RU2697393C2 - Кристаллическая твердая форма соли бензолсульфоновой кислоты и 2-[(4S)-6-(4-хлорфенил)-1-метил-8-(метилокси)-4H-[1,2,4]триазоло[4,3-a][1,4]бензодиазепин-4-ил]-N-этилацетамида, способ ее получения и фармацевтическая композиция, содержащая ее - Google Patents
Кристаллическая твердая форма соли бензолсульфоновой кислоты и 2-[(4S)-6-(4-хлорфенил)-1-метил-8-(метилокси)-4H-[1,2,4]триазоло[4,3-a][1,4]бензодиазепин-4-ил]-N-этилацетамида, способ ее получения и фармацевтическая композиция, содержащая ее Download PDFInfo
- Publication number
- RU2697393C2 RU2697393C2 RU2017107760A RU2017107760A RU2697393C2 RU 2697393 C2 RU2697393 C2 RU 2697393C2 RU 2017107760 A RU2017107760 A RU 2017107760A RU 2017107760 A RU2017107760 A RU 2017107760A RU 2697393 C2 RU2697393 C2 RU 2697393C2
- Authority
- RU
- Russia
- Prior art keywords
- ethylacetamide
- triazolo
- chlorophenyl
- methyloxy
- benzodiazepin
- Prior art date
Links
- AAAQFGUYHFJNHI-SFHVURJKSA-N 2-[(4S)-6-(4-chlorophenyl)-8-methoxy-1-methyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl]-N-ethylacetamide Chemical class N([C@H](C1=NN=C(C)N1C1=CC=C(OC)C=C11)CC(=O)NCC)=C1C1=CC=C(Cl)C=C1 AAAQFGUYHFJNHI-SFHVURJKSA-N 0.000 title claims abstract description 87
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 title claims abstract description 75
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 43
- 239000007787 solid Substances 0.000 title claims abstract description 39
- 238000004519 manufacturing process Methods 0.000 title description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 67
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 20
- 238000001228 spectrum Methods 0.000 claims abstract description 19
- 239000000126 substance Substances 0.000 claims abstract description 9
- 238000005481 NMR spectroscopy Methods 0.000 claims abstract description 4
- 230000000694 effects Effects 0.000 claims abstract description 4
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 71
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 54
- 150000008107 benzenesulfonic acids Chemical class 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 23
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 18
- 229940125763 bromodomain inhibitor Drugs 0.000 claims description 17
- 239000003112 inhibitor Substances 0.000 claims description 16
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 13
- 239000012453 solvate Substances 0.000 claims description 10
- 239000000314 lubricant Substances 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 7
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 6
- 229960000913 crospovidone Drugs 0.000 claims description 6
- 239000013078 crystal Substances 0.000 claims description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical group [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 6
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 claims description 6
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 claims description 6
- 239000000945 filler Substances 0.000 claims description 5
- 238000007323 disproportionation reaction Methods 0.000 claims description 4
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 3
- 229930195725 Mannitol Natural products 0.000 claims description 3
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 235000019359 magnesium stearate Nutrition 0.000 claims description 3
- 239000000594 mannitol Substances 0.000 claims description 3
- 235000010355 mannitol Nutrition 0.000 claims description 3
- 239000008108 microcrystalline cellulose Substances 0.000 claims description 3
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims description 3
- 229940016286 microcrystalline cellulose Drugs 0.000 claims description 3
- 230000009467 reduction Effects 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 18
- 239000000843 powder Substances 0.000 abstract description 5
- 239000000825 pharmaceutical preparation Substances 0.000 abstract description 3
- 229940127557 pharmaceutical product Drugs 0.000 abstract description 3
- 206010028980 Neoplasm Diseases 0.000 description 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 20
- 201000010099 disease Diseases 0.000 description 19
- 201000011510 cancer Diseases 0.000 description 17
- 230000001154 acute effect Effects 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 16
- 239000000523 sample Substances 0.000 description 12
- 108050009021 Bromodomains Proteins 0.000 description 10
- 102000001805 Bromodomains Human genes 0.000 description 10
- 239000000725 suspension Substances 0.000 description 9
- 229940124597 therapeutic agent Drugs 0.000 description 9
- 206010030113 Oedema Diseases 0.000 description 8
- 230000001363 autoimmune Effects 0.000 description 8
- 230000001684 chronic effect Effects 0.000 description 8
- 230000004968 inflammatory condition Effects 0.000 description 8
