JP2019532945A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2019532945A5 JP2019532945A5 JP2019516577A JP2019516577A JP2019532945A5 JP 2019532945 A5 JP2019532945 A5 JP 2019532945A5 JP 2019516577 A JP2019516577 A JP 2019516577A JP 2019516577 A JP2019516577 A JP 2019516577A JP 2019532945 A5 JP2019532945 A5 JP 2019532945A5
- Authority
- JP
- Japan
- Prior art keywords
- deficiency
- ring
- syndrome
- fluoropiperidine
- carbonitrile
- 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 nitro, hydroxyl Chemical group 0.000 claims 54
- 150000001875 compounds Chemical class 0.000 claims 25
- 208000011580 syndromic disease Diseases 0.000 claims 17
- 230000007812 deficiency Effects 0.000 claims 14
- 239000008194 pharmaceutical composition Substances 0.000 claims 13
- 125000000217 alkyl group Chemical group 0.000 claims 12
- 229910052760 oxygen Inorganic materials 0.000 claims 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 9
- 125000001153 fluoro group Chemical group F* 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 229910052757 nitrogen Inorganic materials 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 206010028980 Neoplasm Diseases 0.000 claims 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 7
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 6
- 208000008955 Mucolipidoses Diseases 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 125000002947 alkylene group Chemical group 0.000 claims 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 5
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 5
- 201000011510 cancer Diseases 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 239000001301 oxygen Chemical group 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 125000001425 triazolyl group Chemical group 0.000 claims 5
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 4
- 206010058892 Carnitine deficiency Diseases 0.000 claims 4
- 101000619542 Homo sapiens E3 ubiquitin-protein ligase parkin Proteins 0.000 claims 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
- 125000005434 dihydrobenzoxazinyl group Chemical group O1N(CCC2=C1C=CC=C2)* 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 230000004065 mitochondrial dysfunction Effects 0.000 claims 4
- 230000002438 mitochondrial effect Effects 0.000 claims 4
- 210000003205 muscle Anatomy 0.000 claims 4
- 230000035772 mutation Effects 0.000 claims 4
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 4
- 125000002971 oxazolyl group Chemical group 0.000 claims 4
- 102000045222 parkin Human genes 0.000 claims 4
- 239000011593 sulfur Chemical group 0.000 claims 4
- 208000016505 systemic primary carnitine deficiency disease Diseases 0.000 claims 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims 4
- 208000010444 Acidosis Diseases 0.000 claims 3
- 208000002155 Cytochrome-c Oxidase Deficiency Diseases 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 108700006159 Long-chain acyl-CoA dehydrogenase deficiency Proteins 0.000 claims 3
- 208000001769 Multiple Acyl Coenzyme A Dehydrogenase Deficiency Diseases 0.000 claims 3
- 208000018737 Parkinson disease Diseases 0.000 claims 3
- 208000027089 Parkinsonian disease Diseases 0.000 claims 3
- 230000007950 acidosis Effects 0.000 claims 3
- 208000026545 acidosis disease Diseases 0.000 claims 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 3
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 3
- 208000004687 long chain acyl-CoA dehydrogenase deficiency Diseases 0.000 claims 3
