JP2019513135A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2019513135A5 JP2019513135A5 JP2018549534A JP2018549534A JP2019513135A5 JP 2019513135 A5 JP2019513135 A5 JP 2019513135A5 JP 2018549534 A JP2018549534 A JP 2018549534A JP 2018549534 A JP2018549534 A JP 2018549534A JP 2019513135 A5 JP2019513135 A5 JP 2019513135A5
- Authority
- JP
- Japan
- Prior art keywords
- carbonitrile
- pyrrolidine
- oxadiazol
- pyrazol
- phenyl
- 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 substituted Chemical class 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 18
- 125000002947 alkylene group Chemical group 0.000 claims 14
- 125000001424 substituent group Chemical group 0.000 claims 11
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 9
- 230000007812 deficiency Effects 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 206010028980 Neoplasm Diseases 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 201000011510 cancer Diseases 0.000 claims 6
- 125000002950 monocyclic group Chemical group 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 125000004450 alkenylene group Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 230000035772 mutation Effects 0.000 claims 4
- 208000011580 syndromic disease Diseases 0.000 claims 4
- YCEVPXOKNUYKTJ-OXQOHEQNSA-N (3S,4S)-3-ethyl-4-[3-(3-phenylphenyl)-1H-pyrazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC(=CC=C1)C1=NNC(=C1)[C@@H]1CN(C[C@H]1CC)C#N)C1=CC=CC=C1 YCEVPXOKNUYKTJ-OXQOHEQNSA-N 0.000 claims 3
- QKAGGRQPMQPZML-RDTXWAMCSA-N (3S,4S)-3-methyl-4-[3-(3-phenylphenyl)-1H-1,2,4-triazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC(=CC=C1)C1=NNC(=N1)[C@@H]1CN(C[C@H]1C)C#N)C1=CC=CC=C1 QKAGGRQPMQPZML-RDTXWAMCSA-N 0.000 claims 3
- GQOVQYRSSCXBDH-DNVCBOLYSA-N (3S,4S)-3-methyl-4-[3-(3-phenylphenyl)-1H-pyrazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC(=CC=C1)C1=NNC(=C1)[C@@H]1CN(C[C@H]1C)C#N)C1=CC=CC=C1 GQOVQYRSSCXBDH-DNVCBOLYSA-N 0.000 claims 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 3
- BDDJHOCILHFVOO-UHFFFAOYSA-N 3-[2-(1-cyanopyrrolidin-3-yl)-1H-imidazo[4,5-b]pyridin-6-yl]-N-methylbenzamide Chemical compound C(#N)N1CC(CC1)C1=NC=2C(=NC=C(C=2)C=2C=C(C(=O)NC)C=CC=2)N1 BDDJHOCILHFVOO-UHFFFAOYSA-N 0.000 claims 3
- VGFNVTAKVLKCQJ-UHFFFAOYSA-N 3-[6-(4-cyanophenyl)-1H-imidazo[4,5-b]pyridin-2-yl]pyrrolidine-1-carbonitrile Chemical compound C(#N)C1=CC=C(C=C1)C=1C=C2C(=NC=1)NC(=N2)C1CN(CC1)C#N VGFNVTAKVLKCQJ-UHFFFAOYSA-N 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 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
- 208000018737 Parkinson disease Diseases 0.000 claims 3
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 150000003573 thiols Chemical class 0.000 claims 3
- UYRLCNCVEQTHLX-RDTXWAMCSA-N (3S,4S)-3-[4-fluoro-3-(3-phenylphenyl)-1H-pyrazol-5-yl]-4-methylpyrrolidine-1-carbonitrile Chemical class C1(=CC(=CC=C1)C1=NNC(=C1F)[C@@H]1CN(C[C@H]1C)C#N)C1=CC=CC=C1 UYRLCNCVEQTHLX-RDTXWAMCSA-N 0.000 claims 2
- QDDHIPRKFHORTO-IUODEOHRSA-N (3S,4S)-3-methyl-4-(6-phenyl-1H-imidazo[4,5-b]pyridin-2-yl)pyrrolidine-1-carbonitrile Chemical class C[C@@H]1CN(C[C@H]1C1=NC=2C(=NC=C(C=2)C2=CC=CC=C2)N1)C#N QDDHIPRKFHORTO-IUODEOHRSA-N 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- OOGIGMNUOCOQKW-UHFFFAOYSA-N 3-[3-(3-phenylphenyl)-1,2-oxazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC(=CC=C1)C1=NOC(=C1)C1CN(CC1)C#N)C1=CC=CC=C1 OOGIGMNUOCOQKW-UHFFFAOYSA-N 0.000 claims 2
- DQDDVPDBFCCEAT-UHFFFAOYSA-N 3-[3-(6-phenylpyridin-2-yl)-1H-pyrazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC=CC=C1)C1=CC=CC(=N1)C1=CC(=NN1)C1CN(CC1)C#N DQDDVPDBFCCEAT-UHFFFAOYSA-N 0.000 claims 2
- 208000014644 Brain disease Diseases 0.000 claims 2
- 206010058892 Carnitine deficiency Diseases 0.000 claims 2
- 201000000915 Chronic Progressive External Ophthalmoplegia 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
- 101000619542 Homo sapiens E3 ubiquitin-protein ligase parkin Proteins 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- 201000000639 Leber hereditary optic neuropathy Diseases 0.000 claims 2
- 108700006159 Long-chain acyl-CoA dehydrogenase deficiency Proteins 0.000 claims 2
- 108700000232 Medium 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
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims 2
- 208000023692 inborn mitochondrial myopathy Diseases 0.000 claims 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- 208000006443 lactic acidosis Diseases 0.000 claims 2
- 208000004687 long chain acyl-CoA dehydrogenase deficiency Diseases 0.000 claims 2
- 208000005548 medium chain acyl-CoA dehydrogenase deficiency Diseases 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical group O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 102000004169 proteins and genes Human genes 0.000 claims 2
- 108090000623 proteins and genes Proteins 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- QJRYYOWARFCJQZ-UHFFFAOYSA-N pyrrolidine-1-carbonitrile Chemical compound N#CN1CCCC1 QJRYYOWARFCJQZ-UHFFFAOYSA-N 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 208000016505 systemic primary carnitine deficiency disease Diseases 0.000 claims 2
- 238000002560 therapeutic procedure Methods 0.000 claims 2
- LWDQOJXOXKXCPG-SFHVURJKSA-N (2S)-2-(1-methyl-5-phenylbenzimidazol-2-yl)pyrrolidine-1-carbonitrile Chemical compound CN1C(=NC2=C1C=CC(=C2)C1=CC=CC=C1)[C@H]1N(CCC1)C#N LWDQOJXOXKXCPG-SFHVURJKSA-N 0.000 claims 1
- QLZCRJOFZWTDFJ-KRWDZBQOSA-N (2S)-2-(6-phenyl-1H-benzimidazol-2-yl)pyrrolidine-1-carbonitrile Chemical compound C1(=CC=CC=C1)C=1C=CC2=C(NC(=N2)[C@H]2N(CCC2)C#N)C=1 QLZCRJOFZWTDFJ-KRWDZBQOSA-N 0.000 claims 1
- UFTMGKKZBDRMTN-KRWDZBQOSA-N (2S)-2-[3-(3-phenylphenyl)-1,2,4-oxadiazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC(=CC=C1)C1=NOC(=N1)[C@H]1N(CCC1)C#N)C1=CC=CC=C1 UFTMGKKZBDRMTN-KRWDZBQOSA-N 0.000 claims 1
- HHRVOAKBWBDJER-SFHVURJKSA-N (2S)-2-[5-(1-methylindazol-5-yl)-1,3-benzoxazol-2-yl]pyrrolidine-1-carbonitrile Chemical compound CN1N=CC2=CC(=CC=C12)C=1C=CC2=C(N=C(O2)[C@H]2N(CCC2)C#N)C=1 HHRVOAKBWBDJER-SFHVURJKSA-N 0.000 claims 1
- LKXYJLNDHZNXLE-INIZCTEOSA-N (2S)-2-[5-(3-cyano-2-fluorophenyl)-1,3-benzoxazol-2-yl]pyrrolidine-1-carbonitrile Chemical compound C(#N)C=1C(=C(C=CC=1)C=1C=CC2=C(N=C(O2)[C@H]2N(CCC2)C#N)C=1)F LKXYJLNDHZNXLE-INIZCTEOSA-N 0.000 claims 1
- NJEIYSNAEOYJRQ-KRWDZBQOSA-N (2S)-2-[5-(3-cyano-5-fluorophenyl)-1,3-benzoxazol-2-yl]pyrrolidine-1-carbonitrile Chemical compound C(#N)C=1C=C(C=C(C=1)F)C=1C=CC2=C(N=C(O2)[C@H]2N(CCC2)C#N)C=1 NJEIYSNAEOYJRQ-KRWDZBQOSA-N 0.000 claims 1
- WPUYNEVDNWXWTD-KRWDZBQOSA-N (2S)-2-[5-(3-cyanophenyl)-1,3-benzoxazol-2-yl]pyrrolidine-1-carbonitrile Chemical compound C(#N)C=1C=C(C=CC=1)C=1C=CC2=C(N=C(O2)[C@H]2N(CCC2)C#N)C=1 WPUYNEVDNWXWTD-KRWDZBQOSA-N 0.000 claims 1
- GXJJANNHRIQFAE-SFHVURJKSA-N (2S)-2-[5-(3-ethylphenyl)-1,3-benzoxazol-2-yl]pyrrolidine-1-carbonitrile Chemical compound C(C)C=1C=C(C=CC=1)C=1C=CC2=C(N=C(O2)[C@H]2N(CCC2)C#N)C=1 GXJJANNHRIQFAE-SFHVURJKSA-N 0.000 claims 1
