KR20210131371A - 1-(1-옥소-1,2-디하이드로이소퀴놀린-5-일)-5-(트리플루오로메틸)-n-(2-(트리플루오로메틸)피리딘-4-일)-1h-피라졸-4-카복사미드 일수화물의 결정질 형태 - Google Patents
1-(1-옥소-1,2-디하이드로이소퀴놀린-5-일)-5-(트리플루오로메틸)-n-(2-(트리플루오로메틸)피리딘-4-일)-1h-피라졸-4-카복사미드 일수화물의 결정질 형태 Download PDFInfo
- Publication number
- KR20210131371A KR20210131371A KR1020217029765A KR20217029765A KR20210131371A KR 20210131371 A KR20210131371 A KR 20210131371A KR 1020217029765 A KR1020217029765 A KR 1020217029765A KR 20217029765 A KR20217029765 A KR 20217029765A KR 20210131371 A KR20210131371 A KR 20210131371A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- crystalline form
- disease
- condition
- cancer
- 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.)
- Withdrawn
Links
- -1 pyrazole-4-carboxamide monohydrate Chemical compound 0.000 title claims abstract description 11
- 229940126062 Compound A Drugs 0.000 claims abstract description 124
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims abstract description 124
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 117
- 201000010099 disease Diseases 0.000 claims abstract description 59
- 239000000203 mixture Substances 0.000 claims abstract description 53
- 238000000034 method Methods 0.000 claims abstract description 48
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 11
- 102000057613 Mucosa-Associated Lymphoid Tissue Lymphoma Translocation 1 Human genes 0.000 claims abstract 4
- 108700026676 Mucosa-Associated Lymphoid Tissue Lymphoma Translocation 1 Proteins 0.000 claims abstract 4
- 150000004682 monohydrates Chemical class 0.000 claims description 78
- 208000035475 disorder Diseases 0.000 claims description 52
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 45
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 36
- 208000024891 symptom Diseases 0.000 claims description 34
- 239000002904 solvent Substances 0.000 claims description 33
- 206010028980 Neoplasm Diseases 0.000 claims description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 239000002244 precipitate Substances 0.000 claims description 16
- 239000012453 solvate Substances 0.000 claims description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 15
- 201000011510 cancer Diseases 0.000 claims description 15
- 230000005764 inhibitory process Effects 0.000 claims description 15
- 239000003085 diluting agent Substances 0.000 claims description 12
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 12
- 239000000725 suspension Substances 0.000 claims description 11
- 238000001757 thermogravimetry curve Methods 0.000 claims description 11
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 10
- 238000010992 reflux Methods 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 7
- 208000026278 immune system disease Diseases 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 4
- 238000001953 recrystallisation Methods 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 239000006188 syrup Substances 0.000 claims description 3
- 235000020357 syrup Nutrition 0.000 claims description 3
- 239000006186 oral dosage form Substances 0.000 claims description 2
- 101150113681 MALT1 gene Proteins 0.000 claims 3
- 238000002360 preparation method Methods 0.000 abstract description 9
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 abstract description 5
- 230000008569 process Effects 0.000 abstract description 3
- 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 description 40
- 206010012818 diffuse large B-cell lymphoma Diseases 0.000 description 40
- 208000025205 Mantle-Cell Lymphoma Diseases 0.000 description 36
- 201000003444 follicular lymphoma Diseases 0.000 description 36
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 description 30
- 206010025323 Lymphomas Diseases 0.000 description 29
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 29
- 208000032839 leukemia Diseases 0.000 description 26
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 description 21
- 210000003563 lymphoid tissue Anatomy 0.000 description 20
- 210000004027 cell Anatomy 0.000 description 18
- 206010009900 Colitis ulcerative Diseases 0.000 description 16
- 201000006704 Ulcerative Colitis Diseases 0.000 description 16
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 16
- 201000001263 Psoriatic Arthritis Diseases 0.000 description 13