- 208000005548 medium chain acyl-CoA dehydrogenase deficiency Diseases 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 230000004770 neurodegeneration Effects 0.000 claims 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000003003 spiro group Chemical group 0.000 claims 3
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 3
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 206010003591 Ataxia Diseases 0.000 claims 2
- 208000014644 Brain disease Diseases 0.000 claims 2
- 108700005857 Carnitine palmitoyl transferase 1A deficiency Proteins 0.000 claims 2
- 208000005359 Carnitine palmitoyl transferase 1A deficiency Diseases 0.000 claims 2
- 108700005858 Carnitine palmitoyl transferase 2 deficiency Proteins 0.000 claims 2
- 201000002929 Carnitine palmitoyltransferase II deficiency Diseases 0.000 claims 2
- 201000000915 Chronic Progressive External Ophthalmoplegia Diseases 0.000 claims 2
- 208000010354 Coenzyme Q10 deficiency Diseases 0.000 claims 2
- 206010009944 Colon cancer Diseases 0.000 claims 2
- 208000011518 Danon disease Diseases 0.000 claims 2
- 206010012289 Dementia Diseases 0.000 claims 2
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims 2
- 208000004986 Diffuse Cerebral Sclerosis of Schilder Diseases 0.000 claims 2
- 208000032274 Encephalopathy Diseases 0.000 claims 2
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 2
- 208000001500 Glycogen Storage Disease Type IIb Diseases 0.000 claims 2
- 208000035148 Glycogen storage disease due to LAMP-2 deficiency Diseases 0.000 claims 2
- 206010053185 Glycogen storage disease type II Diseases 0.000 claims 2
- 101000804964 Homo sapiens DNA polymerase subunit gamma-1 Proteins 0.000 claims 2
- 101000595929 Homo sapiens POLG alternative reading frame Proteins 0.000 claims 2
- 101000605835 Homo sapiens Serine/threonine-protein kinase PINK1, mitochondrial Proteins 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 241000186660 Lactobacillus Species 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
- 108700000232 Medium chain acyl CoA dehydrogenase deficiency Proteins 0.000 claims 2
- 206010058799 Mitochondrial encephalomyopathy Diseases 0.000 claims 2
- 201000002169 Mitochondrial myopathy Diseases 0.000 claims 2
- 206010072928 Mucolipidosis type II Diseases 0.000 claims 2
- 208000035032 Multiple sulfatase deficiency Diseases 0.000 claims 2
- 102100035196 POLG alternative reading frame Human genes 0.000 claims 2
- 208000013234 Pearson syndrome Diseases 0.000 claims 2
- 208000002009 Pyruvate Dehydrogenase Complex Deficiency Disease Diseases 0.000 claims 2
- 208000021886 Pyruvate carboxylase deficiency Diseases 0.000 claims 2
- 102100038376 Serine/threonine-protein kinase PINK1, mitochondrial Human genes 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000003725 azepanyl group Chemical group 0.000 claims 2
- 201000004010 carnitine palmitoyltransferase I deficiency Diseases 0.000 claims 2
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims 2
- 208000029742 colonic neoplasm Diseases 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 230000001419 dependent effect Effects 0.000 claims 2
- 208000033679 diabetic kidney disease Diseases 0.000 claims 2
- 125000005959 diazepanyl group Chemical group 0.000 claims 2
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims 2
- 125000005045 dihydroisoquinolinyl group Chemical group C1(NC=CC2=CC=CC=C12)* 0.000 claims 2
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims 2
- 125000004655 dihydropyridinyl group Chemical group N1(CC=CC=C1)* 0.000 claims 2
- 125000000532 dioxanyl group Chemical group 0.000 claims 2
