JP2019533659A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2019533659A5 JP2019533659A5 JP2019518253A JP2019518253A JP2019533659A5 JP 2019533659 A5 JP2019533659 A5 JP 2019533659A5 JP 2019518253 A JP2019518253 A JP 2019518253A JP 2019518253 A JP2019518253 A JP 2019518253A JP 2019533659 A5 JP2019533659 A5 JP 2019533659A5
- Authority
- JP
- Japan
- Prior art keywords
- carboxamide
- cyano
- morpholine
- phenyl
- fluoropiperidine
- 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
- 150000001875 compounds Chemical class 0.000 claims 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 11
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 229910052757 nitrogen Inorganic materials 0.000 claims 9
- -1 nitro, hydroxyl Chemical group 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- 208000011580 syndromic disease Diseases 0.000 claims 7
- 206010028980 Neoplasm Diseases 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 230000007812 deficiency Effects 0.000 claims 6
- 125000002950 monocyclic group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 125000001153 fluoro group Chemical group F* 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 239000001301 oxygen Substances 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
- 125000002619 bicyclic group Chemical group 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 239000011593 sulfur Substances 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 208000008955 Mucolipidoses Diseases 0.000 claims 3
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- PDHMTOPDYYPOLL-UHFFFAOYSA-N 1-cyano-N-[4-(3-cyanophenyl)pyridin-2-yl]-3-fluoropiperidine-3-carboxamide Chemical compound C(#N)N1CC(CCC1)(C(=O)NC1=NC=CC(=C1)C1=CC(=CC=C1)C#N)F PDHMTOPDYYPOLL-UHFFFAOYSA-N 0.000 claims 2
- 206010058892 Carnitine deficiency Diseases 0.000 claims 2
- 206010009944 Colon cancer Diseases 0.000 claims 2
- 101000619542 Homo sapiens E3 ubiquitin-protein ligase parkin Proteins 0.000 claims 2
- 208000001769 Multiple Acyl Coenzyme A Dehydrogenase Deficiency Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 208000029742 colonic neoplasm Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 208000006443 lactic acidosis Diseases 0.000 claims 2
- 230000004065 mitochondrial dysfunction Effects 0.000 claims 2
- 230000002438 mitochondrial effect Effects 0.000 claims 2
- 230000035772 mutation Effects 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 102000045222 parkin Human genes 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 208000016505 systemic primary carnitine deficiency disease Diseases 0.000 claims 2
- QAFBIEQHAMSQBB-OAHLLOKOSA-N (2R)-4-cyano-N-(4-phenylpyridin-2-yl)morpholine-2-carboxamide Chemical compound C(#N)N1C[C@@H](OCC1)C(=O)NC1=NC=CC(=C1)C1=CC=CC=C1 QAFBIEQHAMSQBB-OAHLLOKOSA-N 0.000 claims 1
- IJZANVYABZUAMF-MRXNPFEDSA-N (2R)-4-cyano-N-[4-(3-cyanophenyl)pyridin-2-yl]morpholine-2-carboxamide Chemical compound C(#N)N1C[C@@H](OCC1)C(=O)NC1=NC=CC(=C1)C1=CC(=CC=C1)C#N IJZANVYABZUAMF-MRXNPFEDSA-N 0.000 claims 1
- MDHNLPXYWGDMFU-GFCCVEGCSA-N (2R)-4-cyano-N-[5-(1H-pyrazol-5-yl)pyridin-2-yl]morpholine-2-carboxamide Chemical compound N1N=CC=C1C=1C=CC(=NC=1)NC(=O)[C@H]1CN(CCO1)C#N MDHNLPXYWGDMFU-GFCCVEGCSA-N 0.000 claims 1
- JTTWNWCAMBVTLE-OAHLLOKOSA-N (2R)-4-cyano-N-[6-(1H-indazol-4-yl)pyrimidin-4-yl]morpholine-2-carboxamide Chemical compound N1N=CC2=C(C=CC=C12)C1=CC(=NC=N1)NC(=O)[C@H]1CN(CCO1)C#N JTTWNWCAMBVTLE-OAHLLOKOSA-N 0.000 claims 1
