JP2019508467A5 - - Google Patents
Download PDFInfo
- 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
Links
- -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
- HYIXXWLIKYXFJR-UHFFFAOYSA-N 2-[2-hydroxyethyl(methyl)amino]-4-phenyl-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound OCCN(C=1N=C(C2=C(N=1)CN(C2)C#N)C1=CC=CC=C1)C HYIXXWLIKYXFJR-UHFFFAOYSA-N 0.000 claims 1
- XTCJEVOJJBXZJE-OAHLLOKOSA-N 2-[[(2R)-4-methylmorpholin-2-yl]methylamino]-4-phenyl-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound CN1CCO[C@H](CNc2nc3CN(Cc3c(n2)-c2ccccc2)C#N)C1 XTCJEVOJJBXZJE-OAHLLOKOSA-N 0.000 claims 1
- XTCJEVOJJBXZJE-HNNXBMFYSA-N 2-[[(2S)-4-methylmorpholin-2-yl]methylamino]-4-phenyl-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound CN1CCO[C@@H](CNc2nc3CN(Cc3c(n2)-c2ccccc2)C#N)C1 XTCJEVOJJBXZJE-HNNXBMFYSA-N 0.000 claims 1
- QRDJTRCNHFKMBS-UHFFFAOYSA-N 2-[methyl-[(4-methylmorpholin-2-yl)methyl]amino]-4-phenyl-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound CN(CC1CN(C)CCO1)c1nc2CN(Cc2c(n1)-c1ccccc1)C#N QRDJTRCNHFKMBS-UHFFFAOYSA-N 0.000 claims 1
- MLJBGTUOAOMERG-UHFFFAOYSA-N 2-amino-4-(4-phenoxypiperidin-1-yl)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound NC=1N=C(C2=C(N=1)CN(C2)C#N)N1CCC(CC1)OC1=CC=CC=C1 MLJBGTUOAOMERG-UHFFFAOYSA-N 0.000 claims 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- OERCHFYYUVEUPU-UHFFFAOYSA-N 2-anilino-4-phenyl-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound C1(=CC=CC=C1)C=1C2=C(N=C(N=1)NC1=CC=CC=C1)CN(C2)C#N OERCHFYYUVEUPU-UHFFFAOYSA-N 0.000 claims 1
- MXAZDPBJPFJDLP-UHFFFAOYSA-N 2-chloro-4-(2-fluorophenyl)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound ClC=1N=C(C2=C(N=1)CN(C2)C#N)C1=C(C=CC=C1)F MXAZDPBJPFJDLP-UHFFFAOYSA-N 0.000 claims 1
- WFSMQZMZFRSFAJ-UHFFFAOYSA-N 2-chloro-4-(4-fluorophenyl)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound ClC=1N=C(C2=C(N=1)CN(C2)C#N)C1=CC=C(C=C1)F WFSMQZMZFRSFAJ-UHFFFAOYSA-N 0.000 claims 1
- LLUUXOUBGFTPCV-UHFFFAOYSA-N 2-cyano-7-(2,4-dicyanophenyl)-N-methyl-1,3-dihydroisoindole-5-carboxamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)C(=O)NC)C1=C(C=C(C=C1)C#N)C#N LLUUXOUBGFTPCV-UHFFFAOYSA-N 0.000 claims 1
- BKMSWIIPQHWTTQ-UHFFFAOYSA-N 2-cyano-7-(2-cyano-5-methoxypyridin-3-yl)-N-methyl-1,3-dihydroisoindole-5-carboxamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)C(=O)NC)C=1C(=NC=C(C=1)OC)C#N BKMSWIIPQHWTTQ-UHFFFAOYSA-N 0.000 claims 1
- DUWVUJWUHVBOFB-UHFFFAOYSA-N 2-cyano-7-(4-cyanophenyl)-N,N-dimethyl-1,3-dihydroisoindole-5-carboxamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)C(=O)N(C)C)C1=CC=C(C=C1)C#N DUWVUJWUHVBOFB-UHFFFAOYSA-N 0.000 claims 1
- HRMLPQGPMNSZSY-UHFFFAOYSA-N 2-cyano-7-(4-cyanophenyl)-N-methyl-1,3-dihydroisoindole-5-carboxamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)C(=O)NC)C1=CC=C(C=C1)C#N HRMLPQGPMNSZSY-UHFFFAOYSA-N 0.000 claims 1
- IAGBUMYPEUBZII-UHFFFAOYSA-N 2-cyano-7-(4-fluorophenyl)-N-methyl-1,3-dihydroisoindole-5-carboxamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)C(=O)NC)C1=CC=C(C=C1)F IAGBUMYPEUBZII-UHFFFAOYSA-N 0.000 claims 1
- RVJJPJRFVHSGBB-UHFFFAOYSA-N 2-methyl-4-[3-(2-oxopyrrolidin-1-yl)phenyl]-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound CC=1N=C(C2=C(N=1)CN(C2)C#N)C1=CC(=CC=C1)N1C(CCC1)=O RVJJPJRFVHSGBB-UHFFFAOYSA-N 0.000 claims 1
- IOCBKPCEGDFMDL-UHFFFAOYSA-N 3-(2-cyano-1,3-dihydroisoindol-4-yl)-N-phenylbenzamide Chemical compound C(#N)N1CC2=CC=CC(=C2C1)C=1C=C(C(=O)NC2=CC=CC=C2)C=CC=1 IOCBKPCEGDFMDL-UHFFFAOYSA-N 0.000 claims 1
- 102000052553 3-Hydroxyacyl CoA Dehydrogenase Human genes 0.000 claims 1
- 108700020831 3-Hydroxyacyl-CoA Dehydrogenase Proteins 0.000 claims 1
- WIPVCOPHVOLPRV-UHFFFAOYSA-N 3-[(2-cyano-1,3-dihydroisoindol-4-yl)amino]-N-methylisoquinoline-6-carboxamide Chemical compound C(#N)N1CC2=CC=CC(=C2C1)NC=1N=CC2=CC=C(C=C2C=1)C(=O)NC WIPVCOPHVOLPRV-UHFFFAOYSA-N 0.000 claims 1
- FEXDASRGOJWIKU-UHFFFAOYSA-N 3-[[2-cyano-7-(4-cyanophenyl)-1,3-dihydroisoindol-5-yl]methyl]-1,1-dimethylurea Chemical compound CN(C)C(=O)NCC1=CC2=C(CN(C2)C#N)C(=C1)C1=CC=C(C=C1)C#N FEXDASRGOJWIKU-UHFFFAOYSA-N 0.000 claims 1
- QUKYTDAEBRGTSF-UHFFFAOYSA-N 4-(1,3-dihydroisoindol-2-yl)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound C1N(CC2=CC=CC=C12)C=1C2=C(N=CN=1)CN(C2)C#N QUKYTDAEBRGTSF-UHFFFAOYSA-N 0.000 claims 1
- MMMNQHHQZQRYBB-UHFFFAOYSA-N 4-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-1,3-dihydroisoindole-2-carbonitrile Chemical compound CN1CCC(=CC1)C1=C2CN(CC2=CC=C1)C#N MMMNQHHQZQRYBB-UHFFFAOYSA-N 0.000 claims 1
- WSYDPZVTWVVPPT-UHFFFAOYSA-N 4-(1-methylpiperidin-4-yl)-1,3-dihydroisoindole-2-carbonitrile Chemical compound CN1CCC(CC1)C1=C2CN(CC2=CC=C1)C#N WSYDPZVTWVVPPT-UHFFFAOYSA-N 0.000 claims 1
- ZBVOQBQXUCJUIW-UHFFFAOYSA-N 4-(1-methylpyrazol-4-yl)-1,3-dihydroisoindole-2-carbonitrile Chemical compound CN1N=CC(=C1)C1=C2CN(CC2=CC=C1)C#N ZBVOQBQXUCJUIW-UHFFFAOYSA-N 0.000 claims 1
- GAUGEOTWCYKAMR-UHFFFAOYSA-N 4-(1-methylpyrazol-4-yl)-1-phenyl-5,7-dihydropyrrolo[3,4-d]pyridazine-6-carbonitrile Chemical compound CN1N=CC(=C1)C1=NN=C(C2=C1CN(C2)C#N)C1=CC=CC=C1 GAUGEOTWCYKAMR-UHFFFAOYSA-N 0.000 claims 1
- WQEYAQJOFPGIQI-UHFFFAOYSA-N 4-(1-oxo-3,4-dihydro-2H-isoquinolin-8-yl)-1,3-dihydroisoindole-2-carbonitrile Chemical compound O=C1NCCC2=CC=CC(=C12)C1=C2CN(CC2=CC=C1)C#N WQEYAQJOFPGIQI-UHFFFAOYSA-N 0.000 claims 1
- KSLNOEGPRBYOPH-UHFFFAOYSA-N 4-(1H-pyrrolo[2,3-b]pyridin-5-yl)-1,3-dihydroisoindole-2-carbonitrile Chemical compound N#CN1Cc2cccc(c2C1)-c1cnc2[nH]ccc2c1 KSLNOEGPRBYOPH-UHFFFAOYSA-N 0.000 claims 1
- MFOLRDPRLQCBPN-UHFFFAOYSA-N 4-(2,6-dioxopiperidin-1-yl)-1,3-dihydroisoindole-2-carbonitrile Chemical compound O=C1N(C(CCC1)=O)C1=C2CN(CC2=CC=C1)C#N MFOLRDPRLQCBPN-UHFFFAOYSA-N 0.000 claims 1
- NGMOJUJHTVAUFV-UHFFFAOYSA-N 4-(2-acetylphenyl)-1,3-dihydroisoindole-2-carbonitrile Chemical compound C(C)(=O)C1=C(C=CC=C1)C1=C2CN(CC2=CC=C1)C#N NGMOJUJHTVAUFV-UHFFFAOYSA-N 0.000 claims 1
- FPBBDONOAOEMSJ-UHFFFAOYSA-N 4-(2-chloro-4-cyanophenyl)-1,3-dihydroisoindole-2-carbonitrile Chemical compound ClC1=C(C=CC(=C1)C#N)C1=C2CN(CC2=CC=C1)C#N FPBBDONOAOEMSJ-UHFFFAOYSA-N 0.000 claims 1
- CADBXKCNMBZCKY-UHFFFAOYSA-N 4-(2-cyano-1,3-dihydroisoindol-4-yl)benzene-1,3-dicarbonitrile Chemical compound C(#N)N1CC2=CC=CC(=C2C1)C1=C(C=C(C#N)C=C1)C#N CADBXKCNMBZCKY-UHFFFAOYSA-N 0.000 claims 1
- KSMCPQAYCJDTCL-UHFFFAOYSA-N 4-(2-cyano-4-fluorophenyl)-1,3-dihydroisoindole-2-carbonitrile Chemical compound C(#N)C1=C(C=CC(=C1)F)C1=C2CN(CC2=CC=C1)C#N KSMCPQAYCJDTCL-UHFFFAOYSA-N 0.000 claims 1
- YNUZZLYDFHIYHO-UHFFFAOYSA-N 4-(2-cyano-4-imidazol-1-ylphenyl)-1,3-dihydroisoindole-2-carbonitrile Chemical compound C(#N)C1=C(C=CC(=C1)N1C=NC=C1)C1=C2CN(CC2=CC=C1)C#N YNUZZLYDFHIYHO-UHFFFAOYSA-N 0.000 claims 1
- ASZJORZGOHZYSA-UHFFFAOYSA-N 4-(2-cyano-4-methoxyphenyl)-1,3-dihydroisoindole-2-carbonitrile Chemical compound C(#N)C1=C(C=CC(=C1)OC)C1=C2CN(CC2=CC=C1)C#N ASZJORZGOHZYSA-UHFFFAOYSA-N 0.000 claims 1
- RBKWIOXKESYJMS-UHFFFAOYSA-N 4-(2-cyano-5-methoxyphenyl)-1,3-dihydroisoindole-2-carbonitrile Chemical compound C(#N)C1=C(C=C(C=C1)OC)C1=C2CN(CC2=CC=C1)C#N RBKWIOXKESYJMS-UHFFFAOYSA-N 0.000 claims 1
- KMWSNIYHFRJUCD-UHFFFAOYSA-N 4-(2-cyano-6-fluorophenyl)-1,3-dihydroisoindole-2-carbonitrile Chemical compound C(#N)C1=C(C(=CC=C1)F)C1=C2CN(CC2=CC=C1)C#N KMWSNIYHFRJUCD-UHFFFAOYSA-N 0.000 claims 1
