JP2020531498A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2020531498A5 JP2020531498A5 JP2020510565A JP2020510565A JP2020531498A5 JP 2020531498 A5 JP2020531498 A5 JP 2020531498A5 JP 2020510565 A JP2020510565 A JP 2020510565A JP 2020510565 A JP2020510565 A JP 2020510565A JP 2020531498 A5 JP2020531498 A5 JP 2020531498A5
- Authority
- JP
- Japan
- Prior art keywords
- piperidine
- dione
- oxoisoindoline
- methyl
- oxo
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 5-(1-((1-Methyl-1H-benzo [d] imidazol-2-yl) methyl) piperidine-4-yl) -1-oxoisoindoline-2-yl Chemical group 0.000 claims description 67
- 125000005842 heteroatom Chemical group 0.000 claims description 65
- 229910052757 nitrogen Inorganic materials 0.000 claims description 64
- 229910052717 sulfur Inorganic materials 0.000 claims description 59
- 229910052760 oxygen Inorganic materials 0.000 claims description 56
- 150000001875 compounds Chemical class 0.000 claims description 52
- 125000003118 aryl group Chemical group 0.000 claims description 51
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 51
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 125000004429 atom Chemical group 0.000 claims description 37
- 239000008194 pharmaceutical composition Substances 0.000 claims description 30
- KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical compound O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 claims description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 27
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 26
- 229940002612 prodrug Drugs 0.000 claims description 25
- 239000000651 prodrug Substances 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 239000012453 solvate Substances 0.000 claims description 22
- 101000599037 Homo sapiens Zinc finger protein Helios Proteins 0.000 claims description 18
- 102100037796 Zinc finger protein Helios Human genes 0.000 claims description 18
- 125000001188 haloalkyl group Chemical group 0.000 claims description 17
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 16
- 201000010099 disease Diseases 0.000 claims description 13
- 208000035475 disorder Diseases 0.000 claims description 13
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 12
- 206010028980 Neoplasm Diseases 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 11
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 10
- 208000001894 Nasopharyngeal Neoplasms Diseases 0.000 claims description 10
- 206010061306 Nasopharyngeal cancer Diseases 0.000 claims description 10
- 208000003721 Triple Negative Breast Neoplasms Diseases 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 10
- 208000022679 triple-negative breast carcinoma Diseases 0.000 claims description 10
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 10
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 201000011510 cancer Diseases 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 201000011243 gastrointestinal stromal tumor Diseases 0.000 claims description 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 108091092878 Microsatellite Proteins 0.000 claims description 5
- 208000015634 Rectal Neoplasms Diseases 0.000 claims description 5
- 208000002458 carcinoid tumor Diseases 0.000 claims description 5
- 230000000112 colonic effect Effects 0.000 claims description 5
- 201000001441 melanoma Diseases 0.000 claims description 5
- 206010038038 rectal cancer Diseases 0.000 claims description 5
- 201000001275 rectum cancer Diseases 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 4
- 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 description 4
- 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 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 208000008732 thymoma Diseases 0.000 claims description 4
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 3
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 2
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims description 2
- JBCFJMYPJJWIRG-UHFFFAOYSA-N 1,3-oxazole-4-carboxylic acid Chemical compound OC(=O)C1=COC=N1 JBCFJMYPJJWIRG-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- SMNDYUVBFMFKNZ-UHFFFAOYSA-M 2-furoate Chemical compound [O-]C(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-M 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- OAWQJVYWJYNIDW-UHFFFAOYSA-N 3-[6-[1-(1H-indol-2-ylmethyl)piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound N1C(=CC2=CC=CC=C12)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O OAWQJVYWJYNIDW-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- IWUZLDBCMHDKSS-UHFFFAOYSA-N 3-[6-[1-(imidazo[1,2-a]pyrazin-3-ylmethyl)piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound N=1C=C(N2C=1C=NC=C2)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O IWUZLDBCMHDKSS-UHFFFAOYSA-N 0.000 claims description 2
