CA2897400A1 - 3-(benzoimidazol-2-yl)-indazole inhibitors of the wnt signaling pathway and therapeutic uses thereof - Google Patents
3-(benzoimidazol-2-yl)-indazole inhibitors of the wnt signaling pathway and therapeutic uses thereof Download PDFInfo
- Publication number
- CA2897400A1 CA2897400A1 CA2897400A CA2897400A CA2897400A1 CA 2897400 A1 CA2897400 A1 CA 2897400A1 CA 2897400 A CA2897400 A CA 2897400A CA 2897400 A CA2897400 A CA 2897400A CA 2897400 A1 CA2897400 A1 CA 2897400A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- group
- cancer
- compound
- disease
- 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.)
- Abandoned
Links
- 239000003112 inhibitor Substances 0.000 title description 16
- 230000004156 Wnt signaling pathway Effects 0.000 title description 6
- 230000001225 therapeutic effect Effects 0.000 title description 6
- JTKFRFMSUBOCIQ-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-1h-indazole Chemical compound C1=CC=C2C(C=3NC4=CC=CC=C4N=3)=NNC2=C1 JTKFRFMSUBOCIQ-UHFFFAOYSA-N 0.000 title description 2
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 128
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 124
- 201000011510 cancer Diseases 0.000 claims abstract description 84
- 238000000034 method Methods 0.000 claims abstract description 81
- 201000010099 disease Diseases 0.000 claims abstract description 71
- -1 indazole compound Chemical class 0.000 claims abstract description 58
- 102000013814 Wnt Human genes 0.000 claims abstract description 56
- 108050003627 Wnt Proteins 0.000 claims abstract description 56
- 208000035475 disorder Diseases 0.000 claims abstract description 53
- 230000011664 signaling Effects 0.000 claims abstract description 20
- 230000037361 pathway Effects 0.000 claims abstract description 19
- 201000008482 osteoarthritis Diseases 0.000 claims abstract description 12
- 230000000926 neurological effect Effects 0.000 claims abstract description 11
- 208000019693 Lung disease Diseases 0.000 claims abstract description 10
- 230000033115 angiogenesis Effects 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims description 208
- 125000000217 alkyl group Chemical group 0.000 claims description 86
- 229910052739 hydrogen Inorganic materials 0.000 claims description 74
- 125000001424 substituent group Chemical group 0.000 claims description 55
- 150000004820 halides Chemical class 0.000 claims description 48
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 46
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 43
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 43
- 150000003839 salts Chemical class 0.000 claims description 34
- 125000000623 heterocyclic group Chemical group 0.000 claims description 33
- 210000004027 cell Anatomy 0.000 claims description 32
- 125000001072 heteroaryl group Chemical group 0.000 claims description 30
- 208000011580 syndromic disease Diseases 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 17
- 230000000694 effects Effects 0.000 claims description 17
- 206010025323 Lymphomas Diseases 0.000 claims description 15
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 15
- 206010016654 Fibrosis Diseases 0.000 claims description 14
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 14
- 206010009944 Colon cancer Diseases 0.000 claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 13
- 208000005069 pulmonary fibrosis Diseases 0.000 claims description 13
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 13
- 210000000988 bone and bone Anatomy 0.000 claims description 12
- 230000004761 fibrosis Effects 0.000 claims description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 11
- 206010039491 Sarcoma Diseases 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 208000008383 Wilms tumor Diseases 0.000 claims description 10
- 206010033128 Ovarian cancer Diseases 0.000 claims description 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 201000001441 melanoma Diseases 0.000 claims description 9
- 201000008026 nephroblastoma Diseases 0.000 claims description 9
- 201000010193 neural tube defect Diseases 0.000 claims description 9
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 8
- 206010006187 Breast cancer Diseases 0.000 claims description 8
- 208000026310 Breast neoplasm Diseases 0.000 claims description 8
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 8
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 8
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 8
- 201000010769 Prader-Willi syndrome Diseases 0.000 claims description 8
- 208000006289 Rett Syndrome Diseases 0.000 claims description 8
- 206010039710 Scleroderma Diseases 0.000 claims description 8
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 8
- 208000029742 colonic neoplasm Diseases 0.000 claims description 8
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 8
- 208000020816 lung neoplasm Diseases 0.000 claims description 8
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 7
- 208000009575 Angelman syndrome Diseases 0.000 claims description 7
- 201000000046 Beckwith-Wiedemann syndrome Diseases 0.000 claims description 7
- 208000020084 Bone disease Diseases 0.000 claims description 7
- 208000026010 Caudal duplication Diseases 0.000 claims description 7
- 208000006586 Ectromelia Diseases 0.000 claims description 7
- 208000028506 Familial Exudative Vitreoretinopathies Diseases 0.000 claims description 7
- 208000001914 Fragile X syndrome Diseases 0.000 claims description 7
- 208000008875 Fuhrmann syndrome Diseases 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- 208000033321 ICF syndrome Diseases 0.000 claims description 7
- 206010024503 Limb reduction defect Diseases 0.000 claims description 7
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 7
- 208000025464 Norrie disease Diseases 0.000 claims description 7
- 208000008589 Obesity Diseases 0.000 claims description 7
- 208000022617 SERKAL syndrome Diseases 0.000 claims description 7
- 206010072610 Skeletal dysplasia Diseases 0.000 claims description 7
- 208000000453 Skin Neoplasms Diseases 0.000 claims description 7
- 206010047486 Virilism Diseases 0.000 claims description 7
- 201000006288 alpha thalassemia Diseases 0.000 claims description 7
- 208000015100 cartilage disease Diseases 0.000 claims description 7
- 208000029404 congenital absence of upper arm and forearm with hand present Diseases 0.000 claims description 7
- 208000029078 coronary artery disease Diseases 0.000 claims description 7
- 201000006902 exudative vitreoretinopathy Diseases 0.000 claims description 7
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims description 7
- 201000005202 lung cancer Diseases 0.000 claims description 7
- 235000020824 obesity Nutrition 0.000 claims description 7
- 108090000623 proteins and genes Proteins 0.000 claims description 7
- 230000004263 retinal angiogenesis Effects 0.000 claims description 7
- 208000035581 susceptibility to neural tube defects Diseases 0.000 claims description 7
- 201000006680 tooth agenesis Diseases 0.000 claims description 7
- 201000008251 Focal dermal hypoplasia Diseases 0.000 claims description 6
- 208000007766 Kaposi sarcoma Diseases 0.000 claims description 6
- 208000001089 Multiple system atrophy Diseases 0.000 claims description 6
- 108091000080 Phosphotransferase Proteins 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- 201000006417 multiple sclerosis Diseases 0.000 claims description 6
- 201000001937 osteoporosis-pseudoglioma syndrome Diseases 0.000 claims description 6
- 102000020233 phosphotransferase Human genes 0.000 claims description 6
- 201000000849 skin cancer Diseases 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims description 5
- 208000018084 Bone neoplasm Diseases 0.000 claims description 5
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 5
- 208000034578 Multiple myelomas Diseases 0.000 claims description 5
- 208000007758 Odonto-onycho-dermal dysplasia Diseases 0.000 claims description 5
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 5
- 208000029664 classic familial adenomatous polyposis Diseases 0.000 claims description 5
- 201000008968 osteosarcoma Diseases 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 125000006545 (C1-C9) alkyl group Chemical group 0.000 claims description 4
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims description 4
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims description 4
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 4
- 206010003805 Autism Diseases 0.000 claims description 4
- 208000020706 Autistic disease Diseases 0.000 claims description 4
- 206010005949 Bone cancer Diseases 0.000 claims description 4
- 206010014733 Endometrial cancer Diseases 0.000 claims description 4
- 206010014759 Endometrial neoplasm Diseases 0.000 claims description 4
- 208000006168 Ewing Sarcoma Diseases 0.000 claims description 4
- 206010018364 Glomerulonephritis Diseases 0.000 claims description 4
- 208000017604 Hodgkin disease Diseases 0.000 claims description 4
- 208000021519 Hodgkin lymphoma Diseases 0.000 claims description 4
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims description 4
- 206010027476 Metastases Diseases 0.000 claims description 4
- 208000021642 Muscular disease Diseases 0.000 claims description 4
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 4
- 206010029260 Neuroblastoma Diseases 0.000 claims description 4
- 206010031127 Orthostatic hypotension Diseases 0.000 claims description 4
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 4
- 208000018737 Parkinson disease Diseases 0.000 claims description 4
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims description 4
- 208000024777 Prion disease Diseases 0.000 claims description 4
- 208000002158 Proliferative Vitreoretinopathy Diseases 0.000 claims description 4
- 206010060862 Prostate cancer Diseases 0.000 claims description 4
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 4
- 201000000582 Retinoblastoma Diseases 0.000 claims description 4
- 206010038934 Retinopathy proliferative Diseases 0.000 claims description 4
- 208000024313 Testicular Neoplasms Diseases 0.000 claims description 4
- 210000004556 brain Anatomy 0.000 claims description 4
- 208000006990 cholangiocarcinoma Diseases 0.000 claims description 4
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 4
- 230000003176 fibrotic effect Effects 0.000 claims description 4
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 4
- 230000009401 metastasis Effects 0.000 claims description 4
- 208000021971 neovascular inflammatory vitreoretinopathy Diseases 0.000 claims description 4
- 201000001119 neuropathy Diseases 0.000 claims description 4
- 230000007823 neuropathy Effects 0.000 claims description 4
- 201000002528 pancreatic cancer Diseases 0.000 claims description 4
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 4
- 230000000750 progressive effect Effects 0.000 claims description 4
- 201000002212 progressive supranuclear palsy Diseases 0.000 claims description 4
- 230000006785 proliferative vitreoretinopathy Effects 0.000 claims description 4
- 208000037803 restenosis Diseases 0.000 claims description 4
- 201000009410 rhabdomyosarcoma Diseases 0.000 claims description 4
- 206010062261 spinal cord neoplasm Diseases 0.000 claims description 4
- 201000003251 split hand-foot malformation Diseases 0.000 claims description 4
- 206010061424 Anal cancer Diseases 0.000 claims description 3
- 208000007860 Anus Neoplasms Diseases 0.000 claims description 3
- 206010003694 Atrophy Diseases 0.000 claims description 3
- 206010004593 Bile duct cancer Diseases 0.000 claims description 3
- 206010005003 Bladder cancer Diseases 0.000 claims description 3
- 208000003174 Brain Neoplasms Diseases 0.000 claims description 3
- 206010007279 Carcinoid tumour of the gastrointestinal tract Diseases 0.000 claims description 3
- 206010008342 Cervix carcinoma Diseases 0.000 claims description 3
- 208000010693 Charcot-Marie-Tooth Disease Diseases 0.000 claims description 3
- 208000011990 Corticobasal Degeneration Diseases 0.000 claims description 3
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 3
- 208000000461 Esophageal Neoplasms Diseases 0.000 claims description 3
- 201000011240 Frontotemporal dementia Diseases 0.000 claims description 3
- 208000022072 Gallbladder Neoplasms Diseases 0.000 claims description 3
- 206010051066 Gastrointestinal stromal tumour Diseases 0.000 claims description 3
- 208000023105 Huntington disease Diseases 0.000 claims description 3
- 206010021042 Hypopharyngeal cancer Diseases 0.000 claims description 3
- 206010056305 Hypopharyngeal neoplasm Diseases 0.000 claims description 3
- 208000008839 Kidney Neoplasms Diseases 0.000 claims description 3
- 206010023825 Laryngeal cancer Diseases 0.000 claims description 3
- 201000002832 Lewy body dementia Diseases 0.000 claims description 3
- 208000032271 Malignant tumor of penis Diseases 0.000 claims description 3
- 208000033833 Myelomonocytic Chronic Leukemia Diseases 0.000 claims description 3
- 201000009623 Myopathy Diseases 0.000 claims description 3
- 208000001894 Nasopharyngeal Neoplasms Diseases 0.000 claims description 3
- 206010061306 Nasopharyngeal cancer Diseases 0.000 claims description 3
- 208000002471 Penile Neoplasms Diseases 0.000 claims description 3
- 206010034299 Penile cancer Diseases 0.000 claims description 3
- 208000007913 Pituitary Neoplasms Diseases 0.000 claims description 3
- 206010038389 Renal cancer Diseases 0.000 claims description 3
- 208000004337 Salivary Gland Neoplasms Diseases 0.000 claims description 3
- 206010061934 Salivary gland cancer Diseases 0.000 claims description 3
- 208000005718 Stomach Neoplasms Diseases 0.000 claims description 3
- 206010057644 Testis cancer Diseases 0.000 claims description 3
- 208000000728 Thymus Neoplasms Diseases 0.000 claims description 3
- 208000024770 Thyroid neoplasm Diseases 0.000 claims description 3
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 3
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 3
- 206010047741 Vulval cancer Diseases 0.000 claims description 3
- 208000004354 Vulvar Neoplasms Diseases 0.000 claims description 3
- 102000052547 Wnt-1 Human genes 0.000 claims description 3
- 230000001919 adrenal effect Effects 0.000 claims description 3
- 201000011165 anus cancer Diseases 0.000 claims description 3
- 230000037444 atrophy Effects 0.000 claims description 3
- 208000026900 bile duct neoplasm Diseases 0.000 claims description 3
- 210000003169 central nervous system Anatomy 0.000 claims description 3
- 201000010881 cervical cancer Diseases 0.000 claims description 3
- 201000010902 chronic myelomonocytic leukemia Diseases 0.000 claims description 3
- 230000001054 cortical effect Effects 0.000 claims description 3
- 201000004101 esophageal cancer Diseases 0.000 claims description 3
- 208000024519 eye neoplasm Diseases 0.000 claims description 3
- 201000010175 gallbladder cancer Diseases 0.000 claims description 3
- 201000011243 gastrointestinal stromal tumor Diseases 0.000 claims description 3
- 208000003884 gestational trophoblastic disease Diseases 0.000 claims description 3
- 201000006866 hypopharynx cancer Diseases 0.000 claims description 3
- 201000008319 inclusion body myositis Diseases 0.000 claims description 3
- 201000010982 kidney cancer Diseases 0.000 claims description 3
- 206010023841 laryngeal neoplasm Diseases 0.000 claims description 3
- 201000000083 maturity-onset diabetes of the young type 1 Diseases 0.000 claims description 3
- 230000002503 metabolic effect Effects 0.000 claims description 3
- 208000010125 myocardial infarction Diseases 0.000 claims description 3
- 201000008106 ocular cancer Diseases 0.000 claims description 3
- 102000004169 proteins and genes Human genes 0.000 claims description 3
- 201000002314 small intestine cancer Diseases 0.000 claims description 3
- 230000009885 systemic effect Effects 0.000 claims description 3
- 201000003120 testicular cancer Diseases 0.000 claims description 3
- 208000022345 tetraamelia syndrome Diseases 0.000 claims description 3
- 229930192474 thiophene Chemical group 0.000 claims description 3
- 201000009377 thymus cancer Diseases 0.000 claims description 3
- 201000002510 thyroid cancer Diseases 0.000 claims description 3
- 201000005112 urinary bladder cancer Diseases 0.000 claims description 3
- 208000037965 uterine sarcoma Diseases 0.000 claims description 3
- 206010046885 vaginal cancer Diseases 0.000 claims description 3
- 208000013139 vaginal neoplasm Diseases 0.000 claims description 3
- 201000005102 vulva cancer Diseases 0.000 claims description 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 2
- 101100317380 Danio rerio wnt4a gene Proteins 0.000 claims description 2
- 206010067889 Dementia with Lewy bodies Diseases 0.000 claims description 2
- 201000009273 Endometriosis Diseases 0.000 claims description 2
- 101000814371 Homo sapiens Protein Wnt-10a Proteins 0.000 claims description 2
- 101000770799 Homo sapiens Protein Wnt-10b Proteins 0.000 claims description 2
