JP5432982B2 - アポトーシスシグナル調節キナーゼ１阻害剤 - Google Patents
アポトーシスシグナル調節キナーゼ１阻害剤 Download PDFInfo
- Publication number
- JP5432982B2 JP5432982B2 JP2011503082A JP2011503082A JP5432982B2 JP 5432982 B2 JP5432982 B2 JP 5432982B2 JP 2011503082 A JP2011503082 A JP 2011503082A JP 2011503082 A JP2011503082 A JP 2011503082A JP 5432982 B2 JP5432982 B2 JP 5432982B2
- Authority
- JP
- Japan
- Prior art keywords
- pyrimidin
- benzamide
- pyrazolo
- hydroxypropan
- alkyl
- 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.)
- Expired - Fee Related
Links
- 229940127254 ASK1 inhibitor Drugs 0.000 title description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 504
- -1 cyano, thio, oxy, carbonyloxy Chemical group 0.000 claims description 405
- 125000000217 alkyl group Chemical group 0.000 claims description 358
- 125000003118 aryl group Chemical group 0.000 claims description 287
- 150000001875 compounds Chemical class 0.000 claims description 283
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 227
- 125000001424 substituent group Chemical group 0.000 claims description 155
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 117
- GWMBGNCOGKPDQP-MRXNPFEDSA-N n-[7-[(3r)-3-aminopiperidin-1-yl]pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2C[C@H](N)CCC2)=C1 GWMBGNCOGKPDQP-MRXNPFEDSA-N 0.000 claims description 99
- 239000001257 hydrogen Substances 0.000 claims description 97
- 229910052739 hydrogen Inorganic materials 0.000 claims description 97
- 102100033127 Mitogen-activated protein kinase kinase kinase 5 Human genes 0.000 claims description 85
- 125000005843 halogen group Chemical group 0.000 claims description 83
- 125000004104 aryloxy group Chemical group 0.000 claims description 79
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 77
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 68
- 201000010099 disease Diseases 0.000 claims description 66
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 59
- 125000001072 heteroaryl group Chemical group 0.000 claims description 58
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 56
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 56
- 150000003839 salts Chemical class 0.000 claims description 51
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 49
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
- 125000003282 alkyl amino group Chemical group 0.000 claims description 43
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 42
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 40
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 39
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 35
- 125000005188 oxoalkyl group Chemical group 0.000 claims description 31
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 30
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 24
- VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 claims description 24
- 239000003814 drug Substances 0.000 claims description 20
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 20
- 150000003857 carboxamides Chemical class 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 18
- 206010012601 diabetes mellitus Diseases 0.000 claims description 18
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 18
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 17
- 125000000304 alkynyl group Chemical group 0.000 claims description 17
- 150000001408 amides Chemical class 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 229940124530 sulfonamide Drugs 0.000 claims description 16
- 150000003456 sulfonamides Chemical class 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 15
- 208000028867 ischemia Diseases 0.000 claims description 15
- 125000004043 oxo group Chemical group O=* 0.000 claims description 15
- 108090000623 proteins and genes Proteins 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 13
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 13
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 12
- 230000006907 apoptotic process Effects 0.000 claims description 12
- 125000005605 benzo group Chemical group 0.000 claims description 12
- 230000002401 inhibitory effect Effects 0.000 claims description 12
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 12
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 12
- 230000004770 neurodegeneration Effects 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 125000004076 pyridyl group Chemical group 0.000 claims description 11
- 206010007572 Cardiac hypertrophy Diseases 0.000 claims description 10
- 208000006029 Cardiomegaly Diseases 0.000 claims description 10
- 230000001404 mediated effect Effects 0.000 claims description 10
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 10
- 208000020084 Bone disease Diseases 0.000 claims description 9
- 206010021143 Hypoxia Diseases 0.000 claims description 9
- 208000002193 Pain Diseases 0.000 claims description 9
- 208000006011 Stroke Diseases 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 230000007954 hypoxia Effects 0.000 claims description 9
- 208000010125 myocardial infarction Diseases 0.000 claims description 9
- 230000036407 pain Effects 0.000 claims description 9
- 102000004169 proteins and genes Human genes 0.000 claims description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 8
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 8
- 230000001575 pathological effect Effects 0.000 claims description 8
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 7
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 7
- 229910019142 PO4 Inorganic materials 0.000 claims description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 230000028993 immune response Effects 0.000 claims description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
- 230000010410 reperfusion Effects 0.000 claims description 7
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 6
- NZKQPTGAIWWVMH-UHFFFAOYSA-N 4-tert-butyl-n-[7-[3-(hydroxymethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=C(CO)C=CC=2)=C1 NZKQPTGAIWWVMH-UHFFFAOYSA-N 0.000 claims description 6
- 208000023275 Autoimmune disease Diseases 0.000 claims description 6
- 208000011231 Crohn disease Diseases 0.000 claims description 6
- 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 claims description 6
- 208000002705 Glucose Intolerance Diseases 0.000 claims description 6
- 206010019280 Heart failures Diseases 0.000 claims description 6
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 6
- 108090000190 Thrombin Proteins 0.000 claims description 6
- 206010008118 cerebral infarction Diseases 0.000 claims description 6
- 230000001066 destructive effect Effects 0.000 claims description 6
- 206010020718 hyperplasia Diseases 0.000 claims description 6
- 208000027866 inflammatory disease Diseases 0.000 claims description 6
- 208000014674 injury Diseases 0.000 claims description 6
- 210000004185 liver Anatomy 0.000 claims description 6
- 208000030159 metabolic disease Diseases 0.000 claims description 6
- 201000006417 multiple sclerosis Diseases 0.000 claims description 6
- 208000031225 myocardial ischemia Diseases 0.000 claims description 6
- IVHRSJVMGRUVQH-UHFFFAOYSA-N n-[7-[3-(hydroxymethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=C(CO)C=CC=2)=C1 IVHRSJVMGRUVQH-UHFFFAOYSA-N 0.000 claims description 6
- 210000000056 organ Anatomy 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 125000005499 phosphonyl group Chemical group 0.000 claims description 6
- 201000009104 prediabetes syndrome Diseases 0.000 claims description 6
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 229960004072 thrombin Drugs 0.000 claims description 6
- 230000002792 vascular Effects 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- 208000035473 Communicable disease Diseases 0.000 claims description 5
- 208000002249 Diabetes Complications Diseases 0.000 claims description 5
- 101001018196 Homo sapiens Mitogen-activated protein kinase kinase kinase 5 Proteins 0.000 claims description 5
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 5
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 5
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- 230000001939 inductive effect Effects 0.000 claims description 5
- 208000015181 infectious disease Diseases 0.000 claims description 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
- 208000019423 liver disease Diseases 0.000 claims description 5
- 125000002757 morpholinyl group Chemical group 0.000 claims description 5
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 5
- 239000010452 phosphate Substances 0.000 claims description 5
- 125000003386 piperidinyl group Chemical group 0.000 claims description 5
- 230000000770 proinflammatory effect Effects 0.000 claims description 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 230000008736 traumatic injury Effects 0.000 claims description 5
- 125000004306 triazinyl group Chemical group 0.000 claims description 5
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 5
- ZJPHAQGVIJMSTQ-MRXNPFEDSA-N (3r)-1-[5-[[4-(2-hydroxypropan-2-yl)benzoyl]amino]pyrazolo[1,5-a]pyrimidin-7-yl]-n-methylpiperidine-3-carboxamide Chemical compound C1[C@H](C(=O)NC)CCCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 ZJPHAQGVIJMSTQ-MRXNPFEDSA-N 0.000 claims description 4
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 4
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- KVWJNXPPFSNYLH-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-(3-oxopiperazin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CC(=O)NCC2)=C1 KVWJNXPPFSNYLH-UHFFFAOYSA-N 0.000 claims description 4
- QGGXIKUPMBWBTH-UHFFFAOYSA-N 4-tert-butyl-n-[7-(pyrimidin-2-ylamino)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(NC=2N=CC=CN=2)=C1 QGGXIKUPMBWBTH-UHFFFAOYSA-N 0.000 claims description 4
- KQIGTFWLIXVUHK-UHFFFAOYSA-N 4-tert-butyl-n-[7-[4-fluoro-3-(hydroxymethyl)phenyl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=C(C=2C=C(CO)C(F)=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)C)C=C1 KQIGTFWLIXVUHK-UHFFFAOYSA-N 0.000 claims description 4
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 4
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 4
- 206010020772 Hypertension Diseases 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 239000008103 glucose Substances 0.000 claims description 4
- 229930195712 glutamate Natural products 0.000 claims description 4
- 208000014951 hematologic disease Diseases 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- TZGFASURQDCAHW-UHFFFAOYSA-N n-[7-(4-acetamidopiperidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-2-pyridin-4-ylcyclopropane-1-carboxamide Chemical compound C1CC(NC(=O)C)CCN1C1=CC(NC(=O)C2C(C2)C=2C=CN=CC=2)=NC2=CC(C)=NN12 TZGFASURQDCAHW-UHFFFAOYSA-N 0.000 claims description 4
- JPKSVPDOAXTDGA-UHFFFAOYSA-N n-[7-[4-(hydroxymethyl)piperidin-1-yl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(N2CCC(CO)CC2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 JPKSVPDOAXTDGA-UHFFFAOYSA-N 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 208000023504 respiratory system disease Diseases 0.000 claims description 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 208000014001 urinary system disease Diseases 0.000 claims description 4
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- LWTQUQNSRBLAGG-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-(3-methylpiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1C(C)CCCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 LWTQUQNSRBLAGG-UHFFFAOYSA-N 0.000 claims description 3
- 208000010444 Acidosis Diseases 0.000 claims description 3
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
- 206010002383 Angina Pectoris Diseases 0.000 claims description 3
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 3
- 206010055128 Autoimmune neutropenia Diseases 0.000 claims description 3
- 208000023328 Basedow disease Diseases 0.000 claims description 3
- 201000006474 Brain Ischemia Diseases 0.000 claims description 3
- 206010058019 Cancer Pain Diseases 0.000 claims description 3
- 206010008111 Cerebral haemorrhage Diseases 0.000 claims description 3
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 3
- 206010008909 Chronic Hepatitis Diseases 0.000 claims description 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
- 208000000668 Chronic Pancreatitis Diseases 0.000 claims description 3
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 3
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 3
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 3
- 206010070901 Diabetic dyslipidaemia Diseases 0.000 claims description 3
- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 3
- 241000255925 Diptera Species 0.000 claims description 3
- 208000004232 Enteritis Diseases 0.000 claims description 3
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 3
- 206010018364 Glomerulonephritis Diseases 0.000 claims description 3
- 208000009329 Graft vs Host Disease Diseases 0.000 claims description 3
- 208000015023 Graves' disease Diseases 0.000 claims description 3
- 206010018910 Haemolysis Diseases 0.000 claims description 3
- 206010019233 Headaches Diseases 0.000 claims description 3
- 208000016988 Hemorrhagic Stroke Diseases 0.000 claims description 3
- 206010019755 Hepatitis chronic active Diseases 0.000 claims description 3
- 208000023105 Huntington disease Diseases 0.000 claims description 3
- 206010020751 Hypersensitivity Diseases 0.000 claims description 3
- 208000007976 Ketosis Diseases 0.000 claims description 3
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 3
- 206010027417 Metabolic acidosis Diseases 0.000 claims description 3
- 208000034578 Multiple myelomas Diseases 0.000 claims description 3
- HRMVKGNVXHNGII-UHFFFAOYSA-N N-(2-hydroxypropan-2-yl)benzamide Chemical compound CC(C)(O)NC(=O)c1ccccc1 HRMVKGNVXHNGII-UHFFFAOYSA-N 0.000 claims description 3
- 206010029350 Neurotoxicity Diseases 0.000 claims description 3
- 208000008589 Obesity Diseases 0.000 claims description 3
- 206010030113 Oedema Diseases 0.000 claims description 3
- 208000001132 Osteoporosis Diseases 0.000 claims description 3
- 206010033645 Pancreatitis Diseases 0.000 claims description 3
- 206010033647 Pancreatitis acute Diseases 0.000 claims description 3
- 206010033649 Pancreatitis chronic Diseases 0.000 claims description 3
- 208000018737 Parkinson disease Diseases 0.000 claims description 3
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 3
- 201000004681 Psoriasis Diseases 0.000 claims description 3
- 206010037660 Pyrexia Diseases 0.000 claims description 3
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 3
- 206010039710 Scleroderma Diseases 0.000 claims description 3
- 206010040047 Sepsis Diseases 0.000 claims description 3
- 206010040070 Septic Shock Diseases 0.000 claims description 3
- 206010049416 Short-bowel syndrome Diseases 0.000 claims description 3
- 208000021386 Sjogren Syndrome Diseases 0.000 claims description 3
- 230000006044 T cell activation Effects 0.000 claims description 3
- 206010043781 Thyroiditis chronic Diseases 0.000 claims description 3
- 206010044221 Toxic encephalopathy Diseases 0.000 claims description 3
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 3
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 230000001154 acute effect Effects 0.000 claims description 3
- 201000003229 acute pancreatitis Diseases 0.000 claims description 3
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 3
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 3
- 208000026935 allergic disease Diseases 0.000 claims description 3
- 230000007815 allergy Effects 0.000 claims description 3
- 230000036592 analgesia Effects 0.000 claims description 3
- 208000007502 anemia Diseases 0.000 claims description 3
- 235000021229 appetite regulation Nutrition 0.000 claims description 3
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 3
- 230000002917 arthritic effect Effects 0.000 claims description 3
- 201000008937 atopic dermatitis Diseases 0.000 claims description 3
- 230000001363 autoimmune Effects 0.000 claims description 3
- 201000005000 autoimmune gastritis Diseases 0.000 claims description 3
- 230000001580 bacterial effect Effects 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 210000004369 blood Anatomy 0.000 claims description 3
- 239000008280 blood Substances 0.000 claims description 3
- 208000026106 cerebrovascular disease Diseases 0.000 claims description 3
- 238000002512 chemotherapy Methods 0.000 claims description 3
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 3
- 208000001848 dysentery Diseases 0.000 claims description 3
- 206010015037 epilepsy Diseases 0.000 claims description 3
- 208000024908 graft versus host disease Diseases 0.000 claims description 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
- 231100000869 headache Toxicity 0.000 claims description 3
- 230000008588 hemolysis Effects 0.000 claims description 3
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 208000020658 intracerebral hemorrhage Diseases 0.000 claims description 3
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 3
- 230000004140 ketosis Effects 0.000 claims description 3
- 208000017169 kidney disease Diseases 0.000 claims description 3
- 206010028417 myasthenia gravis Diseases 0.000 claims description 3
- 230000002232 neuromuscular Effects 0.000 claims description 3
- 231100000228 neurotoxicity Toxicity 0.000 claims description 3
- 230000007135 neurotoxicity Effects 0.000 claims description 3
- 235000020824 obesity Nutrition 0.000 claims description 3
- 201000008482 osteoarthritis Diseases 0.000 claims description 3
- 108010040003 polyglutamine Proteins 0.000 claims description 3
- 229920000155 polyglutamine Polymers 0.000 claims description 3
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 3
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- 230000036303 septic shock Effects 0.000 claims description 3
- 208000003265 stomatitis Diseases 0.000 claims description 3