- KGUHTMVWONJXOT-UHFFFAOYSA-N 4-(2-cyanophenyl)-1,3-dihydroisoindole-2-carbonitrile Chemical compound C(#N)C1=C(C=CC=C1)C1=C2CN(CC2=CC=C1)C#N KGUHTMVWONJXOT-UHFFFAOYSA-N 0.000 claims 1
- TYMODOMUHJFNNR-INIZCTEOSA-N 4-(2-cyanophenyl)-6-[[(2S)-2,3-dihydroxypropyl]amino]-1,3-dihydroisoindole-2-carbonitrile Chemical compound C(#N)C1=C(C=CC=C1)C1=C2CN(CC2=CC(=C1)NC[C@@H](CO)O)C#N TYMODOMUHJFNNR-INIZCTEOSA-N 0.000 claims 1
- MCNDRPRQSMWAKM-UHFFFAOYSA-N 4-(2-methylindazol-5-yl)-1,3-dihydroisoindole-2-carbonitrile Chemical compound CN1N=C2C=CC(=CC2=C1)C1=C2CN(CC2=CC=C1)C#N MCNDRPRQSMWAKM-UHFFFAOYSA-N 0.000 claims 1
- YPSRRMXSNTWTEA-UHFFFAOYSA-N 4-(2-methylphenyl)-1,3-dihydroisoindole-2-carbonitrile Chemical compound C1(=C(C=CC=C1)C1=C2CN(CC2=CC=C1)C#N)C YPSRRMXSNTWTEA-UHFFFAOYSA-N 0.000 claims 1
- CQVVNIUMQUWHDT-UHFFFAOYSA-N 4-(2-methylsulfonylphenyl)-1,3-dihydroisoindole-2-carbonitrile Chemical compound CS(=O)(=O)C1=C(C=CC=C1)C1=C2CN(CC2=CC=C1)C#N CQVVNIUMQUWHDT-UHFFFAOYSA-N 0.000 claims 1
- PGWGVIOOHRJJRZ-UHFFFAOYSA-N 4-(2-oxo-1,3-dihydroindol-7-yl)-1,3-dihydroisoindole-2-carbonitrile Chemical compound O=C1NC2=C(C=CC=C2C1)C1=C2CN(CC2=CC=C1)C#N PGWGVIOOHRJJRZ-UHFFFAOYSA-N 0.000 claims 1
- LWUKZMAWYOGARD-UHFFFAOYSA-N 4-(3,4-difluorophenyl)-2-(2-hydroxyethylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound FC=1C=C(C=CC=1F)C=1C2=C(N=C(N=1)NCCO)CN(C2)C#N LWUKZMAWYOGARD-UHFFFAOYSA-N 0.000 claims 1
- KFLLTKBVHQQUNZ-UHFFFAOYSA-N 4-(3,4-dihydro-1H-isoquinolin-2-yl)-2-(1-methylpyrazol-4-yl)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound C1N(CCC2=CC=CC=C12)C=1C2=C(N=C(N=1)C=1C=NN(C=1)C)CN(C2)C#N KFLLTKBVHQQUNZ-UHFFFAOYSA-N 0.000 claims 1
- GDWNCGRHCVSSAH-UHFFFAOYSA-N 4-(3,4-dihydro-1H-isoquinolin-2-yl)-2-(1H-pyrazol-4-yl)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound C1N(CCC2=CC=CC=C12)C=1C2=C(N=C(N=1)C=1C=NNC=1)CN(C2)C#N GDWNCGRHCVSSAH-UHFFFAOYSA-N 0.000 claims 1
- ZETHUEVBAGXIRS-UHFFFAOYSA-N 4-(3,4-dihydro-1H-isoquinolin-2-yl)-2-(5-methyl-1H-pyrazol-4-yl)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound C1N(CCC2=CC=CC=C12)C=1C2=C(N=C(N=1)C=1C=NNC=1C)CN(C2)C#N ZETHUEVBAGXIRS-UHFFFAOYSA-N 0.000 claims 1
- DGUFQMBOTHMREG-UHFFFAOYSA-N 4-(3,4-dihydro-1H-isoquinolin-2-yl)-2-[(4-methylmorpholin-2-yl)methylamino]-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound CN1CCOC(CNc2nc3CN(Cc3c(n2)N2CCc3ccccc3C2)C#N)C1 DGUFQMBOTHMREG-UHFFFAOYSA-N 0.000 claims 1
- KYNJCIGFINFRHC-UHFFFAOYSA-N 4-(3,4-dihydro-1H-isoquinolin-2-yl)-2-[1-(2-methoxyethyl)pyrazol-4-yl]-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound C1N(CCC2=CC=CC=C12)C=1C2=C(N=C(N=1)C=1C=NN(C=1)CCOC)CN(C2)C#N KYNJCIGFINFRHC-UHFFFAOYSA-N 0.000 claims 1
- FGVKPFBYKIUORB-UHFFFAOYSA-N 4-(3,4-dihydro-1H-isoquinolin-2-yl)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound N#CN1Cc2ncnc(N3CCc4ccccc4C3)c2C1 FGVKPFBYKIUORB-UHFFFAOYSA-N 0.000 claims 1
- LVHJCIAKGBPBSK-UHFFFAOYSA-N 4-(3-chlorophenyl)-5,7-dihydropyrrolo[3,4-b]pyridine-6-carbonitrile Chemical compound ClC=1C=C(C=CC=1)C1=C2C(=NC=C1)CN(C2)C#N LVHJCIAKGBPBSK-UHFFFAOYSA-N 0.000 claims 1
- FBKUHXKYQUZYDT-UHFFFAOYSA-N 4-(3-cyano-6-methoxypyridin-2-yl)-1,3-dihydroisoindole-2-carbonitrile Chemical compound C(#N)C=1C(=NC(=CC=1)OC)C1=C2CN(CC2=CC=C1)C#N FBKUHXKYQUZYDT-UHFFFAOYSA-N 0.000 claims 1
- POHAHXPELZVSJH-UHFFFAOYSA-N 4-(3-fluorophenyl)-2-[(4-methylmorpholin-2-yl)methylamino]-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound CN1CCOC(CNc2nc3CN(Cc3c(n2)-c2cccc(F)c2)C#N)C1 POHAHXPELZVSJH-UHFFFAOYSA-N 0.000 claims 1
- NHGMGPSZHJTKOE-UHFFFAOYSA-N 4-(3-oxo-1,2-dihydroisoindol-4-yl)-1,3-dihydroisoindole-2-carbonitrile Chemical compound O=C1NCC=2C=CC=C(C1=2)C=1C=2CN(CC=2C=CC=1)C#N NHGMGPSZHJTKOE-UHFFFAOYSA-N 0.000 claims 1
- IUYYXYJALCQSLL-UHFFFAOYSA-N 4-(4-chloro-2-cyanophenyl)-1,3-dihydroisoindole-2-carbonitrile Chemical compound ClC1=CC(=C(C=C1)C1=C2CN(CC2=CC=C1)C#N)C#N IUYYXYJALCQSLL-UHFFFAOYSA-N 0.000 claims 1
- QDCQBMFGXHVZKK-UHFFFAOYSA-N 4-(4-chlorophenyl)-5,7-dihydropyrrolo[3,4-b]pyridine-6-carbonitrile Chemical compound ClC1=CC=C(C=C1)C1=C2C(=NC=C1)CN(C2)C#N QDCQBMFGXHVZKK-UHFFFAOYSA-N 0.000 claims 1
- WQVUSWMAHPQKEV-UHFFFAOYSA-N 4-(4-cyano-2,6-dimethylphenyl)-1,3-dihydroisoindole-2-carbonitrile Chemical compound C(#N)C1=CC(=C(C(=C1)C)C1=C2CN(CC2=CC=C1)C#N)C WQVUSWMAHPQKEV-UHFFFAOYSA-N 0.000 claims 1
- IIPGQKMEYQQSPY-UHFFFAOYSA-N 4-(4-cyano-2-methylphenyl)-1,3-dihydroisoindole-2-carbonitrile Chemical compound C(#N)C1=CC(=C(C=C1)C1=C2CN(CC2=CC=C1)C#N)C IIPGQKMEYQQSPY-UHFFFAOYSA-N 0.000 claims 1
- MLYBOHGNUKPWDD-UHFFFAOYSA-N 4-(4-cyanophenyl)-1,3-dihydroisoindole-2-carbonitrile Chemical compound C(#N)C1=CC=C(C=C1)C1=C2CN(CC2=CC=C1)C#N MLYBOHGNUKPWDD-UHFFFAOYSA-N 0.000 claims 1
- GKPNMWRWDXFTFT-UHFFFAOYSA-N 4-(4-cyanophenyl)-2-(2-hydroxyethylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound C(#N)C1=CC=C(C=C1)C=1C2=C(N=C(N=1)NCCO)CN(C2)C#N GKPNMWRWDXFTFT-UHFFFAOYSA-N 0.000 claims 1
- GPYVXXYENZKOEW-UHFFFAOYSA-N 4-(4-cyanophenyl)-6-(2,3-dihydroxypropylamino)-1,3-dihydroisoindole-2-carbonitrile Chemical compound C(#N)C1=CC=C(C=C1)C1=C2CN(CC2=CC(=C1)NCC(CO)O)C#N GPYVXXYENZKOEW-UHFFFAOYSA-N 0.000 claims 1
- CEUAONXGTVXCLU-UHFFFAOYSA-N 4-(4-cyanophenyl)-6-(2-hydroxyethylamino)-1,3-dihydroisoindole-2-carbonitrile Chemical compound C(#N)C1=CC=C(C=C1)C1=C2CN(CC2=CC(=C1)NCCO)C#N CEUAONXGTVXCLU-UHFFFAOYSA-N 0.000 claims 1
- ADZYJLKKCCTGNH-UHFFFAOYSA-N 4-(4-cyanophenyl)-6-(2-hydroxypropylamino)-1,3-dihydroisoindole-2-carbonitrile Chemical compound C(#N)C1=CC=C(C=C1)C1=C2CN(CC2=CC(=C1)NCC(C)O)C#N ADZYJLKKCCTGNH-UHFFFAOYSA-N 0.000 claims 1
- KGLWBPZYFUWXSU-UHFFFAOYSA-N 4-(4-cyanophenyl)-6-(2-methoxyethyl)-1,3-dihydroisoindole-2-carbonitrile Chemical compound C(#N)C1=CC=C(C=C1)C1=C2CN(CC2=CC(=C1)CCOC)C#N KGLWBPZYFUWXSU-UHFFFAOYSA-N 0.000 claims 1
- KOCPLRDMQYULEX-UHFFFAOYSA-N 4-(4-cyanophenyl)-6-(2-pyridin-3-ylethyl)-1,3-dihydroisoindole-2-carbonitrile Chemical compound C(#N)C1=CC=C(C=C1)C1=C2CN(CC2=CC(=C1)CCC=1C=NC=CC=1)C#N KOCPLRDMQYULEX-UHFFFAOYSA-N 0.000 claims 1
- KEVCGMXDVSYFGG-UHFFFAOYSA-N 4-(4-cyanophenyl)-6-(diethylamino)-1,3-dihydroisoindole-2-carbonitrile Chemical compound C(#N)C1=CC=C(C=C1)C1=C2CN(CC2=CC(=C1)N(CC)CC)C#N KEVCGMXDVSYFGG-UHFFFAOYSA-N 0.000 claims 1
- VJTXNGNIXOCFKQ-UHFFFAOYSA-N 4-(4-cyanophenyl)-6-(dimethylamino)-1,3-dihydroisoindole-2-carbonitrile Chemical compound C(#N)C1=CC=C(C=C1)C1=C2CN(CC2=CC(=C1)N(C)C)C#N VJTXNGNIXOCFKQ-UHFFFAOYSA-N 0.000 claims 1
- MVTILIGERVFLMT-UHFFFAOYSA-N 4-(4-cyanophenyl)-6-(ethylamino)-1,3-dihydroisoindole-2-carbonitrile Chemical compound C(#N)C1=CC=C(C=C1)C1=C2CN(CC2=CC(=C1)NCC)C#N MVTILIGERVFLMT-UHFFFAOYSA-N 0.000 claims 1
- MTQAKGHFEBDWNS-UHFFFAOYSA-N 4-(4-cyanophenyl)-6-(methylamino)-1,3-dihydroisoindole-2-carbonitrile Chemical compound C(#N)C1=CC=C(C=C1)C1=C2CN(CC2=CC(=C1)NC)C#N MTQAKGHFEBDWNS-UHFFFAOYSA-N 0.000 claims 1
- LFPMQUVMMCQKJT-UHFFFAOYSA-N 4-(4-cyanophenyl)-6-(methylsulfonylmethyl)-1,3-dihydroisoindole-2-carbonitrile Chemical compound C(#N)C1=CC=C(C=C1)C1=C2CN(CC2=CC(=C1)CS(=O)(=O)C)C#N LFPMQUVMMCQKJT-UHFFFAOYSA-N 0.000 claims 1
- FLOHIOXSYUHYPG-UHFFFAOYSA-N 4-(4-cyanophenyl)-6-(oxan-4-ylamino)-1,3-dihydroisoindole-2-carbonitrile Chemical compound C(#N)C1=CC=C(C=C1)C1=C2CN(CC2=CC(=C1)NC1CCOCC1)C#N FLOHIOXSYUHYPG-UHFFFAOYSA-N 0.000 claims 1