- XDOAOTSHHGEUAF-UHFFFAOYSA-N 3-[6-[1-(imidazo[1,2-a]pyrimidin-2-ylmethyl)piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound N=1C(=CN2C=1N=CC=C2)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O XDOAOTSHHGEUAF-UHFFFAOYSA-N 0.000 claims description 2
- ICQRDBKJZOZFQK-UHFFFAOYSA-N 3-[6-[1-(imidazo[1,2-a]pyrimidin-3-ylmethyl)piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound N=1C=C(N2C=1N=CC=C2)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O ICQRDBKJZOZFQK-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- YPKNBUJEWGTHBY-UHFFFAOYSA-N 3-[6-[1-[(2-methoxypyrimidin-5-yl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound COC1=NC=C(C=N1)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O YPKNBUJEWGTHBY-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- GKYORSRVLSGESP-UHFFFAOYSA-N 3-[6-[1-[(3,5-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=C(C=1)Cl GKYORSRVLSGESP-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- RQFDTXKPKPREAU-UHFFFAOYSA-N 3-[6-[1-[(4-chloro-3-fluorophenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound ClC1=C(C=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C1)F RQFDTXKPKPREAU-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- LUAJKYYOMUOAIC-UHFFFAOYSA-N 3-[6-[1-[(4-methylphenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound CC1=CC=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C1 LUAJKYYOMUOAIC-UHFFFAOYSA-N 0.000 claims description 2
- LAIOYQAJEYMJBR-UHFFFAOYSA-N 3-[6-[1-[(4-tert-butylphenyl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C)(C)(C)C1=CC=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C1 LAIOYQAJEYMJBR-UHFFFAOYSA-N 0.000 claims description 2
- STPSDNYXDFNHPF-UHFFFAOYSA-N 3-[6-[1-[(5-chlorothiophen-2-yl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound ClC1=CC=C(S1)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O STPSDNYXDFNHPF-UHFFFAOYSA-N 0.000 claims description 2
- VHBCICTUEUBWFY-UHFFFAOYSA-N 3-[6-[1-[(5-methyl-3-phenyl-1,2-oxazol-4-yl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound CC1=C(C(=NO1)C1=CC=CC=C1)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O VHBCICTUEUBWFY-UHFFFAOYSA-N 0.000 claims description 2
- CJAXCRUVVOHXGU-UHFFFAOYSA-N 3-[6-[1-[(6-aminopyridin-3-yl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound NC1=CC=C(C=N1)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O CJAXCRUVVOHXGU-UHFFFAOYSA-N 0.000 claims description 2
- SAPFFLAWNMHYCV-UHFFFAOYSA-N 3-[6-[1-[(6-methyl-1H-indol-3-yl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound CC1=CC=C2C(=CNC2=C1)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O SAPFFLAWNMHYCV-UHFFFAOYSA-N 0.000 claims description 2
- AFDKCPLAKBPUJA-UHFFFAOYSA-N 3-[6-[1-[(6-methylpyridin-2-yl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound CC1=CC=CC(=N1)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O AFDKCPLAKBPUJA-UHFFFAOYSA-N 0.000 claims description 2
- LJBBUSNWLWQUMC-UHFFFAOYSA-N 3-[6-[1-[(7-fluoroquinolin-2-yl)methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound FC1=CC=C2C=CC(=NC2=C1)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O LJBBUSNWLWQUMC-UHFFFAOYSA-N 0.000 claims description 2
- VLQAKBLKJLIIMV-UHFFFAOYSA-N 3-[6-[1-[[2-(difluoromethoxy)phenyl]methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound FC(OC1=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=CC=C1)F VLQAKBLKJLIIMV-UHFFFAOYSA-N 0.000 claims description 2
- BQLURVNBMJCGKT-UHFFFAOYSA-N 3-[6-[1-[[3,5-bis(trifluoromethyl)phenyl]methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound FC(C=1C=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C(C=1)C(F)(F)F)(F)F BQLURVNBMJCGKT-UHFFFAOYSA-N 0.000 claims description 2
- NWMHBGNWMAQFRY-UHFFFAOYSA-N 3-[6-[1-[[3-(difluoromethoxy)phenyl]methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound FC(OC=1C=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=CC=1)F NWMHBGNWMAQFRY-UHFFFAOYSA-N 0.000 claims description 2
- NDTRTDGKECFCGD-UHFFFAOYSA-N 3-[6-[1-[[3-(difluoromethyl)phenyl]methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound FC(C=1C=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=CC=1)F NDTRTDGKECFCGD-UHFFFAOYSA-N 0.000 claims description 2
