JP2018524367A5 - - Google Patents
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- Publication number
- JP2018524367A5 JP2018524367A5 JP2018501285A JP2018501285A JP2018524367A5 JP 2018524367 A5 JP2018524367 A5 JP 2018524367A5 JP 2018501285 A JP2018501285 A JP 2018501285A JP 2018501285 A JP2018501285 A JP 2018501285A JP 2018524367 A5 JP2018524367 A5 JP 2018524367A5
- Authority
- JP
- Japan
- Prior art keywords
- cyano
- pyrrolidine
- carbonitrile
- carbonyl
- carboxamide
- 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 22
- -1 methoxyethoxy Chemical group 0.000 claims 17
- 125000003118 aryl group Chemical group 0.000 claims 12
- 125000000623 heterocyclic group Chemical group 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 7
- 206010028980 Neoplasm Diseases 0.000 claims 6
- 201000011510 cancer Diseases 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 230000007812 deficiency Effects 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 125000002950 monocyclic group Chemical group 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 125000002947 alkylene group Chemical group 0.000 claims 4
- 125000005529 alkyleneoxy group Chemical group 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 208000011580 syndromic disease Diseases 0.000 claims 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 3
- 208000008955 Mucolipidoses Diseases 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims 2
- 208000035143 Bacterial infection Diseases 0.000 claims 2
- 208000014644 Brain disease Diseases 0.000 claims 2
- 206010058892 Carnitine deficiency Diseases 0.000 claims 2
- 208000002155 Cytochrome-c Oxidase Deficiency Diseases 0.000 claims 2
- 208000032274 Encephalopathy Diseases 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 101000619542 Homo sapiens E3 ubiquitin-protein ligase parkin Proteins 0.000 claims 2
- 201000002169 Mitochondrial myopathy Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 208000036142 Viral infection Diseases 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 208000022362 bacterial infectious disease Diseases 0.000 claims 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 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
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims 2
- 208000006443 lactic acidosis Diseases 0.000 claims 2
- 208000030159 metabolic disease 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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- 102000045222 parkin Human genes 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 208000024891 symptom Diseases 0.000 claims 2
- 208000016505 systemic primary carnitine deficiency disease Diseases 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 150000003573 thiols Chemical class 0.000 claims 2
