JPWO2019196803A5 - - Google Patents
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- Publication number
- JPWO2019196803A5 JPWO2019196803A5 JP2020554834A JP2020554834A JPWO2019196803A5 JP WO2019196803 A5 JPWO2019196803 A5 JP WO2019196803A5 JP 2020554834 A JP2020554834 A JP 2020554834A JP 2020554834 A JP2020554834 A JP 2020554834A JP WO2019196803 A5 JPWO2019196803 A5 JP WO2019196803A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- triazolo
- pyrazolo
- fran
- pyrimidine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- -1 halo C 2-6 alkenyl Chemical group 0.000 claims 167
- 125000000217 alkyl group Chemical group 0.000 claims 48
- 125000003118 aryl group Chemical group 0.000 claims 27
- 125000000623 heterocyclic group Chemical group 0.000 claims 25
- 125000001072 heteroaryl group Chemical group 0.000 claims 22
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 17
- 150000001875 compounds Chemical class 0.000 claims 16
- 125000003545 alkoxy group Chemical group 0.000 claims 14
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- 239000001257 hydrogen Substances 0.000 claims 14
- 125000005843 halogen group Chemical group 0.000 claims 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 10
- 125000001424 substituent group Chemical group 0.000 claims 10
- LKJPYSCBVHEWIU-UHFFFAOYSA-N N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CS(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-UHFFFAOYSA-N 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 9
- 150000002431 hydrogen Chemical class 0.000 claims 9
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 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 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000004043 oxo group Chemical group O=* 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 150000001345 alkine derivatives Chemical class 0.000 claims 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 2
- SSJXIUAHEKJCMH-WDSKDSINSA-N (1s,2s)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@@H]1N SSJXIUAHEKJCMH-WDSKDSINSA-N 0.000 claims 1
- 125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- ZBAPDJVZIIDRHT-UHFFFAOYSA-N 2-[7-amino-4-(1,3-thiazol-2-yl)-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-10-yl]-N-[(3-hydroxyoxetan-3-yl)methyl]-2-phenylpropanamide Chemical compound NC1=NC2=C(C=3N1N=C(N=3)C=1SC=CN=1)C=NN2C(C(=O)NCC1(COC1)O)(C)C1=CC=CC=C1 ZBAPDJVZIIDRHT-UHFFFAOYSA-N 0.000 claims 1
- AQFNHHRDYSWEKY-UHFFFAOYSA-N 2-[7-amino-4-(furan-2-yl)-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-10-yl]-2-phenyl-N-(2-phenylethyl)acetamide Chemical compound NC1=NC2=C(C=3N1N=C(N=3)C=1OC=CC=1)C=NN2C(C(=O)NCCC1=CC=CC=C1)C1=CC=CC=C1 AQFNHHRDYSWEKY-UHFFFAOYSA-N 0.000 claims 1
- BONIDAWVCJWJDB-UHFFFAOYSA-N 2-[7-amino-4-(furan-2-yl)-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-10-yl]-2-phenyl-N-(2-phenylethyl)propanamide Chemical compound NC1=NC2=C(C=3N1N=C(N=3)C=1OC=CC=1)C=NN2C(C(=O)NCCC1=CC=CC=C1)(C)C1=CC=CC=C1 BONIDAWVCJWJDB-UHFFFAOYSA-N 0.000 claims 1