- MKRLZXYXUMOECQ-MRXNPFEDSA-N (2R)-4-cyano-N-[6-(1H-pyrazol-4-yl)isoquinolin-3-yl]morpholine-2-carboxamide Chemical compound N1N=CC(=C1)C=1C=C2C=C(N=CC2=CC=1)NC(=O)[C@H]1CN(CCO1)C#N MKRLZXYXUMOECQ-MRXNPFEDSA-N 0.000 claims 1
- XFDNDNUPTKELNJ-OAHLLOKOSA-N (2R)-4-cyano-N-[6-(3-cyano-5-fluorophenyl)pyrimidin-4-yl]morpholine-2-carboxamide Chemical compound C(#N)N1C[C@@H](OCC1)C(=O)NC1=NC=NC(=C1)C1=CC(=CC(=C1)F)C#N XFDNDNUPTKELNJ-OAHLLOKOSA-N 0.000 claims 1
- FRBCJLSRRBATNS-OAHLLOKOSA-N (2R)-4-cyano-N-[6-(3-cyanophenyl)pyrimidin-4-yl]morpholine-2-carboxamide Chemical compound C(#N)N1C[C@@H](OCC1)C(=O)NC1=NC=NC(=C1)C1=CC(=CC=C1)C#N FRBCJLSRRBATNS-OAHLLOKOSA-N 0.000 claims 1
- HWVXKQCCYHHULG-OAHLLOKOSA-N (2R)-4-cyano-N-[6-(3-methoxyphenyl)pyrimidin-4-yl]morpholine-2-carboxamide Chemical compound C(#N)N1C[C@@H](OCC1)C(=O)NC1=NC=NC(=C1)C1=CC(=CC=C1)OC HWVXKQCCYHHULG-OAHLLOKOSA-N 0.000 claims 1
- PPHSDVSKLAXMNM-QGZVFWFLSA-N (2R)-4-cyano-N-[6-(3-propan-2-yloxyphenyl)pyrimidin-4-yl]morpholine-2-carboxamide Chemical compound C(#N)N1C[C@@H](OCC1)C(=O)NC1=NC=NC(=C1)C1=CC(=CC=C1)OC(C)C PPHSDVSKLAXMNM-QGZVFWFLSA-N 0.000 claims 1
- MRQLULRSIAOSIA-OAHLLOKOSA-N (2R)-4-cyano-N-[6-(4-cyanophenyl)pyrimidin-4-yl]morpholine-2-carboxamide Chemical compound C(#N)N1C[C@@H](OCC1)C(=O)NC1=NC=NC(=C1)C1=CC=C(C=C1)C#N MRQLULRSIAOSIA-OAHLLOKOSA-N 0.000 claims 1
- JEXORXLEQCUQPN-QGZVFWFLSA-N (2R)-4-cyano-N-[6-[3-(1H-pyrazol-4-yl)phenyl]pyrimidin-4-yl]morpholine-2-carboxamide Chemical compound N1N=CC(=C1)C=1C=C(C=CC=1)C1=CC(=NC=N1)NC(=O)[C@H]1CN(CCO1)C#N JEXORXLEQCUQPN-QGZVFWFLSA-N 0.000 claims 1
- XVYKBFYMKIHMAH-CQSZACIVSA-N (2R)-N-[5-(3-chlorophenyl)pyridazin-3-yl]-4-cyanomorpholine-2-carboxamide Chemical compound ClC=1C=C(C=CC=1)C=1C=C(N=NC=1)NC(=O)[C@H]1CN(CCO1)C#N XVYKBFYMKIHMAH-CQSZACIVSA-N 0.000 claims 1
- BZATZGIDAYLPHZ-CQSZACIVSA-N (2R)-N-[6-(3-carbamoylphenyl)pyrimidin-4-yl]-4-cyanomorpholine-2-carboxamide Chemical compound C(N)(=O)C=1C=C(C=CC=1)C1=CC(=NC=N1)NC(=O)[C@H]1CN(CCO1)C#N BZATZGIDAYLPHZ-CQSZACIVSA-N 0.000 claims 1
- VGLJNKJNGOGYKZ-CQSZACIVSA-N (2R)-N-[6-(3-chlorophenyl)pyrimidin-4-yl]-4-cyanomorpholine-2-carboxamide Chemical compound ClC=1C=C(C=CC=1)C1=CC(=NC=N1)NC(=O)[C@H]1CN(CCO1)C#N VGLJNKJNGOGYKZ-CQSZACIVSA-N 0.000 claims 1
- GLHAUGRZKVRQSR-CQSZACIVSA-N (2R)-N-[6-(4-chlorophenyl)pyrimidin-4-yl]-4-cyanomorpholine-2-carboxamide Chemical compound ClC1=CC=C(C=C1)C1=CC(=NC=N1)NC(=O)[C@H]1CN(CCO1)C#N GLHAUGRZKVRQSR-CQSZACIVSA-N 0.000 claims 1
- PQGCAEHYQCNOLW-KRWDZBQOSA-N (2S)-2-(5-phenyl-2,3-dihydropyrrolo[2,3-b]pyridine-1-carbonyl)morpholine-4-carbonitrile Chemical compound C1(=CC=CC=C1)C=1C=C2C(=NC=1)N(CC2)C(=O)[C@@H]1CN(CCO1)C#N PQGCAEHYQCNOLW-KRWDZBQOSA-N 0.000 claims 1
- QAFBIEQHAMSQBB-HNNXBMFYSA-N (2S)-4-cyano-N-(4-phenylpyridin-2-yl)morpholine-2-carboxamide Chemical compound C(#N)N1C[C@H](OCC1)C(=O)NC1=NC=CC(=C1)C1=CC=CC=C1 QAFBIEQHAMSQBB-HNNXBMFYSA-N 0.000 claims 1
- IJZANVYABZUAMF-INIZCTEOSA-N (2S)-4-cyano-N-[4-(3-cyanophenyl)pyridin-2-yl]morpholine-2-carboxamide Chemical compound C(#N)N1C[C@H](OCC1)C(=O)NC1=NC=CC(=C1)C1=CC(=CC=C1)C#N IJZANVYABZUAMF-INIZCTEOSA-N 0.000 claims 1
- LCMQOORJYXVJCE-OAHLLOKOSA-N (3R)-1-cyano-3-fluoro-N-(5-pyrazol-1-ylpyridin-2-yl)piperidine-3-carboxamide Chemical compound N1(N=CC=C1)C=1C=CC(=NC=1)NC(=O)[C@@]1(CN(CCC1)C#N)F LCMQOORJYXVJCE-OAHLLOKOSA-N 0.000 claims 1