- 208000036824 Psoriatic arthropathy Diseases 0.000 description 13
- 206010039073 rheumatoid arthritis Diseases 0.000 description 12
- 238000002411 thermogravimetry Methods 0.000 description 12
- 206010009944 Colon cancer Diseases 0.000 description 10
- 206010039491 Sarcoma Diseases 0.000 description 10
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 9
- 208000011231 Crohn disease Diseases 0.000 description 9
- 101000957807 Homo sapiens Mucosa-associated lymphoid tissue lymphoma translocation protein 1 Proteins 0.000 description 9
- 208000008839 Kidney Neoplasms Diseases 0.000 description 9
- 201000004681 Psoriasis Diseases 0.000 description 9
- 206010038389 Renal cancer Diseases 0.000 description 9
- 208000033559 Waldenström macroglobulinemia Diseases 0.000 description 9
- 208000006673 asthma Diseases 0.000 description 9
- 201000010982 kidney cancer Diseases 0.000 description 9
- 201000007924 marginal zone B-cell lymphoma Diseases 0.000 description 9
- 208000021937 marginal zone lymphoma Diseases 0.000 description 9
- 208000028564 B-cell non-Hodgkin lymphoma Diseases 0.000 description 8
- 102100038732 Mucosa-associated lymphoid tissue lymphoma translocation protein 1 Human genes 0.000 description 8
- 230000001404 mediated effect Effects 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000001179 sorption measurement Methods 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 7
- 208000016025 Waldenstroem macroglobulinemia Diseases 0.000 description 7
- 230000001154 acute effect Effects 0.000 description 7
- 230000011664 signaling Effects 0.000 description 7
- APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 description 6
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 description 6
- 208000017604 Hodgkin disease Diseases 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 208000036762 Acute promyelocytic leukaemia Diseases 0.000 description 5
- 206010005003 Bladder cancer Diseases 0.000 description 5
- 206010006187 Breast cancer Diseases 0.000 description 5
- 208000026310 Breast neoplasm Diseases 0.000 description 5
- 208000011691 Burkitt lymphomas Diseases 0.000 description 5
- 201000009030 Carcinoma Diseases 0.000 description 5
- 208000001333 Colorectal Neoplasms Diseases 0.000 description 5
- 206010014733 Endometrial cancer Diseases 0.000 description 5
- 206010014759 Endometrial neoplasm Diseases 0.000 description 5
- 208000031637 Erythroblastic Acute Leukemia Diseases 0.000 description 5
- 208000036566 Erythroleukaemia Diseases 0.000 description 5
- 208000006168 Ewing Sarcoma Diseases 0.000 description 5
- 208000032612 Glial tumor Diseases 0.000 description 5
- 206010018338 Glioma Diseases 0.000 description 5
- 208000021519 Hodgkin lymphoma Diseases 0.000 description 5
- 208000010747 Hodgkins lymphoma Diseases 0.000 description 5
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 5
- 229940122339 MALT1 inhibitor Drugs 0.000 description 5
- 208000000172 Medulloblastoma Diseases 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 208000003445 Mouth Neoplasms Diseases 0.000 description 5
- 208000034578 Multiple myelomas Diseases 0.000 description 5
- 206010033128 Ovarian cancer Diseases 0.000 description 5
- 206010061535 Ovarian neoplasm Diseases 0.000 description 5
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 5
- 206010035226 Plasma cell myeloma Diseases 0.000 description 5
- 208000007452 Plasmacytoma Diseases 0.000 description 5
- 206010060862 Prostate cancer Diseases 0.000 description 5
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 5
- 208000005718 Stomach Neoplasms Diseases 0.000 description 5
- 208000000389 T-cell leukemia Diseases 0.000 description 5
- 208000028530 T-cell lymphoblastic leukemia/lymphoma Diseases 0.000 description 5
- 206010042971 T-cell lymphoma Diseases 0.000 description 5
- 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 description 5
- 208000024313 Testicular Neoplasms Diseases 0.000 description 5
- 206010057644 Testis cancer Diseases 0.000 description 5
- 208000024770 Thyroid neoplasm Diseases 0.000 description 5
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 5
- 208000021841 acute erythroid leukemia Diseases 0.000 description 5
- 208000037833 acute lymphoblastic T-cell leukemia Diseases 0.000 description 5