- 208000032839 leukemia Diseases 0.000 description 8
- 230000018044 dehydration Effects 0.000 description 7
- 238000006297 dehydration reaction Methods 0.000 description 7
- 239000012065 filter cake Substances 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 6
- 229940124531 pharmaceutical excipient Drugs 0.000 description 6
- 208000011580 syndromic disease Diseases 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 5
- 239000013543 active substance Substances 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 206010012601 diabetes mellitus Diseases 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- -1 glidants Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 230000001225 therapeutic effect Effects 0.000 description 5
- 206010009944 Colon cancer Diseases 0.000 description 4
- 206010040047 Sepsis Diseases 0.000 description 4
- 206010047115 Vasculitis Diseases 0.000 description 4
- 208000036142 Viral infection Diseases 0.000 description 4
- 210000001367 artery Anatomy 0.000 description 4
- 239000004067 bulking agent Substances 0.000 description 4
- 239000002274 desiccant Substances 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 210000000056 organ Anatomy 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 230000009385 viral infection Effects 0.000 description 4
- 208000031261 Acute myeloid leukaemia Diseases 0.000 description 3
- 208000026310 Breast neoplasm Diseases 0.000 description 3
- 201000009030 Carcinoma Diseases 0.000 description 3
- 208000009889 Herpes Simplex Diseases 0.000 description 3
- 208000007514 Herpes zoster Diseases 0.000 description 3
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 3
- 208000001344 Macular Edema Diseases 0.000 description 3
- 206010025415 Macular oedema Diseases 0.000 description 3
- 208000034578 Multiple myelomas Diseases 0.000 description 3
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 description 3
- 206010035226 Plasma cell myeloma Diseases 0.000 description 3
- 206010038910 Retinitis Diseases 0.000 description 3
- 206010039710 Scleroderma Diseases 0.000 description 3
- 206010040070 Septic Shock Diseases 0.000 description 3
- 206010046851 Uveitis Diseases 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 201000010230 macular retinal edema Diseases 0.000 description 3
- 201000006417 multiple sclerosis Diseases 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 230000002980 postoperative effect Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 2
- 201000001320 Atherosclerosis Diseases 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 description 2
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 201000006474 Brain Ischemia Diseases 0.000 description 2
- 206010006187 Breast cancer Diseases 0.000 description 2
- 208000011691 Burkitt lymphomas Diseases 0.000 description 2
- 206010008342 Cervix carcinoma Diseases 0.000 description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 2
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 description 2
- 206010009900 Colitis ulcerative Diseases 0.000 description 2
- 208000001333 Colorectal Neoplasms Diseases 0.000 description 2
- 208000011231 Crohn disease Diseases 0.000 description 2
- 201000004624 Dermatitis Diseases 0.000 description 2
- 208000003556 Dry Eye Syndromes Diseases 0.000 description 2
- 206010013774 Dry eye Diseases 0.000 description 2
- 208000037487 Endotoxemia Diseases 0.000 description 2
- 208000000461 Esophageal Neoplasms Diseases 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 206010051066 Gastrointestinal stromal tumour Diseases 0.000 description 2
- 208000007465 Giant cell arteritis Diseases 0.000 description 2
- 201000005569 Gout Diseases 0.000 description 2
- 241000725303 Human immunodeficiency virus Species 0.000 description 2
- 241000701806 Human papillomavirus Species 0.000 description 2
- 208000035150 Hypercholesterolemia Diseases 0.000 description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 2
- 208000008839 Kidney Neoplasms Diseases 0.000 description 2
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 description 2
- 206010025323 Lymphomas Diseases 0.000 description 2
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 description 2
- 206010030155 Oesophageal carcinoma Diseases 0.000 description 2
- 206010033128 Ovarian cancer Diseases 0.000 description 2
- 206010061535 Ovarian neoplasm Diseases 0.000 description 2
- 206010033645 Pancreatitis Diseases 0.000 description 2
- 206010033647 Pancreatitis acute Diseases 0.000 description 2
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 description 2
- 206010060862 Prostate cancer Diseases 0.000 description 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- 206010064911 Pulmonary arterial hypertension Diseases 0.000 description 2
- 206010038389 Renal cancer Diseases 0.000 description 2
