRCLOBYQXJQ-MRXNPFEDSA-N (3R)-N-[2-cyano-7-(3-fluorophenyl)-1,3-dihydroisoindol-5-yl]-1-methylpiperidine-3-carboxamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)[C@H]1CN(CCC1)C)C1=CC(=CC=C1)F IUOJRCLOBYQXJQ-MRXNPFEDSA-N 0.000 claims 1
- UMSLMEJNFDSWFC-MRXNPFEDSA-N (3R)-N-[2-cyano-7-(4-fluorophenyl)-1,3-dihydroisoindol-5-yl]-1-methylpiperidine-3-carboxamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)[C@H]1CN(CCC1)C)C1=CC=C(C=C1)F UMSLMEJNFDSWFC-MRXNPFEDSA-N 0.000 claims 1
- HVFCCVCLKXYNQZ-GOSISDBHSA-N (3R)-N-[2-cyano-7-[3-(methylcarbamoyl)phenyl]-1,3-dihydroisoindol-5-yl]-1-methylpiperidine-3-carboxamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)[C@H]1CN(CCC1)C)C1=CC(=CC=C1)C(NC)=O HVFCCVCLKXYNQZ-GOSISDBHSA-N 0.000 claims 1
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 1
- PTNLNSCPXFNOAU-UHFFFAOYSA-N 1-(3-methoxyphenyl)-4-(1-methylpyrazol-4-yl)-5,7-dihydropyrrolo[3,4-d]pyridazine-6-carbonitrile Chemical compound COC=1C=C(C=CC=1)C1=NN=C(C2=C1CN(C2)C#N)C=1C=NN(C=1)C PTNLNSCPXFNOAU-UHFFFAOYSA-N 0.000 claims 1
- KPQWRGUCJMJHLM-UHFFFAOYSA-N 1-(6-cyano-2-phenyl-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl)-N-methylpyrrolidine-2-carboxamide Chemical compound C(#N)N1CC=2N=C(N=C(C=2C1)N1C(CCC1)C(=O)NC)C1=CC=CC=C1 KPQWRGUCJMJHLM-UHFFFAOYSA-N 0.000 claims 1
- IVRVOJDKRPMXBX-UHFFFAOYSA-N 1-[[2-cyano-7-(2,4-dicyanophenyl)-1,3-dihydroisoindol-5-yl]methyl]-3-methylurea Chemical compound CNC(=O)NCC1=CC2=C(CN(C2)C#N)C(=C1)C1=C(C=C(C=C1)C#N)C#N IVRVOJDKRPMXBX-UHFFFAOYSA-N 0.000 claims 1
- QKCRRJHDFZSNLB-UHFFFAOYSA-N 1-[[2-cyano-7-(2-cyanophenyl)-1,3-dihydroisoindol-5-yl]methyl]-3-methylurea Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)CNC(=O)NC)C1=C(C=CC=C1)C#N QKCRRJHDFZSNLB-UHFFFAOYSA-N 0.000 claims 1
- OGKFZDXPRXRABQ-UHFFFAOYSA-N 1-[[2-cyano-7-(4-cyanophenyl)-1,3-dihydroisoindol-5-yl]methyl]-3-methylurea Chemical compound CNC(=O)NCC1=CC2=C(CN(C2)C#N)C(=C1)C1=CC=C(C=C1)C#N OGKFZDXPRXRABQ-UHFFFAOYSA-N 0.000 claims 1
- HIKMUOHWJUJPPO-UHFFFAOYSA-N 2-(2,3-dihydroxypropylamino)-4-(4-fluorophenyl)-5,7-dihydropyrrolo[3,4-b]pyridine-6-carbonitrile Chemical compound OC(CNC1=CC(=C2C(=N1)CN(C2)C#N)C1=CC=C(C=C1)F)CO HIKMUOHWJUJPPO-UHFFFAOYSA-N 0.000 claims 1
- CFMBZDQXDHDYGV-UHFFFAOYSA-N 2-(2,6-dicyano-1,3-dihydroisoindol-4-yl)-5-fluorobenzamide Chemical compound C(#N)N1CC2=CC(=CC(=C2C1)C1=C(C(=O)N)C=C(C=C1)F)C#N CFMBZDQXDHDYGV-UHFFFAOYSA-N 0.000 claims 1
- FUEVEDMMGBYHSU-UHFFFAOYSA-N 2-(2-cyano-1,3-dihydroisoindol-4-yl)-5-fluorobenzamide Chemical compound C(#N)N1CC2=CC=CC(=C2C1)C1=C(C(=O)N)C=C(C=C1)F FUEVEDMMGBYHSU-UHFFFAOYSA-N 0.000 claims 1
- ATYQOTHNRSLJLB-UHFFFAOYSA-N 2-(2-cyano-1,3-dihydroisoindol-4-yl)-5-methylbenzamide Chemical compound C(#N)N1CC2=CC=CC(=C2C1)C1=C(C(=O)N)C=C(C=C1)C ATYQOTHNRSLJLB-UHFFFAOYSA-N 0.000 claims 1
