CA3072694A1 - 3-(1-oxoisoindolin-2-yl)piperidine-2,6-dione derivatives and uses thereof - Google Patents
3-(1-oxoisoindolin-2-yl)piperidine-2,6-dione derivatives and uses thereof Download PDFInfo
- Publication number
- CA3072694A1 CA3072694A1 CA3072694A CA3072694A CA3072694A1 CA 3072694 A1 CA3072694 A1 CA 3072694A1 CA 3072694 A CA3072694 A CA 3072694A CA 3072694 A CA3072694 A CA 3072694A CA 3072694 A1 CA3072694 A1 CA 3072694A1
- Authority
- CA
- Canada
- Prior art keywords
- dione
- piperidine
- piperidin
- oxoisoindolin
- methyl
- 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.)
- Pending
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- WENKGSGGXGQHSH-UHFFFAOYSA-N 3-(3-oxo-1h-isoindol-2-yl)piperidine-2,6-dione Chemical class C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O WENKGSGGXGQHSH-UHFFFAOYSA-N 0.000 title description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 540
- 101000599037 Homo sapiens Zinc finger protein Helios Proteins 0.000 claims abstract description 330
- 102100037796 Zinc finger protein Helios Human genes 0.000 claims abstract description 330
- 201000010099 disease Diseases 0.000 claims abstract description 279
- 150000001875 compounds Chemical class 0.000 claims abstract description 261
- 208000035475 disorder Diseases 0.000 claims abstract description 261
- 150000003839 salts Chemical class 0.000 claims abstract description 187
- 229940002612 prodrug Drugs 0.000 claims abstract description 177
- 239000000651 prodrug Substances 0.000 claims abstract description 177
- 239000012453 solvate Substances 0.000 claims abstract description 172
- 238000011282 treatment Methods 0.000 claims abstract description 90
- 238000000034 method Methods 0.000 claims abstract description 71
- 230000009467 reduction Effects 0.000 claims abstract description 46
- 125000005842 heteroatom Chemical group 0.000 claims description 254
- 229910052757 nitrogen Inorganic materials 0.000 claims description 251
- 229910052717 sulfur Inorganic materials 0.000 claims description 248
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 207
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 149
- 125000003118 aryl group Chemical group 0.000 claims description 127
- 125000004429 atom Chemical group 0.000 claims description 116
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 107
- 208000001894 Nasopharyngeal Neoplasms Diseases 0.000 claims description 104
- 206010061306 Nasopharyngeal cancer Diseases 0.000 claims description 104
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 102
- 206010028980 Neoplasm Diseases 0.000 claims description 88
- 208000003721 Triple Negative Breast Neoplasms Diseases 0.000 claims description 84
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 84
- 208000022679 triple-negative breast carcinoma Diseases 0.000 claims description 84
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 84
- 229910052736 halogen Chemical group 0.000 claims description 79
- 150000002367 halogens Chemical group 0.000 claims description 78
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 77
- 201000011510 cancer Diseases 0.000 claims description 73
- 125000001072 heteroaryl group Chemical group 0.000 claims description 73
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 67
- 206010009944 Colon cancer Diseases 0.000 claims description 63
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 50
- -1 3-(5-(1-(imidazopyrazin-3-ylmethyl)piperidin-4-yl)-1-oxoisoindolin-2-yl)piperidine-2,6-dione Chemical compound 0.000 claims description 50
- 239000003814 drug Substances 0.000 claims description 50
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 48
- 201000001441 melanoma Diseases 0.000 claims description 46
- 239000008194 pharmaceutical composition Substances 0.000 claims description 43
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 42
- 108091092878 Microsatellite Proteins 0.000 claims description 42
- 238000004519 manufacturing process Methods 0.000 claims description 40
- 125000001424 substituent group Chemical group 0.000 claims description 36
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 35
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 33
- 229910052760 oxygen Inorganic materials 0.000 claims description 32
- 208000002458 carcinoid tumor Diseases 0.000 claims description 23
- 201000011243 gastrointestinal stromal tumor Diseases 0.000 claims description 23
- 208000008732 thymoma Diseases 0.000 claims description 23
- 206010007275 Carcinoid tumour Diseases 0.000 claims description 22
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 20
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 230000028993 immune response Effects 0.000 claims description 17
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 16
- 230000002950 deficient Effects 0.000 claims description 16
- 230000002163 immunogen Effects 0.000 claims description 16
- KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical compound O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 claims description 13
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 239000003937 drug carrier Substances 0.000 claims description 9
- 125000002950 monocyclic group Chemical group 0.000 claims description 9
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 8
- 239000008177 pharmaceutical agent Substances 0.000 claims description 6
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 5
- 230000035755 proliferation Effects 0.000 claims description 5
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 4
- 238000002347 injection Methods 0.000 claims description 3
- 239000007924 injection Substances 0.000 claims description 3
- 230000000593 degrading effect Effects 0.000 claims description 2
- 238000001802 infusion Methods 0.000 claims description 2
- GLKCQJUUCIBRTC-UHFFFAOYSA-N 3-[3-oxo-6-[1-(1-phenylethyl)piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)C(C)C1=CC=CC=C1)C1C(NC(CC1)=O)=O GLKCQJUUCIBRTC-UHFFFAOYSA-N 0.000 claims 2
- CZEBEKGIRFFTCC-UHFFFAOYSA-N 3-[3-oxo-6-[1-(1H-pyrazol-5-ylmethyl)piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound N1N=C(C=C1)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O CZEBEKGIRFFTCC-UHFFFAOYSA-N 0.000 claims 2
- OFSKHJWCGFIJCE-UHFFFAOYSA-N 3-[3-oxo-6-[1-[(3-pyridin-2-yl-1H-pyrazol-5-yl)methyl]piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC1=NNC(=C1)C1=NC=CC=C1)C1C(NC(CC1)=O)=O OFSKHJWCGFIJCE-UHFFFAOYSA-N 0.000 claims 2
- BAWUHTSBEAGGSA-XJKSGUPXSA-N (3R)-3-[6-[(3R)-1-acetylpyrrolidin-3-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C)(=O)N1C[C@H](CC1)C=1C=C2CN(C(C2=CC=1)=O)[C@H]1C(NC(CC1)=O)=O BAWUHTSBEAGGSA-XJKSGUPXSA-N 0.000 claims 1
- KAJNVQAGLMPGCW-AUSIDOKSSA-N (3R)-3-[6-[(4R)-1-benzylazepan-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C1=CC=CC=C1)N1CC[C@@H](CCC1)C=1C=C2CN(C(C2=CC=1)=O)[C@H]1C(NC(CC1)=O)=O KAJNVQAGLMPGCW-AUSIDOKSSA-N 0.000 claims 1
- KAJNVQAGLMPGCW-WMZHIEFXSA-N (3R)-3-[6-[(4S)-1-benzylazepan-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C1=CC=CC=C1)N1CC[C@H](CCC1)C=1C=C2CN(C(C2=CC=1)=O)[C@H]1C(NC(CC1)=O)=O KAJNVQAGLMPGCW-WMZHIEFXSA-N 0.000 claims 1
- BAWUHTSBEAGGSA-BBRMVZONSA-N (3S)-3-[6-[(3R)-1-acetylpyrrolidin-3-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C)(=O)N1C[C@H](CC1)C=1C=C2CN(C(C2=CC=1)=O)[C@@H]1C(NC(CC1)=O)=O BAWUHTSBEAGGSA-BBRMVZONSA-N 0.000 claims 1
- KAJNVQAGLMPGCW-XXBNENTESA-N (3S)-3-[6-[(4R)-1-benzylazepan-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C1=CC=CC=C1)N1CC[C@@H](CCC1)C=1C=C2CN(C(C2=CC=1)=O)[C@@H]1C(NC(CC1)=O)=O KAJNVQAGLMPGCW-XXBNENTESA-N 0.000 claims 1
- KAJNVQAGLMPGCW-CVDCTZTESA-N (3S)-3-[6-[(4S)-1-benzylazepan-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C1=CC=CC=C1)N1CC[C@H](CCC1)C=1C=C2CN(C(C2=CC=1)=O)[C@@H]1C(NC(CC1)=O)=O KAJNVQAGLMPGCW-CVDCTZTESA-N 0.000 claims 1
- URBKCTSNYKHEPM-UHFFFAOYSA-N 2-[4-[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]piperidin-1-yl]-N-phenylacetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)C1CCN(CC1)CC(=O)NC1=CC=CC=C1)=O)=O URBKCTSNYKHEPM-UHFFFAOYSA-N 0.000 claims 1
- KIZAKWPMXFJRSX-UHFFFAOYSA-N 2-[4-[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]piperidin-1-yl]acetic acid Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)C1CCN(CC1)CC(=O)O)=O)=O KIZAKWPMXFJRSX-UHFFFAOYSA-N 0.000 claims 1
- IACWUKBYTLCAIJ-UHFFFAOYSA-N 2-[4-[[4-[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]piperidin-1-yl]methyl]phenoxy]acetonitrile Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)C1CCN(CC1)CC1=CC=C(OCC#N)C=C1)=O)=O IACWUKBYTLCAIJ-UHFFFAOYSA-N 0.000 claims 1
- ARHYWQBGKCRXLX-UHFFFAOYSA-N 2-[4-[[4-[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]piperidin-1-yl]methyl]phenyl]acetic acid Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)C1CCN(CC1)CC1=CC=C(C=C1)CC(=O)O)=O)=O ARHYWQBGKCRXLX-UHFFFAOYSA-N 0.000 claims 1
- RFTUDHBWVBMQLN-UHFFFAOYSA-N 2-[4-[[4-[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]piperidin-1-yl]methyl]phenyl]acetonitrile Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)C1CCN(CC1)CC1=CC=C(C=C1)CC#N)=O)=O RFTUDHBWVBMQLN-UHFFFAOYSA-N 0.000 claims 1