- 206010063837 Reperfusion injury Diseases 0.000 description 2
- 206010041067 Small cell lung cancer Diseases 0.000 description 2
- 206010051379 Systemic Inflammatory Response Syndrome Diseases 0.000 description 2
- 208000024770 Thyroid neoplasm Diseases 0.000 description 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 2
- 201000006704 Ulcerative Colitis Diseases 0.000 description 2
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 2
- 241000700605 Viruses Species 0.000 description 2
- 201000003229 acute pancreatitis Diseases 0.000 description 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 201000010881 cervical cancer Diseases 0.000 description 2
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 239000007884 disintegrant Substances 0.000 description 2
- 201000004101 esophageal cancer Diseases 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 201000011243 gastrointestinal stromal tumor Diseases 0.000 description 2
- 229920001903 high density polyethylene Polymers 0.000 description 2
- 239000004700 high-density polyethylene Substances 0.000 description 2
- 206010023332 keratitis Diseases 0.000 description 2
- 201000010666 keratoconjunctivitis Diseases 0.000 description 2
- 201000010982 kidney cancer Diseases 0.000 description 2
- 208000014018 liver neoplasm Diseases 0.000 description 2
- 201000005202 lung cancer Diseases 0.000 description 2
- 208000020816 lung neoplasm Diseases 0.000 description 2
- 229960001855 mannitol Drugs 0.000 description 2
- 230000035772 mutation Effects 0.000 description 2
- 208000010125 myocardial infarction Diseases 0.000 description 2
- 201000008383 nephritis Diseases 0.000 description 2
- 201000008482 osteoarthritis Diseases 0.000 description 2
- 244000045947 parasite Species 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 230000007420 reactivation Effects 0.000 description 2
- 210000001957 retinal vein Anatomy 0.000 description 2
- 230000036303 septic shock Effects 0.000 description 2
- 230000019491 signal transduction Effects 0.000 description 2
- 208000000587 small cell lung carcinoma Diseases 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 2
- 206010043207 temporal arteritis Diseases 0.000 description 2
- 201000002510 thyroid cancer Diseases 0.000 description 2
- 208000030901 thyroid gland follicular carcinoma Diseases 0.000 description 2
- 239000003053 toxin Substances 0.000 description 2
- 231100000765 toxin Toxicity 0.000 description 2
- 108700012359 toxins Proteins 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- 238000004922 13C solid-state nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- ZZVDXRCAGGQFAK-UHFFFAOYSA-N 2h-oxazaphosphinine Chemical class N1OC=CC=P1 ZZVDXRCAGGQFAK-UHFFFAOYSA-N 0.000 description 1
- 208000004476 Acute Coronary Syndrome Diseases 0.000 description 1
- 208000009304 Acute Kidney Injury Diseases 0.000 description 1
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 description 1
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 description 1
- 206010000871 Acute monocytic leukaemia Diseases 0.000 description 1
- 208000036762 Acute promyelocytic leukaemia Diseases 0.000 description 1
- 208000026872 Addison Disease Diseases 0.000 description 1
- 206010001258 Adenoviral infections Diseases 0.000 description 1
- 201000004384 Alopecia Diseases 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 208000009137 Behcet syndrome Diseases 0.000 description 1
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 description 1
- 206010004659 Biliary cirrhosis Diseases 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 108010006654 Bleomycin Proteins 0.000 description 1
- 208000020084 Bone disease Diseases 0.000 description 1
- 208000003174 Brain Neoplasms Diseases 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 201000006082 Chickenpox Diseases 0.000 description 1
- 206010008609 Cholangitis sclerosing Diseases 0.000 description 1
- 208000002691 Choroiditis Diseases 0.000 description 1
- 208000000668 Chronic Pancreatitis Diseases 0.000 description 1
- 241000710777 Classical swine fever virus Species 0.000 description 1
- 208000002330 Congenital Heart Defects Diseases 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000711573 Coronaviridae Species 0.000 description 1
- 208000012609 Cowden disease Diseases 0.000 description 1
- 201000002847 Cowden syndrome Diseases 0.000 description 1
- 229920002785 Croscarmellose sodium Polymers 0.000 description 1
- 229940123780 DNA topoisomerase I inhibitor Drugs 0.000 description 1
- 229940124087 DNA topoisomerase II inhibitor Drugs 0.000 description 1
- 108010092160 Dactinomycin Proteins 0.000 description 1
- 206010012438 Dermatitis atopic Diseases 0.000 description 1
- 206010012689 Diabetic retinopathy Diseases 0.000 description 1
- 208000005189 Embolism Diseases 0.000 description 1