- 125000001425 triazolyl group Chemical group 0.000 claims 2
- 230000009385 viral infection Effects 0.000 claims 2
- COKNKHWUKNJCMB-ZDUSSCGKSA-N (2S)-1-cyano-N-(5-cyano-4-phenyl-1,3-thiazol-2-yl)-N-methylpyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C)C=1SC(=C(N=1)C1=CC=CC=C1)C#N COKNKHWUKNJCMB-ZDUSSCGKSA-N 0.000 claims 1
- KCPHOFOOLGXKGK-HNNXBMFYSA-N (2S)-1-cyano-N-[3-(3-methoxyphenyl)-1,2-oxazol-5-yl]-N-methylpyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C)C1=CC(=NO1)C1=CC(=CC=C1)OC KCPHOFOOLGXKGK-HNNXBMFYSA-N 0.000 claims 1
- DCBBFYWGMDFIRP-AWEZNQCLSA-N (2S)-1-cyano-N-[4-(2-cyanopyridin-4-yl)-1,3-thiazol-2-yl]-N-methylpyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C)C=1SC=C(N=1)C1=CC(=NC=C1)C#N DCBBFYWGMDFIRP-AWEZNQCLSA-N 0.000 claims 1
- IJXKVEAWLXTUTE-AWEZNQCLSA-N (2S)-1-cyano-N-[4-(2-methoxyphenyl)-1,3-thiazol-2-yl]-N-methylpyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C)C=1SC=C(N=1)C1=C(C=CC=C1)OC IJXKVEAWLXTUTE-AWEZNQCLSA-N 0.000 claims 1
- LJALYPZMAKFPSM-HNNXBMFYSA-N (2S)-1-cyano-N-[4-(3-cyanophenyl)-1,3-thiazol-2-yl]-N-methylpyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C)C=1SC=C(N=1)C1=CC(=CC=C1)C#N LJALYPZMAKFPSM-HNNXBMFYSA-N 0.000 claims 1
- RPKFCLFVAACYOG-ZDUSSCGKSA-N (2S)-1-cyano-N-[4-(3-cyanophenyl)-5-fluoro-1,3-thiazol-2-yl]-N-methylpyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C)C=1SC(=C(N=1)C1=CC(=CC=C1)C#N)F RPKFCLFVAACYOG-ZDUSSCGKSA-N 0.000 claims 1
- VJDMCZGYBLAWAZ-INIZCTEOSA-N (2S)-1-cyano-N-[4-(3-ethylphenyl)-1,3-thiazol-2-yl]-N-methylpyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C)C=1SC=C(N=1)C1=CC(=CC=C1)CC VJDMCZGYBLAWAZ-INIZCTEOSA-N 0.000 claims 1
- HAGHQCDRXRUHJX-HNNXBMFYSA-N (2S)-1-cyano-N-[4-(3-methoxyphenyl)-1,3-thiazol-2-yl]-N-methylpyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C)C=1SC=C(N=1)C1=CC(=CC=C1)OC HAGHQCDRXRUHJX-HNNXBMFYSA-N 0.000 claims 1
- YVXVYNHRYPBFFU-AWEZNQCLSA-N (2S)-1-cyano-N-[4-(5-cyanopyridin-3-yl)-1,3-thiazol-2-yl]-N-methylpyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C)C=1SC=C(N=1)C=1C=NC=C(C=1)C#N YVXVYNHRYPBFFU-AWEZNQCLSA-N 0.000 claims 1
- KFVZUBKAWMNHOI-AWEZNQCLSA-N (2S)-1-cyano-N-[4-(6-cyano-3-ethoxypyridin-2-yl)-1,3-thiazol-2-yl]-N-methylpyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C)C=1SC=C(N=1)C1=NC(=CC=C1OCC)C#N KFVZUBKAWMNHOI-AWEZNQCLSA-N 0.000 claims 1
- AAKVUGNGGLMSKC-ZDUSSCGKSA-N (2S)-1-cyano-N-[4-(6-cyano-3-methoxypyridin-2-yl)-1,3-thiazol-2-yl]-N-methylpyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C)C=1SC=C(N=1)C1=NC(=CC=C1OC)C#N AAKVUGNGGLMSKC-ZDUSSCGKSA-N 0.000 claims 1
- ZUBBSKORVRCGAW-AWEZNQCLSA-N (2S)-1-cyano-N-[4-(6-cyano-3-methylpyridin-2-yl)-1,3-thiazol-2-yl]-N-methylpyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C)C=1SC=C(N=1)C1=NC(=CC=C1C)C#N ZUBBSKORVRCGAW-AWEZNQCLSA-N 0.000 claims 1