- 101000781981 Homo sapiens Protein Wnt-11 Proteins 0.000 claims description 2
- 101000804728 Homo sapiens Protein Wnt-2b Proteins 0.000 claims description 2
- 101000804804 Homo sapiens Protein Wnt-5b Proteins 0.000 claims description 2
- 101000855002 Homo sapiens Protein Wnt-6 Proteins 0.000 claims description 2
- 101000855004 Homo sapiens Protein Wnt-7a Proteins 0.000 claims description 2
- 101000814380 Homo sapiens Protein Wnt-7b Proteins 0.000 claims description 2
- 101000814350 Homo sapiens Protein Wnt-8a Proteins 0.000 claims description 2
- 101000650149 Homo sapiens Protein Wnt-8b Proteins 0.000 claims description 2
- 101000650117 Homo sapiens Protein Wnt-9a Proteins 0.000 claims description 2
- 101000650119 Homo sapiens Protein Wnt-9b Proteins 0.000 claims description 2
- 101000781955 Homo sapiens Proto-oncogene Wnt-1 Proteins 0.000 claims description 2
- 101000954762 Homo sapiens Proto-oncogene Wnt-3 Proteins 0.000 claims description 2
- 208000029523 Interstitial Lung disease Diseases 0.000 claims description 2
- 206010023421 Kidney fibrosis Diseases 0.000 claims description 2
- 206010048654 Muscle fibrosis Diseases 0.000 claims description 2
- 102100039461 Protein Wnt-10a Human genes 0.000 claims description 2
- 102100029062 Protein Wnt-10b Human genes 0.000 claims description 2
- 102100036567 Protein Wnt-11 Human genes 0.000 claims description 2
- 102100035289 Protein Wnt-2b Human genes 0.000 claims description 2
- 102100035331 Protein Wnt-5b Human genes 0.000 claims description 2
- 102100020732 Protein Wnt-6 Human genes 0.000 claims description 2
- 102100020729 Protein Wnt-7a Human genes 0.000 claims description 2
- 102100039470 Protein Wnt-7b Human genes 0.000 claims description 2
- 102100039453 Protein Wnt-8a Human genes 0.000 claims description 2
- 102100027542 Protein Wnt-8b Human genes 0.000 claims description 2
- 102100027503 Protein Wnt-9a Human genes 0.000 claims description 2
- 102100027502 Protein Wnt-9b Human genes 0.000 claims description 2
- 208000032056 Radiation Fibrosis Syndrome Diseases 0.000 claims description 2
- 206010067953 Radiation fibrosis Diseases 0.000 claims description 2
- 206010050207 Skin fibrosis Diseases 0.000 claims description 2
- 206010067269 Uterine fibrosis Diseases 0.000 claims description 2
- 101150010310 WNT-4 gene Proteins 0.000 claims description 2
- 101150019524 WNT2 gene Proteins 0.000 claims description 2
- 102000052556 Wnt-2 Human genes 0.000 claims description 2
- 108700020986 Wnt-2 Proteins 0.000 claims description 2
- 102000052549 Wnt-3 Human genes 0.000 claims description 2
- 102000052548 Wnt-4 Human genes 0.000 claims description 2
- 108700020984 Wnt-4 Proteins 0.000 claims description 2
- 102000044880 Wnt3A Human genes 0.000 claims description 2
- 108700013515 Wnt3A Proteins 0.000 claims description 2
- 101100485099 Xenopus laevis wnt2b-b gene Proteins 0.000 claims description 2
- 230000007882 cirrhosis Effects 0.000 claims description 2
- 230000003412 degenerative effect Effects 0.000 claims description 2
- 230000002124 endocrine Effects 0.000 claims description 2
- 206010061989 glomerulosclerosis Diseases 0.000 claims description 2
- 230000001969 hypertrophic effect Effects 0.000 claims description 2
- 208000023589 ischemic disease Diseases 0.000 claims description 2
- 210000004185 liver Anatomy 0.000 claims description 2
- 201000002793 renal fibrosis Diseases 0.000 claims description 2
- 230000036573 scar formation Effects 0.000 claims description 2
- 230000037390 scarring Effects 0.000 claims description 2
- 101150068520 wnt3a gene Proteins 0.000 claims description 2
- 101000781950 Homo sapiens Protein Wnt-16 Proteins 0.000 claims 1
- 101000804792 Homo sapiens Protein Wnt-5a Proteins 0.000 claims 1
- 102100036587 Protein Wnt-16 Human genes 0.000 claims 1
- 102000043366 Wnt-5a Human genes 0.000 claims 1
- 230000004663 cell proliferation Effects 0.000 abstract description 15
- 238000011282 treatment Methods 0.000 abstract description 14
- 208000024827 Alzheimer disease Diseases 0.000 abstract description 11
- 230000035772 mutation Effects 0.000 abstract description 10
- 208000026350 Inborn Genetic disease Diseases 0.000 abstract description 8
- 208000016361 genetic disease Diseases 0.000 abstract description 8
- 230000001404 mediated effect Effects 0.000 abstract description 7
- 230000002159 abnormal effect Effects 0.000 abstract description 6
- 230000004913 activation Effects 0.000 abstract description 4
- 230000008482 dysregulation Effects 0.000 abstract description 3
- 230000001413 cellular effect Effects 0.000 abstract description 2
- 150000002473 indoazoles Chemical class 0.000 abstract 1
- 230000007170 pathology Effects 0.000 abstract 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 149
- 239000000203 mixture Substances 0.000 description 114
- 238000005160 1H NMR spectroscopy Methods 0.000 description 84
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 65
- 239000000243 solution Substances 0.000 description 53
- 239000007787 solid Substances 0.000 description 50
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 42
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 31
- 235000002639 sodium chloride Nutrition 0.000 description 31
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 29
- 241000282412 Homo Species 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- 239000003814 drug Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
- 229940079593 drug Drugs 0.000 description 14
- 239000007788 liquid Substances 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 13
- 239000002552 dosage form Substances 0.000 description 13
- 238000001802 infusion Methods 0.000 description 13
- 238000001990 intravenous administration Methods 0.000 description 13
- 239000002245 particle Substances 0.000 description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 13
- ILGTYHMEQSSHFG-UHFFFAOYSA-N 5-bromo-2h-indazole-3-carbaldehyde Chemical compound C1=C(Br)C=CC2=NNC(C=O)=C21 ILGTYHMEQSSHFG-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
- 239000000543 intermediate Substances 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 101150041968 CDC13 gene Proteins 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 206010061246 Intervertebral disc degeneration Diseases 0.000 description 10
- 239000004698 Polyethylene Substances 0.000 description 10
- 238000002512 chemotherapy Methods 0.000 description 10
- 208000018180 degenerative disc disease Diseases 0.000 description 10
- 208000021600 intervertebral disc degenerative disease Diseases 0.000 description 10
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 201000009030 Carcinoma Diseases 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 208000009956 adenocarcinoma Diseases 0.000 description 9
- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 8
- SKBVDALUQYAFSP-UHFFFAOYSA-N 5-bromo-1-(2-trimethylsilylethoxymethyl)indazole-3-carbaldehyde Chemical compound BrC1=CC=C2N(COCC[Si](C)(C)C)N=C(C=O)C2=C1 SKBVDALUQYAFSP-UHFFFAOYSA-N 0.000 description 8
- 239000007832 Na2SO4 Substances 0.000 description 8
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000001594 aberrant effect Effects 0.000 description 8
- UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 8
- 235000017550 sodium carbonate Nutrition 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- 206010012689 Diabetic retinopathy Diseases 0.000 description 7
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 7
- 208000036142 Viral infection Diseases 0.000 description 7
- 239000013543 active substance Substances 0.000 description 7
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- MBAPRVODHSSHJA-UHFFFAOYSA-N n-(2-bromo-6-nitrophenyl)acetamide Chemical compound CC(=O)NC1=C(Br)C=CC=C1[N+]([O-])=O MBAPRVODHSSHJA-UHFFFAOYSA-N 0.000 description 7
- IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 description 7
- 239000008247 solid mixture Substances 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- 230000009385 viral infection Effects 0.000 description 7
- BSHKOIWZXZNENI-UHFFFAOYSA-N 3-(4-methylpiperazin-1-yl)benzene-1,2-diamine Chemical compound C1CN(C)CCN1C1=CC=CC(N)=C1N BSHKOIWZXZNENI-UHFFFAOYSA-N 0.000 description 6
- YADOEPHJIBKBCN-UHFFFAOYSA-N 3-chloro-2-nitroaniline Chemical compound NC1=CC=CC(Cl)=C1[N+]([O-])=O YADOEPHJIBKBCN-UHFFFAOYSA-N 0.000 description 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000000443 aerosol Substances 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 239000000084 colloidal system Substances 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 230000007547 defect Effects 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 229960002949 fluorouracil Drugs 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 125000001188 haloalkyl group Chemical group 0.000 description 6
- 230000002262 irrigation Effects 0.000 description 6
- 238000003973 irrigation Methods 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 206010039073 rheumatoid arthritis Diseases 0.000 description 6
- 208000024891 symptom Diseases 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- OQUHYNMITHDQLD-UHFFFAOYSA-N (5-bromopyridin-3-yl)methanamine Chemical compound NCC1=CN=CC(Br)=C1 OQUHYNMITHDQLD-UHFFFAOYSA-N 0.000 description 5
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 5
- VWSGKVYQLVXORK-UHFFFAOYSA-N 3-piperidin-1-ylbenzene-1,2-diamine Chemical compound NC1=CC=CC(N2CCCCC2)=C1N VWSGKVYQLVXORK-UHFFFAOYSA-N 0.000 description 5
- IBXWZWVVMSKAQO-UHFFFAOYSA-N 3-pyridin-4-ylbenzene-1,2-diamine Chemical compound NC1=CC=CC(C=2C=CN=CC=2)=C1N IBXWZWVVMSKAQO-UHFFFAOYSA-N 0.000 description 5
- NGUVGKAEOFPLDT-UHFFFAOYSA-N 5-bromopyridine-3-carbaldehyde Chemical compound BrC1=CN=CC(C=O)=C1 NGUVGKAEOFPLDT-UHFFFAOYSA-N 0.000 description 5
- VVIAGPKUTFNRDU-UHFFFAOYSA-N 6S-folinic acid Natural products C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-UHFFFAOYSA-N 0.000 description 5
- 201000004681 Psoriasis Diseases 0.000 description 5
- 206010040047 Sepsis Diseases 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 210000001188 articular cartilage Anatomy 0.000 description 5
- 230000004071 biological effect Effects 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- NXWBOAQGGZVKBT-UHFFFAOYSA-N cyclobutanecarboxamide Chemical compound NC(=O)C1C[CH]C1 NXWBOAQGGZVKBT-UHFFFAOYSA-N 0.000 description 5
- 239000003937 drug carrier Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 238000003818 flash chromatography Methods 0.000 description 5
- VVIAGPKUTFNRDU-ABLWVSNPSA-N folinic acid Chemical compound C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-ABLWVSNPSA-N 0.000 description 5
- 235000008191 folinic acid Nutrition 0.000 description 5
- 239000011672 folinic acid Substances 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 description 5
- 229960001101 ifosfamide Drugs 0.000 description 5
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 229960004768 irinotecan Drugs 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 229940047889 isobutyramide Drugs 0.000 description 5
- 229960001691 leucovorin Drugs 0.000 description 5
- 208000032839 leukemia Diseases 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 235000015320 potassium carbonate Nutrition 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 230000002685 pulmonary effect Effects 0.000 description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 206010041823 squamous cell carcinoma Diseases 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000000829 suppository Substances 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- GYUURHMITDQTRU-UHFFFAOYSA-N tributyl(pyridin-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CC=N1 GYUURHMITDQTRU-UHFFFAOYSA-N 0.000 description 5
- WDVDHJLKXYCOFS-UHFFFAOYSA-N (5-bromopyridin-3-yl)methanol Chemical compound OCC1=CN=CC(Br)=C1 WDVDHJLKXYCOFS-UHFFFAOYSA-N 0.000 description 4
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 4
- WMYLGFXZYBIYCO-UHFFFAOYSA-N 2-nitro-6-pyridin-2-ylaniline Chemical compound C1=CC=C([N+]([O-])=O)C(N)=C1C1=CC=CC=N1 WMYLGFXZYBIYCO-UHFFFAOYSA-N 0.000 description 4
- ORIMPJHDGVFITH-UHFFFAOYSA-N 5-bromo-n,n-dimethylpyridin-3-amine Chemical compound CN(C)C1=CN=CC(Br)=C1 ORIMPJHDGVFITH-UHFFFAOYSA-N 0.000 description 4
- WDFUQQIAZCINSW-UHFFFAOYSA-N 5-bromo-n-propan-2-ylpyridin-3-amine Chemical compound CC(C)NC1=CN=CC(Br)=C1 WDFUQQIAZCINSW-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 4
- 208000032612 Glial tumor Diseases 0.000 description 4
- 206010018338 Glioma Diseases 0.000 description 4
- 206010063491 Herpes zoster oticus Diseases 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 206010024612 Lipoma Diseases 0.000 description 4
- 102000001253 Protein Kinase Human genes 0.000 description 4
- 208000028977 Tetra-amelia Diseases 0.000 description 4
- 125000003368 amide group Chemical group 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 230000037182 bone density Effects 0.000 description 4
- 125000001246 bromo group Chemical group Br* 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 235000010980 cellulose Nutrition 0.000 description 4
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 4
- 229960004316 cisplatin Drugs 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- OJEYDZBIAYMFFD-UHFFFAOYSA-N cyclopentanecarboxamide Chemical compound NC(=O)C1C[CH]CC1 OJEYDZBIAYMFFD-UHFFFAOYSA-N 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 210000003027 ear inner Anatomy 0.000 description 4
- 210000000959 ear middle Anatomy 0.000 description 4
- VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 description 4
- 230000012010 growth Effects 0.000 description 4
- 230000000670 limiting effect Effects 0.000 description 4
- 239000002502 liposome Substances 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 210000004379 membrane Anatomy 0.000 description 4
- VPTYUALSWZYJMJ-UHFFFAOYSA-N n-(2-nitro-6-pyridin-2-ylphenyl)acetamide Chemical compound C1=CC=C([N+]([O-])=O)C(NC(=O)C)=C1C1=CC=CC=N1 VPTYUALSWZYJMJ-UHFFFAOYSA-N 0.000 description 4
- AUOGSVYXEUVRBF-UHFFFAOYSA-N n-(2-nitro-6-pyridin-4-ylphenyl)acetamide Chemical compound C1=CC=C([N+]([O-])=O)C(NC(=O)C)=C1C1=CC=NC=C1 AUOGSVYXEUVRBF-UHFFFAOYSA-N 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- DWAFYCQODLXJNR-BNTLRKBRSA-L oxaliplatin Chemical compound O1C(=O)C(=O)O[Pt]11N[C@@H]2CCCC[C@H]2N1 DWAFYCQODLXJNR-BNTLRKBRSA-L 0.000 description 4
- 229960001756 oxaliplatin Drugs 0.000 description 4
- 125000004193 piperazinyl group Chemical group 0.000 description 4
- 125000003386 piperidinyl group Chemical group 0.000 description 4
- XIPFMBOWZXULIA-UHFFFAOYSA-N pivalamide Chemical compound CC(C)(C)C(N)=O XIPFMBOWZXULIA-UHFFFAOYSA-N 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 108060006633 protein kinase Proteins 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 210000001519 tissue Anatomy 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- 210000004881 tumor cell Anatomy 0.000 description 4
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 4
- 230000007556 vascular defect Effects 0.000 description 4
- QCSLIRFWJPOENV-UHFFFAOYSA-N (2-fluorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1F QCSLIRFWJPOENV-UHFFFAOYSA-N 0.000 description 3
- LDEBJWHBKRIOEO-UHFFFAOYSA-N 2-[(5-bromopyridin-3-yl)methyl]isoindole-1,3-dione Chemical compound BrC1=CN=CC(CN2C(C3=CC=CC=C3C2=O)=O)=C1 LDEBJWHBKRIOEO-UHFFFAOYSA-N 0.000 description 3
- AOPBDRUWRLBSDB-UHFFFAOYSA-N 2-bromoaniline Chemical compound NC1=CC=CC=C1Br AOPBDRUWRLBSDB-UHFFFAOYSA-N 0.000 description 3
- SOSPMXMEOFGPIM-UHFFFAOYSA-N 3,5-dibromopyridine Chemical compound BrC1=CN=CC(Br)=C1 SOSPMXMEOFGPIM-UHFFFAOYSA-N 0.000 description 3
- WNBWDKYEMUVQMK-UHFFFAOYSA-N 3-(furan-3-yl)benzene-1,2-diamine Chemical compound NC1=CC=CC(C2=COC=C2)=C1N WNBWDKYEMUVQMK-UHFFFAOYSA-N 0.000 description 3
- LGYZVEGWRNLSHA-UHFFFAOYSA-N 3-pyridin-2-ylbenzene-1,2-diamine Chemical compound NC1=CC=CC(C=2N=CC=CC=2)=C1N LGYZVEGWRNLSHA-UHFFFAOYSA-N 0.000 description 3
- JLESUFOUYVCKQG-UHFFFAOYSA-N 3-pyridin-3-ylbenzene-1,2-diamine Chemical compound NC1=CC=CC(C=2C=NC=CC=2)=C1N JLESUFOUYVCKQG-UHFFFAOYSA-N 0.000 description 3
- JRVCQXXLHYYLLU-UHFFFAOYSA-N 3-thiophen-3-ylbenzene-1,2-diamine Chemical compound NC1=CC=CC(C2=CSC=C2)=C1N JRVCQXXLHYYLLU-UHFFFAOYSA-N 0.000 description 3
- MDQXGHBCDCOOSM-UHFFFAOYSA-N 5-bromopyridin-3-amine Chemical compound NC1=CN=CC(Br)=C1 MDQXGHBCDCOOSM-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 108091007914 CDKs Proteins 0.000 description 3
- 101100314454 Caenorhabditis elegans tra-1 gene Proteins 0.000 description 3
- GAGWJHPBXLXJQN-UORFTKCHSA-N Capecitabine Chemical compound C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](C)O1 GAGWJHPBXLXJQN-UORFTKCHSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229920000858 Cyclodextrin Polymers 0.000 description 3
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 201000008808 Fibrosarcoma Diseases 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- 208000007465 Giant cell arteritis Diseases 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 229910004373 HOAc Inorganic materials 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 206010049567 Miller Fisher syndrome Diseases 0.000 description 3
- NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 3
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- 208000005225 Opsoclonus-Myoclonus Syndrome Diseases 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 208000005587 Refsum Disease Diseases 0.000 description 3
- 208000006011 Stroke Diseases 0.000 description 3
- 206010043276 Teratoma Diseases 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000008186 active pharmaceutical agent Substances 0.000 description 3
- 125000004423 acyloxy group Chemical group 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 210000003477 cochlea Anatomy 0.000 description 3
- 229940110456 cocoa butter Drugs 0.000 description 3
- 235000019868 cocoa butter Nutrition 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 238000012377 drug delivery Methods 0.000 description 3
- 229940088679 drug related substance Drugs 0.000 description 3
- SBNKFTQSBPKMBZ-UHFFFAOYSA-N ethenzamide Chemical compound CCOC1=CC=CC=C1C(N)=O SBNKFTQSBPKMBZ-UHFFFAOYSA-N 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 206010016629 fibroma Diseases 0.000 description 3
- XGALLCVXEZPNRQ-UHFFFAOYSA-N gefitinib Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 XGALLCVXEZPNRQ-UHFFFAOYSA-N 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 201000011349 geniculate herpes zoster Diseases 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 201000011066 hemangioma Diseases 0.000 description 3
- 201000005787 hematologic cancer Diseases 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- YLMAHDNUQAMNNX-UHFFFAOYSA-N imatinib methanesulfonate Chemical compound CS(O)(=O)=O.C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3N=C(C=CN=3)C=3C=NC=CC=3)C(C)=CC=2)C=C1 YLMAHDNUQAMNNX-UHFFFAOYSA-N 0.000 description 3
- 239000007943 implant Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- JPOXHFFVKGUQLD-UHFFFAOYSA-N n-(5-bromopyridin-3-yl)butanamide Chemical compound CCCC(=O)NC1=CN=CC(Br)=C1 JPOXHFFVKGUQLD-UHFFFAOYSA-N 0.000 description 3
- WMHLJVOMKSSRCJ-UHFFFAOYSA-N n-(5-bromopyridin-3-yl)cyclobutanecarboxamide Chemical compound BrC1=CN=CC(NC(=O)C2CCC2)=C1 WMHLJVOMKSSRCJ-UHFFFAOYSA-N 0.000 description 3
- OZRPEDYWQLEFPU-UHFFFAOYSA-N n-(5-bromopyridin-3-yl)cyclopropanecarboxamide Chemical compound BrC1=CN=CC(NC(=O)C2CC2)=C1 OZRPEDYWQLEFPU-UHFFFAOYSA-N 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 208000015122 neurodegenerative disease Diseases 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 208000015768 polyposis Diseases 0.000 description 3
- 229940002612 prodrug Drugs 0.000 description 3
- 239000000651 prodrug Substances 0.000 description 3
- 230000035755 proliferation Effects 0.000 description 3
- 108020003175 receptors Proteins 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
- 229960004641 rituximab Drugs 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000012453 solvate Substances 0.000 description 3
- 208000002320 spinal muscular atrophy Diseases 0.000 description 3
- 208000029277 split foot Diseases 0.000 description 3
- 208000028882 split hand Diseases 0.000 description 3
- 210000000130 stem cell Anatomy 0.000 description 3
- 238000001356 surgical procedure Methods 0.000 description 3
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 3
- CBWYSCPCEBNERR-UHFFFAOYSA-N tert-butyl n-[(5-bromopyridin-3-yl)methyl]-n-(cyclopentylmethyl)carbamate Chemical compound C=1N=CC(Br)=CC=1CN(C(=O)OC(C)(C)C)CC1CCCC1 CBWYSCPCEBNERR-UHFFFAOYSA-N 0.000 description 3
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 2
- NADISAHJKHXYNS-UHFFFAOYSA-N 2-nitro-3-piperidin-1-ylaniline Chemical compound NC1=CC=CC(N2CCCCC2)=C1[N+]([O-])=O NADISAHJKHXYNS-UHFFFAOYSA-N 0.000 description 2
- GLKHLBAXHLAQBJ-UHFFFAOYSA-N 3-bromo-2-nitroaniline Chemical compound NC1=CC=CC(Br)=C1[N+]([O-])=O GLKHLBAXHLAQBJ-UHFFFAOYSA-N 0.000 description 2
- ZFVCJTZTBBYGPO-UHFFFAOYSA-N 3-bromo-5-(piperidin-1-ylmethyl)pyridine Chemical compound BrC1=CN=CC(CN2CCCCC2)=C1 ZFVCJTZTBBYGPO-UHFFFAOYSA-N 0.000 description 2
- UAZLPRVDXABSND-UHFFFAOYSA-N 3-bromo-5-(pyrrolidin-1-ylmethyl)pyridine Chemical compound BrC1=CN=CC(CN2CCCC2)=C1 UAZLPRVDXABSND-UHFFFAOYSA-N 0.000 description 2
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- 108010012934 Albumin-Bound Paclitaxel Proteins 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 201000003076 Angiosarcoma Diseases 0.000 description 2
- 208000032467 Aplastic anaemia Diseases 0.000 description 2
- 201000001320 Atherosclerosis Diseases 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- 208000003170 Bronchiolo-Alveolar Adenocarcinoma Diseases 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- GAGWJHPBXLXJQN-UHFFFAOYSA-N Capecitabine Natural products C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1C1C(O)C(O)C(C)O1 GAGWJHPBXLXJQN-UHFFFAOYSA-N 0.000 description 2
- 241000283707 Capra Species 0.000 description 2
- 201000003728 Centronuclear myopathy Diseases 0.000 description 2
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 description 2
- 208000030939 Chronic inflammatory demyelinating polyneuropathy Diseases 0.000 description 2
- 208000023890 Complex Regional Pain Syndromes Diseases 0.000 description 2
- 208000009283 Craniosynostoses Diseases 0.000 description 2
- 206010049889 Craniosynostosis Diseases 0.000 description 2
- 208000014311 Cushing syndrome Diseases 0.000 description 2
- 102000016736 Cyclin Human genes 0.000 description 2
- 108050006400 Cyclin Proteins 0.000 description 2
- 102000003903 Cyclin-dependent kinases Human genes 0.000 description 2
- 108090000266 Cyclin-dependent kinases Proteins 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 208000004986 Diffuse Cerebral Sclerosis of Schilder Diseases 0.000 description 2
- 206010067557 Dysmetropsia Diseases 0.000 description 2
- 206010058314 Dysplasia Diseases 0.000 description 2
- 241000792859 Enema Species 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- 208000007659 Fibroadenoma Diseases 0.000 description 2
- 108090000331 Firefly luciferases Proteins 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 208000010055 Globoid Cell Leukodystrophy Diseases 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 208000002927 Hamartoma Diseases 0.000 description 2
- 208000001258 Hemangiosarcoma Diseases 0.000 description 2
- 101001043594 Homo sapiens Low-density lipoprotein receptor-related protein 5 Proteins 0.000 description 2
- 241000701044 Human gammaherpesvirus 4 Species 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 208000008498 Infantile Refsum disease Diseases 0.000 description 2
- 206010021750 Infantile Spasms Diseases 0.000 description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 208000028226 Krabbe disease Diseases 0.000 description 2
- 239000005411 L01XE02 - Gefitinib Substances 0.000 description 2
- 239000005551 L01XE03 - Erlotinib Substances 0.000 description 2
- 102100021926 Low-density lipoprotein receptor-related protein 5 Human genes 0.000 description 2
- 108060001084 Luciferase Proteins 0.000 description 2
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 description 2
- 208000002569 Machado-Joseph Disease Diseases 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 201000002983 Mobius syndrome Diseases 0.000 description 2
- 208000026072 Motor neurone disease Diseases 0.000 description 2
- 230000025190 Mullerian duct regression Effects 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 201000003793 Myelodysplastic syndrome Diseases 0.000 description 2
- 208000010316 Myotonia congenita Diseases 0.000 description 2
- 201000004404 Neurofibroma Diseases 0.000 description 2
- 208000009905 Neurofibromatoses Diseases 0.000 description 2
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 2
- 206010053854 Opsoclonus myoclonus Diseases 0.000 description 2
- 208000000035 Osteochondroma Diseases 0.000 description 2
- 208000008558 Osteophyte Diseases 0.000 description 2
- 206010033799 Paralysis Diseases 0.000 description 2
- 241001494479 Pecora Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 206010073489 Polymicrogyria Diseases 0.000 description 2
- 206010036376 Postherpetic Neuralgia Diseases 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 208000037534 Progressive hemifacial atrophy Diseases 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 208000032831 Ramsay Hunt syndrome Diseases 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 208000021235 Schilder disease Diseases 0.000 description 2
- 201000010208 Seminoma Diseases 0.000 description 2
- 241000710960 Sindbis virus Species 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 201000003696 Sotos syndrome Diseases 0.000 description 2
- 208000036834 Spinocerebellar ataxia type 3 Diseases 0.000 description 2
- 208000032978 Structural Congenital Myopathies Diseases 0.000 description 2
- 206010042265 Sturge-Weber Syndrome Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 description 2
- 201000004810 Vascular dementia Diseases 0.000 description 2
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 2
- JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 description 2
- 201000006791 West syndrome Diseases 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- ZSTCHQOKNUXHLZ-PIRIXANTSA-L [(1r,2r)-2-azanidylcyclohexyl]azanide;oxalate;pentyl n-[1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-methyloxolan-2-yl]-5-fluoro-2-oxopyrimidin-4-yl]carbamate;platinum(4+) Chemical compound [Pt+4].[O-]C(=O)C([O-])=O.[NH-][C@@H]1CCCC[C@H]1[NH-].C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](C)O1 ZSTCHQOKNUXHLZ-PIRIXANTSA-L 0.000 description 2
- 238000002679 ablation Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 208000030597 adult Refsum disease Diseases 0.000 description 2
- OOUACICUAVTCEC-LZHWUUGESA-N aezs-108 Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)COC(=O)CCCC(=O)NCCCC[C@@H](NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H]1NC(=O)CC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)NCC(N)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 OOUACICUAVTCEC-LZHWUUGESA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000004037 angiogenesis inhibitor Substances 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- 230000006907 apoptotic process Effects 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 239000013011 aqueous formulation Substances 0.000 description 2
- 206010003246 arthritis Diseases 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 201000006431 brachial plexus neuropathy Diseases 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 229940088954 camptosar Drugs 0.000 description 2
- 229960004117 capecitabine Drugs 0.000 description 2
- 208000002458 carcinoid tumor Diseases 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 201000005795 chronic inflammatory demyelinating polyneuritis Diseases 0.000 description 2
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 description 2
- 238000005354 coacervation Methods 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 238000013270 controlled release Methods 0.000 description 2
- 230000001351 cycling effect Effects 0.000 description 2
- 229940097362 cyclodextrins Drugs 0.000 description 2
- 229960004397 cyclophosphamide Drugs 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 229960004679 doxorubicin Drugs 0.000 description 2
- 229940112141 dry powder inhaler Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000004064 dysfunction Effects 0.000 description 2
- 206010014599 encephalitis Diseases 0.000 description 2
- 201000002491 encephalomyelitis Diseases 0.000 description 2
- 239000007920 enema Substances 0.000 description 2
- 229940079360 enema for constipation Drugs 0.000 description 2
- AAKJLRGGTJKAMG-UHFFFAOYSA-N erlotinib Chemical compound C=12C=C(OCCOC)C(OCCOC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 AAKJLRGGTJKAMG-UHFFFAOYSA-N 0.000 description 2
- 229960005420 etoposide Drugs 0.000 description 2
- 208000002980 facial hemiatrophy Diseases 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 229960002584 gefitinib Drugs 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 125000005456 glyceride group Chemical group 0.000 description 2
- QBKSWRVVCFFDOT-UHFFFAOYSA-N gossypol Chemical compound CC(C)C1=C(O)C(O)=C(C=O)C2=C(O)C(C=3C(O)=C4C(C=O)=C(O)C(O)=C(C4=CC=3C)C(C)C)=C(C)C=C21 QBKSWRVVCFFDOT-UHFFFAOYSA-N 0.000 description 2
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 description 2
- 229920002674 hyaluronan Polymers 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 201000010985 invasive ductal carcinoma Diseases 0.000 description 2
- 201000010260 leiomyoma Diseases 0.000 description 2
- 208000036546 leukodystrophy Diseases 0.000 description 2
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- 239000008176 lyophilized powder Substances 0.000 description 2
- 108700003825 lysine(6)-doxorubicin LHRH Proteins 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 206010027191 meningioma Diseases 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 125000002757 morpholinyl group Chemical group 0.000 description 2
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 description 2
- OKUYTVHRBWHVQU-UHFFFAOYSA-N n-(5-bromopyridin-3-yl)-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=CN=CC(Br)=C1 OKUYTVHRBWHVQU-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 239000002105 nanoparticle Substances 0.000 description 2
- 210000002850 nasal mucosa Anatomy 0.000 description 2
- 201000004931 neurofibromatosis Diseases 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 210000001331 nose Anatomy 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 229920001983 poloxamer Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 2
- 229940080818 propionamide Drugs 0.000 description 2
- 210000002307 prostate Anatomy 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 2
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
- 238000007674 radiofrequency ablation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 208000002477 septooptic dysplasia Diseases 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 229960002668 sodium chloride Drugs 0.000 description 2
- 208000005198 spinal stenosis Diseases 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 206010043207 temporal arteritis Diseases 0.000 description 2
- NRUKOCRGYNPUPR-QBPJDGROSA-N teniposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@@H](OC[C@H]4O3)C=3SC=CC=3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NRUKOCRGYNPUPR-QBPJDGROSA-N 0.000 description 2
- 229960001278 teniposide Drugs 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 229960000303 topotecan Drugs 0.000 description 2
- UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 238000000844 transformation Methods 0.000 description 2
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 208000006961 tropical spastic paraparesis Diseases 0.000 description 2
- 241000701161 unidentified adenovirus Species 0.000 description 2
- 241001529453 unidentified herpesvirus Species 0.000 description 2
- 229960003048 vinblastine Drugs 0.000 description 2
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 2
- GBABOYUKABKIAF-IELIFDKJSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-IELIFDKJSA-N 0.000 description 2
- 229960002066 vinorelbine Drugs 0.000 description 2
- 208000029257 vision disease Diseases 0.000 description 2
- 208000006542 von Hippel-Lindau disease Diseases 0.000 description 2
- 235000012431 wafers Nutrition 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical class CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 description 1
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- YXTKHLHCVFUPPT-YYFJYKOTSA-N (2s)-2-[[4-[(2-amino-5-formyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid;(1r,2r)-1,2-dimethanidylcyclohexane;5-fluoro-1h-pyrimidine-2,4-dione;oxalic acid;platinum(2+) Chemical compound [Pt+2].OC(=O)C(O)=O.[CH2-][C@@H]1CCCC[C@H]1[CH2-].FC1=CNC(=O)NC1=O.C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 YXTKHLHCVFUPPT-YYFJYKOTSA-N 0.000 description 1
- CVCLJVVBHYOXDC-IAZSKANUSA-N (2z)-2-[(5z)-5-[(3,5-dimethyl-1h-pyrrol-2-yl)methylidene]-4-methoxypyrrol-2-ylidene]indole Chemical compound COC1=C\C(=C/2N=C3C=CC=CC3=C\2)N\C1=C/C=1NC(C)=CC=1C CVCLJVVBHYOXDC-IAZSKANUSA-N 0.000 description 1
- ICLYJLBTOGPLMC-KVVVOXFISA-N (z)-octadec-9-enoate;tris(2-hydroxyethyl)azanium Chemical compound OCCN(CCO)CCO.CCCCCCCC\C=C/CCCCCCCC(O)=O ICLYJLBTOGPLMC-KVVVOXFISA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical group CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 1
- IGERFAHWSHDDHX-UHFFFAOYSA-N 1,3-dioxanyl Chemical group [CH]1OCCCO1 IGERFAHWSHDDHX-UHFFFAOYSA-N 0.000 description 1
- JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 description 1
- 125000005940 1,4-dioxanyl group Chemical group 0.000 description 1
- IQFYYKKMVGJFEH-OFKYTIFKSA-N 1-[(2r,4s,5r)-4-hydroxy-5-(tritiooxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione Chemical compound C1[C@H](O)[C@@H](CO[3H])O[C@H]1N1C(=O)NC(=O)C(C)=C1 IQFYYKKMVGJFEH-OFKYTIFKSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 108010058566 130-nm albumin-bound paclitaxel Proteins 0.000 description 1