- FCHRGROJPQVWPJ-UHFFFAOYSA-N 2-(2-cyano-1,3-dihydroisoindol-4-yl)-N,N-dimethylbenzenesulfonamide Chemical compound C(#N)N1CC2=CC=CC(=C2C1)C1=C(C=CC=C1)S(=O)(=O)N(C)C FCHRGROJPQVWPJ-UHFFFAOYSA-N 0.000 claims 1
- MGDRPCGMKVGZMW-UHFFFAOYSA-N 2-(2-cyano-1,3-dihydroisoindol-4-yl)-N-ethylbenzenesulfonamide Chemical compound C(#N)N1CC2=CC=CC(=C2C1)C1=C(C=CC=C1)S(=O)(=O)NCC MGDRPCGMKVGZMW-UHFFFAOYSA-N 0.000 claims 1
- GSBPMZXZCVYNMA-UHFFFAOYSA-N 2-(2-cyano-1,3-dihydroisoindol-4-yl)-N-methylbenzenesulfonamide Chemical compound C(#N)N1CC2=CC=CC(=C2C1)C1=C(C=CC=C1)S(=O)(=O)NC GSBPMZXZCVYNMA-UHFFFAOYSA-N 0.000 claims 1
- AVJFZMRJMXTPPT-UHFFFAOYSA-N 2-(2-cyano-7-phenyl-1,3-dihydroisoindol-5-yl)-N,N-dimethylacetamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)CC(=O)N(C)C)C1=CC=CC=C1 AVJFZMRJMXTPPT-UHFFFAOYSA-N 0.000 claims 1
- RFISBCZWIGOSNF-UHFFFAOYSA-N 2-(2-hydroxyethylamino)-4-(4-methoxyphenyl)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound OCCNC=1N=C(C2=C(N=1)CN(C2)C#N)C1=CC=C(C=C1)OC RFISBCZWIGOSNF-UHFFFAOYSA-N 0.000 claims 1
- WVXJOEJOGLOYPA-UHFFFAOYSA-N 2-(2-hydroxyethylamino)-4-(4-phenoxypiperidin-1-yl)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound OCCNc1nc2CN(Cc2c(n1)N1CCC(CC1)Oc1ccccc1)C#N WVXJOEJOGLOYPA-UHFFFAOYSA-N 0.000 claims 1
- HJBJIRKRFYVWKK-UHFFFAOYSA-N 2-(2-hydroxyethylamino)-4-[3-(2-oxo-1,3-oxazolidin-3-yl)phenyl]-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound OCCNC=1N=C(C2=C(N=1)CN(C2)C#N)C1=CC(=CC=C1)N1C(OCC1)=O HJBJIRKRFYVWKK-UHFFFAOYSA-N 0.000 claims 1
- FKTGIZYCWXDGCU-UHFFFAOYSA-N 2-(2-hydroxyethylamino)-4-[3-(2-oxopyrrolidin-1-yl)phenyl]-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound OCCNC=1N=C(C2=C(N=1)CN(C2)C#N)C1=CC(=CC=C1)N1C(CCC1)=O FKTGIZYCWXDGCU-UHFFFAOYSA-N 0.000 claims 1
- FAMZFRADDXPVBT-UHFFFAOYSA-N 2-(2-hydroxyethylamino)-4-[4-(4-methylpiperazin-1-yl)phenyl]-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound OCCNC=1N=C(C2=C(N=1)CN(C2)C#N)C1=CC=C(C=C1)N1CCN(CC1)C FAMZFRADDXPVBT-UHFFFAOYSA-N 0.000 claims 1
- CFCXTKIDPXIFPW-UHFFFAOYSA-N 2-(2-hydroxyethylamino)-4-phenyl-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound OCCNc1nc2CN(Cc2c(n1)-c1ccccc1)C#N CFCXTKIDPXIFPW-UHFFFAOYSA-N 0.000 claims 1
- OKMNQYQZFSYLTM-UHFFFAOYSA-N 2-(2-methoxyphenyl)-4-pyrrolidin-1-yl-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound COC1=C(C=CC=C1)C=1N=C(C2=C(N=1)CN(C2)C#N)N1CCCC1 OKMNQYQZFSYLTM-UHFFFAOYSA-N 0.000 claims 1
- YGNTZJVWFWIWRJ-UHFFFAOYSA-N 2-(2-methylsulfonylethylamino)-4-phenyl-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound CS(=O)(=O)CCNC=1N=C(C2=C(N=1)CN(C2)C#N)C1=CC=CC=C1 YGNTZJVWFWIWRJ-UHFFFAOYSA-N 0.000 claims 1