- ICOJPVYTMPAQPO-UHFFFAOYSA-N 4-(4-cyanophenyl)-6-(oxan-4-ylmethylamino)-1,3-dihydroisoindole-2-carbonitrile Chemical compound C(#N)C1=CC=C(C=C1)C1=C2CN(CC2=CC(=C1)NCC1CCOCC1)C#N ICOJPVYTMPAQPO-UHFFFAOYSA-N 0.000 claims 1
- DHECGRFEROTKJE-UHFFFAOYSA-N 4-(4-cyanophenyl)-6-(propan-2-ylamino)-1,3-dihydroisoindole-2-carbonitrile Chemical compound C(#N)C1=CC=C(C=C1)C1=C2CN(CC2=CC(=C1)NC(C)C)C#N DHECGRFEROTKJE-UHFFFAOYSA-N 0.000 claims 1
- YEKNNLVTEORZIO-UHFFFAOYSA-N 4-(4-cyanophenyl)-6-[(1H-pyrazol-5-ylamino)methyl]-1,3-dihydroisoindole-2-carbonitrile Chemical compound N1N=CC=C1NCC1=CC(=C2CN(CC2=C1)C#N)C1=CC=C(C=C1)C#N YEKNNLVTEORZIO-UHFFFAOYSA-N 0.000 claims 1
- AJBWTJBCNGUJOV-UHFFFAOYSA-N 4-(4-cyanophenyl)-6-[(2-hydroxy-2-methylpropyl)amino]-1,3-dihydroisoindole-2-carbonitrile Chemical compound C(#N)C1=CC=C(C=C1)C1=C2CN(CC2=CC(=C1)NCC(C)(C)O)C#N AJBWTJBCNGUJOV-UHFFFAOYSA-N 0.000 claims 1
- QBZRYCAVXIPMGU-UHFFFAOYSA-N 4-(4-cyanophenyl)-6-[(2-hydroxy-3-methoxypropyl)amino]-1,3-dihydroisoindole-2-carbonitrile Chemical compound C(#N)C1=CC=C(C=C1)C1=C2CN(CC2=CC(=C1)NCC(COC)O)C#N QBZRYCAVXIPMGU-UHFFFAOYSA-N 0.000 claims 1
- WIWYEVFUERXTRO-UHFFFAOYSA-N 4-(4-cyanophenyl)-6-[(2-methylpyrazol-3-yl)methylamino]-1,3-dihydroisoindole-2-carbonitrile Chemical compound C(#N)C1=CC=C(C=C1)C1=C2CN(CC2=CC(=C1)NCC1=CC=NN1C)C#N WIWYEVFUERXTRO-UHFFFAOYSA-N 0.000 claims 1
- QQTKZCUNAYONLI-UHFFFAOYSA-N 4-(4-cyanophenyl)-6-[(3-hydroxy-2-methoxypropyl)amino]-1,3-dihydroisoindole-2-carbonitrile Chemical compound C(#N)C1=CC=C(C=C1)C1=C2CN(CC2=CC(=C1)NCC(CO)OC)C#N QQTKZCUNAYONLI-UHFFFAOYSA-N 0.000 claims 1
- YGSANOSOXRPRFK-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-(oxan-4-ylmethylamino)-5,7-dihydropyrrolo[3,4-b]pyridine-6-carbonitrile Chemical compound FC1=CC=C(C=C1)C1=C2C(=NC(=C1)NCC1CCOCC1)CN(C2)C#N YGSANOSOXRPRFK-UHFFFAOYSA-N 0.000 claims 1
- OXOBPVUCUZDNJP-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-(pyridin-2-ylmethylamino)-5,7-dihydropyrrolo[3,4-b]pyridine-6-carbonitrile Chemical compound FC1=CC=C(C=C1)C1=C2C(=NC(=C1)NCC1=NC=CC=C1)CN(C2)C#N OXOBPVUCUZDNJP-UHFFFAOYSA-N 0.000 claims 1
- SFWBCFXOCSYDBB-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-[(2-methylpyrazol-3-yl)methylamino]-5,7-dihydropyrrolo[3,4-b]pyridine-6-carbonitrile Chemical compound FC1=CC=C(C=C1)C1=C2C(=NC(=C1)NCC1=CC=NN1C)CN(C2)C#N SFWBCFXOCSYDBB-UHFFFAOYSA-N 0.000 claims 1
- OFGKAXFTEPKUHM-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-methyl-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound FC1=CC=C(C=C1)C=1C2=C(N=C(N=1)C)CN(C2)C#N OFGKAXFTEPKUHM-UHFFFAOYSA-N 0.000 claims 1
- CGNHJHPHCCLBPV-UHFFFAOYSA-N 4-(4-methoxyphenyl)-5,7-dihydropyrrolo[3,4-b]pyridine-6-carbonitrile Chemical compound COC1=CC=C(C=C1)C1=C2C(=NC=C1)CN(C2)C#N CGNHJHPHCCLBPV-UHFFFAOYSA-N 0.000 claims 1
- HBAYEYGBOXTEPF-UHFFFAOYSA-N 4-(4-phenylmethoxypiperidin-1-yl)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound C(C1=CC=CC=C1)OC1CCN(CC1)C=1C2=C(N=CN=1)CN(C2)C#N HBAYEYGBOXTEPF-UHFFFAOYSA-N 0.000 claims 1
- OXTWQAXWFKRSHM-UHFFFAOYSA-N 4-(4-pyridin-3-yloxypiperidin-1-yl)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound N1=CC(=CC=C1)OC1CCN(CC1)C=1C2=C(N=CN=1)CN(C2)C#N OXTWQAXWFKRSHM-UHFFFAOYSA-N 0.000 claims 1
- JEIOOJUAZGBRKP-UHFFFAOYSA-N 4-(6,8-dihydro-5H-1,7-naphthyridin-7-yl)-2-(5-methyl-1H-pyrazol-4-yl)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound CC1=C(C=NN1)C1=NC(N2CCC3=CC=CN=C3C2)=C2CN(CC2=N1)C#N JEIOOJUAZGBRKP-UHFFFAOYSA-N 0.000 claims 1
- WQFYCGCAQUKAGK-UHFFFAOYSA-N 4-(6,8-dihydro-5H-1,7-naphthyridin-7-yl)-2-[methyl-[(1-methylpiperidin-3-yl)methyl]amino]-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound CN(CC1CCCN(C)C1)C1=NC(N2CCC3=CC=CN=C3C2)=C2CN(CC2=N1)C#N WQFYCGCAQUKAGK-UHFFFAOYSA-N 0.000 claims 1
- AKAJUELYIYQHEM-UHFFFAOYSA-N 4-(quinazolin-2-ylamino)-1,3-dihydroisoindole-2-carbonitrile Chemical compound N1=C(N=CC2=CC=CC=C12)NC1=C2CN(CC2=CC=C1)C#N AKAJUELYIYQHEM-UHFFFAOYSA-N 0.000 claims 1
- ONEPQGVIFAFWDA-UHFFFAOYSA-N 4-[2-(azetidin-1-ylsulfonyl)phenyl]-1,3-dihydroisoindole-2-carbonitrile Chemical compound N1(CCC1)S(=O)(=O)C1=C(C=CC=C1)C1=C2CN(CC2=CC=C1)C#N ONEPQGVIFAFWDA-UHFFFAOYSA-N 0.000 claims 1
- OVTXXZXNDPXUEO-UHFFFAOYSA-N 4-[2-(azetidine-1-carbonyl)-4-cyanophenyl]-1,3-dihydroisoindole-2-carbonitrile Chemical compound N1(CCC1)C(=O)C1=C(C=CC(=C1)C#N)C1=C2CN(CC2=CC=C1)C#N OVTXXZXNDPXUEO-UHFFFAOYSA-N 0.000 claims 1
- YEHWHZHUTKPNJR-UHFFFAOYSA-N 4-[2-(piperazine-1-carbonyl)phenyl]-1,3-dihydroisoindole-2-carbonitrile Chemical compound N1(CCNCC1)C(=O)C1=C(C=CC=C1)C1=C2CN(CC2=CC=C1)C#N YEHWHZHUTKPNJR-UHFFFAOYSA-N 0.000 claims 1
- PSSVOVPJVXAWJK-UHFFFAOYSA-N 4-[2-(pyrrolidine-1-carbonyl)phenyl]-1,3-dihydroisoindole-2-carbonitrile Chemical compound N1(CCCC1)C(=O)C1=C(C=CC=C1)C1=C2CN(CC2=CC=C1)C#N PSSVOVPJVXAWJK-UHFFFAOYSA-N 0.000 claims 1
- ILPCZOGEHRPPGQ-GFCCVEGCSA-N 4-[2-[(1R)-1-hydroxyethyl]phenyl]-1,3-dihydroisoindole-2-carbonitrile Chemical compound O[C@H](C)C1=C(C=CC=C1)C1=C2CN(CC2=CC=C1)C#N ILPCZOGEHRPPGQ-GFCCVEGCSA-N 0.000 claims 1
- ILPCZOGEHRPPGQ-LBPRGKRZSA-N 4-[2-[(1S)-1-hydroxyethyl]phenyl]-1,3-dihydroisoindole-2-carbonitrile Chemical compound O[C@@H](C)C1=C(C=CC=C1)C1=C2CN(CC2=CC=C1)C#N ILPCZOGEHRPPGQ-LBPRGKRZSA-N 0.000 claims 1
- OGJGGGMBJHBZSW-UHFFFAOYSA-N 4-[2-cyano-4-(1H-pyrazol-4-yl)phenyl]-1,3-dihydroisoindole-2-carbonitrile Chemical compound C(#N)C1=C(C=CC(=C1)C=1C=NNC=1)C1=C2CN(CC2=CC=C1)C#N OGJGGGMBJHBZSW-UHFFFAOYSA-N 0.000 claims 1
- FICBLLXVTPXCMY-UHFFFAOYSA-N 4-[2-cyano-5-(2-oxo-1,3-oxazolidin-3-yl)phenyl]-1,3-dihydroisoindole-2-carbonitrile Chemical compound C(#N)C1=C(C=C(C=C1)N1C(OCC1)=O)C1=C2CN(CC2=CC=C1)C#N FICBLLXVTPXCMY-UHFFFAOYSA-N 0.000 claims 1
- XYZMRBSZHBVSIQ-UHFFFAOYSA-N 4-[2-cyano-5-(2-oxopyrrolidin-1-yl)phenyl]-1,3-dihydroisoindole-2-carbonitrile Chemical compound C(#N)C1=C(C=C(C=C1)N1C(CCC1)=O)C1=C2CN(CC2=CC=C1)C#N XYZMRBSZHBVSIQ-UHFFFAOYSA-N 0.000 claims 1
- GQNMBTPRWQJZMO-UHFFFAOYSA-N 4-[3-(2-oxoimidazolidin-1-yl)phenyl]-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound O=C1N(CCN1)C=1C=C(C=CC=1)C=1C2=C(N=CN=1)CN(C2)C#N GQNMBTPRWQJZMO-UHFFFAOYSA-N 0.000 claims 1
- OQRGVEBTLABKEF-UHFFFAOYSA-N 4-[4-(2,4-difluorophenyl)piperazin-1-yl]-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound FC1=C(C=CC(=C1)F)N1CCN(CC1)C=1C2=C(N=CN=1)CN(C2)C#N OQRGVEBTLABKEF-UHFFFAOYSA-N 0.000 claims 1
- FNVRICJHGNCNFS-UHFFFAOYSA-N 4-[4-(2-methoxyphenoxy)piperidin-1-yl]-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound COC1=C(OC2CCN(CC2)C=2C3=C(N=CN=2)CN(C3)C#N)C=CC=C1 FNVRICJHGNCNFS-UHFFFAOYSA-N 0.000 claims 1
- HBLDDMPABBSWOW-UHFFFAOYSA-N 4-[4-(2-methylphenoxy)piperidin-1-yl]-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound C1(=C(C=CC=C1)OC1CCN(CC1)C=1C2=C(N=CN=1)CN(C2)C#N)C HBLDDMPABBSWOW-UHFFFAOYSA-N 0.000 claims 1
- NZMKWGWPMVMWKC-UHFFFAOYSA-N 4-[4-(3-methoxyphenoxy)piperidin-1-yl]-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound COc1cccc(OC2CCN(CC2)c2ncnc3CN(Cc23)C#N)c1 NZMKWGWPMVMWKC-UHFFFAOYSA-N 0.000 claims 1
- JXWJEJMCIANYEL-UHFFFAOYSA-N 4-[4-cyano-2-(trifluoromethyl)phenyl]-1,3-dihydroisoindole-2-carbonitrile Chemical compound C(#N)C1=CC(=C(C=C1)C1=C2CN(CC2=CC=C1)C#N)C(F)(F)F JXWJEJMCIANYEL-UHFFFAOYSA-N 0.000 claims 1
