JPWO2021138498A5 - - Google Patents
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- JPWO2021138498A5 JPWO2021138498A5 JP2022540916A JP2022540916A JPWO2021138498A5 JP WO2021138498 A5 JPWO2021138498 A5 JP WO2021138498A5 JP 2022540916 A JP2022540916 A JP 2022540916A JP 2022540916 A JP2022540916 A JP 2022540916A JP WO2021138498 A5 JPWO2021138498 A5 JP WO2021138498A5
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- 125000003275 alpha amino acid group Chemical group 0.000 claims description 242
- 125000000217 alkyl group Chemical group 0.000 claims description 108
- 101000678236 Homo sapiens 5'-nucleotidase Proteins 0.000 claims description 68
- 102000045309 human NT5E Human genes 0.000 claims description 67
- 150000003839 salts Chemical class 0.000 claims description 51
- 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims description 46
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 42
- 125000001424 substituent group Chemical group 0.000 claims description 42
- 125000001475 halogen functional group Chemical group 0.000 claims description 39
- 239000003112 inhibitor Substances 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 18
- 229940127272 CD73 inhibitor Drugs 0.000 claims description 15
- VAZQLKLWNFTTFT-UHFFFAOYSA-N 3-[8-amino-5-(1-methyl-6-oxopyridazin-3-yl)-2-(pyridin-2-ylmethyl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]benzonitrile Chemical compound N1=C(C=2N(N=C(N=2)CC2=CC=CC=N2)C(=C1C1=CC(C#N)=CC=C1)C=1C=CC(=O)N(N=1)C)N VAZQLKLWNFTTFT-UHFFFAOYSA-N 0.000 claims description 14
- 150000001413 amino acids Chemical class 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 206010028980 Neoplasm Diseases 0.000 claims description 10
- 201000011510 cancer Diseases 0.000 claims description 10
- FWMNVWWHGCHHJJ-SKKKGAJSSA-N 4-amino-1-[(2r)-6-amino-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]piperidine-4-carboxylic acid Chemical compound C([C@H](C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCCCN)C(=O)N1CCC(N)(CC1)C(O)=O)NC(=O)[C@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 FWMNVWWHGCHHJJ-SKKKGAJSSA-N 0.000 claims description 8
- 108010047041 Complementarity Determining Regions Proteins 0.000 claims description 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 8
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
- 101150051188 Adora2a gene Proteins 0.000 claims description 6
- 101150078577 Adora2b gene Proteins 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- AQOSXEZNVWHOHG-UHFFFAOYSA-N NC1=NC(=C(C=2N1N=C(N=2)CN1N=C(N=N1)C1=NC=CC=C1)C1=NC=NC=C1)C=1C=C(C#N)C=CC=1 Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CN1N=C(N=N1)C1=NC=CC=C1)C1=NC=NC=C1)C=1C=C(C#N)C=CC=1 AQOSXEZNVWHOHG-UHFFFAOYSA-N 0.000 claims description 5
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 claims description 4
- -1 pyrrolidinonyl Chemical group 0.000 claims description 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- BUXIAWLTBSXYSW-UHFFFAOYSA-N 3-[2-amino-6-[1-[[6-(2-hydroxypropan-2-yl)pyridin-2-yl]methyl]triazol-4-yl]pyrimidin-4-yl]-2-methylbenzonitrile Chemical compound CC1=C(C=CC=C1C1=CC(=NC(N)=N1)C1=CN(CC2=NC(=CC=C2)C(C)(C)O)N=N1)C#N BUXIAWLTBSXYSW-UHFFFAOYSA-N 0.000 claims description 2
- UWNQHIDMVGEEFD-UHFFFAOYSA-N 3-[4-amino-2-(pyridin-2-ylmethyl)-7-pyrimidin-4-yltriazolo[4,5-c]pyridin-6-yl]benzonitrile Chemical compound N1=C(C=2C(C(C1=C1C=C(C#N)C=C[CH]1)=C1C=CN=C[N]1)=NN(N=2)CC1=CC=CC=N1)N UWNQHIDMVGEEFD-UHFFFAOYSA-N 0.000 claims description 2