- 210000004556 brain Anatomy 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 208000029742 colonic neoplasm Diseases 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 206010017758 gastric cancer Diseases 0.000 description 5
- 208000005017 glioblastoma Diseases 0.000 description 5
- 201000010536 head and neck cancer Diseases 0.000 description 5
- 208000014829 head and neck neoplasm Diseases 0.000 description 5
- 201000007270 liver cancer Diseases 0.000 description 5
- 208000014018 liver neoplasm Diseases 0.000 description 5
- 201000005202 lung cancer Diseases 0.000 description 5
- 208000020816 lung neoplasm Diseases 0.000 description 5
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 5
- 201000001441 melanoma Diseases 0.000 description 5
- 201000008968 osteosarcoma Diseases 0.000 description 5
- 201000002528 pancreatic cancer Diseases 0.000 description 5
- 208000008443 pancreatic carcinoma Diseases 0.000 description 5
- 201000009410 rhabdomyosarcoma Diseases 0.000 description 5
- 206010041823 squamous cell carcinoma Diseases 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 201000011549 stomach cancer Diseases 0.000 description 5
- 201000003120 testicular cancer Diseases 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 201000002510 thyroid cancer Diseases 0.000 description 5
- 201000005112 urinary bladder cancer Diseases 0.000 description 5
- 102100024965 Caspase recruitment domain-containing protein 11 Human genes 0.000 description 4
- 206010008342 Cervix carcinoma Diseases 0.000 description 4
- 208000000461 Esophageal Neoplasms Diseases 0.000 description 4
- 241000282412 Homo Species 0.000 description 4
- 101000761179 Homo sapiens Caspase recruitment domain-containing protein 11 Proteins 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 4
- 208000001894 Nasopharyngeal Neoplasms Diseases 0.000 description 4
- 206010061306 Nasopharyngeal cancer Diseases 0.000 description 4
- 206010030155 Oesophageal carcinoma Diseases 0.000 description 4
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 4
- 206010047115 Vasculitis Diseases 0.000 description 4
- 206010047741 Vulval cancer Diseases 0.000 description 4
- 208000004354 Vulvar Neoplasms Diseases 0.000 description 4
- 206010003246 arthritis Diseases 0.000 description 4
- 201000010881 cervical cancer Diseases 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 201000004101 esophageal cancer Diseases 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 230000035772 mutation Effects 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 206010044412 transitional cell carcinoma Diseases 0.000 description 4
- 201000005102 vulva cancer Diseases 0.000 description 4
- 230000004580 weight loss Effects 0.000 description 4
- 208000023275 Autoimmune disease Diseases 0.000 description 3
- 238000004566 IR spectroscopy Methods 0.000 description 3
- 239000002177 L01XE27 - Ibrutinib Substances 0.000 description 3
- 208000004337 Salivary Gland Neoplasms Diseases 0.000 description 3
- 206010061934 Salivary gland cancer Diseases 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 239000008186 active pharmaceutical agent Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000001363 autoimmune Effects 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 230000001684 chronic effect Effects 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 230000007812 deficiency Effects 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 230000002496 gastric effect Effects 0.000 description 3
- 229960001507 ibrutinib Drugs 0.000 description 3
- XYFPWWZEPKGCCK-GOSISDBHSA-N ibrutinib Chemical compound C1=2C(N)=NC=NC=2N([C@H]2CN(CCC2)C(=O)C=C)N=C1C(C=C1)=CC=C1OC1=CC=CC=C1 XYFPWWZEPKGCCK-GOSISDBHSA-N 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 201000006417 multiple sclerosis Diseases 0.000 description 3
- 230000037361 pathway Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 2
- 206010002556 Ankylosing Spondylitis Diseases 0.000 description 2
- 108091008875 B cell receptors Proteins 0.000 description 2
- 102100037598 B-cell lymphoma/leukemia 10 Human genes 0.000 description 2
- 101710109862 B-cell lymphoma/leukemia 10 Proteins 0.000 description 2
- 208000017392 BENTA disease Diseases 0.000 description 2
- 208000023328 Basedow disease Diseases 0.000 description 2
- 208000009137 Behcet syndrome Diseases 0.000 description 2