- QBMZYFZENKPGMG-UHFFFAOYSA-N 2-[[4-[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]piperidin-1-yl]methyl]benzonitrile Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)C1CCN(CC1)CC1=C(C#N)C=CC=C1)=O)=O QBMZYFZENKPGMG-UHFFFAOYSA-N 0.000 claims 1
- XYOJJXVTLBLFBR-UHFFFAOYSA-N 2-[[4-[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]piperidin-1-yl]methyl]pyrimidine-5-carbonitrile Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)C1CCN(CC1)CC1=NC=C(C=N1)C#N)=O)=O XYOJJXVTLBLFBR-UHFFFAOYSA-N 0.000 claims 1
- FYMRVPCFNQKGSJ-UHFFFAOYSA-N 3-[3-oxo-6-(1-phenylpiperidin-4-yl)-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)C1=CC=CC=C1)C1C(NC(CC1)=O)=O FYMRVPCFNQKGSJ-UHFFFAOYSA-N 0.000 claims 1
- WJEQLCOPUZEFIY-UHFFFAOYSA-N 3-[3-oxo-6-(1-propylpiperidin-4-yl)-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CCC)C1C(NC(CC1)=O)=O WJEQLCOPUZEFIY-UHFFFAOYSA-N 0.000 claims 1
- MZBHUPFYEJLFFG-UHFFFAOYSA-N 3-[3-oxo-6-[1-(1,2,3,4-tetrahydronaphthalen-1-ylmethyl)piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC1CCCC2=CC=CC=C12)C1C(NC(CC1)=O)=O MZBHUPFYEJLFFG-UHFFFAOYSA-N 0.000 claims 1
- FSXCMFBWADFMHQ-UHFFFAOYSA-N 3-[3-oxo-6-[1-(1,2-thiazol-5-ylmethyl)piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound S1N=CC=C1CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O FSXCMFBWADFMHQ-UHFFFAOYSA-N 0.000 claims 1
- GUFUYYSKZLUYKF-UHFFFAOYSA-N 3-[3-oxo-6-[1-(1,3-thiazol-2-ylmethyl)piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC=1SC=CN=1)C1C(NC(CC1)=O)=O GUFUYYSKZLUYKF-UHFFFAOYSA-N 0.000 claims 1
- YOYSGXAVHVOHAU-UHFFFAOYSA-N 3-[3-oxo-6-[1-(1,3-thiazol-4-ylmethyl)piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC=1N=CSC=1)C1C(NC(CC1)=O)=O YOYSGXAVHVOHAU-UHFFFAOYSA-N 0.000 claims 1
- LDODCLGLAFSXDS-UHFFFAOYSA-N 3-[3-oxo-6-[1-(1H-pyrazol-4-ylmethyl)piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound N1N=CC(=C1)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O LDODCLGLAFSXDS-UHFFFAOYSA-N 0.000 claims 1
- LTLCETZUQJLBQH-UHFFFAOYSA-N 3-[3-oxo-6-[1-(1H-pyrrol-3-ylmethyl)piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound N1C=C(C=C1)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O LTLCETZUQJLBQH-UHFFFAOYSA-N 0.000 claims 1
- GCXIWSITJVUNEZ-UHFFFAOYSA-N 3-[3-oxo-6-[1-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound N1C=C(C=2C1=NC=CC=2)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O GCXIWSITJVUNEZ-UHFFFAOYSA-N 0.000 claims 1
- ROJVCARTZWJSQB-UHFFFAOYSA-N 3-[3-oxo-6-[1-(1H-pyrrolo[2,3-b]pyridin-6-ylmethyl)piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound N1C=CC=2C1=NC(=CC=2)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O ROJVCARTZWJSQB-UHFFFAOYSA-N 0.000 claims 1
- SNOCYDFXRNHLGE-UHFFFAOYSA-N 3-[3-oxo-6-[1-(2,2,2-trifluoro-1-phenylethyl)piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)C(C(F)(F)F)C1=CC=CC=C1)C1C(NC(CC1)=O)=O SNOCYDFXRNHLGE-UHFFFAOYSA-N 0.000 claims 1
- LVBQBELCGFNMTA-UHFFFAOYSA-N 3-[3-oxo-6-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC(F)(F)F)C1C(NC(CC1)=O)=O LVBQBELCGFNMTA-UHFFFAOYSA-N 0.000 claims 1
- HAUKGCIDBKJGRU-UHFFFAOYSA-N 3-[3-oxo-6-[1-(2-phenylacetyl)piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)C(CC1=CC=CC=C1)=O)C1C(NC(CC1)=O)=O HAUKGCIDBKJGRU-UHFFFAOYSA-N 0.000 claims 1
- DJVAALWZOAMVJC-UHFFFAOYSA-N 3-[3-oxo-6-[1-(2-piperidin-1-ylethyl)piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CCN1CCCCC1)C1C(NC(CC1)=O)=O DJVAALWZOAMVJC-UHFFFAOYSA-N 0.000 claims 1
- YTJWRVYLFJZNPK-UHFFFAOYSA-N 3-[3-oxo-6-[1-(2-pyrrolidin-1-ylethyl)piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CCN1CCCC1)C1C(NC(CC1)=O)=O YTJWRVYLFJZNPK-UHFFFAOYSA-N 0.000 claims 1
- OTCSRCQQDSTOQQ-UHFFFAOYSA-N 3-[3-oxo-6-[1-(3,3,3-trifluoropropyl)piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CCC(F)(F)F)C1C(NC(CC1)=O)=O OTCSRCQQDSTOQQ-UHFFFAOYSA-N 0.000 claims 1
- JDSUENQLDTYMDU-UHFFFAOYSA-N 3-[3-oxo-6-[1-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-ylmethyl)piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC1=NN2C(CCCC2)=C1)C1C(NC(CC1)=O)=O JDSUENQLDTYMDU-UHFFFAOYSA-N 0.000 claims 1
- QHODFIPSFXGMNX-UHFFFAOYSA-N 3-[3-oxo-6-[1-(5,6,7,8-tetrahydronaphthalen-1-ylmethyl)piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC1=CC=CC=2CCCCC1=2)C1C(NC(CC1)=O)=O QHODFIPSFXGMNX-UHFFFAOYSA-N 0.000 claims 1
- XILHMWHPEXIGHT-UHFFFAOYSA-N 3-[3-oxo-6-[1-(5,6,7,8-tetrahydronaphthalen-2-ylmethyl)piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC1=CC=2CCCCC=2C=C1)C1C(NC(CC1)=O)=O XILHMWHPEXIGHT-UHFFFAOYSA-N 0.000 claims 1
- WKTQIWWGRFAUCD-UHFFFAOYSA-N 3-[3-oxo-6-[1-(pyrazolo[1,5-a]pyridin-4-ylmethyl)piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC=1C=2N(C=CC=1)N=CC=2)C1C(NC(CC1)=O)=O WKTQIWWGRFAUCD-UHFFFAOYSA-N 0.000 claims 1
- GPSKFRSMPJZVTA-UHFFFAOYSA-N 3-[3-oxo-6-[1-(pyrazolo[1,5-a]pyrimidin-6-ylmethyl)piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC=1C=NC=2N(C=1)N=CC=2)C1C(NC(CC1)=O)=O GPSKFRSMPJZVTA-UHFFFAOYSA-N 0.000 claims 1
- JBYLKRPFHBWHQN-UHFFFAOYSA-N 3-[3-oxo-6-[1-(pyridin-2-ylmethyl)piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC1=NC=CC=C1)C1C(NC(CC1)=O)=O JBYLKRPFHBWHQN-UHFFFAOYSA-N 0.000 claims 1
- JAQZEEJJMVEBNJ-UHFFFAOYSA-N 3-[3-oxo-6-[1-(pyridin-3-ylmethyl)piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC=1C=NC=CC=1)C1C(NC(CC1)=O)=O JAQZEEJJMVEBNJ-UHFFFAOYSA-N 0.000 claims 1
- CTUHAZWQSALVSM-UHFFFAOYSA-N 3-[3-oxo-6-[1-(pyridin-4-ylmethyl)piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC1=CC=NC=C1)C1C(NC(CC1)=O)=O CTUHAZWQSALVSM-UHFFFAOYSA-N 0.000 claims 1
- DYRNAGDUEBHJDZ-UHFFFAOYSA-N 3-[3-oxo-6-[1-(pyrimidin-2-ylmethyl)piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC1=NC=CC=N1)C1C(NC(CC1)=O)=O DYRNAGDUEBHJDZ-UHFFFAOYSA-N 0.000 claims 1
- XZYOAXROQCZIDO-UHFFFAOYSA-N 3-[3-oxo-6-[1-(pyrimidin-5-ylmethyl)piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC=1C=NC=NC=1)C1C(NC(CC1)=O)=O XZYOAXROQCZIDO-UHFFFAOYSA-N 0.000 claims 1
- FZGGGRLUBDQAAP-UHFFFAOYSA-N 3-[3-oxo-6-[1-(quinolin-2-ylmethyl)piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC1=NC2=CC=CC=C2C=C1)C1C(NC(CC1)=O)=O FZGGGRLUBDQAAP-UHFFFAOYSA-N 0.000 claims 1
- IHLGPTIDKIATFF-UHFFFAOYSA-N 3-[3-oxo-6-[1-(quinolin-4-ylmethyl)piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC1=CC=NC2=CC=CC=C12)C1C(NC(CC1)=O)=O IHLGPTIDKIATFF-UHFFFAOYSA-N 0.000 claims 1
- XOXXGODMPYXAPC-UHFFFAOYSA-N 3-[3-oxo-6-[1-(quinolin-8-ylmethyl)piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC=1C=CC=C2C=CC=NC=12)C1C(NC(CC1)=O)=O XOXXGODMPYXAPC-UHFFFAOYSA-N 0.000 claims 1
- RBXUJPNGIXZYFN-UHFFFAOYSA-N 3-[3-oxo-6-[1-(quinoxalin-6-ylmethyl)piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC=1C=C2N=CC=NC2=CC=1)C1C(NC(CC1)=O)=O RBXUJPNGIXZYFN-UHFFFAOYSA-N 0.000 claims 1
- DYVIFTWRNBHROW-UHFFFAOYSA-N 3-[3-oxo-6-[1-[(1-phenylpyrazol-4-yl)methyl]piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC=1C=NN(C=1)C1=CC=CC=C1)C1C(NC(CC1)=O)=O DYVIFTWRNBHROW-UHFFFAOYSA-N 0.000 claims 1
- UASFXRBDMBTBPZ-UHFFFAOYSA-N 3-[3-oxo-6-[1-[(1-propan-2-ylpyrazol-4-yl)methyl]piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C)(C)N1N=CC(=C1)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O UASFXRBDMBTBPZ-UHFFFAOYSA-N 0.000 claims 1
- JBWIFMLXJODUAD-UHFFFAOYSA-N 3-[3-oxo-6-[1-[(1-pyridin-3-ylpyrazol-4-yl)methyl]piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC=1C=NN(C=1)C=1C=NC=CC=1)C1C(NC(CC1)=O)=O JBWIFMLXJODUAD-UHFFFAOYSA-N 0.000 claims 1
- GLKCQJUUCIBRTC-LIXIDFRTSA-N 3-[3-oxo-6-[1-[(1R)-1-phenylethyl]piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)[C@H](C)C1=CC=CC=C1)C1C(NC(CC1)=O)=O GLKCQJUUCIBRTC-LIXIDFRTSA-N 0.000 claims 1
- GLKCQJUUCIBRTC-NVHKAFQKSA-N 3-[3-oxo-6-[1-[(1S)-1-phenylethyl]piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)[C@@H](C)C1=CC=CC=C1)C1C(NC(CC1)=O)=O GLKCQJUUCIBRTC-NVHKAFQKSA-N 0.000 claims 1
- DBXBUWWOEWFBNK-UHFFFAOYSA-N 3-[3-oxo-6-[1-[(2-oxo-1,3-dihydrobenzimidazol-5-yl)methyl]piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC1=CC2=C(NC(N2)=O)C=C1)C1C(NC(CC1)=O)=O DBXBUWWOEWFBNK-UHFFFAOYSA-N 0.000 claims 1
- DQUWKKBOYUGHKH-UHFFFAOYSA-N 3-[3-oxo-6-[1-[(2-phenylpyrazol-3-yl)methyl]piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC1=CC=NN1C1=CC=CC=C1)C1C(NC(CC1)=O)=O DQUWKKBOYUGHKH-UHFFFAOYSA-N 0.000 claims 1
- GLHKOKIPKBRHKI-UHFFFAOYSA-N 3-[3-oxo-6-[1-[(2-propan-2-ylpyrazol-3-yl)methyl]piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C)(C)N1N=CC=C1CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O GLHKOKIPKBRHKI-UHFFFAOYSA-N 0.000 claims 1
- RQGOGJJKBSOPDN-UHFFFAOYSA-N 3-[3-oxo-6-[1-[(2-pyridin-3-ylpyrazol-3-yl)methyl]piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC1=CC=NN1C=1C=NC=CC=1)C1C(NC(CC1)=O)=O RQGOGJJKBSOPDN-UHFFFAOYSA-N 0.000 claims 1
- SKORMNJHPLOCQN-UHFFFAOYSA-N 3-[3-oxo-6-[1-[(2-pyrrolidin-1-ylpyrimidin-5-yl)methyl]piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC=1C=NC(=NC=1)N1CCCC1)C1C(NC(CC1)=O)=O SKORMNJHPLOCQN-UHFFFAOYSA-N 0.000 claims 1
- PWAAXTDLVOKYNR-UHFFFAOYSA-N 3-[3-oxo-6-[1-[(2-thiophen-2-yl-1,3-thiazol-5-yl)methyl]piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC1=CN=C(S1)C=1SC=CC=1)C1C(NC(CC1)=O)=O PWAAXTDLVOKYNR-UHFFFAOYSA-N 0.000 claims 1
- LJJWRMILVQWBQQ-UHFFFAOYSA-N 3-[3-oxo-6-[1-[(3-propan-2-yloxyphenyl)methyl]piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C)(C)OC=1C=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=CC=1 LJJWRMILVQWBQQ-UHFFFAOYSA-N 0.000 claims 1