- WCXFPLXZZSWROM-UHFFFAOYSA-N 1h-pyrazolo[4,3-c]pyridine Chemical compound C1=NC=C2C=NNC2=C1 WCXFPLXZZSWROM-UHFFFAOYSA-N 0.000 description 1
- NHSOOAWURRKYMM-UHFFFAOYSA-N 2,3-dihydro-1,4-benzoxathiine Chemical compound C1=CC=C2OCCSC2=C1 NHSOOAWURRKYMM-UHFFFAOYSA-N 0.000 description 1
- CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 description 1
- NDMPLJNOPCLANR-UHFFFAOYSA-N 3,4-dihydroxy-15-(4-hydroxy-18-methoxycarbonyl-5,18-seco-ibogamin-18-yl)-16-methoxy-1-methyl-6,7-didehydro-aspidospermidine-3-carboxylic acid methyl ester Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 NDMPLJNOPCLANR-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 description 1
- MDOJTZQKHMAPBK-UHFFFAOYSA-N 4-iodo-3-nitrobenzamide Chemical compound NC(=O)C1=CC=C(I)C([N+]([O-])=O)=C1 MDOJTZQKHMAPBK-UHFFFAOYSA-N 0.000 description 1
- VXWVFZFZYXOBTA-UHFFFAOYSA-N 5-bromo-1h-indole Chemical compound BrC1=CC=C2NC=CC2=C1 VXWVFZFZYXOBTA-UHFFFAOYSA-N 0.000 description 1
- XIMCGXXYEMOWQP-UHFFFAOYSA-N 5-bromo-n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=C(Br)C=N1 XIMCGXXYEMOWQP-UHFFFAOYSA-N 0.000 description 1
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 1
- STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- 206010065040 AIDS dementia complex Diseases 0.000 description 1
- 108700001666 APC Genes Proteins 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 235000006491 Acacia senegal Nutrition 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 206010001233 Adenoma benign Diseases 0.000 description 1
- 102100034540 Adenomatous polyposis coli protein Human genes 0.000 description 1
- 201000002882 Agraphia Diseases 0.000 description 1
- 208000007848 Alcoholism Diseases 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 206010003062 Apraxia Diseases 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 206010003571 Astrocytoma Diseases 0.000 description 1
- 206010003594 Ataxia telangiectasia Diseases 0.000 description 1
- 102000007371 Ataxin-3 Human genes 0.000 description 1
- 102000014461 Ataxins Human genes 0.000 description 1
- 108010078286 Ataxins Proteins 0.000 description 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 description 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- 206010003840 Autonomic nervous system imbalance Diseases 0.000 description 1
- MLDQJTXFUGDVEO-UHFFFAOYSA-N BAY-43-9006 Chemical compound C1=NC(C(=O)NC)=CC(OC=2C=CC(NC(=O)NC=3C=C(C(Cl)=CC=3)C(F)(F)F)=CC=2)=C1 MLDQJTXFUGDVEO-UHFFFAOYSA-N 0.000 description 1
- 206010004146 Basal cell carcinoma Diseases 0.000 description 1
- 208000006373 Bell palsy Diseases 0.000 description 1
- 208000034577 Benign intracranial hypertension Diseases 0.000 description 1
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 102100022548 Beta-hexosaminidase subunit alpha Human genes 0.000 description 1
- 208000020925 Bipolar disease Diseases 0.000 description 1
- 108010006654 Bleomycin Proteins 0.000 description 1
- 201000004940 Bloch-Sulzberger syndrome Diseases 0.000 description 1
- 102000004506 Blood Proteins Human genes 0.000 description 1
- 108010017384 Blood Proteins Proteins 0.000 description 1
- 206010073106 Bone giant cell tumour malignant Diseases 0.000 description 1
- 206010006074 Brachial plexus injury Diseases 0.000 description 1
- 206010068597 Bulbospinal muscular atrophy congenital Diseases 0.000 description 1
- 101100156752 Caenorhabditis elegans cwn-1 gene Proteins 0.000 description 1
- 208000022526 Canavan disease Diseases 0.000 description 1
- 206010058019 Cancer Pain Diseases 0.000 description 1
- 208000009458 Carcinoma in Situ Diseases 0.000 description 1
- 208000001387 Causalgia Diseases 0.000 description 1
- 206010064012 Central pain syndrome Diseases 0.000 description 1
- 208000023442 Cephalocele Diseases 0.000 description 1
- 206010008025 Cerebellar ataxia Diseases 0.000 description 1
- 206010065559 Cerebral arteriosclerosis Diseases 0.000 description 1
- 206010008096 Cerebral atrophy Diseases 0.000 description 1
- 206010053684 Cerebrohepatorenal syndrome Diseases 0.000 description 1
- 206010008263 Cervical dysplasia Diseases 0.000 description 1
- 206010008313 Cervical spinal stenosis Diseases 0.000 description 1
- 201000006868 Charcot-Marie-Tooth disease type 3 Diseases 0.000 description 1
- 201000005262 Chondroma Diseases 0.000 description 1
- 208000005243 Chondrosarcoma Diseases 0.000 description 1
- 201000009047 Chordoma Diseases 0.000 description 1
- 206010008748 Chorea Diseases 0.000 description 1
- 208000006332 Choriocarcinoma Diseases 0.000 description 1
- 208000000094 Chronic Pain Diseases 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 description 1
- 206010048832 Colon adenoma Diseases 0.000 description 1
- 208000013586 Complex regional pain syndrome type 1 Diseases 0.000 description 1
- 206010010356 Congenital anomaly Diseases 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 208000020406 Creutzfeldt Jacob disease Diseases 0.000 description 1
- 208000003407 Creutzfeldt-Jakob Syndrome Diseases 0.000 description 1
- 208000010859 Creutzfeldt-Jakob disease Diseases 0.000 description 1
- 208000012514 Cumulative Trauma disease Diseases 0.000 description 1
- 108010024986 Cyclin-Dependent Kinase 2 Proteins 0.000 description 1
- 108010025464 Cyclin-Dependent Kinase 4 Proteins 0.000 description 1
- 102000013698 Cyclin-Dependent Kinase 6 Human genes 0.000 description 1
- 108010025468 Cyclin-Dependent Kinase 6 Proteins 0.000 description 1
- 102100036239 Cyclin-dependent kinase 2 Human genes 0.000 description 1
- 102100036252 Cyclin-dependent kinase 4 Human genes 0.000 description 1
- 206010011732 Cyst Diseases 0.000 description 1
- 201000003883 Cystic fibrosis Diseases 0.000 description 1
- 206010011831 Cytomegalovirus infection Diseases 0.000 description 1
- 230000006820 DNA synthesis Effects 0.000 description 1
- 108010092160 Dactinomycin Proteins 0.000 description 1
- 201000003863 Dandy-Walker Syndrome Diseases 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- 208000019246 Developmental coordination disease Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 101100286286 Dictyostelium discoideum ipi gene Proteins 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- 201000007547 Dravet syndrome Diseases 0.000 description 1
- 206010049669 Dyscalculia Diseases 0.000 description 1
- 208000007033 Dysgerminoma Diseases 0.000 description 1
- 208000000471 Dysplastic Nevus Syndrome Diseases 0.000 description 1
- 208000014094 Dystonic disease Diseases 0.000 description 1
- 201000008009 Early infantile epileptic encephalopathy Diseases 0.000 description 1
- 206010071545 Early infantile epileptic encephalopathy with burst-suppression Diseases 0.000 description 1
- 201000009051 Embryonal Carcinoma Diseases 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 206010014567 Empty Sella Syndrome Diseases 0.000 description 1
- 206010049020 Encephalitis periaxialis diffusa Diseases 0.000 description 1
- 208000002403 Encephalocele Diseases 0.000 description 1
- 208000000271 Encopresis Diseases 0.000 description 1
- 206010014824 Endotoxic shock Diseases 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 206010014967 Ependymoma Diseases 0.000 description 1
- YQYJSBFKSSDGFO-UHFFFAOYSA-N Epihygromycin Natural products OC1C(O)C(C(=O)C)OC1OC(C(=C1)O)=CC=C1C=C(C)C(=O)NC1C(O)C(O)C2OCOC2C1O YQYJSBFKSSDGFO-UHFFFAOYSA-N 0.000 description 1
- HTIJFSOGRVMCQR-UHFFFAOYSA-N Epirubicin Natural products COc1cccc2C(=O)c3c(O)c4CC(O)(CC(OC5CC(N)C(=O)C(C)O5)c4c(O)c3C(=O)c12)C(=O)CO HTIJFSOGRVMCQR-UHFFFAOYSA-N 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 241001125671 Eretmochelys imbricata Species 0.000 description 1
- 102100038595 Estrogen receptor Human genes 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- 208000024720 Fabry Disease Diseases 0.000 description 1
- 206010063006 Facial spasm Diseases 0.000 description 1
- 208000002091 Febrile Seizures Diseases 0.000 description 1
- 208000001640 Fibromyalgia Diseases 0.000 description 1
- MPJKWIXIYCLVCU-UHFFFAOYSA-N Folinic acid Natural products NC1=NC2=C(N(C=O)C(CNc3ccc(cc3)C(=O)NC(CCC(=O)O)CC(=O)O)CN2)C(=O)N1 MPJKWIXIYCLVCU-UHFFFAOYSA-N 0.000 description 1
- 102000003817 Fos-related antigen 1 Human genes 0.000 description 1
- 108090000123 Fos-related antigen 1 Proteins 0.000 description 1
- 208000024412 Friedreich ataxia Diseases 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- 108700012941 GNRH1 Proteins 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 206010017993 Gastrointestinal neoplasms Diseases 0.000 description 1
- 208000015872 Gaucher disease Diseases 0.000 description 1
- 208000000527 Germinoma Diseases 0.000 description 1
- 208000007223 Gerstmann syndrome Diseases 0.000 description 1
- 208000002966 Giant Cell Tumor of Bone Diseases 0.000 description 1
- 208000007569 Giant Cell Tumors Diseases 0.000 description 1
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 description 1
- 235000011201 Ginkgo Nutrition 0.000 description 1
- 244000194101 Ginkgo biloba Species 0.000 description 1
- 235000008100 Ginkgo biloba Nutrition 0.000 description 1
- 201000005409 Gliomatosis cerebri Diseases 0.000 description 1
- 206010018404 Glucagonoma Diseases 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 239000000579 Gonadotropin-Releasing Hormone Substances 0.000 description 1
- 206010018691 Granuloma Diseases 0.000 description 1
- 208000035895 Guillain-Barré syndrome Diseases 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 208000004095 Hemifacial Spasm Diseases 0.000 description 1
- 206010019629 Hepatic adenoma Diseases 0.000 description 1
- 208000002972 Hepatolenticular Degeneration Diseases 0.000 description 1
- 208000006411 Hereditary Sensory and Motor Neuropathy Diseases 0.000 description 1
- 208000007514 Herpes zoster Diseases 0.000 description 1
- 101000904173 Homo sapiens Progonadoliberin-1 Proteins 0.000 description 1
- 102000008100 Human Serum Albumin Human genes 0.000 description 1
- 108091006905 Human Serum Albumin Proteins 0.000 description 1
- 241000701806 Human papillomavirus Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 208000037171 Hypercorticoidism Diseases 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
- XDXDZDZNSLXDNA-TZNDIEGXSA-N Idarubicin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XDXDZDZNSLXDNA-TZNDIEGXSA-N 0.000 description 1
- XDXDZDZNSLXDNA-UHFFFAOYSA-N Idarubicin Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XDXDZDZNSLXDNA-UHFFFAOYSA-N 0.000 description 1
- 208000018127 Idiopathic intracranial hypertension Diseases 0.000 description 1
- 208000007031 Incontinentia pigmenti Diseases 0.000 description 1
- 208000035899 Infantile spasms syndrome Diseases 0.000 description 1
- 206010022158 Injury to brachial plexus due to birth trauma Diseases 0.000 description 1
- 208000005045 Interdigitating dendritic cell sarcoma Diseases 0.000 description 1
- 208000018650 Intervertebral disc disease Diseases 0.000 description 1
- 201000008450 Intracranial aneurysm Diseases 0.000 description 1
- 206010022773 Intracranial pressure increased Diseases 0.000 description 1
- 208000037396 Intraductal Noninfiltrating Carcinoma Diseases 0.000 description 1
- 206010073094 Intraductal proliferative breast lesion Diseases 0.000 description 1
- 102000004310 Ion Channels Human genes 0.000 description 1
- 208000000209 Isaacs syndrome Diseases 0.000 description 1
- 201000008645 Joubert syndrome Diseases 0.000 description 1
- 206010048804 Kearns-Sayre syndrome Diseases 0.000 description 1
- 208000002260 Keloid Diseases 0.000 description 1
- 208000027747 Kennedy disease Diseases 0.000 description 1
- 208000006541 Klippel-Feil syndrome Diseases 0.000 description 1
- 239000005517 L01XE01 - Imatinib Substances 0.000 description 1
- 239000005511 L01XE05 - Sorafenib Substances 0.000 description 1
- 239000002146 L01XE16 - Crizotinib Substances 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 208000005870 Lafora disease Diseases 0.000 description 1
- 208000014161 Lafora myoclonic epilepsy Diseases 0.000 description 1
- 201000010743 Lambert-Eaton myasthenic syndrome Diseases 0.000 description 1
- 208000006136 Leigh Disease Diseases 0.000 description 1
- 208000017507 Leigh syndrome Diseases 0.000 description 1
- 208000018142 Leiomyosarcoma Diseases 0.000 description 1
- 201000006792 Lennox-Gastaut syndrome Diseases 0.000 description 1
- 208000009625 Lesch-Nyhan syndrome Diseases 0.000 description 1
- 208000009829 Lewy Body Disease Diseases 0.000 description 1
- 206010048911 Lissencephaly Diseases 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 208000002404 Liver Cell Adenoma Diseases 0.000 description 1
- 206010073099 Lobular breast carcinoma in situ Diseases 0.000 description 1
- 201000000251 Locked-in syndrome Diseases 0.000 description 1
- 208000016604 Lyme disease Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 208000006644 Malignant Fibrous Histiocytoma Diseases 0.000 description 1
- 208000007054 Medullary Carcinoma Diseases 0.000 description 1
- 208000000172 Medulloblastoma Diseases 0.000 description 1
- 208000005767 Megalencephaly Diseases 0.000 description 1
- 201000002571 Melkersson-Rosenthal syndrome Diseases 0.000 description 1
- 208000027530 Meniere disease Diseases 0.000 description 1
- 201000009906 Meningitis Diseases 0.000 description 1
- 208000008948 Menkes Kinky Hair Syndrome Diseases 0.000 description 1
- 208000012583 Menkes disease Diseases 0.000 description 1
- 206010027406 Mesothelioma Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 201000002169 Mitochondrial myopathy Diseases 0.000 description 1
- 229930192392 Mitomycin Natural products 0.000 description 1
- 206010027802 Moebius II syndrome Diseases 0.000 description 1
- 208000034167 Moebius syndrome Diseases 0.000 description 1
- 206010069681 Monomelic amyotrophy Diseases 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- 208000019896 Motor Skills disease Diseases 0.000 description 1
- 208000016285 Movement disease Diseases 0.000 description 1
- 208000009433 Moyamoya Disease Diseases 0.000 description 1
- 208000002678 Mucopolysaccharidoses Diseases 0.000 description 1
- 208000005314 Multi-Infarct Dementia Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 208000008238 Muscle Spasticity Diseases 0.000 description 1
- 208000029578 Muscle disease Diseases 0.000 description 1
- 206010028424 Myasthenic syndrome Diseases 0.000 description 1
- 101710135898 Myc proto-oncogene protein Proteins 0.000 description 1
- 102100038895 Myc proto-oncogene protein Human genes 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 102100026784 Myelin proteolipid protein Human genes 0.000 description 1
- 206010028570 Myelopathy Diseases 0.000 description 1
- 208000014767 Myeloproliferative disease Diseases 0.000 description 1
- 208000036572 Myoclonic epilepsy Diseases 0.000 description 1
- 208000002033 Myoclonus Diseases 0.000 description 1
- 201000002481 Myositis Diseases 0.000 description 1
- 208000012905 Myotonic disease Diseases 0.000 description 1
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229910020889 NaBH3 Inorganic materials 0.000 description 1
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 1
- 201000005625 Neuroleptic malignant syndrome Diseases 0.000 description 1
- 206010072359 Neuromyotonia Diseases 0.000 description 1
- 208000002537 Neuronal Ceroid-Lipofuscinoses Diseases 0.000 description 1
- 208000007125 Neurotoxicity Syndromes Diseases 0.000 description 1
- 208000014060 Niemann-Pick disease Diseases 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- 208000020265 O'Sullivan-McLeod syndrome Diseases 0.000 description 1
- 206010068106 Occipital neuralgia Diseases 0.000 description 1
- 201000010133 Oligodendroglioma Diseases 0.000 description 1
- 208000003435 Optic Neuritis Diseases 0.000 description 1
- 206010069350 Osmotic demyelination syndrome Diseases 0.000 description 1
- 206010031149 Osteitis Diseases 0.000 description 1
- 208000010191 Osteitis Deformans Diseases 0.000 description 1
- 208000004286 Osteochondrodysplasias Diseases 0.000 description 1
- 201000009859 Osteochondrosis Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 239000012661 PARP inhibitor Substances 0.000 description 1
- 239000012828 PI3K inhibitor Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 208000027868 Paget disease Diseases 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 101100272976 Panax ginseng CYP716A53v2 gene Proteins 0.000 description 1
- 208000017493 Pelizaeus-Merzbacher disease Diseases 0.000 description 1
- 206010051766 Perineurial cyst Diseases 0.000 description 1
- 241000577979 Peromyscus spicilegus Species 0.000 description 1
- 208000002163 Phyllodes Tumor Diseases 0.000 description 1
- 208000000609 Pick Disease of the Brain Diseases 0.000 description 1
- 208000007641 Pinealoma Diseases 0.000 description 1
- 229920002507 Poloxamer 124 Polymers 0.000 description 1