- 208000015943 Coeliac disease Diseases 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 201000003883 Cystic fibrosis Diseases 0.000 description 2
- 201000004624 Dermatitis Diseases 0.000 description 2
- 206010012438 Dermatitis atopic Diseases 0.000 description 2
- 206010012441 Dermatitis bullous Diseases 0.000 description 2
- 208000005189 Embolism Diseases 0.000 description 2
- 206010014561 Emphysema Diseases 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 206010016654 Fibrosis Diseases 0.000 description 2
- 208000007882 Gastritis Diseases 0.000 description 2
- 206010051066 Gastrointestinal stromal tumour Diseases 0.000 description 2
- 201000005569 Gout Diseases 0.000 description 2
- 208000015023 Graves' disease Diseases 0.000 description 2
- 208000030836 Hashimoto thyroiditis Diseases 0.000 description 2
- 206010020751 Hypersensitivity Diseases 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- 208000029462 Immunodeficiency disease Diseases 0.000 description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 2
- 208000019693 Lung disease Diseases 0.000 description 2
- 208000005777 Lupus Nephritis Diseases 0.000 description 2
- NUNCYLGRQPEXOA-UHFFFAOYSA-N N1N=CC(=C1)C(=O)NC1=CC(=NC=C1)C(F)(F)F Chemical compound N1N=CC(=C1)C(=O)NC1=CC(=NC=C1)C(F)(F)F NUNCYLGRQPEXOA-UHFFFAOYSA-N 0.000 description 2
- 206010030113 Oedema Diseases 0.000 description 2
- 206010033645 Pancreatitis Diseases 0.000 description 2
- 206010035664 Pneumonia Diseases 0.000 description 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 description 2
- 208000004756 Respiratory Insufficiency Diseases 0.000 description 2
- 201000010001 Silicosis Diseases 0.000 description 2
- 208000021386 Sjogren Syndrome Diseases 0.000 description 2
- 108091008874 T cell receptors Proteins 0.000 description 2
- 102000016266 T-Cell Antigen Receptors Human genes 0.000 description 2
- 210000001744 T-lymphocyte Anatomy 0.000 description 2
- 206010052779 Transplant rejections Diseases 0.000 description 2
- 206010046851 Uveitis Diseases 0.000 description 2
- 208000024340 acute graft versus host disease Diseases 0.000 description 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 description 2
- 208000026935 allergic disease Diseases 0.000 description 2
- 230000000172 allergic effect Effects 0.000 description 2
- 230000007815 allergy Effects 0.000 description 2
- 201000008937 atopic dermatitis Diseases 0.000 description 2
- 208000010668 atopic eczema Diseases 0.000 description 2
- 229910052790 beryllium Inorganic materials 0.000 description 2
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 206010006451 bronchitis Diseases 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 208000017760 chronic graft versus host disease Diseases 0.000 description 2
- 230000001886 ciliary effect Effects 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 201000001981 dermatomyositis Diseases 0.000 description 2
- 238000003795 desorption Methods 0.000 description 2
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 230000004761 fibrosis Effects 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 201000011243 gastrointestinal stromal tumor Diseases 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- 125000001475 halogen functional group Chemical group 0.000 description 2
- 230000001506 immunosuppresive effect Effects 0.000 description 2
- 208000027866 inflammatory disease Diseases 0.000 description 2
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 2
- 229940011051 isopropyl acetate Drugs 0.000 description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 2
- 230000002147 killing effect Effects 0.000 description 2
- 201000003445 large cell neuroendocrine carcinoma Diseases 0.000 description 2
- 229920001684 low density polyethylene Polymers 0.000 description 2
- 239000004702 low-density polyethylene Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 210000003593 megakaryocyte Anatomy 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 206010028417 myasthenia gravis Diseases 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 2
- 239000008177 pharmaceutical agent Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 208000005987 polymyositis Diseases 0.000 description 2