- OIIPCMUTZHNMPV-UHFFFAOYSA-N 2-[7-amino-4-(furan-2-yl)-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-10-yl]-2-phenylacetamide Chemical compound NC1=NC2=C(C=3N1N=C(N=3)C=1OC=CC=1)C=NN2C(C(=O)N)C1=CC=CC=C1 OIIPCMUTZHNMPV-UHFFFAOYSA-N 0.000 claims 1
- JXNYSHOLJKILEJ-UHFFFAOYSA-N 2-[7-amino-4-(furan-2-yl)-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-10-yl]-N,2-diphenylacetamide Chemical compound NC1=NC2=C(C=3N1N=C(N=3)C=1OC=CC=1)C=NN2C(C(=O)NC1=CC=CC=C1)C1=CC=CC=C1 JXNYSHOLJKILEJ-UHFFFAOYSA-N 0.000 claims 1
- ZRUMFTBPYKFPDG-UHFFFAOYSA-N 2-[7-amino-4-(furan-2-yl)-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-10-yl]-N,2-diphenylpropanamide Chemical compound NC1=NC2=C(C=3N1N=C(N=3)C=1OC=CC=1)C=NN2C(C(=O)NC1=CC=CC=C1)(C)C1=CC=CC=C1 ZRUMFTBPYKFPDG-UHFFFAOYSA-N 0.000 claims 1
- CYDDABGUYDMNQV-UHFFFAOYSA-N 2-[7-amino-4-(furan-2-yl)-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-10-yl]-N-[(3-hydroxyoxetan-3-yl)methyl]-2-methyl-3-phenylpropanamide Chemical compound NC1=NC2=C(C=3N1N=C(N=3)C=1OC=CC=1)C=NN2C(C(=O)NCC1(COC1)O)(CC1=CC=CC=C1)C CYDDABGUYDMNQV-UHFFFAOYSA-N 0.000 claims 1
- HFPORDHLSPFKGH-UHFFFAOYSA-N 2-[7-amino-4-(furan-2-yl)-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-10-yl]-N-[2-(oxolan-3-yl)ethyl]-2-phenylpropanamide Chemical compound NC1=NC2=C(C=3N1N=C(N=3)C=1OC=CC=1)C=NN2C(C(=O)NCCC1COCC1)(C)C1=CC=CC=C1 HFPORDHLSPFKGH-UHFFFAOYSA-N 0.000 claims 1
- NESYUEDPVLLQNE-YAOANENCSA-N 2-[7-amino-4-(furan-2-yl)-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-10-yl]-N-[[(2R)-oxolan-2-yl]methyl]-2-phenylpropanamide Chemical compound NC1=NC2=C(C=3N1N=C(N3)C=3OC=CC3)C=NN2C(C(=O)NC[C@@H]2OCCC2)(C)C2=CC=CC=C2 NESYUEDPVLLQNE-YAOANENCSA-N 0.000 claims 1
- NESYUEDPVLLQNE-FXIRQEPWSA-N 2-[7-amino-4-(furan-2-yl)-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-10-yl]-N-[[(2S)-oxolan-2-yl]methyl]-2-phenylpropanamide Chemical compound NC1=NC2=C(C=3N1N=C(N3)C=3OC=CC3)C=NN2C(C(=O)NC[C@H]2OCCC2)(C)C2=CC=CC=C2 NESYUEDPVLLQNE-FXIRQEPWSA-N 0.000 claims 1
- BWHFVISERUZKFX-GZAIGYLVSA-N 2-[7-amino-4-(furan-2-yl)-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-10-yl]-N-[[(3R)-oxolan-3-yl]methyl]-2-phenylpropanamide Chemical compound NC1=NC2=C(C=3N1N=C(N3)C=3OC=CC3)C=NN2C(C(=O)NC[C@@H]2COCC2)(C)C2=CC=CC=C2 BWHFVISERUZKFX-GZAIGYLVSA-N 0.000 claims 1
- BWHFVISERUZKFX-FZADBTJQSA-N 2-[7-amino-4-(furan-2-yl)-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-10-yl]-N-[[(3S)-oxolan-3-yl]methyl]-2-phenylpropanamide Chemical compound NC1=NC2=C(C=3N1N=C(N3)C=3OC=CC3)C=NN2C(C(=O)NC[C@H]2COCC2)(C)C2=CC=CC=C2 BWHFVISERUZKFX-FZADBTJQSA-N 0.000 claims 1
- AYSOKIZRHXAXKZ-UHFFFAOYSA-N 2-[7-amino-4-(furan-2-yl)-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-10-yl]-N-benzyl-2-phenylpropanamide Chemical compound NC1=NC2=C(C=3N1N=C(N=3)C=1OC=CC=1)C=NN2C(C(=O)NCC1=CC=CC=C1)(C)C1=CC=CC=C1 AYSOKIZRHXAXKZ-UHFFFAOYSA-N 0.000 claims 1
- SULAKTSGGJDGHW-UHFFFAOYSA-N 2-[7-amino-4-(furan-2-yl)-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-10-yl]-N-cyclohexyl-2-phenylacetamide Chemical compound NC1=NC2=C(C=3N1N=C(N=3)C=1OC=CC=1)C=NN2C(C(=O)NC1CCCCC1)C1=CC=CC=C1 SULAKTSGGJDGHW-UHFFFAOYSA-N 0.000 claims 1