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 3
- 206010043554 thrombocytopenia Diseases 0.000 claims description 3
- 208000004371 toothache Diseases 0.000 claims description 3
- XLOOFDPJOQWACG-RBUKOAKNSA-N (1r,2r)-n-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)-2-phenylcyclopropane-1-carboxamide Chemical compound C1([C@@H]2C[C@H]2C(=O)NC2=NC3=CC(=NN3C(C=3C=CC=CC=3)=C2)C)=CC=CC=C1 XLOOFDPJOQWACG-RBUKOAKNSA-N 0.000 claims description 2
- FRSRKJPAVRXSCG-JKSUJKDBSA-N (1r,2r)-n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)-2-phenylcyclopropane-1-carboxamide Chemical compound O=C([C@H]1[C@@H](C1)C=1C=CC=CC=1)NC(=NC1=CC=NN11)C=C1N1CCOCC1 FRSRKJPAVRXSCG-JKSUJKDBSA-N 0.000 claims description 2
- BAQLCCJCNPZGRP-VQTJNVASSA-N (1r,2r)-n-[7-(4-acetamidopiperidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-2-phenylcyclopropane-1-carboxamide Chemical compound C1CC(NC(=O)C)CCN1C1=CC(NC(=O)[C@H]2[C@@H](C2)C=2C=CC=CC=2)=NC2=CC(C)=NN12 BAQLCCJCNPZGRP-VQTJNVASSA-N 0.000 claims description 2
- IPILMVZMVZJPLW-ZWKOTPCHSA-N (1r,2r)-n-[7-[4-(carbamoylamino)piperidin-1-yl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-2-phenylcyclopropane-1-carboxamide Chemical compound C1([C@@H]2C[C@H]2C(=O)NC2=NC3=CC(=NN3C(N3CCC(CC3)NC(N)=O)=C2)C)=CC=CC=C1 IPILMVZMVZJPLW-ZWKOTPCHSA-N 0.000 claims description 2
- XLOOFDPJOQWACG-RTBURBONSA-N (1r,2s)-n-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)-2-phenylcyclopropane-1-carboxamide Chemical compound C1([C@H]2C[C@H]2C(=O)NC2=NC3=CC(=NN3C(C=3C=CC=CC=3)=C2)C)=CC=CC=C1 XLOOFDPJOQWACG-RTBURBONSA-N 0.000 claims description 2
- XLOOFDPJOQWACG-MOPGFXCFSA-N (1s,2s)-n-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)-2-phenylcyclopropane-1-carboxamide Chemical compound C1([C@H]2C[C@@H]2C(=O)NC2=NC3=CC(=NN3C(C=3C=CC=CC=3)=C2)C)=CC=CC=C1 XLOOFDPJOQWACG-MOPGFXCFSA-N 0.000 claims description 2
- BAQLCCJCNPZGRP-UXHICEINSA-N (1s,2s)-n-[7-(4-acetamidopiperidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-2-phenylcyclopropane-1-carboxamide Chemical compound C1CC(NC(=O)C)CCN1C1=CC(NC(=O)[C@@H]2[C@H](C2)C=2C=CC=CC=2)=NC2=CC(C)=NN12 BAQLCCJCNPZGRP-UXHICEINSA-N 0.000 claims description 2
- RZQSKBIYHQMWIB-QGZVFWFLSA-N (3r)-1-[5-[[4-(2-hydroxypropan-2-yl)benzoyl]amino]-2-methylpyrazolo[1,5-a]pyrimidin-7-yl]-n-methylpiperidine-3-carboxamide Chemical compound C1[C@H](C(=O)NC)CCCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC(C)=NN12 RZQSKBIYHQMWIB-QGZVFWFLSA-N 0.000 claims description 2
- LTFBCTANUOPSBW-GOSISDBHSA-N (3r)-1-[5-[[4-(2-hydroxypropan-2-yl)benzoyl]amino]pyrazolo[1,5-a]pyrimidin-7-yl]-n-propan-2-ylpiperidine-3-carboxamide Chemical compound C1[C@H](C(=O)NC(C)C)CCCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 LTFBCTANUOPSBW-GOSISDBHSA-N 0.000 claims description 2
- BKCNNMYHBNECKH-OAHLLOKOSA-N (3r)-1-[5-[[4-(2-hydroxypropan-2-yl)benzoyl]amino]pyrazolo[1,5-a]pyrimidin-7-yl]piperidine-3-carboxylic acid Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2C[C@@H](CCC2)C(O)=O)=C1 BKCNNMYHBNECKH-OAHLLOKOSA-N 0.000 claims description 2
- GPXQNYUONOMDOY-QGZVFWFLSA-N (3r)-n-ethyl-1-[5-[[4-(2-hydroxypropan-2-yl)benzoyl]amino]pyrazolo[1,5-a]pyrimidin-7-yl]piperidine-3-carboxamide Chemical compound C1[C@H](C(=O)NCC)CCCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 GPXQNYUONOMDOY-QGZVFWFLSA-N 0.000 claims description 2
- ZJPHAQGVIJMSTQ-INIZCTEOSA-N (3s)-1-[5-[[4-(2-hydroxypropan-2-yl)benzoyl]amino]pyrazolo[1,5-a]pyrimidin-7-yl]-n-methylpiperidine-3-carboxamide Chemical compound C1[C@@H](C(=O)NC)CCCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 ZJPHAQGVIJMSTQ-INIZCTEOSA-N 0.000 claims description 2
- BKCNNMYHBNECKH-HNNXBMFYSA-N (3s)-1-[5-[[4-(2-hydroxypropan-2-yl)benzoyl]amino]pyrazolo[1,5-a]pyrimidin-7-yl]piperidine-3-carboxylic acid Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2C[C@H](CCC2)C(O)=O)=C1 BKCNNMYHBNECKH-HNNXBMFYSA-N 0.000 claims description 2
- ZGCWHLPQHRVEKW-UHFFFAOYSA-N 1-[4-[(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)carbamoyl]phenyl]cyclopropane-1-carboxylic acid Chemical compound C=1C=C(C(=O)NC2=NC3=CC=NN3C(N3CCOCC3)=C2)C=CC=1C1(C(=O)O)CC1 ZGCWHLPQHRVEKW-UHFFFAOYSA-N 0.000 claims description 2
- YUISYQIJJQLJCV-UHFFFAOYSA-N 1-[5-[(4-tert-butylbenzoyl)amino]pyrazolo[1,5-a]pyrimidin-7-yl]piperidine-3-carboxylic acid Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CC(CCC2)C(O)=O)=C1 YUISYQIJJQLJCV-UHFFFAOYSA-N 0.000 claims description 2
- KSSDNVNCLYKHCQ-UHFFFAOYSA-N 1-[5-[[4-(2-hydroxypropan-2-yl)benzoyl]amino]-2-methylpyrazolo[1,5-a]pyrimidin-7-yl]-n,n-dimethylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)CCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC(C)=NN12 KSSDNVNCLYKHCQ-UHFFFAOYSA-N 0.000 claims description 2
- XXVGSBPYGOMYKH-UHFFFAOYSA-N 1-[5-[[4-(2-hydroxypropan-2-yl)benzoyl]amino]-2-methylpyrazolo[1,5-a]pyrimidin-7-yl]-n-methylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)NC)CCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC(C)=NN12 XXVGSBPYGOMYKH-UHFFFAOYSA-N 0.000 claims description 2
- RHGCWVWHOXYCMZ-UHFFFAOYSA-N 1-[5-[[4-(2-hydroxypropan-2-yl)benzoyl]amino]-2-methylpyrazolo[1,5-a]pyrimidin-7-yl]piperidine-4-carboxylic acid Chemical compound C1=C(N2CCC(CC2)C(O)=O)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 RHGCWVWHOXYCMZ-UHFFFAOYSA-N 0.000 claims description 2
- ZYJXXPCIMQNSQF-UHFFFAOYSA-N 1-[5-[[4-(2-hydroxypropan-2-yl)benzoyl]amino]pyrazolo[1,5-a]pyrimidin-7-yl]-n-methylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)NC)CCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 ZYJXXPCIMQNSQF-UHFFFAOYSA-N 0.000 claims description 2
- MNISJJFFUWARPH-UHFFFAOYSA-N 1-[5-[[4-(2-hydroxypropan-2-yl)benzoyl]amino]pyrazolo[1,5-a]pyrimidin-7-yl]-n-propan-2-ylpiperidine-4-carboxamide Chemical compound C1CC(C(=O)NC(C)C)CCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 MNISJJFFUWARPH-UHFFFAOYSA-N 0.000 claims description 2
- PYVKMUJGAZLWQH-UHFFFAOYSA-N 1-[5-[[4-(2-hydroxypropan-2-yl)benzoyl]amino]pyrazolo[1,5-a]pyrimidin-7-yl]piperidine-4-carboxylic acid Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CCC(CC2)C(O)=O)=C1 PYVKMUJGAZLWQH-UHFFFAOYSA-N 0.000 claims description 2
- KCONEQZFBFDXJP-UHFFFAOYSA-N 1-hydroxy-n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)naphthalene-2-carboxamide Chemical compound C1=CC2=CC=CC=C2C(O)=C1C(=O)NC(=NC1=CC=NN11)C=C1N1CCOCC1 KCONEQZFBFDXJP-UHFFFAOYSA-N 0.000 claims description 2
- WAEGCCBZAWXMOP-UHFFFAOYSA-N 2-[3-[5-[[4-(2-hydroxypropan-2-yl)benzoyl]amino]pyrazolo[1,5-a]pyrimidin-7-yl]phenoxy]acetic acid Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=C(OCC(O)=O)C=CC=2)=C1 WAEGCCBZAWXMOP-UHFFFAOYSA-N 0.000 claims description 2
- PYYFYZRKFYCTAZ-UHFFFAOYSA-N 2-[[2-methyl-2-[4-[(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)carbamoyl]phenyl]propyl]amino]-2-oxoacetic acid Chemical compound C1=C(C=2C=CC=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)CNC(=O)C(O)=O)C=C1 PYYFYZRKFYCTAZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 2
- VMHHMQQXKJBDGE-UHFFFAOYSA-N 4-(1-amino-2-methylpropan-2-yl)-n-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide Chemical compound C1=C(C=2C=CC=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)CN)C=C1 VMHHMQQXKJBDGE-UHFFFAOYSA-N 0.000 claims description 2
- BOOKHCVZOHXOLE-UHFFFAOYSA-N 4-(1-hydroxy-2-methylpropan-2-yl)-n-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide Chemical compound C1=C(C=2C=CC=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)CO)C=C1 BOOKHCVZOHXOLE-UHFFFAOYSA-N 0.000 claims description 2
- JCHMBIBDBRODQQ-UHFFFAOYSA-N 4-(1-hydroxy-2-methylpropan-2-yl)-n-(2-methyl-7-pyrrolidin-1-ylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide Chemical compound C1=C(N2CCCC2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)CO)C=C1 JCHMBIBDBRODQQ-UHFFFAOYSA-N 0.000 claims description 2
- ODJOUCPQPQRYRQ-UHFFFAOYSA-N 4-(1-hydroxy-2-methylpropan-2-yl)-n-[7-[3-(methoxymethyl)phenyl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound COCC1=CC=CC(C=2N3N=C(C)C=C3N=C(NC(=O)C=3C=CC(=CC=3)C(C)(C)CO)C=2)=C1 ODJOUCPQPQRYRQ-UHFFFAOYSA-N 0.000 claims description 2
- XTSRLYKXOHTBGF-UHFFFAOYSA-N 4-(2-cyanopropan-2-yl)-n-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide Chemical compound C1=C(C=2C=CC=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)C#N)C=C1 XTSRLYKXOHTBGF-UHFFFAOYSA-N 0.000 claims description 2
- OSDDNNPBRQNISI-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-(2-methyl-7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide Chemical compound C1=C(N2CCOCC2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 OSDDNNPBRQNISI-UHFFFAOYSA-N 0.000 claims description 2
- NGZAJKWVMZWUFX-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide Chemical compound C1=C(C=2C=CC=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 NGZAJKWVMZWUFX-UHFFFAOYSA-N 0.000 claims description 2
- OVPICIBYTKOPMZ-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-(2-methyl-7-piperidin-1-ylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide Chemical compound C1=C(N2CCCCC2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 OVPICIBYTKOPMZ-UHFFFAOYSA-N 0.000 claims description 2
- HKHIVSYMVWKKEA-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-(2-methyl-7-thiomorpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide Chemical compound C1=C(N2CCSCC2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 HKHIVSYMVWKKEA-UHFFFAOYSA-N 0.000 claims description 2
- YTWQRKMZEKXYSV-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-(7-methoxypyrazolo[1,5-a]pyrimidin-5-yl)benzamide Chemical compound N=1C2=CC=NN2C(OC)=CC=1NC(=O)C1=CC=C(C(C)(C)O)C=C1 YTWQRKMZEKXYSV-UHFFFAOYSA-N 0.000 claims description 2
- OXVBTSJFGMBZFV-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-(7-phenoxypyrazolo[1,5-a]pyrimidin-5-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(OC=2C=CC=CC=2)=C1 OXVBTSJFGMBZFV-UHFFFAOYSA-N 0.000 claims description 2
- YLYLLTNGHOFLIG-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-(7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=CC=CC=2)=C1 YLYLLTNGHOFLIG-UHFFFAOYSA-N 0.000 claims description 2
- APLAAFISJBTNIA-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-(7-thiophen-3-ylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C2=CSC=C2)=C1 APLAAFISJBTNIA-UHFFFAOYSA-N 0.000 claims description 2
- KOGIONJHVPHPIB-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[2-methyl-7-(1-oxo-2,8-diazaspiro[4.5]decan-8-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=C(N2CCC3(C(NCC3)=O)CC2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 KOGIONJHVPHPIB-UHFFFAOYSA-N 0.000 claims description 2
- ITKXZGZKFZXPLB-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[2-methyl-7-(4-phenylsulfanylpiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=C(N2CCC(CC2)SC=2C=CC=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 ITKXZGZKFZXPLB-UHFFFAOYSA-N 0.000 claims description 2
- BIWGPJYGUGRDLO-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[2-methyl-7-(4-propylsulfonylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1CN(S(=O)(=O)CCC)CCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC(C)=NN12 BIWGPJYGUGRDLO-UHFFFAOYSA-N 0.000 claims description 2
- KLJNBSULFBQFJK-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[2-methyl-7-(6-propan-2-yloxypyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=NC(OC(C)C)=CC=C1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC(C)=NN12 KLJNBSULFBQFJK-UHFFFAOYSA-N 0.000 claims description 2
- ANKJBSSCXNQEKJ-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-(1,2,3,4-tetrahydroisoquinolin-7-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=C3CNCCC3=CC=2)=C1 ANKJBSSCXNQEKJ-UHFFFAOYSA-N 0.000 claims description 2
- NOVFWODZQVVUGJ-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-(2-methylpiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound CC1CCCCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 NOVFWODZQVVUGJ-UHFFFAOYSA-N 0.000 claims description 2
- PJYCQQGNLHYTHL-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-(2-methylpyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound CC1CCCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 PJYCQQGNLHYTHL-UHFFFAOYSA-N 0.000 claims description 2
- UTQFIAIILHWSTK-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-(3-hydroxypyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CC(O)CC2)=C1 UTQFIAIILHWSTK-UHFFFAOYSA-N 0.000 claims description 2
- DREIQYKBZWYTTC-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-(3-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound COC1=CC=CC(C=2N3N=C(C)C=C3N=C(NC(=O)C=3C=CC(=CC=3)C(C)(C)O)C=2)=C1 DREIQYKBZWYTTC-UHFFFAOYSA-N 0.000 claims description 2
- SRXIBYPKYPCTMH-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-(3-methoxyphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound COC1=CC=CC(C=2N3N=CC=C3N=C(NC(=O)C=3C=CC(=CC=3)C(C)(C)O)C=2)=C1 SRXIBYPKYPCTMH-UHFFFAOYSA-N 0.000 claims description 2
- CXNLSEXHNRULTH-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-(3-methyl-4-oxopiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1CC(=O)C(C)CN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 CXNLSEXHNRULTH-UHFFFAOYSA-N 0.000 claims description 2
- LMMYZNOEEXDQBA-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-(3-phenylmethoxyphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=C1 LMMYZNOEEXDQBA-UHFFFAOYSA-N 0.000 claims description 2
- NQYVHLCKYWSMSX-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-(4-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(OC)=CC=C1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC(C)=NN12 NQYVHLCKYWSMSX-UHFFFAOYSA-N 0.000 claims description 2
- OYNMFNCYDOPWTG-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(OC)=CC=C1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 OYNMFNCYDOPWTG-UHFFFAOYSA-N 0.000 claims description 2
- XZYCQIFJSCKTNO-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-(4-methoxypiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1CC(OC)CCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 XZYCQIFJSCKTNO-UHFFFAOYSA-N 0.000 claims description 2
- BSPRRNSOYRFXSQ-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-(4-methyl-1,4-diazepan-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1CN(C)CCCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 BSPRRNSOYRFXSQ-UHFFFAOYSA-N 0.000 claims description 2
- YMTIHLQIJIRXCY-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-(5-oxo-1,4-diazepan-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CCC(=O)NCC2)=C1 YMTIHLQIJIRXCY-UHFFFAOYSA-N 0.000 claims description 2
- XYEWZZXJIJERKJ-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-(6-methoxypyridin-3-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=NC(OC)=CC=C1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC(C)=NN12 XYEWZZXJIJERKJ-UHFFFAOYSA-N 0.000 claims description 2
- PGFAEWVVIPQMHG-QGZVFWFLSA-N 4-(2-hydroxypropan-2-yl)-n-[7-[(2r)-2-(methoxymethyl)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound COC[C@H]1CCCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 PGFAEWVVIPQMHG-QGZVFWFLSA-N 0.000 claims description 2
- AIQHDRCALMTPEL-MRXNPFEDSA-N 4-(2-hydroxypropan-2-yl)-n-[7-[(3r)-3-hydroxypyrrolidin-1-yl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=C(N2C[C@H](O)CC2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 AIQHDRCALMTPEL-MRXNPFEDSA-N 0.000 claims description 2
- QMTVONRIZNAICT-MDWZMJQESA-N 4-(2-hydroxypropan-2-yl)-n-[7-[(e)-2-phenylethenyl]pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(\C=C\C=2C=CC=CC=2)=C1 QMTVONRIZNAICT-MDWZMJQESA-N 0.000 claims description 2
- FILSZLVHAPATHA-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-[3-(methoxymethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound COCC1=CC=CC(C=2N3N=CC=C3N=C(NC(=O)C=3C=CC(=CC=3)C(C)(C)O)C=2)=C1 FILSZLVHAPATHA-UHFFFAOYSA-N 0.000 claims description 2
- NKAYQECUWQGJRS-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-[4-(2-hydroxypropan-2-yl)piperidin-1-yl]pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1CC(C(C)(O)C)CCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 NKAYQECUWQGJRS-UHFFFAOYSA-N 0.000 claims description 2
- RWJQUEHUOPEFAJ-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-[4-(2-methoxyethoxy)phenyl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(OCCOC)=CC=C1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC(C)=NN12 RWJQUEHUOPEFAJ-UHFFFAOYSA-N 0.000 claims description 2
- IKFQRDUEJYZEIP-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-[4-(methoxymethyl)piperidin-1-yl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1CC(COC)CCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC(C)=NN12 IKFQRDUEJYZEIP-UHFFFAOYSA-N 0.000 claims description 2
- HSNFRHHGMPPLLU-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-[4-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=CC(=CC=2)C(F)(F)F)=C1 HSNFRHHGMPPLLU-UHFFFAOYSA-N 0.000 claims description 2
- KPAMBRUDIQVBEP-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-[4-(trifluoromethyl)piperidin-1-yl]pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CCC(CC2)C(F)(F)F)=C1 KPAMBRUDIQVBEP-UHFFFAOYSA-N 0.000 claims description 2
- POFLOXDHDATTRX-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-phenyl-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC(C(F)(F)F)=NN2C(C=2C=CC=CC=2)=C1 POFLOXDHDATTRX-UHFFFAOYSA-N 0.000 claims description 2
- VEWMKHGIRZXZKY-UHFFFAOYSA-N 4-bromo-n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide Chemical compound C1=CC(Br)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CCOCC2)=C1 VEWMKHGIRZXZKY-UHFFFAOYSA-N 0.000 claims description 2
- LBULRDWVNGYSHF-UHFFFAOYSA-N 4-tert-butyl-n-(7-imidazol-1-ylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2C=NC=C2)=C1 LBULRDWVNGYSHF-UHFFFAOYSA-N 0.000 claims description 2
- QIKBRXBBYPUZBQ-UHFFFAOYSA-N 4-tert-butyl-n-(7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=CC=CC=2)=C1 QIKBRXBBYPUZBQ-UHFFFAOYSA-N 0.000 claims description 2