- 235000018102 proteins Nutrition 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 201000004193 respiratory failure Diseases 0.000 description 2
- 201000003068 rheumatic fever Diseases 0.000 description 2
- 201000000306 sarcoidosis Diseases 0.000 description 2
- 230000019491 signal transduction Effects 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 238000002336 sorption--desorption measurement Methods 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- ZVXKYWHJBYIYNI-UHFFFAOYSA-N 1h-pyrazole-4-carboxamide Chemical compound NC(=O)C=1C=NNC=1 ZVXKYWHJBYIYNI-UHFFFAOYSA-N 0.000 description 1
- TWJGQZBSEMDPQP-UHFFFAOYSA-N 2-chloro-n-[4-[5-(3,4-dichlorophenyl)-3-(2-methoxyethoxy)-1,2,4-triazol-1-yl]phenyl]acetamide Chemical compound C=1C=C(NC(=O)CCl)C=CC=1N1N=C(OCCOC)N=C1C1=CC=C(Cl)C(Cl)=C1 TWJGQZBSEMDPQP-UHFFFAOYSA-N 0.000 description 1
- 208000032116 Autoimmune Experimental Encephalomyelitis Diseases 0.000 description 1
- 102100027205 B-cell antigen receptor complex-associated protein alpha chain Human genes 0.000 description 1
- 208000003950 B-cell lymphoma Diseases 0.000 description 1
- 230000003844 B-cell-activation Effects 0.000 description 1
- 229940124291 BTK inhibitor Drugs 0.000 description 1
- 206010004485 Berylliosis Diseases 0.000 description 1
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 description 1
- 108010005843 Cysteine Proteases Proteins 0.000 description 1
- 102000005927 Cysteine Proteases Human genes 0.000 description 1
- 108010086291 Deubiquitinating Enzyme CYLD Proteins 0.000 description 1
- 206010061818 Disease progression Diseases 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 208000034951 Genetic Translocation Diseases 0.000 description 1
- 101000914489 Homo sapiens B-cell antigen receptor complex-associated protein alpha chain Proteins 0.000 description 1
- 101000643956 Homo sapiens Cytochrome b-c1 complex subunit Rieske, mitochondrial Proteins 0.000 description 1
- 101001099199 Homo sapiens RalA-binding protein 1 Proteins 0.000 description 1
- 101001109145 Homo sapiens Receptor-interacting serine/threonine-protein kinase 1 Proteins 0.000 description 1
- 101000777138 Homo sapiens Ubiquitin carboxyl-terminal hydrolase 42 Proteins 0.000 description 1
- 206010061598 Immunodeficiency Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 238000003109 Karl Fischer titration Methods 0.000 description 1
- 101150053046 MYD88 gene Proteins 0.000 description 1
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 description 1
- 102100024134 Myeloid differentiation primary response protein MyD88 Human genes 0.000 description 1
- 208000036110 Neuroinflammatory disease Diseases 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 108091000080 Phosphotransferase Proteins 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 102100022501 Receptor-interacting serine/threonine-protein kinase 1 Human genes 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- 101710184528 Scaffolding protein Proteins 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 230000006044 T cell activation Effects 0.000 description 1
- 102000004393 TNF receptor-associated factor 2 Human genes 0.000 description 1
- 108090000925 TNF receptor-associated factor 2 Proteins 0.000 description 1
- 102000003714 TNF receptor-associated factor 6 Human genes 0.000 description 1
- 108090000009 TNF receptor-associated factor 6 Proteins 0.000 description 1
- 102000040945 Transcription factor Human genes 0.000 description 1
- 108091023040 Transcription factor Proteins 0.000 description 1
- 108060008683 Tumor Necrosis Factor Receptor Proteins 0.000 description 1
- 102100031310 Ubiquitin carboxyl-terminal hydrolase 42 Human genes 0.000 description 1
- 102100024250 Ubiquitin carboxyl-terminal hydrolase CYLD Human genes 0.000 description 1
- 208000002495 Uterine Neoplasms Diseases 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 230000004721 adaptive immunity Effects 0.000 description 1
- 208000009956 adenocarcinoma Diseases 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000003281 allosteric effect Effects 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 239000012296 anti-solvent Substances 0.000 description 1
- 230000005809 anti-tumor immunity Effects 0.000 description 1
- 239000008365 aqueous carrier Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 210000003719 b-lymphocyte Anatomy 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000006552 constitutive activation Effects 0.000 description 1