- PMTGSPVAGYXWHF-UHFFFAOYSA-N 2-(3-cyanophenyl)-4-(3,4-dihydro-1H-isoquinolin-2-yl)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound C(#N)C=1C=C(C=CC=1)C=1N=C(C2=C(N=1)CN(C2)C#N)N1CC2=CC=CC=C2CC1 PMTGSPVAGYXWHF-UHFFFAOYSA-N 0.000 claims 1
- CCKHMUUPGBOUAC-UHFFFAOYSA-N 2-(3-imidazol-1-ylpropylamino)-4-phenyl-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound N1(C=NC=C1)CCCNC=1N=C(C2=C(N=1)CN(C2)C#N)C1=CC=CC=C1 CCKHMUUPGBOUAC-UHFFFAOYSA-N 0.000 claims 1
- LYWIHEFJTYEJKA-UHFFFAOYSA-N 2-(3-methoxyphenyl)-4-pyrrolidin-1-yl-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound COC=1C=C(C=CC=1)C=1N=C(C2=C(N=1)CN(C2)C#N)N1CCCC1 LYWIHEFJTYEJKA-UHFFFAOYSA-N 0.000 claims 1
- KVZLFSVALYBLEN-UHFFFAOYSA-N 2-(4-methoxyphenyl)-4-pyrrolidin-1-yl-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound COC1=CC=C(C=C1)C=1N=C(C2=C(N=1)CN(C2)C#N)N1CCCC1 KVZLFSVALYBLEN-UHFFFAOYSA-N 0.000 claims 1
- FJWJMJKRYNFRPR-UHFFFAOYSA-N 2-(5-methyl-1H-pyrazol-4-yl)-4-pyrrolidin-1-yl-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound CC1=C(C=NN1)C=1N=C(C2=C(N=1)CN(C2)C#N)N1CCCC1 FJWJMJKRYNFRPR-UHFFFAOYSA-N 0.000 claims 1
- MDVPBHHTKYITNB-UHFFFAOYSA-N 2-(furan-2-ylmethylamino)-4-phenyl-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound O1C(=CC=C1)CNC=1N=C(C2=C(N=1)CN(C2)C#N)C1=CC=CC=C1 MDVPBHHTKYITNB-UHFFFAOYSA-N 0.000 claims 1
- YIINQOBOVLCBSG-UHFFFAOYSA-N 2-(methylamino)-4-(4-phenoxypiperidin-1-yl)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound CNC=1N=C(C2=C(N=1)CN(C2)C#N)N1CCC(CC1)OC1=CC=CC=C1 YIINQOBOVLCBSG-UHFFFAOYSA-N 0.000 claims 1
- HDRUGINDQODLHC-UHFFFAOYSA-N 2-(oxan-4-ylamino)-4-phenyl-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound C1(=CC=CC=C1)C=1C2=C(N=C(N=1)NC1CCOCC1)CN(C2)C#N HDRUGINDQODLHC-UHFFFAOYSA-N 0.000 claims 1
- GGGDHOZQUAEIDW-UHFFFAOYSA-N 2-(oxan-4-ylmethylamino)-4-phenyl-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound C1(=CC=CC=C1)C=1C2=C(N=C(N=1)NCC1CCOCC1)CN(C2)C#N GGGDHOZQUAEIDW-UHFFFAOYSA-N 0.000 claims 1
- AXCUWQLNMJWZIL-UHFFFAOYSA-N 2-[(1-methylpiperidin-3-yl)methylamino]-4-phenyl-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound CN1CC(CCC1)CNC=1N=C(C2=C(N=1)CN(C2)C#N)C1=CC=CC=C1 AXCUWQLNMJWZIL-UHFFFAOYSA-N 0.000 claims 1
- SNHHNZCJTCHFTQ-UHFFFAOYSA-N 2-[(1-methylpyrrolidin-3-yl)methylamino]-4-phenyl-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound CN1CC(CC1)CNC=1N=C(C2=C(N=1)CN(C2)C#N)C1=CC=CC=C1 SNHHNZCJTCHFTQ-UHFFFAOYSA-N 0.000 claims 1
- TVRXGFHXVLVBBG-UHFFFAOYSA-N 2-[(2-methylpyrazol-3-yl)methylamino]-4-[3-(2-oxopyrrolidin-1-yl)phenyl]-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound CN1N=CC=C1CNC=1N=C(C2=C(N=1)CN(C2)C#N)C1=CC(=CC=C1)N1C(CCC1)=O TVRXGFHXVLVBBG-UHFFFAOYSA-N 0.000 claims 1
- MEQCJGQFUHMKCS-UHFFFAOYSA-N 2-[(2-methylpyrazol-3-yl)methylamino]-4-phenyl-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound CN1N=CC=C1CNC=1N=C(C2=C(N=1)CN(C2)C#N)C1=CC=CC=C1 MEQCJGQFUHMKCS-UHFFFAOYSA-N 0.000 claims 1