- PHILPEMWGYVCIT-UHFFFAOYSA-N 4-tert-butyl-n-[7-(1,2,4-triazol-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2N=CN=C2)=C1 PHILPEMWGYVCIT-UHFFFAOYSA-N 0.000 claims description 2
- GFQOGZZSSZKYHK-UHFFFAOYSA-N 4-tert-butyl-n-[7-(2,4-dimethoxyphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound COC1=CC(OC)=CC=C1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)C)=NC2=CC=NN12 GFQOGZZSSZKYHK-UHFFFAOYSA-N 0.000 claims description 2
- JKFGYALKQVWZDY-UHFFFAOYSA-N 4-tert-butyl-n-[7-(2-chlorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C(=CC=CC=2)Cl)=C1 JKFGYALKQVWZDY-UHFFFAOYSA-N 0.000 claims description 2
- GAVOASGNDXRVRH-UHFFFAOYSA-N 4-tert-butyl-n-[7-(2-formylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C(=CC=CC=2)C=O)=C1 GAVOASGNDXRVRH-UHFFFAOYSA-N 0.000 claims description 2
- KPJVNRMXDNWSFO-UHFFFAOYSA-N 4-tert-butyl-n-[7-(2-methoxyethylamino)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound N=1C2=CC=NN2C(NCCOC)=CC=1NC(=O)C1=CC=C(C(C)(C)C)C=C1 KPJVNRMXDNWSFO-UHFFFAOYSA-N 0.000 claims description 2
- ODPUAGJIBBRIJH-UHFFFAOYSA-N 4-tert-butyl-n-[7-(2-methoxypyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound COC1=NC=CC=C1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)C)=NC2=CC=NN12 ODPUAGJIBBRIJH-UHFFFAOYSA-N 0.000 claims description 2
- USPWFJWYPKWCLK-UHFFFAOYSA-N 4-tert-butyl-n-[7-(2-phenoxyethylamino)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(NCCOC=2C=CC=CC=2)=C1 USPWFJWYPKWCLK-UHFFFAOYSA-N 0.000 claims description 2
- QVBVJQMPIRTUJN-UHFFFAOYSA-N 4-tert-butyl-n-[7-(2-phenylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C(=CC=CC=2)C=2C=CC=CC=2)=C1 QVBVJQMPIRTUJN-UHFFFAOYSA-N 0.000 claims description 2
- ZHTQWKPMADUEFF-UHFFFAOYSA-N 4-tert-butyl-n-[7-(3,4-difluorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=C(F)C(F)=CC=2)=C1 ZHTQWKPMADUEFF-UHFFFAOYSA-N 0.000 claims description 2
- RAQNRGCLEGPOHO-UHFFFAOYSA-N 4-tert-butyl-n-[7-(3,5-dimethylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound CC1=CC(C)=CC(C=2N3N=CC=C3N=C(NC(=O)C=3C=CC(=CC=3)C(C)(C)C)C=2)=C1 RAQNRGCLEGPOHO-UHFFFAOYSA-N 0.000 claims description 2
- LSPXXOHJLRYSRV-UHFFFAOYSA-N 4-tert-butyl-n-[7-(3-hydroxypiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CC(O)CCC2)=C1 LSPXXOHJLRYSRV-UHFFFAOYSA-N 0.000 claims description 2
- TZPPYSZHTGWMKS-UHFFFAOYSA-N 4-tert-butyl-n-[7-(3-hydroxypropylamino)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(NCCCO)=C1 TZPPYSZHTGWMKS-UHFFFAOYSA-N 0.000 claims description 2
- HSOYZOIVKYYGTM-UHFFFAOYSA-N 4-tert-butyl-n-[7-(3-hydroxypyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CC(O)CC2)=C1 HSOYZOIVKYYGTM-UHFFFAOYSA-N 0.000 claims description 2
- JKKIGCZARYAMFG-UHFFFAOYSA-N 4-tert-butyl-n-[7-(3-methoxyphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound COC1=CC=CC(C=2N3N=CC=C3N=C(NC(=O)C=3C=CC(=CC=3)C(C)(C)C)C=2)=C1 JKKIGCZARYAMFG-UHFFFAOYSA-N 0.000 claims description 2
- MILCJMXNKSNBTK-UHFFFAOYSA-N 4-tert-butyl-n-[7-(3-nitrophenyl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=C(C=CC=2)[N+]([O-])=O)=C1 MILCJMXNKSNBTK-UHFFFAOYSA-N 0.000 claims description 2
- LXYFLKWLGKPGOG-UHFFFAOYSA-N 4-tert-butyl-n-[7-(4-chlorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=CC(Cl)=CC=2)=C1 LXYFLKWLGKPGOG-UHFFFAOYSA-N 0.000 claims description 2
- MZUYCOFUVHGZFL-UHFFFAOYSA-N 4-tert-butyl-n-[7-(4-cyanophenyl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=CC(=CC=2)C#N)=C1 MZUYCOFUVHGZFL-UHFFFAOYSA-N 0.000 claims description 2
- DUIMBAIULWGJKO-UHFFFAOYSA-N 4-tert-butyl-n-[7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=CC(F)=CC=2)=C1 DUIMBAIULWGJKO-UHFFFAOYSA-N 0.000 claims description 2
- RZOHZHZOPCADBL-UHFFFAOYSA-N 4-tert-butyl-n-[7-(4-hydroxy-4-phenylpiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CCC(O)(CC2)C=2C=CC=CC=2)=C1 RZOHZHZOPCADBL-UHFFFAOYSA-N 0.000 claims description 2
- OXCOVKSGFGBSQU-UHFFFAOYSA-N 4-tert-butyl-n-[7-(4-hydroxypiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CCC(O)CC2)=C1 OXCOVKSGFGBSQU-UHFFFAOYSA-N 0.000 claims description 2
- XCSFIACUGGJIKJ-UHFFFAOYSA-N 4-tert-butyl-n-[7-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(OC)=CC=C1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)C)=NC2=CC=NN12 XCSFIACUGGJIKJ-UHFFFAOYSA-N 0.000 claims description 2
- QNNUSWCEBWNUJO-UHFFFAOYSA-N 4-tert-butyl-n-[7-(4-methylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1CN(C)CCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)C)=NC2=CC=NN12 QNNUSWCEBWNUJO-UHFFFAOYSA-N 0.000 claims description 2
- XIBIODINBXRDDU-UHFFFAOYSA-N 4-tert-butyl-n-[7-(4-nitrophenyl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=CC(=CC=2)[N+]([O-])=O)=C1 XIBIODINBXRDDU-UHFFFAOYSA-N 0.000 claims description 2
- VEGHSZICXQEFIE-UHFFFAOYSA-N 4-tert-butyl-n-[7-(4-tert-butylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=CC(=CC=2)C(C)(C)C)=C1 VEGHSZICXQEFIE-UHFFFAOYSA-N 0.000 claims description 2
- ZDHYFYMUKGVPEL-UHFFFAOYSA-N 4-tert-butyl-n-[7-(6-methoxypyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=NC(OC)=CC=C1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)C)=NC2=CC=NN12 ZDHYFYMUKGVPEL-UHFFFAOYSA-N 0.000 claims description 2
- DVNZEQRXXDVELY-UHFFFAOYSA-N 4-tert-butyl-n-[7-(butylamino)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound N=1C2=CC=NN2C(NCCCC)=CC=1NC(=O)C1=CC=C(C(C)(C)C)C=C1 DVNZEQRXXDVELY-UHFFFAOYSA-N 0.000 claims description 2
- YALAORSZVILFSC-UHFFFAOYSA-N 4-tert-butyl-n-[7-(cyclohexylmethylamino)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(NCC2CCCCC2)=C1 YALAORSZVILFSC-UHFFFAOYSA-N 0.000 claims description 2
- DRZYAHVBFWAONA-UHFFFAOYSA-N 4-tert-butyl-n-[7-(cyclopentylamino)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(NC2CCCC2)=C1 DRZYAHVBFWAONA-UHFFFAOYSA-N 0.000 claims description 2
- HZORMGCQJDHTIK-UHFFFAOYSA-N 4-tert-butyl-n-[7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(NC2CC2)=C1 HZORMGCQJDHTIK-UHFFFAOYSA-N 0.000 claims description 2
- JJDHGGAIJYKFNC-UHFFFAOYSA-N 4-tert-butyl-n-[7-(dimethylamino)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound N=1C2=CC=NN2C(N(C)C)=CC=1NC(=O)C1=CC=C(C(C)(C)C)C=C1 JJDHGGAIJYKFNC-UHFFFAOYSA-N 0.000 claims description 2
- NDQWQKJEBNOQCE-UHFFFAOYSA-N 4-tert-butyl-n-[7-(furan-2-ylmethylamino)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(NCC=2OC=CC=2)=C1 NDQWQKJEBNOQCE-UHFFFAOYSA-N 0.000 claims description 2
- FAXYRGOXLZGWBV-UHFFFAOYSA-N 4-tert-butyl-n-[7-(pentan-3-ylamino)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound N=1C2=CC=NN2C(NC(CC)CC)=CC=1NC(=O)C1=CC=C(C(C)(C)C)C=C1 FAXYRGOXLZGWBV-UHFFFAOYSA-N 0.000 claims description 2
- HZZMATOQGSWDFW-UHFFFAOYSA-N 4-tert-butyl-n-[7-(pyridin-2-ylamino)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(NC=2N=CC=CC=2)=C1 HZZMATOQGSWDFW-UHFFFAOYSA-N 0.000 claims description 2
- UVOHEMVDQVAVBY-UHFFFAOYSA-N 4-tert-butyl-n-[7-(pyridin-3-ylamino)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(NC=2C=NC=CC=2)=C1 UVOHEMVDQVAVBY-UHFFFAOYSA-N 0.000 claims description 2
- AAMQEOGQXKZZRO-UHFFFAOYSA-N 4-tert-butyl-n-[7-(pyridin-3-ylmethylamino)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(NCC=2C=NC=CC=2)=C1 AAMQEOGQXKZZRO-UHFFFAOYSA-N 0.000 claims description 2
- IEWLQCJWAIWRJR-UHFFFAOYSA-N 4-tert-butyl-n-[7-(tert-butylamino)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound N=1C2=CC=NN2C(NC(C)(C)C)=CC=1NC(=O)C1=CC=C(C(C)(C)C)C=C1 IEWLQCJWAIWRJR-UHFFFAOYSA-N 0.000 claims description 2
- HXFJRNZGMYTRSP-UHFFFAOYSA-N 4-tert-butyl-n-[7-[(5-methylpyrazin-2-yl)methylamino]pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=NC(C)=CN=C1CNC1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)C)=NC2=CC=NN12 HXFJRNZGMYTRSP-UHFFFAOYSA-N 0.000 claims description 2
- AKTIJGMSODGSIQ-UHFFFAOYSA-N 4-tert-butyl-n-[7-[2-(1h-indol-3-yl)ethylamino]pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(NCCC=2C3=CC=CC=C3NC=2)=C1 AKTIJGMSODGSIQ-UHFFFAOYSA-N 0.000 claims description 2
- UCYHNGAUFTZDHW-UHFFFAOYSA-N 4-tert-butyl-n-[7-[2-(dimethylamino)ethylamino]pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound N=1C2=CC=NN2C(NCCN(C)C)=CC=1NC(=O)C1=CC=C(C(C)(C)C)C=C1 UCYHNGAUFTZDHW-UHFFFAOYSA-N 0.000 claims description 2
- AJUNSMICDHYDQG-UHFFFAOYSA-N 4-tert-butyl-n-[7-[2-(hydroxymethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C(=CC=CC=2)CO)=C1 AJUNSMICDHYDQG-UHFFFAOYSA-N 0.000 claims description 2
- AKOJMXMYIUUJCL-UHFFFAOYSA-N 4-tert-butyl-n-[7-[3-(2-hydroxyethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=C(CCO)C=CC=2)=C1 AKOJMXMYIUUJCL-UHFFFAOYSA-N 0.000 claims description 2
- IOXPZRQYRWZMPL-UHFFFAOYSA-N 4-tert-butyl-n-[7-[3-(2-oxopyrrolidin-1-yl)propylamino]pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(NCCCN2C(CCC2)=O)=C1 IOXPZRQYRWZMPL-UHFFFAOYSA-N 0.000 claims description 2
- VXWSNNCZTMZVHO-UHFFFAOYSA-N 4-tert-butyl-n-[7-[3-(3-hydroxypropyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=C(CCCO)C=CC=2)=C1 VXWSNNCZTMZVHO-UHFFFAOYSA-N 0.000 claims description 2
- UJTRYEYDVZTAQG-UHFFFAOYSA-N 4-tert-butyl-n-[7-[3-(hydroxymethyl)phenyl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=C(C=2C=C(CO)C=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)C)C=C1 UJTRYEYDVZTAQG-UHFFFAOYSA-N 0.000 claims description 2
- NLFZRFFYKBAVFV-UHFFFAOYSA-N 4-tert-butyl-n-[7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=C(C=CC=2)C(F)(F)F)=C1 NLFZRFFYKBAVFV-UHFFFAOYSA-N 0.000 claims description 2
- KYAVFHWLASSVPW-UHFFFAOYSA-N 4-tert-butyl-n-[7-[4-(2-hydroxyethyl)piperidin-1-yl]pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CCC(CCO)CC2)=C1 KYAVFHWLASSVPW-UHFFFAOYSA-N 0.000 claims description 2
- YCWXLRRXPIAACI-UHFFFAOYSA-N 4-tert-butyl-n-[7-[4-(trifluoromethoxy)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=CC(OC(F)(F)F)=CC=2)=C1 YCWXLRRXPIAACI-UHFFFAOYSA-N 0.000 claims description 2
- WKOYXLKFUWYNDP-UHFFFAOYSA-O CC1=NN2C(=C1)N=C(C=C2OC(=O)N3CC[S+](CC3)O)NC(=O)C4=CC=C(C=C4)C(C)(C)O Chemical compound CC1=NN2C(=C1)N=C(C=C2OC(=O)N3CC[S+](CC3)O)NC(=O)C4=CC=C(C=C4)C(C)(C)O WKOYXLKFUWYNDP-UHFFFAOYSA-O 0.000 claims description 2
- 206010010356 Congenital anomaly Diseases 0.000 claims description 2
- YXGDDKWJKTYTQT-UHFFFAOYSA-N N-[7-(3-chloro-4-hydroxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(C=2C=C(Cl)C(O)=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 YXGDDKWJKTYTQT-UHFFFAOYSA-N 0.000 claims description 2
- XQZDZZNRKRWOSK-UHFFFAOYSA-N O=C(C1CC1)OC(C=C1)=CC=C1C(NC1=NC2=CC=NN2C(N2CCOCC2)=C1)=O Chemical compound O=C(C1CC1)OC(C=C1)=CC=C1C(NC1=NC2=CC=NN2C(N2CCOCC2)=C1)=O XQZDZZNRKRWOSK-UHFFFAOYSA-N 0.000 claims description 2
- 208000012931 Urologic disease Diseases 0.000 claims description 2
- 208000027744 congestion Diseases 0.000 claims description 2
- 208000016097 disease of metabolism Diseases 0.000 claims description 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
- SBBTUTORFZGOTQ-UHFFFAOYSA-N methyl 1-[4-[(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)carbamoyl]phenyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C(=O)NC2=NC3=CC(C)=NN3C(C=3C=CC=CC=3)=C2)C=CC=1C1(C(=O)OC)CC1 SBBTUTORFZGOTQ-UHFFFAOYSA-N 0.000 claims description 2
- SFZKDYLSCXPNKB-UHFFFAOYSA-N methyl 1-[5-[[4-(2-hydroxypropan-2-yl)benzoyl]amino]pyrazolo[1,5-a]pyrimidin-7-yl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OC)CCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 SFZKDYLSCXPNKB-UHFFFAOYSA-N 0.000 claims description 2
- RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 claims description 2
- WUYMFZXQINNMDH-UHFFFAOYSA-N methyl 3-methyl-3-[4-[(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)carbamoyl]phenyl]butanoate Chemical compound C1=CC(C(C)(C)CC(=O)OC)=CC=C1C(=O)NC1=NC2=CC(C)=NN2C(C=2C=CC=CC=2)=C1 WUYMFZXQINNMDH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 2
- OPUKJSNLBUTHEL-UHFFFAOYSA-N n-(2-cyclopropyl-7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC(C3CC3)=NN2C(N2CCOCC2)=C1 OPUKJSNLBUTHEL-UHFFFAOYSA-N 0.000 claims description 2
- BQGFLIBCWVBNJC-UHFFFAOYSA-N n-(2-cyclopropyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC(C3CC3)=NN2C(C=2C=CC=CC=2)=C1 BQGFLIBCWVBNJC-UHFFFAOYSA-N 0.000 claims description 2
- ZSTMVYUUNXHVKM-UHFFFAOYSA-N n-(2-ethyl-7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(N2CCOCC2)N2N=C(CC)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 ZSTMVYUUNXHVKM-UHFFFAOYSA-N 0.000 claims description 2
- MERDQKDFRBJRFH-UHFFFAOYSA-N n-(2-ethyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(C=2C=CC=CC=2)N2N=C(CC)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 MERDQKDFRBJRFH-UHFFFAOYSA-N 0.000 claims description 2
- HPGFYRQOXWFXPN-UHFFFAOYSA-N n-(2-hydroxyethyl)-1-[5-[[4-(2-hydroxypropan-2-yl)benzoyl]amino]-2-methylpyrazolo[1,5-a]pyrimidin-7-yl]piperidine-3-carboxamide Chemical compound C1=C(N2CC(CCC2)C(=O)NCCO)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 HPGFYRQOXWFXPN-UHFFFAOYSA-N 0.000 claims description 2
- OTWQDHKOMSWLBH-UHFFFAOYSA-N n-(2-methyl-7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(trifluoromethoxy)benzamide Chemical compound C1=C(N2CCOCC2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(OC(F)(F)F)C=C1 OTWQDHKOMSWLBH-UHFFFAOYSA-N 0.000 claims description 2
- ONAQJOVAGCFGNA-UHFFFAOYSA-N n-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)-2-pyridin-4-ylcyclopropane-1-carboxamide Chemical compound C1=C(C=2C=CC=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1CC1C1=CC=NC=C1 ONAQJOVAGCFGNA-UHFFFAOYSA-N 0.000 claims description 2
- FSOYJJCOCILNSQ-UHFFFAOYSA-N n-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(trifluoromethylsulfanyl)benzamide Chemical compound C1=C(C=2C=CC=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(SC(F)(F)F)C=C1 FSOYJJCOCILNSQ-UHFFFAOYSA-N 0.000 claims description 2
- XMCWVGPWWKKTGR-UHFFFAOYSA-N n-(7-butoxypyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide Chemical compound N=1C2=CC=NN2C(OCCCC)=CC=1NC(=O)C1=CC=C(C(C)(C)O)C=C1 XMCWVGPWWKKTGR-UHFFFAOYSA-N 0.000 claims description 2
- NMFBQUHBWLMBSC-UHFFFAOYSA-N n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)-1h-indole-2-carboxamide Chemical compound C=1C2=CC=CC=C2NC=1C(=O)NC(=NC1=CC=NN11)C=C1N1CCOCC1 NMFBQUHBWLMBSC-UHFFFAOYSA-N 0.000 claims description 2
- JLQYNJKCDXMTFU-UHFFFAOYSA-N n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)-1h-indole-6-carboxamide Chemical compound C=1C=C2C=CNC2=CC=1C(=O)NC(=NC1=CC=NN11)C=C1N1CCOCC1 JLQYNJKCDXMTFU-UHFFFAOYSA-N 0.000 claims description 2
- ICIIAJPTQIRTJR-UHFFFAOYSA-N n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)-4-phenylbenzamide Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)NC(=NC1=CC=NN11)C=C1N1CCOCC1 ICIIAJPTQIRTJR-UHFFFAOYSA-N 0.000 claims description 2
- GOAKYWJNGOHUDT-UHFFFAOYSA-N n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)cyclobutanecarboxamide Chemical compound C1CCC1C(=O)NC(=NC1=CC=NN11)C=C1N1CCOCC1 GOAKYWJNGOHUDT-UHFFFAOYSA-N 0.000 claims description 2
- YZKVXMKEPJBUOJ-UHFFFAOYSA-N n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)cyclopentanecarboxamide Chemical compound C1CCCC1C(=O)NC(=NC1=CC=NN11)C=C1N1CCOCC1 YZKVXMKEPJBUOJ-UHFFFAOYSA-N 0.000 claims description 2
- BCUZRCFZMBJTLS-UHFFFAOYSA-N n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)cyclopropanecarboxamide Chemical compound C1CC1C(=O)NC(=NC1=CC=NN11)C=C1N1CCOCC1 BCUZRCFZMBJTLS-UHFFFAOYSA-N 0.000 claims description 2
- HDWTWKHIJLRRQS-UHFFFAOYSA-N n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)isoquinoline-1-carboxamide Chemical compound N=1C=CC2=CC=CC=C2C=1C(=O)NC(=NC1=CC=NN11)C=C1N1CCOCC1 HDWTWKHIJLRRQS-UHFFFAOYSA-N 0.000 claims description 2
- JRIKQZXEEDAPST-UHFFFAOYSA-N n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)naphthalene-1-carboxamide Chemical compound C=1C=CC2=CC=CC=C2C=1C(=O)NC(=NC1=CC=NN11)C=C1N1CCOCC1 JRIKQZXEEDAPST-UHFFFAOYSA-N 0.000 claims description 2
- HCSUTONYMOXNKH-UHFFFAOYSA-N n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)naphthalene-2-carboxamide Chemical compound C=1C=C2C=CC=CC2=CC=1C(=O)NC(=NC1=CC=NN11)C=C1N1CCOCC1 HCSUTONYMOXNKH-UHFFFAOYSA-N 0.000 claims description 2
- FTIAAQOYCNRCHK-UHFFFAOYSA-N n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)pyrazine-2-carboxamide Chemical compound C=1N=CC=NC=1C(=O)NC(=NC1=CC=NN11)C=C1N1CCOCC1 FTIAAQOYCNRCHK-UHFFFAOYSA-N 0.000 claims description 2
- PTVYPHBQXFDCGC-UHFFFAOYSA-N n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)pyridine-2-carboxamide Chemical compound C=1C=CC=NC=1C(=O)NC(=NC1=CC=NN11)C=C1N1CCOCC1 PTVYPHBQXFDCGC-UHFFFAOYSA-N 0.000 claims description 2
- DIKAUSMLHNEYTM-UHFFFAOYSA-N n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)pyridine-3-carboxamide Chemical compound C=1C=CN=CC=1C(=O)NC(=NC1=CC=NN11)C=C1N1CCOCC1 DIKAUSMLHNEYTM-UHFFFAOYSA-N 0.000 claims description 2
- STQVQHAXYKGWKV-UHFFFAOYSA-N n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)quinoline-2-carboxamide Chemical compound C=1C=C2C=CC=CC2=NC=1C(=O)NC(=NC1=CC=NN11)C=C1N1CCOCC1 STQVQHAXYKGWKV-UHFFFAOYSA-N 0.000 claims description 2
- FKNKCEVMDPZHLL-UHFFFAOYSA-N n-[2-cyclopropyl-7-(4-hydroxypiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC(C3CC3)=NN2C(N2CCC(O)CC2)=C1 FKNKCEVMDPZHLL-UHFFFAOYSA-N 0.000 claims description 2
- ADDYBUKCSAYFCN-UHFFFAOYSA-N n-[2-cyclopropyl-7-[3-(hydroxymethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC(C3CC3)=NN2C(C=2C=C(CO)C=CC=2)=C1 ADDYBUKCSAYFCN-UHFFFAOYSA-N 0.000 claims description 2
- SQHKKZOFRSMHKZ-UHFFFAOYSA-N n-[2-ethyl-7-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(C=2C=CC(OC)=CC=2)N2N=C(CC)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 SQHKKZOFRSMHKZ-UHFFFAOYSA-N 0.000 claims description 2
- FHAQFTIPYLRUNH-UHFFFAOYSA-N n-[2-methyl-7-(4-oxo-1,5,7,8-tetrahydropyrido[4,3-d]pyrimidin-6-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-6-(trifluoromethyl)pyridine-3-carboxamide Chemical compound C1=C(N2CC=3C(=O)NC=NC=3CC2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(F)(F)F)N=C1 FHAQFTIPYLRUNH-UHFFFAOYSA-N 0.000 claims description 2