- 206010014733 Endometrial cancer Diseases 0.000 description 1
- 206010014759 Endometrial neoplasm Diseases 0.000 description 1
- 206010014967 Ependymoma Diseases 0.000 description 1
- 208000001351 Epiretinal Membrane Diseases 0.000 description 1
- 208000031637 Erythroblastic Acute Leukemia Diseases 0.000 description 1
- 208000036566 Erythroleukaemia Diseases 0.000 description 1
- 208000006168 Ewing Sarcoma Diseases 0.000 description 1
- 208000007569 Giant Cell Tumors Diseases 0.000 description 1
- 208000032612 Glial tumor Diseases 0.000 description 1
- 206010018338 Glioma Diseases 0.000 description 1
- 206010018364 Glomerulonephritis Diseases 0.000 description 1
- 206010072579 Granulomatosis with polyangiitis Diseases 0.000 description 1
- 208000031886 HIV Infections Diseases 0.000 description 1
- 208000037357 HIV infectious disease Diseases 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 208000017604 Hodgkin disease Diseases 0.000 description 1
- 208000021519 Hodgkin lymphoma Diseases 0.000 description 1
- 208000010747 Hodgkins lymphoma Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 208000005726 Inflammatory Breast Neoplasms Diseases 0.000 description 1
- 206010021980 Inflammatory carcinoma of the breast Diseases 0.000 description 1
- 206010022941 Iridocyclitis Diseases 0.000 description 1
- 206010023125 Jarisch-Herxheimer reaction Diseases 0.000 description 1
- 208000002260 Keloid Diseases 0.000 description 1
- 206010023330 Keloid scar Diseases 0.000 description 1
- 208000017170 Lipid metabolism disease Diseases 0.000 description 1
- 208000005777 Lupus Nephritis Diseases 0.000 description 1
- 208000031471 Macular fibrosis Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 208000001940 Massive Hepatic Necrosis Diseases 0.000 description 1
- 208000000172 Medulloblastoma Diseases 0.000 description 1
- 208000035490 Megakaryoblastic Acute Leukemia Diseases 0.000 description 1
- 201000009906 Meningitis Diseases 0.000 description 1
- 206010027406 Mesothelioma Diseases 0.000 description 1
- 208000029725 Metabolic bone disease Diseases 0.000 description 1
- 102000029749 Microtubule Human genes 0.000 description 1
- 108091022875 Microtubule Proteins 0.000 description 1
- 208000035489 Monocytic Acute Leukemia Diseases 0.000 description 1
- 208000003445 Mouth Neoplasms Diseases 0.000 description 1
- 208000008770 Multiple Hamartoma Syndrome Diseases 0.000 description 1
- 208000010718 Multiple Organ Failure Diseases 0.000 description 1
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 1
- 208000003926 Myelitis Diseases 0.000 description 1
- 206010028594 Myocardial fibrosis Diseases 0.000 description 1
- 208000009525 Myocarditis Diseases 0.000 description 1
- 201000002481 Myositis Diseases 0.000 description 1
- 208000001894 Nasopharyngeal Neoplasms Diseases 0.000 description 1
- 206010061306 Nasopharyngeal cancer Diseases 0.000 description 1
- 206010029260 Neuroblastoma Diseases 0.000 description 1
- 101100020663 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) ppm-1 gene Proteins 0.000 description 1
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 1
- 108020005497 Nuclear hormone receptor Proteins 0.000 description 1
- 102000007399 Nuclear hormone receptor Human genes 0.000 description 1
- 208000003435 Optic Neuritis Diseases 0.000 description 1
- 206010049088 Osteopenia Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 1
- 206010033649 Pancreatitis chronic Diseases 0.000 description 1
- 208000009608 Papillomavirus Infections Diseases 0.000 description 1
- 208000031481 Pathologic Constriction Diseases 0.000 description 1
- 208000007452 Plasmacytoma Diseases 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- 206010035742 Pneumonitis Diseases 0.000 description 1
- 206010036346 Posterior capsule opacification Diseases 0.000 description 1
- 208000003971 Posterior uveitis Diseases 0.000 description 1
- 208000005585 Poxviridae Infections Diseases 0.000 description 1
- 208000006311 Pyoderma Diseases 0.000 description 1
- 208000033626 Renal failure acute Diseases 0.000 description 1
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 description 1
- 208000004756 Respiratory Insufficiency Diseases 0.000 description 1
- 206010038848 Retinal detachment Diseases 0.000 description 1
- 206010038899 Retinal telangiectasia Diseases 0.000 description 1
- 208000007014 Retinitis pigmentosa Diseases 0.000 description 1
- 208000004337 Salivary Gland Neoplasms Diseases 0.000 description 1
- 206010061934 Salivary gland cancer Diseases 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- 206010039705 Scleritis Diseases 0.000 description 1
- 206010040628 Sialoadenitis Diseases 0.000 description 1
- 241000700584 Simplexvirus Species 0.000 description 1
- 208000021386 Sjogren Syndrome Diseases 0.000 description 1