- QATOLZMHKPMCNA-MRXNPFEDSA-N (3R)-1-cyano-3-fluoro-N-[1-[3-(trifluoromethoxy)phenyl]imidazol-4-yl]piperidine-3-carboxamide Chemical compound FC(F)(F)Oc1cccc(c1)-n1cnc(NC(=O)[C@@]2(F)CCCN(C2)C#N)c1 QATOLZMHKPMCNA-MRXNPFEDSA-N 0.000 claims 1
- OAOVSXRHXJDZDX-MRXNPFEDSA-N (3R)-1-cyano-3-fluoro-N-[1-[3-(trifluoromethyl)phenyl]imidazol-4-yl]piperidine-3-carboxamide Chemical compound FC(F)(F)c1cccc(c1)-n1cnc(NC(=O)[C@@]2(F)CCCN(C2)C#N)c1 OAOVSXRHXJDZDX-MRXNPFEDSA-N 0.000 claims 1
- DFXFOEDBVKMGNN-GOSISDBHSA-N (3R)-1-cyano-3-fluoro-N-[5-(1H-indazol-4-yl)pyrazin-2-yl]piperidine-3-carboxamide Chemical compound N1N=CC2=C(C=CC=C12)C=1N=CC(=NC=1)NC(=O)[C@@]1(CN(CCC1)C#N)F DFXFOEDBVKMGNN-GOSISDBHSA-N 0.000 claims 1
- RVKTZBJWSPPHBX-LJQANCHMSA-N (3R)-1-cyano-3-fluoro-N-[5-(1H-indazol-4-yl)pyridin-2-yl]piperidine-3-carboxamide Chemical compound N1N=CC2=C(C=CC=C12)C=1C=CC(=NC=1)NC(=O)[C@@]1(CN(CCC1)C#N)F RVKTZBJWSPPHBX-LJQANCHMSA-N 0.000 claims 1
- NGAZKIGQCYBXLE-GOSISDBHSA-N (3R)-1-cyano-3-fluoro-N-[5-(1H-indazol-7-yl)pyrazin-2-yl]piperidine-3-carboxamide Chemical compound N1N=CC2=CC=CC(=C12)C=1N=CC(=NC=1)NC(=O)[C@@]1(CN(CCC1)C#N)F NGAZKIGQCYBXLE-GOSISDBHSA-N 0.000 claims 1
- XAOOXRZEETUMFG-LJQANCHMSA-N (3R)-1-cyano-3-fluoro-N-[5-(1H-indazol-7-yl)pyridin-2-yl]piperidine-3-carboxamide Chemical compound N1N=CC2=CC=CC(=C12)C=1C=CC(=NC=1)NC(=O)[C@@]1(CN(CCC1)C#N)F XAOOXRZEETUMFG-LJQANCHMSA-N 0.000 claims 1
- DHIQXPPRUNBUGF-GOSISDBHSA-N (3R)-1-cyano-3-fluoro-N-[5-(1H-indazol-7-yl)pyrimidin-2-yl]piperidine-3-carboxamide Chemical compound F[C@@]1(CCCN(C1)C#N)C(=O)Nc1ncc(cn1)-c1cccc2cn[nH]c12 DHIQXPPRUNBUGF-GOSISDBHSA-N 0.000 claims 1
- XWZZQGSFSWUAQX-OAHLLOKOSA-N (3R)-1-cyano-3-fluoro-N-[5-(1H-pyrazol-5-yl)pyridin-2-yl]piperidine-3-carboxamide Chemical compound N1N=CC=C1C=1C=CC(=NC=1)NC(=O)[C@@]1(CN(CCC1)C#N)F XWZZQGSFSWUAQX-OAHLLOKOSA-N 0.000 claims 1
- YJNCJFZMAZBBFH-GOSISDBHSA-N (3R)-1-cyano-3-fluoro-N-[5-(1H-pyrazolo[3,4-c]pyridin-7-yl)pyridin-2-yl]piperidine-3-carboxamide Chemical compound N1N=CC=2C1=C(N=CC=2)C=1C=CC(=NC=1)NC(=O)[C@@]1(CN(CCC1)C#N)F YJNCJFZMAZBBFH-GOSISDBHSA-N 0.000 claims 1
- CKHPQHLGQDSEQF-GOSISDBHSA-N (3R)-1-cyano-3-fluoro-N-[6-(1H-indazol-4-yl)pyridazin-3-yl]piperidine-3-carboxamide Chemical compound N1N=CC2=C(C=CC=C12)C1=CC=C(N=N1)NC(=O)[C@@]1(CN(CCC1)C#N)F CKHPQHLGQDSEQF-GOSISDBHSA-N 0.000 claims 1
- WJNRLQZQOGVBIE-MRXNPFEDSA-N (3R)-1-cyano-N-[1-(3-cyanophenyl)-1,2,4-triazol-3-yl]-3-fluoropiperidine-3-carboxamide Chemical compound C(#N)N1C[C@](CCC1)(C(=O)NC1=NN(C=N1)C1=CC(=CC=C1)C#N)F WJNRLQZQOGVBIE-MRXNPFEDSA-N 0.000 claims 1
- OXGXQNJXMGWTOX-QGZVFWFLSA-N (3R)-1-cyano-N-[1-(3-cyanophenyl)imidazol-4-yl]-3-fluoropiperidine-3-carboxamide Chemical compound C(#N)N1C[C@](CCC1)(C(=O)NC=1N=CN(C=1)C1=CC(=CC=C1)C#N)F OXGXQNJXMGWTOX-QGZVFWFLSA-N 0.000 claims 1
- NXIXHDVRCMUPTE-MRXNPFEDSA-N (3R)-1-cyano-N-[1-(3-cyanophenyl)triazol-4-yl]-3-fluoropiperidine-3-carboxamide Chemical compound C(#N)N1C[C@](CCC1)(C(=O)NC=1N=NN(C=1)C1=CC(=CC=C1)C#N)F NXIXHDVRCMUPTE-MRXNPFEDSA-N 0.000 claims 1
- VOZPNGOVUPKNNO-QGZVFWFLSA-N (3R)-1-cyano-N-[4-(3-cyanophenyl)-1,3-oxazol-2-yl]-3-fluoropiperidine-3-carboxamide Chemical compound C(#N)N1C[C@](CCC1)(C(=O)NC=1OC=C(N=1)C1=CC(=CC=C1)C#N)F VOZPNGOVUPKNNO-QGZVFWFLSA-N 0.000 claims 1