- XTCJEVOJJBXZJE-UHFFFAOYSA-N 2-[(4-methylmorpholin-2-yl)methylamino]-4-phenyl-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound CN1CC(OCC1)CNC=1N=C(C2=C(N=1)CN(C2)C#N)C1=CC=CC=C1 XTCJEVOJJBXZJE-UHFFFAOYSA-N 0.000 claims 1
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| GB201617758D0 (en) | 2016-10-20 | 2016-12-07 | Almac Discovery Limited | Pharmaceutical compounds |
| EP3601259B1 (en) | 2017-03-30 | 2022-02-23 | F. Hoffmann-La Roche AG | Isoquinolines as inhibitors of hpk1 |
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| AU2018346597B2 (en) | 2017-10-06 | 2023-07-13 | Forma Therapeutics, Inc. | Inhibiting Ubiquitin Specific Peptidase 30 |
| JP7449242B2 (ja) | 2018-05-17 | 2024-03-13 | フォーマ セラピューティクス，インコーポレイテッド | ユビキチン特異的ペプチダーゼ３０（ｕｓｐ３０）阻害剤として有用な縮合二環化合物 |
| TW202019905A (zh) | 2018-07-24 | 2020-06-01 | 瑞士商赫孚孟拉羅股份公司 | 異喹啉化合物及其用途 |
| US11572374B2 (en) | 2018-08-14 | 2023-02-07 | Amgen Inc. | N-cyano-7-azanorbornane derivatives and uses thereof |
| TW202024053A (zh) | 2018-10-02 | 2020-07-01 | 美商建南德克公司 | 異喹啉化合物及其用途 |
| US11612606B2 (en) | 2018-10-03 | 2023-03-28 | Genentech, Inc. | 8-aminoisoquinoline compounds and uses thereof |
| JP7530889B2 (ja) | 2018-10-05 | 2024-08-08 | フォーマ セラピューティクス，インコーポレイテッド | ユビキチン特異的プロテアーゼ３０（ｕｓｐ３０）阻害剤として作用する縮合ピロリン |
| CN109321940A (zh) * | 2018-11-30 | 2019-02-12 | 西南大学 | 一种酰胺的电化学氧化合成方法及其应用 |
| CN120698983A (zh) | 2018-12-20 | 2025-09-26 | C4医药公司 | 靶向蛋白降解 |
| WO2020139916A1 (en) * | 2018-12-26 | 2020-07-02 | Forma Therapeutics, Inc. | Inhibiting ubiquitin specific peptidase 9x |
| GB201905375D0 (en) | 2019-04-16 | 2019-05-29 | Mission Therapeutics Ltd | Novel compounds |
| GB201905371D0 (en) | 2019-04-16 | 2019-05-29 | Mission Therapeutics Ltd | Novel compounds |
| WO2021032935A1 (en) * | 2019-08-21 | 2021-02-25 | Kalvista Pharmaceuticals Limited | Enzyme inhibitors |
| GB201912674D0 (en) | 2019-09-04 | 2019-10-16 | Mission Therapeutics Ltd | Novel compounds |
| CN112538083B (zh) * | 2019-09-23 | 2023-04-28 | 华东师范大学 | 一类靶向bcl6的芳香环并五元芳杂环类小分子有机化合物及其衍生物及其应用 |
| CN110804041B (zh) * | 2019-09-25 | 2023-03-31 | 香港科技大学深圳研究院 | 抗肿瘤的吲哚类化合物的制备方法及吲哚类化合物和应用 |
| WO2021058018A1 (en) * | 2019-09-29 | 2021-04-01 | Beigene, Ltd. | Inhibitors of kras g12c |
| CN113135924B (zh) * | 2020-01-19 | 2024-04-26 | 广东东阳光药业股份有限公司 | 嘧啶衍生物及其在药物中的应用 |
| GB202001980D0 (en) | 2020-02-13 | 2020-04-01 | Almac Discovery Ltd | Therapeutic mentods |
| JP2023520727A (ja) | 2020-04-08 | 2023-05-18 | ミッション セラピューティクス リミティド | Ｕｓｐ３０阻害剤として活性を有するｎ－シアノピロリジン |
| IL298526A (en) | 2020-05-28 | 2023-01-01 | Mission Therapeutics Ltd | N-(1-cyano-pyrrolidin-3-yl)-5-(3-(trifluoromethyl)phenyl)oxazole-2-carboxamide derivatives and the corresponding oxadiazole derivatives as usp30 inhibitors for the treatment of mitochondrial dysfunction |