- GYAUSQGUCXWYGF-UHFFFAOYSA-N 3-[3-oxo-6-[1-[(3-pyrazol-1-ylphenyl)methyl]piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound N1(N=CC=C1)C=1C=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=CC=1 GYAUSQGUCXWYGF-UHFFFAOYSA-N 0.000 claims 1
- OBVIKDWKJAXHFY-UHFFFAOYSA-N 3-[3-oxo-6-[1-[(4-oxo-3H-thieno[3,2-d]pyrimidin-2-yl)methyl]piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC=1NC(C2=C(N=1)C=CS2)=O)C1C(NC(CC1)=O)=O OBVIKDWKJAXHFY-UHFFFAOYSA-N 0.000 claims 1
- DSCUTQDNZRVYJK-UHFFFAOYSA-N 3-[3-oxo-6-[1-[(4-phenylphenyl)methyl]piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C1(=CC=C(C=C1)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)C1=CC=CC=C1 DSCUTQDNZRVYJK-UHFFFAOYSA-N 0.000 claims 1
- JQHSCZWGEPHUPK-UHFFFAOYSA-N 3-[3-oxo-6-[1-[(4-propan-2-ylphenyl)methyl]piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C)(C)C1=CC=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C1 JQHSCZWGEPHUPK-UHFFFAOYSA-N 0.000 claims 1
- XEFLYXHQEVYYEH-UHFFFAOYSA-N 3-[3-oxo-6-[1-[(4-propan-2-ylsulfanylphenyl)methyl]piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C)(C)SC1=CC=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C1 XEFLYXHQEVYYEH-UHFFFAOYSA-N 0.000 claims 1
- FHRPTDRMRQJLQS-UHFFFAOYSA-N 3-[3-oxo-6-[1-[(4-propylphenyl)methyl]piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC1=CC=C(C=C1)CCC)C1C(NC(CC1)=O)=O FHRPTDRMRQJLQS-UHFFFAOYSA-N 0.000 claims 1
- FYHGDCNVRQYJDO-UHFFFAOYSA-N 3-[3-oxo-6-[1-[(4-pyrazol-1-ylphenyl)methyl]piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound N1(N=CC=C1)C1=CC=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C1 FYHGDCNVRQYJDO-UHFFFAOYSA-N 0.000 claims 1
- AYAVHUKJJLZTEL-UHFFFAOYSA-N 3-[3-oxo-6-[1-[(4-pyrrol-1-ylphenyl)methyl]piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound N1(C=CC=C1)C1=CC=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C1 AYAVHUKJJLZTEL-UHFFFAOYSA-N 0.000 claims 1
- GDTVCVLJQGKDFO-UHFFFAOYSA-N 3-[3-oxo-6-[1-[(4-pyrrolidin-1-ylphenyl)methyl]piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC1=CC=C(C=C1)N1CCCC1)C1C(NC(CC1)=O)=O GDTVCVLJQGKDFO-UHFFFAOYSA-N 0.000 claims 1
- RUYRPSNPCYIYPZ-UHFFFAOYSA-N 3-[3-oxo-6-[1-[(4-thiophen-3-ylphenyl)methyl]piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC1=CC=C(C=C1)C1=CSC=C1)C1C(NC(CC1)=O)=O RUYRPSNPCYIYPZ-UHFFFAOYSA-N 0.000 claims 1
- DCJCSGQZZJBTAW-UHFFFAOYSA-N 3-[3-oxo-6-[1-[(5-phenyl-1,3,4-oxadiazol-2-yl)methyl]piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC=1OC(=NN=1)C1=CC=CC=C1)C1C(NC(CC1)=O)=O DCJCSGQZZJBTAW-UHFFFAOYSA-N 0.000 claims 1
- CEURALOBJXIYIV-UHFFFAOYSA-N 3-[3-oxo-6-[1-[(5-phenyl-1H-pyrazol-4-yl)methyl]piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC=1C(=NNC=1)C1=CC=CC=C1)C1C(NC(CC1)=O)=O CEURALOBJXIYIV-UHFFFAOYSA-N 0.000 claims 1
- ZGQCTAYEKMUZPP-UHFFFAOYSA-N 3-[3-oxo-6-[1-[(5-propan-2-yloxypyridin-2-yl)methyl]piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C)(C)OC=1C=CC(=NC=1)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O ZGQCTAYEKMUZPP-UHFFFAOYSA-N 0.000 claims 1
- UTJOCVFKVQHGRR-UHFFFAOYSA-N 3-[3-oxo-6-[1-[(5-pyridin-3-yl-1H-pyrazol-4-yl)methyl]piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC=1C(=NNC=1)C=1C=NC=CC=1)C1C(NC(CC1)=O)=O UTJOCVFKVQHGRR-UHFFFAOYSA-N 0.000 claims 1
- DDNQUFJIBIWKLO-UHFFFAOYSA-N 3-[3-oxo-6-[1-[(6-propan-2-yloxypyridin-3-yl)methyl]piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C)(C)OC1=CC=C(C=N1)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O DDNQUFJIBIWKLO-UHFFFAOYSA-N 0.000 claims 1
- NIXUBNOAFMGPEC-UHFFFAOYSA-N 3-[3-oxo-6-[1-[[2-(trifluoromethoxy)phenyl]methyl]piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC1=C(C=CC=C1)OC(F)(F)F)C1C(NC(CC1)=O)=O NIXUBNOAFMGPEC-UHFFFAOYSA-N 0.000 claims 1
- SHBMSQSXKGUHIJ-UHFFFAOYSA-N 3-[3-oxo-6-[1-[[2-(trifluoromethyl)phenyl]methyl]piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC1=C(C=CC=C1)C(F)(F)F)C1C(NC(CC1)=O)=O SHBMSQSXKGUHIJ-UHFFFAOYSA-N 0.000 claims 1
- PATNWSQXRKVKMT-UHFFFAOYSA-N 3-[3-oxo-6-[1-[[3-(trifluoromethoxy)phenyl]methyl]piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC1=CC(=CC=C1)OC(F)(F)F)C1C(NC(CC1)=O)=O PATNWSQXRKVKMT-UHFFFAOYSA-N 0.000 claims 1
- CLOWVMVWZJLOQL-UHFFFAOYSA-N 3-[3-oxo-6-[1-[[4-(pyridin-2-ylmethoxy)phenyl]methyl]piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC1=CC=C(C=C1)OCC1=NC=CC=C1)C1C(NC(CC1)=O)=O CLOWVMVWZJLOQL-UHFFFAOYSA-N 0.000 claims 1
- SPEXMZKEMUILOA-UHFFFAOYSA-N 3-[3-oxo-6-[1-[[4-(trifluoromethoxy)phenyl]methyl]piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC1=CC=C(C=C1)OC(F)(F)F)C1C(NC(CC1)=O)=O SPEXMZKEMUILOA-UHFFFAOYSA-N 0.000 claims 1
- LTBGQYCRSMKZFE-UHFFFAOYSA-N 3-[3-oxo-6-[1-[[4-(trifluoromethyl)phenyl]methyl]piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC1=CC=C(C=C1)C(F)(F)F)C1C(NC(CC1)=O)=O LTBGQYCRSMKZFE-UHFFFAOYSA-N 0.000 claims 1
- PTFUPKGEWHHRAS-UHFFFAOYSA-N 3-[3-oxo-6-[1-[[5-(trifluoromethyl)pyridin-2-yl]methyl]piperidin-4-yl]-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC1=NC=C(C=C1)C(F)(F)F)C1C(NC(CC1)=O)=O PTFUPKGEWHHRAS-UHFFFAOYSA-N 0.000 claims 1
- IKMSYJHPGOWLIQ-UHFFFAOYSA-N 3-[6-(1,2,3,5,6,7,8,8a-octahydroindolizin-7-yl)-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C1CCN2CCC(CC12)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O IKMSYJHPGOWLIQ-UHFFFAOYSA-N 0.000 claims 1
- DYBUYHUAATVTOM-UHFFFAOYSA-N 3-[6-(1-acetyl-2,5-dihydropyrrol-3-yl)-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C)(=O)N1CC(=CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O DYBUYHUAATVTOM-UHFFFAOYSA-N 0.000 claims 1
- FDNDISZOTQRFLW-UHFFFAOYSA-N 3-[6-(1-acetyl-3,6-dihydro-2H-pyridin-4-yl)-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C)(=O)N1CCC(=CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O FDNDISZOTQRFLW-UHFFFAOYSA-N 0.000 claims 1
- KQKSZPKPTHSIJM-UHFFFAOYSA-N 3-[6-(1-acetyl-3,6-dihydro-2H-pyridin-5-yl)-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C)(=O)N1CC(=CCC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O KQKSZPKPTHSIJM-UHFFFAOYSA-N 0.000 claims 1
- ODHSWSXPLZDQHT-UHFFFAOYSA-N 3-[6-(1-acetylpiperidin-4-yl)-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C)(=O)N1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O ODHSWSXPLZDQHT-UHFFFAOYSA-N 0.000 claims 1
- QRWDIFDTPZXIKO-UHFFFAOYSA-N 3-[6-(1-benzyl-2,5-dihydropyrrol-3-yl)-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C1=CC=CC=C1)N1CC(=CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O QRWDIFDTPZXIKO-UHFFFAOYSA-N 0.000 claims 1
- KILGWHPUKBWHOY-UHFFFAOYSA-N 3-[6-(1-benzyl-2-methylpiperidin-4-yl)-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C1=CC=CC=C1)N1C(CC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)C KILGWHPUKBWHOY-UHFFFAOYSA-N 0.000 claims 1
- GINRDGRGHUJNHR-UHFFFAOYSA-N 3-[6-(1-benzyl-2-oxopiperidin-4-yl)-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C1=CC=CC=C1)N1C(CC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)=O GINRDGRGHUJNHR-UHFFFAOYSA-N 0.000 claims 1
- XKWBPLILDKHSTC-UHFFFAOYSA-N 3-[6-(1-benzyl-3,3-dimethylpiperidin-4-yl)-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C1=CC=CC=C1)N1CC(C(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)(C)C XKWBPLILDKHSTC-UHFFFAOYSA-N 0.000 claims 1
- VEOSIOSDKGPVEG-UHFFFAOYSA-N 3-[6-(1-benzyl-3,4-dihydro-2H-quinolin-4-yl)-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C1=CC=CC=C1)N1CCC(C2=CC=CC=C12)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O VEOSIOSDKGPVEG-UHFFFAOYSA-N 0.000 claims 1
- LNJHUYBFNKAGSV-UHFFFAOYSA-N 3-[6-(1-benzyl-3-methylpiperidin-4-yl)-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C1=CC=CC=C1)N1CC(C(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)C LNJHUYBFNKAGSV-UHFFFAOYSA-N 0.000 claims 1
- KAJNVQAGLMPGCW-UHFFFAOYSA-N 3-[6-(1-benzylazepan-4-yl)-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C1=CC=CC=C1)N1CCC(CCC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O KAJNVQAGLMPGCW-UHFFFAOYSA-N 0.000 claims 1
- OMISHRJQMYQPMG-UHFFFAOYSA-N 3-[6-(1-benzylpiperidin-4-yl)-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C1=CC=CC=C1)N1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O OMISHRJQMYQPMG-UHFFFAOYSA-N 0.000 claims 1
- OHKHFPDSTNDZET-UHFFFAOYSA-N 3-[6-(1-benzylpyrrolidin-3-yl)-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C1=CC=CC=C1)N1CC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O OHKHFPDSTNDZET-UHFFFAOYSA-N 0.000 claims 1
- HZOMXCTYEUEIIG-UHFFFAOYSA-N 3-[6-(1-ethylpiperidin-4-yl)-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C)N1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O HZOMXCTYEUEIIG-UHFFFAOYSA-N 0.000 claims 1
- XTYWOPNNGJRAKW-UHFFFAOYSA-N 3-[6-(1-methyl-2,3,6,7-tetrahydroazepin-4-yl)-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound CN1CCC(=CCC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O XTYWOPNNGJRAKW-UHFFFAOYSA-N 0.000 claims 1
- IENMSQYLYDYHQH-UHFFFAOYSA-N 3-[6-(1-methyl-3,6-dihydro-2H-pyridin-4-yl)-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound CN1CCC(=CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O IENMSQYLYDYHQH-UHFFFAOYSA-N 0.000 claims 1