- DMGYXWZYKYHVBH-MRXNPFEDSA-N (3R)-N-[3-(3-chlorophenyl)-1,2-oxazol-5-yl]-1-cyano-3-fluoropiperidine-3-carboxamide Chemical compound ClC=1C=C(C=CC=1)C1=NOC(=C1)NC(=O)[C@@]1(CN(CCC1)C#N)F DMGYXWZYKYHVBH-MRXNPFEDSA-N 0.000 claims 1
- AFZXGXRVUJGVLW-MRXNPFEDSA-N (3R)-N-[5-(3-chlorophenyl)-1,2-oxazol-3-yl]-1-cyano-3-fluoropiperidine-3-carboxamide Chemical compound ClC=1C=C(C=CC=1)C1=CC(=NO1)NC(=O)[C@@]1(CN(CCC1)C#N)F AFZXGXRVUJGVLW-MRXNPFEDSA-N 0.000 claims 1
- JDTOVBDRZVGBHY-KRWDZBQOSA-N (3S)-1-cyano-N-[4-(3-cyanophenyl)pyridin-2-yl]piperidine-3-carboxamide Chemical compound C(#N)N1C[C@H](CCC1)C(=O)NC1=NC=CC(=C1)C1=CC(=CC=C1)C#N JDTOVBDRZVGBHY-KRWDZBQOSA-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
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims 1
- PRXXTXLLQZKRMW-UHFFFAOYSA-N 1-cyano-3-fluoro-N-(1-phenylimidazol-4-yl)piperidine-3-carboxamide Chemical compound C(#N)N1CC(CCC1)(C(=O)NC=1N=CN(C=1)C1=CC=CC=C1)F PRXXTXLLQZKRMW-UHFFFAOYSA-N 0.000 claims 1
- PIDBEMRGCJXCFZ-UHFFFAOYSA-N 1-cyano-3-fluoro-N-(4-phenylpyridin-2-yl)piperidine-3-carboxamide Chemical compound C(#N)N1CC(CCC1)(C(=O)NC1=NC=CC(=C1)C1=CC=CC=C1)F PIDBEMRGCJXCFZ-UHFFFAOYSA-N 0.000 claims 1
- XWZZQGSFSWUAQX-UHFFFAOYSA-N 1-cyano-3-fluoro-N-[5-(1H-pyrazol-5-yl)pyridin-2-yl]piperidine-3-carboxamide Chemical compound N1N=CC=C1C=1C=CC(=NC=1)NC(=O)C1(CN(CCC1)C#N)F XWZZQGSFSWUAQX-UHFFFAOYSA-N 0.000 claims 1
- XENQDMHLRQRNNF-UHFFFAOYSA-N 1-cyano-3-fluoro-N-[6-(1H-pyrazol-4-yl)-1,3-benzothiazol-2-yl]piperidine-3-carboxamide Chemical compound N1N=CC(=C1)C1=CC2=C(N=C(S2)NC(=O)C2(CN(CCC2)C#N)F)C=C1 XENQDMHLRQRNNF-UHFFFAOYSA-N 0.000 claims 1
- PAWCTLQUARPXTG-UHFFFAOYSA-N 1-cyano-5,5-difluoro-N-(1-phenylimidazol-4-yl)piperidine-3-carboxamide Chemical compound C(#N)N1CC(CC(C1)(F)F)C(=O)NC=1N=CN(C=1)C1=CC=CC=C1 PAWCTLQUARPXTG-UHFFFAOYSA-N 0.000 claims 1
- LAYXQNCDCMUZOO-UHFFFAOYSA-N 1-cyano-5,5-difluoro-N-[6-(1H-pyrazol-4-yl)-1,3-benzothiazol-2-yl]piperidine-3-carboxamide Chemical compound N1N=CC(=C1)C1=CC2=C(N=C(S2)NC(=O)C2CN(CC(C2)(F)F)C#N)C=C1 LAYXQNCDCMUZOO-UHFFFAOYSA-N 0.000 claims 1
- ARCUVVXHLCNTHP-UHFFFAOYSA-N 1-cyano-N-(1-phenylimidazol-4-yl)piperidine-3-carboxamide Chemical compound C(#N)N1CC(CCC1)C(=O)NC=1N=CN(C=1)C1=CC=CC=C1 ARCUVVXHLCNTHP-UHFFFAOYSA-N 0.000 claims 1
- DNLLABVYPLJSBO-UHFFFAOYSA-N 1-cyano-N-(4-phenylpyridin-2-yl)piperidine-3-carboxamide Chemical compound C(#N)N1CC(CCC1)C(=O)NC1=NC=CC(=C1)C1=CC=CC=C1 DNLLABVYPLJSBO-UHFFFAOYSA-N 0.000 claims 1
- NCJZSHMEHQBYCP-UHFFFAOYSA-N 1-cyano-N-(5-phenylpyridin-2-yl)piperidine-3-carboxamide Chemical compound C(#N)N1CC(CCC1)C(=O)NC1=NC=C(C=C1)C1=CC=CC=C1 NCJZSHMEHQBYCP-UHFFFAOYSA-N 0.000 claims 1
- AXIFCCZGQFOIJY-UHFFFAOYSA-N 1-cyano-N-[3-(3-cyanophenyl)-1,2-oxazol-5-yl]-3-fluoropiperidine-3-carboxamide Chemical compound C(#N)N1CC(CCC1)(C(=O)NC1=CC(=NO1)C1=CC(=CC=C1)C#N)F AXIFCCZGQFOIJY-UHFFFAOYSA-N 0.000 claims 1
- MDZZKPWYYWJXHT-UHFFFAOYSA-N 1-cyano-N-[5-(3-cyanophenyl)-1,2-oxazol-3-yl]-3-fluoropiperidine-3-carboxamide Chemical compound C(#N)N1CC(CCC1)(C(=O)NC1=NOC(=C1)C1=CC(=CC=C1)C#N)F MDZZKPWYYWJXHT-UHFFFAOYSA-N 0.000 claims 1
- YSPXRIXJFLGJQV-UHFFFAOYSA-N 1-cyano-N-[6-(3-cyanophenyl)pyrimidin-4-yl]-3-fluoropiperidine-3-carboxamide Chemical compound C(#N)N1CC(CCC1)(C(=O)NC1=NC=NC(=C1)C1=CC(=CC=C1)C#N)F YSPXRIXJFLGJQV-UHFFFAOYSA-N 0.000 claims 1
- OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 claims 1