| US20230303547A1 (en) | 2020-06-04 | 2023-09-28 | Mission Therapeutics Limited | N-cyanopyrrolidines with activity as usp30 inhibitors |
| DK4161929T3 (da) | 2020-06-08 | 2025-08-18 | Mission Therapeutics Ltd | 1-(5-(2-cyanopyridin-4-yl)oxazol-2-carbonyl)-4-methylhexahydropyrrolo[3,4-b]pyrrol-5(1h)-carbonitril som usp30-hæmmer til anvendelse i behandling af mitokondriedysfunktion, cancer og fibrose |
| CN114053270B (zh) * | 2020-08-05 | 2023-06-13 | 兰州大学第二医院 | 泛素结合酶e2t的小分子抑制剂 |
| GB202016800D0 (en) | 2020-10-22 | 2020-12-09 | Mission Therapeutics Ltd | Novel compounds |
| US20240067657A1 (en) * | 2020-12-29 | 2024-02-29 | Merck Sharp & Dohme Llc | Amido-substituted pyridyl compounds and methods of use thereof for the treatment of herpesviruses |
| IL311132A (en) * | 2021-08-30 | 2024-04-01 | Remix Therapeutics Inc | Splicing Modulation Compounds and Methods |
| JP2024544660A (ja) | 2021-12-01 | 2024-12-03 | ミッション セラピューティクス リミティド | Ｕｓｐ３０阻害剤としての活性を有する置換ｎ－シアノピロリジン |
| MX2024007009A (es) * | 2021-12-08 | 2024-08-22 | Kineta Inc | Heteroarenos bicíclicos y métodos para su uso. |
| GB202200753D0 (en) | 2022-01-21 | 2022-03-09 | Almac Discovery Ltd | Pharmaceutical compounds |
| US12516064B2 (en) * | 2022-02-02 | 2026-01-06 | SpringWorks Therapeutics Inc. | Tetrahydropyridopyrimidines and related analogs for inhibiting YAP/TAZ-TEAD |
| CN121969626A (zh) * | 2023-09-27 | 2026-05-01 | 苏州必扬医药科技有限公司 | 一种Menin-MLL相互作用抑制剂及其制备方法和应用 |
| GB202408928D0 (en) | 2024-06-21 | 2024-08-07 | Mission Therapeutics Ltd | Novel compounds |
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Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5360569A (en) | 1993-11-12 | 1994-11-01 | Lever Brothers Company, Division Of Conopco, Inc. | Activation of bleach precursors with catalytic imine quaternary salts |
| EP1272467A4 (en) | 2000-04-06 | 2003-05-07 | Merck Frosst Canada Inc | Cathepsin cysteine protease inhibitors |
| WO2002022605A1 (en) * | 2000-09-15 | 2002-03-21 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| US7105667B2 (en) | 2001-05-01 | 2006-09-12 | Bristol-Myers Squibb Co. | Fused heterocyclic compounds and use thereof |
| WO2002088079A2 (en) | 2001-05-01 | 2002-11-07 | Bristol-Myers Squibb Company | Dual inhibitors of pde 7 and pde 4 |
| US7521557B2 (en) | 2005-05-20 | 2009-04-21 | Bristol-Myers Squibb Company | Pyrrolopyridine-based inhibitors of dipeptidyl peptidase IV and methods |
| CA2651072A1 (en) | 2006-05-01 | 2007-11-08 | Pfizer Products Inc. | Substituted 2-amino-fused heterocyclic compounds |
| WO2012040527A2 (en) | 2010-09-24 | 2012-03-29 | The Regents Of The University Of Michigan | Deubiquitinase inhibitors and methods for use of the same |
