JP2019533659A5 - - Google Patents
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- 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
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- 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
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| EP1492536B1 (de) | 2002-03-30 | 2012-05-09 | Boehringer Ingelheim Pharma GmbH & Co.KG | 4- ( n-phenylamino ) -chinazoline/chinoline als tyrosinkinaseinhibitoren |
| ATE502936T1 (de) | 2005-04-11 | 2011-04-15 | Almirall Sa | 2, 6-di-(hetero-)aryl-4-amido-pyrimidine als adenosin-rezeptor-antagonisten |
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| CN105008344B (zh) | 2012-11-02 | 2017-07-25 | 辉瑞公司 | 布鲁顿氏酪氨酸激酶抑制剂 |
| MX367085B (es) | 2013-07-31 | 2019-08-05 | Merck Patent Gmbh | Piridinas, pirimidinas y pirazinas como inhibidores de tirosina cinasa de bruton e inhibidores y usos de las mismas. |
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