- 208000005718 Stomach Neoplasms Diseases 0.000 description 1
- 201000009594 Systemic Scleroderma Diseases 0.000 description 1
- 206010042953 Systemic sclerosis Diseases 0.000 description 1
- 206010042971 T-cell lymphoma Diseases 0.000 description 1
- 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 description 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 1
- 208000001106 Takayasu Arteritis Diseases 0.000 description 1
- 208000024313 Testicular Neoplasms Diseases 0.000 description 1
- 206010057644 Testis cancer Diseases 0.000 description 1
- 239000000365 Topoisomerase I Inhibitor Substances 0.000 description 1
- 239000000317 Topoisomerase II Inhibitor Substances 0.000 description 1
- 206010044248 Toxic shock syndrome Diseases 0.000 description 1
- 231100000650 Toxic shock syndrome Toxicity 0.000 description 1
- 206010052779 Transplant rejections Diseases 0.000 description 1
- 206010046865 Vaccinia virus infection Diseases 0.000 description 1
- 206010046980 Varicella Diseases 0.000 description 1
- 241000700647 Variola virus Species 0.000 description 1
- 229940122803 Vinca alkaloid Drugs 0.000 description 1
- 206010047642 Vitiligo Diseases 0.000 description 1
- 208000035307 Vitreous adhesions Diseases 0.000 description 1
- 206010047741 Vulval cancer Diseases 0.000 description 1
- 208000004354 Vulvar Neoplasms Diseases 0.000 description 1
- 208000008383 Wilms tumor Diseases 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229930183665 actinomycin Natural products 0.000 description 1
- 208000021841 acute erythroid leukemia Diseases 0.000 description 1
- 201000011040 acute kidney failure Diseases 0.000 description 1
- 206010069351 acute lung injury Diseases 0.000 description 1
- 208000037833 acute lymphoblastic T-cell leukemia Diseases 0.000 description 1
- 208000013593 acute megakaryoblastic leukemia Diseases 0.000 description 1
- 208000020700 acute megakaryocytic leukemia Diseases 0.000 description 1
- 208000012998 acute renal failure Diseases 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 231100000360 alopecia Toxicity 0.000 description 1
- 230000033115 angiogenesis Effects 0.000 description 1
- 201000004612 anterior uveitis Diseases 0.000 description 1
- 229940045799 anthracyclines and related substance Drugs 0.000 description 1
- 230000003432 anti-folate effect Effects 0.000 description 1
- 230000000340 anti-metabolite Effects 0.000 description 1
- 229940127074 antifolate Drugs 0.000 description 1
- 229940100197 antimetabolite Drugs 0.000 description 1
- 239000002256 antimetabolite Substances 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 208000007474 aortic aneurysm Diseases 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 206010069664 atopic keratoconjunctivitis Diseases 0.000 description 1
- KMUZXKYZAJQLTR-FERBBOLQSA-N benzene 2-[(4S)-6-(4-chlorophenyl)-8-methoxy-1-methyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl]-N-ethylacetamide Chemical compound c1ccccc1.CCNC(=O)C[C@@H]1N=C(c2ccc(Cl)cc2)c2cc(OC)ccc2-n2c(C)nnc12 KMUZXKYZAJQLTR-FERBBOLQSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical class [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- WWIWLTSSHDKOKO-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1.OS(=O)(=O)C1=CC=CC=C1 WWIWLTSSHDKOKO-UHFFFAOYSA-N 0.000 description 1
- 150000001557 benzodiazepines Chemical class 0.000 description 1
- 229940124748 beta 2 agonist Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 229960001561 bleomycin Drugs 0.000 description 1
- OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 208000019748 bullous skin disease Diseases 0.000 description 1
- 206010061592 cardiac fibrillation Diseases 0.000 description 1
- 230000022131 cell cycle Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 201000010903 chronic neutrophilic leukemia Diseases 0.000 description 1
- 208000025302 chronic primary adrenal insufficiency Diseases 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000002648 combination therapy Methods 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 208000028831 congenital heart disease Diseases 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 229960001681 croscarmellose sodium Drugs 0.000 description 1
- 238000005388 cross polarization Methods 0.000 description 1
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 150000004141 diterpene derivatives Chemical class 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 206010014599 encephalitis Diseases 0.000 description 1
- 206010014665 endocarditis Diseases 0.000 description 1
- 230000001973 epigenetic effect Effects 0.000 description 1
- 210000000981 epithelium Anatomy 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- MVPICKVDHDWCJQ-UHFFFAOYSA-N ethyl 3-pyrrolidin-1-ylpropanoate Chemical group CCOC(=O)CCN1CCCC1 MVPICKVDHDWCJQ-UHFFFAOYSA-N 0.000 description 1