- 238000003869 coulometry Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 230000005750 disease progression Effects 0.000 description 1
- 229940126534 drug product Drugs 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 210000003238 esophagus Anatomy 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000004868 gas analysis Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000003979 granulating agent Substances 0.000 description 1
- 230000003394 haemopoietic effect Effects 0.000 description 1
- 230000013632 homeostatic process Effects 0.000 description 1
- 102000052696 human MALT1 Human genes 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 230000002519 immonomodulatory effect Effects 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 230000007813 immunodeficiency Effects 0.000 description 1
- 230000004957 immunoregulator effect Effects 0.000 description 1
- 229940125721 immunosuppressive agent Drugs 0.000 description 1
- 239000003018 immunosuppressive agent Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000015788 innate immune response Effects 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 230000000527 lymphocytic effect Effects 0.000 description 1
- 201000000564 macroglobulinemia Diseases 0.000 description 1
- 210000003826 marginal zone b cell Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 229910021421 monocrystalline silicon Inorganic materials 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 238000010172 mouse model Methods 0.000 description 1
- 208000025113 myeloid leukemia Diseases 0.000 description 1
- 210000001989 nasopharynx Anatomy 0.000 description 1
- 230000003959 neuroinflammation Effects 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 230000005937 nuclear translocation Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 102000027450 oncoproteins Human genes 0.000 description 1
- 108091008819 oncoproteins Proteins 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940127084 other anti-cancer agent Drugs 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000009038 pharmacological inhibition Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 102000020233 phosphotransferase Human genes 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000004952 protein activity Effects 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 210000003079 salivary gland Anatomy 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 102000034285 signal transducing proteins Human genes 0.000 description 1
- 108091006024 signal transducing proteins Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000012430 stability testing Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000004441 surface measurement Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 210000002435 tendon Anatomy 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 102000003298 tumor necrosis factor receptor Human genes 0.000 description 1
- 230000034512 ubiquitination Effects 0.000 description 1
- 238000010798 ubiquitination Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
- A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2019075834 | 2019-02-22 | ||
| CNPCT/CN2019/075834 | 2019-02-22 | ||
| PCT/EP2020/054485 WO2020169736A1 (en) | 2019-02-22 | 2020-02-20 | Crystalline form of 1-(1-oxo-1,2-dihydroisoquinolin-5-yl)-5-(trifluoromethyl)-n-(2-(trifluoromethyl)pyridin-4-yl)-1h-pyrazole-4-carboxamide monohydrate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20210131371A true KR20210131371A (ko) | 2021-11-02 |
Family
ID=69723907
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020217029765A Withdrawn KR20210131371A (ko) | 2019-02-22 | 2020-02-20 | 1-(1-옥소-1,2-디하이드로이소퀴놀린-5-일)-5-(트리플루오로메틸)-n-(2-(트리플루오로메틸)피리딘-4-일)-1h-피라졸-4-카복사미드 일수화물의 결정질 형태 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US12269813B2 (enExample) |
| EP (1) | EP3927696B1 (enExample) |
| JP (1) | JP2022523368A (enExample) |
| KR (1) | KR20210131371A (enExample) |
| CN (1) | CN113474339B (enExample) |
| AU (1) | AU2020226723B2 (enExample) |
| BR (1) | BR112021016400A2 (enExample) |
| CA (1) | CA3129623A1 (enExample) |
| EA (1) | EA202192320A1 (enExample) |
| EC (1) | ECSP21067828A (enExample) |
| ES (1) | ES2966132T3 (enExample) |