- DKIXKCNLXZOQGY-UHFFFAOYSA-N 3-[6-[1-[[4-(2-methylbutan-2-yl)phenyl]methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)CC1=CC=C(C=C1)C(C)(C)CC)C1C(NC(CC1)=O)=O DKIXKCNLXZOQGY-UHFFFAOYSA-N 0.000 claims description 2
- LBHKHAUYAJVGOZ-UHFFFAOYSA-N 3-[6-[1-[[4-(2-methylpropyl)phenyl]methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound C(C(C)C)C1=CC=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C1 LBHKHAUYAJVGOZ-UHFFFAOYSA-N 0.000 claims description 2
- IMVMTNVPVNYNDP-UHFFFAOYSA-N 3-[6-[1-[[4-(4-methoxypiperidin-1-yl)phenyl]methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound COC1CCN(CC1)C1=CC=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C1 IMVMTNVPVNYNDP-UHFFFAOYSA-N 0.000 claims description 2
- TTXDSMZYJLLGAC-UHFFFAOYSA-N 3-[6-[1-[[4-(difluoromethoxy)phenyl]methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound FC(OC1=CC=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C1)F TTXDSMZYJLLGAC-UHFFFAOYSA-N 0.000 claims description 2
- NVRCBCXKQSERED-UHFFFAOYSA-N 3-[6-[1-[[4-(difluoromethyl)phenyl]methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound FC(C1=CC=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C1)F NVRCBCXKQSERED-UHFFFAOYSA-N 0.000 claims description 2
- KOFDFAVYZZNRQF-UHFFFAOYSA-N 3-[6-[1-[[4-(difluoromethylsulfonyl)phenyl]methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound FC(S(=O)(=O)C1=CC=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C1)F KOFDFAVYZZNRQF-UHFFFAOYSA-N 0.000 claims description 2
- NTOAGGFFVAPWTB-UHFFFAOYSA-N 3-[6-[1-[[4-(fluoromethyl)phenyl]methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound FCC1=CC=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C1 NTOAGGFFVAPWTB-UHFFFAOYSA-N 0.000 claims description 2
- DAGFBPSOCFDYKG-UHFFFAOYSA-N 3-[6-[1-[[4-(hydroxymethyl)phenyl]methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound OCC1=CC=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C1 DAGFBPSOCFDYKG-UHFFFAOYSA-N 0.000 claims description 2
- WXHBYRUPKDHTJJ-UHFFFAOYSA-N 3-[6-[1-[[4-(methoxymethyl)phenyl]methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound COCC1=CC=C(CN2CCC(CC2)C=2C=C3CN(C(C3=CC=2)=O)C2C(NC(CC2)=O)=O)C=C1 WXHBYRUPKDHTJJ-UHFFFAOYSA-N 0.000 claims description 2
- FIWWXTUDASPOIU-UHFFFAOYSA-N 3-[6-[1-[[4-[(4-fluorophenyl)methoxy]phenyl]methyl]piperidin-4-yl]-3-oxo-1H-isoindol-2-yl]piperidine-2,6-dione Chemical compound FC1=CC=C(COC2=CC=C(CN3CCC(CC3)C=3C=C4CN(C(C4=CC=3)=O)C3C(NC(CC3)=O)=O)C=C2)C=C1 FIWWXTUDASPOIU-UHFFFAOYSA-N 0.000 claims description 2
- RVKLQHOHPVBRBF-UHFFFAOYSA-N 3-[[4-[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]piperidin-1-yl]methyl]-1,2,4-oxadiazole-5-carboxamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)C1CCN(CC1)CC1=NOC(=N1)C(=O)N)=O)=O RVKLQHOHPVBRBF-UHFFFAOYSA-N 0.000 claims description 2
- HJHYQGLDRQGYIS-UHFFFAOYSA-N 3-[[4-[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]piperidin-1-yl]methyl]benzoic acid Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)C1CCN(CC1)CC=1C=C(C(=O)O)C=CC=1)=O)=O HJHYQGLDRQGYIS-UHFFFAOYSA-N 0.000 claims description 2
- RTUISXSZWCJACT-UHFFFAOYSA-N 3-[[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)CC=1C=C(C#N)C=CC=1)=O)=O RTUISXSZWCJACT-UHFFFAOYSA-N 0.000 claims description 2
- MHYYTONIFDSRKT-UHFFFAOYSA-N 4-[[4-[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]piperidin-1-yl]methyl]-N,N-dimethylbenzenesulfonamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)C1CCN(CC1)CC1=CC=C(C=C1)S(=O)(=O)N(C)C)=O)=O MHYYTONIFDSRKT-UHFFFAOYSA-N 0.000 claims description 2
- ZKJBVLDYYTVASX-UHFFFAOYSA-N 4-[[4-[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]piperidin-1-yl]methyl]benzoic acid Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)C1CCN(CC1)CC1=CC=C(C(=O)O)C=C1)=O)=O ZKJBVLDYYTVASX-UHFFFAOYSA-N 0.000 claims description 2
- IGSUFVWRYGOCGD-UHFFFAOYSA-N 4-[[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=CC=C(C#N)C=C1)=O)=O IGSUFVWRYGOCGD-UHFFFAOYSA-N 0.000 claims description 2
- XZLWFILEWAZFKN-UHFFFAOYSA-N 5-[[4-[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]piperidin-1-yl]methyl]-2-fluorobenzonitrile Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)C1CCN(CC1)CC=1C=CC(=C(C#N)C=1)F)=O)=O XZLWFILEWAZFKN-UHFFFAOYSA-N 0.000 claims description 2
- 208000003200 Adenoma Diseases 0.000 claims description 2
- 206010001233 Adenoma benign Diseases 0.000 claims description 2
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 2
- VZBPAOVDFZAYTC-UHFFFAOYSA-N C1CC(CNC1)N2CC3=C(C2=O)C=CC(=C3)C4CCN(CC4)CC5=CC6=C(C=C5)OCCO6 Chemical compound C1CC(CNC1)N2CC3=C(C2=O)C=CC(=C3)C4CCN(CC4)CC5=CC6=C(C=C5)OCCO6 VZBPAOVDFZAYTC-UHFFFAOYSA-N 0.000 claims description 2