- JFPOOBNIFQJMSH-UHFFFAOYSA-N 4-cyano-N-(3-phenylphenyl)morpholine-2-carboxamide Chemical compound C1(=CC(=CC=C1)NC(=O)C1CN(CCO1)C#N)C1=CC=CC=C1 JFPOOBNIFQJMSH-UHFFFAOYSA-N 0.000 claims 1
- BVHBQNYXBZCWFG-UHFFFAOYSA-N 4-cyano-N-(4-phenylphenyl)morpholine-2-carboxamide Chemical compound C1(=CC=C(C=C1)NC(=O)C1CN(CCO1)C#N)C1=CC=CC=C1 BVHBQNYXBZCWFG-UHFFFAOYSA-N 0.000 claims 1
- UYOMRDDVMMLAIJ-UHFFFAOYSA-N 4-cyano-N-(5-phenylpyridin-2-yl)morpholine-2-carboxamide Chemical compound C(#N)N1CC(OCC1)C(=O)NC1=NC=C(C=C1)C1=CC=CC=C1 UYOMRDDVMMLAIJ-UHFFFAOYSA-N 0.000 claims 1
- PPXJLVCDJSIBIO-UHFFFAOYSA-N 4-cyano-N-(6-phenylpyridin-3-yl)morpholine-2-carboxamide Chemical compound C(#N)N1CC(OCC1)C(=O)NC=1C=NC(=CC=1)C1=CC=CC=C1 PPXJLVCDJSIBIO-UHFFFAOYSA-N 0.000 claims 1
- JLUXWPATWDTYDH-UHFFFAOYSA-N 4-cyano-N-[6-(1H-pyrazol-4-yl)-1,3-benzothiazol-2-yl]morpholine-2-carboxamide Chemical compound N1N=CC(=C1)C1=CC2=C(N=C(S2)NC(=O)C2CN(CCO2)C#N)C=C1 JLUXWPATWDTYDH-UHFFFAOYSA-N 0.000 claims 1
- 208000023434 Alpers-Huttenlocher syndrome Diseases 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
- 208000018084 Bone neoplasm Diseases 0.000 claims 1
- 208000003174 Brain Neoplasms Diseases 0.000 claims 1
- 208000014644 Brain disease Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 208000031229 Cardiomyopathies Diseases 0.000 claims 1
- 108700005857 Carnitine palmitoyl transferase 1A deficiency Proteins 0.000 claims 1
- 208000005359 Carnitine palmitoyl transferase 1A deficiency 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
- 201000000915 Chronic Progressive External Ophthalmoplegia Diseases 0.000 claims 1
- 208000010354 Coenzyme Q10 deficiency Diseases 0.000 claims 1
- 208000021075 Creatine deficiency syndrome Diseases 0.000 claims 1
- 208000002155 Cytochrome-c Oxidase Deficiency Diseases 0.000 claims 1
- 208000011518 Danon disease 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
- 208000004986 Diffuse Cerebral Sclerosis of Schilder 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
- 208000032274 Encephalopathy 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
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 1
- 208000001500 Glycogen Storage Disease Type IIb Diseases 0.000 claims 1
- 208000035148 Glycogen storage disease due to LAMP-2 deficiency Diseases 0.000 claims 1
- 206010053185 Glycogen storage disease type II 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
- 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
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 201000002832 Lewy body dementia Diseases 0.000 claims 1
- 108700006159 Long-chain acyl-CoA dehydrogenase deficiency Proteins 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010025323 Lymphomas Diseases 0.000 claims 1
- 108700000232 Medium chain acyl CoA dehydrogenase deficiency Proteins 0.000 claims 1
- 206010058799 Mitochondrial encephalomyopathy Diseases 0.000 claims 1
- 201000002169 Mitochondrial myopathy Diseases 0.000 claims 1
- 208000000149 Multiple Sulfatase Deficiency Disease Diseases 0.000 claims 1
- 208000034578 Multiple myelomas Diseases 0.000 claims 1
- 208000035032 Multiple sulfatase deficiency 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
- 102100035196 POLG alternative reading frame Human genes 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 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
- 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