- KQZHMAJTJMJLSN-UHFFFAOYSA-N 3-[6-(1-methylazepan-4-yl)-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound CN1CCC(CCC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O KQZHMAJTJMJLSN-UHFFFAOYSA-N 0.000 claims 1
- DHHGMHKDJFZRLQ-UHFFFAOYSA-N 3-[6-(8-azabicyclo[3.2.1]octan-3-yl)-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C12CC(CC(CC1)N2)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O DHHGMHKDJFZRLQ-UHFFFAOYSA-N 0.000 claims 1
- BAWIWVUMGKIEPC-UHFFFAOYSA-N 3-[6-(8-benzyl-8-azabicyclo[3.2.1]octan-3-yl)-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C1=CC=CC=C1)N1C2CC(CC1CC2)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O BAWIWVUMGKIEPC-UHFFFAOYSA-N 0.000 claims 1
- KQLVHPSDHDZTDV-UHFFFAOYSA-N 3-[6-(azepan-4-yl)-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound N1CCC(CCC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O KQLVHPSDHDZTDV-UHFFFAOYSA-N 0.000 claims 1
- KILGWHPUKBWHOY-WMAFBANVSA-N 3-[6-[(2R)-1-benzyl-2-methylpiperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C1=CC=CC=C1)N1[C@@H](CC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)C KILGWHPUKBWHOY-WMAFBANVSA-N 0.000 claims 1
- KILGWHPUKBWHOY-JVPSVYLMSA-N 3-[6-[(2S)-1-benzyl-2-methylpiperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C1=CC=CC=C1)N1[C@H](CC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)C KILGWHPUKBWHOY-JVPSVYLMSA-N 0.000 claims 1
- KAJNVQAGLMPGCW-HWYAHNCWSA-N 3-[6-[(4R)-1-benzylazepan-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C1=CC=CC=C1)N1CC[C@@H](CCC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O KAJNVQAGLMPGCW-HWYAHNCWSA-N 0.000 claims 1
- KQLVHPSDHDZTDV-ZGTOLYCTSA-N 3-[6-[(4R)-azepan-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound N1CC[C@@H](CCC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O KQLVHPSDHDZTDV-ZGTOLYCTSA-N 0.000 claims 1
- KAJNVQAGLMPGCW-HSTJUUNISA-N 3-[6-[(4S)-1-benzylazepan-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C1=CC=CC=C1)N1CC[C@H](CCC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O KAJNVQAGLMPGCW-HSTJUUNISA-N 0.000 claims 1
- KQLVHPSDHDZTDV-HKALDPMFSA-N 3-[6-[(4S)-azepan-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound N1CC[C@H](CCC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O KQLVHPSDHDZTDV-HKALDPMFSA-N 0.000 claims 1
- HXXJWEVZPRUIGJ-UHFFFAOYSA-N 3-[6-[1-(1,2,4-oxadiazol-3-ylmethyl)piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O1N=C(N=C1)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O HXXJWEVZPRUIGJ-UHFFFAOYSA-N 0.000 claims 1
- DBLPRIFINUMBEQ-UHFFFAOYSA-N 3-[6-[1-(1,2-oxazol-3-ylmethyl)piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O1N=C(C=C1)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O DBLPRIFINUMBEQ-UHFFFAOYSA-N 0.000 claims 1
- BCUAHBPXSNSQRT-UHFFFAOYSA-N 3-[6-[1-(1,3-benzothiazol-2-ylmethyl)piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound S1C(=NC2=C1C=CC=C2)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O BCUAHBPXSNSQRT-UHFFFAOYSA-N 0.000 claims 1
- KVNJEGUBZLNFRH-UHFFFAOYSA-N 3-[6-[1-(1,3-benzothiazol-5-ylmethyl)piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound S1C=NC2=C1C=CC(=C2)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O KVNJEGUBZLNFRH-UHFFFAOYSA-N 0.000 claims 1
- PNUQKYOGBXTYJT-UHFFFAOYSA-N 3-[6-[1-(1,3-dihydro-2-benzofuran-5-ylmethyl)piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C1OCC2=CC(=CC=C12)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O PNUQKYOGBXTYJT-UHFFFAOYSA-N 0.000 claims 1
- UBOLQHVGWIAGKL-UHFFFAOYSA-N 3-[6-[1-(1,3-oxazol-2-ylmethyl)piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O1C(=NC=C1)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O UBOLQHVGWIAGKL-UHFFFAOYSA-N 0.000 claims 1
- ZULRSNBMKGJUQT-UHFFFAOYSA-N 3-[6-[1-(1H-benzimidazol-2-ylmethyl)piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound N1C(=NC2=C1C=CC=C2)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O ZULRSNBMKGJUQT-UHFFFAOYSA-N 0.000 claims 1
- GWQWPUJOLHVPME-UHFFFAOYSA-N 3-[6-[1-(1H-imidazol-5-ylmethyl)piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound N1C=NC=C1CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O GWQWPUJOLHVPME-UHFFFAOYSA-N 0.000 claims 1
- ANLFIKBFICRKTH-UHFFFAOYSA-N 3-[6-[1-(1H-indazol-4-ylmethyl)piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound N1N=CC2=C(C=CC=C12)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O ANLFIKBFICRKTH-UHFFFAOYSA-N 0.000 claims 1
- JAEGXTSONZTMSX-UHFFFAOYSA-N 3-[6-[1-(1H-indazol-5-ylmethyl)piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound N1N=CC2=CC(=CC=C12)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O JAEGXTSONZTMSX-UHFFFAOYSA-N 0.000 claims 1
- TXFXBHKVLDLABM-UHFFFAOYSA-N 3-[6-[1-(1H-indazol-6-ylmethyl)piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound N1N=CC2=CC=C(C=C12)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O TXFXBHKVLDLABM-UHFFFAOYSA-N 0.000 claims 1
- DUWFQGAIZPHXJE-UHFFFAOYSA-N 3-[6-[1-(2,1,3-benzoxadiazol-5-ylmethyl)piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound N=1ON=C2C=1C=CC(=C2)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O DUWFQGAIZPHXJE-UHFFFAOYSA-N 0.000 claims 1
- FDTKKYMXWLXWHH-UHFFFAOYSA-N 3-[6-[1-(2,2-difluoro-1-phenylethyl)piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound FC(C(C1=CC=CC=C1)N1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)F FDTKKYMXWLXWHH-UHFFFAOYSA-N 0.000 claims 1
- IWRAEVCQUNPGEK-UHFFFAOYSA-N 3-[6-[1-(2,2-difluoroethyl)piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound FC(CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)F IWRAEVCQUNPGEK-UHFFFAOYSA-N 0.000 claims 1
- CFTARRAQUCFVGO-UHFFFAOYSA-N 3-[6-[1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O1C2=C(OCC1)C=C(C=C2)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O CFTARRAQUCFVGO-UHFFFAOYSA-N 0.000 claims 1
- TVOYQWMFEIBMBX-UHFFFAOYSA-N 3-[6-[1-(2-fluoro-1-phenylethyl)piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound FCC(C1=CC=CC=C1)N1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O TVOYQWMFEIBMBX-UHFFFAOYSA-N 0.000 claims 1
- JXYJEPOJLPUJQS-UHFFFAOYSA-N 3-[6-[1-(2-hydroxy-1-phenylethyl)piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound OCC(C1=CC=CC=C1)N1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O JXYJEPOJLPUJQS-UHFFFAOYSA-N 0.000 claims 1
- ZMXUIWWEUXUPDY-UHFFFAOYSA-N 3-[6-[1-(2-methylpropyl)piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C(C)C)N1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O ZMXUIWWEUXUPDY-UHFFFAOYSA-N 0.000 claims 1
- CNFNRBXTXHAUHB-UHFFFAOYSA-N 3-[6-[1-(3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O1C2=C(OCCC1)C=C(C=C2)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O CNFNRBXTXHAUHB-UHFFFAOYSA-N 0.000 claims 1
- DLNCKBAFAMSJBL-UHFFFAOYSA-N 3-[6-[1-(3-fluoropropyl)piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound FCCCN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O DLNCKBAFAMSJBL-UHFFFAOYSA-N 0.000 claims 1
- OOVKHIMHVHSBSN-UHFFFAOYSA-N 3-[6-[1-(3-morpholin-4-ylpropyl)piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O1CCN(CC1)CCCN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O OOVKHIMHVHSBSN-UHFFFAOYSA-N 0.000 claims 1
- MUTHEGCRWZDDNX-UHFFFAOYSA-N 3-[6-[1-(4-tert-butylbenzoyl)piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C)(C)(C)C1=CC=C(C(=O)N2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C1 MUTHEGCRWZDDNX-UHFFFAOYSA-N 0.000 claims 1
- DUXYSGNDNWPFNY-UHFFFAOYSA-N 3-[6-[1-(benzenesulfonyl)piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)S(=O)(=O)C1=CC=CC=C1)C1C(NC(CC1)=O)=O DUXYSGNDNWPFNY-UHFFFAOYSA-N 0.000 claims 1
- PGEQODYZTXICEF-UHFFFAOYSA-N 3-[6-[1-(cyclobutylmethyl)piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C1(CCC1)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O PGEQODYZTXICEF-UHFFFAOYSA-N 0.000 claims 1
- HEJDXESUUWJNDH-UHFFFAOYSA-N 3-[6-[1-(cyclohexylmethyl)piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C1(CCCCC1)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O HEJDXESUUWJNDH-UHFFFAOYSA-N 0.000 claims 1
- OILOJUCCPUSETC-UHFFFAOYSA-N 3-[6-[1-(cyclopentylmethyl)piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C1(CCCC1)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O OILOJUCCPUSETC-UHFFFAOYSA-N 0.000 claims 1
- FOHUGSWYSRNXAV-UHFFFAOYSA-N 3-[6-[1-(cyclopropylmethyl)piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C1(CC1)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O FOHUGSWYSRNXAV-UHFFFAOYSA-N 0.000 claims 1
- ODLQPJYTLWOUOQ-UHFFFAOYSA-N 3-[6-[1-(isoquinolin-1-ylmethyl)piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C1(=NC=CC2=CC=CC=C12)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O ODLQPJYTLWOUOQ-UHFFFAOYSA-N 0.000 claims 1
- JZKKAUQSCWWMPV-UHFFFAOYSA-N 3-[6-[1-(naphthalen-1-ylmethyl)piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C1(=CC=CC2=CC=CC=C12)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O JZKKAUQSCWWMPV-UHFFFAOYSA-N 0.000 claims 1
- PXEMKHYUEBWHLD-UHFFFAOYSA-N 3-[6-[1-(naphthalen-2-ylmethyl)piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C1=C(C=CC2=CC=CC=C12)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O PXEMKHYUEBWHLD-UHFFFAOYSA-N 0.000 claims 1