- SDXFIPRXASXHKJ-HNNXBMFYSA-N (2S)-1-cyano-N-[4-(6-cyano-5-ethoxypyridin-2-yl)-1,3-thiazol-2-yl]-N-methylpyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C)C=1SC=C(N=1)C1=NC(=C(C=C1)OCC)C#N SDXFIPRXASXHKJ-HNNXBMFYSA-N 0.000 claims 1
- APFKLZAHDDDAOH-AWEZNQCLSA-N (2S)-1-cyano-N-[4-(6-cyano-5-methoxypyridin-2-yl)-1,3-thiazol-2-yl]-N-methylpyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C)C=1SC=C(N=1)C1=NC(=C(C=C1)OC)C#N APFKLZAHDDDAOH-AWEZNQCLSA-N 0.000 claims 1
- AFWVFDKSXQAVKQ-HNNXBMFYSA-N (2S)-1-cyano-N-[4-(6-cyano-5-methylpyridin-2-yl)-1,3-thiazol-2-yl]-N-methylpyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C)C=1SC=C(N=1)C1=NC(=C(C=C1)C)C#N AFWVFDKSXQAVKQ-HNNXBMFYSA-N 0.000 claims 1
- RWUYLRLELHSDQH-AWEZNQCLSA-N (2S)-1-cyano-N-[4-(6-cyanopyridin-2-yl)-1,3-thiazol-2-yl]-N-methylpyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C)C=1SC=C(N=1)C1=NC(=CC=C1)C#N RWUYLRLELHSDQH-AWEZNQCLSA-N 0.000 claims 1
- WDNHBRPZDSJTGI-AWEZNQCLSA-N (2S)-1-cyano-N-[4-(6-cyanopyridin-2-yl)-5-ethyl-1,3-thiazol-2-yl]-N-methylpyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C)C=1SC(=C(N=1)C1=NC(=CC=C1)C#N)CC WDNHBRPZDSJTGI-AWEZNQCLSA-N 0.000 claims 1
- HHRMQBUASZODPH-AWEZNQCLSA-N (2S)-1-cyano-N-[4-(6-cyanopyridin-2-yl)-5-methyl-1,3-thiazol-2-yl]-N-methylpyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C)C=1SC(=C(N=1)C1=NC(=CC=C1)C#N)C HHRMQBUASZODPH-AWEZNQCLSA-N 0.000 claims 1
- JELYJKAQAGOBRO-INIZCTEOSA-N (2S)-1-cyano-N-[4-(6-cyclopropylpyridin-2-yl)-1,3-thiazol-2-yl]-N-methylpyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C)C=1SC=C(N=1)C1=NC(=CC=C1)C1CC1 JELYJKAQAGOBRO-INIZCTEOSA-N 0.000 claims 1
- FJGGYYJGDVVUII-ZDUSSCGKSA-N (2S)-1-cyano-N-[4-(6-methoxypyridin-2-yl)-1,3-thiazol-2-yl]-N-methylpyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C)C=1SC=C(N=1)C1=NC(=CC=C1)OC FJGGYYJGDVVUII-ZDUSSCGKSA-N 0.000 claims 1
- ITEZYZUQTSNQSW-INIZCTEOSA-N (2S)-1-cyano-N-[4-[3-(methoxymethyl)phenyl]-1,3-thiazol-2-yl]-N-methylpyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C)C=1SC=C(N=1)C1=CC(=CC=C1)COC ITEZYZUQTSNQSW-INIZCTEOSA-N 0.000 claims 1
- BBZPOMQJPPJJMO-HNNXBMFYSA-N (2S)-1-cyano-N-[4-[6-cyano-3-(2-methoxyethoxy)pyridin-2-yl]-1,3-thiazol-2-yl]-N-methylpyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C)C=1SC=C(N=1)C1=NC(=CC=C1OCCOC)C#N BBZPOMQJPPJJMO-HNNXBMFYSA-N 0.000 claims 1
- FFNWQIMPGVAHBV-INIZCTEOSA-N (2S)-1-cyano-N-[4-[6-cyano-5-(dimethylamino)pyridin-2-yl]-1,3-thiazol-2-yl]-N-methylpyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C)C=1SC=C(N=1)C1=NC(=C(C=C1)N(C)C)C#N FFNWQIMPGVAHBV-INIZCTEOSA-N 0.000 claims 1
- JAIBYYLRJLKSSA-HNNXBMFYSA-N (2S)-1-cyano-N-ethyl-N-(4-phenyl-1,3-thiazol-2-yl)pyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C=1SC=C(N=1)C1=CC=CC=C1)CC JAIBYYLRJLKSSA-HNNXBMFYSA-N 0.000 claims 1