- GLUDROWSXUOHDN-DOQZHRMPSA-N CO[C@@H]1CC[C@H](CC1)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O Chemical compound CO[C@@H]1CC[C@H](CC1)CN1CCC(CC1)C=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O GLUDROWSXUOHDN-DOQZHRMPSA-N 0.000 claims description 2
- 206010007275 Carcinoid tumour Diseases 0.000 claims description 2
- 206010051066 Gastrointestinal stromal tumour Diseases 0.000 claims description 2
- IMGFNTJISKQBSY-UHFFFAOYSA-N N-[4-[[4-[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]piperidin-1-yl]methyl]phenyl]acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)C1CCN(CC1)CC1=CC=C(C=C1)NC(C)=O)=O)=O IMGFNTJISKQBSY-UHFFFAOYSA-N 0.000 claims description 2
- OLFQTJRFOVKFDN-UHFFFAOYSA-N O=C(C1=CC=C(C2CCN(CC(C=C3)=CC(O4)=C3OC4(F)F)CC2)C=C1C1)N1C1CNCCC1 Chemical compound O=C(C1=CC=C(C2CCN(CC(C=C3)=CC(O4)=C3OC4(F)F)CC2)C=C1C1)N1C1CNCCC1 OLFQTJRFOVKFDN-UHFFFAOYSA-N 0.000 claims description 2
- SYTTVOCIBRVYHX-UHFFFAOYSA-N O=C(C1=CC=C(C2CCN(CC3=CC=CC4=C3OCCO4)CC2)C=C1C1)N1C1CNCCC1 Chemical compound O=C(C1=CC=C(C2CCN(CC3=CC=CC4=C3OCCO4)CC2)C=C1C1)N1C1CNCCC1 SYTTVOCIBRVYHX-UHFFFAOYSA-N 0.000 claims description 2
- PUDAGHRDBJIKRE-AHUVTLGMSA-N O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)C[C@@H]1CC[C@H](CC1)C(F)(F)F)C1C(NC(CC1)=O)=O Chemical compound O=C1N(CC2=CC(=CC=C12)C1CCN(CC1)C[C@@H]1CC[C@H](CC1)C(F)(F)F)C1C(NC(CC1)=O)=O PUDAGHRDBJIKRE-AHUVTLGMSA-N 0.000 claims description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 2
- 230000033228 biological regulation Effects 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 230000004663 cell proliferation Effects 0.000 claims description 2
- 230000000593 degrading effect Effects 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 230000028993 immune response Effects 0.000 claims description 2
- 230000002163 immunogen Effects 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 230000001105 regulatory effect Effects 0.000 claims description 2
- 210000000115 thoracic cavity Anatomy 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 150000004677 hydrates Chemical class 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 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
- 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
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims 1
- 238000000034 method Methods 0.000 description 14
- 0 *C(CCC(N1)=C)(C1=O)N(Cc1cc(*2C*C*N(*)CC2)ccc11)C1=O Chemical compound *C(CCC(N1)=C)(C1=O)N(Cc1cc(*2C*C*N(*)CC2)ccc11)C1=O 0.000 description 5
- 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 description 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 description 1
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762549225P | 2017-08-23 | 2017-08-23 | |
| US62/549,225 | 2017-08-23 | ||
| PCT/IB2018/056400 WO2019038717A1 (en) | 2017-08-23 | 2018-08-23 | 3- (1-OXOISOINDOLIN-2-YL) PIPERIDINE-2,6-DIONE DERIVATIVES AND USES THEREOF |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020531498A JP2020531498A (ja) | 2020-11-05 |
| JP2020531498A5 true JP2020531498A5 (enExample) | 2021-09-30 |
| JP7386787B2 JP7386787B2 (ja) | 2023-11-27 |
Family
ID=63638171
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020510565A Active JP7386787B2 (ja) | 2017-08-23 | 2018-08-23 | ３－（１－オキソイソインドリン－２－イル）ピペリジン－２，６－ジオン誘導体及びその使用 |
Country Status (39)
Families Citing this family (76)
| 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 |
| CN109562107A (zh) | 2016-05-10 | 2019-04-02 | C4医药公司 | 用于靶蛋白降解的杂环降解决定子体 |
| 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 |
| CA3095912A1 (en) * | 2018-04-13 | 2019-10-17 | Arvinas Operations, Inc. | Cereblon ligands and bifunctional compounds comprising the same |
| BR122022012697B1 (pt) * | 2018-07-10 | 2023-04-04 | Novartis Ag | Usos de derivados de 3-(5-hidróxi-1-oxoisoindolin-2-il)piperidina-2,6- diona, e kit |
| 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 |
| CN113490495B (zh) | 2018-12-03 | 2024-09-27 | 达纳-法伯癌症研究公司 | Helios的小分子降解剂及其使用方法 |
| AU2019402189B2 (en) * | 2018-12-20 | 2023-04-13 | Novartis Ag | Dosing regimen and pharmaceutical combination comprising 3-(1-oxoisoindolin-2-yl)piperidine-2,6-dione derivatives |
| 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 |
| CA3123519A1 (en) | 2019-02-15 | 2020-08-20 | Novartis Ag | Substituted 3-(1-oxoisoindolin-2-yl)piperidine-2,6-dione derivatives and uses thereof |
| EP3932922A4 (en) | 2019-02-25 | 2022-05-11 | ShanghaiTech University | SULPHUR-CONTAINING COMPOUND BASED ON A GLUTARIMIDE FRAMEWORK AND ITS USE |