- UQAZOEVWXTWRGH-UHFFFAOYSA-N 3-[6-[1-(oxan-4-ylmethyl)piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC1CCOCC1)C1C(NC(CC1)=O)=O UQAZOEVWXTWRGH-UHFFFAOYSA-N 0.000 claims 1
- JDOLQEBNMDCXMI-UHFFFAOYSA-N 3-[6-[1-[(1,4-dimethylimidazol-2-yl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound CN1C(=NC(=C1)C)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O JDOLQEBNMDCXMI-UHFFFAOYSA-N 0.000 claims 1
- FTIJOWVSUPDQCE-UHFFFAOYSA-N 3-[6-[1-[(1-benzyltetrazol-5-yl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C1=CC=CC=C1)N1N=NN=C1CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O FTIJOWVSUPDQCE-UHFFFAOYSA-N 0.000 claims 1
- XJNINVLKRMVWLF-UHFFFAOYSA-N 3-[6-[1-[(1-cyclobutyltriazol-4-yl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C1(CCC1)N1N=NC(=C1)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O XJNINVLKRMVWLF-UHFFFAOYSA-N 0.000 claims 1
- WECJTPMEBKRYEW-UHFFFAOYSA-N 3-[6-[1-[(1-ethyl-3-pyridin-3-ylpyrazol-4-yl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C)N1N=C(C(=C1)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)C=1C=NC=CC=1 WECJTPMEBKRYEW-UHFFFAOYSA-N 0.000 claims 1
- QIOXFJSSQRJVBQ-UHFFFAOYSA-N 3-[6-[1-[(1-ethylpyrazol-3-yl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C)N1N=C(C=C1)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O QIOXFJSSQRJVBQ-UHFFFAOYSA-N 0.000 claims 1
- YWZOEHDNJOBUKK-UHFFFAOYSA-N 3-[6-[1-[(1-methylbenzimidazol-2-yl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound CN1C(=NC2=C1C=CC=C2)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O YWZOEHDNJOBUKK-UHFFFAOYSA-N 0.000 claims 1
- ZSPNPLGAFDSMMT-UHFFFAOYSA-N 3-[6-[1-[(1-methylindazol-3-yl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound CN1N=C(C2=CC=CC=C12)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O ZSPNPLGAFDSMMT-UHFFFAOYSA-N 0.000 claims 1
- QDISJEOFPDXMGD-UHFFFAOYSA-N 3-[6-[1-[(1-methylpyrazol-3-yl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound CN1N=C(C=C1)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O QDISJEOFPDXMGD-UHFFFAOYSA-N 0.000 claims 1
- XFDPVXAEZLNHRO-UHFFFAOYSA-N 3-[6-[1-[(1-methylpyrazol-4-yl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound CN1N=CC(=C1)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O XFDPVXAEZLNHRO-UHFFFAOYSA-N 0.000 claims 1
- JXYJEPOJLPUJQS-WCSIJFPASA-N 3-[6-[1-[(1R)-2-hydroxy-1-phenylethyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound OC[C@@H](C1=CC=CC=C1)N1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O JXYJEPOJLPUJQS-WCSIJFPASA-N 0.000 claims 1
- JXYJEPOJLPUJQS-OZAIVSQSSA-N 3-[6-[1-[(1S)-2-hydroxy-1-phenylethyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound OC[C@H](C1=CC=CC=C1)N1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O JXYJEPOJLPUJQS-OZAIVSQSSA-N 0.000 claims 1
- MGYWBBXOQGTODZ-UHFFFAOYSA-N 3-[6-[1-[(2,2-difluoro-1,3-benzodioxol-5-yl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound FC1(OC2=C(O1)C=CC(=C2)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)F MGYWBBXOQGTODZ-UHFFFAOYSA-N 0.000 claims 1
- BJUPNFUJKDLASD-UHFFFAOYSA-N 3-[6-[1-[(2,3-difluorophenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound FC1=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=CC=C1F BJUPNFUJKDLASD-UHFFFAOYSA-N 0.000 claims 1
- IXUJFBSXUSAZAT-UHFFFAOYSA-N 3-[6-[1-[(2,4-dichlorophenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound ClC1=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=CC(=C1)Cl IXUJFBSXUSAZAT-UHFFFAOYSA-N 0.000 claims 1
- FRKANCGVDNWOMV-UHFFFAOYSA-N 3-[6-[1-[(2,4-difluorophenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound FC1=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=CC(=C1)F FRKANCGVDNWOMV-UHFFFAOYSA-N 0.000 claims 1
- XGZGRIRJHDMBEN-UHFFFAOYSA-N 3-[6-[1-[(2,4-dimethylphenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound CC1=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=CC(=C1)C XGZGRIRJHDMBEN-UHFFFAOYSA-N 0.000 claims 1
- USDNOGFENOULGA-UHFFFAOYSA-N 3-[6-[1-[(2,5-dichlorophenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound ClC1=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C(C=C1)Cl USDNOGFENOULGA-UHFFFAOYSA-N 0.000 claims 1
- DQLIILBANRDESY-UHFFFAOYSA-N 3-[6-[1-[(2,5-difluorophenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound FC1=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C(C=C1)F DQLIILBANRDESY-UHFFFAOYSA-N 0.000 claims 1
- LRWNPDRUYZYVLJ-UHFFFAOYSA-N 3-[6-[1-[(2,5-dimethylphenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound CC1=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C(C=C1)C LRWNPDRUYZYVLJ-UHFFFAOYSA-N 0.000 claims 1
- LJLKCNRTOQMULJ-UHFFFAOYSA-N 3-[6-[1-[(2,5-dimethylpyrazol-3-yl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound CN1N=C(C=C1CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)C LJLKCNRTOQMULJ-UHFFFAOYSA-N 0.000 claims 1
- OANORGLALAJCFO-UHFFFAOYSA-N 3-[6-[1-[(2,6-dichlorophenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound ClC1=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C(=CC=C1)Cl OANORGLALAJCFO-UHFFFAOYSA-N 0.000 claims 1
- IIJBLJJNSHCUCI-UHFFFAOYSA-N 3-[6-[1-[(2,6-difluorophenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound FC1=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C(=CC=C1)F IIJBLJJNSHCUCI-UHFFFAOYSA-N 0.000 claims 1
- QWEXVPAPFAGLGG-UHFFFAOYSA-N 3-[6-[1-[(2,6-dimethylphenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound CC1=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C(=CC=C1)C QWEXVPAPFAGLGG-UHFFFAOYSA-N 0.000 claims 1
- HHAIVXVPZPJIKQ-UHFFFAOYSA-N 3-[6-[1-[(2-aminopyrimidin-5-yl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound NC1=NC=C(C=N1)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O HHAIVXVPZPJIKQ-UHFFFAOYSA-N 0.000 claims 1
- CLOZHNBGAHAVOZ-UHFFFAOYSA-N 3-[6-[1-[(2-chloro-1,3-thiazol-5-yl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound ClC=1SC(=CN=1)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O CLOZHNBGAHAVOZ-UHFFFAOYSA-N 0.000 claims 1
- NNLBRFNZBWHJOZ-UHFFFAOYSA-N 3-[6-[1-[(2-chloro-4-fluorophenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound ClC1=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=CC(=C1)F NNLBRFNZBWHJOZ-UHFFFAOYSA-N 0.000 claims 1
- AMCXFEHISBTPPD-UHFFFAOYSA-N 3-[6-[1-[(2-chlorophenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound ClC1=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=CC=C1 AMCXFEHISBTPPD-UHFFFAOYSA-N 0.000 claims 1
- JVWONFNFYQMTMA-UHFFFAOYSA-N 3-[6-[1-[(2-cyclopropylphenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C1(CC1)C1=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=CC=C1 JVWONFNFYQMTMA-UHFFFAOYSA-N 0.000 claims 1
- CSZIDYZKCSSUNK-UHFFFAOYSA-N 3-[6-[1-[(2-fluorophenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound FC1=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=CC=C1 CSZIDYZKCSSUNK-UHFFFAOYSA-N 0.000 claims 1
- MTUXUBGKJPRZCC-UHFFFAOYSA-N 3-[6-[1-[(2-methoxyphenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound COC1=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=CC=C1 MTUXUBGKJPRZCC-UHFFFAOYSA-N 0.000 claims 1
- SHSPYPHACMWHEU-UHFFFAOYSA-N 3-[6-[1-[(2-methylphenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound CC1=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=CC=C1 SHSPYPHACMWHEU-UHFFFAOYSA-N 0.000 claims 1
- YNQVBWSKSTYTLX-UHFFFAOYSA-N 3-[6-[1-[(2-morpholin-4-ylpyrimidin-5-yl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O1CCN(CC1)C1=NC=C(C=N1)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O YNQVBWSKSTYTLX-UHFFFAOYSA-N 0.000 claims 1
- IEHXPBDDBXFKDH-UHFFFAOYSA-N 3-[6-[1-[(2-tert-butyl-1,3-thiazol-4-yl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C)(C)(C)C=1SC=C(N=1)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O IEHXPBDDBXFKDH-UHFFFAOYSA-N 0.000 claims 1
- IBJJXZXVJBAQKR-UHFFFAOYSA-N 3-[6-[1-[(3,4-dichlorophenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound ClC=1C=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=CC=1Cl IBJJXZXVJBAQKR-UHFFFAOYSA-N 0.000 claims 1
- CHLOUIIIMKZLJL-UHFFFAOYSA-N 3-[6-[1-[(3,4-difluorophenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound FC=1C=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=CC=1F CHLOUIIIMKZLJL-UHFFFAOYSA-N 0.000 claims 1
- WPTAEIYBPHXHRJ-UHFFFAOYSA-N 3-[6-[1-[(3,4-dimethylphenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound CC=1C=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=CC=1C WPTAEIYBPHXHRJ-UHFFFAOYSA-N 0.000 claims 1
- MSMSFFBEOQHAHG-UHFFFAOYSA-N 3-[6-[1-[(3,5-dibromophenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound BrC=1C=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C(C=1)Br MSMSFFBEOQHAHG-UHFFFAOYSA-N 0.000 claims 1
- IOJSJTBXXZHPBV-UHFFFAOYSA-N 3-[6-[1-[(3,5-difluoro-4-hydroxyphenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound FC=1C=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C(C=1O)F IOJSJTBXXZHPBV-UHFFFAOYSA-N 0.000 claims 1
- UFOOEGKFLBPCDV-UHFFFAOYSA-N 3-[6-[1-[(3,5-difluorophenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound FC=1C=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C(C=1)F UFOOEGKFLBPCDV-UHFFFAOYSA-N 0.000 claims 1
- QCZOZNGYXAHBMF-UHFFFAOYSA-N 3-[6-[1-[(3,5-dimethyl-1,2-oxazol-4-yl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound CC1=NOC(=C1CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)C QCZOZNGYXAHBMF-UHFFFAOYSA-N 0.000 claims 1