- JZIJXAUJSGKFCX-UHFFFAOYSA-N n-[7-(1-benzofuran-5-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(C=2C=C3C=COC3=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 JZIJXAUJSGKFCX-UHFFFAOYSA-N 0.000 claims description 2
- OJHFPZOZLUFFNK-UHFFFAOYSA-N n-[7-(1-benzothiophen-2-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-tert-butylbenzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2SC3=CC=CC=C3C=2)=C1 OJHFPZOZLUFFNK-UHFFFAOYSA-N 0.000 claims description 2
- XDPZNOYZTVTBJI-UHFFFAOYSA-N n-[7-(1-benzothiophen-5-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(C=2C=C3C=CSC3=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 XDPZNOYZTVTBJI-UHFFFAOYSA-N 0.000 claims description 2
- RCCIIPOVABHVEQ-UHFFFAOYSA-N n-[7-(1-benzylpyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-tert-butylbenzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C2=CN(CC=3C=CC=CC=3)N=C2)=C1 RCCIIPOVABHVEQ-UHFFFAOYSA-N 0.000 claims description 2
- SRZVUWXFVSDPOH-UHFFFAOYSA-N n-[7-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(C=2C=C3OCCOC3=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 SRZVUWXFVSDPOH-UHFFFAOYSA-N 0.000 claims description 2
- LSQIXHYREQQVBX-UHFFFAOYSA-N n-[7-(2,3-dihydro-1-benzofuran-5-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=C3CCOC3=CC=2)=C1 LSQIXHYREQQVBX-UHFFFAOYSA-N 0.000 claims description 2
- FRIMYNAZEZEIHL-UHFFFAOYSA-N n-[7-(2,5-dimethylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound CC1CNC(C)CN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 FRIMYNAZEZEIHL-UHFFFAOYSA-N 0.000 claims description 2
- CVHOBRVTMBYFCA-UHFFFAOYSA-N n-[7-(2,6-dimethylmorpholin-4-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1C(C)OC(C)CN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 CVHOBRVTMBYFCA-UHFFFAOYSA-N 0.000 claims description 2
- PWGUALKWLXGXAH-UHFFFAOYSA-N n-[7-(2-acetamidoethylamino)pyrazolo[1,5-a]pyrimidin-5-yl]-4-tert-butylbenzamide Chemical compound N=1C2=CC=NN2C(NCCNC(=O)C)=CC=1NC(=O)C1=CC=C(C(C)(C)C)C=C1 PWGUALKWLXGXAH-UHFFFAOYSA-N 0.000 claims description 2
- XTEYFWCUKBBSBT-UHFFFAOYSA-N n-[7-(2-acetamidophenyl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-tert-butylbenzamide Chemical compound CC(=O)NC1=CC=CC=C1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)C)=NC2=CC=NN12 XTEYFWCUKBBSBT-UHFFFAOYSA-N 0.000 claims description 2
- BVTWWNVIJQQJRS-UHFFFAOYSA-N n-[7-(3,3-dimethylpiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CC(C)(C)CCC2)=C1 BVTWWNVIJQQJRS-UHFFFAOYSA-N 0.000 claims description 2
- VEWKFBYPAYSZTD-UHFFFAOYSA-N n-[7-(3,4-dihydro-2h-1,5-benzodioxepin-7-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(C=2C=C3OCCCOC3=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 VEWKFBYPAYSZTD-UHFFFAOYSA-N 0.000 claims description 2
- KIXKARMPHFURHJ-UHFFFAOYSA-N n-[7-(3,4-dimethoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC(C)=NN12 KIXKARMPHFURHJ-UHFFFAOYSA-N 0.000 claims description 2
- IRTOZPPWXFRTRM-UHFFFAOYSA-N n-[7-(3-acetamidophenyl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound CC(=O)NC1=CC=CC(C=2N3N=CC=C3N=C(NC(=O)C=3C=CC(=CC=3)C(C)(C)O)C=2)=C1 IRTOZPPWXFRTRM-UHFFFAOYSA-N 0.000 claims description 2
- GAOPZXNWJBZZGO-UHFFFAOYSA-N n-[7-(3-acetamidopyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-tert-butylbenzamide Chemical compound C1C(NC(=O)C)CCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)C)=NC2=CC=NN12 GAOPZXNWJBZZGO-UHFFFAOYSA-N 0.000 claims description 2
- VJGSUTXXRJAXIU-UHFFFAOYSA-N n-[7-(3-acetylphenyl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-tert-butylbenzamide Chemical compound CC(=O)C1=CC=CC(C=2N3N=CC=C3N=C(NC(=O)C=3C=CC(=CC=3)C(C)(C)C)C=2)=C1 VJGSUTXXRJAXIU-UHFFFAOYSA-N 0.000 claims description 2
- QKMOFNDOZPPJQC-UHFFFAOYSA-N n-[7-(3-chloro-4-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(Cl)C(OC)=CC=C1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC(C)=NN12 QKMOFNDOZPPJQC-UHFFFAOYSA-N 0.000 claims description 2
- MKODGKWQJKCQRG-UHFFFAOYSA-N n-[7-(3-fluoro-4-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(F)C(OC)=CC=C1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC(C)=NN12 MKODGKWQJKCQRG-UHFFFAOYSA-N 0.000 claims description 2
- ZYUKLUSFJNUMBB-UHFFFAOYSA-N n-[7-(3-fluoropyrrolidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(N2CC(F)CC2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 ZYUKLUSFJNUMBB-UHFFFAOYSA-N 0.000 claims description 2
- CMJMDOYEPQELBK-UHFFFAOYSA-N n-[7-(3-fluoropyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CC(F)CC2)=C1 CMJMDOYEPQELBK-UHFFFAOYSA-N 0.000 claims description 2
- XCPSKVKLNWTWNK-UHFFFAOYSA-N n-[7-(3-hydroxyazetidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CC(O)C2)=C1 XCPSKVKLNWTWNK-UHFFFAOYSA-N 0.000 claims description 2
- FPVRMLKKCXYSRT-UHFFFAOYSA-N n-[7-(4,4-difluoropiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CCC(F)(F)CC2)=C1 FPVRMLKKCXYSRT-UHFFFAOYSA-N 0.000 claims description 2
- PLUCVGXBZYKWJO-UHFFFAOYSA-N n-[7-(4-acetamidopiperidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-2-(4-fluorophenyl)cyclopropane-1-carboxamide Chemical compound C1CC(NC(=O)C)CCN1C1=CC(NC(=O)C2C(C2)C=2C=CC(F)=CC=2)=NC2=CC(C)=NN12 PLUCVGXBZYKWJO-UHFFFAOYSA-N 0.000 claims description 2
- BAQLCCJCNPZGRP-UHFFFAOYSA-N n-[7-(4-acetamidopiperidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-2-phenylcyclopropane-1-carboxamide Chemical compound C1CC(NC(=O)C)CCN1C1=CC(NC(=O)C2C(C2)C=2C=CC=CC=2)=NC2=CC(C)=NN12 BAQLCCJCNPZGRP-UHFFFAOYSA-N 0.000 claims description 2
- PMHYKFSXBCPOQU-UHFFFAOYSA-N n-[7-(4-acetamidopiperidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1CC(NC(=O)C)CCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC(C)=NN12 PMHYKFSXBCPOQU-UHFFFAOYSA-N 0.000 claims description 2
- DUCDCBMKWBHRQP-UHFFFAOYSA-N n-[7-(4-acetamidopiperidin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(trifluoromethoxy)benzamide Chemical compound C1CC(NC(=O)C)CCN1C1=CC(NC(=O)C=2C=CC(OC(F)(F)F)=CC=2)=NC2=CC(C)=NN12 DUCDCBMKWBHRQP-UHFFFAOYSA-N 0.000 claims description 2
- QVQWLKHJJGVYLZ-UHFFFAOYSA-N n-[7-(4-acetyl-1,4-diazepan-1-yl)-2-ethylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(N2CCN(CCC2)C(C)=O)N2N=C(CC)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 QVQWLKHJJGVYLZ-UHFFFAOYSA-N 0.000 claims description 2
- MDOVNNQNKBRACZ-UHFFFAOYSA-N n-[7-(4-acetyl-1,4-diazepan-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1CN(C(=O)C)CCCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC(C)=NN12 MDOVNNQNKBRACZ-UHFFFAOYSA-N 0.000 claims description 2
- GZTMBUOBNRVKPK-UHFFFAOYSA-N n-[7-(4-acetyl-1,4-diazepan-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1CN(C(=O)C)CCCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 GZTMBUOBNRVKPK-UHFFFAOYSA-N 0.000 claims description 2
- CKYUAZMFSWKXPC-UHFFFAOYSA-N n-[7-(4-chloro-3-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(Cl)C(OC)=CC(C=2N3N=C(C)C=C3N=C(NC(=O)C=3C=CC(=CC=3)C(C)(C)O)C=2)=C1 CKYUAZMFSWKXPC-UHFFFAOYSA-N 0.000 claims description 2
- RQYQCZBTJIJGFO-UHFFFAOYSA-N n-[7-(4-chloro-3-methylphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(C=2C=C(C)C(Cl)=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 RQYQCZBTJIJGFO-UHFFFAOYSA-N 0.000 claims description 2
- UFAZMLALHXATRN-UHFFFAOYSA-N n-[7-(4-chlorophenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(C=2C=CC(Cl)=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 UFAZMLALHXATRN-UHFFFAOYSA-N 0.000 claims description 2
- WFFYREPHDYEYIB-UHFFFAOYSA-N n-[7-(4-chlorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=CC(Cl)=CC=2)=C1 WFFYREPHDYEYIB-UHFFFAOYSA-N 0.000 claims description 2
- RAVDORCIIGKVID-UHFFFAOYSA-N n-[7-(4-ethylsulfonylpiperazin-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1CN(S(=O)(=O)CC)CCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC(C)=NN12 RAVDORCIIGKVID-UHFFFAOYSA-N 0.000 claims description 2
- NBTPAULWHKTYSI-UHFFFAOYSA-N n-[7-(4-fluoro-3-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(F)C(OC)=CC(C=2N3N=C(C)C=C3N=C(NC(=O)C=3C=CC(=CC=3)C(C)(C)O)C=2)=C1 NBTPAULWHKTYSI-UHFFFAOYSA-N 0.000 claims description 2
- WVPRZQFVXLXOQW-UHFFFAOYSA-N n-[7-(4-fluorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=CC(F)=CC=2)=C1 WVPRZQFVXLXOQW-UHFFFAOYSA-N 0.000 claims description 2
- YJFSMWYZHUWZQW-UHFFFAOYSA-N n-[7-(4-formyl-1,4-diazepan-1-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(N2CCN(CCC2)C=O)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 YJFSMWYZHUWZQW-UHFFFAOYSA-N 0.000 claims description 2
- ULSTWQKCFHLIIY-UHFFFAOYSA-N n-[7-(4-formyl-1,4-diazepan-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CCN(CCC2)C=O)=C1 ULSTWQKCFHLIIY-UHFFFAOYSA-N 0.000 claims description 2
- SKDLLRSDYAKYKX-UHFFFAOYSA-N n-[7-(4-formylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CCN(CC2)C=O)=C1 SKDLLRSDYAKYKX-UHFFFAOYSA-N 0.000 claims description 2
- ZRFVWIOXHVWPAH-UHFFFAOYSA-N n-[7-(4-methoxyphenyl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-2-phenylcyclopropane-1-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=CC(NC(=O)C2C(C2)C=2C=CC=CC=2)=NC2=CC(C)=NN12 ZRFVWIOXHVWPAH-UHFFFAOYSA-N 0.000 claims description 2
- MOBPYRXGYZFLLV-UHFFFAOYSA-N n-[7-(5-chlorothiophen-2-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(C=2SC(Cl)=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 MOBPYRXGYZFLLV-UHFFFAOYSA-N 0.000 claims description 2
- AFSYGHSRVUTXCS-UHFFFAOYSA-N n-[7-(6-acetamidopyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-tert-butylbenzamide Chemical compound C1=NC(NC(=O)C)=CC=C1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)C)=NC2=CC=NN12 AFSYGHSRVUTXCS-UHFFFAOYSA-N 0.000 claims description 2
- YMVPSNWNOCCXRQ-UHFFFAOYSA-N n-[7-(6-ethoxypyridin-3-yl)-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=NC(OCC)=CC=C1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC(C)=NN12 YMVPSNWNOCCXRQ-UHFFFAOYSA-N 0.000 claims description 2
- ITWUICXUCZCLFG-UHFFFAOYSA-N n-[7-(benzylamino)pyrazolo[1,5-a]pyrimidin-5-yl]-4-tert-butylbenzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(NCC=2C=CC=CC=2)=C1 ITWUICXUCZCLFG-UHFFFAOYSA-N 0.000 claims description 2
- YZQMRCNHOWOGFM-UHFFFAOYSA-N n-[7-(cyclopropylamino)pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(NC2CC2)=C1 YZQMRCNHOWOGFM-UHFFFAOYSA-N 0.000 claims description 2
- ZWBRUWNOURXXFY-UHFFFAOYSA-N n-[7-(furan-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C2=COC=C2)=C1 ZWBRUWNOURXXFY-UHFFFAOYSA-N 0.000 claims description 2
- NLOZGPVCMXOSBO-UHFFFAOYSA-N n-[7-[(2-amino-2-oxoethyl)amino]pyrazolo[1,5-a]pyrimidin-5-yl]-4-tert-butylbenzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(NCC(N)=O)=C1 NLOZGPVCMXOSBO-UHFFFAOYSA-N 0.000 claims description 2
- QAWAGEIDSIRFEG-UHFFFAOYSA-N n-[7-[(3-amino-3-oxopropyl)amino]pyrazolo[1,5-a]pyrimidin-5-yl]-4-tert-butylbenzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(NCCC(N)=O)=C1 QAWAGEIDSIRFEG-UHFFFAOYSA-N 0.000 claims description 2
- YUIHSJPQWUJXRG-QGZVFWFLSA-N n-[7-[(3r)-3-(dimethylamino)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1[C@H](N(C)C)CCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 YUIHSJPQWUJXRG-QGZVFWFLSA-N 0.000 claims description 2
- RIXBOFJAWNSJJD-GOSISDBHSA-N n-[7-[(3r)-3-acetamidopiperidin-1-yl]pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1[C@H](NC(=O)C)CCCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 RIXBOFJAWNSJJD-GOSISDBHSA-N 0.000 claims description 2
- YUJPRSWKBRFJBI-QGZVFWFLSA-N n-[7-[(3r)-3-acetamidopyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1[C@H](NC(=O)C)CCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 YUJPRSWKBRFJBI-QGZVFWFLSA-N 0.000 claims description 2
- GAOPZXNWJBZZGO-GOSISDBHSA-N n-[7-[(3r)-3-acetamidopyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-5-yl]-4-tert-butylbenzamide Chemical compound C1[C@H](NC(=O)C)CCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)C)=NC2=CC=NN12 GAOPZXNWJBZZGO-GOSISDBHSA-N 0.000 claims description 2
- UAZQWXUPPLTVMK-KLAILNCOSA-N n-[7-[(3r)-3-fluoropyrrolidin-1-yl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-2-phenylcyclopropane-1-carboxamide Chemical compound C1=C(N2C[C@H](F)CC2)N2N=C(C)C=C2N=C1NC(=O)C1CC1C1=CC=CC=C1 UAZQWXUPPLTVMK-KLAILNCOSA-N 0.000 claims description 2
- RIXBOFJAWNSJJD-SFHVURJKSA-N n-[7-[(3s)-3-acetamidopiperidin-1-yl]pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1[C@@H](NC(=O)C)CCCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 RIXBOFJAWNSJJD-SFHVURJKSA-N 0.000 claims description 2
- YUJPRSWKBRFJBI-KRWDZBQOSA-N n-[7-[(3s)-3-acetamidopyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1[C@@H](NC(=O)C)CCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 YUJPRSWKBRFJBI-KRWDZBQOSA-N 0.000 claims description 2
- GWMBGNCOGKPDQP-INIZCTEOSA-N n-[7-[(3s)-3-aminopiperidin-1-yl]pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2C[C@@H](N)CCC2)=C1 GWMBGNCOGKPDQP-INIZCTEOSA-N 0.000 claims description 2
- UAZQWXUPPLTVMK-GTPINHCMSA-N n-[7-[(3s)-3-fluoropyrrolidin-1-yl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-2-phenylcyclopropane-1-carboxamide Chemical compound C1=C(N2C[C@@H](F)CC2)N2N=C(C)C=C2N=C1NC(=O)C1CC1C1=CC=CC=C1 UAZQWXUPPLTVMK-GTPINHCMSA-N 0.000 claims description 2
- OMDWXUAZPMBIMZ-UHFFFAOYSA-N n-[7-[2-(2-hydroxyethyl)piperidin-1-yl]pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2C(CCCC2)CCO)=C1 OMDWXUAZPMBIMZ-UHFFFAOYSA-N 0.000 claims description 2
- HGFMTDOZRMZAKE-UHFFFAOYSA-N n-[7-[2-(acetylsulfamoyl)ethyl-methylamino]pyrazolo[1,5-a]pyrimidin-5-yl]-4-tert-butylbenzamide Chemical compound N=1C2=CC=NN2C(N(CCS(=O)(=O)NC(C)=O)C)=CC=1NC(=O)C1=CC=C(C(C)(C)C)C=C1 HGFMTDOZRMZAKE-UHFFFAOYSA-N 0.000 claims description 2
- ALXZPDICGNLWMN-UHFFFAOYSA-N n-[7-[3-(cyanomethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=C(CC#N)C=CC=2)=C1 ALXZPDICGNLWMN-UHFFFAOYSA-N 0.000 claims description 2
- WIUBDPVCYFVRGZ-UHFFFAOYSA-N n-[7-[3-(dimethylamino)phenyl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound CN(C)C1=CC=CC(C=2N3N=C(C)C=C3N=C(NC(=O)C=3C=CC(=CC=3)C(C)(C)O)C=2)=C1 WIUBDPVCYFVRGZ-UHFFFAOYSA-N 0.000 claims description 2
- FZVYUICXNYCBFC-UHFFFAOYSA-N n-[7-[3-(hydroxymethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]-4-(1,1,1-trifluoro-2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(O)(C)C(F)(F)F)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=C(CO)C=CC=2)=C1 FZVYUICXNYCBFC-UHFFFAOYSA-N 0.000 claims description 2
- RHRRIETVEGSRDU-UHFFFAOYSA-N n-[7-[3-(hydroxymethyl)piperidin-1-yl]pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CC(CO)CCC2)=C1 RHRRIETVEGSRDU-UHFFFAOYSA-N 0.000 claims description 2
- CTTKOLYAYSHOIV-UHFFFAOYSA-N n-[7-[4-(2-amino-2-oxoethyl)piperidin-1-yl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(trifluoromethoxy)benzamide Chemical compound C1=C(N2CCC(CC(N)=O)CC2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(OC(F)(F)F)C=C1 CTTKOLYAYSHOIV-UHFFFAOYSA-N 0.000 claims description 2
- PLWPTZIISYVPKO-UHFFFAOYSA-N n-[7-[4-(2-hydroxyethyl)piperidin-1-yl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-2-phenylcyclopropane-1-carboxamide Chemical compound C1=C(N2CCC(CCO)CC2)N2N=C(C)C=C2N=C1NC(=O)C1CC1C1=CC=CC=C1 PLWPTZIISYVPKO-UHFFFAOYSA-N 0.000 claims description 2
- LRKCSESWUGRGGP-UHFFFAOYSA-N n-[7-[4-(2-hydroxyethyl)piperidin-1-yl]pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CCC(CCO)CC2)=C1 LRKCSESWUGRGGP-UHFFFAOYSA-N 0.000 claims description 2
- UHVPBXFTSUYPJN-UHFFFAOYSA-N n-[7-[4-(benzenesulfonyl)piperidin-1-yl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(N2CCC(CC2)S(=O)(=O)C=2C=CC=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 UHVPBXFTSUYPJN-UHFFFAOYSA-N 0.000 claims description 2
- PMRUKZBTOJVGPW-UHFFFAOYSA-N n-[7-[4-(carbamoylamino)piperidin-1-yl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-2-(4-fluorophenyl)cyclopropane-1-carboxamide Chemical compound C1=C(N2CCC(CC2)NC(N)=O)N2N=C(C)C=C2N=C1NC(=O)C1CC1C1=CC=C(F)C=C1 PMRUKZBTOJVGPW-UHFFFAOYSA-N 0.000 claims description 2
- FSXOIVPEFWVRPF-UHFFFAOYSA-N n-[7-[4-(carbamoylamino)piperidin-1-yl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-2-pyridin-4-ylcyclopropane-1-carboxamide Chemical compound C1=C(N2CCC(CC2)NC(N)=O)N2N=C(C)C=C2N=C1NC(=O)C1CC1C1=CC=NC=C1 FSXOIVPEFWVRPF-UHFFFAOYSA-N 0.000 claims description 2
- JETIGXKPROJZQI-UHFFFAOYSA-N n-[7-[4-(carbamoylamino)piperidin-1-yl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(N2CCC(CC2)NC(N)=O)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 JETIGXKPROJZQI-UHFFFAOYSA-N 0.000 claims description 2
- ZJKBBUNBZBYKJM-UHFFFAOYSA-N n-[7-[4-(carbamoylamino)piperidin-1-yl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(trifluoromethoxy)benzamide Chemical compound C1=C(N2CCC(CC2)NC(N)=O)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(OC(F)(F)F)C=C1 ZJKBBUNBZBYKJM-UHFFFAOYSA-N 0.000 claims description 2
- BQYRDXRGLYWNES-UHFFFAOYSA-N n-[7-[4-(cyclopropanecarbonylamino)piperidin-1-yl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(N2CCC(CC2)NC(=O)C2CC2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 BQYRDXRGLYWNES-UHFFFAOYSA-N 0.000 claims description 2
- UMBAFAFAXCPVTN-UHFFFAOYSA-N n-[7-[4-(hydroxymethyl)piperidin-1-yl]pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CCC(CO)CC2)=C1 UMBAFAFAXCPVTN-UHFFFAOYSA-N 0.000 claims description 2
- PGZMGHBFXJWQCE-UHFFFAOYSA-N n-[7-[4-[2-(dimethylamino)ethoxy]phenyl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(OCCN(C)C)=CC=C1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC(C)=NN12 PGZMGHBFXJWQCE-UHFFFAOYSA-N 0.000 claims description 2
- NVMWBSARIDPFQN-UHFFFAOYSA-N n-[7-[6-(cyclopropylmethoxy)pyridin-3-yl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(C=2C=NC(OCC3CC3)=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 NVMWBSARIDPFQN-UHFFFAOYSA-N 0.000 claims description 2
- XXCQKPIYNIDZEQ-UHFFFAOYSA-N n-[7-[[3,5-bis(trifluoromethyl)phenyl]methylamino]pyrazolo[1,5-a]pyrimidin-5-yl]-4-tert-butylbenzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(NCC=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=C1 XXCQKPIYNIDZEQ-UHFFFAOYSA-N 0.000 claims description 2