| KR102947433B1 (ko) * | 2019-04-12 | 2026-04-06 | 씨4 테라퓨틱스, 인코포레이티드 | 이카로스 및 아이올로스의 트리시클릭 분해제 |
| WO2020219742A1 (en) | 2019-04-24 | 2020-10-29 | Novartis Ag | Compositions and methods for selective protein degradation |
| US11458149B1 (en) | 2019-05-31 | 2022-10-04 | Ikena Oncology, Inc. | TEAD inhibitors and uses thereof |
| BR112021024108A2 (pt) | 2019-05-31 | 2022-03-22 | Ikena Oncology Inc | Inibidores de tead e usos dos mesmos |
| WO2021023233A1 (zh) | 2019-08-05 | 2021-02-11 | 上海科技大学 | Egfr蛋白降解剂及其抗肿瘤应用 |
| WO2021087093A1 (en) * | 2019-10-30 | 2021-05-06 | 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 |
| JP7629459B2 (ja) * | 2019-11-19 | 2025-02-13 | ブリストル－マイヤーズ スクイブ カンパニー | Ｈｅｌｉｏｓタンパク質の阻害剤として有用な化合物 |
| 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 |
| EP4144728A4 (en) * | 2020-04-30 | 2023-08-23 | Shanghaitech University | HETEROCYCLIC COMPOUND BASED ON A GLUTARIMIDE SKELETON AND USES THEREOF |
| EP4168007A1 (en) | 2020-06-23 | 2023-04-26 | Novartis AG | Dosing regimen comprising 3-(1-oxoisoindolin-2-yl)piperidine-2,6-dione derivatives |
| TW202216684A (zh) * | 2020-07-09 | 2022-05-01 | 大陸商四川海思科製藥有限公司 | 用於抑制與降解雄激素受體的化合物、醫藥組合物及其應用 |
| AU2021319847A1 (en) * | 2020-08-03 | 2023-03-02 | Captor Therapeutics S.A. | Low molecular weight protein degraders and their applications |
| EP4188549A1 (en) * | 2020-08-03 | 2023-06-07 | Novartis AG | Heteroaryl substituted 3-(1-oxoisoindolin-2-yl)piperidine-2,6-dione derivatives and uses thereof |
| WO2022066835A1 (en) | 2020-09-23 | 2022-03-31 | 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 |
| CN122562781A (zh) * | 2020-10-07 | 2026-08-14 | 上海睿跃生物科技有限公司 | 治疗癌症的化合物和方法 |
| JP7863100B2 (ja) * | 2020-10-14 | 2026-05-20 | シーフォー セラピューティクス， インコーポレイテッド | Ｉｋｚｆ２又はｉｋｚｆ４を分解する三環式リガンド |
| 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 |
| IL301690A (en) * | 2020-10-16 | 2023-05-01 | Dana Farber Cancer Inst 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. |
| PE20231941A1 (es) | 2021-04-06 | 2023-12-05 | Bristol Myers Squibb Co | Compuestos de oxoisoindolina sustituidos con piridinilo |
| US20240239785A1 (en) * | 2021-04-29 | 2024-07-18 | Neomorph, Inc. | Substituted 2-(2,6-dioxopiperidin-3-yl)-5-(1-piperidin-4-yl)isoindoline-1,3-dione derivatives and uses thereof |
| EP4329746A4 (en) * | 2021-04-29 | 2025-03-19 | Dana-Farber Cancer Institute, Inc. | Phthalimido cereblon complex binders and transcription factor degraders and methods of use |
| TW202317546A (zh) | 2021-07-09 | 2023-05-01 | 美商普萊克斯姆公司 | 調節ikzf2之芳基化合物及醫藥組合物 |
| JP2024528988A (ja) | 2021-08-06 | 2024-08-01 | セルジーン コーポレーション | 改変タンパク質の選択的分解のための組成物および方法 |
| WO2023016518A1 (zh) * | 2021-08-11 | 2023-02-16 | 四川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 |
| JP2024539269A (ja) * | 2021-10-22 | 2024-10-28 | グルータクス セラピューティクス （シャンハイ） カンパニー、リミテッド | Ｃｒｂｎ ｅ３リガーゼリガンド化合物、当該リガンド化合物に基づいて開発したタンパク質分解剤及びそれらの応用 |
| EP4423078A1 (en) | 2021-10-28 | 2024-09-04 | Gilead Sciences, Inc. | Pyridizin-3(2h)-one derivatives |
| PE20241186A1 (es) | 2021-10-29 | 2024-06-03 | Gilead Sciences Inc | Compuestos de cd73 |
| CN118488948A (zh) | 2021-12-22 | 2024-08-13 | 吉利德科学公司 | Ikaros锌指家族降解剂及其用途 |
| US20240124412A1 (en) | 2021-12-22 | 2024-04-18 | Gilead Sciences, Inc. | Ikaros zinc finger family degraders and uses thereof |
| CA3248911A1 (en) | 2022-01-28 | 2023-08-03 | Gilead Sciences, Inc. | POLY(ADENOSINE DIPHOSPHATE-RIBOSE) POLYMERASE 7 INHIBITORS |
| 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 |
| PL4245756T3 (pl) | 2022-03-17 | 2025-02-17 | Gilead Sciences, Inc. | Środki degradujące palec cynkowy z rodziny ikaros i ich zastosowania |
| US20250214991A1 (en) * | 2022-03-25 | 2025-07-03 | Oncopia Therapeutics, Inc. D/B/A/ Sk Life Science Labs | Bicyclic heteroaryl-containing compounds as ikzf2 degraders |
| TW202341988A (zh) * | 2022-03-25 | 2023-11-01 | 密西根大學董事會 | Ｉｋｚｆ２降解劑及其用途 |
| WO2023201012A1 (en) * | 2022-04-15 | 2023-10-19 | Regents Of The University Of Michigan | Ikzf2 degraders and uses thereof |
| EP4511127A1 (en) | 2022-04-21 | 2025-02-26 | Gilead Sciences, Inc. | Kras g12d modulating compounds |
| WO2024006929A1 (en) | 2022-07-01 | 2024-01-04 | Gilead Sciences, Inc. | Cd73 compounds |
| US20260028326A1 (en) * | 2022-08-10 | 2026-01-29 | Gluetacs Therapeutics (Shanghai) Co., Ltd. | Compound based on isoindoline-substituted glutarimide backbone and use thereof |
| WO2024059107A1 (en) * | 2022-09-14 | 2024-03-21 | President And Fellows Of Harvard College | Ikzf2 and ck1-alpha degrading compounds and uses thereof |