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 claims 1
- 208000021886 Pyruvate carboxylase deficiency Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 102100038376 Serine/threonine-protein kinase PINK1, mitochondrial Human genes 0.000 claims 1
- 208000005718 Stomach Neoplasms Diseases 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
- 125000004450 alkenylene group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 108090000185 alpha-Synuclein Proteins 0.000 claims 1
- 230000005775 apoptotic pathway Effects 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 210000000601 blood cell Anatomy 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 229960004203 carnitine Drugs 0.000 claims 1
- 201000004010 carnitine palmitoyltransferase I deficiency Diseases 0.000 claims 1
- 208000015114 central nervous system disease Diseases 0.000 claims 1
- 201000008609 cerebral creatine deficiency syndrome Diseases 0.000 claims 1
- 230000003920 cognitive function Effects 0.000 claims 1
- 230000000120 cytopathologic effect Effects 0.000 claims 1
- 230000007547 defect Effects 0.000 claims 1
- 230000007850 degeneration 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
- 239000003085 diluting agent Substances 0.000 claims 1
- 201000009028 early myoclonic encephalopathy Diseases 0.000 claims 1
- 230000004761 fibrosis Effects 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
- 208000014188 hereditary optic neuropathy Diseases 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 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
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 201000010901 lateral sclerosis Diseases 0.000 claims 1
- 231100000518 lethal Toxicity 0.000 claims 1
- 230000001665 lethal effect Effects 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 208000004687 long chain acyl-CoA dehydrogenase deficiency 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
- 208000003531 maternally-inherited Leigh syndrome Diseases 0.000 claims 1
- 208000005548 medium chain acyl-CoA dehydrogenase deficiency Diseases 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- 208000030159 metabolic disease Diseases 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 201000002697 mitochondrial DNA depletion syndrome Diseases 0.000 claims 1
- 201000011540 mitochondrial DNA depletion syndrome 4a Diseases 0.000 claims 1
- LSNOAQQZECGQNS-UHFFFAOYSA-N morpholine-2-carboxamide Chemical compound NC(=O)C1CNCCO1 LSNOAQQZECGQNS-UHFFFAOYSA-N 0.000 claims 1
- 208000005264 motor neuron disease Diseases 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 210000003205 muscle Anatomy 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
- 125000001624 naphthyl group Chemical group 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
- 210000000056 organ Anatomy 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- QAQREVBBADEHPA-IEXPHMLFSA-N propionyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 QAQREVBBADEHPA-IEXPHMLFSA-N 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 210000001525 retina Anatomy 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
- 201000003120 testicular cancer Diseases 0.000 claims 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 210000001519 tissue Anatomy 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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 |