| IL (1) | IL285675A (enExample) |
| JO (1) | JOP20210227A1 (enExample) |
| MA (1) | MA55019A (enExample) |
| MX (1) | MX2021010133A (enExample) |
| PE (1) | PE20212067A1 (enExample) |
| PH (1) | PH12021552018A1 (enExample) |
| SG (1) | SG11202108909SA (enExample) |
| TW (1) | TW202045495A (enExample) |
| UY (1) | UY38592A (enExample) |
| WO (1) | WO2020169736A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI795381B (zh) | 2016-12-21 | 2023-03-11 | 比利時商健生藥品公司 | 作為malt1抑制劑之吡唑衍生物 |
| US12404260B2 (en) | 2019-04-11 | 2025-09-02 | Janssen Pharmaceutica Nv | Pyridine rings containing derivatives as MALT1 inhibitors |
| BR112023003106A2 (pt) | 2020-08-21 | 2023-04-04 | Janssen Pharmaceutica Nv | Forma amorfa de um inibidor de malt1 e formulações do mesmo |
| BR112023017689A2 (pt) | 2021-03-03 | 2023-11-14 | Janssen Pharmaceutica Nv | Método de tratamento de uma condição com o uso de uma dose terapeuticamente eficaz do inibidor de malt1 jnj-67856633 (1-(1-oxo-1,2-di-hidroisoquinolin-5-il)-5-(trifluorometil)-n(2-(trifluorometil)piridin-4-il)-1h-pirazol-4-carboxamida) |
| EP4301365A1 (en) | 2021-03-03 | 2024-01-10 | Janssen Pharmaceutica NV | Combination therapy using a malt1 inhibitor and a btk inhibitor |
| AU2022326183A1 (en) * | 2021-08-09 | 2024-03-28 | Janssen Pharmaceutica Nv | Compositions for use in treating b-cell malignancies |
| WO2025073968A1 (en) | 2023-10-06 | 2025-04-10 | Ionctura Sa | Combination of roginolisib with a malt1-gls inhibitor |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007525183A (ja) | 2003-04-30 | 2007-09-06 | アジェンシス, インコーポレイテッド | 癌の処置および検出において有用な109p1d4と称される、核酸および対応タンパク質 |
| WO2007111904A2 (en) * | 2006-03-22 | 2007-10-04 | Vertex Pharmaceuticals Incorporated | C-met protein kinase inhibitors for the treatment of proliferative disorders |
| WO2008092292A1 (en) | 2007-01-17 | 2008-08-07 | The Hong Kong University Of Science And Technology | Isoquinolone compounds as subtype-selective agonists for melatonin receptors mt1 and mt2 |
| WO2011036885A1 (ja) * | 2009-09-25 | 2011-03-31 | 武田薬品工業株式会社 | 複素環化合物 |
| US20120071497A1 (en) | 2010-06-03 | 2012-03-22 | Pharmacyclics, Inc. | Methods of treating abc-dlbcl using inhibitors of bruton's tyrosine kinase |
| KR101580714B1 (ko) | 2010-06-03 | 2016-01-04 | 파마싸이클릭스 엘엘씨 | 브루톤 티로신 인산화효소(btk)의 억제제의 용도 |
| CN102947270B (zh) | 2010-06-22 | 2015-04-08 | 巴斯夫欧洲公司 | 制备4-羟基吡啶的方法 |
| MX2014014531A (es) * | 2012-05-31 | 2015-04-08 | Hoffmann La Roche | Derivados de aminoquinazolina y piridopirimidina. |
| HUE044351T2 (hu) | 2014-05-28 | 2019-10-28 | Novartis Ag | Új pirazolo-pirimidin származékok és azok alkalmazása MALT1 inhibitorként |
| EP3177366A4 (en) | 2014-08-08 | 2018-04-04 | Pharmacyclics LLC | Bruton's tyrosine kinase inhibitor combinations and uses thereof |
| US10835524B2 (en) * | 2015-06-24 | 2020-11-17 | University Of Florida Research Foundation, Incorporated | Compositions for the treatment of pancreatic cancer and uses thereof |
| CA3003820A1 (en) | 2015-11-13 | 2017-05-18 | Novartis Ag | Novel pyrazolo pyrimidine derivatives |
| EP3423452B1 (en) | 2016-03-01 | 2025-05-07 | University of Maryland, Baltimore | Wnt signaling pathway inhibitors for treatments of disease |
| TWI795381B (zh) * | 2016-12-21 | 2023-03-11 | 比利時商健生藥品公司 | 作為malt1抑制劑之吡唑衍生物 |
| EP3576744A1 (en) | 2017-02-01 | 2019-12-11 | Medivir Aktiebolag | Therapeutic applications of malt1 inhibitors |
| US11571427B2 (en) | 2017-12-28 | 2023-02-07 | The General Hospital Corporation | Targeting the CBM signalosome complex induces regulatory T cells to inflame the tumor microenvironment |
| WO2019161921A1 (de) | 2018-02-23 | 2019-08-29 | Industrieanlagen-Betriebsgesellschaft Mbh | Vorrichtung zum erzeugen eines magnetfelds, insbesondere für ein induktives ladesystem, und primäreinrichtung eines induktiven ladesystems zum dynamischen aufladen von fahrzeugen |
| WO2021138298A1 (en) | 2019-12-30 | 2021-07-08 | Rheos Medicines, Inc. | Malt1 modulators and uses thereof |
| BR112023003106A2 (pt) * | 2020-08-21 | 2023-04-04 | Janssen Pharmaceutica Nv | Forma amorfa de um inibidor de malt1 e formulações do mesmo |
-
2020
- 2020-02-20 AU AU2020226723A patent/AU2020226723B2/en not_active Expired - Fee Related
- 2020-02-20 SG SG11202108909SA patent/SG11202108909SA/en unknown