- NIIOHRRQFFQCRD-SFHVURJKSA-N (2S)-2-[5-(3-methyl-2H-indazol-6-yl)-1,3-benzoxazol-2-yl]pyrrolidine-1-carbonitrile Chemical compound CC1=NNC2=CC(=CC=C12)C=1C=CC2=C(N=C(O2)[C@H]2N(CCC2)C#N)C=1 NIIOHRRQFFQCRD-SFHVURJKSA-N 0.000 claims 1
- UNCUIPWWNIWZAQ-INIZCTEOSA-N (2S)-2-[5-(3-nitrophenyl)-1,3-benzoxazol-2-yl]pyrrolidine-1-carbonitrile Chemical compound [N+](=O)([O-])C=1C=C(C=CC=1)C=1C=CC2=C(N=C(O2)[C@H]2N(CCC2)C#N)C=1 UNCUIPWWNIWZAQ-INIZCTEOSA-N 0.000 claims 1
- DGABTZKIJGWJMI-INIZCTEOSA-N (2S)-2-[5-(7-cyanonaphthalen-2-yl)-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound N#CN1CCC[C@H]1C1=NOC(=N1)C1=CC2=CC(=CC=C2C=C1)C#N DGABTZKIJGWJMI-INIZCTEOSA-N 0.000 claims 1
- DXJFNBXEXCOKRM-KRWDZBQOSA-N (2S)-2-[5-[2-(3-cyanophenyl)pyridin-4-yl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound C(#N)C=1C=C(C=CC=1)C1=NC=CC(=C1)C1=NC(=NO1)[C@H]1N(CCC1)C#N DXJFNBXEXCOKRM-KRWDZBQOSA-N 0.000 claims 1
- ALZZAACJVPZYJL-HNNXBMFYSA-N (2S)-2-[5-[2-(3-cyanophenyl)pyrimidin-4-yl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound C(#N)C=1C=C(C=CC=1)C1=NC=CC(=N1)C1=NC(=NO1)[C@H]1N(CCC1)C#N ALZZAACJVPZYJL-HNNXBMFYSA-N 0.000 claims 1
- KVKYPPQEVRDEQR-KRWDZBQOSA-N (2S)-2-[5-[2-(4-cyanophenyl)pyridin-4-yl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound N#CN1CCC[C@H]1C1=NOC(=N1)C1=CC(=NC=C1)C1=CC=C(C=C1)C#N KVKYPPQEVRDEQR-KRWDZBQOSA-N 0.000 claims 1
- JJXCPKJWYFFNTK-HNNXBMFYSA-N (2S)-2-[5-[2-(4-cyanophenyl)pyrimidin-4-yl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound C(#N)C1=CC=C(C=C1)C1=NC=CC(=N1)C1=NC(=NO1)[C@H]1N(CCC1)C#N JJXCPKJWYFFNTK-HNNXBMFYSA-N 0.000 claims 1
- OOBIYFPSRDWNLP-SFHVURJKSA-N (2S)-2-[5-[3-(4-cyanophenyl)phenyl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound C(#N)C1=CC=C(C=C1)C1=CC(=CC=C1)C1=NC(=NO1)[C@H]1N(CCC1)C#N OOBIYFPSRDWNLP-SFHVURJKSA-N 0.000 claims 1
- IXTPWOROFKKPMY-INIZCTEOSA-N (2S)-2-[5-[3-(trifluoromethoxy)phenyl]-1,3-benzoxazol-2-yl]pyrrolidine-1-carbonitrile Chemical compound FC(OC=1C=C(C=CC=1)C=1C=CC2=C(N=C(O2)[C@H]2N(CCC2)C#N)C=1)(F)F IXTPWOROFKKPMY-INIZCTEOSA-N 0.000 claims 1
- YSZRQYJFWPCFHU-KRWDZBQOSA-N (2S)-2-[5-[4-(4-cyanophenyl)pyridin-2-yl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound N#CN1CCC[C@H]1C1=NOC(=N1)C1=NC=CC(=C1)C1=CC=C(C=C1)C#N YSZRQYJFWPCFHU-KRWDZBQOSA-N 0.000 claims 1
- UVWPANKONCESSM-KRWDZBQOSA-N (2S)-2-[5-[6-(4-cyanophenyl)pyridin-2-yl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound N#CN1CCC[C@H]1C1=NOC(=N1)C1=NC(=CC=C1)C1=CC=C(C=C1)C#N UVWPANKONCESSM-KRWDZBQOSA-N 0.000 claims 1
- VYIKGLLFCLBIHZ-KRWDZBQOSA-N (2S)-2-[6-(3-cyanophenyl)-1,3-benzoxazol-2-yl]pyrrolidine-1-carbonitrile Chemical compound C(#N)C=1C=C(C=CC=1)C1=CC2=C(N=C(O2)[C@H]2N(CCC2)C#N)C=C1 VYIKGLLFCLBIHZ-KRWDZBQOSA-N 0.000 claims 1
- YIIWMZZGGXBXGY-SFHVURJKSA-N (2S)-2-[6-(3-ethylphenyl)-1,3-benzoxazol-2-yl]pyrrolidine-1-carbonitrile Chemical compound C(C)C=1C=C(C=CC=1)C1=CC2=C(N=C(O2)[C@H]2N(CCC2)C#N)C=C1 YIIWMZZGGXBXGY-SFHVURJKSA-N 0.000 claims 1
- OIMFBFQKAAYUPW-GFCCVEGCSA-N (3R)-3-(6-pyridin-4-yl-1H-imidazo[4,5-b]pyridin-2-yl)pyrrolidine-1-carbonitrile Chemical compound N1=CC=C(C=C1)C=1C=C2C(=NC=1)NC(=N2)[C@H]1CN(CC1)C#N OIMFBFQKAAYUPW-GFCCVEGCSA-N 0.000 claims 1
- JRMSKUNXCIFTPE-QGZVFWFLSA-N (3R)-3-[4-fluoro-3-(3-phenylphenyl)-1H-pyrazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC(=CC=C1)C1=NNC(=C1F)[C@H]1CN(CC1)C#N)C1=CC=CC=C1 JRMSKUNXCIFTPE-QGZVFWFLSA-N 0.000 claims 1
- VELGHGUUDKIKKG-CYBMUJFWSA-N (3R)-3-[5-(1-pyrimidin-2-ylpiperidin-4-yl)-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound N1=C(N=CC=C1)N1CCC(CC1)C1=NC(=NO1)[C@H]1CN(CC1)C#N VELGHGUUDKIKKG-CYBMUJFWSA-N 0.000 claims 1
- BGPWQYRMQSINJH-OAHLLOKOSA-N (3R)-3-[5-(4-phenylpyridin-2-yl)-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC=CC=C1)C1=CC(=NC=C1)C1=NC(=NO1)[C@H]1CN(CC1)C#N BGPWQYRMQSINJH-OAHLLOKOSA-N 0.000 claims 1
- FGVVVRRGYGYMAD-CYBMUJFWSA-N (3R)-3-[5-[3-methoxy-4-(1-methylpyrazol-4-yl)phenyl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound COC=1C=C(C=CC=1C=1C=NN(C=1)C)C1=NC(=NO1)[C@H]1CN(CC1)C#N FGVVVRRGYGYMAD-CYBMUJFWSA-N 0.000 claims 1
- BHTABZSIMRSZLB-GFCCVEGCSA-N (3R)-3-[5-[4-fluoro-3-(1-methylpyrazol-4-yl)phenyl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound FC1=C(C=C(C=C1)C1=NC(=NO1)[C@H]1CN(CC1)C#N)C=1C=NN(C=1)C BHTABZSIMRSZLB-GFCCVEGCSA-N 0.000 claims 1
- ZMYCCDRPOCQXSU-CYBMUJFWSA-N (3R)-3-[7-(4-methylimidazol-1-yl)-1,6-dioxo-3,4-dihydropyrido[1,2-a]pyrazin-2-yl]pyrrolidine-1-carbonitrile Chemical compound CC=1N=CN(C=1)C1=CC=C2N(CCN(C2=O)[C@H]2CN(CC2)C#N)C1=O ZMYCCDRPOCQXSU-CYBMUJFWSA-N 0.000 claims 1
- QEXNPABWVLISKW-BBRMVZONSA-N (3R,4R)-3-methyl-4-(6-phenyl-1H-benzimidazol-2-yl)pyrrolidine-1-carbonitrile Chemical compound C[C@H]1CN(C[C@@H]1c1nc2ccc(cc2[nH]1)-c1ccccc1)C#N QEXNPABWVLISKW-BBRMVZONSA-N 0.000 claims 1
- OIMFBFQKAAYUPW-LBPRGKRZSA-N (3S)-3-(6-pyridin-4-yl-1H-imidazo[4,5-b]pyridin-2-yl)pyrrolidine-1-carbonitrile Chemical compound N1=CC=C(C=C1)C=1C=C2C(=NC=1)NC(=N2)[C@@H]1CN(CC1)C#N OIMFBFQKAAYUPW-LBPRGKRZSA-N 0.000 claims 1
- JRMSKUNXCIFTPE-KRWDZBQOSA-N (3S)-3-[4-fluoro-3-(3-phenylphenyl)-1H-pyrazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC(=CC=C1)C1=NNC(=C1F)[C@@H]1CN(CC1)C#N)C1=CC=CC=C1 JRMSKUNXCIFTPE-KRWDZBQOSA-N 0.000 claims 1
- PAOJMOJBWAVWJY-LEWJYISDSA-N (3S,4S)-3-cyclopropyl-4-[3-(3-phenylphenyl)-1H-pyrazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC(=CC=C1)C1=NNC(=C1)[C@@H]1CN(C[C@H]1C1CC1)C#N)C1=CC=CC=C1 PAOJMOJBWAVWJY-LEWJYISDSA-N 0.000 claims 1
- NBUVQQFAKIMQHM-ZYHUDNBSSA-N (3S,4S)-3-methyl-4-(3-phenyl-1H-1,2,4-triazol-5-yl)pyrrolidine-1-carbonitrile Chemical compound C[C@@H]1CN(C[C@H]1C1=NC(=NN1)C1=CC=CC=C1)C#N NBUVQQFAKIMQHM-ZYHUDNBSSA-N 0.000 claims 1
- HHDCQGWYINSJKC-DGCLKSJQSA-N (3S,4S)-3-methyl-4-(3-phenyl-1H-pyrazol-5-yl)pyrrolidine-1-carbonitrile Chemical compound C[C@@H]1CN(C[C@H]1C1=CC(=NN1)C1=CC=CC=C1)C#N HHDCQGWYINSJKC-DGCLKSJQSA-N 0.000 claims 1
- GTTHGGZSJLFSSI-ZYHUDNBSSA-N (3S,4S)-3-methyl-4-(3-pyridin-4-yl-1H-pyrazol-5-yl)pyrrolidine-1-carbonitrile Chemical compound C[C@@H]1CN(C[C@H]1C1=CC(=NN1)C1=CC=NC=C1)C#N GTTHGGZSJLFSSI-ZYHUDNBSSA-N 0.000 claims 1
- JPDRDBVNIJVICQ-OXQOHEQNSA-N (3S,4S)-3-methyl-4-[1-methyl-5-(3-phenylphenyl)pyrazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC(=CC=C1)C1=CC(=NN1C)[C@@H]1CN(C[C@H]1C)C#N)C1=CC=CC=C1 JPDRDBVNIJVICQ-OXQOHEQNSA-N 0.000 claims 1
- XQCSLZIIAUBAFM-OXQOHEQNSA-N (3S,4S)-3-methyl-4-[2-methyl-5-(3-phenylphenyl)pyrazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC(=CC=C1)C1=NN(C(=C1)[C@@H]1CN(C[C@H]1C)C#N)C)C1=CC=CC=C1 XQCSLZIIAUBAFM-OXQOHEQNSA-N 0.000 claims 1
- 125000006714 (C3-C10) heterocyclyl group Chemical group 0.000 claims 1
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 1
- SNBQEDCIRRRVNT-HNNXBMFYSA-N 1-[3-[3-[(2S)-1-cyanopyrrolidin-2-yl]-1,2,4-oxadiazol-5-yl]phenyl]pyrazole-4-carbonitrile Chemical compound C(#N)N1[C@@H](CCC1)C1=NOC(=N1)C=1C=C(C=CC=1)N1N=CC(=C1)C#N SNBQEDCIRRRVNT-HNNXBMFYSA-N 0.000 claims 1
