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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| LT3277677T (lt) | 2015-03-30 | 2021-05-25 | Mission Therapeutics Limited | 1-ciano-pirolidino junginiai kaip usp30 inhibitoriai |
| EP3322702B1 (en) | 2015-07-14 | 2019-11-20 | 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 |
| MA43753A (fr) | 2016-03-24 | 2018-11-28 | Mission Therapeutics Ltd | Dérivés 1-cyano-pyrrolidine comme inhibiteurs de dbu |
| ES2850349T3 (es) | 2016-09-27 | 2021-08-27 | Mission Therapeutics Ltd | Derivados de cianopirrolidina con actividad como inhibidores de 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 WO PCT/GB2017/050763 patent/WO2017158388A1/en not_active Ceased
- 2017-03-17 EP EP17713408.7A patent/EP3429994B1/en active Active
- 2017-03-17 MA MA043746A patent/MA43746A/fr unknown
- 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