| US20260199316A1 (en) * | 2022-12-07 | 2026-07-16 | Hangzhou Glubio Pharmaceutical Co., Ltd | Solid dispersion, preparation method therefor, and use thereof |
| 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 |
| PE20260121A1 (es) | 2023-04-21 | 2026-01-16 | Gilead Sciences Inc | Inhibidores de prmt5 y usos de los mismos |
| JP2026522894A (ja) | 2023-06-30 | 2026-07-09 | ギリアード サイエンシーズ， インコーポレイテッド | Ｋｒａｓ調節化合物 |
| AU2024297978A1 (en) | 2023-07-26 | 2026-02-05 | Gilead Sciences, Inc. | Parp7 inhibitors |
| CN121568935A (zh) | 2023-07-26 | 2026-02-24 | 吉利德科学公司 | Parp7抑制剂 |
| US20250109147A1 (en) | 2023-09-08 | 2025-04-03 | Gilead Sciences, Inc. | Kras g12d modulating compounds |
| EP4774280A1 (en) | 2023-09-08 | 2026-07-15 | 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 |
| TW202530189A (zh) | 2023-09-29 | 2025-08-01 | 日商第一三共股份有限公司 | ３－苯基丙基胺衍生物 |
| WO2025076284A1 (en) * | 2023-10-06 | 2025-04-10 | Delphia Therapeutics, Inc. | Compounds, pharmaceutical compositions thereof, and methods of using the same |
| WO2025096589A1 (en) | 2023-11-03 | 2025-05-08 | Gilead Sciences, Inc. | Prmt5 inhibitors and uses thereof |
| TW202540200A (zh) | 2023-12-01 | 2025-10-16 | 美商基利科學股份有限公司 | 抗ｆａｐ－ｌｉｇｈｔ融合蛋白及其用途 |
| US20250230168A1 (en) | 2023-12-22 | 2025-07-17 | Gilead Sciences, Inc. | Azaspiro wrn inhibitors |
| WO2025245178A1 (en) * | 2024-05-21 | 2025-11-27 | Innovo Therapeutics, Inc. | Pak4, cstf2, or cstf2t protein degraders, pharmaceutical compositions, and therapeutic applications |
| WO2025245003A1 (en) | 2024-05-21 | 2025-11-27 | Gilead Sciences, Inc. | Prmt5 inhibitors and uses thereof |
| WO2026035999A1 (en) | 2024-08-09 | 2026-02-12 | Triana Biomedicines, Inc. | Anaplastic lymphoma kinase (alk) degraders and uses thereof |
| US20260098049A1 (en) | 2024-08-12 | 2026-04-09 | Gilead Sciences, Inc. | Kras modulating compounds |
| US20260130893A1 (en) | 2024-10-21 | 2026-05-14 | Gilead Sciences, Inc. | Prmt5 inhibitors and uses thereof |
| US20260146050A1 (en) | 2024-11-27 | 2026-05-28 | Boehringer Ingelheim International Gmbh | Kras degrading compounds comprising spirocyclic annulated 2 amino-3-cyano thiophenes |
| WO2026136515A1 (en) | 2024-12-19 | 2026-06-25 | Gilead Sciences, Inc. | Parp7 inhibitors |
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 |
| DE69740140D1 (de) * | 1996-07-24 | 2011-04-14 | Celgene Corp | Substituierte 2-(2,6-Dioxopiperidin-3-yl)-phthalimide und Oxoisoindoline und Verfahren zur Verringerung der TNF-Alpha-Stufen |
| WO2002044372A2 (en) | 2000-12-01 | 2002-06-06 | Parker Hughes Institute | Nucleotide and protein sequence of helios 3 and methods of use |
| US7902179B2 (en) * | 2001-04-26 | 2011-03-08 | Ajinomoto Co., Inc. | Heterocyclic compounds |
| DE60231989D1 (de) | 2001-08-06 | 2009-05-28 | Childrens Medical Center | Antiangiogenese wirkung von stickstoffsubstituierten thalidomid-analoga |
| 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 |
| 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 |
| 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 |
| NZ554068A (en) * | 2004-09-03 | 2009-07-31 | Celgene Corp | Processes for the preparation of substituted 2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindo-lines |
| 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 |
| AU2005311888A1 (en) | 2004-12-01 | 2006-06-08 | Celgene Corporation | Compositions comprising immunomodulatory compounds and the use thereof for the treatment of immunodeficiency disorders |
| US20090215036A1 (en) | 2004-12-10 | 2009-08-27 | Bayer Healthcare Ag | Genetic Alterations Useful For The Response Prediction of Malignant Neoplasia to Taxane-Based Medical Treatments |
| US20070128636A1 (en) | 2005-12-05 | 2007-06-07 | Baker Joffre B | 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 |
| KR20090007347A (ko) | 2006-03-22 | 2009-01-16 | 버텍스 파마슈티칼스 인코포레이티드 | 증식성 장애의 치료를 위한 ｃ-ＭＥＴ 단백질 키나제 억제제 |
| 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 |
| US20100247580A1 (en) | 2007-11-30 | 2010-09-30 | Thierry Coche | 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 |
| US20090307181A1 (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 |
| RU2012104214A (ru) | 2009-08-05 | 2013-09-10 | Верситек Лимитед | Противовирусные соединения и способы их получения и применения |
| EP2494076B1 (en) | 2009-10-26 | 2017-11-22 | Abbott Molecular Inc. | 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 |
| CN106822153B (zh) | 2011-06-06 | 2019-12-17 | 爱荷华大学研究基金会 | 用于抑制肌萎缩的方法 |
| WO2012175613A1 (en) | 2011-06-21 | 2012-12-27 | Innate Pharma | NKp46-MEDIATED NK CELL TUNING |