- VJXXMRABABKBBD-ZDUSSCGKSA-N 1-[4-[3-[(2S)-1-cyanopyrrolidin-2-yl]-1,2,4-oxadiazol-5-yl]pyridin-2-yl]pyrazole-4-carbonitrile Chemical compound C(#N)N1[C@@H](CCC1)C1=NOC(=N1)C1=CC(=NC=C1)N1N=CC(=C1)C#N VJXXMRABABKBBD-ZDUSSCGKSA-N 0.000 claims 1
- HTDQGHNUTKHUHK-LBPRGKRZSA-N 1-[4-[3-[(2S)-1-cyanopyrrolidin-2-yl]-1,2,4-oxadiazol-5-yl]pyrimidin-2-yl]pyrazole-4-carbonitrile Chemical compound C(#N)N1[C@@H](CCC1)C1=NOC(=N1)C1=NC(=NC=C1)N1N=CC(=C1)C#N HTDQGHNUTKHUHK-LBPRGKRZSA-N 0.000 claims 1
- NBJIMUGWTBUFSM-LBPRGKRZSA-N 1-[6-[3-[(2S)-1-cyanopyrrolidin-2-yl]-1,2,4-oxadiazol-5-yl]pyrazin-2-yl]pyrazole-4-carbonitrile Chemical compound C(#N)N1[C@@H](CCC1)C1=NOC(=N1)C1=CN=CC(=N1)N1N=CC(=C1)C#N NBJIMUGWTBUFSM-LBPRGKRZSA-N 0.000 claims 1
- AWGLCXURYUZDHP-ZDUSSCGKSA-N 1-[6-[3-[(2S)-1-cyanopyrrolidin-2-yl]-1,2,4-oxadiazol-5-yl]pyridin-2-yl]pyrazole-4-carbonitrile Chemical compound C(#N)N1[C@@H](CCC1)C1=NOC(=N1)C1=CC=CC(=N1)N1N=CC(=C1)C#N AWGLCXURYUZDHP-ZDUSSCGKSA-N 0.000 claims 1
- GIOSRQRCYCDNHN-UHFFFAOYSA-N 2-(3-methyl-6-phenylimidazo[4,5-b]pyridin-2-yl)pyrrolidine-1-carbonitrile Chemical compound Cn1c(nc2cc(cnc12)-c1ccccc1)C1CCCN1C#N GIOSRQRCYCDNHN-UHFFFAOYSA-N 0.000 claims 1
- CLSNNZQNSGFJOT-SFHVURJKSA-N 2-[(2S)-1-cyanopyrrolidin-2-yl]-6-(3-ethylphenyl)-N-methyl-1,3-benzoxazole-4-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C=1OC=2C(N=1)=C(C=C(C=2)C1=CC(=CC=C1)CC)C(=O)NC CLSNNZQNSGFJOT-SFHVURJKSA-N 0.000 claims 1
- OTLQYIQZTSCMSJ-INIZCTEOSA-N 2-[(2S)-1-cyanopyrrolidin-2-yl]-N-methyl-6-phenyl-1,3-benzoxazole-4-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C=1OC=2C(N=1)=C(C=C(C=2)C1=CC=CC=C1)C(=O)NC OTLQYIQZTSCMSJ-INIZCTEOSA-N 0.000 claims 1
- WHSFBKILQMOWMY-UHFFFAOYSA-N 2-[3-(5-pyrrolidin-3-yl-1H-pyrazol-3-yl)phenyl]pyridine Chemical compound C1CNCC1C2=CC(=NN2)C3=CC=CC(=C3)C4=CC=CC=N4 WHSFBKILQMOWMY-UHFFFAOYSA-N 0.000 claims 1
- WYJJRHZAARUPOH-UHFFFAOYSA-N 2-[4-[3-(1-cyanopyrrolidin-2-yl)-1,2,4-oxadiazol-5-yl]pyridin-2-yl]pyridine-4-carbonitrile Chemical compound N#CN1CCCC1C1=NOC(=N1)C1=CC(=NC=C1)C1=NC=CC(=C1)C#N WYJJRHZAARUPOH-UHFFFAOYSA-N 0.000 claims 1
- GUNVLXASLNTIFN-UHFFFAOYSA-N 2-[5-(2-phenylpyridin-4-yl)-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC=CC=C1)C1=NC=CC(=C1)C1=NC(=NO1)C1N(CCC1)C#N GUNVLXASLNTIFN-UHFFFAOYSA-N 0.000 claims 1
- KDRNXFOXCIVBST-UHFFFAOYSA-N 2-[5-(3-phenylphenyl)-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC(=CC=C1)C1=NC(=NO1)C1N(CCC1)C#N)C1=CC=CC=C1 KDRNXFOXCIVBST-UHFFFAOYSA-N 0.000 claims 1
- HXKJVARHLIJQHY-UHFFFAOYSA-N 2-[5-(3-phenylphenyl)-1,3,4-oxadiazol-2-yl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC(=CC=C1)C1=NN=C(O1)C1N(CCC1)C#N)C1=CC=CC=C1 HXKJVARHLIJQHY-UHFFFAOYSA-N 0.000 claims 1
- WEWLHBGLMPXEGX-UHFFFAOYSA-N 2-[5-(3-pyridin-3-ylphenyl)-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound N1=CC(=CC=C1)C=1C=C(C=CC=1)C1=NC(=NO1)C1N(CCC1)C#N WEWLHBGLMPXEGX-UHFFFAOYSA-N 0.000 claims 1
- NYOIJLOFNFSZLJ-UHFFFAOYSA-N 2-[5-(3-pyrimidin-5-ylphenyl)-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound N1=CN=CC(=C1)C=1C=C(C=CC=1)C1=NC(=NO1)C1N(CCC1)C#N NYOIJLOFNFSZLJ-UHFFFAOYSA-N 0.000 claims 1
- WJCGDFUCOVFQKB-UHFFFAOYSA-N 2-[5-(4-phenylphenyl)-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound N#CN1CCCC1c1noc(n1)-c1ccc(cc1)-c1ccccc1 WJCGDFUCOVFQKB-UHFFFAOYSA-N 0.000 claims 1
- POJWFUNCHJVWPG-UHFFFAOYSA-N 2-[5-(6-phenylpyridin-2-yl)-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC=CC=C1)C1=CC=CC(=N1)C1=NC(=NO1)C1N(CCC1)C#N POJWFUNCHJVWPG-UHFFFAOYSA-N 0.000 claims 1
- RDAQKAIPPWXIBA-UHFFFAOYSA-N 2-[5-[2-[3-(trifluoromethoxy)phenyl]pyridin-4-yl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound FC(F)(F)OC1=CC=CC(=C1)C1=NC=CC(=C1)C1=NC(=NO1)C1CCCN1C#N RDAQKAIPPWXIBA-UHFFFAOYSA-N 0.000 claims 1
- FOWCMSIGAVFKCR-UHFFFAOYSA-N 2-[5-[2-[3-(trifluoromethoxy)phenyl]pyrimidin-4-yl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound FC(OC=1C=C(C=CC=1)C1=NC=CC(=N1)C1=NC(=NO1)C1N(CCC1)C#N)(F)F FOWCMSIGAVFKCR-UHFFFAOYSA-N 0.000 claims 1
- BNHYLRIEWFIBLI-UHFFFAOYSA-N 2-[5-[2-[4-(trifluoromethoxy)phenyl]pyridin-4-yl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound FC(F)(F)OC1=CC=C(C=C1)C1=NC=CC(=C1)C1=NC(=NO1)C1CCCN1C#N BNHYLRIEWFIBLI-UHFFFAOYSA-N 0.000 claims 1
- FYHHLPHWKBNNHP-UHFFFAOYSA-N 2-[5-[3-(1-methylindazol-5-yl)phenyl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound CN1N=CC2=CC(=CC=C12)C=1C=C(C=CC=1)C1=NC(=NO1)C1N(CCC1)C#N FYHHLPHWKBNNHP-UHFFFAOYSA-N 0.000 claims 1
- KLMARDYXWJOXQN-UHFFFAOYSA-N 2-[5-[3-(1-methylpyrazol-4-yl)phenyl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound CN1N=CC(=C1)C=1C=C(C=CC=1)C1=NC(=NO1)C1N(CCC1)C#N KLMARDYXWJOXQN-UHFFFAOYSA-N 0.000 claims 1
- URIZUZHVQPRXEW-UHFFFAOYSA-N 2-[5-[3-(2-cyanophenyl)phenyl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound C(#N)C1=C(C=CC=C1)C1=CC(=CC=C1)C1=NC(=NO1)C1N(CCC1)C#N URIZUZHVQPRXEW-UHFFFAOYSA-N 0.000 claims 1
- TVIBFPDGGDKDEW-UHFFFAOYSA-N 2-[5-[3-(2-methoxypyridin-3-yl)phenyl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound COC1=NC=CC=C1C=1C=C(C=CC=1)C1=NC(=NO1)C1N(CCC1)C#N TVIBFPDGGDKDEW-UHFFFAOYSA-N 0.000 claims 1
- LKKCKAZGDCLNPJ-UHFFFAOYSA-N 2-[5-[3-(2-methoxypyridin-4-yl)phenyl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound COC1=NC=CC(=C1)C=1C=C(C=CC=1)C1=NC(=NO1)C1N(CCC1)C#N LKKCKAZGDCLNPJ-UHFFFAOYSA-N 0.000 claims 1
- XWYGEAMOWGSDAE-UHFFFAOYSA-N 2-[5-[3-(2-methylpyrazol-3-yl)phenyl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound CN1N=CC=C1C=1C=C(C=CC=1)C1=NC(=NO1)C1N(CCC1)C#N XWYGEAMOWGSDAE-UHFFFAOYSA-N 0.000 claims 1
- NJWQFLSEZDTEID-UHFFFAOYSA-N 2-[5-[3-(3,5-dimethyl-1,2-oxazol-4-yl)phenyl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound CC1=NOC(=C1C=1C=C(C=CC=1)C1=NC(=NO1)C1N(CCC1)C#N)C NJWQFLSEZDTEID-UHFFFAOYSA-N 0.000 claims 1
- VNLICYVGPPXUGA-UHFFFAOYSA-N 2-[5-[3-(3-cyano-2-fluorophenyl)phenyl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound C(#N)C=1C(=C(C=CC=1)C1=CC(=CC=C1)C1=NC(=NO1)C1N(CCC1)C#N)F VNLICYVGPPXUGA-UHFFFAOYSA-N 0.000 claims 1
- NDFRWSFZHWXZPM-UHFFFAOYSA-N 2-[5-[3-(3-cyano-5-fluorophenyl)phenyl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound C(#N)C=1C=C(C=C(C=1)F)C1=CC(=CC=C1)C1=NC(=NO1)C1N(CCC1)C#N NDFRWSFZHWXZPM-UHFFFAOYSA-N 0.000 claims 1
- VLSRMZXXROMHHG-UHFFFAOYSA-N 2-[5-[3-(3-nitrophenyl)phenyl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound [N+](=O)([O-])C=1C=C(C=CC=1)C1=CC(=CC=C1)C1=NC(=NO1)C1N(CCC1)C#N VLSRMZXXROMHHG-UHFFFAOYSA-N 0.000 claims 1
- NIPISVQGSVCDHC-UHFFFAOYSA-N 2-[5-[3-(4-methylsulfonylphenyl)phenyl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound CS(=O)(=O)C1=CC=C(C=C1)C1=CC(=CC=C1)C1=NC(=NO1)C1N(CCC1)C#N NIPISVQGSVCDHC-UHFFFAOYSA-N 0.000 claims 1
- VMNUKTNPDWWZBJ-UHFFFAOYSA-N 2-[5-[3-(4-nitrophenyl)phenyl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)C1=CC(=CC=C1)C1=NC(=NO1)C1N(CCC1)C#N VMNUKTNPDWWZBJ-UHFFFAOYSA-N 0.000 claims 1
- FWTYKFOMHJVQKL-UHFFFAOYSA-N 2-[5-[3-(5-cyano-2-methoxyphenyl)phenyl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound C(#N)C=1C=CC(=C(C=1)C1=CC(=CC=C1)C1=NC(=NO1)C1N(CCC1)C#N)OC FWTYKFOMHJVQKL-UHFFFAOYSA-N 0.000 claims 1