- YLORBUGGSSVLDG-UHFFFAOYSA-N 3-[6-[1-[(3,5-dimethylphenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound CC=1C=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C(C=1)C YLORBUGGSSVLDG-UHFFFAOYSA-N 0.000 claims 1
- GJHRTKZYZOEBLR-UHFFFAOYSA-N 3-[6-[1-[(3-chloro-4-fluorophenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound ClC=1C=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=CC=1F GJHRTKZYZOEBLR-UHFFFAOYSA-N 0.000 claims 1
- HEAFENIZHQDSFU-UHFFFAOYSA-N 3-[6-[1-[(3-chloro-5-fluorophenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound ClC=1C=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C(C=1)F HEAFENIZHQDSFU-UHFFFAOYSA-N 0.000 claims 1
- XFELGEMMBRJKSO-UHFFFAOYSA-N 3-[6-[1-[(3-chlorophenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound ClC=1C=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=CC=1 XFELGEMMBRJKSO-UHFFFAOYSA-N 0.000 claims 1
- SMLLWPJNCZTVJW-UHFFFAOYSA-N 3-[6-[1-[(3-cyclopropyl-1H-pyrazol-5-yl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C1(CC1)C1=CC(=NN1)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O SMLLWPJNCZTVJW-UHFFFAOYSA-N 0.000 claims 1
- CJPKXBYZZDBIIC-UHFFFAOYSA-N 3-[6-[1-[(3-fluoro-1-bicyclo[1.1.1]pentanyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound FC12CC(C1)(C2)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O CJPKXBYZZDBIIC-UHFFFAOYSA-N 0.000 claims 1
- CBYUCXMJCAPTDE-UHFFFAOYSA-N 3-[6-[1-[(3-fluoro-4-methylphenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound FC=1C=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=CC=1C CBYUCXMJCAPTDE-UHFFFAOYSA-N 0.000 claims 1
- LNQRMJARZIDTFJ-UHFFFAOYSA-N 3-[6-[1-[(3-fluorophenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound FC=1C=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=CC=1 LNQRMJARZIDTFJ-UHFFFAOYSA-N 0.000 claims 1
- SHJGMYPVRGFCLV-UHFFFAOYSA-N 3-[6-[1-[(3-methoxyphenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound COC=1C=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=CC=1 SHJGMYPVRGFCLV-UHFFFAOYSA-N 0.000 claims 1
- YTXUWRWNBJRVBT-UHFFFAOYSA-N 3-[6-[1-[(3-methyl-1,2-oxazol-5-yl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound CC1=NOC(=C1)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O YTXUWRWNBJRVBT-UHFFFAOYSA-N 0.000 claims 1
- UNWOJKNPVOVVDS-UHFFFAOYSA-N 3-[6-[1-[(3-methylphenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound CC=1C=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=CC=1 UNWOJKNPVOVVDS-UHFFFAOYSA-N 0.000 claims 1
- RCDKQQKUOIBEJT-UHFFFAOYSA-N 3-[6-[1-[(3-morpholin-4-ylsulfonylphenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O1CCN(CC1)S(=O)(=O)C=1C=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=CC=1 RCDKQQKUOIBEJT-UHFFFAOYSA-N 0.000 claims 1
- WFGVYUKFIOFKGR-UHFFFAOYSA-N 3-[6-[1-[(4-bromophenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound BrC1=CC=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C1 WFGVYUKFIOFKGR-UHFFFAOYSA-N 0.000 claims 1
- GMIAJYGPSBAGBJ-UHFFFAOYSA-N 3-[6-[1-[(4-chloro-2-fluorophenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound ClC1=CC(=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C1)F GMIAJYGPSBAGBJ-UHFFFAOYSA-N 0.000 claims 1
- OAEGQXDQOFBHKS-UHFFFAOYSA-N 3-[6-[1-[(4-chloro-3-fluorophenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione 3-[6-[1-[(3,5-dichlorophenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound Fc1cc(CN2CCC(CC2)c2ccc3C(=O)N(Cc3c2)C2CCC(=O)NC2=O)ccc1Cl.Clc1cc(Cl)cc(CN2CCC(CC2)c2ccc3C(=O)N(Cc3c2)C2CCC(=O)NC2=O)c1 OAEGQXDQOFBHKS-UHFFFAOYSA-N 0.000 claims 1
- IGYOTWUTTRVOGO-UHFFFAOYSA-N 3-[6-[1-[(4-chlorophenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound ClC1=CC=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C1 IGYOTWUTTRVOGO-UHFFFAOYSA-N 0.000 claims 1
- VHHJTCKTVKOSEW-UHFFFAOYSA-N 3-[6-[1-[(4-cyclobutylphenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C1(CCC1)C1=CC=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C1 VHHJTCKTVKOSEW-UHFFFAOYSA-N 0.000 claims 1
- WLEWJQVSJDSUFL-UHFFFAOYSA-N 3-[6-[1-[(4-cyclohexylphenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C1(CCCCC1)C1=CC=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C1 WLEWJQVSJDSUFL-UHFFFAOYSA-N 0.000 claims 1
- KGYMDPOUIINEAB-UHFFFAOYSA-N 3-[6-[1-[(4-cyclopentylphenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C1(CCCC1)C1=CC=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C1 KGYMDPOUIINEAB-UHFFFAOYSA-N 0.000 claims 1
- SKKBBAXBRCLCIH-UHFFFAOYSA-N 3-[6-[1-[(4-ethoxyphenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C)OC1=CC=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C1 SKKBBAXBRCLCIH-UHFFFAOYSA-N 0.000 claims 1
- LFPMAOGCDRTEIU-UHFFFAOYSA-N 3-[6-[1-[(4-ethylphenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C)C1=CC=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C1 LFPMAOGCDRTEIU-UHFFFAOYSA-N 0.000 claims 1
- YFDRFOOVHSFPHI-UHFFFAOYSA-N 3-[6-[1-[(4-fluorophenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound FC1=CC=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C1 YFDRFOOVHSFPHI-UHFFFAOYSA-N 0.000 claims 1
- UXUAWKNKUURTRC-UHFFFAOYSA-N 3-[6-[1-[(4-imidazol-1-ylphenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound N1(C=NC=C1)C1=CC=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C1 UXUAWKNKUURTRC-UHFFFAOYSA-N 0.000 claims 1
- KCODGVOMFPCEMB-UHFFFAOYSA-N 3-[6-[1-[(4-methoxyphenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound COC1=CC=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C1 KCODGVOMFPCEMB-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
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Families Citing this family (68)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20180228907A1 (en) | 2014-04-14 | 2018-08-16 | Arvinas, Inc. | Cereblon ligands and bifunctional compounds comprising the same |
| EP3454856B1 (en) | 2016-05-10 | 2024-09-11 | C4 Therapeutics, Inc. | Heterocyclic degronimers for target protein degradation |
| TWI793151B (zh) | 2017-08-23 | 2023-02-21 | 瑞士商諾華公司 | 3-(1-氧異吲哚啉-2-基)之氫吡啶-2,6-二酮衍生物及其用途 |
| WO2019199816A1 (en) * | 2018-04-13 | 2019-10-17 | Arvinas Operations, Inc. | Cereblon ligands and bifunctional compounds comprising the same |
| AR116109A1 (es) * | 2018-07-10 | 2021-03-31 | Novartis Ag | Derivados de 3-(5-amino-1-oxoisoindolin-2-il)piperidina-2,6-diona y usos de los mismos |
| EP3820573B1 (en) * | 2018-07-10 | 2023-08-09 | Novartis AG | 3-(5-hydroxy-1-oxoisoindolin-2-yl)piperidine-2,6-dione derivatives and their use in the treatment of ikaros family zinc finger 2 (ikzf2)-dependent diseases |
| WO2020117759A1 (en) | 2018-12-03 | 2020-06-11 | Dana-Farber Cancer Institute, Inc. | Small molecule degraders of helios and methods of use |
| US20240245670A1 (en) * | 2018-12-20 | 2024-07-25 | Novartis Ag | Dosing regimen and pharmaceutical combination comprising 3-(1-oxoisoindolin-2-yl)piperidine-2,6-dione derivatives |
| EP3924055B1 (en) * | 2019-02-15 | 2024-04-03 | Novartis AG | Substituted 3-(1-oxoisoindolin-2-yl)piperidine-2,6-dione derivatives and uses thereof |
| EP3924054B1 (en) * | 2019-02-15 | 2025-04-02 | Novartis AG | 3-(1-oxo-5-(piperidin-4-yl)isoindolin-2-yl)piperidine-2,6-dione derivatives and uses thereof |
| EA202192738A1 (ru) | 2019-04-12 | 2022-03-17 | С4 Терапьютикс, Инк. | Трициклические соединения, обеспечивающие разрушение белка ikaros и белка aiolos |
| US20220251152A1 (en) | 2019-04-24 | 2022-08-11 | Novartis Ag | Compositions and methods for selective protein degradation |
| MX2021014443A (es) | 2019-05-31 | 2022-01-06 | Ikena Oncology Inc | Inhibidores del dominio asociado mejorador de la transcripcion (tead) y usos de los mismos. |
| AU2020282759A1 (en) | 2019-05-31 | 2021-12-23 | Ikena Oncology, Inc. | TEAD inhibitors and uses thereof |
| AU2020374957A1 (en) * | 2019-10-30 | 2022-04-28 | Dana-Farber Cancer Institute, Inc. | Small molecule degraders of Helios and methods of use |
| CN110862395B (zh) * | 2019-11-13 | 2020-09-29 | 株洲千金药业股份有限公司 | 一种制备他达拉非重要杂质的原料化合物的制备方法 |
| KR20220103753A (ko) * | 2019-11-19 | 2022-07-22 | 브리스톨-마이어스 스큅 컴퍼니 | 헬리오스 단백질의 억제제로서 유용한 화합물 |
| TW202140441A (zh) * | 2020-03-23 | 2021-11-01 | 美商必治妥美雅史谷比公司 | 經取代之側氧基異吲哚啉化合物 |
| US20230203022A1 (en) * | 2020-04-30 | 2023-06-29 | Shanghaitech University | Heterocycle and glutarimide skeleton-based compound and applications thereof |
| CA3182346A1 (en) | 2020-06-23 | 2021-12-30 | Novartis Ag | Dosing regimen comprising 3-(1-oxoisoindolin-2-yl)piperidine-2,6-dione derivatives |
| WO2022007903A1 (zh) * | 2020-07-09 | 2022-01-13 | 四川海思科制药有限公司 | 一种能够抑制并降解雄激素受体的化合物及其药物组合物和药学上的应用 |
| AU2021319847A1 (en) * | 2020-08-03 | 2023-03-02 | Captor Therapeutics S.A. | Low molecular weight protein degraders and their applications |
| CN116134027B (zh) * | 2020-08-03 | 2025-01-24 | 诺华股份有限公司 | 杂芳基取代的3-(1-氧代异吲哚啉-2-基)哌啶-2,6-二酮衍生物及其用途 |
| EP4217352A4 (en) | 2020-09-23 | 2024-04-10 | St. Jude Children's Research Hospital, Inc. | Substituted n-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)arylsulfonamide analogs as modulators of cereblon protein |
| EP4225749A4 (en) * | 2020-10-07 | 2025-05-14 | Cullgen (Shanghai), Inc. | Compounds and methods of treating cancers |