| EP2726879B1 (en) | 2011-07-01 | 2022-10-19 | Beckman Coulter, Inc. | Requlatory t cells and methods of identifying and isolating them using cd6 -expression or the combination of cd4, cd25 and cd127 |
| 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 |
| CA2892588A1 (en) | 2011-12-01 | 2013-06-06 | School Corporation, Azabu Veterinary Medicine Educational Institution | Human-derived bacteria that induce proliferation or accumulation of regulatory t cells |
| 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 |
| IN2014CN04935A (enExample) | 2011-12-31 | 2015-09-18 | Moni Abraham Kuriakose | |
| WO2013131045A1 (en) | 2012-03-02 | 2013-09-06 | The Regents Of The University Of California | Expansion of alloantigen-reactive regulatory t cells |
| 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 |
| EP3677310A1 (en) | 2012-10-08 | 2020-07-08 | 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 |
| EP2970881A4 (en) | 2013-03-14 | 2017-01-25 | 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 |
| WO2014200952A2 (en) | 2013-06-10 | 2014-12-18 | Suregene, Llc | Genetic markers of antipsychotic response |
| EP3044333A4 (en) | 2013-09-09 | 2017-08-09 | The Scripps Research Institute | Methods and systems for analysis of organ transplantation |
| US10927412B2 (en) | 2013-10-01 | 2021-02-23 | 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 |
| EP4649963A3 (en) * | 2014-04-14 | 2026-05-13 | Arvinas Operations, Inc. | Imide-based modulators of proteolysis and associated methods of use |
| ES2989276T3 (es) | 2014-12-05 | 2024-11-25 | Found Medicine Inc | Análisis multigénico de muestras tumorales |
| 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 |
| ES2907461T3 (es) | 2015-01-20 | 2022-04-25 | Boehringer Ingelheim Animal Health Usa Inc | Compuestos antihelmínticos, composiciones y procedimientos de uso de los mismos |
| 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 |
| AU2016266942B2 (en) | 2015-05-22 | 2018-10-18 | Biotheryx, Inc. | Compounds targeting proteins, compositions, methods, and uses thereof |
| WO2016196580A1 (en) | 2015-06-02 | 2016-12-08 | Celgene Corporation | Methods for determining drug efficacy for treatment of cancer using ratios of cereblon associated proteins |
| WO2016196912A1 (en) | 2015-06-03 | 2016-12-08 | Dana-Farber Cancer Institute, Inc. | Methods to induce conversion of regulatory t cells into effector t cells for cancer immunotherapy |
| EA201890097A1 (ru) | 2015-06-22 | 2018-07-31 | Президент Энд Феллоуз Оф Гарвард Колледж | Индукция регуляторных т-клеток lamina propria |
| 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 |
| US10954300B2 (en) | 2015-09-28 | 2021-03-23 | The Trustees Of Columbia University In The City Of New York | Use of pentoxifylline with immune checkpoint-blockade therapies for the treatment of melanoma |
| CA3000661C (en) | 2015-09-30 | 2024-04-02 | Nigel H. Greig | Thalidomide analogs and methods of use |
| 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 |
| 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 |
| WO2017075478A2 (en) | 2015-10-28 | 2017-05-04 | The Broad Institute Inc. | Compositions and methods for evaluating and modulating immune responses by use of immune cell gene signatures |
| US11090373B2 (en) | 2015-12-04 | 2021-08-17 | The Henry M. Jackson Foundation For The Advancement Of Military Medicine, Inc. | 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 |
| EP3440082A1 (en) | 2016-04-06 | 2019-02-13 | The Regents of The University of Michigan | Monofunctional intermediates for ligand-dependent target protein degradation |
| WO2017191274A2 (en) | 2016-05-04 | 2017-11-09 | 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 |
| CN121974842A (zh) | 2016-05-10 | 2026-05-05 | C4医药公司 | 用于靶蛋白降解的胺连接的c3-戊二酰亚胺降解决定子体 |
| SI3526202T1 (sl) | 2016-10-11 | 2025-04-30 | Arvinas Operations, Inc. | Spojine in postopki za ciljno razgradnjo androgenskih receptorjev |
| US10806737B2 (en) | 2016-12-23 | 2020-10-20 | Arvinas Operations, Inc. | Compounds and methods for the targeted degradation of fetal liver kinase polypeptides |
| IL325835A (en) | 2016-12-23 | 2026-03-01 | Univ Yale | Compounds and methods for the targeted degradation of rapidly accelerated fibrosarcoma polypeptides |
| 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 |
| IL300417A (en) * | 2017-01-26 | 2023-04-01 | Arvinas Operations Inc | Bifunctional benzothiophene compounds, preparations containing them and their use in therapy |
| 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 |
-
2018
- 2018-08-21 TW TW107129068A patent/TWI793151B/zh not_active IP Right Cessation
