JPWO2020052631A5 - - Google Patents
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- Publication number
- JPWO2020052631A5 JPWO2020052631A5 JP2021513827A JP2021513827A JPWO2020052631A5 JP WO2020052631 A5 JPWO2020052631 A5 JP WO2020052631A5 JP 2021513827 A JP2021513827 A JP 2021513827A JP 2021513827 A JP2021513827 A JP 2021513827A JP WO2020052631 A5 JPWO2020052631 A5 JP WO2020052631A5
- Authority
- JP
- Japan
- Prior art keywords
- triazolo
- methyl
- amino
- alkyl
- pyrimidin
- 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 cyano, hydroxyl Chemical group 0.000 claims 147
- 125000000217 alkyl group Chemical group 0.000 claims 85
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 34
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 30
- 150000001875 compounds Chemical class 0.000 claims 26
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 24
- 125000004452 carbocyclyl group Chemical group 0.000 claims 23
- 125000000623 heterocyclic group Chemical group 0.000 claims 22
- 229910052736 halogen Inorganic materials 0.000 claims 19
- 150000002367 halogens Chemical group 0.000 claims 19
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 18
- 125000004438 haloalkoxy group Chemical group 0.000 claims 15
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 13
- KXDHJXZQYSOELW-UHFFFAOYSA-M carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 12
- 239000004202 carbamide Substances 0.000 claims 12
- 125000005236 alkanoylamino group Chemical group 0.000 claims 10
- 239000008194 pharmaceutical composition Substances 0.000 claims 9
- 125000002947 alkylene group Chemical group 0.000 claims 5
- 102000004965 antibodies Human genes 0.000 claims 5
- 108090001123 antibodies Proteins 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 102000009346 Adenosine receptors Human genes 0.000 claims 4
- 108050000203 Adenosine receptors Proteins 0.000 claims 4
- 239000002246 antineoplastic agent Substances 0.000 claims 4
- 201000011510 cancer Diseases 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 3
- 239000002955 immunomodulating agent Substances 0.000 claims 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 3
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 3
- 125000002950 monocyclic group Chemical group 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000011780 sodium chloride Substances 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- OIRDTQYFTABQOQ-GAWUUDPSSA-N 9-β-D-XYLOFURANOSYL-ADENINE Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@H](O)[C@H]1O OIRDTQYFTABQOQ-GAWUUDPSSA-N 0.000 claims 2
- OIRDTQYFTABQOQ-SXVXDFOESA-N Adenosine Natural products Nc1ncnc2c1ncn2[C@@H]3O[C@@H](CO)[C@H](O)[C@@H]3O OIRDTQYFTABQOQ-SXVXDFOESA-N 0.000 claims 2
- 208000006673 Asthma Diseases 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 239000002126 C01EB10 - Adenosine Substances 0.000 claims 2
- 206010007556 Cardiac failure acute Diseases 0.000 claims 2
- 206010007558 Cardiac failure chronic Diseases 0.000 claims 2
- 206010008120 Cerebral ischaemia Diseases 0.000 claims 2
- 206010057668 Cognitive disease Diseases 0.000 claims 2
- 206010010099 Combined immunodeficiency Diseases 0.000 claims 2
- 206010015037 Epilepsy Diseases 0.000 claims 2
- 208000004361 Obstructive Lung Disease Diseases 0.000 claims 2
- 206010061536 Parkinson's disease Diseases 0.000 claims 2
- 206010060862 Prostate cancer Diseases 0.000 claims 2
- 208000006265 Renal Cell Carcinoma Diseases 0.000 claims 2
- 241000580858 Simian-Human immunodeficiency virus Species 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 229960005305 adenosine Drugs 0.000 claims 2
- 201000006474 brain ischemia Diseases 0.000 claims 2
- 230000001684 chronic Effects 0.000 claims 2
- 201000002403 combined T cell and B cell immunodeficiency Diseases 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000005842 heteroatoms Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 claims 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 2