- 2020-02-20 JO JOP/2021/0227A patent/JOP20210227A1/ar unknown
- 2020-02-20 EP EP20707585.4A patent/EP3927696B1/en active Active
- 2020-02-20 EA EA202192320A patent/EA202192320A1/ru unknown
- 2020-02-20 KR KR1020217029765A patent/KR20210131371A/ko not_active Withdrawn
- 2020-02-20 WO PCT/EP2020/054485 patent/WO2020169736A1/en not_active Ceased
- 2020-02-20 MA MA055019A patent/MA55019A/fr unknown
- 2020-02-20 PH PH1/2021/552018A patent/PH12021552018A1/en unknown
- 2020-02-20 CN CN202080015968.5A patent/CN113474339B/zh active Active
- 2020-02-20 US US17/431,447 patent/US12269813B2/en active Active
- 2020-02-20 PE PE2021001372A patent/PE20212067A1/es unknown
- 2020-02-20 CA CA3129623A patent/CA3129623A1/en active Pending
- 2020-02-20 ES ES20707585T patent/ES2966132T3/es active Active
- 2020-02-20 JP JP2021549407A patent/JP2022523368A/ja active Pending
- 2020-02-20 MX MX2021010133A patent/MX2021010133A/es unknown
- 2020-02-20 BR BR112021016400-6A patent/BR112021016400A2/pt not_active Application Discontinuation
- 2020-02-21 UY UY0001038592A patent/UY38592A/es unknown
- 2020-02-21 TW TW109105620A patent/TW202045495A/zh unknown
-
2021
- 2021-08-17 IL IL285675A patent/IL285675A/en unknown
- 2021-09-14 EC ECSENADI202167828A patent/ECSP21067828A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN113474339A (zh) | 2021-10-01 |
| US20220127249A1 (en) | 2022-04-28 |
| CA3129623A1 (en) | 2020-08-27 |
| EP3927696A1 (en) | 2021-12-29 |
| PH12021552018A1 (en) | 2022-09-19 |
| JOP20210227A1 (ar) | 2023-01-30 |
| IL285675A (en) | 2021-10-31 |
| WO2020169736A1 (en) | 2020-08-27 |
| TW202045495A (zh) | 2020-12-16 |
| ECSP21067828A (es) | 2021-11-18 |
| AU2020226723B2 (en) | 2025-01-23 |
| UY38592A (es) | 2020-08-31 |
| JP2022523368A (ja) | 2022-04-22 |
| CN113474339B (zh) | 2025-02-25 |
| SG11202108909SA (en) | 2021-09-29 |
| AU2020226723A1 (en) | 2021-08-19 |
| PE20212067A1 (es) | 2021-10-26 |
| ES2966132T3 (es) | 2024-04-18 |
| MX2021010133A (es) | 2021-09-23 |
| EP3927696B1 (en) | 2023-10-18 |
| EA202192320A1 (ru) | 2021-11-16 |
| MA55019A (fr) | 2021-12-29 |
| US12269813B2 (en) | 2025-04-08 |
| BR112021016400A2 (pt) | 2021-10-13 |
| EP3927696C0 (en) | 2023-10-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR20210131371A (ko) | 1-(1-옥소-1,2-디하이드로이소퀴놀린-5-일)-5-(트리플루오로메틸)-n-(2-(트리플루오로메틸)피리딘-4-일)-1h-피라졸-4-카복사미드 일수화물의 결정질 형태 | |
| TW202110835A (zh) | 固態形式 | |
| CN111770914B (zh) | 作为神经激肽-1受体拮抗剂的化合物及其用途 | |
| TW202110836A (zh) | 固態形式 | |
| WO2023059598A1 (en) | Combination therapies of kras g12d inhibitors with shp-2 inhibitors | |
| US11918585B2 (en) | Formulations of an AXL/MER inhibitor | |
| JP5924453B2 (ja) | 二環式含窒素芳香族ヘテロ環アミド化合物 | |
| TWI771280B (zh) | 經取代之5,6-二氫-6-苯基苯并[f]異喹啉-2-胺化合物之固體形式 | |
| KR20140040671A (ko) | 아프레피탄트 l-프롤린 조성물 및 공결정 | |
| JP2014533719A (ja) | アプレピタントl−プロリン溶媒和化合物−組成物及び共結晶 | |
| US20220348565A1 (en) | Pharmaceutical compounds | |
| EA045924B1 (ru) | Кристаллическая форма моногидрата 1-(1-оксо-1,2-дигидроизохинолин-5-ил)-5-(трифторметил)-n-(2-(трифторметил)пиридин-4-ил)-1h-пиразол-4-карбоксамида | |
| HK40052643A (en) | Crystalline form of 1-(1-oxo-1,2-dihydroisoquinolin-5-yl)-5-(trifluoromethyl)-n-(2-(trifluoromethyl)pyridin-4-yl)-1h-pyrazole-4-carboxamide monohydrate | |
| RU2684278C1 (ru) | Фумарат пиридиламина и его кристаллы | |
| TW201829398A (zh) | 酪胺酸蛋白激酶調節劑、晶型及其用途 | |
| US20240140908A1 (en) | A pharmaceutical salt of an arylpyrrole derivative | |
| TW202342041A (zh) | 一種藥物組合物及所含活性成分化合物的製備方法 | |
| CN118451071A (zh) | 表皮生长因子受体抑制剂的结晶多晶型物及其组合物和方法 | |
| HK40052420A (en) | Formulations of an axl/mer inhibitor | |
| HK40052420B (en) | Formulations of an axl/mer inhibitor | |
| HK40029219B (en) | Compounds as neurokinin-1 receptor antagonists and uses thereof | |
| WO2019001551A1 (zh) | 一种咪唑并异吲哚类衍生物游离碱的晶型及其制备方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0105 | International application |
Patent event date: 20210915 Patent event code: PA01051R01D Comment text: International Patent Application |
|
| PG1501 | Laying open of application | ||
| PC1202 | Submission of document of withdrawal before decision of registration |
Comment text: [Withdrawal of Procedure relating to Patent, etc.] Withdrawal (Abandonment) Patent event code: PC12021R01D Patent event date: 20250306 |
|
| WITB | Written withdrawal of application |