- 229940121906 Poly ADP ribose polymerase inhibitor Drugs 0.000 description 1
- 206010065159 Polychondritis Diseases 0.000 description 1
- 206010036172 Porencephaly Diseases 0.000 description 1
- 206010057244 Post viral fatigue syndrome Diseases 0.000 description 1
- 206010052469 Postictal paralysis Diseases 0.000 description 1
- 208000010366 Postpoliomyelitis syndrome Diseases 0.000 description 1
- 208000009052 Precursor T-Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 description 1
- 208000017414 Precursor T-cell acute lymphoblastic leukemia Diseases 0.000 description 1
- 208000032319 Primary lateral sclerosis Diseases 0.000 description 1
- 102100025803 Progesterone receptor Human genes 0.000 description 1
- 102100024028 Progonadoliberin-1 Human genes 0.000 description 1
- 208000004403 Prostatic Hyperplasia Diseases 0.000 description 1
- 102000007327 Protamines Human genes 0.000 description 1
- 108010007568 Protamines Proteins 0.000 description 1
- 208000033526 Proximal spinal muscular atrophy type 3 Diseases 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 206010071141 Rasmussen encephalitis Diseases 0.000 description 1
- 208000004160 Rasmussen subacute encephalitis Diseases 0.000 description 1
- 208000015634 Rectal Neoplasms Diseases 0.000 description 1
- 206010063837 Reperfusion injury Diseases 0.000 description 1
- 208000005793 Restless legs syndrome Diseases 0.000 description 1
- 208000007014 Retinitis pigmentosa Diseases 0.000 description 1
- 201000007981 Reye syndrome Diseases 0.000 description 1
- 208000005678 Rhabdomyoma Diseases 0.000 description 1
- 240000000353 Ruscus aculeatus Species 0.000 description 1
- 235000003500 Ruscus aculeatus Nutrition 0.000 description 1
- 239000004189 Salinomycin Substances 0.000 description 1
- KQXDHUJYNAXLNZ-XQSDOZFQSA-N Salinomycin Chemical compound O1[C@@H]([C@@H](CC)C(O)=O)CC[C@H](C)[C@@H]1[C@@H](C)[C@H](O)[C@H](C)C(=O)[C@H](CC)[C@@H]1[C@@H](C)C[C@@H](C)[C@@]2(C=C[C@@H](O)[C@@]3(O[C@@](C)(CC3)[C@@H]3O[C@@H](C)[C@@](O)(CC)CC3)O2)O1 KQXDHUJYNAXLNZ-XQSDOZFQSA-N 0.000 description 1
- 208000005688 Salter-Harris Fractures Diseases 0.000 description 1
- 208000021811 Sandhoff disease Diseases 0.000 description 1
- 208000000729 Schizencephaly Diseases 0.000 description 1
- 206010040070 Septic Shock Diseases 0.000 description 1
- 208000000097 Sertoli-Leydig cell tumor Diseases 0.000 description 1
- 206010073677 Severe myoclonic epilepsy of infancy Diseases 0.000 description 1
- 208000009106 Shy-Drager Syndrome Diseases 0.000 description 1
- 241000580858 Simian-Human immunodeficiency virus Species 0.000 description 1
- 208000021386 Sjogren Syndrome Diseases 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 206010064387 Sotos' syndrome Diseases 0.000 description 1
- 206010041415 Spastic paralysis Diseases 0.000 description 1
- 201000010829 Spina bifida Diseases 0.000 description 1
- 208000006097 Spinal Dysraphism Diseases 0.000 description 1
- 208000003954 Spinal Muscular Atrophies of Childhood Diseases 0.000 description 1
- 208000009415 Spinocerebellar Ataxias Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 206010072148 Stiff-Person syndrome Diseases 0.000 description 1
- 208000037065 Subacute sclerosing leukoencephalitis Diseases 0.000 description 1
- 206010042297 Subacute sclerosing panencephalitis Diseases 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 101000996723 Sus scrofa Gonadotropin-releasing hormone receptor Proteins 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 208000027522 Sydenham chorea Diseases 0.000 description 1
- 208000035239 Synesthesia Diseases 0.000 description 1
- 206010042928 Syringomyelia Diseases 0.000 description 1
- 206010042953 Systemic sclerosis Diseases 0.000 description 1
- 208000029052 T-cell acute lymphoblastic leukemia Diseases 0.000 description 1
- 206010043118 Tardive Dyskinesia Diseases 0.000 description 1
- 208000003664 Tarlov Cysts Diseases 0.000 description 1
- 206010043121 Tarsal tunnel syndrome Diseases 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229940123237 Taxane Drugs 0.000 description 1
- 208000022292 Tay-Sachs disease Diseases 0.000 description 1
- 206010043376 Tetanus Diseases 0.000 description 1
- QHOPXUFELLHKAS-UHFFFAOYSA-N Thespesin Natural products CC(C)c1c(O)c(O)c2C(O)Oc3c(c(C)cc1c23)-c1c2OC(O)c3c(O)c(O)c(C(C)C)c(cc1C)c23 QHOPXUFELLHKAS-UHFFFAOYSA-N 0.000 description 1
- 239000004012 Tofacitinib Substances 0.000 description 1
- 208000035317 Total hypoxanthine-guanine phosphoribosyl transferase deficiency Diseases 0.000 description 1
- 208000000323 Tourette Syndrome Diseases 0.000 description 1
- 208000016620 Tourette disease Diseases 0.000 description 1
- 206010044221 Toxic encephalopathy Diseases 0.000 description 1
- 231100000076 Toxic encephalopathy Toxicity 0.000 description 1
- 101710150448 Transcriptional regulator Myc Proteins 0.000 description 1
- 208000032109 Transient ischaemic attack Diseases 0.000 description 1
- 206010044565 Tremor Diseases 0.000 description 1
- 208000003721 Triple Negative Breast Neoplasms Diseases 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 206010044696 Tropical spastic paresis Diseases 0.000 description 1
- 208000026911 Tuberous sclerosis complex Diseases 0.000 description 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
- 208000015778 Undifferentiated pleomorphic sarcoma Diseases 0.000 description 1
- 206010046298 Upper motor neurone lesion Diseases 0.000 description 1
- 108091008605 VEGF receptors Proteins 0.000 description 1
- 208000036826 VIIth nerve paralysis Diseases 0.000 description 1
- 208000009311 VIPoma Diseases 0.000 description 1
- 235000017537 Vaccinium myrtillus Nutrition 0.000 description 1
- 244000078534 Vaccinium myrtillus Species 0.000 description 1
- 102000009484 Vascular Endothelial Growth Factor Receptors Human genes 0.000 description 1
- 229940122803 Vinca alkaloid Drugs 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 206010073653 Visual perseveration Diseases 0.000 description 1
- 208000033559 Waldenström macroglobulinemia Diseases 0.000 description 1
- 206010049644 Williams syndrome Diseases 0.000 description 1
- 208000018839 Wilson disease Diseases 0.000 description 1
- 108700020987 Wnt-1 Proteins 0.000 description 1
- 208000006269 X-Linked Bulbo-Spinal Atrophy Diseases 0.000 description 1
- 206010048214 Xanthoma Diseases 0.000 description 1
- 206010048215 Xanthomatosis Diseases 0.000 description 1
- 241000269370 Xenopus <genus> Species 0.000 description 1
- 201000004525 Zellweger Syndrome Diseases 0.000 description 1
- 208000036813 Zellweger spectrum disease Diseases 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- BOGSOFADOWIECK-UHFFFAOYSA-N [N].C=1C=NNC=1 Chemical compound [N].C=1C=NNC=1 BOGSOFADOWIECK-UHFFFAOYSA-N 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 229940028652 abraxane Drugs 0.000 description 1
- 239000003070 absorption delaying agent Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 238000009825 accumulation Methods 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
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229930183665 actinomycin Natural products 0.000 description 1
- YAJCHEVQCOHZDC-QMMNLEPNSA-N actrapid Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H]1CSSC[C@H]2C(=O)N[C@H](C(=O)N[C@@H](CO)C(=O)N[C@H](C(=O)N[C@@H](C(N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3C=CC(O)=CC=3)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3N=CNC=3)NC(=O)[C@H](CO)NC(=O)CNC1=O)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H]([C@H](C)O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@H](C)O)C(O)=O)C(=O)N[C@@H](CC(N)=O)C(O)=O)=O)CSSC[C@@H](C(N2)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CN)[C@H](C)CC)[C@H](C)CC)[C@H](C)O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C=CC=CC=1)C(C)C)C(N)=O)C1=CNC=N1 YAJCHEVQCOHZDC-QMMNLEPNSA-N 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 208000002718 adenomatoid tumor Diseases 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 201000005255 adrenal gland hyperfunction Diseases 0.000 description 1
- 208000024447 adrenal gland neoplasm Diseases 0.000 description 1
- 201000007930 alcohol dependence Diseases 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 125000005257 alkyl acyl group Chemical group 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229960000473 altretamine Drugs 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 229940063655 aluminum stearate Drugs 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- XCPGHVQEEXUHNC-UHFFFAOYSA-N amsacrine Chemical compound COC1=CC(NS(C)(=O)=O)=CC=C1NC1=C(C=CC=C2)C2=NC2=CC=CC=C12 XCPGHVQEEXUHNC-UHFFFAOYSA-N 0.000 description 1
- 229960001220 amsacrine Drugs 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 238000002399 angioplasty Methods 0.000 description 1
- 229940045799 anthracyclines and related substance Drugs 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000340 anti-metabolite Effects 0.000 description 1
- 230000001028 anti-proliverative effect Effects 0.000 description 1
- 229940100197 antimetabolite Drugs 0.000 description 1
- 239000002256 antimetabolite Substances 0.000 description 1
- 239000003972 antineoplastic antibiotic Substances 0.000 description 1
- 229960003982 apatinib Drugs 0.000 description 1
- 201000007201 aphasia Diseases 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 206010003074 arachnoiditis Diseases 0.000 description 1
- 239000003886 aromatase inhibitor Substances 0.000 description 1
- 229940046844 aromatase inhibitors Drugs 0.000 description 1
- 238000007080 aromatic substitution reaction Methods 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 description 1
- 208000021900 auditory perceptual disease Diseases 0.000 description 1
- 230000001363 autoimmune Effects 0.000 description 1
- 201000004562 autosomal dominant cerebellar ataxia Diseases 0.000 description 1
- 208000031375 autosomal dominant myotonia congenita Diseases 0.000 description 1
- 229940120638 avastin Drugs 0.000 description 1
- VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 description 1
- 229960002170 azathioprine Drugs 0.000 description 1
- LMEKQMALGUDUQG-UHFFFAOYSA-N azathioprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC=NC2=C1NC=N2 LMEKQMALGUDUQG-UHFFFAOYSA-N 0.000 description 1
- 125000002393 azetidinyl group Chemical group 0.000 description 1
- 125000004069 aziridinyl group Chemical group 0.000 description 1
- 125000004045 azirinyl group Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 229960000397 bevacizumab Drugs 0.000 description 1
- ACWZRVQXLIRSDF-UHFFFAOYSA-N binimetinib Chemical compound OCCONC(=O)C=1C=C2N(C)C=NC2=C(F)C=1NC1=CC=C(Br)C=C1F ACWZRVQXLIRSDF-UHFFFAOYSA-N 0.000 description 1
- 238000004166 bioassay Methods 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
- 201000011143 bone giant cell tumor Diseases 0.000 description 1
- 208000018339 bone inflammation disease Diseases 0.000 description 1
- GXJABQQUPOEUTA-RDJZCZTQSA-N bortezomib Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)B(O)O)NC(=O)C=1N=CC=NC=1)C1=CC=CC=C1 GXJABQQUPOEUTA-RDJZCZTQSA-N 0.000 description 1
- 201000009480 botryoid rhabdomyosarcoma Diseases 0.000 description 1
- 201000007293 brain stem infarction Diseases 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 201000005389 breast carcinoma in situ Diseases 0.000 description 1
- 201000003149 breast fibroadenoma Diseases 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 208000003362 bronchogenic carcinoma Diseases 0.000 description 1
- 201000002143 bronchus adenoma Diseases 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 229960004562 carboplatin Drugs 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 208000003295 carpal tunnel syndrome Diseases 0.000 description 1
- 230000022131 cell cycle Effects 0.000 description 1
- 230000024245 cell differentiation Effects 0.000 description 1
- 239000013592 cell lysate Substances 0.000 description 1
- 108091092328 cellular RNA Proteins 0.000 description 1
- 208000010353 central nervous system vasculitis Diseases 0.000 description 1
- 208000009885 central pontine myelinolysis Diseases 0.000 description 1
- 208000025434 cerebellar degeneration Diseases 0.000 description 1
- 206010008129 cerebral palsy Diseases 0.000 description 1
- 208000019065 cervical carcinoma Diseases 0.000 description 1
- 210000003679 cervix uteri Anatomy 0.000 description 1
- 229960005395 cetuximab Drugs 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 229960004630 chlorambucil Drugs 0.000 description 1
- JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 description 1
- 201000005217 chondroblastoma Diseases 0.000 description 1
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 208000009060 clear cell adenocarcinoma Diseases 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000001427 coherent effect Effects 0.000 description 1
- 239000000515 collagen sponge Substances 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 208000014439 complex regional pain syndrome type 2 Diseases 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 229920002770 condensed tannin Polymers 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 239000012059 conventional drug carrier Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- KTEIFNKAUNYNJU-GFCCVEGCSA-N crizotinib Chemical compound O([C@H](C)C=1C(=C(F)C=CC=1Cl)Cl)C(C(=NC=1)N)=CC=1C(=C1)C=NN1C1CCNCC1 KTEIFNKAUNYNJU-GFCCVEGCSA-N 0.000 description 1
- 229960005061 crizotinib Drugs 0.000 description 1
- 238000002681 cryosurgery Methods 0.000 description 1
- 238000000315 cryotherapy Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 description 1
- 229940043378 cyclin-dependent kinase inhibitor Drugs 0.000 description 1
- PNZXMIKHJXIPEK-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1CCCCC1 PNZXMIKHJXIPEK-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 1
- VELDYOPRLMJFIK-UHFFFAOYSA-N cyclopentanecarbaldehyde Chemical compound O=CC1CCCC1 VELDYOPRLMJFIK-UHFFFAOYSA-N 0.000 description 1
- 208000031513 cyst Diseases 0.000 description 1
- 230000001086 cytosolic effect Effects 0.000 description 1
- 229960002465 dabrafenib Drugs 0.000 description 1
- BFSMGDJOXZAERB-UHFFFAOYSA-N dabrafenib Chemical compound S1C(C(C)(C)C)=NC(C=2C(=C(NS(=O)(=O)C=3C(=CC=CC=3F)F)C=CC=2)F)=C1C1=CC=NC(N)=N1 BFSMGDJOXZAERB-UHFFFAOYSA-N 0.000 description 1
- STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 description 1
- 229960000975 daunorubicin Drugs 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 201000001098 delayed sleep phase syndrome Diseases 0.000 description 1
- 208000033921 delayed sleep phase type circadian rhythm sleep disease Diseases 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 208000013257 developmental and epileptic encephalopathy Diseases 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 125000004655 dihydropyridinyl group Chemical group N1(CC=CC=C1)* 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- FSBVERYRVPGNGG-UHFFFAOYSA-N dimagnesium dioxido-bis[[oxido(oxo)silyl]oxy]silane hydrate Chemical compound O.[Mg+2].[Mg+2].[O-][Si](=O)O[Si]([O-])([O-])O[Si]([O-])=O FSBVERYRVPGNGG-UHFFFAOYSA-N 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- 235000019797 dipotassium phosphate Nutrition 0.000 description 1
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003534 dna topoisomerase inhibitor Substances 0.000 description 1
- 229960003668 docetaxel Drugs 0.000 description 1
- 229940115080 doxil Drugs 0.000 description 1
- 208000028715 ductal breast carcinoma in situ Diseases 0.000 description 1
- 201000007273 ductal carcinoma in situ Diseases 0.000 description 1
- 208000019479 dysautonomia Diseases 0.000 description 1
- 206010058319 dysgraphia Diseases 0.000 description 1
- 206010013932 dyslexia Diseases 0.000 description 1
- 208000010118 dystonia Diseases 0.000 description 1
- 210000000883 ear external Anatomy 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 229940120655 eloxatin Drugs 0.000 description 1
- 238000013161 embolization procedure Methods 0.000 description 1
- 201000009409 embryonal rhabdomyosarcoma Diseases 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 201000003914 endometrial carcinoma Diseases 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- YJGVMLPVUAXIQN-UHFFFAOYSA-N epipodophyllotoxin Natural products COC1=C(OC)C(OC)=CC(C2C3=CC=4OCOC=4C=C3C(O)C3C2C(OC3)=O)=C1 YJGVMLPVUAXIQN-UHFFFAOYSA-N 0.000 description 1
- 229960001904 epirubicin Drugs 0.000 description 1
- 229960001433 erlotinib Drugs 0.000 description 1
- 201000011384 erythromelalgia Diseases 0.000 description 1
- 210000003238 esophagus Anatomy 0.000 description 1
- 201000006517 essential tremor Diseases 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 108010038795 estrogen receptors Proteins 0.000 description 1
- 201000007280 estrogen-receptor negative breast cancer Diseases 0.000 description 1
- 201000007281 estrogen-receptor positive breast cancer Diseases 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- LIQODXNTTZAGID-OCBXBXKTSA-N etoposide phosphate Chemical compound COC1=C(OP(O)(O)=O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 LIQODXNTTZAGID-OCBXBXKTSA-N 0.000 description 1