- QQAUQAWRDINYAJ-UHFFFAOYSA-N 2-[7-amino-4-(furan-2-yl)-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-10-yl]-N-cyclohexyl-2-phenylpropanamide Chemical compound NC1=NC2=C(C=3N1N=C(N=3)C=1OC=CC=1)C=NN2C(C(=O)NC1CCCCC1)(C)C1=CC=CC=C1 QQAUQAWRDINYAJ-UHFFFAOYSA-N 0.000 claims 1
- FYZLMNWUILTTOX-UHFFFAOYSA-N 2-[7-amino-4-(furan-2-yl)-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-10-yl]-N-cyclopentyl-2-phenylacetamide Chemical compound NC1=NC2=C(C=3N1N=C(N=3)C=1OC=CC=1)C=NN2C(C(=O)NC1CCCC1)C1=CC=CC=C1 FYZLMNWUILTTOX-UHFFFAOYSA-N 0.000 claims 1
- VLFARNGBVYBZCP-UHFFFAOYSA-N 2-[7-amino-4-(furan-2-yl)-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-10-yl]-N-ethyl-2-phenylacetamide Chemical compound NC1=NC2=C(C=3N1N=C(N=3)C=1OC=CC=1)C=NN2C(C(=O)NCC)C1=CC=CC=C1 VLFARNGBVYBZCP-UHFFFAOYSA-N 0.000 claims 1
- YPLCTRRGZGFGAI-UHFFFAOYSA-N 2-[7-amino-4-(furan-2-yl)-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-10-yl]-N-methyl-2-phenylacetamide Chemical compound NC1=NC2=C(C=3N1N=C(N=3)C=1OC=CC=1)C=NN2C(C(=O)NC)C1=CC=CC=C1 YPLCTRRGZGFGAI-UHFFFAOYSA-N 0.000 claims 1
- SCJTYFMIPAVYKX-UHFFFAOYSA-N 2-[7-amino-4-(furan-2-yl)-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaen-10-yl]-N-methyl-2-phenylpropanamide Chemical compound NC1=NC2=C(C=3N1N=C(N=3)C=1OC=CC=1)C=NN2C(C(=O)NC)(C)C1=CC=CC=C1 SCJTYFMIPAVYKX-UHFFFAOYSA-N 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
- YYLLIJHXUHJATK-UHFFFAOYSA-N Cyclohexyl acetate Chemical compound CC(=O)OC1CCCCC1 YYLLIJHXUHJATK-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 230000004927 fusion Effects 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- JBFAQRBRZBMFKY-UHFFFAOYSA-N n-[[4-(trifluoromethyl)phenyl]methyl]acetamide Chemical compound CC(=O)NCC1=CC=C(C(F)(F)F)C=C1 JBFAQRBRZBMFKY-UHFFFAOYSA-N 0.000 claims 1
- 125000003566 oxetanyl group Chemical group 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNPCT/CN2018/082140 | 2018-04-08 | ||
| CN2018082140 | 2018-04-08 | ||
| PCT/CN2019/081785 WO2019196803A1 (en) | 2018-04-08 | 2019-04-08 | Pyrazolotriazolopyrimidine derivatives as a2a receptor antagonist |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2021520392A JP2021520392A (ja) | 2021-08-19 |
| JP2021520392A5 JP2021520392A5 (https=) | 2022-04-07 |
| JPWO2019196803A5 true JPWO2019196803A5 (https=) | 2022-04-07 |
Family
ID=68163465
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020554834A Withdrawn JP2021520392A (ja) | 2018-04-08 | 2019-04-08 | Ａ２ａ受容体アンタゴニストとしてのピラゾロトリアゾロピリミジン誘導体 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US11472811B2 (https=) |
| EP (1) | EP3774813A4 (https=) |
| JP (1) | JP2021520392A (https=) |
| KR (1) | KR20200140849A (https=) |
| CN (1) | CN112313234B (https=) |
| AU (1) | AU2019251148A1 (https=) |
| BR (1) | BR112020020078A2 (https=) |
| CA (1) | CA3095839A1 (https=) |
| EA (1) | EA202092036A1 (https=) |
| IL (1) | IL277744A (https=) |
| MX (1) | MX2020010618A (https=) |