- 201000005244 lung non-small cell carcinoma Diseases 0.000 claims 2
- 125000003566 oxetanyl group Chemical group 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
- 125000005494 pyridonyl group Chemical group 0.000 claims 2
- 238000001959 radiotherapy Methods 0.000 claims 2
- ZROHGHOFXNOHSO-BNTLRKBRSA-L (1R,2R)-cyclohexane-1,2-diamine;oxalate;platinum(2+) Chemical compound [H][N]([C@@H]1CCCC[C@H]1[N]1([H])[H])([H])[Pt]11OC(=O)C(=O)O1 ZROHGHOFXNOHSO-BNTLRKBRSA-L 0.000 claims 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 claims 1
- AOJJSUZBOXZQNB-TZSSRYMLSA-N ADRIAMYCIN Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims 1
- 102100007290 CD274 Human genes 0.000 claims 1
- 101710012053 CD274 Proteins 0.000 claims 1
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N Docetaxel Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims 1
- 229960004679 Doxorubicin Drugs 0.000 claims 1
- VJJPUSNTGOMMGY-MRVIYFEKSA-N Etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 claims 1
- 229960005420 Etoposide Drugs 0.000 claims 1
- HPXVMQGCIJGOCF-UHFFFAOYSA-N FC1=CC=C(C=C1)C1=C(C=2N(C(=N1)N)N=C(N=2)CC=1N=C(SC=1)C)C=1C=CC=2N(C=1)C=CN=2 Chemical compound FC1=CC=C(C=C1)C1=C(C=2N(C(=N1)N)N=C(N=2)CC=1N=C(SC=1)C)C=1C=CC=2N(C=1)C=CN=2 HPXVMQGCIJGOCF-UHFFFAOYSA-N 0.000 claims 1
- RCINICONZNJXQF-MZXODVADSA-N Intaxel Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims 1
- 229960001156 Mitoxantrone Drugs 0.000 claims 1
- KKZJGLLVHKMTCM-UHFFFAOYSA-N Mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 claims 1
- LWYDAAASGGAOQH-UHFFFAOYSA-N NC1=NC(=C(C=2N1N=C(N=2)CC1=C(C=CC=C1F)F)C1=CC(=NC(=C1)C)C#N)C=1OC=CN=1 Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=C(C=CC=C1F)F)C1=CC(=NC(=C1)C)C#N)C=1OC=CN=1 LWYDAAASGGAOQH-UHFFFAOYSA-N 0.000 claims 1
- BJCXOFQLGPZNJF-UHFFFAOYSA-N NC1=NC(=C(C=2N1N=C(N=2)CC1=C(C=CC=C1F)F)C=1C=CC(N(C=1)C)=O)C1=NC=CC=C1 Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=C(C=CC=C1F)F)C=1C=CC(N(C=1)C)=O)C1=NC=CC=C1 BJCXOFQLGPZNJF-UHFFFAOYSA-N 0.000 claims 1
- FYGUOAMXRGGXGR-UHFFFAOYSA-N NC1=NC(=C(C=2N1N=C(N=2)CC1=C(C=CC=C1F)F)C=1C=CC(N(C=1)C)=O)C=1C=NC(=CC=1)C Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=C(C=CC=C1F)F)C=1C=CC(N(C=1)C)=O)C=1C=NC(=CC=1)C FYGUOAMXRGGXGR-UHFFFAOYSA-N 0.000 claims 1
- XGANDSJRULUAJD-UHFFFAOYSA-N NC1=NC(=C(C=2N1N=C(N=2)CC1=C(C=CC=C1F)F)C=1C=CC(N(C=1)C)=O)Cl Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=C(C=CC=C1F)F)C=1C=CC(N(C=1)C)=O)Cl XGANDSJRULUAJD-UHFFFAOYSA-N 0.000 claims 1
- NOYVLVDEKLNKFK-UHFFFAOYSA-N NC1=NC(=C(C=2N1N=C(N=2)CC1=C(C=CC=C1F)F)C=1C=CC(N(C=1)C)=O)N1N=CC=N1 Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=C(C=CC=C1F)F)C=1C=CC(N(C=1)C)=O)N1N=CC=N1 NOYVLVDEKLNKFK-UHFFFAOYSA-N 0.000 claims 1
- OGILCXDJHLQZTN-UHFFFAOYSA-N NC1=NC(=C(C=2N1N=C(N=2)CC1=CC=CC(=N1)N)C=1C=CC=2N(C=1)C=CN=2)C1=CC=C(C=C1)F Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=CC=CC(=N1)N)C=1C=CC=2N(C=1)C=CN=2)C1=CC=C(C=C1)F OGILCXDJHLQZTN-UHFFFAOYSA-N 0.000 claims 1
- DRWXKQJJYFKKOA-UHFFFAOYSA-N NC1=NC(=C(C=2N1N=C(N=2)CC1=NC(=CC=C1)N)C=1C=CC(N(C=1)C)=O)C1=CC=C(C=C1)F Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC(=CC=C1)N)C=1C=CC(N(C=1)C)=O)C1=CC=C(C=C1)F DRWXKQJJYFKKOA-UHFFFAOYSA-N 0.000 claims 1
- UFJDURNDZGLRES-UHFFFAOYSA-N NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C1=CN(C(C=C1)=O)C)C1=CC=C(C#N)C=C1 Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C1=CN(C(C=C1)=O)C)C1=CC=C(C#N)C=C1 UFJDURNDZGLRES-UHFFFAOYSA-N 0.000 claims 1
- YIDWZRRYJRXRPX-UHFFFAOYSA-N NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C=1C=CC(N(C=1)C(C)C)=O)C1=CC=C(C=C1)F Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C=1C=CC(N(C=1)C(C)C)=O)C1=CC=C(C=C1)F YIDWZRRYJRXRPX-UHFFFAOYSA-N 0.000 claims 1