- OKCQNCWRJGDHEL-UHFFFAOYSA-N n-[7-[benzyl-[2-(dimethylamino)ethyl]amino]pyrazolo[1,5-a]pyrimidin-5-yl]-4-tert-butylbenzamide Chemical compound C=1C(NC(=O)C=2C=CC(=CC=2)C(C)(C)C)=NC2=CC=NN2C=1N(CCN(C)C)CC1=CC=CC=C1 OKCQNCWRJGDHEL-UHFFFAOYSA-N 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- BVOCPVIXARZNQN-UHFFFAOYSA-N nipecotamide Chemical compound NC(=O)C1CCCNC1 BVOCPVIXARZNQN-UHFFFAOYSA-N 0.000 claims description 2
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 2
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 2
- GRYZPQLNDOYTDC-QGZVFWFLSA-N (3r)-1-[5-[[4-(2-hydroxypropan-2-yl)benzoyl]amino]pyrazolo[1,5-a]pyrimidin-7-yl]-n,n-dimethylpiperidine-3-carboxamide Chemical compound C1[C@H](C(=O)N(C)C)CCCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 GRYZPQLNDOYTDC-QGZVFWFLSA-N 0.000 claims 1
- URFCAOPDTOXVIT-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CCOCC2)=C1 URFCAOPDTOXVIT-UHFFFAOYSA-N 0.000 claims 1
- IVBSAIKVCDGIBT-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[2-methyl-7-(4-methylpiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1CC(C)CCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC(C)=NN12 IVBSAIKVCDGIBT-UHFFFAOYSA-N 0.000 claims 1
- PIOIFEKRDIJJDS-UHFFFAOYSA-N 4-tert-butyl-n-[7-[2-(1h-imidazol-5-yl)ethylamino]pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(NCCC=2NC=NC=2)=C1 PIOIFEKRDIJJDS-UHFFFAOYSA-N 0.000 claims 1
- RBYRTOVYVOCQJT-UHFFFAOYSA-N 4-tert-butyl-n-[7-[3-(cyanomethyl)phenyl]pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C=2C=C(CC#N)C=CC=2)=C1 RBYRTOVYVOCQJT-UHFFFAOYSA-N 0.000 claims 1
- 206010010904 Convulsion Diseases 0.000 claims 1
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims 1
- 230000001771 impaired effect Effects 0.000 claims 1
- MFHCJCXVSNXMMX-UHFFFAOYSA-N methyl 4-[[7-chloro-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-yl]carbamoyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C(=O)NC1=NC2=CC(C(F)(F)F)=NN2C(Cl)=C1 MFHCJCXVSNXMMX-UHFFFAOYSA-N 0.000 claims 1
- BDPSQJSOSJRMOB-UHFFFAOYSA-N n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)-1h-imidazole-5-carboxamide Chemical compound C=1NC=NC=1C(=O)NC(=NC1=CC=NN11)C=C1N1CCOCC1 BDPSQJSOSJRMOB-UHFFFAOYSA-N 0.000 claims 1
- 125000006308 propyl amino group Chemical group 0.000 claims 1
- 108010075639 MAP Kinase Kinase Kinase 5 Proteins 0.000 description 79
- 239000000203 mixture Substances 0.000 description 70
- 239000003112 inhibitor Substances 0.000 description 60
- 150000003254 radicals Chemical class 0.000 description 58
- 238000000034 method Methods 0.000 description 54
- 235000002639 sodium chloride Nutrition 0.000 description 45
- 125000002993 cycloalkylene group Chemical group 0.000 description 30
- 210000004027 cell Anatomy 0.000 description 25
- 229910052799 carbon Inorganic materials 0.000 description 21
- 125000003342 alkenyl group Chemical group 0.000 description 20
- 125000004429 atom Chemical group 0.000 description 20
- 125000004432 carbon atom Chemical group C* 0.000 description 20
- 230000000694 effects Effects 0.000 description 20
- 239000000556 agonist Substances 0.000 description 19
- 239000002552 dosage form Substances 0.000 description 19
- 238000001727 in vivo Methods 0.000 description 18
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 18
- 125000002619 bicyclic group Chemical group 0.000 description 17
- 125000004122 cyclic group Chemical group 0.000 description 16
- 230000037361 pathway Effects 0.000 description 16
- 238000011282 treatment Methods 0.000 description 16
- 239000002253 acid Substances 0.000 description 15
- 125000002947 alkylene group Chemical group 0.000 description 15
- 125000001118 alkylidene group Chemical group 0.000 description 15
- 239000003472 antidiabetic agent Substances 0.000 description 15
- 229940002612 prodrug Drugs 0.000 description 15
- 239000000651 prodrug Substances 0.000 description 15
- 229920006395 saturated elastomer Polymers 0.000 description 15
- 102000043136 MAP kinase family Human genes 0.000 description 14
- 108091054455 MAP kinase family Proteins 0.000 description 14
- 230000003178 anti-diabetic effect Effects 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 125000003367 polycyclic group Chemical group 0.000 description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- 125000004450 alkenylene group Chemical group 0.000 description 12
- 125000004419 alkynylene group Chemical group 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 125000006413 ring segment Chemical group 0.000 description 12
- 239000003826 tablet Substances 0.000 description 12
- 108010055717 JNK Mitogen-Activated Protein Kinases Proteins 0.000 description 11
- 230000035882 stress Effects 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 10
- 239000002775 capsule Substances 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- 239000012453 solvate Substances 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 102000004877 Insulin Human genes 0.000 description 9
- 108090001061 Insulin Proteins 0.000 description 9
- 229940125396 insulin Drugs 0.000 description 9
- 239000000543 intermediate Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 229910052717 sulfur Chemical group 0.000 description 9
- 208000024891 symptom Diseases 0.000 description 9
- 102100040918 Pro-glucagon Human genes 0.000 description 8
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 8
- 125000002723 alicyclic group Chemical group 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 239000000796 flavoring agent Substances 0.000 description 8
- 125000002950 monocyclic group Chemical group 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 125000006239 protecting group Chemical group 0.000 description 8
- 229940124597 therapeutic agent Drugs 0.000 description 8
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 7
- 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 7
- 229930006000 Sucrose Natural products 0.000 description 7
- 239000013543 active substance Substances 0.000 description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
- 239000000839 emulsion Substances 0.000 description 7
- 239000008187 granular material Substances 0.000 description 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 7
- 239000001301 oxygen Chemical group 0.000 description 7
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 description 7
- 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 description 7
- 235000018102 proteins Nutrition 0.000 description 7
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 7
- 239000005720 sucrose Substances 0.000 description 7
- 229960004793 sucrose Drugs 0.000 description 7
- 125000004149 thio group Chemical group *S* 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 102100029820 Mitochondrial brown fat uncoupling protein 1 Human genes 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 150000004677 hydrates Chemical class 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 6
- 150000007524 organic acids Chemical class 0.000 description 6
- 239000005022 packaging material Substances 0.000 description 6
- 235000021317 phosphate Nutrition 0.000 description 6
- HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000011593 sulfur Chemical group 0.000 description 6
- 239000006188 syrup Substances 0.000 description 6
- 235000020357 syrup Nutrition 0.000 description 6
- 230000001225 therapeutic effect Effects 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- 102000003390 tumor necrosis factor Human genes 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 description 5
- FAEKWTJYAYMJKF-QHCPKHFHSA-N GlucoNorm Chemical group C1=C(C(O)=O)C(OCC)=CC(CC(=O)N[C@@H](CC(C)C)C=2C(=CC=CC=2)N2CCCCC2)=C1 FAEKWTJYAYMJKF-QHCPKHFHSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
- 108090000744 Mitogen-Activated Protein Kinase Kinases Proteins 0.000 description 5
- 102000004232 Mitogen-Activated Protein Kinase Kinases Human genes 0.000 description 5
- 102000034527 Retinoid X Receptors Human genes 0.000 description 5
- 108010038912 Retinoid X Receptors Proteins 0.000 description 5
- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 5
- 229920002472 Starch Polymers 0.000 description 5
- 229960002632 acarbose Drugs 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 150000001721 carbon Chemical group 0.000 description 5
- 239000003937 drug carrier Substances 0.000 description 5
- 239000003623 enhancer Substances 0.000 description 5
- 235000013355 food flavoring agent Nutrition 0.000 description 5
- 235000003599 food sweetener Nutrition 0.000 description 5
- 229960004580 glibenclamide Drugs 0.000 description 5
- 229960001031 glucose Drugs 0.000 description 5
- ZNNLBTZKUZBEKO-UHFFFAOYSA-N glyburide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZNNLBTZKUZBEKO-UHFFFAOYSA-N 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- OELFLUMRDSZNSF-BRWVUGGUSA-N nateglinide Chemical compound C1C[C@@H](C(C)C)CC[C@@H]1C(=O)N[C@@H](C(O)=O)CC1=CC=CC=C1 OELFLUMRDSZNSF-BRWVUGGUSA-N 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
- 230000026731 phosphorylation Effects 0.000 description 5
- 238000006366 phosphorylation reaction Methods 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 230000001105 regulatory effect Effects 0.000 description 5
- 239000008107 starch Substances 0.000 description 5
- 229940032147 starch Drugs 0.000 description 5
- 235000019698 starch Nutrition 0.000 description 5
- 239000003765 sweetening agent Substances 0.000 description 5
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- NKOHRVBBQISBSB-UHFFFAOYSA-N 5-[(4-hydroxyphenyl)methyl]-1,3-thiazolidine-2,4-dione Chemical compound C1=CC(O)=CC=C1CC1C(=O)NC(=O)S1 NKOHRVBBQISBSB-UHFFFAOYSA-N 0.000 description 4
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 4
- 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 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- 101150065749 Churc1 gene Proteins 0.000 description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 108010007457 Extracellular Signal-Regulated MAP Kinases Proteins 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- 229940122904 Glucagon receptor antagonist Drugs 0.000 description 4
- 101800000224 Glucagon-like peptide 1 Proteins 0.000 description 4
- 101800000221 Glucagon-like peptide 2 Proteins 0.000 description 4
- 102000003638 Glucose-6-Phosphatase Human genes 0.000 description 4
- 108010086800 Glucose-6-Phosphatase Proteins 0.000 description 4
- 102000007390 Glycogen Phosphorylase Human genes 0.000 description 4
- 108010046163 Glycogen Phosphorylase Proteins 0.000 description 4
- 102000002254 Glycogen Synthase Kinase 3 Human genes 0.000 description 4
- 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 description 4
- 241000282412 Homo Species 0.000 description 4
- 206010022489 Insulin Resistance Diseases 0.000 description 4
- 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 4
- 102100024193 Mitogen-activated protein kinase 1 Human genes 0.000 description 4
- 150000001204 N-oxides Chemical class 0.000 description 4
- 108010016731 PPAR gamma Proteins 0.000 description 4
- 102100038825 Peroxisome proliferator-activated receptor gamma Human genes 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 102100038239 Protein Churchill Human genes 0.000 description 4
- 102000002727 Protein Tyrosine Phosphatase Human genes 0.000 description 4
- 102000053067 Pyruvate Dehydrogenase Acetyl-Transferring Kinase Human genes 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 101710159466 [Pyruvate dehydrogenase (acetyl-transferring)] kinase, mitochondrial Proteins 0.000 description 4
- XUFXOAAUWZOOIT-UHFFFAOYSA-N acarviostatin I01 Natural products OC1C(O)C(NC2C(C(O)C(O)C(CO)=C2)O)C(C)OC1OC(C(C1O)O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O XUFXOAAUWZOOIT-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 230000009471 action Effects 0.000 description 4
- 230000003213 activating effect Effects 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 229940024606 amino acid Drugs 0.000 description 4
- 235000001014 amino acid Nutrition 0.000 description 4
- 150000001413 amino acids Chemical class 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- 239000001768 carboxy methyl cellulose Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 238000002648 combination therapy Methods 0.000 description 4
- 239000007891 compressed tablet Substances 0.000 description 4
- 210000002472 endoplasmic reticulum Anatomy 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 230000014509 gene expression Effects 0.000 description 4
- TWSALRJGPBVBQU-PKQQPRCHSA-N glucagon-like peptide 2 Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(O)=O)C(O)=O)[C@@H](C)CC)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)CC)C1=CC=CC=C1 TWSALRJGPBVBQU-PKQQPRCHSA-N 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 229940093915 gynecological organic acid Drugs 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 125000006588 heterocycloalkylene group Chemical group 0.000 description 4
- 230000015788 innate immune response Effects 0.000 description 4
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- 229960003105 metformin Drugs 0.000 description 4
- 229960000698 nateglinide Drugs 0.000 description 4
- 235000005985 organic acids Nutrition 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- 230000002018 overexpression Effects 0.000 description 4
- 230000036542 oxidative stress Effects 0.000 description 4
- GCYXWQUSHADNBF-AAEALURTSA-N preproglucagon 78-108 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 GCYXWQUSHADNBF-AAEALURTSA-N 0.000 description 4
- 239000003755 preservative agent Substances 0.000 description 4
- 230000000861 pro-apoptotic effect Effects 0.000 description 4
- 108020000494 protein-tyrosine phosphatase Proteins 0.000 description 4
- 229960002354 repaglinide Drugs 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 230000011664 signaling Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 125000003003 spiro group Chemical group 0.000 description 4
- 125000004434 sulfur atom Chemical group 0.000 description 4
- 239000000454 talc Substances 0.000 description 4
- 235000012222 talc Nutrition 0.000 description 4
- 229910052623 talc Inorganic materials 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- BOVGTQGAOIONJV-BETUJISGSA-N 1-[(3ar,6as)-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl]-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1C[C@H]2CCC[C@H]2C1 BOVGTQGAOIONJV-BETUJISGSA-N 0.000 description 3
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 3
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- 241000416162 Astragalus gummifer Species 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 241000283690 Bos taurus Species 0.000 description 3
- 102000004127 Cytokines Human genes 0.000 description 3
- 108090000695 Cytokines Proteins 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- 101800004266 Glucagon-like peptide 1(7-37) Proteins 0.000 description 3
- 101001059454 Homo sapiens Serine/threonine-protein kinase MARK2 Proteins 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 3
- 229930195725 Mannitol Natural products 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 3
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 3
- 108090000472 Phosphoenolpyruvate carboxykinase (ATP) Proteins 0.000 description 3
- 102100034792 Phosphoenolpyruvate carboxykinase [GTP], mitochondrial Human genes 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 102100028904 Serine/threonine-protein kinase MARK2 Human genes 0.000 description 3
- JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 3
- 229920001615 Tragacanth Polymers 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 150000001350 alkyl halides Chemical class 0.000 description 3
- 230000000692 anti-sense effect Effects 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 238000011260 co-administration Methods 0.000 description 3
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 235000019634 flavors Nutrition 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 230000030136 gastric emptying Effects 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 229960001764 glibornuride Drugs 0.000 description 3
- RMTYNAPTNBJHQI-LLDVTBCESA-N glibornuride Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)N[C@H]1[C@H](C2(C)C)CC[C@@]2(C)[C@H]1O RMTYNAPTNBJHQI-LLDVTBCESA-N 0.000 description 3
- 229960000346 gliclazide Drugs 0.000 description 3
- 229960004346 glimepiride Drugs 0.000 description 3
- WIGIZIANZCJQQY-RUCARUNLSA-N glimepiride Chemical compound O=C1C(CC)=C(C)CN1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)N[C@@H]2CC[C@@H](C)CC2)C=C1 WIGIZIANZCJQQY-RUCARUNLSA-N 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- 125000004404 heteroalkyl group Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- 230000003914 insulin secretion Effects 0.000 description 3
- 238000001361 intraarterial administration Methods 0.000 description 3
- 238000007918 intramuscular administration Methods 0.000 description 3
- 238000007912 intraperitoneal administration Methods 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000002502 liposome Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 239000000594 mannitol Substances 0.000 description 3
- 235000010355 mannitol Nutrition 0.000 description 3
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- FJXWQJRPXKUEQS-UHFFFAOYSA-N n-sulfamoylacetamide Chemical compound CC(=O)NS(N)(=O)=O FJXWQJRPXKUEQS-UHFFFAOYSA-N 0.000 description 3
- 210000002569 neuron Anatomy 0.000 description 3
- 239000006186 oral dosage form Substances 0.000 description 3
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000007909 solid dosage form Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 238000007920 subcutaneous administration Methods 0.000 description 3
- 125000000547 substituted alkyl group Chemical group 0.000 description 3
- 238000013268 sustained release Methods 0.000 description 3
- 239000012730 sustained-release form Substances 0.000 description 3
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 3