| SG (1) | SG11202009706VA (https=) |
| TW (1) | TW202010500A (https=) |
| WO (1) | WO2019196803A1 (https=) |
| ZA (1) | ZA202005772B (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2020010618A (es) | 2018-04-08 | 2020-11-12 | Beigene Ltd | Derivados de pirazolotriazolopiriminina como antagonista del receptor a2a. |
| CA3177057A1 (en) * | 2020-03-26 | 2021-09-30 | Astrazeneca Ab | Triazolone compounds |
| WO2021191376A1 (en) * | 2020-03-26 | 2021-09-30 | Astrazeneca Ab | Triazolone compounds |
| EP4214200A1 (en) | 2020-10-22 | 2023-07-26 | Nimmune Biopharma, Inc. | Lancl ligands |
| CN113773327B (zh) * | 2021-09-13 | 2022-07-15 | 八叶草健康产业研究院(厦门)有限公司 | 一种吡唑并嘧啶并三唑环类化合物的制备方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI1283839T1 (https=) * | 2000-05-26 | 2005-08-31 | Schering Corp | |
| AU2002347055B2 (en) | 2001-10-08 | 2006-10-12 | F. Hoffmann-La Roche Ag | Substituted Triazolopyridine Compounds |
| US20030139427A1 (en) | 2002-08-23 | 2003-07-24 | Osi Pharmaceuticals Inc. | Bicyclic pyrimidinyl derivatives and methods of use thereof |
| EP1745047B1 (en) | 2004-04-21 | 2010-03-24 | Schering Corporation | Pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine adenosine-a2a- receptor antagonists |
| CN103261202B (zh) * | 2010-09-24 | 2016-01-20 | 阿迪维纳斯疗法有限公司 | 作为腺苷受体拮抗剂的稠合三环化合物 |
| WO2012135084A1 (en) | 2011-03-31 | 2012-10-04 | Merck Sharp & Dohme Corp. | METABOLITES OF 2-(FURAN-2-YL)-7-(2-(4-(4-(2-METHOXYETHOXY)PHENYL)PIPERAZIN-1-YL)ETHYL)-7H-PYRAZOLO[4,3-e][1,2,4]TRIAZOLO[1,5-c]PYRIMIDIN-5-AMINE AND THEIR UTILITY AS ADENOSINE A2a RECEPTOR ANTAGONISTS |
| WO2017136375A1 (en) | 2016-02-05 | 2017-08-10 | Concert Pharmaceuticals, Inc. | Deuterated tozadenant |
| MX2020010618A (es) | 2018-04-08 | 2020-11-12 | Beigene Ltd | Derivados de pirazolotriazolopiriminina como antagonista del receptor a2a. |
| CN110742893B (zh) | 2018-07-23 | 2024-04-05 | 百济神州(北京)生物科技有限公司 | A2a受体拮抗剂治疗癌症的方法 |
-
2019
- 2019-04-08 MX MX2020010618A patent/MX2020010618A/es unknown
- 2019-04-08 CA CA3095839A patent/CA3095839A1/en active Pending
- 2019-04-08 KR KR1020207031434A patent/KR20200140849A/ko not_active Ceased
- 2019-04-08 AU AU2019251148A patent/AU2019251148A1/en not_active Abandoned
- 2019-04-08 EA EA202092036A patent/EA202092036A1/ru unknown
- 2019-04-08 WO PCT/CN2019/081785 patent/WO2019196803A1/en not_active Ceased
- 2019-04-08 TW TW108112189A patent/TW202010500A/zh unknown
- 2019-04-08 EP EP19785064.7A patent/EP3774813A4/en not_active Withdrawn
- 2019-04-08 SG SG11202009706VA patent/SG11202009706VA/en unknown
- 2019-04-08 JP JP2020554834A patent/JP2021520392A/ja not_active Withdrawn
- 2019-04-08 BR BR112020020078-6A patent/BR112020020078A2/pt not_active IP Right Cessation
- 2019-04-08 CN CN201980024422.3A patent/CN112313234B/zh not_active Expired - Fee Related
- 2019-04-08 US US16/982,681 patent/US11472811B2/en active Active
-
2020
- 2020-09-17 ZA ZA2020/05772A patent/ZA202005772B/en unknown
- 2020-10-01 IL IL277744A patent/IL277744A/en unknown
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