- 229960000752 etoposide phosphate Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 201000010934 exostosis Diseases 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 206010016284 febrile convulsion Diseases 0.000 description 1
- 201000010103 fibrous dysplasia Diseases 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- JYEFSHLLTQIXIO-SMNQTINBSA-N folfiri regimen Chemical compound FC1=CNC(=O)NC1=O.C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1.C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 JYEFSHLLTQIXIO-SMNQTINBSA-N 0.000 description 1
- 239000010200 folin Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- DKFAAPPUYWQKKF-GOEBONIOSA-N gacyclidine Chemical compound C[C@H]1CCCC[C@@]1(C=1SC=CC=1)N1CCCCC1 DKFAAPPUYWQKKF-GOEBONIOSA-N 0.000 description 1
- 229950003638 gacyclidine Drugs 0.000 description 1
- 208000015419 gastrin-producing neuroendocrine tumor Diseases 0.000 description 1
- 201000000052 gastrinoma Diseases 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000007897 gelcap Substances 0.000 description 1
- SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 description 1
- 229960005277 gemcitabine Drugs 0.000 description 1
- 201000003115 germ cell cancer Diseases 0.000 description 1
- 229940080856 gleevec Drugs 0.000 description 1
- 208000005017 glioblastoma Diseases 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- XLXSAKCOAKORKW-UHFFFAOYSA-N gonadorelin Chemical compound C1CCC(C(=O)NCC(N)=O)N1C(=O)C(CCCN=C(N)N)NC(=O)C(CC(C)C)NC(=O)CNC(=O)C(NC(=O)C(CO)NC(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C(CC=1NC=NC=1)NC(=O)C1NC(=O)CC1)CC1=CC=C(O)C=C1 XLXSAKCOAKORKW-UHFFFAOYSA-N 0.000 description 1
- 229930000755 gossypol Natural products 0.000 description 1
- 229950005277 gossypol Drugs 0.000 description 1
- 235000002532 grape seed extract Nutrition 0.000 description 1
- 229940087603 grape seed extract Drugs 0.000 description 1
- 210000004884 grey matter Anatomy 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 208000024348 heart neoplasm Diseases 0.000 description 1
- 208000014951 hematologic disease Diseases 0.000 description 1
- 208000006359 hepatoblastoma Diseases 0.000 description 1
- 201000002735 hepatocellular adenoma Diseases 0.000 description 1
- 229940022353 herceptin Drugs 0.000 description 1
- 208000008675 hereditary spastic paraplegia Diseases 0.000 description 1
- UUVWYPNAQBNQJQ-UHFFFAOYSA-N hexamethylmelamine Chemical compound CN(C)C1=NC(N(C)C)=NC(N(C)C)=N1 UUVWYPNAQBNQJQ-UHFFFAOYSA-N 0.000 description 1
- 210000001624 hip Anatomy 0.000 description 1
- 208000009624 holoprosencephaly Diseases 0.000 description 1
- 230000003284 homeostatic effect Effects 0.000 description 1
- 229940018991 hyalgan Drugs 0.000 description 1
- 201000009075 hydranencephaly Diseases 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 208000003906 hydrocephalus Diseases 0.000 description 1
- 239000008172 hydrogenated vegetable oil Substances 0.000 description 1
- 230000007954 hypoxia Effects 0.000 description 1
- 229960001680 ibuprofen Drugs 0.000 description 1
- 229960000908 idarubicin Drugs 0.000 description 1
- 229960002411 imatinib Drugs 0.000 description 1
- 229960003685 imatinib mesylate Drugs 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 208000026278 immune system disease Diseases 0.000 description 1
- 201000004933 in situ carcinoma Diseases 0.000 description 1
- 238000000099 in vitro assay Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 208000023692 inborn mitochondrial myopathy Diseases 0.000 description 1
- 210000003000 inclusion body Anatomy 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 229950002133 iniparib Drugs 0.000 description 1
- 206010022498 insulinoma Diseases 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 210000002570 interstitial cell Anatomy 0.000 description 1
- 238000007917 intracranial administration Methods 0.000 description 1
- 201000005851 intracranial arteriosclerosis Diseases 0.000 description 1
- 201000009941 intracranial hypertension Diseases 0.000 description 1
- 201000003159 intraductal papilloma Diseases 0.000 description 1
- 206010073095 invasive ductal breast carcinoma Diseases 0.000 description 1
- 206010073096 invasive lobular breast carcinoma Diseases 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 101150041626 ipi gene Proteins 0.000 description 1
- 229940084651 iressa Drugs 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 208000037906 ischaemic injury Diseases 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 239000007951 isotonicity adjuster Substances 0.000 description 1
- 125000003965 isoxazolidinyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 201000004815 juvenile spinal muscular atrophy Diseases 0.000 description 1
- 210000001117 keloid Anatomy 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 208000022013 kidney Wilms tumor Diseases 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 206010023497 kuru Diseases 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 208000003849 large cell carcinoma Diseases 0.000 description 1
- 208000004343 lateral medullary syndrome Diseases 0.000 description 1
- 201000010901 lateral sclerosis Diseases 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- CMJCXYNUCSMDBY-ZDUSSCGKSA-N lgx818 Chemical compound COC(=O)N[C@@H](C)CNC1=NC=CC(C=2C(=NN(C=2)C(C)C)C=2C(=C(NS(C)(=O)=O)C=C(Cl)C=2)F)=N1 CMJCXYNUCSMDBY-ZDUSSCGKSA-N 0.000 description 1
- 206010024627 liposarcoma Diseases 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 208000014817 lissencephaly spectrum disease Diseases 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 201000011059 lobular neoplasia Diseases 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 206010025005 lumbar spinal stenosis Diseases 0.000 description 1
- 208000026535 luminal A breast carcinoma Diseases 0.000 description 1
- 208000026534 luminal B breast carcinoma Diseases 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 206010025135 lupus erythematosus Diseases 0.000 description 1
- 238000012792 lyophilization process Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910000386 magnesium trisilicate Inorganic materials 0.000 description 1
- 229940099273 magnesium trisilicate Drugs 0.000 description 1
- 235000019793 magnesium trisilicate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 230000036244 malformation Effects 0.000 description 1
- 201000004593 malignant giant cell tumor Diseases 0.000 description 1
- 201000000289 malignant teratoma Diseases 0.000 description 1
- 208000027202 mammary Paget disease Diseases 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229960004961 mechlorethamine Drugs 0.000 description 1
- HAWPXGHAZFHHAD-UHFFFAOYSA-N mechlorethamine Chemical compound ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 208000023356 medullary thyroid gland carcinoma Diseases 0.000 description 1
- SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 description 1
- 229960001924 melphalan Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 210000002418 meninge Anatomy 0.000 description 1
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 1
- 229960001428 mercaptopurine Drugs 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 230000001394 metastastic effect Effects 0.000 description 1
- 206010061289 metastatic neoplasm Diseases 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 208000004141 microcephaly Diseases 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 239000008185 minitablet Substances 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- CFCUWKMKBJTWLW-BKHRDMLASA-N mithramycin Chemical compound O([C@@H]1C[C@@H](O[C@H](C)[C@H]1O)OC=1C=C2C=C3C[C@H]([C@@H](C(=O)C3=C(O)C2=C(O)C=1C)O[C@@H]1O[C@H](C)[C@@H](O)[C@H](O[C@@H]2O[C@H](C)[C@H](O)[C@H](O[C@@H]3O[C@H](C)[C@@H](O)[C@@](C)(O)C3)C2)C1)[C@H](OC)C(=O)[C@@H](O)[C@@H](C)O)[C@H]1C[C@@H](O)[C@H](O)[C@@H](C)O1 CFCUWKMKBJTWLW-BKHRDMLASA-N 0.000 description 1
- 239000002829 mitogen activated protein kinase inhibitor Substances 0.000 description 1
- 229960004857 mitomycin Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 1
- 208000005264 motor neuron disease Diseases 0.000 description 1
- 208000010492 mucinous cystadenocarcinoma Diseases 0.000 description 1
- 206010028093 mucopolysaccharidosis Diseases 0.000 description 1
- 206010065579 multifocal motor neuropathy Diseases 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 201000006938 muscular dystrophy Diseases 0.000 description 1
- 210000002346 musculoskeletal system Anatomy 0.000 description 1
- 206010028417 myasthenia gravis Diseases 0.000 description 1
- 208000009091 myxoma Diseases 0.000 description 1
- HNXFLSIXGWLLTC-UHFFFAOYSA-N n-(5-bromopyridin-3-yl)-2-methylpropanamide Chemical compound CC(C)C(=O)NC1=CN=CC(Br)=C1 HNXFLSIXGWLLTC-UHFFFAOYSA-N 0.000 description 1
- CSBQRLFLVTYKNK-UHFFFAOYSA-N n-(5-bromopyridin-3-yl)cyclohexanecarboxamide Chemical compound BrC1=CN=CC(NC(=O)C2CCCCC2)=C1 CSBQRLFLVTYKNK-UHFFFAOYSA-N 0.000 description 1
- UYDYXBDAPGBFNR-UHFFFAOYSA-N n-(5-bromopyridin-3-yl)pentanamide Chemical compound CCCCC(=O)NC1=CN=CC(Br)=C1 UYDYXBDAPGBFNR-UHFFFAOYSA-N 0.000 description 1
- LCVFJAPOTXJYHG-UHFFFAOYSA-N n-(5-bromopyridin-3-yl)propanamide Chemical compound CCC(=O)NC1=CN=CC(Br)=C1 LCVFJAPOTXJYHG-UHFFFAOYSA-N 0.000 description 1
- WPEWQEMJFLWMLV-UHFFFAOYSA-N n-[4-(1-cyanocyclopentyl)phenyl]-2-(pyridin-4-ylmethylamino)pyridine-3-carboxamide Chemical compound C=1C=CN=C(NCC=2C=CN=CC=2)C=1C(=O)NC(C=C1)=CC=C1C1(C#N)CCCC1 WPEWQEMJFLWMLV-UHFFFAOYSA-N 0.000 description 1
- MAGVJLLHDZWQFM-UHFFFAOYSA-N n-chloro-n-methylmethanamine Chemical compound CN(C)Cl MAGVJLLHDZWQFM-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 229960002009 naproxen Drugs 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-M naproxen(1-) Chemical compound C1=C([C@H](C)C([O-])=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-M 0.000 description 1
- 201000003631 narcolepsy Diseases 0.000 description 1
- 210000003928 nasal cavity Anatomy 0.000 description 1
- 229940086322 navelbine Drugs 0.000 description 1
- JLYAXFNOILIKPP-KXQOOQHDSA-N navitoclax Chemical compound C([C@@H](NC1=CC=C(C=C1S(=O)(=O)C(F)(F)F)S(=O)(=O)NC(=O)C1=CC=C(C=C1)N1CCN(CC1)CC1=C(CCC(C1)(C)C)C=1C=CC(Cl)=CC=1)CSC=1C=CC=CC=1)CN1CCOCC1 JLYAXFNOILIKPP-KXQOOQHDSA-N 0.000 description 1
- 229950004847 navitoclax Drugs 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- 238000009099 neoadjuvant therapy Methods 0.000 description 1
- 208000019382 nerve compression syndrome Diseases 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 201000011682 nervous system cancer Diseases 0.000 description 1
- 201000008051 neuronal ceroid lipofuscinosis Diseases 0.000 description 1
- 208000004649 neutrophil actin dysfunction Diseases 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 229950006584 obatoclax Drugs 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- FAQDUNYVKQKNLD-UHFFFAOYSA-N olaparib Chemical compound FC1=CC=C(CC2=C3[CH]C=CC=C3C(=O)N=N2)C=C1C(=O)N(CC1)CCN1C(=O)C1CC1 FAQDUNYVKQKNLD-UHFFFAOYSA-N 0.000 description 1
- 229960000572 olaparib Drugs 0.000 description 1
- 208000031237 olivopontocerebellar atrophy Diseases 0.000 description 1
- 238000009806 oophorectomy Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 208000007656 osteochondritis dissecans Diseases 0.000 description 1
- 208000003388 osteoid osteoma Diseases 0.000 description 1
- 208000008798 osteoma Diseases 0.000 description 1
- 208000002865 osteopetrosis Diseases 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 210000003101 oviduct Anatomy 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- LVSJDHGRKAEGLX-UHFFFAOYSA-N oxolane;2,2,2-trifluoroacetic acid Chemical compound C1CCOC1.OC(=O)C(F)(F)F LVSJDHGRKAEGLX-UHFFFAOYSA-N 0.000 description 1
- 238000002640 oxygen therapy Methods 0.000 description 1
- 239000006179 pH buffering agent Substances 0.000 description 1
- 229960001592 paclitaxel Drugs 0.000 description 1
- AHJRHEGDXFFMBM-UHFFFAOYSA-N palbociclib Chemical compound N1=C2N(C3CCCC3)C(=O)C(C(=O)C)=C(C)C2=CN=C1NC(N=C1)=CC=C1N1CCNCC1 AHJRHEGDXFFMBM-UHFFFAOYSA-N 0.000 description 1
- 229960004390 palbociclib Drugs 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 208000021255 pancreatic insulinoma Diseases 0.000 description 1
- 208000002593 pantothenate kinase-associated neurodegeneration Diseases 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 201000010198 papillary carcinoma Diseases 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- 208000027838 paramyotonia congenita of Von Eulenburg Diseases 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 208000035824 paresthesia Diseases 0.000 description 1
- 230000001314 paroxysmal effect Effects 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 210000004197 pelvis Anatomy 0.000 description 1
- NYDXNILOWQXUOF-GXKRWWSZSA-L pemetrexed disodium Chemical compound [Na+].[Na+].C=1NC=2NC(N)=NC(=O)C=2C=1CCC1=CC=C(C(=O)N[C@@H](CCC([O-])=O)C([O-])=O)C=C1 NYDXNILOWQXUOF-GXKRWWSZSA-L 0.000 description 1
- SZFPYBIJACMNJV-UHFFFAOYSA-N perifosine Chemical compound CCCCCCCCCCCCCCCCCCOP([O-])(=O)OC1CC[N+](C)(C)CC1 SZFPYBIJACMNJV-UHFFFAOYSA-N 0.000 description 1
- 229950010632 perifosine Drugs 0.000 description 1
- 208000021999 perineural cyst Diseases 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 208000020930 peroxisome biogenesis disorder 1B Diseases 0.000 description 1
- 208000030591 peroxisome biogenesis disorder type 3B Diseases 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 229940043441 phosphoinositide 3-kinase inhibitor Drugs 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 238000000554 physical therapy Methods 0.000 description 1
- 235000010204 pine bark Nutrition 0.000 description 1
- 235000018192 pine bark supplement Nutrition 0.000 description 1
- 208000024724 pineal body neoplasm Diseases 0.000 description 1
- 201000004123 pineal gland cancer Diseases 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229960003171 plicamycin Drugs 0.000 description 1
- YJGVMLPVUAXIQN-XVVDYKMHSA-N podophyllotoxin Chemical compound COC1=C(OC)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@H](O)[C@@H]3[C@@H]2C(OC3)=O)=C1 YJGVMLPVUAXIQN-XVVDYKMHSA-N 0.000 description 1
- 229960001237 podophyllotoxin Drugs 0.000 description 1
- YVCVYCSAAZQOJI-UHFFFAOYSA-N podophyllotoxin Natural products COC1=C(O)C(OC)=CC(C2C3=CC=4OCOC=4C=C3C(O)C3C2C(OC3)=O)=C1 YVCVYCSAAZQOJI-UHFFFAOYSA-N 0.000 description 1
- 229940093448 poloxamer 124 Drugs 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229940113116 polyethylene glycol 1000 Drugs 0.000 description 1
- 208000005987 polymyositis Diseases 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000004302 potassium sorbate Substances 0.000 description 1
- 235000010241 potassium sorbate Nutrition 0.000 description 1
- 229940069338 potassium sorbate Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 208000018290 primary dysautonomia Diseases 0.000 description 1
- 201000009395 primary hyperaldosteronism Diseases 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 108090000468 progesterone receptors Proteins 0.000 description 1
- 206010036807 progressive multifocal leukoencephalopathy Diseases 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 229950008679 protamine sulfate Drugs 0.000 description 1
- 208000001381 pseudotumor cerebri Diseases 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 229940106796 pycnogenol Drugs 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 206010038038 rectal cancer Diseases 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 201000001275 rectum cancer Diseases 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 230000022983 regulation of cell cycle Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 208000009169 relapsing polychondritis Diseases 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 208000029922 reticulum cell sarcoma Diseases 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 230000001020 rhythmical effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229960001548 salinomycin Drugs 0.000 description 1
- 235000019378 salinomycin Nutrition 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical class O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 208000004548 serous cystadenocarcinoma Diseases 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 201000009890 sinusitis Diseases 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 210000003625 skull Anatomy 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 238000002415 sodium dodecyl sulfate polyacrylamide gel electrophoresis Methods 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(2s,3s,4s,5r,6r)-6-[(2s,3r,4r,5s,6r)-3-acetamido-2-[(2s,3s,4r,5r,6r)-6-[(2r,3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2- Chemical compound [Na+].CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 229960003787 sorafenib Drugs 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 208000018198 spasticity Diseases 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000012289 standard assay Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 208000023366 superficial siderosis Diseases 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 206010042772 syncope Diseases 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000011885 synergistic combination Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 229940036220 synvisc Drugs 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