|---|---|---|---|
| GB1616907.0 | 2016-10-05 | ||
| GBGB1616907.0A GB201616907D0 (en) | 2016-10-05 | 2016-10-05 | Novel Compounds |
| GB1710331.8 | 2017-06-28 | ||
| GBGB1710331.8A GB201710331D0 (en) | 2017-06-28 | 2017-06-28 | Novel compounds |
| PCT/GB2017/052971 WO2018065768A1 (en) | 2016-10-05 | 2017-10-04 | Cyano-substituted heterocycles with activity as inhibitors of usp30 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019533659A JP2019533659A (ja) | 2019-11-21 |
| JP2019533659A5 true JP2019533659A5 (OSRAM) | 2020-11-12 |
| JP7010935B2 JP7010935B2 (ja) | 2022-01-26 |
Family
ID=60083349
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019518253A Active JP7010935B2 (ja) | 2016-10-05 | 2017-10-04 | Ｕｓｐ３０の阻害剤としての活性を有するシアノ置換ヘテロ環 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US11370784B2 (OSRAM) |
| EP (1) | EP3523291B1 (OSRAM) |
| JP (1) | JP7010935B2 (OSRAM) |
| CN (1) | CN109803963B (OSRAM) |
| TW (1) | TWI771327B (OSRAM) |
| WO (1) | WO2018065768A1 (OSRAM) |
Families Citing this family (31)
| 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 |
| GB201604647D0 (en) | 2016-03-18 | 2016-05-04 | Mission Therapeutics Ltd | Novel compounds |
| GB201604638D0 (en) | 2016-03-18 | 2016-05-04 | Mission Therapeutics Ltd | Novel compounds |
| US11352339B2 (en) | 2016-03-24 | 2022-06-07 | Mission Therapeutics Limited | 1-cyano-pyrrolidine derivatives as DUB inhibitors |
| EP3519385B1 (en) | 2016-09-27 | 2020-11-18 | 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 |
| JP7129420B6 (ja) | 2017-03-30 | 2024-02-02 | エフ・ホフマン－ラ・ロシュ・アクチェンゲゼルシャフト | Ｈｐｋ１阻害剤としてのイソキノリン |
| 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 |
| KR102717600B1 (ko) | 2017-10-06 | 2024-10-15 | 포르마 세라퓨틱스 인크. | 유비퀴틴 특이적 펩티다제 30의 억제 |
| CN112513036B (zh) | 2018-05-17 | 2024-05-24 | 福马治疗有限公司 | 用作泛素特异性肽酶30抑制剂的稠合双环化合物 |
| WO2020023560A1 (en) | 2018-07-24 | 2020-01-30 | F. Hoffmann-La Roche Ag | Isoquinoline compounds and uses thereof |
| TW202024053A (zh) | 2018-10-02 | 2020-07-01 | 美商建南德克公司 | 異喹啉化合物及其用途 |
| US11612606B2 (en) | 2018-10-03 | 2023-03-28 | Genentech, Inc. | 8-aminoisoquinoline compounds and uses thereof |
| ES2945834T3 (es) | 2018-10-05 | 2023-07-07 | Forma Therapeutics Inc | Pirrolinas fusionadas que actúan como inhibidores de la proteasa 30 específica de ubiquitina (USP30) |
| CN120698985A (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 |
| EP4132925A1 (en) * | 2020-04-08 | 2023-02-15 | Mission Therapeutics Limited | N-cyanopyrrolidines with activity as usp30 inhibitors |
| KR20230016674A (ko) | 2020-05-28 | 2023-02-02 | 미션 테라퓨틱스 엘티디 | 미토콘드리아 기능장애의 치료를 위한 usp30 억제제로서 n-(1-시아노피롤리딘-3-일)-5-(3-(트라이플루오로메틸)페닐)옥사졸-2-카복스아미드 유도체 및 상응하는 옥사다이아졸 유도체 |
| JP2023529570A (ja) | 2020-06-04 | 2023-07-11 | ミッション セラピューティクス リミティド | Ｕｓｐ３０阻害剤としての活性を有するｎ－シアノピロリジン |
| SI4161929T1 (sl) | 2020-06-08 | 2025-10-30 | Mission Therapeutics Limited | 1-(5-(2-cianopiridin-4-il)oksazol-2-karbonil)-4-metilheksahidropirolo[3,4-b]pirol-5(1h)-karbonitril kot zaviralec usp30 za uporabo pri zdravljenju mitohondrijske disfunkcije, raka in fibroze |
| CN112029738B (zh) * | 2020-08-18 | 2022-04-29 | 浙江省人民医院 | 人parkin蛋白乙酰化及其在药物制备中的应用 |
| GB202016800D0 (en) | 2020-10-22 | 2020-12-09 | Mission Therapeutics Ltd | Novel compounds |