| MX2023004374A (es) * | 2020-10-14 | 2023-07-06 | C4 Therapeutics Inc | Ligandos tricíclicos para la degradación de la familia ikaros 2 o la familia ikaros 4. |
| CN116669769A (zh) * | 2020-10-16 | 2023-08-29 | 达纳-法伯癌症研究所公司 | Helios的哌啶基小分子降解剂和使用方法 |
| WO2022081976A1 (en) * | 2020-10-16 | 2022-04-21 | Dana-Farber Cancer Institute, Inc. | Piperidinyl small molecule degraders of helios and methods of use |
| WO2022120355A1 (en) * | 2020-12-02 | 2022-06-09 | Ikena Oncology, Inc. | Tead degraders and uses thereof |
| UY39671A (es) * | 2021-03-15 | 2022-10-31 | Novartis Ag | Derivados de pirazolopiridina y sus usos. |
| AU2022253242A1 (en) | 2021-04-06 | 2023-11-23 | Bristol-Myers Squibb Company | Pyridinyl substituted oxoisoindoline compounds |
| JP2024517772A (ja) * | 2021-04-29 | 2024-04-23 | ネオモルフ インコーポレイテッド | 置換された2-(2,6-ジオキソピペリジン-3-イル)-5-(1-ピペリジン-4-イル)イソインドリン-1,3-ジオン誘導体及びその使用 |
| CA3209633A1 (en) * | 2021-04-29 | 2022-11-03 | Tinghu Zhang | Phthalimido cereblon complex binders and transcription factor degraders and methods of use |
| KR20240035820A (ko) | 2021-07-09 | 2024-03-18 | 플렉시움 인코포레이티드 | Ikzf2를 조절하는 아릴 화합물 및 약학 조성물 |
| AR126718A1 (es) | 2021-08-06 | 2023-11-08 | Celgene Corp | Composiciones y métodos para la degradación selectiva de proteínas diseñadas por ingeniería |
| CN118475567A (zh) * | 2021-08-11 | 2024-08-09 | 西藏海思科制药有限公司 | 一种杂环衍生物及其组合物和药学上的应用 |
| CN116003418A (zh) * | 2021-10-22 | 2023-04-25 | 标新生物医药科技(上海)有限公司 | Crbn e3连接酶配体化合物、基于该配体化合物开发的蛋白降解剂及它们的应用 |
| KR20240091056A (ko) | 2021-10-28 | 2024-06-21 | 길리애드 사이언시즈, 인코포레이티드 | 피리디진-3(2h)-온 유도체 |
| WO2023077030A1 (en) | 2021-10-29 | 2023-05-04 | Gilead Sciences, Inc. | Cd73 compounds |
| EP4452414A2 (en) | 2021-12-22 | 2024-10-30 | Gilead Sciences, Inc. | Ikaros zinc finger family degraders and uses thereof |
| JP2024545193A (ja) * | 2021-12-22 | 2024-12-05 | ギリアード サイエンシーズ, インコーポレイテッド | Ikarosジンクフィンガーファミリー分解剤及びその使用 |
| TW202340168A (zh) | 2022-01-28 | 2023-10-16 | 美商基利科學股份有限公司 | Parp7抑制劑 |
| CN116640122A (zh) * | 2022-02-16 | 2023-08-25 | 苏州国匡医药科技有限公司 | Ikzf2降解剂及包含其的药物组合物和用途 |
| US12358887B2 (en) | 2022-03-17 | 2025-07-15 | Gilead Sciences, Inc. | IKAROS Zinc Finger Family degraders and uses thereof |
| US20250215012A1 (en) * | 2022-03-25 | 2025-07-03 | Regents Of The University Of Michigan | Ikzf2 degraders and uses thereof |
| CN119585252A (zh) * | 2022-03-25 | 2025-03-07 | 翁科皮亚治疗公司和Sk生命科学实验室 | 作为ikzf2降解剂的含二环杂芳基的化合物 |
| WO2023201012A1 (en) * | 2022-04-15 | 2023-10-19 | Regents Of The University Of Michigan | Ikzf2 degraders and uses thereof |
| CN119487038A (zh) | 2022-04-21 | 2025-02-18 | 吉利德科学公司 | Kras g12d调节化合物 |
| WO2024006929A1 (en) | 2022-07-01 | 2024-01-04 | Gilead Sciences, Inc. | Cd73 compounds |
| CN117881668A (zh) * | 2022-08-10 | 2024-04-12 | 标新生物医药科技(上海)有限公司 | 基于异吲哚啉取代戊二酰亚胺骨架的化合物及其应用 |
| WO2024059107A1 (en) * | 2022-09-14 | 2024-03-21 | President And Fellows Of Harvard College | Ikzf2 and ck1-alpha degrading compounds and uses thereof |
| JP2025541840A (ja) * | 2022-12-07 | 2025-12-23 | ハンジョウ グルバイオ ファーマシューティカル カンパニー リミテッド | 固体分散体、その製造方法と使用 |
| EP4638436A1 (en) | 2022-12-22 | 2025-10-29 | Gilead Sciences, Inc. | Prmt5 inhibitors and uses thereof |
| EP4660193A1 (en) | 2023-01-31 | 2025-12-10 | Korea Research Institute of Chemical Technology | Indole compound decomposing ikzf2, and use thereof |
| WO2024215754A1 (en) | 2023-04-11 | 2024-10-17 | Gilead Sciences, Inc. | Kras modulating compounds |
| CN121079300A (zh) | 2023-04-21 | 2025-12-05 | 吉利德科学公司 | Prmt5抑制剂及其用途 |
| US20250042922A1 (en) | 2023-06-30 | 2025-02-06 | Gilead Sciences, Inc. | Kras modulating compounds |
| US20250066328A1 (en) | 2023-07-26 | 2025-02-27 | Gilead Sciences, Inc. | Parp7 inhibitors |
| WO2025024811A1 (en) | 2023-07-26 | 2025-01-30 | Gilead Sciences, Inc. | Parp7 inhibitors |
| WO2025054530A1 (en) | 2023-09-08 | 2025-03-13 | Gilead Sciences, Inc. | Pyrimidine-containing polycyclic derivatives as kras g12d modulating compounds |
| WO2025054347A1 (en) | 2023-09-08 | 2025-03-13 | Gilead Sciences, Inc. | Kras g12d modulating compounds |
| WO2025067466A1 (zh) * | 2023-09-28 | 2025-04-03 | 杭州多域生物技术有限公司 | 一种杂环化合物、其组合物及应用 |
| TW202530195A (zh) * | 2023-10-06 | 2025-08-01 | 美商德爾菲亞治療股份有限公司 | 化合物、其醫藥組合物及其使用方法 |
| US20250154172A1 (en) | 2023-11-03 | 2025-05-15 | Gilead Sciences, Inc. | Prmt5 inhibitors and uses thereof |
| WO2025113643A1 (en) | 2023-12-01 | 2025-06-05 | Gilead Sciences Inc. | Anti-fap-light fusion protein and use thereof |
| US20250230168A1 (en) | 2023-12-22 | 2025-07-17 | Gilead Sciences, Inc. | Azaspiro wrn inhibitors |
| WO2025245003A1 (en) | 2024-05-21 | 2025-11-27 | Gilead Sciences, Inc. | Prmt5 inhibitors and uses thereof |
| WO2025245178A1 (en) * | 2024-05-21 | 2025-11-27 | Innovo Therapeutics, Inc. | Pak4, cstf2, or cstf2t protein degraders, pharmaceutical compositions, and therapeutic applications |
Family Cites Families (92)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5114946A (en) | 1987-06-12 | 1992-05-19 | American Cyanamid Company | Transdermal delivery of pharmaceuticals |
| US4818541A (en) | 1987-08-19 | 1989-04-04 | Schering Corporation | Transdermal delivery of enantiomers of phenylpropanolamine |
| US7196170B2 (en) | 1992-09-14 | 2007-03-27 | The General Hospital Corporation | Aiolos, Helios, Daedalos and Ikaros: genes, polypeptides, regulatory elements and uses thereof |
| US5262564A (en) | 1992-10-30 | 1993-11-16 | Octamer, Inc. | Sulfinic acid adducts of organo nitroso compounds useful as retroviral inactivating agents anti-retroviral agents and anti-tumor agents |
| CZ302378B6 (cs) | 1996-07-24 | 2011-04-20 | Celgene Corporation | Optický izomer (S)-1,3-dioxo-2-(2,6-dioxopiperidin-3-yl)-4-aminoisoindolin a farmaceutická kompozice s jeho obsahem |
| WO2002044372A2 (en) | 2000-12-01 | 2002-06-06 | Parker Hughes Institute | Nucleotide and protein sequence of helios 3 and methods of use |
| EP1396493A4 (en) | 2001-04-26 | 2005-08-03 | Ajinomoto Kk | HETEROCYCLIC COMPOUNDS |
| CA2457319C (en) | 2001-08-06 | 2011-07-05 | The Children's Medical Center Corporation | Synthesis and anti-tumor activity of nitrogen substituted thalidomide analogs |
| US20050203142A1 (en) | 2002-10-24 | 2005-09-15 | Zeldis Jerome B. | Methods of using and compositions comprising immunomodulatory compounds for treatment, modification and management of pain |
| US20040087558A1 (en) | 2002-10-24 | 2004-05-06 | Zeldis Jerome B. | Methods of using and compositions comprising selective cytokine inhibitory drugs for treatment, modification and management of pain |
| US7612096B2 (en) | 2003-10-23 | 2009-11-03 | Celgene Corporation | Methods for treatment, modification and management of radiculopathy using 1-oxo-2-(2,6-dioxopiperidin-3yl)-4-aminoisoindoline |
| US20070161696A1 (en) | 2004-04-23 | 2007-07-12 | Zeldis Jerome B | Methods of using and compositions comprising selective cytokine inhibitory drugs for treatment, modification and management of pain |
| KR20070057907A (ko) * | 2004-09-03 | 2007-06-07 | 셀진 코포레이션 | 치환된 2-(2,6-디옥소피페리딘-3-일)-1-옥소이소인돌린의제조 방법 |
| JP4731867B2 (ja) | 2004-10-01 | 2011-07-27 | 国立大学法人三重大学 | Cd8陽性の細胞傷害性tリンパ球の誘導方法 |
| WO2006060507A2 (en) | 2004-12-01 | 2006-06-08 | Celgene Corporation | Compositions comprising immunomodulatory compounds and the use thereof for the treatment of immunodeficiency disorders |
| ATE481504T1 (de) | 2004-12-10 | 2010-10-15 | Siemens Healthcare Diagnostics | Für die vorhersage des ansprechens maligner neoplasie auf eine auf taxan beruhende medizinische behandlung geeignete genetische veränderung |
| WO2007067500A2 (en) | 2005-12-05 | 2007-06-14 | Genomic Health, Inc. | Predictors of patient response to treatment with egfr inhibitors |
| US9598669B2 (en) | 2005-12-29 | 2017-03-21 | Anthrogenesis Corporation | Composition for collecting placental stem cells and methods of using the composition |
| WO2007111904A2 (en) | 2006-03-22 | 2007-10-04 | Vertex Pharmaceuticals Incorporated | C-met protein kinase inhibitors for the treatment of proliferative disorders |
| US20070269827A1 (en) | 2006-05-18 | 2007-11-22 | Oklahoma Medical Research Foundation | Predicting and Diagnosing Patients With Autoimmune Disease |
| KR101342035B1 (ko) | 2006-06-20 | 2013-12-16 | 한국과학기술연구원 | 신장독성 및 부작용 유발 약물 검색용 바이오마커 및 이를이용한 신장독성 및 부작용 유발 약물 검색 방법 |
| US8877780B2 (en) | 2006-08-30 | 2014-11-04 | Celgene Corporation | 5-substituted isoindoline compounds |
| JP2009092508A (ja) | 2007-10-09 | 2009-04-30 | Norihiro Nishimoto | リウマチ治療剤の効果の予測方法 |
| WO2009068621A1 (en) | 2007-11-30 | 2009-06-04 | Glaxosmithkline Biologicals S.A. | Method for classifying cancer patients as responder or non-responder to immunotherapy |
| KR100957051B1 (ko) | 2007-12-28 | 2010-05-13 | 한국과학기술연구원 | 니트로푸란토인 처리에 따른, 폐독성 유발 약물 검색용마커유전자 및 이를 이용한 검색 방법 |
| GB2456390A (en) | 2008-01-15 | 2009-07-22 | Glaxo Group Ltd | Bipolar disorder treatments |
| WO2009094592A2 (en) | 2008-01-23 | 2009-07-30 | Perlegen Sciences, Inc. | Genetic basis of alzheimer's disease and diagnosis and treatment thereof |
| US20090307180A1 (en) | 2008-03-19 | 2009-12-10 | Brandon Colby | Genetic analysis |