- 230000002600 fibrillogenic effect Effects 0.000 description 1
- 230000003176 fibrotic effect Effects 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000004052 folic acid antagonist Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 206010017758 gastric cancer Diseases 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 208000005017 glioblastoma Diseases 0.000 description 1
- 201000009277 hairy cell leukemia Diseases 0.000 description 1
- 201000010536 head and neck cancer Diseases 0.000 description 1
- 208000014829 head and neck neoplasm Diseases 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002489 hematologic effect Effects 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 1
- 229940121372 histone deacetylase inhibitor Drugs 0.000 description 1
- 239000003276 histone deacetylase inhibitor Substances 0.000 description 1
- 239000002944 hormone and hormone analog Substances 0.000 description 1
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 239000002955 immunomodulating agent Substances 0.000 description 1
- 201000004653 inflammatory breast carcinoma Diseases 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000028709 inflammatory response Effects 0.000 description 1
- 206010022000 influenza Diseases 0.000 description 1
- 208000036971 interstitial lung disease 2 Diseases 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- 210000001117 keloid Anatomy 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 208000012987 lip and oral cavity carcinoma Diseases 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 201000007270 liver cancer Diseases 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 201000005296 lung carcinoma Diseases 0.000 description 1
- 208000003747 lymphoid leukemia Diseases 0.000 description 1
- 208000002780 macular degeneration Diseases 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 201000008806 mesenchymal cell neoplasm Diseases 0.000 description 1
- 108020004999 messenger RNA Proteins 0.000 description 1
- 210000004688 microtubule Anatomy 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 208000029744 multiple organ dysfunction syndrome Diseases 0.000 description 1
- 239000003149 muscarinic antagonist Substances 0.000 description 1
- 230000009826 neoplastic cell growth Effects 0.000 description 1
- 201000008026 nephroblastoma Diseases 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 201000002165 neuroretinitis Diseases 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- OSTGTTZJOCZWJG-UHFFFAOYSA-N nitrosourea Chemical compound NC(=O)N=NO OSTGTTZJOCZWJG-UHFFFAOYSA-N 0.000 description 1
- 102000037979 non-receptor tyrosine kinases Human genes 0.000 description 1
- 108091008046 non-receptor tyrosine kinases Proteins 0.000 description 1
- 238000001208 nuclear magnetic resonance pulse sequence Methods 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 201000008968 osteosarcoma Diseases 0.000 description 1
- 201000002528 pancreatic cancer Diseases 0.000 description 1
- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
- 201000007407 panuveitis Diseases 0.000 description 1
- 208000008494 pericarditis Diseases 0.000 description 1
- 208000030613 peripheral artery disease Diseases 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 230000001817 pituitary effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000000861 pro-apoptotic effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 201000002793 renal fibrosis Diseases 0.000 description 1
- 201000004193 respiratory failure Diseases 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000004264 retinal detachment Effects 0.000 description 1
- 201000009410 rhabdomyosarcoma Diseases 0.000 description 1
- 208000004124 rheumatic heart disease Diseases 0.000 description 1
- 201000000306 sarcoidosis Diseases 0.000 description 1
- 230000037390 scarring Effects 0.000 description 1
- 208000010157 sclerosing cholangitis Diseases 0.000 description 1
- 208000001050 sialadenitis Diseases 0.000 description 1
- 229940045902 sodium stearyl fumarate Drugs 0.000 description 1
- 238000000279 solid-state nuclear magnetic resonance spectrum Methods 0.000 description 1
- 206010041823 squamous cell carcinoma Diseases 0.000 description 1
- 201000011549 stomach cancer Diseases 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 201000003120 testicular cancer Diseases 0.000 description 1
- 206010043778 thyroiditis Diseases 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000002103 transcriptional effect Effects 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 150000004654 triazenes Chemical class 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 108010002164 tyrosine receptor Proteins 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 208000007089 vaccinia Diseases 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 201000005102 vulva cancer Diseases 0.000 description 1