- 229960001603 tamoxifen Drugs 0.000 description 1
- 229940120982 tarceva Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 210000003582 temporal bone Anatomy 0.000 description 1
- 210000002435 tendon Anatomy 0.000 description 1
- 208000001608 teratocarcinoma Diseases 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 201000006361 tethered spinal cord syndrome Diseases 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 208000001644 thecoma Diseases 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000000015 thermotherapy Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000002053 thietanyl group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical class [H]S* 0.000 description 1
- 206010048627 thoracic outlet syndrome Diseases 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- UJLAWZDWDVHWOW-YPMHNXCESA-N tofacitinib Chemical compound C[C@@H]1CCN(C(=O)CC#N)C[C@@H]1N(C)C1=NC=NC2=C1C=CN2 UJLAWZDWDVHWOW-YPMHNXCESA-N 0.000 description 1
- 229960001350 tofacitinib Drugs 0.000 description 1
- 229940044693 topoisomerase inhibitor Drugs 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 229960004066 trametinib Drugs 0.000 description 1
- LIRYPHYGHXZJBZ-UHFFFAOYSA-N trametinib Chemical compound CC(=O)NC1=CC=CC(N2C(N(C3CC3)C(=O)C3=C(NC=4C(=CC(I)=CC=4)F)N(C)C(=O)C(C)=C32)=O)=C1 LIRYPHYGHXZJBZ-UHFFFAOYSA-N 0.000 description 1
- 230000002463 transducing effect Effects 0.000 description 1
- 201000010875 transient cerebral ischemia Diseases 0.000 description 1
- 206010044412 transitional cell carcinoma Diseases 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 208000009174 transverse myelitis Diseases 0.000 description 1
- 229960000575 trastuzumab Drugs 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000006168 tricyclic group Chemical group 0.000 description 1
- 229940117013 triethanolamine oleate Drugs 0.000 description 1
- 206010044652 trigeminal neuralgia Diseases 0.000 description 1
- 208000022679 triple-negative breast carcinoma Diseases 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- UPCXAARSWVHVLY-UHFFFAOYSA-N tris(2-hydroxyethyl)azanium;acetate Chemical compound CC(O)=O.OCCN(CCO)CCO UPCXAARSWVHVLY-UHFFFAOYSA-N 0.000 description 1
- 201000002311 trypanosomiasis Diseases 0.000 description 1
- 208000009999 tuberous sclerosis Diseases 0.000 description 1
- 201000007423 tubular adenocarcinoma Diseases 0.000 description 1
- 208000022271 tubular adenoma Diseases 0.000 description 1
- 230000005747 tumor angiogenesis Effects 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 210000003454 tympanic membrane Anatomy 0.000 description 1
- 208000032527 type III spinal muscular atrophy Diseases 0.000 description 1
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 1
- 239000005483 tyrosine kinase inhibitor Substances 0.000 description 1
- 241001430294 unidentified retrovirus Species 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 210000003708 urethra Anatomy 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 229960000653 valrubicin Drugs 0.000 description 1
- ZOCKGBMQLCSHFP-KQRAQHLDSA-N valrubicin Chemical compound O([C@H]1C[C@](CC2=C(O)C=3C(=O)C4=CC=CC(OC)=C4C(=O)C=3C(O)=C21)(O)C(=O)COC(=O)CCCC)[C@H]1C[C@H](NC(=O)C(F)(F)F)[C@H](O)[C@H](C)O1 ZOCKGBMQLCSHFP-KQRAQHLDSA-N 0.000 description 1
- 238000007631 vascular surgery Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229960003862 vemurafenib Drugs 0.000 description 1
- GPXBXXGIAQBQNI-UHFFFAOYSA-N vemurafenib Chemical compound CCCS(=O)(=O)NC1=CC=C(F)C(C(=O)C=2C3=CC(=CN=C3NC=2)C=2C=CC(Cl)=CC=2)=C1F GPXBXXGIAQBQNI-UHFFFAOYSA-N 0.000 description 1
- 230000008189 vertebrate development Effects 0.000 description 1
- 208000009540 villous adenoma Diseases 0.000 description 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
- 229960004528 vincristine Drugs 0.000 description 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
- UGGWPQSBPIFKDZ-KOTLKJBCSA-N vindesine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(N)=O)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1N=C1[C]2C=CC=C1 UGGWPQSBPIFKDZ-KOTLKJBCSA-N 0.000 description 1
- 229960004355 vindesine Drugs 0.000 description 1
- CILBMBUYJCWATM-PYGJLNRPSA-N vinorelbine ditartrate Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.OC(=O)[C@H](O)[C@@H](O)C(O)=O.C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC CILBMBUYJCWATM-PYGJLNRPSA-N 0.000 description 1
- 239000001717 vitis vinifera seed extract Substances 0.000 description 1
- 210000003905 vulva Anatomy 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Physical Education & Sports Medicine (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Diabetes (AREA)
- Rheumatology (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychology (AREA)
- Obesity (AREA)
- Oncology (AREA)
- Endocrinology (AREA)
- Gastroenterology & Hepatology (AREA)
- Emergency Medicine (AREA)
- Vascular Medicine (AREA)
- Ophthalmology & Optometry (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Child & Adolescent Psychology (AREA)
- Immunology (AREA)
- Dermatology (AREA)
- Reproductive Health (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361750221P | 2013-01-08 | 2013-01-08 | |
| US61/750,221 | 2013-01-08 | ||
| PCT/US2014/010607 WO2014110086A2 (en) | 2013-01-08 | 2014-01-08 | 3-(benzoimidazol-2-yl)-indazole inhibitors of the wnt signaling pathway and therapeutic uses thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2897400A1 true CA2897400A1 (en) | 2014-07-17 |
Family
ID=51061428
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2897400A Abandoned CA2897400A1 (en) | 2013-01-08 | 2014-01-08 | 3-(benzoimidazol-2-yl)-indazole inhibitors of the wnt signaling pathway and therapeutic uses thereof |
Country Status (7)
| Country | Link |
|---|---|
| US (3) | US9908867B2 (enExample) |
| EP (1) | EP2943198B1 (enExample) |
| JP (1) | JP6355648B2 (enExample) |
| CN (1) | CN105120862A (enExample) |
| CA (1) | CA2897400A1 (enExample) |
| MX (1) | MX370487B (enExample) |
| WO (1) | WO2014110086A2 (enExample) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL2464232T3 (pl) | 2009-08-10 | 2016-04-29 | Samumed Llc | Indazolowe inhibitory szlaku sygnałowego Wnt i ich zastosowania terapeutyczne |
| CA2986631C (en) | 2009-12-21 | 2020-06-02 | Samumed, Llc | 1h-pyrazolo[3,4-.beta.]pyridines and thereapeutic uses thereof |
| DK2755483T3 (en) | 2011-09-14 | 2019-03-11 | Samumed Llc | INDAZOL-3-CARBOXAMIDES AND ITS USE AS WNT / B-CATENIN SIGNAL INHIBITORS |
| PH12017500997A1 (en) | 2012-04-04 | 2018-02-19 | Samumed Llc | Indazole inhibitors of the wnt signal pathway and therapeutic uses thereof |
| JP6209593B2 (ja) | 2012-05-04 | 2017-10-04 | サミュメッド リミテッド ライアビリティ カンパニー | １Ｈ−ピラゾロ［３，４−ｂ］ピリジンおよびそれらの治療的使用 |
| EP2943198B1 (en) | 2013-01-08 | 2019-07-17 | Samumed, LLC | 3-(benzoimidazol-2-yl)-indazole inhibitors of the wnt signaling pathway and therapeutic uses thereof |
| WO2016040182A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 2-(1h-indazol-3-yl)-1h-imidazo[4,5-c]pyridine and therapeutic uses thereof |
| WO2016040188A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(3h-imidazo[4,5-c]pyridin-2-yl)-1h-pyrazolo[3,4-c]pyridine and therapeutic uses thereof |
| WO2016040190A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(3h-imidazo[4,5-b]pyridin-2-yl)-1h-pyrazolo[3,4-b]pyridine and therapeutic uses thereof |
| WO2016040185A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 2-(1h-indazol-3-yl)-3h-imidazo[4,5-b]pyridine and therapeutic uses thereof |
| WO2016040184A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(3h-imidazo[4,5-b]pyridin-2-yl)-1h-pyrazolo[3,4-c]pyridine and therapeutic uses thereof |
| WO2016040181A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(1h-imidazo[4,5-c]pyridin-2-yl)-1h-pyrazolo[3,4-c]pyridine and therapeutic uses thereof |
| WO2016040193A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(1h-imidazo[4,5-c]pyridin-2-yl)-1h-pyrazolo[3,4-b]pyridine and therapeutic uses thereof |
| WO2016040180A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(1h-benzo[d]imidazol-2-yl)-1h-pyrazolo[3,4-c]pyridine and therapeutic uses thereof |
| WO2016133838A1 (en) | 2015-02-20 | 2016-08-25 | Rigel Pharmaceuticals, Inc. | Gdf-8 inhibitors |
| WO2017023993A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(1h-indol-2-yl)-1h-pyrazolo[4,3-b]pyridines and therapeutic uses thereof |
| US10188634B2 (en) | 2015-08-03 | 2019-01-29 | Samumed, Llc | 3-(3H-imidazo[4,5-C]pyridin-2-yl)-1 H-pyrazolo[4,3-B]pyridines and therapeutic uses thereof |
| WO2017023984A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(1h-pyrrolo[3,2-c]pyridin-2-yl)-1h-pyrazolo[3,4-c]pyridines and therapeutic uses thereof |
| WO2017023972A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(1h-imidazo[4,5-c]pyridin-2-yl)-1h-pyrazolo[4,3-b]pyridines and therapeutic uses thereof |
| WO2017024004A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(1h-pyrrolo[2,3-b]pyridin-2-yl)-1h-pyrazolo[4,3-b]pyridines and therapeutic uses thereof |
| WO2017023980A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(1h-pyrrolo[2,3-b]pyridin-2-yl)-1h-pyrazolo[3,4-c]pyridines and therapeutic uses thereof |
| WO2017024003A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc | 3-(1h-pyrrolo[3,2-c]pyridin-2-yl)-1h-pyrazolo[4,3-b]pyridines and therapeutic uses thereof |
| WO2017024015A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(3h-imidazo[4,5-b]pyridin-2-yl)-1h-pyrazolo[4,3-b]pyridines and therapeutic uses thereof |
| US10392383B2 (en) | 2015-08-03 | 2019-08-27 | Samumed, Llc | 3-(1H-benzo[d]imidazol-2-yl)-1H-pyrazolo[4,3-b]pyridines and therapeutic uses thereof |
| WO2017023975A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(1h-pyrrolo[2,3-c]pyridin-2-yl)-1h-pyrazolo[3,4-c]pyridines and therapeutic uses thereof |
| WO2017024025A1 (en) | 2015-08-03 | 2017-02-09 | Sunil Kumar Kc | 3-(1h-pyrrolo[2,3-c]pyridin-2-yl)-1h-pyrazolo[4,3-b]pyridines and therapeutic uses thereof |
| US10463651B2 (en) | 2015-08-03 | 2019-11-05 | Samumed, Llc | 3-(1H-pyrrolo[3,2-C]pyridin-2-YL)-1H-indazoles and therapeutic uses thereof |
| WO2017023987A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(1h-pyrrolo[3,2-c]pyridin-2-yl)-1h-pyrazolo[3,4-b]pyridines and therapeutic uses thereof |
| WO2017023986A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc | 3-(1h-indol-2-yl)-1h-indazoles and therapeutic uses thereof |
| WO2017024026A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc | 3-(1h-indol-2-yl)-1h-pyrazolo[3,4-c]pyridines and therapeutic uses thereof |
| US10350199B2 (en) | 2015-08-03 | 2019-07-16 | Samumed, Llc | 3-(1h-pyrrolo[2,3-b]pyridin-2-yl)-1h-indazoles and therapeutic uses thereof |
| WO2017023996A1 (en) | 2015-08-03 | 2017-02-09 | Samumed, Llc. | 3-(1h-pyrrolo[2,3-b]pyridin-2-yl)-1h-pyrazolo[3,4-b]pyridines and therapeutic uses thereof |
| CA3004297A1 (en) | 2015-11-06 | 2017-05-11 | Samumed, Llc | 2-(1h-indazol-3-yl)-3h-imidazo[4,5-c]pyridines and their anti-inflammatory uses thereof |
| AR108325A1 (es) | 2016-04-27 | 2018-08-08 | Samumed Llc | Isoquinolin-3-il carboxamidas y preparación y uso de las mismas |
| ES2933109T3 (es) | 2016-06-01 | 2023-02-02 | Biosplice Therapeutics Inc | Proceso para preparar N-(5-(3-(7-(3-fluorofenil)-3h-imidazo[4,5-c]piridin-2-il)-1h-indazol-5-il)piridin-3-il)-3-metilbutanamida |
| EP3528808B1 (en) | 2016-10-21 | 2021-10-06 | BioSplice Therapeutics, Inc. | Methods of using indazole-3-carboxamides and their use as wnt/b-catenin signaling pathway inhibitors |
| JP7630905B2 (ja) | 2016-11-07 | 2025-02-18 | バイオスプライス セラピューティクス インコーポレイテッド | 単回用量の調整済み注射用製剤 |
| US10759799B2 (en) | 2018-06-15 | 2020-09-01 | Samumed, Llc | Indazole containing macrocycles and therapeutic uses thereof |
| WO2020150552A2 (en) | 2019-01-17 | 2020-07-23 | Samumed, Llc | Methods of treating cartilage disorders through inhibition of clk and dyrk |
| JP7451765B2 (ja) * | 2020-05-12 | 2024-03-18 | 蘇州阿尓脈生物科技有限公司 | Ｃｄｋ阻害剤としてのピリジンアセトアミド系誘導体、その調製方法及び用途 |
| WO2022012058A1 (zh) * | 2020-07-16 | 2022-01-20 | 江苏凯迪恩医药科技有限公司 | 稠环化合物及其中间体、制备方法和应用 |
| US20230404985A1 (en) * | 2020-11-02 | 2023-12-21 | Icahn School Of Medicine At Mount Sinai | Methods of treating tumors and cancers having dysregulated wnt signaling pathways |
Family Cites Families (138)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4164559A (en) | 1977-09-21 | 1979-08-14 | Cornell Research Foundation, Inc. | Collagen drug delivery device |
| ES8401486A1 (es) | 1981-11-10 | 1983-12-01 | Wellcome Found | Un procedimiento para la preparacion de nuevos derivados de imidazo (4,5-c)piridina. |
| US4474752A (en) | 1983-05-16 | 1984-10-02 | Merck & Co., Inc. | Drug delivery system utilizing thermosetting gels |
| US4783443A (en) | 1986-03-03 | 1988-11-08 | The University Of Chicago | Amino acyl cephalosporin derivatives |
| EP0410509A1 (en) | 1989-07-25 | 1991-01-30 | Duphar International Research B.V | New substituted 1H-indazole-3-carboxamides |
| GB9414139D0 (en) | 1994-07-13 | 1994-08-31 | Smithkline Beecham Plc | Novel compounds |
| US6440102B1 (en) | 1998-07-23 | 2002-08-27 | Durect Corporation | Fluid transfer and diagnostic system for treating the inner ear |
| DE19853299C2 (de) | 1998-11-19 | 2003-04-03 | Thomas Lenarz | Katheter zur Applikation von Medikamenten in Flüssigkeitsräumen des menschlichen Innenohrs |
| US6120484A (en) | 1999-02-17 | 2000-09-19 | Silverstein; Herbert | Otological implant for delivery of medicament and method of using same |
| WO2000071129A1 (en) | 1999-05-21 | 2000-11-30 | Bristol-Myers Squibb Company | Pyrrolotriazine inhibitors of kinases |
| DE50010931D1 (de) | 1999-06-23 | 2005-09-15 | Aventis Pharma Gmbh | Substituierte benzimidazole |
| PE20010306A1 (es) | 1999-07-02 | 2001-03-29 | Agouron Pharma | Compuestos de indazol y composiciones farmaceuticas que los contienen utiles para la inhibicion de proteina kinasa |
| TWI262914B (en) | 1999-07-02 | 2006-10-01 | Agouron Pharma | Compounds and pharmaceutical compositions for inhibiting protein kinases |
| US6844367B1 (en) | 1999-09-17 | 2005-01-18 | Millennium Pharmaceuticals, Inc. | Benzamides and related inhibitors of factor Xa |
| US6967023B1 (en) | 2000-01-10 | 2005-11-22 | Foamix, Ltd. | Pharmaceutical and cosmetic carrier or composition for topical application |
| YU54202A (sh) | 2000-01-18 | 2006-01-16 | Agouron Pharmaceuticals Inc. | Jedinjenja indazola, farmaceutske smeše i postupci za stimulisanje i inhibiranje ćelijske proliferacije |
| US6897231B2 (en) | 2000-07-31 | 2005-05-24 | Signal Pharmaceuticals, Inc. | Indazole derivatives as JNK inhibitors and compositions and methods related thereto |
| US20050009876A1 (en) | 2000-07-31 | 2005-01-13 | Bhagwat Shripad S. | Indazole compounds, compositions thereof and methods of treatment therewith |
| EP1318814B1 (en) | 2000-09-15 | 2007-05-30 | Vertex Pharmaceuticals Incorporated | Triazole compounds useful as protein kinase inhibitors |
| AU2002222293A1 (en) | 2000-12-19 | 2002-07-01 | Smithkline Beecham P.L.C. | Pyrazolo(3,4-c)pyridines as gsk-3 inhibitors |
| US20050192262A1 (en) | 2001-03-13 | 2005-09-01 | Tomas Hagstrom | Treatment of tumours |
| MXPA03009957A (es) | 2001-04-30 | 2005-07-25 | Vertex Pharma | Inhibidores de la gsk-3 y estructuras cristalinas de la proteina gsk-3¦ y complejos de proteina. |
| GB0115109D0 (en) | 2001-06-21 | 2001-08-15 | Aventis Pharma Ltd | Chemical compounds |
| US7642278B2 (en) | 2001-07-03 | 2010-01-05 | Novartis Vaccines And Diagnostics, Inc. | Indazole benzimidazole compounds |
| JP2004536113A (ja) * | 2001-07-03 | 2004-12-02 | カイロン コーポレイション | チロシンキナーゼおよびセリン／スレオニンキナーゼのインヒビターとしてのインダゾールベンズイミダゾール化合物 |
| JP2005538183A (ja) | 2001-09-13 | 2005-12-15 | ジーンソフト ファーマシューティカルズ インコーポレイテッド | 薬剤耐性細菌による感染症の治療方法 |
| US6648873B2 (en) | 2001-09-21 | 2003-11-18 | Durect Corp. | Aural catheter system including anchor balloon and balloon inflation device |
| FR2831536A1 (fr) | 2001-10-26 | 2003-05-02 | Aventis Pharma Sa | Nouveaux derives de benzimidazoles, leur procede de preparation, leur application a titre de medicament, compositions pharmaceutiques et nouvelle utilisation notamment comme inhibiteurs de kdr |
| EP1448557A4 (en) | 2001-10-26 | 2005-02-02 | Univ Connecticut | HETEROINDANE: A NEW CLASS OF HIGH-ACTIVITY CANNABIMIMETIC LIGANDS |
| IL161576A0 (en) | 2001-10-26 | 2004-09-27 | Aventis Pharma Inc | Benzimidazoles and analogues and their use as protein kinases inhibitors |
| US6897208B2 (en) | 2001-10-26 | 2005-05-24 | Aventis Pharmaceuticals Inc. | Benzimidazoles |
| US20030187026A1 (en) | 2001-12-13 | 2003-10-02 | Qun Li | Kinase inhibitors |