- SWXSZBILZBPQPW-UHFFFAOYSA-N 4-phenyl-1,3-dihydroisoindole-2-carbonitrile Chemical compound C1(=CC=CC=C1)C1=C2CN(CC2=CC=C1)C#N SWXSZBILZBPQPW-UHFFFAOYSA-N 0.000 claims 1
- WAINFCPXRKKFSS-UHFFFAOYSA-N 4-phenyl-1,3-dihydropyrrolo[3,4-c]pyridine-2-carbonitrile Chemical compound N#CN1CC2=C(C1)C(=NC=C2)C1=CC=CC=C1 WAINFCPXRKKFSS-UHFFFAOYSA-N 0.000 claims 1
- DJSLPIHXBNMLAV-UHFFFAOYSA-N 4-phenyl-2-(1,2,3,4-tetrahydronaphthalen-1-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound N#CN1Cc2nc(NC3CCCc4ccccc34)nc(c2C1)-c1ccccc1 DJSLPIHXBNMLAV-UHFFFAOYSA-N 0.000 claims 1
- XECXYFVBHSBWDM-UHFFFAOYSA-N 4-phenyl-2-(1,3-thiazol-5-ylmethylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound C1(=CC=CC=C1)C=1C2=C(N=C(N=1)NCC1=CN=CS1)CN(C2)C#N XECXYFVBHSBWDM-UHFFFAOYSA-N 0.000 claims 1
- LIDZECZLJNHMOV-UHFFFAOYSA-N 4-phenyl-2-(2-pyridin-2-ylethylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound N#CN1Cc2nc(NCCc3ccccn3)nc(c2C1)-c1ccccc1 LIDZECZLJNHMOV-UHFFFAOYSA-N 0.000 claims 1
- CKTSXSSFPYUPME-UHFFFAOYSA-N 4-phenyl-2-(pyridin-2-ylmethylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound C1(=CC=CC=C1)C=1C2=C(N=C(N=1)NCC1=NC=CC=C1)CN(C2)C#N CKTSXSSFPYUPME-UHFFFAOYSA-N 0.000 claims 1
- GAROQIIRHBJVQE-UHFFFAOYSA-N 4-phenyl-2-(pyridin-3-ylmethylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound C1(=CC=CC=C1)C=1C2=C(N=C(N=1)NCC=1C=NC=CC=1)CN(C2)C#N GAROQIIRHBJVQE-UHFFFAOYSA-N 0.000 claims 1
- UBHLRLJPMCZHKD-UHFFFAOYSA-N 4-phenyl-2-(pyrimidin-2-ylmethylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidine-6-carbonitrile Chemical compound C1(=CC=CC=C1)C=1C2=C(N=C(N=1)NCC1=NC=CC=N1)CN(C2)C#N UBHLRLJPMCZHKD-UHFFFAOYSA-N 0.000 claims 1
- ZLSBTSDWXPZEDJ-UHFFFAOYSA-N 4-quinolin-3-yl-1,3-dihydroisoindole-2-carbonitrile Chemical compound N1=CC(=CC2=CC=CC=C12)C1=C2CN(CC2=CC=C1)C#N ZLSBTSDWXPZEDJ-UHFFFAOYSA-N 0.000 claims 1
- RTEFKQMATUPYHS-UHFFFAOYSA-N 5-cyano-2-(2,6-dicyano-1,3-dihydroisoindol-4-yl)-3-fluorobenzamide Chemical compound C(#N)C=1C=C(C(=C(C(=O)N)C=1)C1=C2CN(CC2=CC(=C1)C#N)C#N)F RTEFKQMATUPYHS-UHFFFAOYSA-N 0.000 claims 1
- FKQVFTFJCPTEEX-UHFFFAOYSA-N 5-cyano-2-(2-cyano-1,3-dihydroisoindol-4-yl)-3-fluorobenzamide Chemical compound C(#N)C=1C=C(C(=C(C(=O)N)C=1)C1=C2CN(CC2=CC=C1)C#N)F FKQVFTFJCPTEEX-UHFFFAOYSA-N 0.000 claims 1
- RWBMZIMUDVUHFJ-UHFFFAOYSA-N 5-cyano-2-(2-cyano-1,3-dihydroisoindol-4-yl)-4-methylbenzamide Chemical compound C(#N)C=1C(=CC(=C(C(=O)N)C=1)C1=C2CN(CC2=CC=C1)C#N)C RWBMZIMUDVUHFJ-UHFFFAOYSA-N 0.000 claims 1
- XTPDDIDCJYLTTB-UHFFFAOYSA-N 6-(1-methyl-6-oxopiperidin-3-yl)-4-phenyl-1,3-dihydroisoindole-2-carbonitrile Chemical compound CN1CC(CCC1=O)C1=CC(=C2CN(CC2=C1)C#N)C1=CC=CC=C1 XTPDDIDCJYLTTB-UHFFFAOYSA-N 0.000 claims 1
- LUOKNMJZOIEAEB-UHFFFAOYSA-N 6-(1-methyl-6-oxopyridin-3-yl)-4-phenyl-1,3-dihydroisoindole-2-carbonitrile Chemical compound CN1C=C(C=CC1=O)C1=CC(=C2CN(CC2=C1)C#N)C1=CC=CC=C1 LUOKNMJZOIEAEB-UHFFFAOYSA-N 0.000 claims 1
- VUFDDWLUMWKOFY-UHFFFAOYSA-N 6-(2-methoxyethyl)-4-phenyl-1,3-dihydroisoindole-2-carbonitrile Chemical compound COCCC1=CC(=C2CN(CC2=C1)C#N)C1=CC=CC=C1 VUFDDWLUMWKOFY-UHFFFAOYSA-N 0.000 claims 1
- SBPHBHMZFRJESB-UHFFFAOYSA-N 6-(2-methylsulfonylethyl)-4-phenyl-1,3-dihydroisoindole-2-carbonitrile Chemical compound CS(=O)(=O)CCC1=CC(=C2CN(CC2=C1)C#N)C1=CC=CC=C1 SBPHBHMZFRJESB-UHFFFAOYSA-N 0.000 claims 1
- CYGFJSNBMSHDCW-UHFFFAOYSA-N 6-(5-methyl-1,2,4-oxadiazol-3-yl)-4-phenyl-1,3-dihydroisoindole-2-carbonitrile Chemical compound CC1=NC(=NO1)C1=CC(=C2CN(CC2=C1)C#N)C1=CC=CC=C1 CYGFJSNBMSHDCW-UHFFFAOYSA-N 0.000 claims 1
- XJTVFXWZEYWUMM-UHFFFAOYSA-N 6-(methylsulfonylmethyl)-4-phenyl-1,3-dihydroisoindole-2-carbonitrile Chemical compound CS(=O)(=O)CC1=CC(=C2CN(CC2=C1)C#N)C1=CC=CC=C1 XJTVFXWZEYWUMM-UHFFFAOYSA-N 0.000 claims 1
- LYKAPNTVPILIIP-UHFFFAOYSA-N 6-[(1-methylpiperidin-3-yl)methylamino]-4-phenyl-1,3-dihydroisoindole-2-carbonitrile Chemical compound CN1CC(CCC1)CNC1=CC(=C2CN(CC2=C1)C#N)C1=CC=CC=C1 LYKAPNTVPILIIP-UHFFFAOYSA-N 0.000 claims 1
- FMCKKKKETCPGIY-UHFFFAOYSA-N 6-[(1-methylpyrazol-4-yl)amino]-4-phenyl-1,3-dihydroisoindole-2-carbonitrile Chemical compound CN1N=CC(=C1)NC1=CC(=C2CN(CC2=C1)C#N)C1=CC=CC=C1 FMCKKKKETCPGIY-UHFFFAOYSA-N 0.000 claims 1
- PUGRUUVFZZUMHE-UHFFFAOYSA-N 6-[(dimethylamino)methyl]-4-phenyl-1,3-dihydroisoindole-2-carbonitrile Chemical compound CN(C)CC1=CC(=C2CN(CC2=C1)C#N)C1=CC=CC=C1 PUGRUUVFZZUMHE-UHFFFAOYSA-N 0.000 claims 1
- FDEOTUIJAONHOO-UHFFFAOYSA-N 6-[2-(1-acetylpiperidin-4-yl)ethyl]-4-(4-cyanophenyl)-1,3-dihydroisoindole-2-carbonitrile Chemical compound C(C)(=O)N1CCC(CC1)CCC1=CC(=C2CN(CC2=C1)C#N)C1=CC=C(C=C1)C#N FDEOTUIJAONHOO-UHFFFAOYSA-N 0.000 claims 1
- WUKOAYJVDRSWSC-INIZCTEOSA-N 6-[[(2S)-2,3-dihydroxypropyl]amino]-4-(4-fluorophenyl)-1,3-dihydroisoindole-2-carbonitrile Chemical compound O[C@@H](CNC1=CC(=C2CN(CC2=C1)C#N)C1=CC=C(C=C1)F)CO WUKOAYJVDRSWSC-INIZCTEOSA-N 0.000 claims 1
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 1
- 238000006412 Alper carbonylation reaction Methods 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 206010003591 Ataxia Diseases 0.000 claims 1
- 201000005943 Barth syndrome Diseases 0.000 claims 1
- DGYOFXLGTMFFPT-UHFFFAOYSA-N C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)C1CCN(CC1)C)C1=CC=CC=C1 Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)C1CCN(CC1)C)C1=CC=CC=C1 DGYOFXLGTMFFPT-UHFFFAOYSA-N 0.000 claims 1
- PEMYZCNAYYCMNO-UHFFFAOYSA-N C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)C1CN(C(C1)=O)C)C1=CC=C(C=C1)C#N Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)C1CN(C(C1)=O)C)C1=CC=C(C=C1)C#N PEMYZCNAYYCMNO-UHFFFAOYSA-N 0.000 claims 1
- CKMFANKMFHAIPM-UHFFFAOYSA-N C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)C1CN(C(CC1)=O)C)C1=CC=C(C=C1)C#N Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)C1CN(C(CC1)=O)C)C1=CC=C(C=C1)C#N CKMFANKMFHAIPM-UHFFFAOYSA-N 0.000 claims 1
- VYTGEAGDLWLEPP-KRWDZBQOSA-N C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)[C@@H]1CN(CCC1)C)C1=CC=CC=C1 Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)[C@@H]1CN(CCC1)C)C1=CC=CC=C1 VYTGEAGDLWLEPP-KRWDZBQOSA-N 0.000 claims 1
- LRAAFRWXGQBCIG-QGZVFWFLSA-N C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)[C@H]1CN(CCC1)C)C1=CC(=CC=C1)OC Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)[C@H]1CN(CCC1)C)C1=CC(=CC=C1)OC LRAAFRWXGQBCIG-QGZVFWFLSA-N 0.000 claims 1
- LBRLXRKPYHZJGP-GOSISDBHSA-N C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)[C@H]1CN(CCC1)C)C1=CC=C(C=C1)C#N Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)[C@H]1CN(CCC1)C)C1=CC=C(C=C1)C#N LBRLXRKPYHZJGP-GOSISDBHSA-N 0.000 claims 1
- XBCYPJFMMJTJSV-GOSISDBHSA-N C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)[C@H]1CN(CCC1)C)C1=CC=C(C=C1)C(NC)=O Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)[C@H]1CN(CCC1)C)C1=CC=C(C=C1)C(NC)=O XBCYPJFMMJTJSV-GOSISDBHSA-N 0.000 claims 1
- RTMLUTYBGJZUDI-QGZVFWFLSA-N C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)[C@H]1CN(CCC1)C)C1=CC=C(C=C1)OC Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)[C@H]1CN(CCC1)C)C1=CC=C(C=C1)OC RTMLUTYBGJZUDI-QGZVFWFLSA-N 0.000 claims 1
- VYTGEAGDLWLEPP-QGZVFWFLSA-N C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)[C@H]1CN(CCC1)C)C1=CC=CC=C1 Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)[C@H]1CN(CCC1)C)C1=CC=CC=C1 VYTGEAGDLWLEPP-QGZVFWFLSA-N 0.000 claims 1