- NSEHBGASSQUWEK-UHFFFAOYSA-N 2-[5-[3-(5-cyanothiophen-2-yl)phenyl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound C(#N)C1=CC=C(S1)C=1C=C(C=CC=1)C1=NC(=NO1)C1N(CCC1)C#N NSEHBGASSQUWEK-UHFFFAOYSA-N 0.000 claims 1
- WJUKTSLHYDYHQU-UHFFFAOYSA-N 2-[5-[3-(5-methylpyridin-3-yl)phenyl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound CC=1C=C(C=NC=1)C=1C=C(C=CC=1)C1=NC(=NO1)C1N(CCC1)C#N WJUKTSLHYDYHQU-UHFFFAOYSA-N 0.000 claims 1
- KTTVAZFTQCZADV-UHFFFAOYSA-N 2-[5-[3-(6-methoxypyridin-3-yl)phenyl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound COC1=CC=C(C=N1)C=1C=C(C=CC=1)C1=NC(=NO1)C1N(CCC1)C#N KTTVAZFTQCZADV-UHFFFAOYSA-N 0.000 claims 1
- WZJWVIQCQYKJRB-UHFFFAOYSA-N 2-[5-[3-(6-methylpyridin-3-yl)phenyl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound CC1=CC=C(C=N1)C=1C=C(C=CC=1)C1=NC(=NO1)C1N(CCC1)C#N WZJWVIQCQYKJRB-UHFFFAOYSA-N 0.000 claims 1
- DSGZGVUZYJEJJZ-UHFFFAOYSA-N 2-[5-[3-(7-methyl-1H-indol-2-yl)phenyl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound CC=1C=CC=C2C=C(NC=12)C=1C=C(C=CC=1)C1=NC(=NO1)C1N(CCC1)C#N DSGZGVUZYJEJJZ-UHFFFAOYSA-N 0.000 claims 1
- QXTYQMBTWZYCLV-UHFFFAOYSA-N 2-[5-[3-(furan-3-yl)phenyl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound O1C=C(C=C1)C=1C=C(C=CC=1)C1=NC(=NO1)C1N(CCC1)C#N QXTYQMBTWZYCLV-UHFFFAOYSA-N 0.000 claims 1
- YOBKOFJNAHPJNR-UHFFFAOYSA-N 2-[5-[4-(3-cyanophenyl)pyridin-2-yl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound C(#N)C=1C=C(C=CC=1)C1=CC(=NC=C1)C1=NC(=NO1)C1N(CCC1)C#N YOBKOFJNAHPJNR-UHFFFAOYSA-N 0.000 claims 1
- NHMUFLBWRNYOIX-UHFFFAOYSA-N 2-[5-[6-(3-cyanophenyl)pyrimidin-4-yl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound C(#N)C=1C=C(C=CC=1)C1=CC(=NC=N1)C1=NC(=NO1)C1N(CCC1)C#N NHMUFLBWRNYOIX-UHFFFAOYSA-N 0.000 claims 1
- XQVBJOPTKZBGKG-UHFFFAOYSA-N 2-methyl-4-[3-(3-phenylphenyl)-1H-pyrazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC(=CC=C1)C1=NNC(=C1)C1CC(N(C1)C#N)C)C1=CC=CC=C1 XQVBJOPTKZBGKG-UHFFFAOYSA-N 0.000 claims 1
- NCONUTKWRFCFSC-UHFFFAOYSA-N 3-(2-amino-3-phenylphenyl)pyrrolidine-1-carbonitrile Chemical compound NC1=C(C=CC=C1C1CN(CC1)C#N)C1=CC=CC=C1 NCONUTKWRFCFSC-UHFFFAOYSA-N 0.000 claims 1
- QMOMMBFKUBZPFA-UHFFFAOYSA-N 3-(3-imidazo[1,2-a]pyridin-6-yl-1H-1,2,4-triazol-5-yl)pyrrolidine-1-carbonitrile Chemical compound N=1C=CN2C=1C=CC(=C2)C=1NC(=NN=1)C1CN(CC1)C#N QMOMMBFKUBZPFA-UHFFFAOYSA-N 0.000 claims 1
- LFNXUMGCLILRQC-UHFFFAOYSA-N 3-(3-naphthalen-2-yl-1H-pyrazol-5-yl)pyrrolidine-1-carbonitrile Chemical compound C1=C(C=CC2=CC=CC=C12)C1=CC(=NN1)C1CN(CC1)C#N LFNXUMGCLILRQC-UHFFFAOYSA-N 0.000 claims 1
- ZPLMBIDASKGLIW-UHFFFAOYSA-N 3-(3-phenyl-1H-1,2,4-triazol-5-yl)pyrrolidine-1-carbonitrile Chemical compound C1(=CC=CC=C1)C=1NC(=NN=1)C1CN(CC1)C#N ZPLMBIDASKGLIW-UHFFFAOYSA-N 0.000 claims 1
- FVBHQAGVSGCNOP-UHFFFAOYSA-N 3-(3-pyridin-2-yl-1H-1,2,4-triazol-5-yl)pyrrolidine-1-carbonitrile Chemical compound N1=C(C=CC=C1)C=1NC(=NN=1)C1CN(CC1)C#N FVBHQAGVSGCNOP-UHFFFAOYSA-N 0.000 claims 1
- OHVVVSYUZCZYPC-UHFFFAOYSA-N 3-(5-methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-yl)pyrrolidine-1-carbonitrile Chemical compound CC1=C(C=C2C(=N1)NC(=N2)C1CN(CC1)C#N)C1=CC=CC=C1 OHVVVSYUZCZYPC-UHFFFAOYSA-N 0.000 claims 1
- ZDSFXSMCMRZSLJ-UHFFFAOYSA-N 3-(5-phenyl-1H-imidazo[4,5-b]pyridin-2-yl)pyrrolidine-1-carbonitrile Chemical compound C1(=CC=CC=C1)C1=CC=C2C(=N1)NC(=N2)C1CN(CC1)C#N ZDSFXSMCMRZSLJ-UHFFFAOYSA-N 0.000 claims 1
- RNDIQVBPGQMVRB-UHFFFAOYSA-N 3-(6-oxo-5-phenyl-1H-pyrimidin-2-yl)pyrrolidine-1-carbonitrile Chemical compound O=C1NC(=NC=C1C1=CC=CC=C1)C1CCN(C1)C#N RNDIQVBPGQMVRB-UHFFFAOYSA-N 0.000 claims 1
- KGYSRZBRDGUVFE-UHFFFAOYSA-N 3-(6-phenyl-1H-benzimidazol-2-yl)pyrrolidine-1-carbonitrile Chemical compound C1(=CC=CC=C1)C1=CC2=C(NC(=N2)C2CN(CC2)C#N)C=C1 KGYSRZBRDGUVFE-UHFFFAOYSA-N 0.000 claims 1
- SGYKLPPZWMAEJV-UHFFFAOYSA-N 3-(6-phenyl-1H-imidazo[4,5-b]pyridin-2-yl)pyrrolidine-1-carbonitrile Chemical compound C1(=CC=CC=C1)C=1C=C2C(=NC=1)NC(=N2)C1CN(CC1)C#N SGYKLPPZWMAEJV-UHFFFAOYSA-N 0.000 claims 1
- OIMFBFQKAAYUPW-UHFFFAOYSA-N 3-(6-pyridin-4-yl-1H-imidazo[4,5-b]pyridin-2-yl)pyrrolidine-1-carbonitrile Chemical compound N1=CC=C(C=C1)C=1C=C2C(=NC=1)NC(=N2)C1CN(CC1)C#N OIMFBFQKAAYUPW-UHFFFAOYSA-N 0.000 claims 1
- MLYURDFKWBUPFY-UHFFFAOYSA-N 3-(7-methyl-6-phenyl-1H-imidazo[4,5-b]pyridin-2-yl)pyrrolidine-1-carbonitrile Chemical compound CC1=C2C(=NC=C1C1=CC=CC=C1)NC(=N2)C1CN(CC1)C#N MLYURDFKWBUPFY-UHFFFAOYSA-N 0.000 claims 1
- GMFRXTVPOSIEBV-UHFFFAOYSA-N 3-(7-phenyl-1H-imidazo[4,5-b]pyridin-2-yl)pyrrolidine-1-carbonitrile Chemical compound C1(=CC=CC=C1)C1=C2C(=NC=C1)NC(=N2)C1CN(CC1)C#N GMFRXTVPOSIEBV-UHFFFAOYSA-N 0.000 claims 1
- XWKJHXLHFFKOHC-UHFFFAOYSA-N 3-(7-phenylimidazo[1,2-a]pyridin-3-yl)pyrrolidine-1-carbonitrile Chemical compound C1(=CC=CC=C1)C1=CC=2N(C=C1)C(=CN=2)C1CN(CC1)C#N XWKJHXLHFFKOHC-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
- MGHVEVJEJKBYJN-UHFFFAOYSA-N 3-[3-(2-methylpyridin-4-yl)-1H-pyrazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound CC1=NC=CC(=C1)C1=NNC(=C1)C1CN(CC1)C#N MGHVEVJEJKBYJN-UHFFFAOYSA-N 0.000 claims 1
- RYEDJJFAUDNRPT-UHFFFAOYSA-N 3-[3-(2-phenylpyridin-4-yl)-1H-1,2,4-triazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC=CC=C1)C1=NC=CC(=C1)C1=NNC(=N1)C1CN(CC1)C#N RYEDJJFAUDNRPT-UHFFFAOYSA-N 0.000 claims 1
- FPTCIFKADJMQBP-UHFFFAOYSA-N 3-[3-(2-phenylpyridin-4-yl)-1H-pyrazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC=CC=C1)C1=NC=CC(=C1)C1=CC(=NN1)C1CN(CC1)C#N FPTCIFKADJMQBP-UHFFFAOYSA-N 0.000 claims 1
- LDRILPCLWUSTBT-UHFFFAOYSA-N 3-[3-(2-pyridin-3-ylpyridin-4-yl)-1H-pyrazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound N1=C(C=C(C=C1)C1=NNC(=C1)C1CN(CC1)C#N)C=1C=NC=CC=1 LDRILPCLWUSTBT-UHFFFAOYSA-N 0.000 claims 1
- YIPIFRQNNQVLJI-UHFFFAOYSA-N 3-[3-(3-cyanophenyl)-1H-pyrazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound C(#N)C=1C=C(C=CC=1)C1=NNC(=C1)C1CN(CC1)C#N YIPIFRQNNQVLJI-UHFFFAOYSA-N 0.000 claims 1
- XGYVTRVLAJCFPT-UHFFFAOYSA-N 3-[3-(3-phenylphenyl)-1H-pyrazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound N#CN1CCC(C1)c1cc(n[nH]1)-c1cccc(c1)-c1ccccc1 XGYVTRVLAJCFPT-UHFFFAOYSA-N 0.000 claims 1
- YJCCDDNGXVAKSD-UHFFFAOYSA-N 3-[3-(3-piperidin-1-ylphenyl)-1H-pyrazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound N1(CCCCC1)C=1C=C(C=CC=1)C1=NNC(=C1)C1CN(CC1)C#N YJCCDDNGXVAKSD-UHFFFAOYSA-N 0.000 claims 1
- IBGYKXQQOFTRIV-UHFFFAOYSA-N 3-[3-(3-pyridin-3-ylphenyl)-1H-pyrazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound N1=CC(=CC=C1)C=1C=C(C=CC=1)C1=NNC(=C1)C1CN(CC1)C#N IBGYKXQQOFTRIV-UHFFFAOYSA-N 0.000 claims 1
- XGELNIZWOFFCOQ-UHFFFAOYSA-N 3-[3-(3-pyridin-4-ylphenyl)-1H-pyrazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound N1=CC=C(C=C1)C=1C=C(C=CC=1)C1=NNC(=C1)C1CN(CC1)C#N XGELNIZWOFFCOQ-UHFFFAOYSA-N 0.000 claims 1
- RYCBJSCDYTZKFX-UHFFFAOYSA-N 3-[3-(3H-benzimidazol-5-yl)-1H-1,2,4-triazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound N1C=NC2=C1C=C(C=C2)C=1NC(=NN=1)C1CN(CC1)C#N RYCBJSCDYTZKFX-UHFFFAOYSA-N 0.000 claims 1