- 125000005879 dioxolanyl group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 208000014188 hereditary optic neuropathy Diseases 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims 2
- 229940039696 lactobacillus Drugs 0.000 claims 2
- 201000010901 lateral sclerosis Diseases 0.000 claims 2
- 231100000518 lethal Toxicity 0.000 claims 2
- 230000001665 lethal effect Effects 0.000 claims 2
- 230000008774 maternal effect Effects 0.000 claims 2
- 208000030159 metabolic disease Diseases 0.000 claims 2
- 201000002697 mitochondrial DNA depletion syndrome Diseases 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 208000005264 motor neuron disease Diseases 0.000 claims 2
- 208000020460 mucolipidosis II alpha/beta Diseases 0.000 claims 2
- 125000000160 oxazolidinyl group Chemical group 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- NVPICXQHSYQKGM-UHFFFAOYSA-N piperidine-1-carbonitrile Chemical compound N#CN1CCCCC1 NVPICXQHSYQKGM-UHFFFAOYSA-N 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 208000020016 psychiatric disease Diseases 0.000 claims 2
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims 2
- 125000002755 pyrazolinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 201000006473 pyruvate decarboxylase deficiency Diseases 0.000 claims 2
- 208000015445 pyruvate dehydrogenase deficiency Diseases 0.000 claims 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 2
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 2
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 2
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 claims 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 2
- 125000001984 thiazolidinyl 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
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 2
- JUYZCGUFQHIZRK-HXUWFJFHSA-N (3R)-3-[5-(3-cyanophenyl)-1,3-benzoxazol-2-yl]-3-fluoropiperidine-1-carbonitrile Chemical compound C(#N)C=1C=C(C=CC=1)C=1C=CC2=C(N=C(O2)[C@@]2(CN(CCC2)C#N)F)C=1 JUYZCGUFQHIZRK-HXUWFJFHSA-N 0.000 claims 1
- MNIYJNFACORUIG-HXUWFJFHSA-N (3R)-3-fluoro-3-[5-(3-phenylphenyl)-1,3,4-oxadiazol-2-yl]piperidine-1-carbonitrile Chemical compound C1(=CC(=CC=C1)C1=NN=C(O1)[C@@]1(CN(CCC1)C#N)F)C1=CC=CC=C1 MNIYJNFACORUIG-HXUWFJFHSA-N 0.000 claims 1
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 claims 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims 1
- DREJBWDIFYBZNH-UHFFFAOYSA-N 2-(4-phenyl-1H-benzimidazol-2-yl)morpholine-4-carbonitrile Chemical compound C1(=CC=CC=C1)C1=CC=CC=2NC(=NC=21)C1CN(CCO1)C#N DREJBWDIFYBZNH-UHFFFAOYSA-N 0.000 claims 1
- CAJFCTOHBOXOFN-LJQANCHMSA-N 2-[2-[(3R)-1-cyano-3-fluoropiperidin-3-yl]-1,3-benzoxazol-5-yl]pyridine-4-carbonitrile Chemical compound C(#N)N1C[C@@](CCC1)(F)C=1OC2=C(N=1)C=C(C=C2)C=1C=C(C#N)C=CN=1 CAJFCTOHBOXOFN-LJQANCHMSA-N 0.000 claims 1
- DNOKTXIUOJZGFA-GOSISDBHSA-N 2-[2-[(3R)-1-cyano-3-fluoropiperidin-3-yl]-1,3-benzoxazol-5-yl]pyrimidine-4-carbonitrile Chemical compound C(#N)N1C[C@@](CCC1)(F)C=1OC2=C(N=1)C=C(C=C2)C1=NC=CC(=N1)C#N DNOKTXIUOJZGFA-GOSISDBHSA-N 0.000 claims 1
- NQWNRPILMUFZSC-UHFFFAOYSA-N 2-[3-(3-phenylphenyl)-1H-1,2,4-triazol-5-yl]morpholine-4-carbonitrile Chemical compound N#CN1CCOC(C1)c1nc(n[nH]1)-c1cccc(c1)-c1ccccc1 NQWNRPILMUFZSC-UHFFFAOYSA-N 0.000 claims 1
- CDFCFWRRZSFOLS-UHFFFAOYSA-N 2-[4-(3-cyanophenyl)-1H-benzimidazol-2-yl]morpholine-4-carbonitrile Chemical compound C(#N)C=1C=C(C=CC=1)C1=CC=CC=2NC(=NC=21)C1CN(CCO1)C#N CDFCFWRRZSFOLS-UHFFFAOYSA-N 0.000 claims 1
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 claims 1