- MFPUFYKOLYOPGL-MRXNPFEDSA-N C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)[C@H]1CN(CCC1)C)C1=CC=NC=C1 Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)[C@H]1CN(CCC1)C)C1=CC=NC=C1 MFPUFYKOLYOPGL-MRXNPFEDSA-N 0.000 claims 1
- LYFCNRPKOKXOCW-UHFFFAOYSA-N C(#N)N1CC2=C(C=C(C=C2C1)NC(CCC(=O)N(C)C)=O)C1=CC=CC=C1 Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NC(CCC(=O)N(C)C)=O)C1=CC=CC=C1 LYFCNRPKOKXOCW-UHFFFAOYSA-N 0.000 claims 1
- BXCUNUPVWLAXNP-UHFFFAOYSA-N C1N(CCC2=CC=CC=C12)C=1C2=C(N=C(N=1)C1=C(C=CC=C1)OC)CN(C2)C#N Chemical compound C1N(CCC2=CC=CC=C12)C=1C2=C(N=C(N=1)C1=C(C=CC=C1)OC)CN(C2)C#N BXCUNUPVWLAXNP-UHFFFAOYSA-N 0.000 claims 1
- ZVTZTYAQKQOMCM-UHFFFAOYSA-N C1N(CCC2=CC=CC=C12)C=1C2=C(N=C(N=1)NCC1=CC=NN1C)CN(C2)C#N Chemical compound C1N(CCC2=CC=CC=C12)C=1C2=C(N=C(N=1)NCC1=CC=NN1C)CN(C2)C#N ZVTZTYAQKQOMCM-UHFFFAOYSA-N 0.000 claims 1
- HZRQLUGZUZBCFV-UHFFFAOYSA-N C1N(CCC2=CC=CC=C12)C=1C2=C(N=C(N=1)NCC1CN(CCC1)C)CN(C2)C#N Chemical compound C1N(CCC2=CC=CC=C12)C=1C2=C(N=C(N=1)NCC1CN(CCC1)C)CN(C2)C#N HZRQLUGZUZBCFV-UHFFFAOYSA-N 0.000 claims 1
- JVAGQWAHHNMWCE-UHFFFAOYSA-N C1N(CCC2=CC=CC=C12)C=1C2=C(N=C(N=1)NCC=1C=NN(C=1)C)CN(C2)C#N Chemical compound C1N(CCC2=CC=CC=C12)C=1C2=C(N=C(N=1)NCC=1C=NN(C=1)C)CN(C2)C#N JVAGQWAHHNMWCE-UHFFFAOYSA-N 0.000 claims 1
- XMIVRWXHOYOOLB-UHFFFAOYSA-N C1N(CCC2=CC=CC=C12)C=1C2=C(N=C(N=1)NCCO)CN(C2)C#N Chemical compound C1N(CCC2=CC=CC=C12)C=1C2=C(N=C(N=1)NCCO)CN(C2)C#N XMIVRWXHOYOOLB-UHFFFAOYSA-N 0.000 claims 1
- ZRVWQQGUSVKSGF-UHFFFAOYSA-N CN(C=1N=C(C2=C(N=1)CN(C2)C#N)N1CCC(CC1)OC1=CC=CC=C1)C Chemical compound CN(C=1N=C(C2=C(N=1)CN(C2)C#N)N1CCC(CC1)OC1=CC=CC=C1)C ZRVWQQGUSVKSGF-UHFFFAOYSA-N 0.000 claims 1
- RXVHFQHISXXNFV-UHFFFAOYSA-N CN1CC(OCC1)CNC=1N=C(C2=C(N=1)CN(C2)C#N)C=1C=NC=CC=1 Chemical compound CN1CC(OCC1)CNC=1N=C(C2=C(N=1)CN(C2)C#N)C=1C=NC=CC=1 RXVHFQHISXXNFV-UHFFFAOYSA-N 0.000 claims 1
- GBKOAHHIRRMYSZ-UHFFFAOYSA-N CN1N=CC(=C1)NC=1N=C(C2=C(N=1)CN(C2)C#N)C1=CC=CC=C1 Chemical compound CN1N=CC(=C1)NC=1N=C(C2=C(N=1)CN(C2)C#N)C1=CC=CC=C1 GBKOAHHIRRMYSZ-UHFFFAOYSA-N 0.000 claims 1
- 208000031229 Cardiomyopathies Diseases 0.000 claims 1
- 108700005858 Carnitine palmitoyl transferase 2 deficiency Proteins 0.000 claims 1
- 201000002929 Carnitine palmitoyltransferase II deficiency Diseases 0.000 claims 1
- 206010008025 Cerebellar ataxia Diseases 0.000 claims 1
- COIFHXNAIALBPV-MRXNPFEDSA-N ClC1=CC=C(C=C1)C=1C=C(C=C2CN(CC=12)C#N)NC(=O)[C@H]1CN(CCC1)C Chemical compound ClC1=CC=C(C=C1)C=1C=C(C=C2CN(CC=12)C#N)NC(=O)[C@H]1CN(CCC1)C COIFHXNAIALBPV-MRXNPFEDSA-N 0.000 claims 1
- YAFNXVNUBGDVBI-MRXNPFEDSA-N ClC=1C=C(C=CC=1)C=1C=C(C=C2CN(CC=12)C#N)NC(=O)[C@H]1CN(CCC1)C Chemical compound ClC=1C=C(C=CC=1)C=1C=C(C=C2CN(CC=12)C#N)NC(=O)[C@H]1CN(CCC1)C YAFNXVNUBGDVBI-MRXNPFEDSA-N 0.000 claims 1
- 208000010354 Coenzyme Q10 deficiency Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- 101150073133 Cpt1a gene Proteins 0.000 claims 1
- 208000021075 Creatine deficiency syndrome Diseases 0.000 claims 1
- 208000002155 Cytochrome-c Oxidase Deficiency Diseases 0.000 claims 1
- 206010067889 Dementia with Lewy bodies Diseases 0.000 claims 1
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims 1
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims 1
- BCUWUIQTMXGXMU-UHFFFAOYSA-N FC1=CC=C(C=C1)C=1C2=C(N=C(N=1)NCC1CN(CCO1)C)CN(C2)C#N Chemical compound FC1=CC=C(C=C1)C=1C2=C(N=C(N=1)NCC1CN(CCO1)C)CN(C2)C#N BCUWUIQTMXGXMU-UHFFFAOYSA-N 0.000 claims 1
- 206010016654 Fibrosis Diseases 0.000 claims 1
- 201000011240 Frontotemporal dementia Diseases 0.000 claims 1
- 208000009796 Gangliosidoses Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 101000804964 Homo sapiens DNA polymerase subunit gamma-1 Proteins 0.000 claims 1
- 101001083553 Homo sapiens Hydroxyacyl-coenzyme A dehydrogenase, mitochondrial Proteins 0.000 claims 1
- 101000595929 Homo sapiens POLG alternative reading frame Proteins 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- 102100030358 Hydroxyacyl-coenzyme A dehydrogenase, mitochondrial Human genes 0.000 claims 1
- 208000018142 Leiomyosarcoma Diseases 0.000 claims 1
- 201000002832 Lewy body dementia Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 208000035172 MERRF Diseases 0.000 claims 1
- 208000025205 Mantle-Cell Lymphoma Diseases 0.000 claims 1
- 206010050029 Mitochondrial cytopathy Diseases 0.000 claims 1
- 206010072928 Mucolipidosis type II Diseases 0.000 claims 1
- 206010072929 Mucolipidosis type III Diseases 0.000 claims 1
- 102100026502 Mucolipin-1 Human genes 0.000 claims 1
- 208000034578 Multiple myelomas Diseases 0.000 claims 1
- 208000036572 Myoclonic epilepsy Diseases 0.000 claims 1
- GKCGTOGHFPDVNG-UHFFFAOYSA-N N-(2-cyano-1,3-dihydroisoindol-4-yl)-2-phenyl-1,3-thiazole-4-carboxamide Chemical compound C(#N)N1CC2=CC=CC(=C2C1)NC(=O)C=1N=C(SC=1)C1=CC=CC=C1 GKCGTOGHFPDVNG-UHFFFAOYSA-N 0.000 claims 1
- NUDXSVULBPHYCV-UHFFFAOYSA-N N-(2-cyano-1,3-dihydroisoindol-4-yl)-3-(2-methylphenyl)-1H-pyrazole-5-carboxamide Chemical compound C(#N)N1CC2=CC=CC(=C2C1)NC(=O)C1=CC(=NN1)C1=C(C=CC=C1)C NUDXSVULBPHYCV-UHFFFAOYSA-N 0.000 claims 1
- XJYTYYINJUMPSL-UHFFFAOYSA-N N-(2-cyano-1,3-dihydroisoindol-4-yl)-3-pyrazin-2-yl-1H-pyrazole-5-carboxamide Chemical compound C(#N)N1CC2=CC=CC(=C2C1)NC(=O)C1=NNC(=C1)C1=NC=CN=C1 XJYTYYINJUMPSL-UHFFFAOYSA-N 0.000 claims 1
- NWBOMHGXGAHUIE-UHFFFAOYSA-N N-(2-cyano-1,3-dihydroisoindol-4-yl)-5-methoxy-1H-pyrrolo[2,3-c]pyridine-2-carboxamide Chemical compound C(#N)N1CC2=CC=CC(=C2C1)NC(=O)C1=CC=2C(=CN=C(C=2)OC)N1 NWBOMHGXGAHUIE-UHFFFAOYSA-N 0.000 claims 1
- OKIXPXFUWPUNDA-UHFFFAOYSA-N N-(2-cyano-1,3-dihydroisoindol-4-yl)-5-morpholin-4-ylthiophene-2-carboxamide Chemical compound O=C(Nc1cccc2CN(Cc12)C#N)c1ccc(s1)N1CCOCC1 OKIXPXFUWPUNDA-UHFFFAOYSA-N 0.000 claims 1
- FPRJVVPSKHYUJT-UHFFFAOYSA-N N-(2-cyano-1,3-dihydroisoindol-5-yl)-1-methylpyrrolidine-3-carboxamide Chemical compound C(#N)N1CC2=CC=C(C=C2C1)NC(=O)C1CN(CC1)C FPRJVVPSKHYUJT-UHFFFAOYSA-N 0.000 claims 1
- XCJCGRYPLWZLBA-UHFFFAOYSA-N N-(2-cyano-4-phenyl-1,3-dihydroisoindol-5-yl)acetamide Chemical compound C(#N)N1CC2=CC=C(C(=C2C1)C1=CC=CC=C1)NC(C)=O XCJCGRYPLWZLBA-UHFFFAOYSA-N 0.000 claims 1
- CGWAXPPNNBADQI-UHFFFAOYSA-N N-(2-cyano-7-phenyl-1,3-dihydroisoindol-5-yl)-1,1-dioxothiane-4-carboxamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)C1CCS(CC1)(=O)=O)C1=CC=CC=C1 CGWAXPPNNBADQI-UHFFFAOYSA-N 0.000 claims 1
- WPVADMYYEBAHKD-UHFFFAOYSA-N N-(2-cyano-7-phenyl-1,3-dihydroisoindol-5-yl)-1-methyl-5-oxopyrrolidine-3-carboxamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)C1CN(C(C1)=O)C)C1=CC=CC=C1 WPVADMYYEBAHKD-UHFFFAOYSA-N 0.000 claims 1
- DXBQBKZGTAWIKS-UHFFFAOYSA-N N-(2-cyano-7-phenyl-1,3-dihydroisoindol-5-yl)-1-methyl-6-oxopiperidine-3-carboxamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)C1CN(C(CC1)=O)C)C1=CC=CC=C1 DXBQBKZGTAWIKS-UHFFFAOYSA-N 0.000 claims 1
- VYTGEAGDLWLEPP-UHFFFAOYSA-N N-(2-cyano-7-phenyl-1,3-dihydroisoindol-5-yl)-1-methylpiperidine-3-carboxamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)C1CN(CCC1)C)C1=CC=CC=C1 VYTGEAGDLWLEPP-UHFFFAOYSA-N 0.000 claims 1
- AJABEMPGNKVQSF-UHFFFAOYSA-N N-(2-cyano-7-phenyl-1,3-dihydroisoindol-5-yl)-1-methylpyrrolidine-3-carboxamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)C1CN(CC1)C)C1=CC=CC=C1 AJABEMPGNKVQSF-UHFFFAOYSA-N 0.000 claims 1