- UDTYMQWVZMEAGS-UHFFFAOYSA-N 3-[4-amino-2-[(3-fluoropyridin-2-yl)methyl]-7-pyridin-4-yltriazolo[4,5-c]pyridin-6-yl]benzonitrile Chemical compound N1=C(C=2C(C(C1=C1C=C(C#N)C=C[CH]1)=C1C=CN=C[CH]1)=NN(N=2)CC1=C(F)C=CC=N1)N UDTYMQWVZMEAGS-UHFFFAOYSA-N 0.000 claims description 2
- MSXIFXOIITVIOS-UHFFFAOYSA-N 3-[4-amino-2-[(3-fluoropyridin-2-yl)methyl]-7-pyrimidin-4-yltriazolo[4,5-c]pyridin-6-yl]benzonitrile Chemical compound NC1=NC(=C(C=2C1=NN(N=2)CC1=NC=CC=C1F)C1=NC=NC=C1)C=1C=C(C#N)C=CC=1 MSXIFXOIITVIOS-UHFFFAOYSA-N 0.000 claims description 2
- WDIMPXNTABEEDG-UHFFFAOYSA-N 3-[4-amino-7-(2-methylpyrazol-3-yl)-2-(pyridin-2-ylmethyl)triazolo[4,5-c]pyridin-6-yl]-2-fluorobenzonitrile Chemical compound N1=C(C=2C(C(=C1C1=C(F)C(C#N)=CC=C1)C1=CC=NN1C)=NN(N=2)CC1=CC=CC=N1)N WDIMPXNTABEEDG-UHFFFAOYSA-N 0.000 claims description 2
- MNUAACPKOCGMKO-UHFFFAOYSA-N 3-[5-amino-2-(pyridin-2-ylmethyl)-8-pyrimidin-4-yl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1)C1=NC=NC=C1)C=1C=C(C#N)C=CC=1 MNUAACPKOCGMKO-UHFFFAOYSA-N 0.000 claims description 2
- USUJGMZEOPRMRJ-UHFFFAOYSA-N 3-[5-amino-2-[(2,6-difluorophenyl)-hydroxymethyl]-8-pyrimidin-4-yl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound NC1=NC(C2=CC=CC(=C2)C#N)=C(C2=NC(=NN12)C(O)C1=C(F)C=CC=C1F)C1=CC=NC=N1 USUJGMZEOPRMRJ-UHFFFAOYSA-N 0.000 claims description 2
- PSIZASRGFVKTTQ-UHFFFAOYSA-N 3-[5-amino-2-[(2,6-difluorophenyl)-hydroxymethyl]-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]-2-fluorobenzonitrile Chemical compound NC1=NC(=CC=2N1N=C(N=2)C(O)C1=C(C=CC=C1F)F)C=1C(=C(C#N)C=CC=1)F PSIZASRGFVKTTQ-UHFFFAOYSA-N 0.000 claims description 2
- MWOOCFNLLDAOEV-UHFFFAOYSA-N 3-[5-amino-2-[(3-methylpyridin-2-yl)methoxy]-8-pyrimidin-4-yl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound NC1=NC(=C(C=2N1N=C(N=2)OCC1=NC=CC=C1C)C1=NC=NC=C1)C=1C=C(C#N)C=CC=1 MWOOCFNLLDAOEV-UHFFFAOYSA-N 0.000 claims description 2
- MJPCKFUORQJIKT-UHFFFAOYSA-N 3-[5-amino-2-[(5-pyrazol-1-yltetrazol-1-yl)methyl]-8-pyrimidin-4-yl-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound N1(N=CC=C1)C1=NN=NN1CC1=NN2C(=NC(=C(C2=N1)C1=NC=NC=C1)C=1C=C(C#N)C=CC=1)N MJPCKFUORQJIKT-UHFFFAOYSA-N 0.000 claims description 2
- FYICDFUJPPPZCX-UHFFFAOYSA-N 3-[5-amino-2-[[2-fluoro-6-[[(1-methyl-2-oxopyrrolidin-3-yl)amino]methyl]phenyl]-hydroxymethyl]-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]-2-fluorobenzonitrile Chemical compound NC1=NC(=CC=2N1N=C(N=2)C(O)C1=C(C=CC=C1CNC1C(N(CC1)C)=O)F)C=1C(=C(C#N)C=CC=1)F FYICDFUJPPPZCX-UHFFFAOYSA-N 0.000 claims description 2
- XAVOVGDLJRYSDJ-UHFFFAOYSA-N 3-[5-amino-2-[hydroxy(phenyl)methyl]-[1,2,4]triazolo[1,5-c]pyrimidin-7-yl]benzonitrile Chemical compound NC1=NC(=CC=2N1N=C(N=2)C(C1=CC=CC=C1)O)C=1C=C(C#N)C=CC=1 XAVOVGDLJRYSDJ-UHFFFAOYSA-N 0.000 claims description 2
- PLZPCHXKFQBBGL-UHFFFAOYSA-N 3-[8-amino-2-[(2,6-difluorophenyl)-hydroxymethyl]-5-(2,6-dimethylpyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]benzonitrile Chemical compound FC1=C(C(C=2N=C3C(=NC(C4=CC(C#N)=CC=C4)=C(N3N=2)C2=CC(C)=NC(=C2)C)N)O)C(F)=CC=C1 PLZPCHXKFQBBGL-UHFFFAOYSA-N 0.000 claims description 2
- UDHRZPXDBKETGI-UHFFFAOYSA-N 3-[8-amino-2-[(2,6-difluorophenyl)-hydroxymethyl]-5-pyrimidin-4-yl-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]benzonitrile Chemical compound FC1=C(C(C=2N=C3C(=NC(C4=CC(C#N)=CC=C4)=C(N3N=2)C2=CC=NC=N2)N)O)C(F)=CC=C1 UDHRZPXDBKETGI-UHFFFAOYSA-N 0.000 claims description 2