- CUZJHUAIWPKQIM-UHFFFAOYSA-N NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C=1C=CC(N(C=1)C)=O)C1=CC(=C(C=C1)F)F Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C=1C=CC(N(C=1)C)=O)C1=CC(=C(C=C1)F)F CUZJHUAIWPKQIM-UHFFFAOYSA-N 0.000 claims 1
- ANVNFQJDCKBOSL-UHFFFAOYSA-N NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C=1C=CC(N(C=1)C)=O)C=1OC=CN=1 Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C=1C=CC(N(C=1)C)=O)C=1OC=CN=1 ANVNFQJDCKBOSL-UHFFFAOYSA-N 0.000 claims 1
- WWGWJTQBATTYLS-UHFFFAOYSA-N NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C=1C=CC(N(C=1)C)=O)N1N=CC=C1 Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C=1C=CC(N(C=1)C)=O)N1N=CC=C1 WWGWJTQBATTYLS-UHFFFAOYSA-N 0.000 claims 1
- BFFFIJSOBYMNPI-UHFFFAOYSA-N NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C=1C=CC(N(C=1)CC)=O)C1=CC=C(C=C1)F Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C=1C=CC(N(C=1)CC)=O)C1=CC=C(C=C1)F BFFFIJSOBYMNPI-UHFFFAOYSA-N 0.000 claims 1
- MGVORKOWNJZJCZ-SFHVURJKSA-N NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C=1C=CC(N(C=1)[C@@H]1COCC1)=O)C1=CC=C(C=C1)F Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1F)C=1C=CC(N(C=1)[C@@H]1COCC1)=O)C1=CC=C(C=C1)F MGVORKOWNJZJCZ-SFHVURJKSA-N 0.000 claims 1
- IVLZUGWDYRIRPP-UHFFFAOYSA-N NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1OC(F)F)C=1C=CC(N(C=1)C)=O)C1=CC=C(C=C1)F Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1OC(F)F)C=1C=CC(N(C=1)C)=O)C1=CC=C(C=C1)F IVLZUGWDYRIRPP-UHFFFAOYSA-N 0.000 claims 1
- HNQYRYXKHXZOGM-UHFFFAOYSA-N NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1OC(F)F)C=1C=CC(N(C=1)C)=O)C=1OC=CN=1 Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC1=NC=CC=C1OC(F)F)C=1C=CC(N(C=1)C)=O)C=1OC=CN=1 HNQYRYXKHXZOGM-UHFFFAOYSA-N 0.000 claims 1
- FAFWPWMKYLQUHT-UHFFFAOYSA-N NC1=NC(=C(C=2N1N=C(N=2)CC=1N=CSC=1)C=1C=CC(N(C=1)C)=O)C1=CC=C(C=C1)F Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC=1N=CSC=1)C=1C=CC(N(C=1)C)=O)C1=CC=C(C=C1)F FAFWPWMKYLQUHT-UHFFFAOYSA-N 0.000 claims 1
- DFXFMJLXQWVGCL-UHFFFAOYSA-N NC1=NC(=C(C=2N1N=C(N=2)CC=1SC=CN=1)C=1C=CC(N(C=1)C)=O)C1=CC=C(C=C1)F Chemical compound NC1=NC(=C(C=2N1N=C(N=2)CC=1SC=CN=1)C=1C=CC(N(C=1)C)=O)C1=CC=C(C=C1)F DFXFMJLXQWVGCL-UHFFFAOYSA-N 0.000 claims 1
- 229960001592 Paclitaxel Drugs 0.000 claims 1
- 238000002512 chemotherapy Methods 0.000 claims 1
- 229960004316 cisplatin Drugs 0.000 claims 1
- 238000002648 combination therapy Methods 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 229960003668 docetaxel Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000006005 fluoroethoxy group Chemical group 0.000 claims 1
- 238000009169 immunotherapy Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 229960001756 oxaliplatin Drugs 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
- FVLAYJRLBLHIPV-UHFFFAOYSA-N pyrimidin-5-amine Chemical compound NC1=CN=CN=C1 FVLAYJRLBLHIPV-UHFFFAOYSA-N 0.000 claims 1
- 229930003347 taxol Natural products 0.000 claims 1
- LXZZYRPGZAFOLE-UHFFFAOYSA-L transplatin Chemical compound [H][N]([H])([H])[Pt](Cl)(Cl)[N]([H])([H])[H] LXZZYRPGZAFOLE-UHFFFAOYSA-L 0.000 claims 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2024096058A JP2024123079A (ja) | 2018-09-12 | 2024-06-13 | トリアゾロ－ピリミジン化合物およびそれらの使用 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2018105220 | 2018-09-12 | ||
| CNPCT/CN2018/105220 | 2018-09-12 | ||
| PCT/CN2019/105591 WO2020052631A1 (en) | 2018-09-12 | 2019-09-12 | Triazolo-pyrimidine compounds and uses thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2024096058A Division JP2024123079A (ja) | 2018-09-12 | 2024-06-13 | トリアゾロ－ピリミジン化合物およびそれらの使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2022500402A JP2022500402A (ja) | 2022-01-04 |
| JPWO2020052631A5 true JPWO2020052631A5 (ru) | 2022-09-05 |
| JP7572353B2 JP7572353B2 (ja) | 2024-10-23 |
Family
ID=
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