JP2019532945A5 - - Google Patents
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- 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
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- -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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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