- KZAQSNJJLYBWHO-UHFFFAOYSA-N 3-[8-amino-2-[amino-(2,6-difluorophenyl)methyl]-5-(4-methyl-1,3-oxazol-5-yl)-[1,2,4]triazolo[1,5-a]pyrazin-6-yl]benzonitrile Chemical compound NC=1C=2N(C(=C(N=1)C=1C=C(C#N)C=CC=1)C1=C(N=CO1)C)N=C(N=2)C(C1=C(C=CC=C1F)F)N KZAQSNJJLYBWHO-UHFFFAOYSA-N 0.000 claims description 2
- VLLMDXWWQMNKSI-UHFFFAOYSA-N 5-amino-7-(3-cyano-2-fluorophenyl)-2-[(2,6-difluorophenyl)-hydroxymethyl]-[1,2,4]triazolo[1,5-c]pyrimidine-8-carbonitrile Chemical compound NC1=NC(=C(C=2N1N=C(N=2)C(O)C1=C(C=CC=C1F)F)C#N)C1=C(C(=CC=C1)C#N)F VLLMDXWWQMNKSI-UHFFFAOYSA-N 0.000 claims description 2
- NCWQLHHDGDXIJN-UHFFFAOYSA-N 6-(2-chloro-6-methylpyridin-4-yl)-5-(4-fluorophenyl)-1,2,4-triazin-3-amine Chemical compound ClC1=NC(C)=CC(C=2C(=NC(N)=NN=2)C=2C=CC(F)=CC=2)=C1 NCWQLHHDGDXIJN-UHFFFAOYSA-N 0.000 claims description 2
- KURQKNMKCGYWRJ-HNNXBMFYSA-N 7-(5-methylfuran-2-yl)-3-[[6-[[(3s)-oxolan-3-yl]oxymethyl]pyridin-2-yl]methyl]triazolo[4,5-d]pyrimidin-5-amine Chemical compound O1C(C)=CC=C1C1=NC(N)=NC2=C1N=NN2CC1=CC=CC(CO[C@@H]2COCC2)=N1 KURQKNMKCGYWRJ-HNNXBMFYSA-N 0.000 claims description 2
- 206010005003 Bladder cancer Diseases 0.000 claims description 2
- 239000002126 C01EB10 - Adenosine Substances 0.000 claims description 2
- 206010009944 Colon cancer Diseases 0.000 claims description 2
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 2
- 206010033128 Ovarian cancer Diseases 0.000 claims description 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 2
- 208000006265 Renal cell carcinoma Diseases 0.000 claims description 2
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 2
- 229960005305 adenosine Drugs 0.000 claims description 2
- 201000010536 head and neck cancer Diseases 0.000 claims description 2
- 208000014829 head and neck neoplasm Diseases 0.000 claims description 2
- QYCCLUSYHJXDEX-RWYGWLOXSA-N inupadenant Chemical compound C[S@](=O)CCOc1cc(N2CCN(CCn3c4nc(N)n5nc(nc5c4sc3=O)-c3ccco3)CC2)c(F)cc1F QYCCLUSYHJXDEX-RWYGWLOXSA-N 0.000 claims description 2
- 201000007270 liver cancer Diseases 0.000 claims description 2
- 208000014018 liver neoplasm Diseases 0.000 claims description 2
- 201000005202 lung cancer Diseases 0.000 claims description 2
- 208000020816 lung neoplasm Diseases 0.000 claims description 2
- 201000001441 melanoma Diseases 0.000 claims description 2
- 208000015347 renal cell adenocarcinoma Diseases 0.000 claims description 2
- ATFXVNUWQOXRRU-UHFFFAOYSA-N taminadenant Chemical compound BrC=1C(N)=NC(N2N=CC=C2)=NC=1N1C=CC=N1 ATFXVNUWQOXRRU-UHFFFAOYSA-N 0.000 claims description 2
- 201000005112 urinary bladder cancer Diseases 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 11
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 9
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 102100022464 5'-nucleotidase Human genes 0.000 claims 1
- 229940000425 combination drug Drugs 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 238000000034 method Methods 0.000 description 56
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US202062956840P | 2020-01-03 | 2020-01-03 | |
| US62/956,840 | 2020-01-03 | ||
| PCT/US2020/067576 WO2021138498A1 (en) | 2020-01-03 | 2020-12-30 | Cd73 inhibitor and a2a/a2b adenosine receptor inhibitor combination therapy |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2023509442A JP2023509442A (ja) | 2023-03-08 |
| JP2023509442A5 JP2023509442A5 (https=) | 2024-01-10 |
| JPWO2021138498A5 true JPWO2021138498A5 (https=) | 2024-01-10 |
Family
ID=74236306