Images
Classifications
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
- A61K31/5513—1,4-Benzodiazepines, e.g. diazepam or clozapine
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
- A61K31/5513—1,4-Benzodiazepines, e.g. diazepam or clozapine
- A61K31/5517—1,4-Benzodiazepines, e.g. diazepam or clozapine condensed with five-membered rings having nitrogen as a ring hetero atom, e.g. imidazobenzodiazepines, triazolam
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/2027—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P37/02—Immunomodulators
-
- 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
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/29—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
-
- 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)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Physiology (AREA)
- Nutrition Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462058753P | 2014-10-02 | 2014-10-02 | |
| US62/058,753 | 2014-10-02 | ||
| PCT/EP2015/072515 WO2016050821A1 (en) | 2014-10-02 | 2015-09-30 | Compound |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| RU2017107760A RU2017107760A (ru) | 2018-11-02 |
| RU2017107760A3 RU2017107760A3 (enExample) | 2019-03-01 |
| RU2697393C2 true RU2697393C2 (ru) | 2019-08-14 |
Family
ID=54238438
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2017107760A RU2697393C2 (ru) | 2014-10-02 | 2015-09-30 | Кристаллическая твердая форма соли бензолсульфоновой кислоты и 2-[(4S)-6-(4-хлорфенил)-1-метил-8-(метилокси)-4H-[1,2,4]триазоло[4,3-a][1,4]бензодиазепин-4-ил]-N-этилацетамида, способ ее получения и фармацевтическая композиция, содержащая ее |
Country Status (10)
| Country | Link |
|---|---|
| US (3) | US9975901B2 (enExample) |
| EP (1) | EP3201199A1 (enExample) |
| JP (1) | JP2017530155A (enExample) |
| KR (1) | KR20170055549A (enExample) |
| CN (1) | CN106715439A (enExample) |
| AU (1) | AU2015326910B2 (enExample) |
| BR (1) | BR112017006342A2 (enExample) |
| CA (1) | CA2960090A1 (enExample) |
| RU (1) | RU2697393C2 (enExample) |
| WO (1) | WO2016050821A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3608317A1 (en) | 2012-01-12 | 2020-02-12 | Yale University | Compounds & methods for the enhanced degradation of targeted proteins & other polypeptides by an e3 ubiquitin ligase |
| US20180228907A1 (en) | 2014-04-14 | 2018-08-16 | Arvinas, Inc. | Cereblon ligands and bifunctional compounds comprising the same |
| WO2016090219A1 (en) | 2014-12-05 | 2016-06-09 | H. Lee Moffitt Cancer Center And Research Institute, Inc. | Bromodomain inhibitor as adjuvant in cancer immunotherapy |
| EP3270917A4 (en) | 2015-03-18 | 2018-08-08 | Arvinas, Inc. | Compounds and methods for the enhanced degradation of targeted proteins |
| EP3337476A4 (en) | 2015-08-19 | 2019-09-04 | Arvinas, Inc. | Compounds and methods for the targeted degradation of bromodomain-containing proteins |
| US20190284192A1 (en) | 2016-11-10 | 2019-09-19 | Luoxin Pharmaceutical (Shanghai) Co., Ltd. | Nitrogenous macrocyclic compound, preparation method therefor, pharmaceutical composition and application thereof |
| KR102747905B1 (ko) | 2017-01-31 | 2024-12-31 | 아비나스 오퍼레이션스, 인코포레이티드 | 세레블론 리간드 및 이를 포함하는 이작용성 화합물 |
| EP3743066A4 (en) | 2018-01-26 | 2021-09-08 | Yale University | IMIDE-BASED PROTEOLYSIS MODULATORS AND RELATED METHODS OF USE |
| WO2019199816A1 (en) | 2018-04-13 | 2019-10-17 | Arvinas Operations, Inc. | Cereblon ligands and bifunctional compounds comprising the same |
| PH12022551486A1 (en) | 2019-12-19 | 2023-11-13 | Arvinas Operations Inc | Compounds and methods for the targeted degradation of androgen receptor |
| CN111533745A (zh) * | 2020-05-20 | 2020-08-14 | 成都药明康德新药开发有限公司 | 叔丁基-3-(氨基甲基)二氢-5h-三唑并二氮杂卓-8(9h)-甲酸基酯制法 |
| WO2025049555A1 (en) | 2023-08-31 | 2025-03-06 | Oerth Bio Llc | Compositions and methods for targeted inhibition and degradation of proteins in an insect cell |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0934940A1 (en) * | 1996-06-12 | 1999-08-11 | Japan Tobacco Inc. | Cytokine production inhibitors, triazepine compounds, and intermediates thereof |
| EP2239264A1 (en) * | 2007-12-28 | 2010-10-13 | Mitsubishi Tanabe Pharma Corporation | Antitumor agent |
| EA201290184A1 (ru) * | 2009-11-05 | 2012-12-28 | ГЛАКСОСМИТКЛАЙН ЭлЭлСи | Бензодиазепиновый ингибитор бромодомена |
| EA201290183A1 (ru) * | 2009-11-05 | 2012-12-28 | ГЛАКСОСМИТКЛАЙН ЭлЭлСи | Бензодиазепиновый ингибитор бромодомена |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201106743D0 (en) * | 2011-04-21 | 2011-06-01 | Glaxosmithkline Llc | Novel compounds |
| DK2773354T3 (da) * | 2011-11-01 | 2019-08-05 | Resverlogix Corp | Oralformuleringer med øjeblikkelig frigivelse for substituerede quinazolinoner |
