JPWO2021102288A5 - - Google Patents
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- JPWO2021102288A5 JPWO2021102288A5 JP2022529544A JP2022529544A JPWO2021102288A5 JP WO2021102288 A5 JPWO2021102288 A5 JP WO2021102288A5 JP 2022529544 A JP2022529544 A JP 2022529544A JP 2022529544 A JP2022529544 A JP 2022529544A JP WO2021102288 A5 JPWO2021102288 A5 JP WO2021102288A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrido
- pyridin
- pyrimidin
- trifluoromethyl
- hydroxypropan
- 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.)
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- QMOPAFMMLWUTKI-UHFFFAOYSA-N 1h-pyrido[3,4-d]pyrimidin-4-one Chemical compound N1=CC=C2C(O)=NC=NC2=C1 QMOPAFMMLWUTKI-UHFFFAOYSA-N 0.000 claims description 151
- 150000003839 salts Chemical class 0.000 claims description 59
- 150000001875 compounds Chemical class 0.000 claims description 53
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims description 35
- 238000011374 additional therapy Methods 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 206010028980 Neoplasm Diseases 0.000 claims description 22
- 239000003112 inhibitor Substances 0.000 claims description 22
- 201000011510 cancer Diseases 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 19
- -1 isothiazoyl Chemical group 0.000 claims description 19
- 230000011664 signaling Effects 0.000 claims description 18
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 16
- 125000001475 halogen functional group Chemical group 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims description 15
- 201000010099 disease Diseases 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 125000001188 haloalkyl group Chemical group 0.000 claims description 14
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 14
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 14
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 230000001404 mediated effect Effects 0.000 claims description 13
- 208000000102 Squamous Cell Carcinoma of Head and Neck Diseases 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 150000002431 hydrogen Chemical group 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 9
- 230000037361 pathway Effects 0.000 claims description 9
- 206010006187 Breast cancer Diseases 0.000 claims description 8
- 208000026310 Breast neoplasm Diseases 0.000 claims description 8
- 108010021064 CTLA-4 Antigen Proteins 0.000 claims description 8
- 102100039498 Cytotoxic T-lymphocyte protein 4 Human genes 0.000 claims description 8
- 101000666896 Homo sapiens V-type immunoglobulin domain-containing suppressor of T-cell activation Proteins 0.000 claims description 8
- 102100038282 V-type immunoglobulin domain-containing suppressor of T-cell activation Human genes 0.000 claims description 8
- 201000000459 head and neck squamous cell carcinoma Diseases 0.000 claims description 8
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 8
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 8
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 101001137987 Homo sapiens Lymphocyte activation gene 3 protein Proteins 0.000 claims description 7
- 102100020862 Lymphocyte activation gene 3 protein Human genes 0.000 claims description 7
- 108010074708 B7-H1 Antigen Proteins 0.000 claims description 6
- 229940045513 CTLA4 antagonist Drugs 0.000 claims description 6
- 206010009944 Colon cancer Diseases 0.000 claims description 6
- 102100024216 Programmed cell death 1 ligand 1 Human genes 0.000 claims description 6
- 206010060862 Prostate cancer Diseases 0.000 claims description 6
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 6
- 208000006265 Renal cell carcinoma Diseases 0.000 claims description 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
- 230000001394 metastastic effect Effects 0.000 claims description 6
- 206010061289 metastatic neoplasm Diseases 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 206010044412 transitional cell carcinoma Diseases 0.000 claims description 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 229940076838 Immune checkpoint inhibitor Drugs 0.000 claims description 5
- 206010027476 Metastases Diseases 0.000 claims description 5
- 101100519207 Mus musculus Pdcd1 gene Proteins 0.000 claims description 5
- 230000001594 aberrant effect Effects 0.000 claims description 5
- 230000009702 cancer cell proliferation Effects 0.000 claims description 5
- 239000012274 immune-checkpoint protein inhibitor Substances 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 108060003951 Immunoglobulin Proteins 0.000 claims description 4
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 4
- 206010027480 Metastatic malignant melanoma Diseases 0.000 claims description 4
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 4
- 101710089372 Programmed cell death protein 1 Proteins 0.000 claims description 4
- 206010041067 Small cell lung cancer Diseases 0.000 claims description 4
- 208000005718 Stomach Neoplasms Diseases 0.000 claims description 4
- 210000001744 T-lymphocyte Anatomy 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 4
- 208000029742 colonic neoplasm Diseases 0.000 claims description 4
- 210000003236 esophagogastric junction Anatomy 0.000 claims description 4
- 206010017758 gastric cancer Diseases 0.000 claims description 4
- 208000005017 glioblastoma Diseases 0.000 claims description 4
- 102000018358 immunoglobulin Human genes 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 201000007270 liver cancer Diseases 0.000 claims description 4
- 208000014018 liver neoplasm Diseases 0.000 claims description 4
- 201000005202 lung cancer Diseases 0.000 claims description 4
- 208000020816 lung neoplasm Diseases 0.000 claims description 4
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 4
- 201000001441 melanoma Diseases 0.000 claims description 4
- 230000009401 metastasis Effects 0.000 claims description 4
- 208000021039 metastatic melanoma Diseases 0.000 claims description 4
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 4
- 201000002528 pancreatic cancer Diseases 0.000 claims description 4
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 4
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims description 4
- PAQYIEZTLSDLQO-UHFFFAOYSA-N pyrido[3,4-d]pyrimidine Chemical compound N1=CN=C2C=NC=CC2=C1 PAQYIEZTLSDLQO-UHFFFAOYSA-N 0.000 claims description 4
- 230000000306 recurrent effect Effects 0.000 claims description 4
- 208000000587 small cell lung carcinoma Diseases 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 201000011549 stomach cancer Diseases 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 4
- 208000023747 urothelial carcinoma Diseases 0.000 claims description 4
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- JYCPLOLTTJFQLT-NSHDSACASA-N OC[C@H](C)N1C=NC2=C(C1=O)C=C(N=C2C=1C=NN(C=1)C)C1=NC=C(C=C1)C(F)(F)F Chemical compound OC[C@H](C)N1C=NC2=C(C1=O)C=C(N=C2C=1C=NN(C=1)C)C1=NC=C(C=C1)C(F)(F)F JYCPLOLTTJFQLT-NSHDSACASA-N 0.000 claims description 3
- 230000004709 cell invasion Effects 0.000 claims description 3
- 201000010536 head and neck cancer Diseases 0.000 claims description 3
- 208000014829 head and neck neoplasm Diseases 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 210000004881 tumor cell Anatomy 0.000 claims description 3
- 102100023990 60S ribosomal protein L17 Human genes 0.000 claims description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
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- 208000003174 Brain Neoplasms Diseases 0.000 claims description 2
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CN111961034A (zh) * | 2019-05-20 | 2020-11-20 | 浙江同源康医药股份有限公司 | 用作ret激酶抑制剂的化合物及其应用 |
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