- NWIHLTTYGVLQQC-AWEZNQCLSA-N (2S)-1-cyano-N-methyl-N-(1-phenylpyrazol-3-yl)pyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C1=NN(C=C1)C1=CC=CC=C1)C NWIHLTTYGVLQQC-AWEZNQCLSA-N 0.000 claims 1
- LRPSPLJSJDKUIB-AWEZNQCLSA-N (2S)-1-cyano-N-methyl-N-(3-phenyl-1,2-oxazol-5-yl)pyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C1=CC(=NO1)C1=CC=CC=C1)C LRPSPLJSJDKUIB-AWEZNQCLSA-N 0.000 claims 1
- XYJWIHFCSQUHLU-AWEZNQCLSA-N (2S)-1-cyano-N-methyl-N-(4-phenyl-1,3-thiazol-2-yl)pyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C=1SC=C(N=1)C1=CC=CC=C1)C XYJWIHFCSQUHLU-AWEZNQCLSA-N 0.000 claims 1
- QNESVFTZDYIHNM-NSHDSACASA-N (2S)-1-cyano-N-methyl-N-(4-propan-2-yl-1,3-thiazol-2-yl)pyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C)C=1SC=C(N=1)C(C)C QNESVFTZDYIHNM-NSHDSACASA-N 0.000 claims 1
- FAJFRTTWIMGORN-ZDUSSCGKSA-N (2S)-1-cyano-N-methyl-N-(4-pyridin-2-yl-1,3-thiazol-2-yl)pyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C=1SC=C(N=1)C1=NC=CC=C1)C FAJFRTTWIMGORN-ZDUSSCGKSA-N 0.000 claims 1
- UVROMVXOLVZJBN-ZDUSSCGKSA-N (2S)-1-cyano-N-methyl-N-(4-pyridin-3-yl-1,3-thiazol-2-yl)pyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C=1SC=C(N=1)C=1C=NC=CC=1)C UVROMVXOLVZJBN-ZDUSSCGKSA-N 0.000 claims 1
- NJZNESGNKPSFFK-ZDUSSCGKSA-N (2S)-1-cyano-N-methyl-N-(4-pyridin-4-yl-1,3-thiazol-2-yl)pyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C=1SC=C(N=1)C1=CC=NC=C1)C NJZNESGNKPSFFK-ZDUSSCGKSA-N 0.000 claims 1
- KNCJNJOLZXCRRY-ZDUSSCGKSA-N (2S)-1-cyano-N-methyl-N-(5-phenyl-1,2-oxazol-3-yl)pyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C1=NOC(=C1)C1=CC=CC=C1)C KNCJNJOLZXCRRY-ZDUSSCGKSA-N 0.000 claims 1
- XIDYNFKSCDNYHH-ZDUSSCGKSA-N (2S)-1-cyano-N-methyl-N-(5-phenyl-1,3-thiazol-2-yl)pyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C=1SC(=CN=1)C1=CC=CC=C1)C XIDYNFKSCDNYHH-ZDUSSCGKSA-N 0.000 claims 1
- XQZCEIALIBSWOY-HNNXBMFYSA-N (2S)-1-cyano-N-methyl-N-[4-(6-propan-2-yloxypyridin-2-yl)-1,3-thiazol-2-yl]pyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C)C=1SC=C(N=1)C1=NC(=CC=C1)OC(C)C XQZCEIALIBSWOY-HNNXBMFYSA-N 0.000 claims 1
- OZUQOMQSCJENAA-KFJBMODSSA-N (2S)-1-cyano-N-methyl-N-[4-(oxolan-3-yl)-1,3-thiazol-2-yl]pyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C=1SC=C(N=1)C1COCC1)C OZUQOMQSCJENAA-KFJBMODSSA-N 0.000 claims 1
- JQYNODAUGQIMPL-AWEZNQCLSA-N (2S)-1-cyano-N-methyl-N-[4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]pyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C=1SC=C(N=1)C1=CC(=CC=C1)C(F)(F)F)C JQYNODAUGQIMPL-AWEZNQCLSA-N 0.000 claims 1
- TXCMDMSYSGEVDO-INIZCTEOSA-N (2S)-1-cyano-N-methyl-N-[4-[3-[methyl(methylsulfonyl)amino]phenyl]-1,3-thiazol-2-yl]pyrrolidine-2-carboxamide Chemical compound C(#N)N1[C@@H](CCC1)C(=O)N(C=1SC=C(N=1)C1=CC(=CC=C1)N(S(=O)(=O)C)C)C TXCMDMSYSGEVDO-INIZCTEOSA-N 0.000 claims 1