- ZZJAUSMGPKUJMF-UHFFFAOYSA-N N-(2-cyano-7-phenyl-1,3-dihydroisoindol-5-yl)-2-methylpyrazole-3-carboxamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)C1=CC=NN1C)C1=CC=CC=C1 ZZJAUSMGPKUJMF-UHFFFAOYSA-N 0.000 claims 1
- LBDSVDMNBWTTRE-UHFFFAOYSA-N N-(2-cyano-7-phenyl-1,3-dihydroisoindol-5-yl)-4-ethylmorpholine-2-carboxamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)C1CN(CCO1)CC)C1=CC=CC=C1 LBDSVDMNBWTTRE-UHFFFAOYSA-N 0.000 claims 1
- ISFHHCUITXWSBJ-UHFFFAOYSA-N N-(2-cyano-7-phenyl-1,3-dihydroisoindol-5-yl)-4-methylmorpholine-2-carboxamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)C1CN(CCO1)C)C1=CC=CC=C1 ISFHHCUITXWSBJ-UHFFFAOYSA-N 0.000 claims 1
- SOWYHYDVYMOWFF-UHFFFAOYSA-N N-(2-cyano-7-phenyl-1,3-dihydroisoindol-5-yl)-4-methylpiperazine-1-carboxamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)N1CCN(CC1)C)C1=CC=CC=C1 SOWYHYDVYMOWFF-UHFFFAOYSA-N 0.000 claims 1
- CSMBZPMBYWEIPH-UHFFFAOYSA-N N-(2-cyano-7-phenyl-1,3-dihydroisoindol-5-yl)-4-propan-2-ylmorpholine-2-carboxamide Chemical compound CC(C)N1CCOC(C1)C(=O)Nc1cc2CN(Cc2c(c1)-c1ccccc1)C#N CSMBZPMBYWEIPH-UHFFFAOYSA-N 0.000 claims 1
- SXEXTVMBCUOFMY-UHFFFAOYSA-N N-(2-cyano-7-phenyl-1,3-dihydroisoindol-5-yl)-5-oxopyrrolidine-3-carboxamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)C1CNC(C1)=O)C1=CC=CC=C1 SXEXTVMBCUOFMY-UHFFFAOYSA-N 0.000 claims 1
- WDQHLLHXKVMIDU-UHFFFAOYSA-N N-(2-cyano-7-phenyl-1,3-dihydroisoindol-5-yl)-N,1-dimethylpiperidine-3-carboxamide Chemical compound CN(C(=O)C1CCCN(C)C1)c1cc2CN(Cc2c(c1)-c1ccccc1)C#N WDQHLLHXKVMIDU-UHFFFAOYSA-N 0.000 claims 1
- GXODYZUPLFZTRE-UHFFFAOYSA-N N-(2-cyano-7-phenyl-1,3-dihydroisoindol-5-yl)-N-methylacetamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)N(C(C)=O)C)C1=CC=CC=C1 GXODYZUPLFZTRE-UHFFFAOYSA-N 0.000 claims 1
- QAFCQZMGQLZIPV-UHFFFAOYSA-N N-(2-cyano-7-phenyl-1,3-dihydroisoindol-5-yl)acetamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NC(C)=O)C1=CC=CC=C1 QAFCQZMGQLZIPV-UHFFFAOYSA-N 0.000 claims 1
- WNJHOVJOFATFHS-UHFFFAOYSA-N N-(2-cyano-7-phenyl-1,3-dihydroisoindol-5-yl)methanesulfonamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NS(=O)(=O)C)C1=CC=CC=C1 WNJHOVJOFATFHS-UHFFFAOYSA-N 0.000 claims 1
- PRKGTYSUBGCIFY-UHFFFAOYSA-N N-(2-cyano-7-phenyl-1,3-dihydroisoindol-5-yl)oxane-4-carboxamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)C1CCOCC1)C1=CC=CC=C1 PRKGTYSUBGCIFY-UHFFFAOYSA-N 0.000 claims 1
- SJIRWHSKBHBIRJ-UHFFFAOYSA-N N-(2-cyano-7-phenyl-1,3-dihydroisoindol-5-yl)piperidine-3-carboxamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)C1CNCCC1)C1=CC=CC=C1 SJIRWHSKBHBIRJ-UHFFFAOYSA-N 0.000 claims 1
- WMLDWAPFJJCCGN-UHFFFAOYSA-N N-(2-cyano-7-phenyl-1,3-dihydroisoindol-5-yl)pyridine-3-carboxamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NC(C1=CN=CC=C1)=O)C1=CC=CC=C1 WMLDWAPFJJCCGN-UHFFFAOYSA-N 0.000 claims 1
- BXYBEWMBVJFMPL-UHFFFAOYSA-N N-(6-cyano-4-phenyl-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-yl)-5-oxopyrrolidine-3-carboxamide Chemical compound C(#N)N1CC=2N=C(N=C(C=2C1)C1=CC=CC=C1)NC(=O)C1CNC(C1)=O BXYBEWMBVJFMPL-UHFFFAOYSA-N 0.000 claims 1
- XUQNZOGCHNKIJW-UHFFFAOYSA-N N-(6-cyano-4-phenyl-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-yl)acetamide Chemical compound C(#N)N1CC=2N=C(N=C(C=2C1)C1=CC=CC=C1)NC(C)=O XUQNZOGCHNKIJW-UHFFFAOYSA-N 0.000 claims 1
- XQZNASVVHBTDCP-UHFFFAOYSA-N N-(6-cyano-4-pyrrolidin-1-yl-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-yl)acetamide Chemical compound C(#N)N1CC=2N=C(N=C(C=2C1)N1CCCC1)NC(C)=O XQZNASVVHBTDCP-UHFFFAOYSA-N 0.000 claims 1
- IRMGWVZLDXQMQT-UHFFFAOYSA-N N-[(2-cyano-7-phenyl-1,3-dihydroisoindol-5-yl)methyl]acetamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)CNC(C)=O)C1=CC=CC=C1 IRMGWVZLDXQMQT-UHFFFAOYSA-N 0.000 claims 1
- ARKVZRVPWDZUEB-UHFFFAOYSA-N N-[2-cyano-7-(2,4-dicyanophenyl)-1,3-dihydroisoindol-5-yl]methanesulfonamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NS(=O)(=O)C)C1=C(C=C(C=C1)C#N)C#N ARKVZRVPWDZUEB-UHFFFAOYSA-N 0.000 claims 1
- JXFCWYTWCLCQSG-UHFFFAOYSA-N N-[2-cyano-7-(2-cyano-5-methoxyphenyl)-1,3-dihydroisoindol-5-yl]methanesulfonamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NS(=O)(=O)C)C1=C(C=CC(=C1)OC)C#N JXFCWYTWCLCQSG-UHFFFAOYSA-N 0.000 claims 1
- RDHVTUANIUUSOT-UHFFFAOYSA-N N-[2-cyano-7-(2-cyanophenyl)-1,3-dihydroisoindol-5-yl]methanesulfonamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NS(=O)(=O)C)C1=C(C=CC=C1)C#N RDHVTUANIUUSOT-UHFFFAOYSA-N 0.000 claims 1
- JVZUWPPRWVMFRD-UHFFFAOYSA-N N-[2-cyano-7-(4-cyanophenyl)-1,3-dihydroisoindol-5-yl]methanesulfonamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NS(=O)(=O)C)C1=CC=C(C=C1)C#N JVZUWPPRWVMFRD-UHFFFAOYSA-N 0.000 claims 1
- JBDGTHDEWMYWSS-UHFFFAOYSA-N N-[2-cyano-7-(4-cyanophenyl)-1,3-dihydroisoindol-5-yl]oxane-4-carboxamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)NC(=O)C1CCOCC1)C1=CC=C(C=C1)C#N JBDGTHDEWMYWSS-UHFFFAOYSA-N 0.000 claims 1
- YTOYLJZMHSJTDG-UHFFFAOYSA-N N-[3-(2-acetamido-6-cyano-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl)phenyl]acetamide Chemical compound C(C)(=O)NC=1N=C(C2=C(N=1)CN(C2)C#N)C=1C=C(C=CC=1)NC(C)=O YTOYLJZMHSJTDG-UHFFFAOYSA-N 0.000 claims 1
- RTLLLXKLYUQVAQ-UHFFFAOYSA-N N-[3-[6-cyano-2-(2-hydroxyethylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]phenyl]acetamide Chemical compound C(#N)N1CC=2N=C(N=C(C=2C1)C=1C=C(C=CC=1)NC(C)=O)NCCO RTLLLXKLYUQVAQ-UHFFFAOYSA-N 0.000 claims 1
- FRNDSOVTOCZCKF-UHFFFAOYSA-N N-[3-[6-cyano-2-[(4-methylmorpholin-2-yl)methylamino]-5,7-dihydropyrrolo[3,4-d]pyrimidin-4-yl]phenyl]acetamide Chemical compound CN1CCOC(CNc2nc3CN(Cc3c(n2)-c2cccc(NC(C)=O)c2)C#N)C1 FRNDSOVTOCZCKF-UHFFFAOYSA-N 0.000 claims 1
- REMRZKVUNLBEAP-UHFFFAOYSA-N N-[6-cyano-4-(1-methylpyrazol-4-yl)-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-yl]acetamide Chemical compound C(#N)N1CC=2N=C(N=C(C=2C1)C=1C=NN(C=1)C)NC(C)=O REMRZKVUNLBEAP-UHFFFAOYSA-N 0.000 claims 1
- PXULCUKYABICRS-UHFFFAOYSA-N N-[6-cyano-4-(3,4-dihydro-1H-isoquinolin-2-yl)-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-yl]acetamide Chemical compound C(#N)N1CC=2N=C(N=C(C=2C1)N1CC2=CC=CC=C2CC1)NC(C)=O PXULCUKYABICRS-UHFFFAOYSA-N 0.000 claims 1
- KXNCCIFRTCDDRH-UHFFFAOYSA-N N-[6-cyano-4-(3-cyanophenyl)-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-yl]acetamide Chemical compound C(#N)N1CC=2N=C(N=C(C=2C1)C1=CC(=CC=C1)C#N)NC(C)=O KXNCCIFRTCDDRH-UHFFFAOYSA-N 0.000 claims 1
- PPZJZRLLRBFSTD-UHFFFAOYSA-N N-[6-cyano-4-(4-fluorophenyl)-5,7-dihydropyrrolo[3,4-b]pyridin-2-yl]acetamide Chemical compound C(#N)N1CC2=NC(=CC(=C2C1)C1=CC=C(C=C1)F)NC(C)=O PPZJZRLLRBFSTD-UHFFFAOYSA-N 0.000 claims 1
- XGTWNOWHSZYLIV-UHFFFAOYSA-N N-[6-cyano-4-(4-fluorophenyl)-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-yl]acetamide Chemical compound C(#N)N1CC=2N=C(N=C(C=2C1)C1=CC=C(C=C1)F)NC(C)=O XGTWNOWHSZYLIV-UHFFFAOYSA-N 0.000 claims 1
- QFXNCPIXTASELR-UHFFFAOYSA-N N-[6-cyano-4-[3-(methanesulfonamido)phenyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-yl]acetamide Chemical compound C(#N)N1CC=2N=C(N=C(C=2C1)C1=CC(=CC=C1)NS(=O)(=O)C)NC(C)=O QFXNCPIXTASELR-UHFFFAOYSA-N 0.000 claims 1
- MKBJOEDEEMQSDO-UHFFFAOYSA-N N-[6-cyano-4-[3-(trifluoromethoxy)phenyl]-5,7-dihydropyrrolo[3,4-d]pyrimidin-2-yl]acetamide Chemical compound C(#N)N1CC=2N=C(N=C(C=2C1)C1=CC(=CC=C1)OC(F)(F)F)NC(C)=O MKBJOEDEEMQSDO-UHFFFAOYSA-N 0.000 claims 1