- 229960005371 tolbutamide Drugs 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 230000000699 topical effect Effects 0.000 description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 2
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 description 2
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 2
- YAYNEUUHHLGGAH-UHFFFAOYSA-N 1-chlorododecane Chemical compound CCCCCCCCCCCCCl YAYNEUUHHLGGAH-UHFFFAOYSA-N 0.000 description 2
- GCDPERPXPREHJF-UHFFFAOYSA-N 1-iodododecane Chemical compound CCCCCCCCCCCCI GCDPERPXPREHJF-UHFFFAOYSA-N 0.000 description 2
- 125000006017 1-propenyl group Chemical group 0.000 description 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 2
- MVXVYAKCVDQRLW-UHFFFAOYSA-N 1h-pyrrolo[2,3-b]pyridine Chemical compound C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 description 2
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 2
- ZRPLANDPDWYOMZ-UHFFFAOYSA-N 3-cyclopentylpropionic acid Chemical compound OC(=O)CCC1CCCC1 ZRPLANDPDWYOMZ-UHFFFAOYSA-N 0.000 description 2
- AUTCHGUUOVSZOZ-UHFFFAOYSA-N 5-[(4-methylphenyl)methyl]-1,3-thiazolidine-2,4-dione Chemical compound C1=CC(C)=CC=C1CC1C(=O)NC(=O)S1 AUTCHGUUOVSZOZ-UHFFFAOYSA-N 0.000 description 2
- YVQKIDLSVHRBGZ-UHFFFAOYSA-N 5-[[4-[2-hydroxy-2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1C(O)COC(C=C1)=CC=C1CC1SC(=O)NC1=O YVQKIDLSVHRBGZ-UHFFFAOYSA-N 0.000 description 2
- ITLAZBMGSXRIEF-UHFFFAOYSA-N 5-naphthalen-2-ylsulfonyl-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1S(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 ITLAZBMGSXRIEF-UHFFFAOYSA-N 0.000 description 2
- QSLLFYVBWXWUQT-UHFFFAOYSA-N 7-Azaindolizine Chemical compound C1=NC=CN2C=CC=C21 QSLLFYVBWXWUQT-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 229940077274 Alpha glucosidase inhibitor Drugs 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- 208000019838 Blood disease Diseases 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- 102000004657 Calcium-Calmodulin-Dependent Protein Kinase Type 2 Human genes 0.000 description 2
- 108010003721 Calcium-Calmodulin-Dependent Protein Kinase Type 2 Proteins 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- 241000283707 Capra Species 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 102000011727 Caspases Human genes 0.000 description 2
- 108010076667 Caspases Proteins 0.000 description 2
- 229920000623 Cellulose acetate phthalate Polymers 0.000 description 2
- 241000282994 Cervidae Species 0.000 description 2
- RKWGIWYCVPQPMF-UHFFFAOYSA-N Chloropropamide Chemical compound CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 RKWGIWYCVPQPMF-UHFFFAOYSA-N 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
- 229920002785 Croscarmellose sodium Polymers 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical group OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- 125000001711 D-phenylalanine group Chemical class [H]N([H])[C@@]([H])(C(=O)[*])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- 206010012655 Diabetic complications Diseases 0.000 description 2
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 2
- 102100023274 Dual specificity mitogen-activated protein kinase kinase 4 Human genes 0.000 description 2
- 241000283086 Equidae Species 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- HTQBXNHDCUEHJF-XWLPCZSASA-N Exenatide Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)NCC(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CO)C(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCSC)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 HTQBXNHDCUEHJF-XWLPCZSASA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 208000035150 Hypercholesterolemia Diseases 0.000 description 2
- 229940096915 Imidazoline receptor antagonist Drugs 0.000 description 2
- 102000003746 Insulin Receptor Human genes 0.000 description 2
- 108010001127 Insulin Receptor Proteins 0.000 description 2
- 208000032382 Ischaemic stroke Diseases 0.000 description 2
- 108010041872 Islet Amyloid Polypeptide Proteins 0.000 description 2
- 102000036770 Islet Amyloid Polypeptide Human genes 0.000 description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- IBAQFPQHRJAVAV-ULAWRXDQSA-N Miglitol Chemical compound OCCN1C[C@H](O)[C@@H](O)[C@H](O)[C@H]1CO IBAQFPQHRJAVAV-ULAWRXDQSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 102000008300 Mutant Proteins Human genes 0.000 description 2
- 108010021466 Mutant Proteins Proteins 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 108010025020 Nerve Growth Factor Proteins 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 102000023984 PPAR alpha Human genes 0.000 description 2
- 241001494479 Pecora Species 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 description 2
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 108091000080 Phosphotransferase Proteins 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 102000001253 Protein Kinase Human genes 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 2
- 229920001800 Shellac Polymers 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 241000282887 Suidae Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229940123464 Thiazolidinedione Drugs 0.000 description 2
- 102100036407 Thioredoxin Human genes 0.000 description 2
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 2
- 241000410737 Verasper moseri Species 0.000 description 2
- 230000005856 abnormality Effects 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 239000000674 adrenergic antagonist Substances 0.000 description 2
- 235000010443 alginic acid Nutrition 0.000 description 2
- 229920000615 alginic acid Polymers 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 239000003888 alpha glucosidase inhibitor Substances 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229940069428 antacid Drugs 0.000 description 2
- 239000003159 antacid agent Substances 0.000 description 2
- 239000005557 antagonist Substances 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 230000001315 anti-hyperlipaemic effect Effects 0.000 description 2
- 230000003579 anti-obesity Effects 0.000 description 2
- 229940125708 antidiabetic agent Drugs 0.000 description 2
- 239000002220 antihypertensive agent Substances 0.000 description 2
- 235000010323 ascorbic acid Nutrition 0.000 description 2
- 239000011668 ascorbic acid Substances 0.000 description 2
- 210000000227 basophil cell of anterior lobe of hypophysis Anatomy 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- 235000012216 bentonite Nutrition 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
- 235000013539 calcium stearate Nutrition 0.000 description 2
- 239000008116 calcium stearate Substances 0.000 description 2
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 2
- 125000002837 carbocyclic group Chemical group 0.000 description 2
- 125000005518 carboxamido group Chemical group 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- VDTNNGKXZGSZIP-UHFFFAOYSA-N carbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 VDTNNGKXZGSZIP-UHFFFAOYSA-N 0.000 description 2
- 229960003362 carbutamide Drugs 0.000 description 2
- 230000024245 cell differentiation Effects 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229940081734 cellulose acetate phthalate Drugs 0.000 description 2
- 239000007910 chewable tablet Substances 0.000 description 2
- 229960001761 chlorpropamide Drugs 0.000 description 2
- APEJMQOBVMLION-UHFFFAOYSA-N cinnamamide Chemical compound NC(=O)C=CC1=CC=CC=C1 APEJMQOBVMLION-UHFFFAOYSA-N 0.000 description 2
- 229960004106 citric acid Drugs 0.000 description 2
- 235000015165 citric acid Nutrition 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 229960001681 croscarmellose sodium Drugs 0.000 description 2
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 231100000433 cytotoxic Toxicity 0.000 description 2
- 230000001472 cytotoxic effect Effects 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 239000008121 dextrose Substances 0.000 description 2
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 2
- 229940038472 dicalcium phosphate Drugs 0.000 description 2
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000007884 disintegrant Substances 0.000 description 2
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical group CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 2
- 230000009977 dual effect Effects 0.000 description 2
- 230000008482 dysregulation Effects 0.000 description 2
- 239000002158 endotoxin Substances 0.000 description 2
- 238000009505 enteric coating Methods 0.000 description 2
- 239000002702 enteric coating Substances 0.000 description 2
- 230000006353 environmental stress Effects 0.000 description 2
- 229940031098 ethanolamine Drugs 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- 210000003527 eukaryotic cell Anatomy 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 235000011087 fumaric acid Nutrition 0.000 description 2
- ZJJXGWJIGJFDTL-UHFFFAOYSA-N glipizide Chemical compound C1=NC(C)=CN=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZJJXGWJIGJFDTL-UHFFFAOYSA-N 0.000 description 2
- 229960001381 glipizide Drugs 0.000 description 2
- 239000003877 glucagon like peptide 1 receptor agonist Substances 0.000 description 2
- 230000002641 glycemic effect Effects 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- RIGBPMDIGYBTBJ-UHFFFAOYSA-N glycyclamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NC1CCCCC1 RIGBPMDIGYBTBJ-UHFFFAOYSA-N 0.000 description 2
- 229950005514 glycyclamide Drugs 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 208000018706 hematopoietic system disease Diseases 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000002440 hydroxy compounds Chemical class 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- 230000036039 immunity Effects 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 2
- 230000028709 inflammatory response Effects 0.000 description 2
- 210000000936 intestine Anatomy 0.000 description 2
- 230000000302 ischemic effect Effects 0.000 description 2
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 125000001786 isothiazolyl group Chemical group 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229920006008 lipopolysaccharide Polymers 0.000 description 2
- 239000012669 liquid formulation Substances 0.000 description 2
- 239000007937 lozenge Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 2
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 2
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 229960002216 methylparaben Drugs 0.000 description 2
- 229960001110 miglitol Drugs 0.000 description 2
- 229960003365 mitiglinide Drugs 0.000 description 2
- WPGGHFDDFPHPOB-BBWFWOEESA-N mitiglinide Chemical compound C([C@@H](CC(=O)N1C[C@@H]2CCCC[C@@H]2C1)C(=O)O)C1=CC=CC=C1 WPGGHFDDFPHPOB-BBWFWOEESA-N 0.000 description 2
- TXXHDPDFNKHHGW-UHFFFAOYSA-N muconic acid Chemical group OC(=O)C=CC=CC(O)=O TXXHDPDFNKHHGW-UHFFFAOYSA-N 0.000 description 2
- FTRMOJIRMFXZJV-UHFFFAOYSA-N n-[4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenyl]-1-phenylcyclopropane-1-carboxamide Chemical compound C1CC1(C=1C=CC=CC=1)C(=O)NC(C=C1)=CC=C1CC1SC(=O)NC1=O FTRMOJIRMFXZJV-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 210000005036 nerve Anatomy 0.000 description 2
- PKWDZWYVIHVNKS-UHFFFAOYSA-N netoglitazone Chemical compound FC1=CC=CC=C1COC1=CC=C(C=C(CC2C(NC(=O)S2)=O)C=C2)C2=C1 PKWDZWYVIHVNKS-UHFFFAOYSA-N 0.000 description 2
- 230000014511 neuron projection development Effects 0.000 description 2
- 235000001968 nicotinic acid Nutrition 0.000 description 2
- 239000011664 nicotinic acid Substances 0.000 description 2
- 102000039446 nucleic acids Human genes 0.000 description 2
- 108020004707 nucleic acids Proteins 0.000 description 2
- 150000007523 nucleic acids Chemical class 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical group CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Chemical group CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 210000000496 pancreas Anatomy 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 230000007170 pathology Effects 0.000 description 2
- 239000001814 pectin Substances 0.000 description 2
- 235000010987 pectin Nutrition 0.000 description 2
- 229920001277 pectin Polymers 0.000 description 2
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 2
- 108091008725 peroxisome proliferator-activated receptors alpha Proteins 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- AFOGBLYPWJJVAL-UHFFFAOYSA-N phenbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=CC=C1 AFOGBLYPWJJVAL-UHFFFAOYSA-N 0.000 description 2
- 229950008557 phenbutamide Drugs 0.000 description 2
- DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 230000000865 phosphorylative effect Effects 0.000 description 2
- 102000020233 phosphotransferase Human genes 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 229960005095 pioglitazone Drugs 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
- 108060006633 protein kinase Proteins 0.000 description 2
- DVUBDHRTVYLIPA-UHFFFAOYSA-N pyrazolo[1,5-a]pyridine Chemical compound C1=CC=CN2N=CC=C21 DVUBDHRTVYLIPA-UHFFFAOYSA-N 0.000 description 2
- NHZMQXZHNVQTQA-UHFFFAOYSA-N pyridoxamine Chemical compound CC1=NC=C(CO)C(CN)=C1O NHZMQXZHNVQTQA-UHFFFAOYSA-N 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 230000020129 regulation of cell death Effects 0.000 description 2
- 229960004586 rosiglitazone Drugs 0.000 description 2
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical group OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000004208 shellac Substances 0.000 description 2
- 229940113147 shellac Drugs 0.000 description 2
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 2
- 235000013874 shellac Nutrition 0.000 description 2
- 230000035939 shock Effects 0.000 description 2
- 230000019491 signal transduction Effects 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000008117 stearic acid Chemical group 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 230000003956 synaptic plasticity Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- RMMXLENWKUUMAY-UHFFFAOYSA-N telmisartan Chemical compound CCCC1=NC2=C(C)C=C(C=3N(C4=CC=CC=C4N=3)C)C=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O RMMXLENWKUUMAY-UHFFFAOYSA-N 0.000 description 2
- CXGTZJYQWSUFET-IBGZPJMESA-N tesaglitazar Chemical compound C1=CC(C[C@H](OCC)C(O)=O)=CC=C1OCCC1=CC=C(OS(C)(=O)=O)C=C1 CXGTZJYQWSUFET-IBGZPJMESA-N 0.000 description 2
- 229950004704 tesaglitazar Drugs 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 2
- 150000001467 thiazolidinediones Chemical class 0.000 description 2
- 125000004001 thioalkyl group Chemical group 0.000 description 2
- 108060008226 thioredoxin Proteins 0.000 description 2
- OUDSBRTVNLOZBN-UHFFFAOYSA-N tolazamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1CCCCCC1 OUDSBRTVNLOZBN-UHFFFAOYSA-N 0.000 description 2
- 229960002277 tolazamide Drugs 0.000 description 2
- 235000010487 tragacanth Nutrition 0.000 description 2
- 239000000196 tragacanth Substances 0.000 description 2
- 229940116362 tragacanth Drugs 0.000 description 2
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 229960000281 trometamol Drugs 0.000 description 2
- 229960004441 tyrosine Drugs 0.000 description 2
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 2
- 229910052720 vanadium Inorganic materials 0.000 description 2
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- DBGIVFWFUFKIQN-VIFPVBQESA-N (+)-Fenfluramine Chemical compound CCN[C@@H](C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-VIFPVBQESA-N 0.000 description 1
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical compound CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 description 1
- REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 description 1
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 1
- 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
- VLPIATFUUWWMKC-SNVBAGLBSA-N (2r)-1-(2,6-dimethylphenoxy)propan-2-amine Chemical compound C[C@@H](N)COC1=C(C)C=CC=C1C VLPIATFUUWWMKC-SNVBAGLBSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- BLWKWOVOFWHFLD-FQEVSTJZSA-N (2s)-2-(2-benzoylanilino)-3-(4-hydroxyphenyl)propanoic acid Chemical class C([C@@H](C(=O)O)NC=1C(=CC=CC=1)C(=O)C=1C=CC=CC=1)C1=CC=C(O)C=C1 BLWKWOVOFWHFLD-FQEVSTJZSA-N 0.000 description 1
- ZXEIEKDGPVTZLD-NDEPHWFRSA-N (2s)-2-dodecylsulfanyl-n-(4-hydroxy-2,3,5-trimethylphenyl)-2-phenylacetamide Chemical compound O=C([C@@H](SCCCCCCCCCCCC)C=1C=CC=CC=1)NC1=CC(C)=C(O)C(C)=C1C ZXEIEKDGPVTZLD-NDEPHWFRSA-N 0.000 description 1
- ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 description 1
- QCVNMNYRNIMDKV-QGZVFWFLSA-N (3r)-2'-[(4-bromo-2-fluorophenyl)methyl]spiro[pyrrolidine-3,4'-pyrrolo[1,2-a]pyrazine]-1',2,3',5-tetrone Chemical compound FC1=CC(Br)=CC=C1CN1C(=O)[C@@]2(C(NC(=O)C2)=O)N2C=CC=C2C1=O QCVNMNYRNIMDKV-QGZVFWFLSA-N 0.000 description 1
- VMDKRSNUUUUARH-MQDBWYGVSA-N (3s)-4-[[(2s)-1-[[(2s)-2-[[(2s)-3-(1h-indol-3-yl)-2-[[2-[[(2s)-2-[[2-(4-sulfooxyphenyl)acetyl]amino]hexanoyl]amino]acetyl]amino]propanoyl]amino]hexanoyl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(methylamino)-4-oxobutanoic acid Chemical compound N([C@@H](CCCC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCCC)C(=O)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CC(O)=O)NC)C(=O)CC1=CC=C(OS(O)(=O)=O)C=C1 VMDKRSNUUUUARH-MQDBWYGVSA-N 0.000 description 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 1
- AGBQKNBQESQNJD-SSDOTTSWSA-N (R)-lipoic acid Chemical compound OC(=O)CCCC[C@@H]1CCSS1 AGBQKNBQESQNJD-SSDOTTSWSA-N 0.000 description 1
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- DZKRDHLYQRTDBU-UPHRSURJSA-N (z)-but-2-enediperoxoic acid Chemical compound OOC(=O)\C=C/C(=O)OO DZKRDHLYQRTDBU-UPHRSURJSA-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
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- GWYPDXLJACEENP-UHFFFAOYSA-N 1,3-cycloheptadiene Chemical compound C1CC=CC=CC1 GWYPDXLJACEENP-UHFFFAOYSA-N 0.000 description 1