| US20110229498A1 (en) | 2008-05-08 | 2011-09-22 | The Johns Hopkins University | Compositions and methods for modulating an immune response |
| EP2177615A1 (en) | 2008-10-10 | 2010-04-21 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Method for a genome wide identification of expression regulatory sequences and use of genes and molecules derived thereof for the diagnosis and therapy of metabolic and/or tumorous diseases |
| US20100204265A1 (en) | 2009-02-09 | 2010-08-12 | Genelabs Technologies, Inc. | Certain Nitrogen Containing Bicyclic Chemical Entities for Treating Viral Infections |
| US9212177B2 (en) | 2009-08-05 | 2015-12-15 | Versitech Limited | Antiviral compounds and methods of making and using thereof |
| BR112012002331A2 (pt) | 2009-08-05 | 2019-09-24 | Versitech Ltd | composição antiviral, composição farmacêutica e uso de quantidade efetiva de composição farmacêutica |
| CA2778005A1 (en) | 2009-10-26 | 2011-05-12 | Abbott Laboratories | Detection of chromosomal abnormalities associated with prognosis of non small cell lung cancer |
| DK2569446T3 (en) | 2010-05-12 | 2018-10-29 | Steven E Schutzer | DIAGNOSTIC MARKERS FOR NEUROPsychiatric Disease |
| US20120142701A1 (en) | 2010-05-28 | 2012-06-07 | The University Of Hong Kong | Compounds and methods for the treatment of proliferative diseases |
| WO2011151941A1 (ja) | 2010-06-04 | 2011-12-08 | 国立大学法人東京大学 | 制御性t細胞の増殖または集積を誘導する作用を有する組成物 |
| WO2012021867A2 (en) | 2010-08-13 | 2012-02-16 | The Johns Hopkins University | A comprehensive methylome map of myeloid and lymphoid commitment from hematopoietic progenitors |
| AU2011317211B2 (en) | 2010-10-22 | 2015-04-16 | Dana-Farber Cancer Institute, Inc. | Discovery of regulatory T cells programmed to suppress an immune response |
| JP6001060B2 (ja) | 2011-06-06 | 2016-10-05 | ユニバーシティ オブ アイオワ リサーチ ファウンデーション | 筋萎縮を阻害するための方法 |
| EP2723362A1 (en) | 2011-06-21 | 2014-04-30 | Innate Pharma | NKp46-MEDIATED NK CELL TUNING |
| CN103782173B (zh) | 2011-07-01 | 2018-07-13 | 贝克曼考尔特公司 | 调节t细胞和识别、获得、以及用于治疗基于免疫的紊乱的方法 |
| CN103797120B (zh) | 2011-09-16 | 2017-04-12 | 上海长海医院 | 前列腺癌的生物学标志物、治疗靶点及其用途 |
| JP6306507B2 (ja) | 2011-12-01 | 2018-04-18 | 国立大学法人 東京大学 | 制御性t細胞の増殖または集積を誘導するヒト由来細菌 |
| US9481866B2 (en) | 2011-12-16 | 2016-11-01 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Methods of producing T cell populations enriched for stable regulatory T-cells |
| WO2013098797A2 (en) | 2011-12-31 | 2013-07-04 | Kuriakose Moni Abraham | Diagnostic tests for predicting prognosis, recurrence, resistance or sensitivity to therapy and metastatic status in cancer |
| JP6422344B2 (ja) | 2012-03-02 | 2018-11-14 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | 同種抗原反応性の制御性t細胞を増大させる方法 |
| GB201207297D0 (en) | 2012-04-26 | 2012-06-06 | Senzagen Ab | Analytical methods and arrays for use in the same |
| GB201213571D0 (en) | 2012-07-31 | 2012-09-12 | Univ Leuven Kath | Growth factor cocktail to enhnce osteogenic differentiayion of mesenchymal |
| EP2682750A1 (en) | 2012-07-02 | 2014-01-08 | Sotio a.s. | In vitro method for the diagnosis and surveillance of cancer |
| EP2903692B1 (en) | 2012-10-08 | 2019-12-25 | St. Jude Children's Research Hospital | Therapies based on control of regulatory t cell stability and function via a neuropilin-1:semaphorin axis |
| WO2014122467A1 (en) | 2013-02-06 | 2014-08-14 | Loxbridge Research Llp | Systems and methods for early disease detection and real-time disease monitoring |
| WO2014153069A2 (en) | 2013-03-14 | 2014-09-25 | Children's Medical Center Corporation | Compositions and methods for reprogramming hematopoietic stem cell lineages |
| BR112015022490A2 (pt) | 2013-03-15 | 2017-07-18 | Veracyte Inc | métodos e composições para classificação de amostras |
| US20160122821A1 (en) | 2013-06-10 | 2016-05-05 | Suregene, Llc | Genetic markers of antipsychotic response |
| GB2532672A (en) | 2013-09-09 | 2016-05-25 | Scripps Research Inst | Methods and systems for analysis of organ transplantation |
| WO2015050875A1 (en) | 2013-10-01 | 2015-04-09 | The Regents Of The University Of California | Endometriosis classifier |
| UY35790A (es) | 2013-10-21 | 2015-05-29 | Teva Pharma | Marcadores genéticos que predicen la respuesta al acetato de glatiramer |
| WO2015109212A1 (en) | 2014-01-17 | 2015-07-23 | Pfizer Inc. | Anti-il-2 antibodies and compositions and uses thereof |
| WO2015107196A1 (en) | 2014-01-20 | 2015-07-23 | Institut Curie | Use of thalidomide or analogs thereof for preventing neurologic disorders induced by brain irradiation |
| US20160058872A1 (en) * | 2014-04-14 | 2016-03-03 | Arvinas, Inc. | Imide-based modulators of proteolysis and associated methods of use |
| KR20250127179A (ko) * | 2014-04-14 | 2025-08-26 | 아비나스 오퍼레이션스, 인코포레이티드 | 단백질분해의 이미드-기초된 조절인자 및 연관된 이용 방법 |
| EP4112738B1 (en) | 2014-12-05 | 2024-07-24 | Foundation Medicine, Inc. | Multigene analysis of tumor samples |
| EP3034620A1 (en) | 2014-12-17 | 2016-06-22 | Diaxonhit | Compositions and methods for diagnosing thyroid cancer |
| WO2016103269A1 (en) | 2014-12-23 | 2016-06-30 | Ramot At Tel-Aviv University Ltd. | Populations of neural progenitor cells and methods of producing and using same |
| CA2973873A1 (en) | 2015-01-20 | 2016-07-28 | Merial, Inc. | Anthelmintic compounds, compositions and method of using thereof |
| EP3050570A1 (en) | 2015-01-31 | 2016-08-03 | Neurovision Pharma GmbH | Pharmaceutical composition consisting of a combination of G-CSF with GM-CSF |
| WO2016140974A1 (en) | 2015-03-01 | 2016-09-09 | Novena Therapeutics Inc. | Process for measuring tumor response to an initial oncology treatment |
| CA2986141C (en) | 2015-05-22 | 2020-07-28 | Biotheryx, Inc. | Compounds targeting proteins, compositions, methods, and uses thereof |
| EP3304076A4 (en) | 2015-06-02 | 2018-12-19 | Celgene Corporation | Methods for determining drug efficacy for treatment of cancer using ratios of cereblon associated proteins |
| EP3302548A4 (en) | 2015-06-03 | 2019-01-02 | Dana Farber Cancer Institute, Inc. | Methods to induce conversion of regulatory t cells into effector t cells for cancer immunotherapy |
| EP3310367A4 (en) | 2015-06-22 | 2019-02-20 | President and Fellows of Harvard College | INDUCTION OF LAMINA-PROPRIA-REGULATORY T-CELLS |
| WO2017042337A1 (en) | 2015-09-09 | 2017-03-16 | Max-Delbrück-Centrum Für Molekulare Medizin In Der Helmhotz-Gemeinschaft | Short-chain fatty acids for use in the treatment of cardiovascular disease |
| US20180250369A1 (en) | 2015-09-11 | 2018-09-06 | Ventria Bioscience, Inc. | Lactoferrin compositions and methods for modulation of t cell subtypes and treatment of autoimmune diseases |
| WO2017058881A1 (en) | 2015-09-28 | 2017-04-06 | The Trustees Of Columbia University In The City Of New York | Use of pentoxifylline with immune checkpoint-blockade therapies for the treatment of melanoma |
| KR102838444B1 (ko) | 2015-09-30 | 2025-07-24 | 더 유니버시티 코트 오브 더 유니버시티 오브 애버딘 | 탈리도마이드 유사체 및 사용 방법 |
| WO2017075465A1 (en) | 2015-10-28 | 2017-05-04 | The Broad Institute Inc. | Compositions and methods for evaluating and modulating immune responses by detecting and targeting gata3 |
| WO2017075451A1 (en) | 2015-10-28 | 2017-05-04 | The Broad Institute Inc. | Compositions and methods for evaluating and modulating immune responses by detecting and targeting pou2af1 |
| EP3368689B1 (en) | 2015-10-28 | 2020-06-17 | The Broad Institute, Inc. | Composition for modulating immune responses by use of immune cell gene signature |
| WO2017095525A1 (en) | 2015-12-04 | 2017-06-08 | David Scott | Antigen-specific t cells for inducing immune tolerance |
| WO2017161001A1 (en) | 2016-03-15 | 2017-09-21 | Children's Medical Center Corporation | Methods and compositions relating to hematopoietic stem cell expansion |
| US10759808B2 (en) | 2016-04-06 | 2020-09-01 | The Regents Of The University Of Michigan | Monofunctional intermediates for ligand-dependent target protein degradation |
| US11078247B2 (en) | 2016-05-04 | 2021-08-03 | Curevac Ag | RNA encoding a therapeutic protein |
| WO2017197056A1 (en) | 2016-05-10 | 2017-11-16 | C4 Therapeutics, Inc. | Bromodomain targeting degronimers for target protein degradation |
| WO2017197051A1 (en) | 2016-05-10 | 2017-11-16 | C4 Therapeutics, Inc. | Amine-linked c3-glutarimide degronimers for target protein degradation |
| HUE061847T2 (hu) | 2016-10-11 | 2023-08-28 | Arvinas Operations Inc | Androgén receptor célzott degradálására alkalmas vegyületek és eljárások |
| WO2018118598A1 (en) | 2016-12-23 | 2018-06-28 | Arvinas, Inc. | Compounds and methods for the targeted degradation of fetal liver kinase polypeptides |
| CN110741004B (zh) | 2016-12-23 | 2023-10-17 | 阿尔维纳斯运营股份有限公司 | 用于迅速加速性纤维肉瘤多肽的靶向降解的化合物和方法 |
| US11191741B2 (en) | 2016-12-24 | 2021-12-07 | Arvinas Operations, Inc. | Compounds and methods for the targeted degradation of enhancer of zeste homolog 2 polypeptide |
| AU2018211975B2 (en) | 2017-01-26 | 2022-05-26 | Arvinas Operations, Inc. | Modulators of estrogen receptor proteolysis and associated methods of use |
| CN106932576A (zh) | 2017-03-22 | 2017-07-07 | 山东大学深圳研究院 | 一种人调节性t细胞的免疫抑制功能的检测方法 |
| TWI793151B (zh) | 2017-08-23 | 2023-02-21 | 瑞士商諾華公司 | 3-(1-氧異吲哚啉-2-基)之氫吡啶-2,6-二酮衍生物及其用途 |
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