- SZUFLTMIOBNMIE-UHFFFAOYSA-N N-[7-(2-carbamoylphenyl)-2-cyano-1,3-dihydroisoindol-5-yl]-1-methylpiperidine-3-carboxamide Chemical compound C(N)(=O)C1=C(C=CC=C1)C=1C=C(C=C2CN(CC=12)C#N)NC(=O)C1CN(CCC1)C SZUFLTMIOBNMIE-UHFFFAOYSA-N 0.000 claims 1
- LVKUOQXCCVSBCT-UHFFFAOYSA-N N-[[2-cyano-7-(2,4-dicyanophenyl)-1,3-dihydroisoindol-5-yl]methyl]acetamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)CNC(C)=O)C1=C(C=C(C=C1)C#N)C#N LVKUOQXCCVSBCT-UHFFFAOYSA-N 0.000 claims 1
- PNBLIZIEWITNDM-UHFFFAOYSA-N N-[[2-cyano-7-(2-cyanophenyl)-1,3-dihydroisoindol-5-yl]methyl]acetamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)CNC(C)=O)C1=C(C=CC=C1)C#N PNBLIZIEWITNDM-UHFFFAOYSA-N 0.000 claims 1
- KMNBZOGKVGSURK-UHFFFAOYSA-N N-[[2-cyano-7-(4-cyanophenyl)-1,3-dihydroisoindol-5-yl]methyl]-1,1-dioxothiane-4-carboxamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)CNC(=O)C1CCS(CC1)(=O)=O)C1=CC=C(C=C1)C#N KMNBZOGKVGSURK-UHFFFAOYSA-N 0.000 claims 1
- YPOIFCTYTJXHFX-UHFFFAOYSA-N N-[[2-cyano-7-(4-cyanophenyl)-1,3-dihydroisoindol-5-yl]methyl]-1-methylpyrazole-4-carboxamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)CNC(=O)C=1C=NN(C=1)C)C1=CC=C(C=C1)C#N YPOIFCTYTJXHFX-UHFFFAOYSA-N 0.000 claims 1
- IFCWOXKOULQEBY-UHFFFAOYSA-N N-[[2-cyano-7-(4-cyanophenyl)-1,3-dihydroisoindol-5-yl]methyl]-N-methylacetamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)CN(C(C)=O)C)C1=CC=C(C=C1)C#N IFCWOXKOULQEBY-UHFFFAOYSA-N 0.000 claims 1
- VZZQEAXKNWWVRC-UHFFFAOYSA-N N-[[2-cyano-7-(4-cyanophenyl)-1,3-dihydroisoindol-5-yl]methyl]acetamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)CNC(C)=O)C1=CC=C(C=C1)C#N VZZQEAXKNWWVRC-UHFFFAOYSA-N 0.000 claims 1
- RXDIVXGAOSCQNQ-UHFFFAOYSA-N N-[[2-cyano-7-(4-cyanophenyl)-1,3-dihydroisoindol-5-yl]methyl]methanesulfonamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)CNS(=O)(=O)C)C1=CC=C(C=C1)C#N RXDIVXGAOSCQNQ-UHFFFAOYSA-N 0.000 claims 1
- QJYWFRAIENJBOK-UHFFFAOYSA-N N-[[2-cyano-7-(4-cyanophenyl)-1,3-dihydroisoindol-5-yl]methyl]oxane-4-carboxamide Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)CNC(=O)C1CCOCC1)C1=CC=C(C=C1)C#N QJYWFRAIENJBOK-UHFFFAOYSA-N 0.000 claims 1
- OCDYCWSUAITKPK-UHFFFAOYSA-N N-benzyl-2-cyano-1,3-dihydroisoindole-4-carboxamide Chemical compound C(C1=CC=CC=C1)NC(=O)C=1C=2CN(CC=2C=CC=1)C#N OCDYCWSUAITKPK-UHFFFAOYSA-N 0.000 claims 1
- IABYCGGNTGACQH-UHFFFAOYSA-N N1=CC(=CC=C1)C=1N=C(C2=C(N=1)CN(C2)C#N)N1CCCC1 Chemical compound N1=CC(=CC=C1)C=1N=C(C2=C(N=1)CN(C2)C#N)N1CCCC1 IABYCGGNTGACQH-UHFFFAOYSA-N 0.000 claims 1
- 206010029260 Neuroblastoma Diseases 0.000 claims 1
- ANNDDOWWBSGNQO-UHFFFAOYSA-N O=C(NC1=CC=CC2=C1CN(C2)C#N)C1=CN(CC2=CC=CC=C2)C(=O)C=C1 Chemical compound O=C(NC1=CC=CC2=C1CN(C2)C#N)C1=CN(CC2=CC=CC=C2)C(=O)C=C1 ANNDDOWWBSGNQO-UHFFFAOYSA-N 0.000 claims 1
- 206010030155 Oesophageal carcinoma Diseases 0.000 claims 1
- 102100035196 POLG alternative reading frame Human genes 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 208000013234 Pearson syndrome Diseases 0.000 claims 1
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 1
- 208000002009 Pyruvate Dehydrogenase Complex Deficiency Disease Diseases 0.000 claims 1
- 208000021886 Pyruvate carboxylase deficiency Diseases 0.000 claims 1
- 208000007014 Retinitis pigmentosa Diseases 0.000 claims 1
- 208000021712 Soft tissue sarcoma Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 210000000601 blood cell Anatomy 0.000 claims 1
- 210000000988 bone and bone Anatomy 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 210000000481 breast Anatomy 0.000 claims 1
- GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 201000008609 cerebral creatine deficiency syndrome Diseases 0.000 claims 1
- 210000001072 colon Anatomy 0.000 claims 1
- 125000002993 cycloalkylene group Chemical group 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 208000033679 diabetic kidney disease Diseases 0.000 claims 1
- 125000004639 dihydroindenyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 1
- 125000005045 dihydroisoquinolinyl group Chemical group C1(NC=CC2=CC=CC=C12)* 0.000 claims 1
- 125000005046 dihydronaphthyl group Chemical group 0.000 claims 1
- 125000004655 dihydropyridinyl group Chemical group N1(CC=CC=C1)* 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 201000009028 early myoclonic encephalopathy Diseases 0.000 claims 1
- 201000004101 esophageal cancer Diseases 0.000 claims 1
- 210000002950 fibroblast Anatomy 0.000 claims 1
- 230000004761 fibrosis Effects 0.000 claims 1
- 210000003128 head Anatomy 0.000 claims 1
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims 1
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims 1
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 206010024627 liposarcoma Diseases 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 230000008774 maternal effect Effects 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 208000030159 metabolic disease Diseases 0.000 claims 1
- NSNSQLCLEREDML-UHFFFAOYSA-N methyl 2-cyano-7-phenyl-1,3-dihydroisoindole-5-carboxylate Chemical compound C(#N)N1CC2=C(C=C(C=C2C1)C(=O)OC)C1=CC=CC=C1 NSNSQLCLEREDML-UHFFFAOYSA-N 0.000 claims 1
- 201000002697 mitochondrial DNA depletion syndrome Diseases 0.000 claims 1
- 230000004065 mitochondrial dysfunction Effects 0.000 claims 1
- 230000002438 mitochondrial effect Effects 0.000 claims 1
- 230000035772 mutation Effects 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 208000031225 myocardial ischemia Diseases 0.000 claims 1
- 210000003739 neck Anatomy 0.000 claims 1
- 201000001119 neuropathy Diseases 0.000 claims 1
- 230000007823 neuropathy Effects 0.000 claims 1
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 1
- 108010007425 oligomycin sensitivity conferring protein Proteins 0.000 claims 1
- 210000000056 organ Anatomy 0.000 claims 1
- 201000008968 osteosarcoma Diseases 0.000 claims 1
- 210000001672 ovary Anatomy 0.000 claims 1
- 125000000160 oxazolidinyl group Chemical group 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 210000000496 pancreas Anatomy 0.000 claims 1
- 208000033808 peripheral neuropathy Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 210000002307 prostate Anatomy 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 201000006473 pyruvate decarboxylase deficiency Diseases 0.000 claims 1
- 208000015445 pyruvate dehydrogenase deficiency Diseases 0.000 claims 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 210000002784 stomach Anatomy 0.000 claims 1
- 210000001550 testis Anatomy 0.000 claims 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 1
- 210000001519 tissue Anatomy 0.000 claims 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1604647.6 | 2016-03-18 | ||
| GBGB1604647.6A GB201604647D0 (en) | 2016-03-18 | 2016-03-18 | Novel compounds |
| PCT/GB2017/050763 WO2017158388A1 (en) | 2016-03-18 | 2017-03-17 | 2-cyanoisoindoline derivatives for treating cancer |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019508467A JP2019508467A (ja) | 2019-03-28 |
| JP2019508467A5 true JP2019508467A5 (cg-RX-API-DMAC7.html) | 2020-03-05 |
| JP6959250B2 JP6959250B2 (ja) | 2021-11-02 |
Family
ID=55968548