- CZYYVGVELOGAEB-UHFFFAOYSA-N 3-(1h-imidazol-5-yl)benzonitrile Chemical compound N#CC1=CC=CC(C=2NC=NC=2)=C1 CZYYVGVELOGAEB-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
- QTVATDZCAUZTNN-UHFFFAOYSA-N 3-[4-(2-phenoxyphenyl)-1,3-oxazol-2-yl]piperidine-1-carbonitrile Chemical compound O(C1=CC=CC=C1)C1=C(C=CC=C1)C=1N=C(OC=1)C1CN(CCC1)C#N QTVATDZCAUZTNN-UHFFFAOYSA-N 0.000 claims 1
- KBBNLFSLFLQZJW-UHFFFAOYSA-N 3-[4-(3-cyanophenyl)-1H-benzimidazol-2-yl]piperidine-1-carbonitrile Chemical compound C(#N)C=1C=C(C=CC=1)C1=CC=CC=2NC(=NC=21)C1CN(CCC1)C#N KBBNLFSLFLQZJW-UHFFFAOYSA-N 0.000 claims 1
- GCXMPVYWTNQRMX-UHFFFAOYSA-N 3-[4-(3-phenylphenyl)-1,3-oxazol-2-yl]piperidine-1-carbonitrile Chemical compound N#CN1CCCC(C1)c1nc(co1)-c1cccc(c1)-c1ccccc1 GCXMPVYWTNQRMX-UHFFFAOYSA-N 0.000 claims 1
- MXIOYUQPEMGLKO-UHFFFAOYSA-N 3-[6-(3-cyanophenyl)-[1,3]oxazolo[4,5-b]pyridin-2-yl]-3-fluoropiperidine-1-carbonitrile Chemical compound C(#N)C=1C=C(C=CC=1)C=1C=C2C(=NC=1)N=C(O2)C1(CN(CCC1)C#N)F MXIOYUQPEMGLKO-UHFFFAOYSA-N 0.000 claims 1
- ZDBVUTDCCAWUJF-UHFFFAOYSA-N 3-[6-(3-cyanophenyl)-[1,3]oxazolo[5,4-b]pyridin-2-yl]-3-fluoropiperidine-1-carbonitrile Chemical compound C(#N)C=1C=C(C=CC=1)C=1C=C2C(=NC=1)OC(=N2)C1(CN(CCC1)C#N)F ZDBVUTDCCAWUJF-UHFFFAOYSA-N 0.000 claims 1
- FQGIUHKVWDUNIX-UHFFFAOYSA-N 3-fluoro-3-[5-(4-phenylphenyl)-1,3,4-oxadiazol-2-yl]piperidine-1-carbonitrile Chemical compound C1(=CC=C(C=C1)C1=NN=C(O1)C1(CN(CCC1)C#N)F)C1=CC=CC=C1 FQGIUHKVWDUNIX-UHFFFAOYSA-N 0.000 claims 1
- LJDUVQHJIZBPOY-UHFFFAOYSA-N 3-fluoro-3-[6-(1H-pyrazol-5-yl)-1H-benzimidazol-2-yl]piperidine-1-carbonitrile Chemical compound N1N=CC=C1C=1C=CC2=C(NC(=N2)C2(CN(CCC2)C#N)F)C=1 LJDUVQHJIZBPOY-UHFFFAOYSA-N 0.000 claims 1
- ZGEMGDYXGLAYJB-LJQANCHMSA-N 4-[2-[5-[(3R)-1-cyano-3-fluoropiperidin-3-yl]-1,3,4-oxadiazol-2-yl]pyridin-4-yl]pyridine-2-carbonitrile Chemical compound F[C@@]1(CCCN(C1)C#N)C1=NN=C(O1)C1=NC=CC(=C1)C1=CC(=NC=C1)C#N ZGEMGDYXGLAYJB-LJQANCHMSA-N 0.000 claims 1
- BJAIDFQUKYOIGM-LJQANCHMSA-N 4-[4-[5-[(3R)-1-cyano-3-fluoropiperidin-3-yl]-1,3,4-oxadiazol-2-yl]pyridin-2-yl]pyridine-2-carbonitrile Chemical compound F[C@@]1(CCCN(C1)C#N)C1=NN=C(O1)C1=CC(=NC=C1)C1=CC(=NC=C1)C#N BJAIDFQUKYOIGM-LJQANCHMSA-N 0.000 claims 1
- XHLKOHSAWQPOFO-UHFFFAOYSA-N 5-phenyl-1h-imidazole Chemical compound N1C=NC=C1C1=CC=CC=C1 XHLKOHSAWQPOFO-UHFFFAOYSA-N 0.000 claims 1
- YRTYXUCVSHRVTO-GOSISDBHSA-N 6-[2-[(3R)-1-cyano-3-fluoropiperidin-3-yl]-1,3-benzoxazol-5-yl]pyrimidine-4-carbonitrile Chemical compound C(#N)N1C[C@@](CCC1)(F)C=1OC2=C(N=1)C=C(C=C2)C1=CC(=NC=N1)C#N YRTYXUCVSHRVTO-GOSISDBHSA-N 0.000 claims 1
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims 1
- 208000036022 Alpers' disease Diseases 0.000 claims 1
- 208000023434 Alpers-Huttenlocher syndrome Diseases 0.000 claims 1
- 102100026882 Alpha-synuclein Human genes 0.000 claims 1
- 208000018084 Bone neoplasm Diseases 0.000 claims 1
- 208000003174 Brain Neoplasms Diseases 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 101150072353 CAPN3 gene Proteins 0.000 claims 1
- 102100032539 Calpain-3 Human genes 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 208000031229 Cardiomyopathies Diseases 0.000 claims 1
- 206010008025 Cerebellar ataxia Diseases 0.000 claims 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims 1
- 208000021075 Creatine deficiency syndrome Diseases 0.000 claims 1
- 206010067889 Dementia with Lewy bodies Diseases 0.000 claims 1
- 102000015782 Electron Transport Complex III Human genes 0.000 claims 1
- 108010024882 Electron Transport Complex III Proteins 0.000 claims 1
- 208000024658 Epilepsy syndrome Diseases 0.000 claims 1