| US9492460B2 (en) * | 2013-02-27 | 2016-11-15 | Bristol-Myers Squibb Company | Carbazole compounds useful as bromodomain inhibitors |
-
2015
- 2015-09-30 EP EP15771952.7A patent/EP3201199A1/en not_active Withdrawn
- 2015-09-30 CN CN201580053064.0A patent/CN106715439A/zh active Pending
- 2015-09-30 AU AU2015326910A patent/AU2015326910B2/en not_active Ceased
- 2015-09-30 US US15/515,683 patent/US9975901B2/en not_active Expired - Fee Related
- 2015-09-30 RU RU2017107760A patent/RU2697393C2/ru active
- 2015-09-30 JP JP2017517713A patent/JP2017530155A/ja active Pending
- 2015-09-30 CA CA2960090A patent/CA2960090A1/en not_active Abandoned
- 2015-09-30 WO PCT/EP2015/072515 patent/WO2016050821A1/en not_active Ceased
- 2015-09-30 KR KR1020177010949A patent/KR20170055549A/ko not_active Withdrawn
- 2015-09-30 BR BR112017006342A patent/BR112017006342A2/pt not_active Application Discontinuation
-
2018
- 2018-04-18 US US15/955,857 patent/US10450319B2/en not_active Expired - Fee Related
-
2019
- 2019-09-05 US US16/561,208 patent/US20190389870A1/en not_active Abandoned
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0934940A1 (en) * | 1996-06-12 | 1999-08-11 | Japan Tobacco Inc. | Cytokine production inhibitors, triazepine compounds, and intermediates thereof |
| EP2239264A1 (en) * | 2007-12-28 | 2010-10-13 | Mitsubishi Tanabe Pharma Corporation | Antitumor agent |
| EA201290184A1 (ru) * | 2009-11-05 | 2012-12-28 | ГЛАКСОСМИТКЛАЙН ЭлЭлСи | Бензодиазепиновый ингибитор бромодомена |
| EA201290183A1 (ru) * | 2009-11-05 | 2012-12-28 | ГЛАКСОСМИТКЛАЙН ЭлЭлСи | Бензодиазепиновый ингибитор бромодомена |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106715439A (zh) | 2017-05-24 |
| WO2016050821A1 (en) | 2016-04-07 |
| US20170298071A1 (en) | 2017-10-19 |
| US9975901B2 (en) | 2018-05-22 |
| CA2960090A1 (en) | 2016-04-07 |
| AU2015326910A1 (en) | 2017-03-30 |
| JP2017530155A (ja) | 2017-10-12 |
| RU2017107760A (ru) | 2018-11-02 |
| RU2017107760A3 (enExample) | 2019-03-01 |
| AU2015326910B2 (en) | 2018-03-01 |
| BR112017006342A2 (pt) | 2017-12-19 |
| US20180305365A1 (en) | 2018-10-25 |
| US20190389870A1 (en) | 2019-12-26 |
| EP3201199A1 (en) | 2017-08-09 |
| US10450319B2 (en) | 2019-10-22 |
| KR20170055549A (ko) | 2017-05-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2697393C2 (ru) | Кристаллическая твердая форма соли бензолсульфоновой кислоты и 2-[(4S)-6-(4-хлорфенил)-1-метил-8-(метилокси)-4H-[1,2,4]триазоло[4,3-a][1,4]бензодиазепин-4-ил]-N-этилацетамида, способ ее получения и фармацевтическая композиция, содержащая ее | |
| DK2744809T3 (en) | 4- (8-methoxy-1 - ((1-methoxypropan-2-yl) -2- (tetrahydro-2H-pyran-4-yl) -1H-imidazo [4,5-c] quinolin-7-yl) -3,5-DIMETHYLISOXAZOLE AND ITS USE AS A BROMODOMINE INHIBITOR | |
| CA2981746C (en) | Maleate salts of a b-raf kinase inhibitor, crystalline forms, methods of preparation, and uses therefore | |
| TW200908983A (en) | Heterocyclic compounds and uses thereof | |
| TW201722431A (zh) | 吡咯并嘧啶激酶抑制劑之醫藥鹽、物理型式及組合物及彼等之製法 | |
| TW201024301A (en) | Amino pyrazole compound | |
| US10550101B2 (en) | Crystalline forms of mesylate salt of pyridinyl amino pyrimidine derivative, preparation methods therefor, and applications thereof | |
| KR102576964B1 (ko) | 헤테로시클리덴 아세트아미드 유도체의 결정 | |
| JP2018527363A (ja) | リナグリプチン結晶形及びこの製造方法 | |
| EP3191476B1 (en) | Tetrahydroquinoline derivatives as bromodomain inhibitors | |
| JP2020517626A (ja) | アセチルコリン受容体のモジュレーターとして有用な複素環化合物 | |
| TW201706259A (zh) | 結晶形式 | |
| TW201607925A (zh) | □啉化合物 | |
| TW201736352A (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 | |
| CN111372579A (zh) | 取代的苯基磺酰基苯基三唑硫酮和其用途 | |
| JP2023531078A (ja) | 化合物の結晶形態 | |
| KR20230031307A (ko) | P2x4 수용체 길항 활성을 갖는 치환된 n-페닐아세트아미드 | |
| WO2017012771A1 (en) | Crystalline filgotinib sulfonic acid addition salts | |
| WO2026002248A1 (zh) | 作为v2受体拮抗剂的苯并氮杂卓并环衍生物 | |
| CN115784986A (zh) | 一种hdac6抑制剂及其制备方法和应用 | |
| BR112019013292B1 (pt) | Polimorfos anidratos cristalinos, polimorfo triidrato cristalino, composições farmacêuticas, processo para preparar um polimorfo cristalino e uso de um polimorfo cristalino | |
| HK1229802A (en) | 4-(8-methoxy-1-((1-methoxypropan-2-yl)-2-(tetrahydro-2h-pyran-4-yl)-1 h-imidazo[4,5-c]quinolin-7-yl)-3,5-dimethylisoxazole and its use as bromodomain inhibitor | |
| HK1229802A1 (en) | 4-(8-methoxy-1-((1-methoxypropan-2-yl)-2-(tetrahydro-2h-pyran-4-yl)-1 h-imidazo[4,5-c]quinolin-7-yl)-3,5-dimethylisoxazole and its use as bromodomain inhibitor | |
| NZ620263B2 (en) | 4-(8-methoxy-1-((1-methoxypropan-2-yl)-2-(tetrahydro-2h-pyran-4-yl)-1 h-imidazo[4,5-c]quinolin-7-yl)-3,5-dimethylisoxazole and its use as bromodomain inhibitor | |
| HK1193411B (en) | 4-(8-methoxy-1-((1-methoxypropan-2-yl)-2-(tetrahydro-2h-pyran-4-yl)-1 h-imidazo[4,5-c]quinolin-7-yl)-3,5-dimethylisoxazole and its use as bromodomain inhibitor |