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018548744A Active JP6959250B2 (ja) | 2016-03-18 | 2017-03-17 | 癌治療用の２−シアノイソインドリン誘導体 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US10683269B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP3429994B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP6959250B2 (cg-RX-API-DMAC7.html) |
| CN (1) | CN108698992B (cg-RX-API-DMAC7.html) |
| GB (1) | GB201604647D0 (cg-RX-API-DMAC7.html) |
| MA (1) | MA43746A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2017158388A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6708661B2 (ja) | 2015-03-30 | 2020-06-10 | 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１−シアノ−ピロリジン化合物 |
| EP3800186B1 (en) | 2015-07-14 | 2024-10-02 | 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 |
| GB201522768D0 (en) | 2015-12-23 | 2016-02-03 | Mission Therapeutics Ltd | Novel compounds |
| GB201602854D0 (en) | 2016-02-18 | 2016-04-06 | Mission Therapeutics Ltd | Novel compounds |
| 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 |
| JP6959252B2 (ja) | 2016-03-24 | 2021-11-02 | ミッション セラピューティクス リミティド | Ｄｕｂ阻害剤としての１−シアノピロリジン誘導体 |
| 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 |
| GB201617758D0 (en) | 2016-10-20 | 2016-12-07 | Almac Discovery Limited | Pharmaceutical compounds |
| BR112019019555A2 (pt) | 2017-03-30 | 2020-04-22 | Hoffmann La Roche | composto de fórmula i, composição farmacêutica, método de inibição de hpk1, método para melhorar uma resposta imune, método para tratar um distúrbio e uso do composto |
| GB201708652D0 (en) | 2017-05-31 | 2017-07-12 | Mission Therapeutics Ltd | Novel compounds and uses |
| EP3642196B1 (en) | 2017-06-20 | 2022-08-17 | Mission Therapeutics Limited | Substituted cyanopyrrolidines with activity as dub inhibitors |
| KR102717600B1 (ko) | 2017-10-06 | 2024-10-15 | 포르마 세라퓨틱스 인크. | 유비퀴틴 특이적 펩티다제 30의 억제 |
| CA3098628A1 (en) | 2018-05-17 | 2019-11-21 | Forma Therapeutics, Inc. | Fused bicyclic compounds useful as ubiquitin-specific peptidase 30 inhibitors |
| CN112601584A (zh) | 2018-07-24 | 2021-04-02 | 豪夫迈·罗氏有限公司 | 异喹啉化合物及其用途 |
| WO2020036940A1 (en) | 2018-08-14 | 2020-02-20 | 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 |
| PT3860989T (pt) | 2018-10-05 | 2023-06-30 | Forma Therapeutics Inc | Pirrolinas fundidas que atuam como inibidores da protease 30 específica da ubiquitina (usp30) |
| 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 |
| WO2020132561A1 (en) | 2018-12-20 | 2020-06-25 | C4 Therapeutics, Inc. | Targeted protein degradation |
| WO2020139916A1 (en) * | 2018-12-26 | 2020-07-02 | Forma Therapeutics, Inc. | Inhibiting ubiquitin specific peptidase 9x |
| GB201905371D0 (en) | 2019-04-16 | 2019-05-29 | Mission Therapeutics Ltd | Novel compounds |
| GB201905375D0 (en) | 2019-04-16 | 2019-05-29 | Mission Therapeutics Ltd | Novel compounds |
| CN114258392A (zh) * | 2019-08-21 | 2022-03-29 | 卡尔维斯塔制药有限公司 | 酶抑制剂 |
| 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 |
| WO2021204856A1 (en) | 2020-04-08 | 2021-10-14 | Mission Therapeutics Limited | N-cyanopyrrolidines with activity as usp30 inhibitors |
| MX2022014429A (es) | 2020-05-28 | 2022-12-07 | Mission Therapeutics Ltd | N-cianopirrolidinas con actividad como inhibidores de usp30. |
| US20230303547A1 (en) | 2020-06-04 | 2023-09-28 | Mission Therapeutics Limited | N-cyanopyrrolidines with activity as usp30 inhibitors |
| SMT202500343T1 (it) | 2020-06-08 | 2025-11-10 | Mission Therapeutics Ltd | 1-(5-(2-cianopiridin-4-il)ossazol-2-carbonil)-4-metilesaidropirrolo[3,4-b]pirrol-5(1h)-carbonitrile come inibitore di usp30 per l’uso nel trattamento di disfunzione mitocondriale, cancro e fibrosi |
| 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 |
| EP4271383A4 (en) * | 2020-12-29 | 2024-10-23 | Merck Sharp & Dohme LLC | Amido-substituted pyridyl compounds and methods of use thereof for the treatment of herpesviruses |
| US20240409536A1 (en) * | 2021-08-30 | 2024-12-12 | Remix Therapeutics Inc. | Compounds and methods for modulating splicing |
| 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 |
| CA3240377A1 (en) * | 2021-12-08 | 2023-06-15 | Gnanasambandam Kumaravel | Bicyclic heteroarenes and methods of their use |
| GB202200753D0 (en) | 2022-01-21 | 2022-03-09 | Almac Discovery Ltd | Pharmaceutical compounds |
| AR128432A1 (es) * | 2022-02-02 | 2024-05-08 | The Katholieke Univ Leuven | Tetrahidropiridopirimidinas y análogos relacionados para la inhibición de yap / taz-tead |
| WO2025067111A1 (zh) * | 2023-09-27 | 2025-04-03 | 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 |
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 |
| AU2001256981A1 (en) | 2000-04-06 | 2001-10-23 | Axys Pharmaceuticals, Inc. | Cathepsin cysteine protease inhibitors |
| CA2422367C (en) * | 2000-09-15 | 2010-05-18 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| WO2002088079A2 (en) | 2001-05-01 | 2002-11-07 | Bristol-Myers Squibb Company | Dual inhibitors of pde 7 and pde 4 |
| US7105667B2 (en) | 2001-05-01 | 2006-09-12 | Bristol-Myers Squibb Co. | Fused heterocyclic compounds and use thereof |
| US7521557B2 (en) | 2005-05-20 | 2009-04-21 | Bristol-Myers Squibb Company | Pyrrolopyridine-based inhibitors of dipeptidyl peptidase IV and methods |
| JP2009535393A (ja) | 2006-05-01 | 2009-10-01 | ファイザー・プロダクツ・インク | 置換２−アミノ縮合複素環式化合物 |
| CN103261169A (zh) * | 2010-09-24 | 2013-08-21 | 密歇根大学董事会 | 脱泛素酶抑制剂及其应用方法 |
| CA2827072C (en) | 2011-02-25 | 2019-01-08 | Yuhan Corporation | Diaminopyrimidine derivatives and processes for the preparation thereof |
| EP2565186A1 (en) | 2011-09-02 | 2013-03-06 | Hybrigenics S.A. | Selective and reversible inhibitors of ubiquitin specific protease 7 |
| HK1199249A1 (en) | 2011-09-30 | 2015-06-26 | 山东轩竹医药科技有限公司 | Oxazolidinone antibiotics containing fused ring |
| US9802904B2 (en) * | 2012-12-28 | 2017-10-31 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Inhibitors of the USP1/UAF1 deubiquitinase complex and uses thereof |
| CN106458914B (zh) | 2014-03-28 | 2020-01-14 | 常州捷凯医药科技有限公司 | 作为axl抑制剂的杂环化合物 |
| ES2667793T3 (es) | 2014-07-08 | 2018-05-14 | Viiv Healthcare Uk Limited | Derivados de isoindolina para su uso en el tratamiento de una infección vírica |
| GB201416754D0 (en) | 2014-09-23 | 2014-11-05 | Mission Therapeutics Ltd | Novel compounds |
| JP6708661B2 (ja) | 2015-03-30 | 2020-06-10 | 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１−シアノ−ピロリジン化合物 |
| EP3800186B1 (en) | 2015-07-14 | 2024-10-02 | 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 |
| GB201522768D0 (en) | 2015-12-23 | 2016-02-03 | Mission Therapeutics Ltd | Novel compounds |
| GB201602854D0 (en) | 2016-02-18 | 2016-04-06 | Mission Therapeutics Ltd | Novel compounds |
| 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 |
| JP6959252B2 (ja) | 2016-03-24 | 2021-11-02 | ミッション セラピューティクス リミティド | Ｄｕｂ阻害剤としての１−シアノピロリジン誘導体 |
| 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 |
-
2016
- 2016-03-18 GB GBGB1604647.6A patent/GB201604647D0/en not_active Ceased
-
2017
- 2017-03-17 US US16/080,506 patent/US10683269B2/en active Active
- 2017-03-17 EP EP17713408.7A patent/EP3429994B1/en active Active
- 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 CN CN201780009130.3A patent/CN108698992B/zh active Active
- 2017-03-17 JP JP2018548744A patent/JP6959250B2/ja active Active