- 2018-08-22 UY UY0001037854A patent/UY37854A/es not_active Application Discontinuation
- 2018-08-22 AR ARP180102390 patent/AR112529A1/es not_active Application Discontinuation
- 2018-08-22 US US16/108,713 patent/US10414755B2/en active Active
- 2018-08-23 CA CA3072694A patent/CA3072694A1/en active Pending
- 2018-08-23 SG SG11202000490PA patent/SG11202000490PA/en unknown
- 2018-08-23 MX MX2020002060A patent/MX2020002060A/es unknown
- 2018-08-23 AU AU2018319577A patent/AU2018319577B2/en not_active Ceased
- 2018-08-23 RS RS20230203A patent/RS64058B9/sr unknown
- 2018-08-23 CN CN201880053653.2A patent/CN111051298B/zh active Active
- 2018-08-23 MA MA49952A patent/MA49952B1/fr unknown
- 2018-08-23 EA EA202090553A patent/EA202090553A1/ru unknown
- 2018-08-23 PL PL18772885.2T patent/PL3672949T3/pl unknown
- 2018-08-23 HU HUE18772885A patent/HUE061895T2/hu unknown
- 2018-08-23 CU CU2020000014A patent/CU20200014A7/es unknown
- 2018-08-23 PT PT187728852T patent/PT3672949T/pt unknown
- 2018-08-23 JO JOP/2020/0042A patent/JOP20200042A1/ar unknown
- 2018-08-23 ES ES18772885T patent/ES2940448T3/es active Active
- 2018-08-23 CR CR20200081A patent/CR20200081A/es unknown
- 2018-08-23 EP EP22213789.5A patent/EP4183782A1/en not_active Withdrawn
- 2018-08-23 BR BR112020003373-1A patent/BR112020003373B1/pt not_active IP Right Cessation
- 2018-08-23 HR HRP20230244TT patent/HRP20230244T1/hr unknown
- 2018-08-23 SI SI201830871T patent/SI3672949T1/sl unknown
- 2018-08-23 DK DK18772885.2T patent/DK3672949T5/da active
- 2018-08-23 EP EP18772885.2A patent/EP3672949B9/en active Active
- 2018-08-23 PE PE2020000271A patent/PE20200796A1/es unknown
- 2018-08-23 KR KR1020207007884A patent/KR20200044038A/ko not_active Ceased
- 2018-08-23 LT LTEPPCT/IB2018/056400T patent/LT3672949T/lt unknown
- 2018-08-23 JP JP2020510565A patent/JP7386787B2/ja active Active
- 2018-08-23 FI FIEP18772885.2T patent/FI3672949T3/fi active
- 2018-08-23 WO PCT/IB2018/056400 patent/WO2019038717A1/en not_active Ceased
-
2019
- 2019-08-05 US US16/532,106 patent/US10640489B2/en active Active
- 2019-08-05 US US16/532,118 patent/US10647701B2/en not_active Expired - Fee Related
-
2020
- 2020-01-13 ZA ZA2020/00208A patent/ZA202000208B/en unknown
- 2020-01-17 PH PH12020500125A patent/PH12020500125A1/en unknown
- 2020-02-18 IL IL272748A patent/IL272748B2/en unknown
- 2020-02-20 CL CL2020000427A patent/CL2020000427A1/es unknown
- 2020-02-20 CO CONC2020/0001860A patent/CO2020001860A2/es unknown
- 2020-02-20 DO DO2020000037A patent/DOP2020000037A/es unknown
- 2020-02-20 SA SA520411325A patent/SA520411325B1/ar unknown
- 2020-02-20 EC ECSENADI202013248A patent/ECSP20013248A/es unknown
- 2020-03-31 US US16/835,938 patent/US11053218B2/en not_active Expired - Fee Related
- 2020-11-26 AU AU2020277231A patent/AU2020277231A1/en not_active Abandoned
-
2021
- 2021-06-09 US US17/343,016 patent/US20210309638A1/en not_active Abandoned
-
2022
- 2022-09-13 AU AU2022231670A patent/AU2022231670A1/en not_active Abandoned
-
2023
- 2023-03-17 CY CY20231100149T patent/CY1125897T1/el unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HRP20230244T1 (hr) | Derivati 3-(1-oksoizoindolin-2-il)piperidin-2,6-diona i njihova upotreba | |
| JP6373978B2 (ja) | イミダゾピロリジノン誘導体および疾患の処置におけるその使用 | |
| JP4579346B2 (ja) | アミノ複素環式化合物 | |
| JP5576802B2 (ja) | Ｃ−Ｍｅｔチロシンキナーゼ介在疾患の治療用のイミダゾ［１，２−ｂ］ピリダジン誘導体 | |
| RU2473549C2 (ru) | Пиримидиновые соединения, композиции и способы применения | |
| JP6211556B2 (ja) | イミダゾ［１，２−ａ］ピリジン化合物 | |
| JP2013523884A5 (enExample) | ||
| JP5918217B2 (ja) | 特定のアミノピリダジン、その組成物、及びこれらの使用方法 | |
| JP6571173B2 (ja) | 一過性受容体電位ａ１イオンチャネルの阻害 | |
| JP5987005B2 (ja) | オレキシン拮抗薬として有用な新規なピラゾール及びイミダゾール誘導体 | |
| RU2008141761A (ru) | ИНГИБИТОРЫ с-МЕТ ПРОТЕИНКИНАЗЫ | |
| JP2022531801A5 (enExample) | ||
| TW202039489A (zh) | Mat2a之雜雙環抑制劑及用於治療癌症之使用方法 | |
| JP2016523911A5 (enExample) | ||
| US10072003B2 (en) | Tetrahydronaphthyridine derivatives as mGluR2-negative allosteric modulators, compositions, and their use | |
| US20210379056A1 (en) | Substituted pyrazole fused ring derivative, preparation method therefor, and application thereof | |
| JP2011503166A5 (enExample) | ||
| JP2018522046A5 (enExample) | ||
| JP2013534902A5 (enExample) | ||
| JP2017530960A5 (enExample) | ||
| RU2012139830A (ru) | Производные пиразолопиперидина в качестве ингибиторов nadph - оксидазы | |
| WO2008072778A1 (ja) | 尿路系疾患の処置剤 | |
| CN102574847A (zh) | 作为syk激酶抑制剂的化合物和组合物 | |
| JP2012504639A (ja) | ドライアイおよび他の目に関連する疾患を治療するためのヤヌスキナーゼ阻害剤 | |
| CA2671982A1 (en) | Methods of using mek inhibitors |