| JP2024544660A (ja) | 2021-12-01 | 2024-12-03 | ミッション セラピューティクス リミティド | Ｕｓｐ３０阻害剤としての活性を有する置換ｎ－シアノピロリジン |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI800481A7 (fi) * | 1980-02-19 | 1981-01-01 | Orion Yhtymae Oy | Menetelmä substituoitujen asyylipiperiidiinien valmistamiseksi. |
| US5861395A (en) * | 1996-09-13 | 1999-01-19 | Schering Corporation | Compounds useful for inhibition of farnesyl proteins transferase |
| US6635661B2 (en) * | 2000-05-25 | 2003-10-21 | Sepracor Inc. | Heterocyclic analgesic compounds and methods of use thereof |
| EP1272467A4 (en) | 2000-04-06 | 2003-05-07 | Merck Frosst Canada Inc | Cathepsin cysteine protease inhibitors |
| IL164167A0 (en) | 2002-03-30 | 2005-12-18 | Boehringer Ingelheim Pharma | 4-(N-phenylamino)-quinazolines/ quinolines as tyrosine kinase inhibitors |
| ATE502936T1 (de) * | 2005-04-11 | 2011-04-15 | Almirall Sa | 2, 6-di-(hetero-)aryl-4-amido-pyrimidine als adenosin-rezeptor-antagonisten |
| WO2010120854A1 (en) * | 2009-04-15 | 2010-10-21 | Glaxosmithkline Llc | Chemical compounds |
| MD20150035A2 (ro) | 2012-11-02 | 2015-10-31 | Pfizer Inc. | Inhibitori de tirozinkinaza Bruton |
| KR20160036053A (ko) | 2013-07-31 | 2016-04-01 | 메르크 파텐트 게엠베하 | Btk 저해제로서 피리딘, 피리미딘, 및 피라진, 및 이들의 용도 |
| GB201416754D0 (en) * | 2014-09-23 | 2014-11-05 | Mission Therapeutics Ltd | Novel compounds |
| AU2016240033B2 (en) | 2015-03-30 | 2020-04-16 | Mission Therapeutics Limited | 1-cyano-pyrrolidine compounds as USP30 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 |
| US11352339B2 (en) | 2016-03-24 | 2022-06-07 | Mission Therapeutics Limited | 1-cyano-pyrrolidine derivatives as DUB inhibitors |
| EP3519385B1 (en) | 2016-09-27 | 2020-11-18 | 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 |
| 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 |
-
2017
- 2017-10-02 TW TW106134051A patent/TWI771327B/zh active
- 2017-10-04 WO PCT/GB2017/052971 patent/WO2018065768A1/en not_active Ceased
- 2017-10-04 CN CN201780061706.0A patent/CN109803963B/zh active Active
- 2017-10-04 JP JP2019518253A patent/JP7010935B2/ja active Active
- 2017-10-04 EP EP17783973.5A patent/EP3523291B1/en active Active
- 2017-10-04 US US16/336,685 patent/US11370784B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2019533659A5 (OSRAM) | ||
| JP2019532938A5 (OSRAM) | ||
| JP2019532945A5 (OSRAM) | ||
| JP2019501142A5 (OSRAM) | ||
| JP2018524367A5 (OSRAM) | ||
| JP2020521730A5 (OSRAM) | ||
| US20220251041A1 (en) | 1-cyano-pyrrolidine compounds as usp30 inhibitors | |
| JP2019532950A5 (OSRAM) | ||
| JP2019504009A5 (OSRAM) | ||
| JP2019513135A5 (OSRAM) | ||
| JP2019509274A5 (OSRAM) | ||
| US11370784B2 (en) | Cyano-substituted heterocycles with activity as inhibitors of USP30 | |
| US10676479B2 (en) | Imidazolepyridine compounds and uses thereof | |
| 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 | |
| JP2019503362A5 (OSRAM) | ||
| JP2020524166A5 (OSRAM) | ||
| EP3519412A1 (en) | Cyanopyrrolidine derivatives with activity as inhibitors of usp30 | |
| US11919858B2 (en) | Aminonapthoquinone compounds and pharmaceutical composition for blocking ubiquitination-proteasome system in diseases | |
| JP2016514124A (ja) | 変異ｉｄｈの阻害薬としての３−ピリミジン−４−イル−オキサゾリジン−２−オン | |
| RU2012131124A (ru) | Птеридиноны как ингибиторы polo-подобных киназ | |
| JP2017508766A5 (OSRAM) | ||
| JP2017508766A (ja) | ＴｒｋＡキナーゼ阻害薬、その組成物および方法 | |
| JP2017528515A5 (OSRAM) | ||
| US10266535B2 (en) | Inhibitor of FLT3 kinase and use thereof | |
| CN101193878A (zh) | 实体肿瘤治疗剂 |