| WO2003070706A1 (en) | 2002-02-19 | 2003-08-28 | Pharmacia Corporation | Tricyclic pyrazole derivatives for the treatment of inflammation |
| ES2281633T3 (es) | 2002-02-19 | 2007-10-01 | Pfizer Italia S.R.L. | Derivados triciclicos de pirazol, procedimiento para su preparacion y su uso como agentes antitumorales. |
| EP1506176B1 (en) | 2002-05-17 | 2013-04-24 | Pfizer Italia S.r.l. | Aminoindazole derivatives active as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them |
| CN1656079A (zh) | 2002-05-31 | 2005-08-17 | 卫材株式会社 | 吡唑化合物和含有该化合物的药物组合物 |
| US7449488B2 (en) | 2002-06-04 | 2008-11-11 | Schering Corporation | Pyrazolopyrimidines as protein kinase inhibitors |
| DE60319820T2 (de) | 2002-06-04 | 2009-03-26 | Schering Corp. | Pyrazoloä1,5-aüpyrimidin-verbindungen als antivirale agentien |
| US20050282733A1 (en) | 2002-06-27 | 2005-12-22 | Prins Johannes B | Differentiation modulating agents and uses therefor |
| GB0218625D0 (en) | 2002-08-10 | 2002-09-18 | Astex Technology Ltd | Pharmaceutical compounds |
| FR2845382A1 (fr) | 2002-10-02 | 2004-04-09 | Sanofi Synthelabo | Derives d'indazolecarboxamides, leur preparation et leur utilisation en therapeutique |
| ATE481402T1 (de) | 2003-02-27 | 2010-10-15 | Palau Pharma Sa | Pyrazolopyridin-derivate |
| US7135575B2 (en) | 2003-03-03 | 2006-11-14 | Array Biopharma, Inc. | P38 inhibitors and methods of use thereof |
| EP1644371B1 (en) | 2003-07-03 | 2008-02-13 | Aventis Pharmaceuticals Inc. | Pyrazoloisoquinoline derivatives as kinase inhibitors |
| GT200400136A (es) | 2003-07-30 | 2005-05-02 | Compuestos de indazol 3,5-disustituidos, composiciones farmaceuticas y metodos para intervenir en o inhibirlaproliferacion celular. | |
| US7008953B2 (en) | 2003-07-30 | 2006-03-07 | Agouron Pharmaceuticals, Inc. | 3, 5 Disubstituted indazole compounds, pharmaceutical compositions, and methods for mediating or inhibiting cell proliferation |
| US20050090529A1 (en) | 2003-07-31 | 2005-04-28 | Pfizer Inc | 3,5 Disubstituted indazole compounds with nitrogen-bearing 5-membered heterocycles, pharmaceutical compositions, and methods for mediating or inhibiting cell proliferation |
| WO2005014554A1 (en) | 2003-08-08 | 2005-02-17 | Astex Therapeutics Limited | 1h-indazole-3-carboxamide compounds as mapkap kinase modulators |
| US8969372B2 (en) | 2003-11-14 | 2015-03-03 | Aptose Boisciences Inc. | Aryl imidazoles and their use as anti-cancer agents |
| EP1532980A1 (en) | 2003-11-24 | 2005-05-25 | Novo Nordisk A/S | N-heteroaryl indole carboxamides and analogues thereof, for use as glucokinase activators in the treatment of diabetes |
| FR2864084B1 (fr) | 2003-12-17 | 2006-02-10 | Aventis Pharma Sa | Nouveaux derives organophosphores des indazoles et leur utilisation comme medicaments |
| FR2867778B1 (fr) | 2004-03-16 | 2006-06-09 | Sanofi Synthelabo | Utilisation de derives d'indazolecarboxamides pour la preparation d'un medicament destine au traitement et a la prevention du paludisme |
| EP2336128A1 (en) | 2004-03-25 | 2011-06-22 | Memory Pharmaceuticals Corporation | Benzoisothiazoles and preparation and uses thereof |
| WO2006001894A1 (en) | 2004-04-22 | 2006-01-05 | Memory Pharmaceutical Corporation | Indoles, 1h-indazoles, 1,2-benzisoxazoles, 1,2-benzoisothiazoles, and preparation and uses thereof |
| US20060074102A1 (en) | 2004-05-14 | 2006-04-06 | Kevin Cusack | Kinase inhibitors as therapeutic agents |
| JP2008505167A (ja) | 2004-07-05 | 2008-02-21 | アステックス、セラピューティックス、リミテッド | 医薬組成物 |
| US7626021B2 (en) | 2004-07-27 | 2009-12-01 | Sgx Pharmaceuticals, Inc. | Fused ring heterocycle kinase modulators |
| BRPI0513899A (pt) | 2004-07-27 | 2008-05-20 | Sgx Pharmaceuticals Inc | moduladores de cinase heterocìclica de anel fundido |
| TW200618800A (en) | 2004-08-03 | 2006-06-16 | Uriach Y Compania S A J | Heterocyclic compounds |
| WO2006024945A1 (en) | 2004-09-03 | 2006-03-09 | Pfizer Inc. | Pharmaceutical compositions comprising a cdk inhibitor |
| US7652043B2 (en) | 2004-09-29 | 2010-01-26 | The Johns Hopkins University | WNT pathway antagonists |
| US20060116519A1 (en) | 2004-11-17 | 2006-06-01 | Agouron Pharmaceuticals, Inc. | Synthesis of 5-bromo-4-methyl-pyridin-3-ylmethyl)-ethyl-carbamic acid tert-butyl ester |
| WO2006054143A1 (en) | 2004-11-17 | 2006-05-26 | Pfizer Inc. | Polymorphs of {5-[3-(4,6-difluoro-1h-benzoimidazol-2-yl)-1h-indazol-5-yl]-4-methyl-pyridin-3-ylmethyl}-ethyl-amine |
| US20060127388A1 (en) | 2004-12-10 | 2006-06-15 | Wyeth | Variants of glycogen synthase kinase 3 and uses thereof |
| US20060142247A1 (en) | 2004-12-17 | 2006-06-29 | Guy Georges | Tricyclic heterocycles |
| CA2594963A1 (en) | 2005-01-24 | 2006-07-27 | Neurosystec Corporation | Apparatus and method for delivering therapeutic and/or other agents to the inner ear and to other tissues |
| WO2006130673A1 (en) | 2005-05-31 | 2006-12-07 | Janssen Pharmaceutica, N.V. | 3-benzoimidazolyl-pyrazolopyridines useful in treating kinase disorders |
| MX2008002588A (es) | 2005-08-25 | 2008-03-18 | Hoffmann La Roche | Inhibidores de p38-map-cinasa y los metodos para utilizarlos. |
| US8106066B2 (en) | 2005-09-23 | 2012-01-31 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, pyrazolopyridines, isothiazolopyridines, and preparation and uses thereof |
| UY29825A1 (es) | 2005-10-03 | 2007-05-31 | Astrazeneca Ab | Derivados sustituidos de 3h-imidazol-(4,5 b (beta))piridina-2-il benzoatos y benzamidas, composiciones farmacéuticas que los contienen y aplicaciones |
| TW200804338A (en) | 2005-11-24 | 2008-01-16 | Astrazeneca Ab | New compounds |
| GB0602178D0 (en) | 2006-02-03 | 2006-03-15 | Merck Sharp & Dohme | Therapeutic treatment |
| EP2001882A1 (en) | 2006-03-23 | 2008-12-17 | F. Hoffmann-La Roche AG | Substituted indazole derivatives, their manufacture and use as pharmaceutical agents |
| CA2644910C (en) | 2006-03-31 | 2014-01-28 | Abbott Laboratories | Indazole compounds |
| JP2009541268A (ja) | 2006-06-22 | 2009-11-26 | ビオヴィトルム・アクチボラゲット（プブリクト） | Ｍｎｋキナーゼ阻害剤としてのピリジンおよびピラジン誘導体 |
| WO2008061109A2 (en) | 2006-11-15 | 2008-05-22 | Forest Laboratories Holdings Limited | Indazole derivatives useful as melanin concentrating receptor ligands |
| EP1932830A1 (en) | 2006-12-11 | 2008-06-18 | The Genetics Company, Inc. | Sulfonamides and their use as a medicament |
| EP1932834B1 (en) | 2006-12-11 | 2011-04-27 | The Genetics Company, Inc. | Aromatic 1,4-DI-Carboxylamides and their use |
| AU2007331676A1 (en) | 2006-12-14 | 2008-06-19 | Bayer Schering Pharma Aktiengesellschaft | Dihydropyridine derivatives useful as protein kinase inhibitors |
| CN101679436A (zh) | 2007-04-10 | 2010-03-24 | Sgx药品公司 | 稠环杂环激酶调节剂 |
| WO2008137408A1 (en) | 2007-04-30 | 2008-11-13 | Genentech, Inc. | Pyrazole inhibitors of wnt signaling |
| CN101730531A (zh) | 2007-05-10 | 2010-06-09 | 阿瓦隆药品公司 | 芴、蒽、呫吨、二苯并环庚酮和吖啶的衍生物及其用途 |
| US20080287452A1 (en) | 2007-05-16 | 2008-11-20 | Wyeth | Heteroaryl/aryl pyrimidine analogs and their use as agonists of the wnt-beta-catenin cellular messaging system |
| US8304408B2 (en) | 2007-05-24 | 2012-11-06 | The Regents Of The University Of California | Wnt signaling inhibitors, and methods for making and using them |
| CL2008001540A1 (es) | 2007-05-29 | 2009-05-22 | Sgx Pharmaceuticals Inc | Compuestos derivados de pirrolopiridinas y pirazolopiridinas; composicion farmaceutica; y uso en el tratamiento del cancer. |
| WO2008150845A1 (en) | 2007-05-31 | 2008-12-11 | Vanderbilt University | Screening for wnt pathway modulators and pyrvinium for the treatment of cance |
| KR20100032886A (ko) | 2007-06-08 | 2010-03-26 | 아보트 러보러터리즈 | 키나제 억제제로서의 5-헤테로아릴 치환된 인다졸 |
| US8648069B2 (en) | 2007-06-08 | 2014-02-11 | Abbvie Inc. | 5-substituted indazoles as kinase inhibitors |
| JP2011502958A (ja) | 2007-06-19 | 2011-01-27 | 武田薬品工業株式会社 | グルコキナーゼ活性化インダゾール化合物 |
| FR2917735B1 (fr) | 2007-06-21 | 2009-09-04 | Sanofi Aventis Sa | Nouveaux indazoles substitutes, leur preparation et leur utilisation en therapeutique |
| WO2009011850A2 (en) | 2007-07-16 | 2009-01-22 | Abbott Laboratories | Novel therapeutic compounds |
| EP2182984A2 (en) | 2007-08-02 | 2010-05-12 | Nerviano Medical Sciences S.r.l. | A morpholinyl anthracycline derivative combined with protein kinase inhibitors |
| US20090069319A1 (en) | 2007-08-27 | 2009-03-12 | Wyeth | Imidazopyridine analogs and their use as agonists of the wnt-beta-catenin cellular messaging system |
| WO2009061345A2 (en) | 2007-11-07 | 2009-05-14 | Cornell Research Foundation, Inc. | Targeting cdk4 and cdk6 in cancer therapy |
| KR101061599B1 (ko) | 2008-12-05 | 2011-09-02 | 한국과학기술연구원 | 비정상 세포 성장 질환의 치료를 위한 단백질 키나아제 저해제인 신규 인다졸 유도체, 이의 약학적으로 허용가능한염 및 이를 유효성분으로 함유하는 약학적 조성물 |
| CN101440092B (zh) | 2008-12-25 | 2010-11-17 | 浙江大学 | 2-吲唑-4-氮杂吲哚-5-氨基衍生物及制备和应用 |
| CA2755253A1 (en) | 2009-03-18 | 2010-09-23 | Schering Corporation | Bicyclic compounds as inhibitors of diacylglycerol acyltransferase |
| AU2010229144B2 (en) | 2009-03-23 | 2012-07-12 | Merck Sharp & Dohme Corp. | P2X3, receptor antagonists for treatment of pain |
| WO2011011722A1 (en) | 2009-07-23 | 2011-01-27 | Vanderbilt University | Substituted benzoimidazolesulfonamides and substituted indolesulfonamides as mglur4 potentiators |
| WO2011019648A1 (en) | 2009-08-10 | 2011-02-17 | Epitherix, Llc | Indazoles as wnt/b-catenin signaling pathway inhibitors and therapeutic uses thereof |
| PL2464232T3 (pl) | 2009-08-10 | 2016-04-29 | Samumed Llc | Indazolowe inhibitory szlaku sygnałowego Wnt i ich zastosowania terapeutyczne |
| WO2011050245A1 (en) | 2009-10-23 | 2011-04-28 | Yangbo Feng | Bicyclic heteroaryls as kinase inhibitors |
| CA2986631C (en) * | 2009-12-21 | 2020-06-02 | Samumed, Llc | 1h-pyrazolo[3,4-.beta.]pyridines and thereapeutic uses thereof |
| NZ601376A (en) | 2009-12-21 | 2014-03-28 | Array Biopharma Inc | Substituted n-(1h-indazol-4-yl)imidazo[1, 2-a]pyridine-3- carboxamide compounds as cfms inhibitors |
| KR101792895B1 (ko) | 2010-04-06 | 2017-11-02 | 피터 맥칼룸 캔서 인스티튜트 | 방사선 보호 화합물 및 방법 |
| DE102010043379A1 (de) | 2010-11-04 | 2012-05-10 | Bayer Schering Pharma Aktiengesellschaft | Substituierte 6-Fluor-1H-Pyrazolo[4,3-b]pyridine und ihre Verwendung |
| WO2012068589A2 (en) | 2010-11-19 | 2012-05-24 | Constellation Pharmaceuticals | Modulators of methyl modifying enzymes, compositions and uses thereof |
| PL2663561T3 (pl) | 2011-01-13 | 2016-10-31 | Nowe pochodne heterocykliczne i ich zastosowanie w leczeniu zaburzeń neurologicznych | |
| US8889684B2 (en) | 2011-02-02 | 2014-11-18 | Boehringer Ingelheim International Gmbh | Azaindolylphenyl sulfonamides as serine/threonine kinase inhibitors |
| WO2012129562A2 (en) | 2011-03-24 | 2012-09-27 | The Scripps Research Institute | Compounds and methods for inducing chondrogenesis |
| EP2694060A4 (en) | 2011-04-01 | 2014-09-10 | Univ Utah Res Found | SUBSTITUTED 3- (1H-BENZO- {D} -IMIDAZOL-2-YL-) 1H-INDAZOL ANALOGUE AS PDK1 KINASE INHIBITOR |
| HK1199255A1 (en) | 2011-08-12 | 2015-06-26 | F. Hoffmann-La Roche Ag | Indazole compounds, compositions and methods of use |
| WO2013024002A1 (en) | 2011-08-12 | 2013-02-21 | F. Hoffmann-La Roche Ag | PYRAZOLO[3,4-c]PYRIDINE COMPOUNDS AND METHODS OF USE |
| RU2673064C2 (ru) | 2011-09-01 | 2018-11-22 | Ф. Хоффманн-Ля Рош Аг | Пирролопиразиновые ингибиторы киназы |
| DK2755483T3 (en) | 2011-09-14 | 2019-03-11 | Samumed Llc | INDAZOL-3-CARBOXAMIDES AND ITS USE AS WNT / B-CATENIN SIGNAL INHIBITORS |
| US9290427B2 (en) | 2012-01-30 | 2016-03-22 | Universiteit Gent | Anti-invasive compounds |
| US20150087687A1 (en) | 2012-03-23 | 2015-03-26 | Dennis Brown | Compositions and methods to improve the therapeutic benefit of indirubin and analogs thereof, including meisoindigo |
| PH12017500997A1 (en) | 2012-04-04 | 2018-02-19 | Samumed Llc | Indazole inhibitors of the wnt signal pathway and therapeutic uses thereof |
| US9056874B2 (en) | 2012-05-04 | 2015-06-16 | Novartis Ag | Complement pathway modulators and uses thereof |
| JP6209593B2 (ja) | 2012-05-04 | 2017-10-04 | サミュメッド リミテッド ライアビリティ カンパニー | １Ｈ−ピラゾロ［３，４−ｂ］ピリジンおよびそれらの治療的使用 |
| MX2014013430A (es) | 2012-05-04 | 2015-04-14 | Basf Se | Compuestos que contienen pirazol sustituido y su uso como plaguicidas. |
| EP2943198B1 (en) | 2013-01-08 | 2019-07-17 | Samumed, LLC | 3-(benzoimidazol-2-yl)-indazole inhibitors of the wnt signaling pathway and therapeutic uses thereof |
| US9327886B2 (en) | 2013-03-13 | 2016-05-03 | Bayer Healthcare Llc | Vial container with collar cap |
| PE20170127A1 (es) | 2014-03-20 | 2017-03-30 | Samumed Llc | Indazol-3-carboxamidas 5-sustituidas y preparacion y uso de las mismas |
| WO2016040184A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(3h-imidazo[4,5-b]pyridin-2-yl)-1h-pyrazolo[3,4-c]pyridine and therapeutic uses thereof |
| WO2016040181A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(1h-imidazo[4,5-c]pyridin-2-yl)-1h-pyrazolo[3,4-c]pyridine and therapeutic uses thereof |
| WO2016040188A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(3h-imidazo[4,5-c]pyridin-2-yl)-1h-pyrazolo[3,4-c]pyridine and therapeutic uses thereof |
| WO2016040193A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(1h-imidazo[4,5-c]pyridin-2-yl)-1h-pyrazolo[3,4-b]pyridine and therapeutic uses thereof |
| WO2016040185A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 2-(1h-indazol-3-yl)-3h-imidazo[4,5-b]pyridine and therapeutic uses thereof |
| WO2016040190A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(3h-imidazo[4,5-b]pyridin-2-yl)-1h-pyrazolo[3,4-b]pyridine and therapeutic uses thereof |
| WO2016040182A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 2-(1h-indazol-3-yl)-1h-imidazo[4,5-c]pyridine and therapeutic uses thereof |
| US9538272B2 (en) | 2014-09-08 | 2017-01-03 | Apple Inc. | Acoustic mesh and methods of use for electronic devices |
| WO2016040180A1 (en) | 2014-09-08 | 2016-03-17 | Samumed, Llc | 3-(1h-benzo[d]imidazol-2-yl)-1h-pyrazolo[3,4-c]pyridine and therapeutic uses thereof |
| US10350199B2 (en) | 2015-08-03 | 2019-07-16 | Samumed, Llc | 3-(1h-pyrrolo[2,3-b]pyridin-2-yl)-1h-indazoles and therapeutic uses thereof |
| CA3004297A1 (en) | 2015-11-06 | 2017-05-11 | Samumed, Llc | 2-(1h-indazol-3-yl)-3h-imidazo[4,5-c]pyridines and their anti-inflammatory uses thereof |
| ES2933109T3 (es) | 2016-06-01 | 2023-02-02 | Biosplice Therapeutics Inc | Proceso para preparar N-(5-(3-(7-(3-fluorofenil)-3h-imidazo[4,5-c]piridin-2-il)-1h-indazol-5-il)piridin-3-il)-3-metilbutanamida |
| EP3528808B1 (en) | 2016-10-21 | 2021-10-06 | BioSplice Therapeutics, Inc. | Methods of using indazole-3-carboxamides and their use as wnt/b-catenin signaling pathway inhibitors |
| JP7630905B2 (ja) | 2016-11-07 | 2025-02-18 | バイオスプライス セラピューティクス インコーポレイテッド | 単回用量の調整済み注射用製剤 |
-
2014
- 2014-01-08 EP EP14737972.1A patent/EP2943198B1/en active Active
- 2014-01-08 CN CN201480013031.9A patent/CN105120862A/zh active Pending
- 2014-01-08 MX MX2015008860A patent/MX370487B/es active IP Right Grant
- 2014-01-08 US US14/149,948 patent/US9908867B2/en active Active
- 2014-01-08 JP JP2015551853A patent/JP6355648B2/ja active Active
- 2014-01-08 CA CA2897400A patent/CA2897400A1/en not_active Abandoned
- 2014-01-08 WO PCT/US2014/010607 patent/WO2014110086A2/en not_active Ceased
-
2018
- 2018-02-06 US US15/889,403 patent/US10183929B2/en active Active
-
2019
- 2019-01-18 US US16/252,055 patent/US10654832B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US20180162840A1 (en) | 2018-06-14 |
| EP2943198A2 (en) | 2015-11-18 |
| MX2015008860A (es) | 2016-04-04 |
| WO2014110086A3 (en) | 2014-10-09 |
| JP2016504387A (ja) | 2016-02-12 |
| US20140194441A1 (en) | 2014-07-10 |
| WO2014110086A2 (en) | 2014-07-17 |
| US10654832B2 (en) | 2020-05-19 |
| CN105120862A (zh) | 2015-12-02 |
| EP2943198A4 (en) | 2016-08-03 |
| US20190352279A1 (en) | 2019-11-21 |
| EP2943198B1 (en) | 2019-07-17 |
| MX370487B (es) | 2019-12-16 |
| US9908867B2 (en) | 2018-03-06 |
| US10183929B2 (en) | 2019-01-22 |
| JP6355648B2 (ja) | 2018-07-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US10654832B2 (en) | 3-(benzoimidazol-2-YL)-indazole inhibitors of the Wnt signaling pathway and therapeutic uses thereof | |
| AU2016203274B2 (en) | Indazole inhibitors of the wnt signal pathway and therapeutic uses thereof | |
| CA2848659C (en) | Indazole-3-carboxamides and their use as wnt/b-catenin signaling pathway inhibitors | |
| EP2770994B1 (en) | 1h-pyrazolo[3,4-b]pyridines and therapeutic uses thereof | |
| US10226453B2 (en) | 3-(1H-indol-2-yl)-1H-pyrazolo[4,3-B]pyridines and therapeutic uses thereof | |
| CA3022002A1 (en) | Isoquinolin-3-yl carboxamides and preparation and use thereof | |
| WO2016040184A1 (en) | 3-(3h-imidazo[4,5-b]pyridin-2-yl)-1h-pyrazolo[3,4-c]pyridine and therapeutic uses thereof | |
| HK1197724B (en) | 1h-pyrazolo[3,4-b]pyridines and therapeutic uses thereof | |
| HK1193946A (en) | Indazole-3-carboxamides and their use as wnt/b-cantenin signaling pathway inhibitors | |
| HK1193946B (en) | Indazole-3-carboxamides and their use as wnt/b-cantenin signaling pathway inhibitors |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20190108 |
|
| FZDE | Discontinued |
Effective date: 20210831 |