JP2019513135A5 - - Google Patents
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- 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
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- -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
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- 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
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- 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
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- 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
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- 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
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| GB201604638D0 (en) | 2016-03-18 | 2016-05-04 | Mission Therapeutics Ltd | Novel compounds |
| WO2017172989A1 (en) | 2016-03-30 | 2017-10-05 | Thorpe Steven Brandon | Sphingosine kinase inhibitor amidoxime prodrugs |
| WO2017198049A1 (zh) | 2016-05-16 | 2017-11-23 | 浙江予川医药科技有限公司 | 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 |
| KR102404759B1 (ko) | 2016-05-16 | 2022-05-31 | 쑤저우 시노벤트 파마슈티칼즈 씨오., 엘티디. | Ｂｔｋ 억제제로서의 5-아미노피라졸 카르복사미드 유도체 및 그것의 제조 방법 및 제약학적 조성물 |
| 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 |
-
2017
- 2017-03-23 CN CN201780018998.XA patent/CN108884068B/zh active Active
- 2017-03-23 MA MA043753A patent/MA43753A/fr unknown
- 2017-03-23 WO PCT/GB2017/050830 patent/WO2017163078A1/en not_active Ceased
- 2017-03-23 JP JP2018549534A patent/JP6959252B2/ja active Active
- 2017-03-23 EP EP17714540.6A patent/EP3433246B1/en active Active
- 2017-03-23 US US16/087,515 patent/US11352339B2/en active Active
-
2022
- 2022-02-18 US US17/674,943 patent/US11945797B2/en active Active
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