- IGERFAHWSHDDHX-UHFFFAOYSA-N 1,3-dioxanyl Chemical group [CH]1OCCCO1 IGERFAHWSHDDHX-UHFFFAOYSA-N 0.000 description 1
- 125000005940 1,4-dioxanyl group Chemical group 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- KMXPHBJUGYLXDM-UHFFFAOYSA-N 1-(7-hydroxy-6,6-dimethyl-7,8-dihydropyrano[2,3-f][2,1,3]benzoxadiazol-8-yl)piperidin-2-one Chemical compound OC1C(C)(C)OC2=CC3=NON=C3C=C2C1N1CCCCC1=O KMXPHBJUGYLXDM-UHFFFAOYSA-N 0.000 description 1
- WSDSEIUBXJOEIQ-UHFFFAOYSA-N 1-[1-(3-ethoxyphenyl)-4-methylcyclohexyl]-4-phenylpiperazine;methanesulfonic acid Chemical compound CS(O)(=O)=O.CCOC1=CC=CC(C2(CCC(C)CC2)N2CCN(CC2)C=2C=CC=CC=2)=C1 WSDSEIUBXJOEIQ-UHFFFAOYSA-N 0.000 description 1
- MYMSJFSOOQERIO-UHFFFAOYSA-N 1-bromodecane Chemical compound CCCCCCCCCCBr MYMSJFSOOQERIO-UHFFFAOYSA-N 0.000 description 1
- WSULSMOGMLRGKU-UHFFFAOYSA-N 1-bromooctadecane Chemical compound CCCCCCCCCCCCCCCCCCBr WSULSMOGMLRGKU-UHFFFAOYSA-N 0.000 description 1
- KOFZTCSTGIWCQG-UHFFFAOYSA-N 1-bromotetradecane Chemical compound CCCCCCCCCCCCCCBr KOFZTCSTGIWCQG-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- ZTEHOZMYMCEYRM-UHFFFAOYSA-N 1-chlorodecane Chemical compound CCCCCCCCCCCl ZTEHOZMYMCEYRM-UHFFFAOYSA-N 0.000 description 1
- VUQPJRPDRDVQMN-UHFFFAOYSA-N 1-chlorooctadecane Chemical compound CCCCCCCCCCCCCCCCCCCl VUQPJRPDRDVQMN-UHFFFAOYSA-N 0.000 description 1
- RNHWYOLIEJIAMV-UHFFFAOYSA-N 1-chlorotetradecane Chemical compound CCCCCCCCCCCCCCCl RNHWYOLIEJIAMV-UHFFFAOYSA-N 0.000 description 1
- SKIDNYUZJPMKFC-UHFFFAOYSA-N 1-iododecane Chemical compound CCCCCCCCCCI SKIDNYUZJPMKFC-UHFFFAOYSA-N 0.000 description 1
- FHQCFGPKNSSISL-UHFFFAOYSA-N 1-iodotetradecane Chemical compound CCCCCCCCCCCCCCI FHQCFGPKNSSISL-UHFFFAOYSA-N 0.000 description 1
- AMMPLVWPWSYRDR-UHFFFAOYSA-N 1-methylbicyclo[2.2.2]oct-2-ene-4-carboxylic acid Chemical compound C1CC2(C(O)=O)CCC1(C)C=C2 AMMPLVWPWSYRDR-UHFFFAOYSA-N 0.000 description 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- 102000004277 11-beta-hydroxysteroid dehydrogenases Human genes 0.000 description 1
- 108090000874 11-beta-hydroxysteroid dehydrogenases Proteins 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- XLKDJOPOOHHZAN-UHFFFAOYSA-N 1h-pyrrolo[2,3-c]pyridine Chemical compound C1=NC=C2NC=CC2=C1 XLKDJOPOOHHZAN-UHFFFAOYSA-N 0.000 description 1
- XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 description 1
- SRSKXJVMVSSSHB-UHFFFAOYSA-N 1h-pyrrolo[3,2-c]pyridine Chemical compound N1=CC=C2NC=CC2=C1 SRSKXJVMVSSSHB-UHFFFAOYSA-N 0.000 description 1
- XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 1
- WHORNCXVTJMYBH-UHFFFAOYSA-N 2,2-dimethyl-n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)propanamide Chemical compound N12N=CC=C2N=C(NC(=O)C(C)(C)C)C=C1N1CCOCC1 WHORNCXVTJMYBH-UHFFFAOYSA-N 0.000 description 1
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 1
- NTOIKDYVJIWVSU-UHFFFAOYSA-N 2,3-dihydroxy-2,3-bis(4-methylbenzoyl)butanedioic acid Chemical compound C1=CC(C)=CC=C1C(=O)C(O)(C(O)=O)C(O)(C(O)=O)C(=O)C1=CC=C(C)C=C1 NTOIKDYVJIWVSU-UHFFFAOYSA-N 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- HCSBTDBGTNZOAB-UHFFFAOYSA-N 2,3-dinitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O HCSBTDBGTNZOAB-UHFFFAOYSA-N 0.000 description 1
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-Dihydroxybenzoic acid Natural products OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 1
- WGIMXKDCVCTHGW-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCOCCO WGIMXKDCVCTHGW-UHFFFAOYSA-N 0.000 description 1
- YGTUPRIZNBMOFV-UHFFFAOYSA-N 2-(4-hydroxybenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=C(O)C=C1 YGTUPRIZNBMOFV-UHFFFAOYSA-N 0.000 description 1
- FKOKUHFZNIUSLW-UHFFFAOYSA-N 2-Hydroxypropyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(C)O FKOKUHFZNIUSLW-UHFFFAOYSA-N 0.000 description 1
- CMLUGNQVANVZHY-POURPWNDSA-N 2-[1-[2-[(3r,5s)-1-(3-acetyloxy-2,2-dimethylpropyl)-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-5h-4,1-benzoxazepin-3-yl]acetyl]piperidin-4-yl]acetic acid Chemical compound COC1=CC=CC([C@@H]2C3=CC(Cl)=CC=C3N(CC(C)(C)COC(C)=O)C(=O)[C@@H](CC(=O)N3CCC(CC(O)=O)CC3)O2)=C1OC CMLUGNQVANVZHY-POURPWNDSA-N 0.000 description 1
- NSVFSAJIGAJDMR-UHFFFAOYSA-N 2-[benzyl(phenyl)amino]ethyl 5-(5,5-dimethyl-2-oxido-1,3,2-dioxaphosphinan-2-yl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate Chemical compound CC=1NC(C)=C(C(=O)OCCN(CC=2C=CC=CC=2)C=2C=CC=CC=2)C(C=2C=C(C=CC=2)[N+]([O-])=O)C=1P1(=O)OCC(C)(C)CO1 NSVFSAJIGAJDMR-UHFFFAOYSA-N 0.000 description 1
- BJBCSGQLZQGGIQ-QGZVFWFLSA-N 2-acetamidoethyl (2r)-2-(4-chlorophenyl)-2-[3-(trifluoromethyl)phenoxy]acetate Chemical compound O([C@@H](C(=O)OCCNC(=O)C)C=1C=CC(Cl)=CC=1)C1=CC=CC(C(F)(F)F)=C1 BJBCSGQLZQGGIQ-QGZVFWFLSA-N 0.000 description 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- 229940013085 2-diethylaminoethanol Drugs 0.000 description 1
- NRMGFQFLHNYNCY-UHFFFAOYSA-N 2-hydroxyethanesulfonic acid;hydroiodide Chemical compound I.OCCS(O)(=O)=O NRMGFQFLHNYNCY-UHFFFAOYSA-N 0.000 description 1
- UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical group C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 description 1
- ANGGPYSFTXVERY-UHFFFAOYSA-N 2-iodo-2-methylpropane Chemical compound CC(C)(C)I ANGGPYSFTXVERY-UHFFFAOYSA-N 0.000 description 1
- 125000006029 2-methyl-2-butenyl group Chemical group 0.000 description 1
- VFPIZPPYBPFRRQ-UHFFFAOYSA-N 2-methyl-7-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-5-amine Chemical compound N12N=C(C)C=C2N=C(N)C=C1C1=CC=C(C)C=C1 VFPIZPPYBPFRRQ-UHFFFAOYSA-N 0.000 description 1
- NTVOQWGKFCKQND-UHFFFAOYSA-N 2-methyl-n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)propanamide Chemical compound N12N=CC=C2N=C(NC(=O)C(C)C)C=C1N1CCOCC1 NTVOQWGKFCKQND-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- 229940080296 2-naphthalenesulfonate Drugs 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
- BCSVCWVQNOXFGL-UHFFFAOYSA-N 3,4-dihydro-4-oxo-3-((5-trifluoromethyl-2-benzothiazolyl)methyl)-1-phthalazine acetic acid Chemical compound O=C1C2=CC=CC=C2C(CC(=O)O)=NN1CC1=NC2=CC(C(F)(F)F)=CC=C2S1 BCSVCWVQNOXFGL-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- UYGZODVVDUIDDQ-UHFFFAOYSA-N 3-[(2,4-dichlorophenyl)methyl]-2-methyl-n-pentylsulfonylbenzimidazole-5-carboxamide Chemical compound C12=CC(C(=O)NS(=O)(=O)CCCCC)=CC=C2N=C(C)N1CC1=CC=C(Cl)C=C1Cl UYGZODVVDUIDDQ-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
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- WZFZJEPHYDDFCT-UHFFFAOYSA-N 3-chloro-2-methyl-n-[4-[2-(3-oxomorpholin-4-yl)ethyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound CC1=C(Cl)C=CC=C1S(=O)(=O)NC1=NC(CCN2C(COCC2)=O)=CS1 WZFZJEPHYDDFCT-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- JGSIAOZAXBWRFO-UHFFFAOYSA-N 3-methylsulfanyl-1-phenyl-4,5-dihydrobenzo[g]indazole Chemical compound C1CC2=CC=CC=C2C2=C1C(SC)=NN2C1=CC=CC=C1 JGSIAOZAXBWRFO-UHFFFAOYSA-N 0.000 description 1
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DBTMGCOVALSLOR-UHFFFAOYSA-N 32-alpha-galactosyl-3-alpha-galactosyl-galactose Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(OC2C(C(CO)OC(O)C2O)O)OC(CO)C1O DBTMGCOVALSLOR-UHFFFAOYSA-N 0.000 description 1
- UBOOKRVGOBKDMM-UHFFFAOYSA-N 3h-imidazo[4,5-c]pyridine Chemical compound C1=NC=C2NC=NC2=C1 UBOOKRVGOBKDMM-UHFFFAOYSA-N 0.000 description 1
- VNEYGCYWOLROCZ-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[2-methyl-7-(1,4-oxazepan-4-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=C(N2CCOCCC2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 VNEYGCYWOLROCZ-UHFFFAOYSA-N 0.000 description 1
- SHMSACOJWCVDRG-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)-n-[7-[4-(methoxymethyl)piperidin-1-yl]pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1CC(COC)CCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 SHMSACOJWCVDRG-UHFFFAOYSA-N 0.000 description 1
- UZKXVFBKGNVTFE-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(2-methylimidazol-1-yl)-5-[3-(2-methylphenoxy)propyl]-1,3-oxazole Chemical compound CC1=NC=CN1C(O1)=NC(C=2C=CC(Cl)=CC=2)=C1CCCOC1=CC=CC=C1C UZKXVFBKGNVTFE-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- QBQLYIISSRXYKL-UHFFFAOYSA-N 4-[[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methyl]-1,2-oxazolidine-3,5-dione Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=C1)=CC=C1CC1C(=O)NOC1=O QBQLYIISSRXYKL-UHFFFAOYSA-N 0.000 description 1
- FWMNVWWHGCHHJJ-SKKKGAJSSA-N 4-amino-1-[(2r)-6-amino-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]piperidine-4-carboxylic acid Chemical compound C([C@H](C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCCCN)C(=O)N1CCC(N)(CC1)C(O)=O)NC(=O)[C@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 FWMNVWWHGCHHJJ-SKKKGAJSSA-N 0.000 description 1
- RJWBTWIBUIGANW-UHFFFAOYSA-N 4-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-N 0.000 description 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- HYANODCDSONKCC-UHFFFAOYSA-N 4-tert-butyl-n-[7-(3-imidazol-1-ylpropylamino)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(NCCCN2C=NC=C2)=C1 HYANODCDSONKCC-UHFFFAOYSA-N 0.000 description 1
- JTIDPFAHDOOODC-UHFFFAOYSA-N 4-tert-butyl-n-[7-(furan-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(C2=COC=C2)=C1 JTIDPFAHDOOODC-UHFFFAOYSA-N 0.000 description 1
- UVIUIRLFAWUCHL-UHFFFAOYSA-N 4-tert-butyl-n-[7-[2-(2-hydroxyethyl)piperidin-1-yl]pyrazolo[1,5-a]pyrimidin-5-yl]benzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2C(CCCC2)CCO)=C1 UVIUIRLFAWUCHL-UHFFFAOYSA-N 0.000 description 1
- 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 description 1
- AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 description 1
- HMXDWDSNPRNUKI-UHFFFAOYSA-N 5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethyl-N-(1-piperidinyl)-3-pyrazolecarboxamide Chemical compound CCC=1C(C(=O)NN2CCCCC2)=NN(C=2C(=CC(Cl)=CC=2)Cl)C=1C1=CC=C(Br)C=C1 HMXDWDSNPRNUKI-UHFFFAOYSA-N 0.000 description 1
- NFFXEUUOMTXWCX-UHFFFAOYSA-N 5-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]-2-methoxy-n-[[4-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound C1=C(C(=O)NCC=2C=CC(=CC=2)C(F)(F)F)C(OC)=CC=C1CC1SC(=O)NC1=O NFFXEUUOMTXWCX-UHFFFAOYSA-N 0.000 description 1
- GWZJXMRSPIFFAK-UHFFFAOYSA-N 5-[(2-naphthalen-2-yl-1,3-benzoxazol-5-yl)methyl]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1CC1=CC=C(OC(=N2)C=3C=C4C=CC=CC4=CC=3)C2=C1 GWZJXMRSPIFFAK-UHFFFAOYSA-N 0.000 description 1
- MVDXXGIBARMXSA-PYUWXLGESA-N 5-[[(2r)-2-benzyl-3,4-dihydro-2h-chromen-6-yl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1CC1=CC=C(O[C@@H](CC=2C=CC=CC=2)CC2)C2=C1 MVDXXGIBARMXSA-PYUWXLGESA-N 0.000 description 1
- PCAZCAZVHLGDBA-UHFFFAOYSA-N 5-[[4-(2-indol-1-ylethoxy)phenyl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1CC(C=C1)=CC=C1OCCN1C2=CC=CC=C2C=C1 PCAZCAZVHLGDBA-UHFFFAOYSA-N 0.000 description 1
- HAAXAFNSRADSMK-UHFFFAOYSA-N 5-[[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]-1-benzothiophen-7-yl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCOC(C=1C=CSC=11)=CC=C1CC1SC(=O)NC1=O HAAXAFNSRADSMK-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- ALHGXFGAYGLWBR-UHFFFAOYSA-N 7-(4-methylphenyl)pyrazolo[1,5-a]pyrimidin-5-amine Chemical compound C1=CC(C)=CC=C1C1=CC(N)=NC2=CC=NN12 ALHGXFGAYGLWBR-UHFFFAOYSA-N 0.000 description 1
- BIDCRTFURBTDBR-UHFFFAOYSA-N 7-(5-methylthiophen-2-yl)pyrazolo[1,5-a]pyrimidin-5-amine Chemical compound S1C(C)=CC=C1C1=CC(N)=NC2=CC=NN12 BIDCRTFURBTDBR-UHFFFAOYSA-N 0.000 description 1
- LYYXFKZYKBRFFP-UHFFFAOYSA-N 7-chloro-2-(2,2,2-trifluoroethyl)pyrazolo[1,5-a]pyrimidin-5-amine Chemical compound N1=C(N)C=C(Cl)N2N=C(CC(F)(F)F)C=C21 LYYXFKZYKBRFFP-UHFFFAOYSA-N 0.000 description 1
- HAJOULVMKQOUPF-UHFFFAOYSA-N 7-chloro-2-(trifluoromethyl)pyrazolo[1,5-a]pyrimidin-5-amine Chemical compound N1=C(N)C=C(Cl)N2N=C(C(F)(F)F)C=C21 HAJOULVMKQOUPF-UHFFFAOYSA-N 0.000 description 1
- URNNIMJCIUNJSO-UHFFFAOYSA-N 7-chloro-2-cyclopropylpyrazolo[1,5-a]pyrimidin-5-amine Chemical compound C1=C2N=C(N)C=C(Cl)N2N=C1C1CC1 URNNIMJCIUNJSO-UHFFFAOYSA-N 0.000 description 1
- XLGPUCDSAWQEQE-UHFFFAOYSA-N 7-chloro-2-ethylpyrazolo[1,5-a]pyrimidin-5-amine Chemical compound N1=C(N)C=C(Cl)N2N=C(CC)C=C21 XLGPUCDSAWQEQE-UHFFFAOYSA-N 0.000 description 1
- RJHIWPYXWSREJB-UHFFFAOYSA-N 7-chloro-2-methoxypyrazolo[1,5-a]pyrimidin-5-amine Chemical compound N1=C(N)C=C(Cl)N2N=C(OC)C=C21 RJHIWPYXWSREJB-UHFFFAOYSA-N 0.000 description 1
- VOWVPHOKWZLZLV-UHFFFAOYSA-N 7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-amine Chemical compound N1=C(N)C=C(Cl)N2N=C(C)C=C21 VOWVPHOKWZLZLV-UHFFFAOYSA-N 0.000 description 1
- RQDAMMMLPCIRCS-UHFFFAOYSA-N 7-chloropyrazolo[1,5-a]pyrimidin-5-amine Chemical compound N1=C(N)C=C(Cl)N2N=CC=C21 RQDAMMMLPCIRCS-UHFFFAOYSA-N 0.000 description 1
- YPWFNLSXQIGJCK-UHFFFAOYSA-N 7-oxabicyclo[2.2.1]heptane Chemical compound C1CC2CCC1O2 YPWFNLSXQIGJCK-UHFFFAOYSA-N 0.000 description 1
- VTWFFXXAMBTUBY-UHFFFAOYSA-N 7-thiophen-2-ylpyrazolo[1,5-a]pyrimidin-5-amine Chemical compound N12N=CC=C2N=C(N)C=C1C1=CC=CS1 VTWFFXXAMBTUBY-UHFFFAOYSA-N 0.000 description 1
- JJTNLWSCFYERCK-UHFFFAOYSA-N 7h-pyrrolo[2,3-d]pyrimidine Chemical compound N1=CN=C2NC=CC2=C1 JJTNLWSCFYERCK-UHFFFAOYSA-N 0.000 description 1
- 239000005541 ACE inhibitor Substances 0.000 description 1
- 235000006491 Acacia senegal Nutrition 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229940123413 Angiotensin II antagonist Drugs 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 1
- XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 description 1
- 108010028845 BIM 23190 Proteins 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 229940123208 Biguanide Drugs 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 102000004219 Brain-derived neurotrophic factor Human genes 0.000 description 1
- 108090000715 Brain-derived neurotrophic factor Proteins 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 239000002083 C09CA01 - Losartan Substances 0.000 description 1
- 239000002080 C09CA02 - Eprosartan Substances 0.000 description 1
- 239000002947 C09CA04 - Irbesartan Substances 0.000 description 1
- 239000002081 C09CA05 - Tasosartan Substances 0.000 description 1
- 239000005537 C09CA07 - Telmisartan Substances 0.000 description 1
- 239000002051 C09CA08 - Olmesartan medoxomil Substances 0.000 description 1
- QOGOBFQCVHHHGP-UHFFFAOYSA-N CC1=NN2C(=C1)N=C(C=C2N3CCC(CC3)C(C)(C)O)NC(=O)C4=CC=CC=C4 Chemical compound CC1=NN2C(=C1)N=C(C=C2N3CCC(CC3)C(C)(C)O)NC(=O)C4=CC=CC=C4 QOGOBFQCVHHHGP-UHFFFAOYSA-N 0.000 description 1
- TWJIYUBTNLAXLO-UHFFFAOYSA-N CC1=NN2C(C3=CC=CC=C3)=CC(C(C3)OC4=C3C=CC(C(N)=O)=C4)=NC2=C1 Chemical compound CC1=NN2C(C3=CC=CC=C3)=CC(C(C3)OC4=C3C=CC(C(N)=O)=C4)=NC2=C1 TWJIYUBTNLAXLO-UHFFFAOYSA-N 0.000 description 1
- CYDHMCZJLQFAFL-UHFFFAOYSA-N CS(CCOC1=CC(NC(C2=CC=CC=C2)=O)=NC2=CC=NN12)(=O)=O Chemical compound CS(CCOC1=CC(NC(C2=CC=CC=C2)=O)=NC2=CC=NN12)(=O)=O CYDHMCZJLQFAFL-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical class [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- 229940127291 Calcium channel antagonist Drugs 0.000 description 1
- GHOSNRCGJFBJIB-UHFFFAOYSA-N Candesartan cilexetil Chemical compound C=12N(CC=3C=CC(=CC=3)C=3C(=CC=CC=3)C3=NNN=N3)C(OCC)=NC2=CC=CC=1C(=O)OC(C)OC(=O)OC1CCCCC1 GHOSNRCGJFBJIB-UHFFFAOYSA-N 0.000 description 1
- 229940122820 Cannabinoid receptor antagonist Drugs 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 239000005973 Carvone Substances 0.000 description 1
- 102000053642 Catalytic RNA Human genes 0.000 description 1
- 108090000994 Catalytic RNA Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 101800001982 Cholecystokinin Proteins 0.000 description 1
- 102100025841 Cholecystokinin Human genes 0.000 description 1
- 108010005939 Ciliary Neurotrophic Factor Proteins 0.000 description 1
- 102100031614 Ciliary neurotrophic factor Human genes 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
- BMOVQUBVGICXQN-UHFFFAOYSA-N Clinofibrate Chemical compound C1=CC(OC(C)(CC)C(O)=O)=CC=C1C1(C=2C=CC(OC(C)(CC)C(O)=O)=CC=2)CCCCC1 BMOVQUBVGICXQN-UHFFFAOYSA-N 0.000 description 1
- GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- AAWZDTNXLSGCEK-UHFFFAOYSA-N Cordycepinsaeure Natural products OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- TVZCRIROJQEVOT-CABCVRRESA-N Cromakalim Chemical compound N1([C@@H]2C3=CC(=CC=C3OC([C@H]2O)(C)C)C#N)CCCC1=O TVZCRIROJQEVOT-CABCVRRESA-N 0.000 description 1
- UDIPTWFVPPPURJ-UHFFFAOYSA-M Cyclamate Chemical compound [Na+].[O-]S(=O)(=O)NC1CCCCC1 UDIPTWFVPPPURJ-UHFFFAOYSA-M 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Chemical group OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- RXVWSYJTUUKTEA-UHFFFAOYSA-N D-maltotriose Natural products OC1C(O)C(OC(C(O)CO)C(O)C(O)C=O)OC(CO)C1OC1C(O)C(O)C(O)C(CO)O1 RXVWSYJTUUKTEA-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- 102100023275 Dual specificity mitogen-activated protein kinase kinase 3 Human genes 0.000 description 1
- 101710146518 Dual specificity mitogen-activated protein kinase kinase 4 Proteins 0.000 description 1
- 102100023401 Dual specificity mitogen-activated protein kinase kinase 6 Human genes 0.000 description 1
- 102100023332 Dual specificity mitogen-activated protein kinase kinase 7 Human genes 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 108010061435 Enalapril Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241001125671 Eretmochelys imbricata Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 108010011459 Exenatide Proteins 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- 102100023374 Forkhead box protein M1 Human genes 0.000 description 1
- 102000027487 Fructose-Bisphosphatase Human genes 0.000 description 1
- 108010017464 Fructose-Bisphosphatase Proteins 0.000 description 1
- 102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 1
- 108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 1
- DSLZVSRJTYRBFB-UHFFFAOYSA-N Galactaric acid Natural products OC(=O)C(O)C(O)C(O)C(O)C(O)=O DSLZVSRJTYRBFB-UHFFFAOYSA-N 0.000 description 1
- 101800001586 Ghrelin Proteins 0.000 description 1