- XCMDIMQMIKBOGS-UHFFFAOYSA-N 3-[3-(4-cyanophenyl)-1H-pyrazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound C(#N)C1=CC=C(C=C1)C1=NNC(=C1)C1CN(CC1)C#N XCMDIMQMIKBOGS-UHFFFAOYSA-N 0.000 claims 1
- NFPLHJBCYHDWSB-UHFFFAOYSA-N 3-[3-(4-phenylphenyl)-1H-1,2,4-triazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC=C(C=C1)C1=NNC(=N1)C1CN(CC1)C#N)C1=CC=CC=C1 NFPLHJBCYHDWSB-UHFFFAOYSA-N 0.000 claims 1
- XWYTYBSTLBOSEI-UHFFFAOYSA-N 3-[3-(4-phenylphenyl)-1H-pyrazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC=C(C=C1)C1=CC(=NN1)C1CN(CC1)C#N)C1=CC=CC=C1 XWYTYBSTLBOSEI-UHFFFAOYSA-N 0.000 claims 1
- RUFAGECJBNBFJT-UHFFFAOYSA-N 3-[3-(4-phenylpyridin-2-yl)-1H-1,2,4-triazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC=CC=C1)C1=CC(=NC=C1)C=1NC(=NN=1)C1CN(CC1)C#N RUFAGECJBNBFJT-UHFFFAOYSA-N 0.000 claims 1
- HFGNAGHYGBCYAY-UHFFFAOYSA-N 3-[3-(4-phenylpyridin-2-yl)-1H-pyrazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC=CC=C1)C1=CC(=NC=C1)C1=CC(=NN1)C1CN(CC1)C#N HFGNAGHYGBCYAY-UHFFFAOYSA-N 0.000 claims 1
- SLRRXLYMWDBYPY-UHFFFAOYSA-N 3-[3-(5-phenylpyridin-2-yl)-1H-pyrazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC=CC=C1)C=1C=CC(=NC=1)C1=CC(=NN1)C1CN(CC1)C#N SLRRXLYMWDBYPY-UHFFFAOYSA-N 0.000 claims 1
- VSIGRWUWVTXGJD-UHFFFAOYSA-N 3-[3-(5-phenylpyridin-3-yl)-1H-pyrazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC=CC=C1)C=1C=C(C=NC=1)C1=CC(=NN1)C1CN(CC1)C#N VSIGRWUWVTXGJD-UHFFFAOYSA-N 0.000 claims 1
- HLIZACUQQCBFSR-UHFFFAOYSA-N 3-[3-(5-pyrimidin-2-ylpyridin-2-yl)-1H-pyrazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound N1=C(N=CC=C1)C=1C=CC(=NC=1)C1=NNC(=C1)C1CN(CC1)C#N HLIZACUQQCBFSR-UHFFFAOYSA-N 0.000 claims 1
- HGBRQTDNVSCLKS-UHFFFAOYSA-N 3-[3-(6-phenylpyridin-2-yl)-1H-1,2,4-triazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC=CC=C1)C1=CC=CC(=N1)C=1NC(=NN=1)C1CN(CC1)C#N HGBRQTDNVSCLKS-UHFFFAOYSA-N 0.000 claims 1
- BTTKRZJGANGWGZ-UHFFFAOYSA-N 3-[3-(6-phenylpyridin-3-yl)-1H-pyrazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC=CC=C1)C1=CC=C(C=N1)C1=CC(=NN1)C1CN(CC1)C#N BTTKRZJGANGWGZ-UHFFFAOYSA-N 0.000 claims 1
- MXBSCRKPYWEOEV-UHFFFAOYSA-N 3-[3-[3-(1,2-oxazol-4-yl)phenyl]-1H-pyrazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound O1N=CC(=C1)C=1C=C(C=CC=1)C1=CC(=NN1)C1CN(CC1)C#N MXBSCRKPYWEOEV-UHFFFAOYSA-N 0.000 claims 1
- JKONEAMLMRDSTM-UHFFFAOYSA-N 3-[3-[3-(1-methylimidazol-4-yl)phenyl]-1H-pyrazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound CN1C=NC(=C1)C=1C=C(C=CC=1)C1=CC(=NN1)C1CN(CC1)C#N JKONEAMLMRDSTM-UHFFFAOYSA-N 0.000 claims 1
- VPDMTPYIHUXNOM-UHFFFAOYSA-N 3-[3-[3-(1-methylpyrazol-4-yl)phenyl]-1H-pyrazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound CN1N=CC(=C1)C=1C=C(C=CC=1)C1=CC(=NN1)C1CN(CC1)C#N VPDMTPYIHUXNOM-UHFFFAOYSA-N 0.000 claims 1
- ANTQCPSRTHYCLX-UHFFFAOYSA-N 3-[3-[3-(3-cyanophenyl)azetidin-1-yl]-1,2,4-oxadiazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound C(#N)C=1C=C(C=CC=1)C1CN(C1)C1=NOC(=N1)C1CN(CC1)C#N ANTQCPSRTHYCLX-UHFFFAOYSA-N 0.000 claims 1
- XUONDMDRBZLPNI-UHFFFAOYSA-N 3-[3-[3-(4-chlorophenyl)phenyl]-1H-pyrazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound ClC1=CC=C(C=C1)C1=CC(=CC=C1)C1=NNC(=C1)C1CN(CC1)C#N XUONDMDRBZLPNI-UHFFFAOYSA-N 0.000 claims 1
- SGHSQCHUGBYEFI-UHFFFAOYSA-N 3-[3-[3-(4-cyanophenyl)azetidin-1-yl]-1,2,4-oxadiazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound C(#N)C1=CC=C(C=C1)C1CN(C1)C1=NOC(=N1)C1CN(CC1)C#N SGHSQCHUGBYEFI-UHFFFAOYSA-N 0.000 claims 1
- ZDDYNBQDBFCWDG-UHFFFAOYSA-N 3-[3-[3-(4-methoxyphenyl)phenyl]-1H-pyrazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound COC1=CC=C(C=C1)C1=CC(=CC=C1)C1=NNC(=C1)C1CN(CC1)C#N ZDDYNBQDBFCWDG-UHFFFAOYSA-N 0.000 claims 1
- QAPZJNBYJJCATL-UHFFFAOYSA-N 3-[3-[4-(4-methylpiperazin-1-yl)phenyl]-1H-pyrazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound CN1CCN(CC1)C1=CC=C(C=C1)C1=NNC(=C1)C1CN(CC1)C#N QAPZJNBYJJCATL-UHFFFAOYSA-N 0.000 claims 1
- PBGQPKUPFHCQAR-UHFFFAOYSA-N 3-[4-[3-(1-cyanopyrrolidin-2-yl)-1,2,4-oxadiazol-5-yl]pyridin-2-yl]-N-methylbenzamide Chemical compound C(#N)N1C(CCC1)C1=NOC(=N1)C1=CC(=NC=C1)C=1C=C(C(=O)NC)C=CC=1 PBGQPKUPFHCQAR-UHFFFAOYSA-N 0.000 claims 1
- NOEAGGHDPDDKND-UHFFFAOYSA-N 3-[4-[3-(1-cyanopyrrolidin-2-yl)-1,2,4-oxadiazol-5-yl]pyridin-2-yl]benzamide Chemical compound C(#N)N1C(CCC1)C1=NOC(=N1)C1=CC(=NC=C1)C=1C=C(C(=O)N)C=CC=1 NOEAGGHDPDDKND-UHFFFAOYSA-N 0.000 claims 1
- JRMSKUNXCIFTPE-UHFFFAOYSA-N 3-[4-fluoro-3-(3-phenylphenyl)-1H-pyrazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC(=CC=C1)C1=NNC(=C1F)C1CN(CC1)C#N)C1=CC=CC=C1 JRMSKUNXCIFTPE-UHFFFAOYSA-N 0.000 claims 1
- HVVORJVKCWLMDA-UHFFFAOYSA-N 3-[4-fluoro-3-(6-piperidin-1-ylpyridin-2-yl)-1H-pyrazol-5-yl]pyrrolidine-1-carbonitrile Chemical compound FC=1C(=NNC=1C1CN(CC1)C#N)C1=NC(=CC=C1)N1CCCCC1 HVVORJVKCWLMDA-UHFFFAOYSA-N 0.000 claims 1
- TUNCUIAIPNIEAA-UHFFFAOYSA-N 3-[5-(1,3-benzothiazol-6-yl)-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound S1C=NC2=C1C=C(C=C2)C1=NC(=NO1)C1CN(CC1)C#N TUNCUIAIPNIEAA-UHFFFAOYSA-N 0.000 claims 1
- ZBAMOHALKFGMGR-UHFFFAOYSA-N 3-[5-(1-cyanopyrrolidin-3-yl)-1H-pyrazol-3-yl]-N,N-dimethylbenzamide Chemical compound C(#N)N1CC(CC1)C1=CC(=NN1)C=1C=C(C(=O)N(C)C)C=CC=1 ZBAMOHALKFGMGR-UHFFFAOYSA-N 0.000 claims 1
- HRQAJJGYTAIZBW-UHFFFAOYSA-N 3-[5-(1-cyanopyrrolidin-3-yl)-1H-pyrazol-3-yl]benzamide Chemical compound C(#N)N1CC(CC1)C1=CC(=NN1)C=1C=C(C(=O)N)C=CC=1 HRQAJJGYTAIZBW-UHFFFAOYSA-N 0.000 claims 1
- YIEKGNAARNCIEE-UHFFFAOYSA-N 3-[5-(1-phenylpyrrolidin-3-yl)-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC=CC=C1)N1CC(CC1)C1=NC(=NO1)C1CN(CC1)C#N YIEKGNAARNCIEE-UHFFFAOYSA-N 0.000 claims 1
- DUIFJQHKEVWQSF-UHFFFAOYSA-N 3-[5-(2-methylquinolin-6-yl)-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound CC1=NC2=CC=C(C=C2C=C1)C1=NC(=NO1)C1CN(CC1)C#N DUIFJQHKEVWQSF-UHFFFAOYSA-N 0.000 claims 1
- JBQLABWEJCCDDK-UHFFFAOYSA-N 3-[5-(2-oxo-6-phenyl-1H-pyridin-3-yl)-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound O=C1NC(=CC=C1C1=NC(=NO1)C1CN(CC1)C#N)C1=CC=CC=C1 JBQLABWEJCCDDK-UHFFFAOYSA-N 0.000 claims 1
- DSQYONOFHDLCKP-UHFFFAOYSA-N 3-[5-(2-phenylmethoxyphenyl)-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound C(C1=CC=CC=C1)OC1=C(C=CC=C1)C1=NC(=NO1)C1CN(CC1)C#N DSQYONOFHDLCKP-UHFFFAOYSA-N 0.000 claims 1
- QMMBUVSSSWLSJX-UHFFFAOYSA-N 3-[5-(2-phenylquinolin-4-yl)-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC=CC=C1)C1=NC2=CC=CC=C2C(=C1)C1=NC(=NO1)C1CN(CC1)C#N QMMBUVSSSWLSJX-UHFFFAOYSA-N 0.000 claims 1
- SZTNQZRVZVZZSY-UHFFFAOYSA-N 3-[5-(3-phenylphenyl)-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound C1(=CC(=CC=C1)C1=NC(=NO1)C1CN(CC1)C#N)C1=CC=CC=C1 SZTNQZRVZVZZSY-UHFFFAOYSA-N 0.000 claims 1
- YGIJXAKZGRBCBT-UHFFFAOYSA-N 3-[5-(4-bromophenyl)-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound BrC1=CC=C(C=C1)C1=NC(=NO1)C1CN(CC1)C#N YGIJXAKZGRBCBT-UHFFFAOYSA-N 0.000 claims 1
- UXUTWRDJQGURGO-UHFFFAOYSA-N 3-[5-(4-methoxyquinolin-2-yl)-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound COC1=CC(=NC2=CC=CC=C12)C1=NC(=NO1)C1CN(CC1)C#N UXUTWRDJQGURGO-UHFFFAOYSA-N 0.000 claims 1