- XCEQUYZBRPULKA-HNNXBMFYSA-N (2S)-2-(1-phenyl-5,6-dihydropyrrolo[3,2-c]pyrazole-4-carbonyl)pyrrolidine-1-carbonitrile Chemical compound C1(=CC=CC=C1)N1N=CC2=C1CCN2C(=O)[C@H]1N(CCC1)C#N XCEQUYZBRPULKA-HNNXBMFYSA-N 0.000 claims 1
- RPNXKHUIZNCHOE-AWEZNQCLSA-N (2S)-2-(4-ethoxy-2,3-dihydroindole-1-carbonyl)pyrrolidine-1-carbonitrile Chemical compound C(C)OC1=C2CCN(C2=CC=C1)C(=O)[C@H]1N(CCC1)C#N RPNXKHUIZNCHOE-AWEZNQCLSA-N 0.000 claims 1
- GHESLAQUATUPKG-IBGZPJMESA-N (2S)-2-(4-phenyl-1,3-dihydroisoindole-2-carbonyl)pyrrolidine-1-carbonitrile Chemical compound C1(=CC=CC=C1)C1=C2CN(CC2=CC=C1)C(=O)[C@H]1N(CCC1)C#N GHESLAQUATUPKG-IBGZPJMESA-N 0.000 claims 1
- GDWRBPHQNJJHCB-IBGZPJMESA-N (2S)-2-(4-phenyl-2,3-dihydroindole-1-carbonyl)pyrrolidine-1-carbonitrile Chemical compound C1(=CC=CC=C1)C1=C2CCN(C2=CC=C1)C(=O)[C@H]1N(CCC1)C#N GDWRBPHQNJJHCB-IBGZPJMESA-N 0.000 claims 1
- UEOUYNRYGPLQPF-WMCAAGNKSA-N (2S)-2-(4-pyrazolidin-3-yl-2,3-dihydroindole-1-carbonyl)pyrrolidine-1-carbonitrile Chemical compound C1C[C@H](N(C1)C#N)C(=O)N2CCC3=C(C=CC=C32)C4CCNN4 UEOUYNRYGPLQPF-WMCAAGNKSA-N 0.000 claims 1
- HIUWPHSAUQMWQZ-SFHVURJKSA-N (2S)-2-(4-pyridin-2-yl-2,3-dihydroindole-1-carbonyl)pyrrolidine-1-carbonitrile Chemical compound N1=C(C=CC=C1)C1=C2CCN(C2=CC=C1)C(=O)[C@H]1N(CCC1)C#N HIUWPHSAUQMWQZ-SFHVURJKSA-N 0.000 claims 1
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- CRFZMUGEOKSLSK-INIZCTEOSA-N tert-butyl (2S)-2-[[5-(3-methoxyphenyl)-1,2-oxazol-3-yl]-methylcarbamoyl]pyrrolidine-1-carboxylate Chemical compound COC=1C=C(C=CC=1)C1=CC(=NO1)N(C(=O)[C@H]1N(CCC1)C(=O)OC(C)(C)C)C CRFZMUGEOKSLSK-INIZCTEOSA-N 0.000 claims 1
- KNMIHEMZRYEGMW-RDJZCZTQSA-N tert-butyl (2S,4S)-4-methoxy-2-[methyl-(4-phenyl-1,3-thiazol-2-yl)carbamoyl]pyrrolidine-1-carboxylate Chemical compound CO[C@H]1C[C@H](N(C1)C(=O)OC(C)(C)C)C(N(C=1SC=C(N=1)C1=CC=CC=C1)C)=O KNMIHEMZRYEGMW-RDJZCZTQSA-N 0.000 claims 1
- 210000001550 testis Anatomy 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 210000001519 tissue Anatomy 0.000 claims 1
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 1
- 201000010866 very long chain acyl-CoA dehydrogenase deficiency Diseases 0.000 claims 1
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| WO2012040527A2 (en) | 2010-09-24 | 2012-03-29 | The Regents Of The University Of Michigan | Deubiquitinase inhibitors and methods for use of the same |
| RU2666530C2 (ru) * | 2012-01-12 | 2018-09-11 | Йейл Юниверсити | Соединения и способы усиления деградации белков-мишеней и других полипептидов с помощью е3 убиквитин лигазы |
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| GB201521109D0 (en) | 2015-11-30 | 2016-01-13 | Mission Therapeutics Ltd | Novel compounds |
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