- 208000002877 Epileptic Syndromes Diseases 0.000 claims 1
- 206010016654 Fibrosis Diseases 0.000 claims 1
- 201000011240 Frontotemporal dementia Diseases 0.000 claims 1
- 208000009796 Gangliosidoses Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 101001083553 Homo sapiens Hydroxyacyl-coenzyme A dehydrogenase, mitochondrial Proteins 0.000 claims 1
- 102100030358 Hydroxyacyl-coenzyme A dehydrogenase, mitochondrial Human genes 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims 1
- 201000002832 Lewy body dementia Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 206010072930 Mucolipidosis type IV Diseases 0.000 claims 1
- 208000000149 Multiple Sulfatase Deficiency Disease Diseases 0.000 claims 1
- 208000034578 Multiple myelomas Diseases 0.000 claims 1
- 208000036572 Myoclonic epilepsy Diseases 0.000 claims 1
- 208000002537 Neuronal Ceroid-Lipofuscinoses Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 206010033799 Paralysis Diseases 0.000 claims 1
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 108010090931 Proto-Oncogene Proteins c-bcl-2 Proteins 0.000 claims 1
- 102000013535 Proto-Oncogene Proteins c-bcl-2 Human genes 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 201000007737 Retinal degeneration Diseases 0.000 claims 1
- 208000007014 Retinitis pigmentosa Diseases 0.000 claims 1
- 208000017460 Sialidosis type 2 Diseases 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 1
- 102000005262 Sulfatase Human genes 0.000 claims 1
- 208000024313 Testicular Neoplasms Diseases 0.000 claims 1
- 206010057644 Testis cancer Diseases 0.000 claims 1
- 235000018936 Vitellaria paradoxa Nutrition 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004450 alkenylene group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 108090000185 alpha-Synuclein Proteins 0.000 claims 1
- GOPDFXUMARJJEA-UHFFFAOYSA-N amino(nitro)azanide Chemical compound N[N-][N+]([O-])=O GOPDFXUMARJJEA-UHFFFAOYSA-N 0.000 claims 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims 1
- 230000005775 apoptotic pathway Effects 0.000 claims 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 1
- 210000000601 blood cell Anatomy 0.000 claims 1
- 229960004203 carnitine Drugs 0.000 claims 1
- 210000004027 cell Anatomy 0.000 claims 1
- 208000015114 central nervous system disease Diseases 0.000 claims 1
- 201000008609 cerebral creatine deficiency syndrome Diseases 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 230000001149 cognitive effect Effects 0.000 claims 1
- 230000003920 cognitive function Effects 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- CVSVTCORWBXHQV-UHFFFAOYSA-N creatine Chemical compound NC(=[NH2+])N(C)CC([O-])=O CVSVTCORWBXHQV-UHFFFAOYSA-N 0.000 claims 1
- 230000000120 cytopathologic effect Effects 0.000 claims 1
- 230000007423 decrease Effects 0.000 claims 1
- 230000007547 defect Effects 0.000 claims 1
- 230000007850 degeneration Effects 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 201000009028 early myoclonic encephalopathy Diseases 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- WCDWBPCFGJXFJZ-UHFFFAOYSA-N etanidazole Chemical group OCCNC(=O)CN1C=CN=C1[N+]([O-])=O WCDWBPCFGJXFJZ-UHFFFAOYSA-N 0.000 claims 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims 1
- 239000000835 fiber Substances 0.000 claims 1
- 230000004761 fibrosis Effects 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 201000006440 gangliosidosis Diseases 0.000 claims 1
- 206010017758 gastric cancer Diseases 0.000 claims 1
- 201000010536 head and neck cancer Diseases 0.000 claims 1