- BBIABDLYPGWJDU-UHFFFAOYSA-N 3-[5-(4-morpholin-4-ylphenyl)-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound O1CCN(CC1)C1=CC=C(C=C1)C1=NC(=NO1)C1CN(CC1)C#N BBIABDLYPGWJDU-UHFFFAOYSA-N 0.000 claims 1
- UBFCXCZMMWPLMJ-UHFFFAOYSA-N 3-[5-[3-chloro-5-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound ClC=1C=C(C=C(C=1)OC(F)(F)F)C1=NC(=NO1)C1CN(CC1)C#N UBFCXCZMMWPLMJ-UHFFFAOYSA-N 0.000 claims 1
- LIMRCTOYDOPWQU-UHFFFAOYSA-N 3-[5-[4-(1-methylpyrazol-4-yl)phenyl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound Cn1cc(cn1)-c1ccc(cc1)-c1nc(no1)C1CCN(C1)C#N LIMRCTOYDOPWQU-UHFFFAOYSA-N 0.000 claims 1
- ICPQGFFGCWSMBD-BZSJEYESSA-N 3-[5-[4-[(3R)-3-methoxypyrrolidin-1-yl]phenyl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carbonitrile Chemical compound CO[C@H]1CN(CC1)C1=CC=C(C=C1)C1=NC(=NO1)C1CN(CC1)C#N ICPQGFFGCWSMBD-BZSJEYESSA-N 0.000 claims 1
- GZQODNUPQUSDEC-UHFFFAOYSA-N 3-[6-(1H-indazol-5-yl)-1H-imidazo[4,5-b]pyridin-2-yl]pyrrolidine-1-carbonitrile Chemical compound N1N=CC2=CC(=CC=C12)C=1C=C2C(=NC=1)NC(=N2)C1CN(CC1)C#N GZQODNUPQUSDEC-UHFFFAOYSA-N 0.000 claims 1
- BLLXEZJUXSEDGS-UHFFFAOYSA-N 3-[6-(1H-pyrazol-4-yl)-1H-imidazo[4,5-b]pyridin-2-yl]pyrrolidine-1-carbonitrile Chemical compound N1N=CC(=C1)C=1C=C2C(=NC=1)NC(=N2)C1CN(CC1)C#N BLLXEZJUXSEDGS-UHFFFAOYSA-N 0.000 claims 1
- YAWZLEMVXIZBGA-UHFFFAOYSA-N 3-[6-(2-fluoro-5-methylphenyl)-1H-benzimidazol-2-yl]pyrrolidine-1-carbonitrile Chemical compound FC1=C(C=C(C=C1)C)C=1C=CC2=C(NC(=N2)C2CN(CC2)C#N)C=1 YAWZLEMVXIZBGA-UHFFFAOYSA-N 0.000 claims 1
- IAATZMFOZRCSRI-UHFFFAOYSA-N 3-[6-(2-phenylmethoxyphenyl)-1H-benzimidazol-2-yl]pyrrolidine-1-carbonitrile Chemical compound C(C1=CC=CC=C1)OC1=C(C=CC=C1)C=1C=CC2=C(NC(=N2)C2CN(CC2)C#N)C=1 IAATZMFOZRCSRI-UHFFFAOYSA-N 0.000 claims 1
- KXFUJRBAARPOPX-UHFFFAOYSA-N 3-[6-(3-cyanophenyl)-1H-benzimidazol-2-yl]pyrrolidine-1-carbonitrile Chemical compound C(#N)C=1C=C(C=CC=1)C=1C=CC2=C(NC(=N2)C2CN(CC2)C#N)C=1 KXFUJRBAARPOPX-UHFFFAOYSA-N 0.000 claims 1
- JGTPRBWGYWSRQG-UHFFFAOYSA-N 3-[6-(3-cyanophenyl)-1H-imidazo[4,5-b]pyridin-2-yl]pyrrolidine-1-carbonitrile Chemical compound C(#N)C=1C=C(C=CC=1)C=1C=C2C(=NC=1)NC(=N2)C1CN(CC1)C#N JGTPRBWGYWSRQG-UHFFFAOYSA-N 0.000 claims 1
- QLDJJFRELGBSFT-UHFFFAOYSA-N 3-[6-(6-methoxypyridin-3-yl)-1H-imidazo[4,5-b]pyridin-2-yl]pyrrolidine-1-carbonitrile Chemical compound COC1=CC=C(C=N1)C=1C=C2C(=NC=1)NC(=N2)C1CN(CC1)C#N QLDJJFRELGBSFT-UHFFFAOYSA-N 0.000 claims 1
- PHWCPYKRWAJABO-UHFFFAOYSA-N 3-[6-(6-propan-2-yloxypyridin-3-yl)-1H-benzimidazol-2-yl]pyrrolidine-1-carbonitrile Chemical compound C(C)(C)OC1=CC=C(C=N1)C=1C=CC2=C(NC(=N2)C2CN(CC2)C#N)C=1 PHWCPYKRWAJABO-UHFFFAOYSA-N 0.000 claims 1
- FAXJWSIBPXZAQB-UHFFFAOYSA-N 3-[6-[1-(2-methylpropyl)pyrazol-4-yl]-1H-benzimidazol-2-yl]pyrrolidine-1-carbonitrile Chemical compound C(C(C)C)N1N=CC(=C1)C=1C=CC2=C(NC(=N2)C2CN(CC2)C#N)C=1 FAXJWSIBPXZAQB-UHFFFAOYSA-N 0.000 claims 1
- WKBSYXTYXLMPCH-UHFFFAOYSA-N 3-[7-(3,5-dimethyl-1,2-oxazol-4-yl)imidazo[1,2-a]pyridin-3-yl]pyrrolidine-1-carbonitrile Chemical compound Cc1noc(C)c1-c1ccn2c(cnc2c1)C1CCN(C1)C#N WKBSYXTYXLMPCH-UHFFFAOYSA-N 0.000 claims 1
- WBAWOJUDFUURPA-UHFFFAOYSA-N 4-[2-(1-cyanopyrrolidin-3-yl)-3H-benzimidazol-5-yl]-N-methylbenzamide Chemical compound C(#N)N1CC(CC1)C1=NC2=C(N1)C=C(C=C2)C1=CC=C(C(=O)NC)C=C1 WBAWOJUDFUURPA-UHFFFAOYSA-N 0.000 claims 1
- SODTWURBBLTSLJ-INIZCTEOSA-N 4-[2-[3-[(2S)-1-cyanopyrrolidin-2-yl]-1,2,4-oxadiazol-5-yl]pyridin-4-yl]pyridine-2-carbonitrile Chemical compound N#CN1CCC[C@H]1C1=NOC(=N1)C1=NC=CC(=C1)C1=CC(=NC=C1)C#N SODTWURBBLTSLJ-INIZCTEOSA-N 0.000 claims 1
- DLPQKBXDBZEDMX-UHFFFAOYSA-N 4-[3-[3-(1-cyanopyrrolidin-2-yl)-1,2,4-oxadiazol-5-yl]phenyl]benzamide Chemical compound C(#N)N1C(CCC1)C1=NOC(=N1)C=1C=C(C=CC=1)C1=CC=C(C=C1)C(=O)N DLPQKBXDBZEDMX-UHFFFAOYSA-N 0.000 claims 1
- RGPFFNHGLZFBJL-INIZCTEOSA-N 4-[4-[3-[(2S)-1-cyanopyrrolidin-2-yl]-1,2,4-oxadiazol-5-yl]pyridin-2-yl]pyridine-2-carbonitrile Chemical compound N#CN1CCC[C@H]1C1=NOC(=N1)C1=CC(=NC=C1)C1=CC(=NC=C1)C#N RGPFFNHGLZFBJL-INIZCTEOSA-N 0.000 claims 1
- MJFDDQILWINPDA-AWEZNQCLSA-N 4-[4-[3-[(2S)-1-cyanopyrrolidin-2-yl]-1,2,4-oxadiazol-5-yl]pyrimidin-2-yl]pyridine-2-carbonitrile Chemical compound C(#N)N1[C@@H](CCC1)C1=NOC(=N1)C1=NC(=NC=C1)C1=CC(=NC=C1)C#N MJFDDQILWINPDA-AWEZNQCLSA-N 0.000 claims 1
- AFIFEJAFENCNPZ-UHFFFAOYSA-N 4-[5-(1-cyanopyrrolidin-3-yl)-1H-pyrazol-3-yl]benzamide Chemical compound C(#N)N1CC(CC1)C1=CC(=NN1)C1=CC=C(C(=O)N)C=C1 AFIFEJAFENCNPZ-UHFFFAOYSA-N 0.000 claims 1
- LMIQSTBIGCMWPZ-HNNXBMFYSA-N 4-[5-[3-[(2S)-1-cyanopyrrolidin-2-yl]-1,2,4-oxadiazol-5-yl]pyridazin-3-yl]pyridine-2-carbonitrile Chemical compound C(#N)N1[C@@H](CCC1)C1=NOC(=N1)C=1C=C(N=NC=1)C1=CC(=NC=C1)C#N LMIQSTBIGCMWPZ-HNNXBMFYSA-N 0.000 claims 1
- JHGGNSNCMZKXSC-HNNXBMFYSA-N 4-[6-[3-[(2S)-1-cyanopyrrolidin-2-yl]-1,2,4-oxadiazol-5-yl]pyrazin-2-yl]pyridine-2-carbonitrile Chemical compound C(#N)N1[C@@H](CCC1)C1=NOC(=N1)C1=CN=CC(=N1)C1=CC(=NC=C1)C#N JHGGNSNCMZKXSC-HNNXBMFYSA-N 0.000 claims 1
- CHMURZHKNNAQEG-INIZCTEOSA-N 4-[6-[3-[(2S)-1-cyanopyrrolidin-2-yl]-1,2,4-oxadiazol-5-yl]pyridin-2-yl]pyridine-2-carbonitrile Chemical compound N#CN1CCC[C@H]1C1=NOC(=N1)C1=CC=CC(=N1)C1=CC(=NC=C1)C#N CHMURZHKNNAQEG-INIZCTEOSA-N 0.000 claims 1
- OWPGYEPSEFLJNK-UHFFFAOYSA-N 5-(1-benzylpyrrolidin-3-yl)-3-(3-phenylphenyl)-1H-1,2,4-triazole Chemical compound C(N1CCC(C1)c1nc(n[nH]1)-c1cccc(c1)-c1ccccc1)c1ccccc1 OWPGYEPSEFLJNK-UHFFFAOYSA-N 0.000 claims 1
- VTJQPWVTFHSZBS-AWEZNQCLSA-N 5-[4-[3-[(2S)-1-cyanopyrrolidin-2-yl]-1,2,4-oxadiazol-5-yl]pyrimidin-2-yl]pyridine-2-carbonitrile Chemical compound C(#N)N1[C@@H](CCC1)C1=NOC(=N1)C1=NC(=NC=C1)C=1C=CC(=NC=1)C#N VTJQPWVTFHSZBS-AWEZNQCLSA-N 0.000 claims 1
- RCLTZUYLFNTQMP-UHFFFAOYSA-N 5-[5-(1-cyanopyrrolidin-3-yl)-1H-pyrazol-3-yl]-N-methylpyridine-2-carboxamide Chemical compound C(#N)N1CC(CC1)C1=CC(=NN1)C=1C=CC(=NC=1)C(=O)NC RCLTZUYLFNTQMP-UHFFFAOYSA-N 0.000 claims 1
- VMLUNXAZFHLLKX-INIZCTEOSA-N 6-[2-[(2S)-1-cyanopyrrolidin-2-yl]-1,3-benzoxazol-5-yl]pyridine-2-carbonitrile Chemical compound C(#N)N1[C@@H](CCC1)C=1OC2=C(N=1)C=C(C=C2)C1=CC=CC(=N1)C#N VMLUNXAZFHLLKX-INIZCTEOSA-N 0.000 claims 1
- SZHDMYNPEVEWAR-INIZCTEOSA-N 6-[2-[(2S)-1-cyanopyrrolidin-2-yl]-1,3-benzoxazol-6-yl]pyridine-2-carbonitrile Chemical compound C(#N)N1[C@@H](CCC1)C=1OC2=C(N=1)C=CC(=C2)C1=CC=CC(=N1)C#N SZHDMYNPEVEWAR-INIZCTEOSA-N 0.000 claims 1
- CIPOCLPHOMAXCH-UHFFFAOYSA-N 6-[4-[3-(1-cyanopyrrolidin-2-yl)-1,2,4-oxadiazol-5-yl]pyridin-2-yl]pyridine-2-carbonitrile Chemical compound N#CN1CCCC1C1=NOC(=N1)C1=CC(=NC=C1)C1=NC(=CC=C1)C#N CIPOCLPHOMAXCH-UHFFFAOYSA-N 0.000 claims 1
- 238000006412 Alper carbonylation reaction Methods 0.000 claims 1
- 102100026882 Alpha-synuclein Human genes 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
- 102000051485 Bcl-2 family Human genes 0.000 claims 1
- 108700038897 Bcl-2 family Proteins 0.000 claims 1