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022540916A Pending JP2023509442A (ja) | 2020-01-03 | 2020-12-30 | Ｃｄ７３阻害剤とａ２ａ／ａ２ｂアデノシン受容体阻害剤の併用療法 |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US12060433B2 (https=) |
| EP (1) | EP4084870A1 (https=) |
| JP (1) | JP2023509442A (https=) |
| KR (1) | KR20220137013A (https=) |
| CN (1) | CN115551595A (https=) |
| AU (1) | AU2020419293A1 (https=) |
| CA (1) | CA3166536A1 (https=) |
| CL (2) | CL2022001795A1 (https=) |
| IL (1) | IL294437A (https=) |
| MX (1) | MX2022007573A (https=) |
| PH (1) | PH12022551621A1 (https=) |
| TW (1) | TW202135823A (https=) |
| WO (1) | WO2021138498A1 (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020185859A1 (en) | 2019-03-12 | 2020-09-17 | Arcus Biosciences, Inc. | Treatment of oncogene-driven cancers |
| US12310965B2 (en) | 2019-03-29 | 2025-05-27 | Arcus Biosciences, Inc. | Treatment of cancer utilizing an identified adenosine fingerprint |
| CA3166536A1 (en) | 2020-01-03 | 2021-07-08 | Incyte Corporation | Cd73 inhibitor and a2a/a2b adenosine receptor inhibitor combination therapy |
| WO2021138467A1 (en) | 2020-01-03 | 2021-07-08 | Incyte Corporation | Anti-cd73 antibodies and uses thereof |
| WO2021247188A1 (en) * | 2020-06-05 | 2021-12-09 | Bristol-Myers Squibb Company | Cd73 antagonist potency assay and methods of use thereof |
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| US4399216A (en) | 1980-02-25 | 1983-08-16 | The Trustees Of Columbia University | Processes for inserting DNA into eucaryotic cells and for producing proteinaceous materials |
| US4634665A (en) | 1980-02-25 | 1987-01-06 | The Trustees Of Columbia University In The City Of New York | Processes for inserting DNA into eucaryotic cells and for producing proteinaceous materials |
| US5156840A (en) | 1982-03-09 | 1992-10-20 | Cytogen Corporation | Amine-containing porphyrin derivatives |
| US5057313A (en) | 1986-02-25 | 1991-10-15 | The Center For Molecular Medicine And Immunology | Diagnostic and therapeutic antibody conjugates |
| DE3920358A1 (de) | 1989-06-22 | 1991-01-17 | Behringwerke Ag | Bispezifische und oligospezifische, mono- und oligovalente antikoerperkonstrukte, ihre herstellung und verwendung |
| DE69232137T2 (de) | 1991-11-25 | 2002-05-29 | Enzon Inc | Multivalente antigen-bindende proteine |
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2020
- 2020-12-30 CA CA3166536A patent/CA3166536A1/en active Pending
- 2020-12-30 US US17/138,306 patent/US12060433B2/en active Active
- 2020-12-30 EP EP20845756.4A patent/EP4084870A1/en not_active Withdrawn
- 2020-12-30 AU AU2020419293A patent/AU2020419293A1/en active Pending
- 2020-12-30 IL IL294437A patent/IL294437A/en unknown
- 2020-12-30 WO PCT/US2020/067576 patent/WO2021138498A1/en not_active Ceased
- 2020-12-30 TW TW109146858A patent/TW202135823A/zh unknown
- 2020-12-30 JP JP2022540916A patent/JP2023509442A/ja active Pending
- 2020-12-30 PH PH1/2022/551621A patent/PH12022551621A1/en unknown
- 2020-12-30 KR KR1020227026716A patent/KR20220137013A/ko not_active Withdrawn
- 2020-12-30 MX MX2022007573A patent/MX2022007573A/es unknown
- 2020-12-30 CN CN202080097404.0A patent/CN115551595A/zh active Pending
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2022
- 2022-06-30 CL CL2022001795A patent/CL2022001795A1/es unknown
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2024
- 2024-04-30 CL CL2024001326A patent/CL2024001326A1/es unknown
- 2024-07-10 US US18/768,783 patent/US20250059293A1/en active Pending
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