- 208000014829 head and neck neoplasm Diseases 0.000 claims 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 208000006443 lactic acidosis Diseases 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 201000011540 mitochondrial DNA depletion syndrome 4a Diseases 0.000 claims 1
- 208000012268 mitochondrial disease Diseases 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- BOQOXLAQTDFJKU-UHFFFAOYSA-N morpholine-4-carbonitrile Chemical compound N#CN1CCOCC1 BOQOXLAQTDFJKU-UHFFFAOYSA-N 0.000 claims 1
- 230000004899 motility Effects 0.000 claims 1
- 208000020468 mucolipidosis III alpha/beta Diseases 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 230000003387 muscular Effects 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 208000031225 myocardial ischemia Diseases 0.000 claims 1
- DTPSXFMGMQOVTG-UHFFFAOYSA-N n-[4-[3-(2-aminocyclopropyl)phenoxy]-1-(benzylamino)-1-oxobutan-2-yl]benzamide Chemical compound NC1CC1C1=CC=CC(OCCC(NC(=O)C=2C=CC=CC=2)C(=O)NCC=2C=CC=CC=2)=C1 DTPSXFMGMQOVTG-UHFFFAOYSA-N 0.000 claims 1
- 101150022123 ncl-1 gene Proteins 0.000 claims 1
- 210000005036 nerve Anatomy 0.000 claims 1
- 230000002232 neuromuscular Effects 0.000 claims 1
- 201000008051 neuronal ceroid lipofuscinosis Diseases 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
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 208000021090 palsy Diseases 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000000750 progressive effect Effects 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 230000001568 sexual effect Effects 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 108060007951 sulfatase Proteins 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 230000002123 temporal effect Effects 0.000 claims 1
- 201000003120 testicular cancer Diseases 0.000 claims 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims 1
- 210000001519 tissue Anatomy 0.000 claims 1
- 125000004306 triazinyl group Chemical group 0.000 claims 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 1
- 208000014001 urinary system disease Diseases 0.000 claims 1
- 201000010866 very long chain acyl-CoA dehydrogenase deficiency Diseases 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1616511.0A GB201616511D0 (en) | 2016-09-29 | 2016-09-29 | Novel compounds |
| GB1616511.0 | 2016-09-29 | ||
| PCT/GB2017/052882 WO2018060691A1 (en) | 2016-09-29 | 2017-09-27 | Cyano-subtituted heterocycles with activity as inhibitors of usp30 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019532945A JP2019532945A (ja) | 2019-11-14 |
| JP2019532945A5 true JP2019532945A5 (enExample) | 2020-11-12 |
| JP7044769B2 JP7044769B2 (ja) | 2022-03-30 |
Family
ID=57571048
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019516577A Active JP7044769B2 (ja) | 2016-09-29 | 2017-09-27 | Ｕｓｐ３０の阻害剤としての活性を有するシアノ置換複素環 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US10927110B2 (enExample) |
| EP (1) | EP3519397B1 (enExample) |
| JP (1) | JP7044769B2 (enExample) |
| CN (1) | CN109790148B (enExample) |
| GB (1) | GB201616511D0 (enExample) |
| TW (1) | TWI766882B (enExample) |
| WO (1) | WO2018060691A1 (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| EP3433246B1 (en) | 2016-03-24 | 2022-05-04 | Mission Therapeutics Limited | 1-cyano-pyrrolidine derivatives as dbu inhibitors |
| 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 |
| CN110831936B (zh) | 2017-06-20 | 2023-03-28 | 特殊治疗有限公司 | 具有dub抑制剂活性的取代氰基吡咯烷 |
| WO2019071073A1 (en) | 2017-10-06 | 2019-04-11 | Forma Therapeutics, Inc. | INHIBITION OF THE SPECIFIC PEPTIDASE OF UBIQUITIN |