- XVXPIHGBSLICTF-UHFFFAOYSA-N C1CC(N(C1)C#N)C2=NOC(=N2)C3=CC=CC(=C3)C4=CC=CC=C4C(=O)O Chemical compound C1CC(N(C1)C#N)C2=NOC(=N2)C3=CC=CC(=C3)C4=CC=CC=C4C(=O)O XVXPIHGBSLICTF-UHFFFAOYSA-N 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-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
- 101710088194 Dehydrogenase Proteins 0.000 claims 1
- 206010067889 Dementia with Lewy bodies Diseases 0.000 claims 1
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims 1
- 102100022207 E3 ubiquitin-protein ligase parkin Human genes 0.000 claims 1
- 206010016654 Fibrosis Diseases 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 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
- 101000605835 Homo sapiens Serine/threonine-protein kinase PINK1, mitochondrial 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
- 201000002832 Lewy body dementia Diseases 0.000 claims 1
- 108010027062 Long-Chain Acyl-CoA Dehydrogenase Proteins 0.000 claims 1
- 102000018653 Long-Chain Acyl-CoA Dehydrogenase Human genes 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 208000035172 MERRF 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
- JWZNCXMURZXNNE-HNNXBMFYSA-N N#CN1CCC[C@H]1C1=NOC(=N1)C1=CC2=C(C=CC(=N2)C#N)C=C1 Chemical compound N#CN1CCC[C@H]1C1=NOC(=N1)C1=CC2=C(C=CC(=N2)C#N)C=C1 JWZNCXMURZXNNE-HNNXBMFYSA-N 0.000 claims 1
- SAWIUVPKLUBKTJ-UHFFFAOYSA-N N-[3-[5-(1-cyanopyrrolidin-3-yl)-1H-pyrazol-3-yl]phenyl]acetamide Chemical compound C(#N)N1CC(CC1)C1=CC(=NN1)C=1C=C(C=CC=1)NC(C)=O SAWIUVPKLUBKTJ-UHFFFAOYSA-N 0.000 claims 1
- SSJKIVMKMOEFSA-UHFFFAOYSA-N N-[4-[5-(1-cyanopyrrolidin-3-yl)-1H-pyrazol-3-yl]phenyl]acetamide Chemical compound C(#N)N1CC(CC1)C1=CC(=NN1)C1=CC=C(C=C1)NC(C)=O SSJKIVMKMOEFSA-UHFFFAOYSA-N 0.000 claims 1
- CNPGZMUSKHEQAC-UHFFFAOYSA-N N-[5-(1-cyanopyrrolidin-3-yl)-1H-pyrazol-3-yl]-2-phenylacetamide Chemical compound C(#N)N1CC(CC1)C1=NNC(=C1)NC(CC1=CC=CC=C1)=O CNPGZMUSKHEQAC-UHFFFAOYSA-N 0.000 claims 1
- GLUMTLWBWPYEOF-UHFFFAOYSA-N N-[5-(1-cyanopyrrolidin-3-yl)-1H-pyrazol-3-yl]benzamide Chemical compound C(#N)N1CC(CC1)C1=NNC(=C1)NC(C1=CC=CC=C1)=O GLUMTLWBWPYEOF-UHFFFAOYSA-N 0.000 claims 1
- IZXICJYOHJQMIA-DEOSSOPVSA-N N-benzyl-3-[2-[(2S)-1-cyanopyrrolidin-2-yl]-1,3-benzoxazol-5-yl]-4-methylbenzenesulfonamide Chemical compound C(C1=CC=CC=C1)NS(=O)(=O)C1=CC(=C(C=C1)C)C=1C=CC2=C(N=C(O2)[C@H]2N(CCC2)C#N)C=1 IZXICJYOHJQMIA-DEOSSOPVSA-N 0.000 claims 1
- 102100035196 POLG alternative reading frame Human genes 0.000 claims 1
- 208000027089 Parkinsonian disease Diseases 0.000 claims 1
- 208000013234 Pearson syndrome Diseases 0.000 claims 1
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 1
- 208000021886 Pyruvate carboxylase deficiency Diseases 0.000 claims 1
- 208000007014 Retinitis pigmentosa Diseases 0.000 claims 1
- 102100038376 Serine/threonine-protein kinase PINK1, mitochondrial Human genes 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 108090000185 alpha-Synuclein Proteins 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 230000005775 apoptotic pathway Effects 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 125000005872 benzooxazolyl group Chemical group 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 235000010290 biphenyl Nutrition 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
- 201000008609 cerebral creatine deficiency syndrome Diseases 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 230000002759 chromosomal effect Effects 0.000 claims 1
- 230000003920 cognitive function Effects 0.000 claims 1
- 210000001072 colon Anatomy 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 230000007423 decrease Effects 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 208000033679 diabetic kidney disease Diseases 0.000 claims 1
- 125000005045 dihydroisoquinolinyl group Chemical group C1(NC=CC2=CC=CC=C12)* 0.000 claims 1
- 230000004064 dysfunction Effects 0.000 claims 1
- 201000009028 early myoclonic encephalopathy Diseases 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 230000004761 fibrosis Effects 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 210000003128 head Anatomy 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 208000032839 leukemia 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
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims 1
- 201000002697 mitochondrial DNA depletion syndrome Diseases 0.000 claims 1
- 208000012268 mitochondrial disease Diseases 0.000 claims 1
- 230000002438 mitochondrial effect Effects 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 210000003205 muscle Anatomy 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 208000031225 myocardial ischemia Diseases 0.000 claims 1
- 125000001624 naphthyl group Chemical group 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
- 229910052757 nitrogen Inorganic materials 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
- 210000001672 ovary Anatomy 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 210000000496 pancreas Anatomy 0.000 claims 1
- 102000045222 parkin Human genes 0.000 claims 1
- 208000033808 peripheral neuropathy Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 210000002307 prostate Anatomy 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 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
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- GZDYCSOBGRIGEV-HXUWFJFHSA-N tert-butyl (3R)-3-[5-[2-(3,4-dihydro-1H-isoquinolin-2-yl)pyridin-4-yl]-1,2,4-oxadiazol-3-yl]pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC[C@H](C1)C1=NOC(=N1)C1=CC(=NC=C1)N1CCC2=C(C1)C=CC=C2 GZDYCSOBGRIGEV-HXUWFJFHSA-N 0.000 claims 1
- 210000001550 testis Anatomy 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 210000001519 tissue Anatomy 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1605059.3 | 2016-03-24 | ||
| GBGB1605059.3A GB201605059D0 (en) | 2016-03-24 | 2016-03-24 | Novel compounds |
| GBGB1700839.2A GB201700839D0 (en) | 2017-01-18 | 2017-01-18 | Novel compounds |
| GB1700839.2 | 2017-01-18 | ||
| PCT/GB2017/050830 WO2017163078A1 (en) | 2016-03-24 | 2017-03-23 | 1-cyano-pyrrolidine derivatives as dbu inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019513135A JP2019513135A (ja) | 2019-05-23 |
| JP2019513135A5 true JP2019513135A5 (https=) | 2020-02-27 |
| JP6959252B2 JP6959252B2 (ja) | 2021-11-02 |
Family
ID=58455357
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018549534A Active JP6959252B2 (ja) | 2016-03-24 | 2017-03-23 | Ｄｕｂ阻害剤としての１−シアノピロリジン誘導体 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US11352339B2 (https=) |
| EP (1) | EP3433246B1 (https=) |
| JP (1) | JP6959252B2 (https=) |
| CN (1) | CN108884068B (https=) |
| MA (1) | MA43753A (https=) |
| WO (1) | WO2017163078A1 (https=) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX373656B (es) | 2015-03-30 | 2020-04-02 | Mission Therapeutics Ltd | Compuestos de 1-ciano-pirrolidina como inhibidores de las enzimas desubiquitinantes, como la hidrolasa 30 de la c-terminal de la ubiquitina (usp30), y el uso de los mismos en el tratamiento de condiciones de disfunción mitocondrial y tratamiento de cancér. |