| BR112013020641B1 (pt) | 2011-02-25 | 2021-11-03 | Yuhan Corporation | Composto, composição farmacêutica, processos para a preparação de composto e respectivo uso ou de seu sal farmaceuticamente aceitável |
| EP2565186A1 (en) | 2011-09-02 | 2013-03-06 | Hybrigenics S.A. | Selective and reversible inhibitors of ubiquitin specific protease 7 |
| JP5833764B2 (ja) | 2011-09-30 | 2015-12-16 | 山東軒竹医薬科技有限公司 | 縮合環を有するオキサゾリドン（ｏｘａｚｏｌｉｄｏｎｅ）類の抗菌物質 |
| EP2938610A2 (en) * | 2012-12-28 | 2015-11-04 | The U.S.A. as represented by the Secretary, Department of Health and Human Services | Inhibitors of the usp1/uaf1 deubiquitinase complex and uses thereof |
| US20170137426A1 (en) | 2014-03-28 | 2017-05-18 | Changzhou Jiekai Pharmatech Co., Ltd. | Heterocyclic compounds as axl inhibitors |
| TR201807217T4 (tr) | 2014-07-08 | 2018-06-21 | Viiv Healthcare Uk Ltd | Bir viral enfeksiyon sahasının tedavisinde kullanım için izoindolin türevleri. |
| GB201416754D0 (en) | 2014-09-23 | 2014-11-05 | Mission Therapeutics Ltd | Novel compounds |
| CA2976741C (en) | 2015-03-30 | 2023-01-17 | Mission Therapeutics Limited | 1-cyano-pyrrolidine compounds as usp30 inhibitors |
| WO2017009650A1 (en) | 2015-07-14 | 2017-01-19 | Mission Therapeutics Limited | Cyanopyrrolidines as dub inhibitors for the treatment of cancer |
| GB201521109D0 (en) | 2015-11-30 | 2016-01-13 | Mission Therapeutics Ltd | Novel compounds |
| GB201522267D0 (en) | 2015-12-17 | 2016-02-03 | Mission Therapeutics Ltd | Novel compounds |
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| GB201603779D0 (en) | 2016-03-04 | 2016-04-20 | Mission Therapeutics Ltd | Novel compounds |
| GB201604638D0 (en) | 2016-03-18 | 2016-05-04 | Mission Therapeutics Ltd | Novel compounds |
| CN108884068B (zh) | 2016-03-24 | 2021-02-26 | 特殊治疗有限公司 | 作为dub抑制剂的1-氰基-吡咯烷衍生物 |
| US11014912B2 (en) | 2016-09-27 | 2021-05-25 | Mission Therapeutics Limited | Cyanopyrrolidine derivatives with activity as inhibitors of USP30 |
| GB201616511D0 (en) | 2016-09-29 | 2016-11-16 | Mission Therapeutics Limited | Novel compounds |
| GB201616627D0 (en) | 2016-09-30 | 2016-11-16 | Mission Therapeutics Limited | Novel compounds |
| TWI771327B (zh) | 2016-10-05 | 2022-07-21 | 英商使命醫療公司 | 新穎化合物 |
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2016
- 2016-03-18 GB GBGB1604647.6A patent/GB201604647D0/en not_active Ceased
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2017
- 2017-03-17 MA MA043746A patent/MA43746A/fr unknown
- 2017-03-17 WO PCT/GB2017/050763 patent/WO2017158388A1/en not_active Ceased
- 2017-03-17 EP EP17713408.7A patent/EP3429994B1/en active Active
- 2017-03-17 JP JP2018548744A patent/JP6959250B2/ja active Active
- 2017-03-17 CN CN201780009130.3A patent/CN108698992B/zh active Active
- 2017-03-17 US US16/080,506 patent/US10683269B2/en active Active