| ES2988920T3 (es) | 2018-05-17 | 2024-11-22 | Forma Therapeutics Inc | Compuestos bicíclicos fusionados útiles como inhibidores de la peptidasa 30 específica de ubiquitina |
| 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 |
| AU2019356011B2 (en) | 2018-10-05 | 2025-02-06 | Forma Therapeutics, Inc. | Fused pyrrolines which act as Ubiquitin-Specific Protease 30 (USP30) inhibitors |
| CN120698983A (zh) | 2018-12-20 | 2025-09-26 | C4医药公司 | 靶向蛋白降解 |
| GB201905375D0 (en) | 2019-04-16 | 2019-05-29 | Mission Therapeutics Ltd | Novel compounds |
| GB201905371D0 (en) | 2019-04-16 | 2019-05-29 | Mission Therapeutics Ltd | Novel compounds |
| GB201912674D0 (en) | 2019-09-04 | 2019-10-16 | Mission Therapeutics Ltd | Novel compounds |
| CN110759902B (zh) | 2019-11-01 | 2022-04-22 | 海南一龄医疗产业发展有限公司 | Set8赖氨酸甲基转移酶抑制剂及其制备方法和用途 |
| MX2022012578A (es) | 2020-04-08 | 2022-11-07 | Mission Therapeutics Ltd | N-cianopirrolidinas con actividad como inhibidores de usp30. |
| EP4157834B1 (en) | 2020-05-28 | 2024-07-03 | Mission Therapeutics Limited | 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 |
| IL298710A (en) * | 2020-06-04 | 2023-02-01 | Mission Therapeutics Ltd | N-cyanopyrrolidines with activity as USP30 inhibitors |
| KR20230022215A (ko) | 2020-06-08 | 2023-02-14 | 미션 테라퓨틱스 엘티디 | 미토콘드리아 기능장애, 암 및 섬유증의 치료에 사용하기 위한 USP30 억제제로서 1-(5-(2-시아노피리딘-4-일)옥사졸-2-카보닐)-4-메틸헥사하이드로피롤로[3,4-b]피롤-5(1H)-카보니트릴 |
| GB202016800D0 (en) | 2020-10-22 | 2020-12-09 | Mission Therapeutics Ltd | Novel compounds |
| CN112920124B (zh) * | 2021-01-29 | 2024-03-01 | 安徽医科大学 | 一种嘧啶-2,4-二胺类化合物及其制备方法与应用 |
| CN118834147A (zh) * | 2021-09-22 | 2024-10-25 | 杭州天玑济世生物科技有限公司 | 一类具有萘胺结构的小分子化合物及其应用 |
| WO2023099561A1 (en) | 2021-12-01 | 2023-06-08 | Mission Therapeutics Limited | Substituted n-cyanopyrrolidines with activity as usp30 inhibitors |
| 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 (39)
| 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 |
| EP2152079A4 (en) | 2007-06-04 | 2011-03-09 | Avila Therapeutics Inc | HETEROCYCLIC COMPOUNDS AND USES THEREOF |
| WO2009026197A1 (en) | 2007-08-20 | 2009-02-26 | Glaxo Group Limited | Novel cathepsin c inhibitors and their use |
| CL2009000915A1 (es) | 2008-04-18 | 2010-04-16 | Glaxo Group Ltd | Compuestos derivados de 1-ciano-3-pirrolidinil-bencenosulfonamidas, inhibidores de catepsina c; composicion farmaceutica que comprende a dicho compuesto; y uso del compuesto para el tratamiento de una enfermedad pulmonar obstructiva cronica (copd). |
| WO2009129370A1 (en) | 2008-04-18 | 2009-10-22 | Glaxo Group Limited | Cathepsin c inhibitors |
| AR071369A1 (es) | 2008-04-18 | 2010-06-16 | Glaxo Group Ltd | Compuesto de 1- ciano-3-pirrolidinil-n-sustituido-sulfonamida, su uso para preparar un medicamento util para tratar una enfermedad pulmonar obstructiva cronica y composicion farmaceutica que lo comprende |
| EP2565186A1 (en) | 2011-09-02 | 2013-03-06 | Hybrigenics S.A. | Selective and reversible inhibitors of ubiquitin specific protease 7 |
| EP2773645A1 (en) | 2011-11-01 | 2014-09-10 | F.Hoffmann-La Roche Ag | Imidazopyridazine compounds |
| BR112015009624A2 (pt) * | 2012-11-02 | 2017-11-14 | Pfizer | inibidores de tirosina cinase de bruton |
| GB201309085D0 (en) | 2013-05-20 | 2013-07-03 | Redx Pharma Ltd | Compounds |
| PT3049417T (pt) | 2013-07-31 | 2019-01-24 | Merck Patent Gmbh | Piridinas, pirimidinas e pirazinas, como inibidores de btk e utilizações das mesmas |
| RU2019131017A (ru) * | 2013-10-21 | 2019-11-25 | Мерк Патент Гмбх | Соединения гетероарила в качестве ингибиторов btk и их применение |