| US10669234B2 (en) | 2015-07-14 | 2020-06-02 | 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 |
| GB201604647D0 (en) | 2016-03-18 | 2016-05-04 | Mission Therapeutics Ltd | Novel compounds |
| 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 |
| GB201708652D0 (en) | 2017-05-31 | 2017-07-12 | Mission Therapeutics Ltd | Novel compounds and uses |
| JP7208931B2 (ja) | 2017-06-20 | 2023-01-19 | ミッション セラピューティクス リミティド | Ｄｕｂ阻害剤としての活性をもつ置換シアノピロリジン類 |
| BR112020003725A2 (pt) | 2017-10-06 | 2020-11-03 | Forma Therapeutics, Inc. | inibição da peptidase 30 específica de ubiquitina |
| GB2571731A (en) * | 2018-03-06 | 2019-09-11 | Mission Therapeutics Ltd | Novel compounds and uses |
| JP7449242B2 (ja) | 2018-05-17 | 2024-03-13 | フォーマ セラピューティクス，インコーポレイテッド | ユビキチン特異的ペプチダーゼ３０（ｕｓｐ３０）阻害剤として有用な縮合二環化合物 |
| JP7434285B2 (ja) * | 2018-08-14 | 2024-02-20 | アムジエン・インコーポレーテツド | Ｎ－シアノ－７－アザノルボルナン誘導体及びその使用 |
| LT3860989T (lt) * | 2018-10-05 | 2023-06-12 | Forma Therapeutics, Inc. | Sulieti pirolinai, kurie veikia kaip ubikvitinui specifinės proteazės 30 (ups30) inhibitoriai |
| CN120698983A (zh) | 2018-12-20 | 2025-09-26 | C4医药公司 | 靶向蛋白降解 |
| 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 |
| WO2021007477A1 (en) | 2019-07-11 | 2021-01-14 | E-Scape Bio, Inc. | Indazoles and azaindazoles as lrrk2 inhibitors |
| GB201912674D0 (en) | 2019-09-04 | 2019-10-16 | Mission Therapeutics Ltd | Novel compounds |
| WO2021204856A1 (en) * | 2020-04-08 | 2021-10-14 | Mission Therapeutics Limited | N-cyanopyrrolidines with activity as usp30 inhibitors |
| IL298526A (en) | 2020-05-28 | 2023-01-01 | Mission Therapeutics Ltd | N-(1-cyano-pyrrolidin-3-yl)-5-(3-(trifluoromethyl)phenyl)oxazole-2-carboxamide derivatives and the corresponding oxadiazole derivatives as usp30 inhibitors for the treatment of mitochondrial dysfunction |
| BR112022019722A2 (pt) | 2020-06-04 | 2022-12-20 | Mission Therapeutics Ltd | N-cianopirrolidinas com atividade como inibidores de usp30 |
| DK4161929T3 (da) * | 2020-06-08 | 2025-08-18 | Mission Therapeutics Ltd | 1-(5-(2-cyanopyridin-4-yl)oxazol-2-carbonyl)-4-methylhexahydropyrrolo[3,4-b]pyrrol-5(1h)-carbonitril som usp30-hæmmer til anvendelse i behandling af mitokondriedysfunktion, cancer og fibrose |
| GB202016800D0 (en) | 2020-10-22 | 2020-12-09 | Mission Therapeutics Ltd | Novel compounds |
| US20250034122A1 (en) | 2021-12-01 | 2025-01-30 | Mission Therapeutics Limited | Substituted n-cyanopyrrolidines with activity as usp30 inhibitors |
| CN114646700B (zh) * | 2022-03-01 | 2023-10-20 | 浙江国邦药业有限公司 | 一种（s）-吡咯烷-2-甲腈盐酸盐的检测方法 |
| GB202408928D0 (en) | 2024-06-21 | 2024-08-07 | Mission Therapeutics Ltd | Novel compounds |
| GB202411060D0 (en) | 2024-07-29 | 2024-09-11 | Mission Therapeutics Ltd | Novel compounds |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5665754A (en) | 1993-09-20 | 1997-09-09 | Glaxo Wellcome Inc. | Substituted pyrrolidines |
| WO2001077073A1 (en) | 2000-04-06 | 2001-10-18 | Merck Frosst Canada & Co. | Cathepsin cysteine protease inhibitors |
| RU2662443C2 (ru) | 2011-11-01 | 2018-07-26 | Ф. Хоффманн-Ля Рош Аг | Имидазопиридазины |
| JP6178861B2 (ja) | 2012-11-02 | 2017-08-09 | ファイザー・インク | ブルトン型チロシンキナーゼ阻害剤 |
| GB201309085D0 (en) | 2013-05-20 | 2013-07-03 | Redx Pharma Ltd | Compounds |
| CA2918242C (en) | 2013-07-31 | 2022-06-21 | Merck Patent Gmbh | Pyridines, pyrimidines, and pyrazines, as btk inhibitors and uses thereof |
| BR112016008632A8 (pt) * | 2013-10-21 | 2020-03-17 | Merck Patent Gmbh | compostos de heteroarila como inibidores de btk, seus usos, e composição farmacêutica |
| GB201404987D0 (en) | 2014-03-20 | 2014-05-07 | Redx Pharma Ltd | Compounds |
| WO2015157955A1 (en) | 2014-04-17 | 2015-10-22 | Abbvie Inc. | Heterocyclic btk inhibit ors |
| CN105017256A (zh) | 2014-04-29 | 2015-11-04 | 浙江导明医药科技有限公司 | 多氟化合物作为布鲁顿酪氨酸激酶抑制剂 |
| WO2016019237A2 (en) * | 2014-07-31 | 2016-02-04 | Pharmacyclics Llc | Inhibitors of bruton's tyrosine kinase |
| GB201416754D0 (en) | 2014-09-23 | 2014-11-05 | Mission Therapeutics Ltd | Novel compounds |
| EA034931B1 (ru) | 2014-10-24 | 2020-04-08 | Бристол-Майерс Сквибб Компани | Индолкарбоксамидные соединения |
| MX373656B (es) * | 2015-03-30 | 2020-04-02 | Mission Therapeutics Ltd | Compuestos de 1-ciano-pirrolidina como inhibidores de las enzimas desubiquitinantes, como la hidrolasa 30 de la c-terminal de la ubiquitina (usp30), y el uso de los mismos en el tratamiento de condiciones de disfunción mitocondrial y tratamiento de cancér. |
| WO2016192074A1 (en) | 2015-06-04 | 2016-12-08 | Merck Sharp & Dohme Corp. | Btk inhibitors |
| US10669234B2 (en) | 2015-07-14 | 2020-06-02 | 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 |
| US10570118B2 (en) * | 2016-01-13 | 2020-02-25 | Boehringer Ingelheim International Gmbh | Isoquinolones as BTK inhibitors |
| 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 |
| GB201604647D0 (en) | 2016-03-18 | 2016-05-04 | Mission Therapeutics Ltd | Novel compounds |
| US11180489B2 (en) | 2016-03-30 | 2021-11-23 | U niversity of Virginia Patent Foundation | Sphingosine kinase inhibitor amidoxime prodrugs |
| CN107383013B (zh) | 2016-05-16 | 2020-03-31 | 苏州信诺维医药科技有限公司 | 作为btk抑制剂的吡唑并嘧啶衍生物及其制备方法和药物组合物 |
| AU2017265219B2 (en) | 2016-05-16 | 2021-02-04 | Evopoint Biosciences Co., Ltd. | 5-aminopyrazole carboxamide derivative as BTK inhibitor and preparation method and pharmaceutical composition thereof |
| 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 |
-
2017
- 2017-03-23 JP JP2018549534A patent/JP6959252B2/ja active Active
- 2017-03-23 MA MA043753A patent/MA43753A/fr unknown
- 2017-03-23 US US16/087,515 patent/US11352339B2/en active Active
- 2017-03-23 EP EP17714540.6A patent/EP3433246B1/en active Active
- 2017-03-23 CN CN201780018998.XA patent/CN108884068B/zh active Active
- 2017-03-23 WO PCT/GB2017/050830 patent/WO2017163078A1/en not_active Ceased
-
2022
- 2022-02-18 US US17/674,943 patent/US11945797B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2019513135A5 (https=) | ||
| JP2018510183A5 (https=) | ||
| HRP20210791T2 (hr) | 1-cijano-pirolidin spojevi kao usp30 inhibitori | |
| JP2019504009A5 (https=) | ||
| JP2018524367A5 (https=) | ||
| JP2019501142A5 (https=) | ||
| JP2019533659A5 (https=) | ||
| US11945797B2 (en) | 1-cyano-pyrrolidine derivatives as dub inhibitors | |
| JP5055136B2 (ja) | Ｖｅｇｆ−ｒ２阻害剤としてのイミダゾ（１，２−ａ）ピリジン化合物 | |
| JP2017512794A5 (https=) | ||
| JP2016522246A5 (https=) | ||
| JP2014517833A5 (https=) | ||
| JP2019532938A5 (https=) | ||
| JP2019519484A5 (https=) | ||
| JP2019508467A5 (https=) | ||
| JP2022500402A5 (https=) | ||
| JP2017508766A5 (https=) | ||
| CA2703125A1 (en) | Pyrazinyl-substituted pyrrolo[2,3-b]pyridines, compositions thereof, and their use in the treatment of cancer | |
| IL306126A (en) | Heterocyclic compounds | |
| JP2018536687A5 (https=) | ||
| JP2017528515A5 (https=) | ||
| HRP20200805T1 (hr) | Spirociklički spojevi | |
| JPWO2020257180A5 (https=) | ||
| JPWO2020052631A5 (https=) | ||
| HRP20151062T1 (hr) | Derivat azola |