| 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 |
| WO2015179190A1 (en) | 2014-05-19 | 2015-11-26 | Northeastern University | N-acylethanolamine hydrolyzing acid amidase (naaa) inhibitors and their use thereof |
| 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 |
| PT3461821T (pt) * | 2014-10-24 | 2020-08-05 | Bristol Myers Squibb Co | Compostos de indol carboxamida úteis como inibidores de quinase |
| HRP20210791T2 (hr) | 2015-03-30 | 2021-12-10 | Mission Therapeutics Limited | 1-cijano-pirolidin spojevi kao usp30 inhibitori |
| WO2016192074A1 (en) * | 2015-06-04 | 2016-12-08 | Merck Sharp & Dohme Corp. | Btk inhibitors |
| CN107849013B (zh) | 2015-07-14 | 2022-03-29 | 特殊治疗有限公司 | 作为dub抑制剂用于治疗癌症的氰基吡咯烷类 |
| 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 |
| EP3433246B1 (en) | 2016-03-24 | 2022-05-04 | Mission Therapeutics Limited | 1-cyano-pyrrolidine derivatives as dbu inhibitors |
| WO2017172989A1 (en) | 2016-03-30 | 2017-10-05 | Thorpe Steven Brandon | 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 |
| US10882843B2 (en) | 2016-05-16 | 2021-01-05 | Suzhou Sinovent Pharmaceuticals 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 |
| GB201708652D0 (en) | 2017-05-31 | 2017-07-12 | Mission Therapeutics Ltd | Novel compounds and uses |
| CN110831936B (zh) | 2017-06-20 | 2023-03-28 | 特殊治疗有限公司 | 具有dub抑制剂活性的取代氰基吡咯烷 |
-
2016
- 2016-09-29 GB GBGB1616511.0A patent/GB201616511D0/en not_active Ceased
-
2017
- 2017-09-26 TW TW106132939A patent/TWI766882B/zh active
- 2017-09-27 WO PCT/GB2017/052882 patent/WO2018060691A1/en not_active Ceased
- 2017-09-27 CN CN201780059951.8A patent/CN109790148B/zh active Active
- 2017-09-27 JP JP2019516577A patent/JP7044769B2/ja active Active
- 2017-09-27 US US16/336,363 patent/US10927110B2/en active Active
- 2017-09-27 EP EP17780148.7A patent/EP3519397B1/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2019532945A5 (enExample) | ||
| JP2019533659A5 (enExample) | ||
| JP7280928B2 (ja) | 脱ユビキチン化酵素（ｄｕｂ）阻害剤としてのスピロ縮合ピロリジン誘導体 | |
| JP6959332B2 (ja) | Ｕｓｐ３０の阻害剤としての活性を有するシアノピロリジン誘導体 | |
| JP7044769B2 (ja) | Ｕｓｐ３０の阻害剤としての活性を有するシアノ置換複素環 | |
| JP6898327B2 (ja) | 新規化合物 | |
| JP7084918B2 (ja) | Ｕｓｐ３０の阻害剤としての活性を有するシアノピロリジン誘導体 | |
| US10464919B2 (en) | Tricyclic derivative compound, method for preparing same, and pharmaceutical composition comprising same | |
| JP2019532938A5 (enExample) | ||
| JP7299837B2 (ja) | 化合物、組成物、および使用方法 | |
| JP2019507177A5 (enExample) | ||
| JP2019532950A5 (enExample) | ||
| JP2019509274A5 (enExample) | ||
| JP2021512153A (ja) | タンパク質分解のイミド系モジュレーターおよび使用方法 | |
| JP2019501142A5 (enExample) | ||
| JP2020521730A5 (enExample) | ||
| EP4204418A1 (en) | Rapidly accelerating fibrosarcoma protein degrading compounds and associated methods of use | |
| JP2019533659A (ja) | Ｕｓｐ３０の阻害剤としての活性を有するシアノ置換ヘテロ環 | |
| AU2018266640A1 (en) | Compounds and methods for treating bacterial infections | |
| JP2023528087A (ja) | ミトコンドリア機能不全、癌、及び線維症の治療に使用されるＵＳＰ３０阻害剤としての１－（５－（２－シアノピリジン－４－イル）オキサゾール－２－カルボニル）－４－メチルヘキサヒドロピロロ［３，４－ｂ］ピロール－５（１Ｈ）－カルボニトリル | |
| WO2014072930A2 (en) | Fused pyridine derivatives as antibacterial agents | |
| US20240067631A1 (en) | Pyrazole derivatives useful as nampt modulators | |
| US10487093B2 (en) | Heterocyclic compounds, in particular 2-oxo-4,4,5,5,6,6,7,7-octahydrobenzoxazole derivatives, and their use as antibacterial compounds | |
| WO2026027857A1 (en) | N-cyanopyrrolidine deviratives having activity as inhibiotrs of ubiquitin specific peptidase 30 | |
| JP2025517688A (ja) | Ｌｒｒｋ２阻害剤 |