- 102400000442 Ghrelin-28 Human genes 0.000 description 1
- 108010024044 Glucagon-Like Peptide-2 Receptor Proteins 0.000 description 1
- 229940089838 Glucagon-like peptide 1 receptor agonist Drugs 0.000 description 1
- 102100032879 Glucagon-like peptide 2 receptor Human genes 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Chemical group OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 1
- 206010019663 Hepatic failure Diseases 0.000 description 1
- 239000004284 Heptyl p-hydroxybenzoate Substances 0.000 description 1
- 229940122957 Histamine H2 receptor antagonist Drugs 0.000 description 1
- 101001115394 Homo sapiens Dual specificity mitogen-activated protein kinase kinase 3 Proteins 0.000 description 1
- 101001115395 Homo sapiens Dual specificity mitogen-activated protein kinase kinase 4 Proteins 0.000 description 1
- 101000624426 Homo sapiens Dual specificity mitogen-activated protein kinase kinase 6 Proteins 0.000 description 1
- 101000624594 Homo sapiens Dual specificity mitogen-activated protein kinase kinase 7 Proteins 0.000 description 1
- 101000907578 Homo sapiens Forkhead box protein M1 Proteins 0.000 description 1
- 101000976075 Homo sapiens Insulin Proteins 0.000 description 1
- 101001018141 Homo sapiens Mitogen-activated protein kinase kinase kinase 2 Proteins 0.000 description 1
- 101001018145 Homo sapiens Mitogen-activated protein kinase kinase kinase 3 Proteins 0.000 description 1
- 101001018147 Homo sapiens Mitogen-activated protein kinase kinase kinase 4 Proteins 0.000 description 1
- 101001055097 Homo sapiens Mitogen-activated protein kinase kinase kinase 6 Proteins 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 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 1
- 102100025087 Insulin receptor substrate 1 Human genes 0.000 description 1
- 101710201824 Insulin receptor substrate 1 Proteins 0.000 description 1
- 229940122355 Insulin sensitizer Drugs 0.000 description 1
- 102000000589 Interleukin-1 Human genes 0.000 description 1
- 108010002352 Interleukin-1 Proteins 0.000 description 1
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical class N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 1
- 102000005237 Isophane Insulin Human genes 0.000 description 1
- 108010081368 Isophane Insulin Proteins 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 102000016267 Leptin Human genes 0.000 description 1
- 108010092277 Leptin Proteins 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 102000001291 MAP Kinase Kinase Kinase Human genes 0.000 description 1
- 108010075654 MAP Kinase Kinase Kinase 1 Proteins 0.000 description 1
- 230000037364 MAPK/ERK pathway Effects 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- ZPXSCAKFGYXMGA-UHFFFAOYSA-N Mazindol Chemical compound N12CCN=C2C2=CC=CC=C2C1(O)C1=CC=C(Cl)C=C1 ZPXSCAKFGYXMGA-UHFFFAOYSA-N 0.000 description 1
- 102000029828 Melanin-concentrating hormone receptor Human genes 0.000 description 1
- 108010047068 Melanin-concentrating hormone receptor Proteins 0.000 description 1
- 101710151321 Melanostatin Proteins 0.000 description 1
- 244000246386 Mentha pulegium Species 0.000 description 1
- 235000016257 Mentha pulegium Nutrition 0.000 description 1
- 235000004357 Mentha x piperita Nutrition 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 108050002686 Mitochondrial brown fat uncoupling protein 1 Proteins 0.000 description 1
- 102100040200 Mitochondrial uncoupling protein 2 Human genes 0.000 description 1
- 101710112393 Mitochondrial uncoupling protein 2 Proteins 0.000 description 1
- 102100040216 Mitochondrial uncoupling protein 3 Human genes 0.000 description 1
- 101710112412 Mitochondrial uncoupling protein 3 Proteins 0.000 description 1
- 102100033115 Mitogen-activated protein kinase kinase kinase 1 Human genes 0.000 description 1
- 102100033058 Mitogen-activated protein kinase kinase kinase 2 Human genes 0.000 description 1
- 102100033059 Mitogen-activated protein kinase kinase kinase 3 Human genes 0.000 description 1
- 102100033060 Mitogen-activated protein kinase kinase kinase 4 Human genes 0.000 description 1
- 101710164337 Mitogen-activated protein kinase kinase kinase 5 Proteins 0.000 description 1
- 102100026889 Mitogen-activated protein kinase kinase kinase 6 Human genes 0.000 description 1
- 108030005453 Mitogen-activated protein kinase kinase kinases Proteins 0.000 description 1
- PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 description 1
- TXXHDPDFNKHHGW-CCAGOZQPSA-N Muconic acid Chemical group OC(=O)\C=C/C=C\C(O)=O TXXHDPDFNKHHGW-CCAGOZQPSA-N 0.000 description 1
- IRLWJILLXJGJTD-UHFFFAOYSA-N Muraglitazar Chemical compound C1=CC(OC)=CC=C1OC(=O)N(CC(O)=O)CC(C=C1)=CC=C1OCCC1=C(C)OC(C=2C=CC=CC=2)=N1 IRLWJILLXJGJTD-UHFFFAOYSA-N 0.000 description 1
- 206010028289 Muscle atrophy Diseases 0.000 description 1
- ONXPDKGXOOORHB-BYPYZUCNSA-N N(5)-methyl-L-glutamine Chemical compound CNC(=O)CC[C@H](N)C(O)=O ONXPDKGXOOORHB-BYPYZUCNSA-N 0.000 description 1
- OTAZEZHFFFBTMX-UHFFFAOYSA-N N-(2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-yl)cyclopropanecarboxamide Chemical compound CC1=NN2C(=CC(=NC2=C1)NC(=O)C3CC3)C4=CC=CC=C4 OTAZEZHFFFBTMX-UHFFFAOYSA-N 0.000 description 1
- QIAFMBKCNZACKA-UHFFFAOYSA-N N-benzoylglycine Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1 QIAFMBKCNZACKA-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
- KCTZOTUQSGYWLV-UHFFFAOYSA-N N1C=NC=C2N=CC=C21 Chemical compound N1C=NC=C2N=CC=C21 KCTZOTUQSGYWLV-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 102000015336 Nerve Growth Factor Human genes 0.000 description 1
- 102000007072 Nerve Growth Factors Human genes 0.000 description 1
- 102400000064 Neuropeptide Y Human genes 0.000 description 1
- 108090000742 Neurotrophin 3 Proteins 0.000 description 1
- 102100029268 Neurotrophin-3 Human genes 0.000 description 1
- ZBBHBTPTTSWHBA-UHFFFAOYSA-N Nicardipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN(C)CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ZBBHBTPTTSWHBA-UHFFFAOYSA-N 0.000 description 1
- KUEUWHJGRZKESU-UHFFFAOYSA-N Niceritrol Chemical compound C=1C=CN=CC=1C(=O)OCC(COC(=O)C=1C=NC=CC=1)(COC(=O)C=1C=NC=CC=1)COC(=O)C1=CC=CN=C1 KUEUWHJGRZKESU-UHFFFAOYSA-N 0.000 description 1
- VRAHPESAMYMDQI-UHFFFAOYSA-N Nicomol Chemical compound C1CCC(COC(=O)C=2C=NC=CC=2)(COC(=O)C=2C=NC=CC=2)C(O)C1(COC(=O)C=1C=NC=CC=1)COC(=O)C1=CC=CN=C1 VRAHPESAMYMDQI-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 102000007399 Nuclear hormone receptor Human genes 0.000 description 1
- 108020005497 Nuclear hormone receptor Proteins 0.000 description 1
- BKQNIXIIZIOXLO-UHFFFAOYSA-N O=C(C1=CC=CC=C1)OC(NC1=NC2=CC(C(F)(F)F)=NN2C(Cl)=C1)=O Chemical compound O=C(C1=CC=CC=C1)OC(NC1=NC2=CC(C(F)(F)F)=NN2C(Cl)=C1)=O BKQNIXIIZIOXLO-UHFFFAOYSA-N 0.000 description 1
- 108091034117 Oligonucleotide Proteins 0.000 description 1
- UQGKUQLKSCSZGY-UHFFFAOYSA-N Olmesartan medoxomil Chemical compound C=1C=C(C=2C(=CC=CC=2)C2=NNN=N2)C=CC=1CN1C(CCC)=NC(C(C)(C)O)=C1C(=O)OCC=1OC(=O)OC=1C UQGKUQLKSCSZGY-UHFFFAOYSA-N 0.000 description 1
- 108700020796 Oncogene Proteins 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 229940123973 Oxygen scavenger Drugs 0.000 description 1
- 102000019280 Pancreatic lipases Human genes 0.000 description 1
- 108050006759 Pancreatic lipases Proteins 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 229920002732 Polyanhydride Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920000954 Polyglycolide Polymers 0.000 description 1
- 229920001710 Polyorthoester Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229940127315 Potassium Channel Openers Drugs 0.000 description 1
- TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 description 1
- 102000003923 Protein Kinase C Human genes 0.000 description 1
- 108090000315 Protein Kinase C Proteins 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 1
- AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-N 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
- 108020004511 Recombinant DNA Proteins 0.000 description 1
- RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 108010026951 Short-Acting Insulin Proteins 0.000 description 1
- 229940123958 Short-acting insulin Drugs 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- JLRNKCZRCMIVKA-UHFFFAOYSA-N Simfibrate Chemical compound C=1C=C(Cl)C=CC=1OC(C)(C)C(=O)OCCCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 JLRNKCZRCMIVKA-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229940127504 Somatostatin Receptor Agonists Drugs 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 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
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 102000040945 Transcription factor Human genes 0.000 description 1
- 108091023040 Transcription factor Proteins 0.000 description 1
- 102000004357 Transferases Human genes 0.000 description 1
- 108090000992 Transferases Proteins 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- FZNCGRZWXLXZSZ-CIQUZCHMSA-N Voglibose Chemical compound OCC(CO)N[C@H]1C[C@](O)(CO)[C@@H](O)[C@H](O)[C@H]1O FZNCGRZWXLXZSZ-CIQUZCHMSA-N 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- NYPUYFCKTPRNOR-UHFFFAOYSA-N [3-(5-amino-2-methylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]methanol Chemical compound N12N=C(C)C=C2N=C(N)C=C1C1=CC=CC(CO)=C1 NYPUYFCKTPRNOR-UHFFFAOYSA-N 0.000 description 1
- MNGSRTLAYMOVQR-UHFFFAOYSA-N [3-(5-aminopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]methanol Chemical compound N12N=CC=C2N=C(N)C=C1C1=CC=CC(CO)=C1 MNGSRTLAYMOVQR-UHFFFAOYSA-N 0.000 description 1
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- IENXJNLJEDMNTE-UHFFFAOYSA-N acetic acid;ethane-1,2-diamine Chemical compound CC(O)=O.NCCN IENXJNLJEDMNTE-UHFFFAOYSA-N 0.000 description 1
- 229960001466 acetohexamide Drugs 0.000 description 1
- VGZSUPCWNCWDAN-UHFFFAOYSA-N acetohexamide Chemical compound C1=CC(C(=O)C)=CC=C1S(=O)(=O)NC(=O)NC1CCCCC1 VGZSUPCWNCWDAN-UHFFFAOYSA-N 0.000 description 1
- 239000002535 acidifier Substances 0.000 description 1
- 229940062328 actos Drugs 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 239000003288 aldose reductase inhibitor Substances 0.000 description 1
- 229940090865 aldose reductase inhibitors used in diabetes Drugs 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- AEMOLEFTQBMNLQ-BKBMJHBISA-N alpha-D-galacturonic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-BKBMJHBISA-N 0.000 description 1
- AGBQKNBQESQNJD-UHFFFAOYSA-N alpha-Lipoic acid Natural products OC(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-N 0.000 description 1
- AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 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
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 229960000528 amlodipine Drugs 0.000 description 1
- ZPBWCRDSRKPIDG-UHFFFAOYSA-N amlodipine benzenesulfonate Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl ZPBWCRDSRKPIDG-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 206010002022 amyloidosis Diseases 0.000 description 1
- 239000002333 angiotensin II receptor antagonist Substances 0.000 description 1
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000001458 anti-acid effect Effects 0.000 description 1
- 230000003474 anti-emetic effect Effects 0.000 description 1
- 239000002111 antiemetic agent Substances 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000002830 appetite depressant Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 229960003121 arginine Drugs 0.000 description 1
- 239000008122 artificial sweetener Substances 0.000 description 1
- 235000021311 artificial sweeteners Nutrition 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 150000004646 arylidenes Chemical group 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 229940009098 aspartate Drugs 0.000 description 1
- 229960005370 atorvastatin Drugs 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940050390 benzoate Drugs 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
- QQFYLZXBFWWJHR-UHFFFAOYSA-M benzyl(triethyl)phosphanium;bromide Chemical compound [Br-].CC[P+](CC)(CC)CC1=CC=CC=C1 QQFYLZXBFWWJHR-UHFFFAOYSA-M 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 229960000516 bezafibrate Drugs 0.000 description 1
- IIBYAHWJQTYFKB-UHFFFAOYSA-N bezafibrate Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1CCNC(=O)C1=CC=C(Cl)C=C1 IIBYAHWJQTYFKB-UHFFFAOYSA-N 0.000 description 1
- 150000004283 biguanides Chemical class 0.000 description 1
- 229920000249 biocompatible polymer Polymers 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000008512 biological response Effects 0.000 description 1
- 230000036983 biotransformation Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 229940116229 borneol Drugs 0.000 description 1
- CKDOCTFBFTVPSN-UHFFFAOYSA-N borneol Natural products C1CC2(C)C(C)CC1C2(C)C CKDOCTFBFTVPSN-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- 239000000168 bronchodilator agent Substances 0.000 description 1
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940084891 byetta Drugs 0.000 description 1
- 229960001948 caffeine Drugs 0.000 description 1
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
- 239000000480 calcium channel blocker Substances 0.000 description 1
- 230000001964 calcium overload Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 229960004349 candesartan cilexetil Drugs 0.000 description 1
- 239000003536 cannabinoid receptor antagonist Substances 0.000 description 1
- FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical compound SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 description 1
- 229960000830 captopril Drugs 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 125000004452 carbocyclyl group Chemical group 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000030833 cell death Effects 0.000 description 1
- 230000033026 cell fate determination Effects 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 210000003855 cell nucleus Anatomy 0.000 description 1
- 230000004637 cellular stress Effects 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- MVCQKIKWYUURMU-UHFFFAOYSA-N cetilistat Chemical compound C1=C(C)C=C2C(=O)OC(OCCCCCCCCCCCCCCCC)=NC2=C1 MVCQKIKWYUURMU-UHFFFAOYSA-N 0.000 description 1
- 229950002397 cetilistat Drugs 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- KVSASDOGYIBWTA-UHFFFAOYSA-N chloro benzoate Chemical compound ClOC(=O)C1=CC=CC=C1 KVSASDOGYIBWTA-UHFFFAOYSA-N 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- VDANGULDQQJODZ-UHFFFAOYSA-N chloroprocaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1Cl VDANGULDQQJODZ-UHFFFAOYSA-N 0.000 description 1
- 229960002023 chloroprocaine Drugs 0.000 description 1
- 235000019365 chlortetracycline Nutrition 0.000 description 1
- 229940107137 cholecystokinin Drugs 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 230000001886 ciliary effect Effects 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 229940001468 citrate Drugs 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 229950003072 clinofibrate Drugs 0.000 description 1
- LRXXRIXDSAEIOR-ZDUSSCGKSA-N clobenzorex Chemical compound C([C@H](C)NCC=1C(=CC=CC=1)Cl)C1=CC=CC=C1 LRXXRIXDSAEIOR-ZDUSSCGKSA-N 0.000 description 1
- 229960002492 clobenzorex Drugs 0.000 description 1
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 1
- 229960001214 clofibrate Drugs 0.000 description 1
- 229960002896 clonidine Drugs 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 229960000913 crospovidone Drugs 0.000 description 1
- 239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 description 1
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
- 239000004914 cyclooctane Substances 0.000 description 1
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 description 1
- 239000004913 cyclooctene Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- QQKNSPHAFATFNQ-UHFFFAOYSA-N darglitazone Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1CCC(=O)C(C=C1)=CC=C1CC1SC(=O)NC1=O QQKNSPHAFATFNQ-UHFFFAOYSA-N 0.000 description 1
- WOUOLAUOZXOLJQ-MBSDFSHPSA-N delapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N(CC(O)=O)C1CC2=CC=CC=C2C1)CC1=CC=CC=C1 WOUOLAUOZXOLJQ-MBSDFSHPSA-N 0.000 description 1
- 229960005227 delapril Drugs 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 229960004597 dexfenfluramine Drugs 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229940043237 diethanolamine Drugs 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- FUZBPOHHSBDTJQ-CFOQQKEYSA-L disodium;5-[(2r)-2-[[(2r)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]propyl]-1,3-benzodioxole-2,2-dicarboxylate Chemical compound [Na+].[Na+].C1([C@@H](O)CN[C@@H](CC=2C=C3OC(OC3=CC=2)(C([O-])=O)C([O-])=O)C)=CC=CC(Cl)=C1 FUZBPOHHSBDTJQ-CFOQQKEYSA-L 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- DTGKSKDOIYIVQL-UHFFFAOYSA-N dl-isoborneol Natural products C1CC2(C)C(O)CC1C2(C)C DTGKSKDOIYIVQL-UHFFFAOYSA-N 0.000 description 1
- DLNKOYKMWOXYQA-UHFFFAOYSA-N dl-pseudophenylpropanolamine Natural products CC(N)C(O)C1=CC=CC=C1 DLNKOYKMWOXYQA-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- LXBIFEVIBLOUGU-JGWLITMVSA-N duvoglustat Chemical class OC[C@H]1NC[C@H](O)[C@@H](O)[C@@H]1O LXBIFEVIBLOUGU-JGWLITMVSA-N 0.000 description 1
- 229950000195 edaglitazone Drugs 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 229950005925 eflucimibe Drugs 0.000 description 1
- 229950003102 efonidipine Drugs 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- GBXSMTUPTTWBMN-XIRDDKMYSA-N enalapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 GBXSMTUPTTWBMN-XIRDDKMYSA-N 0.000 description 1
- 229960000873 enalapril Drugs 0.000 description 1
- 231100000284 endotoxic Toxicity 0.000 description 1
- 230000002346 endotoxic effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229950002375 englitazone Drugs 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000002662 enteric coated tablet Substances 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- CHNUOJQWGUIOLD-NFZZJPOKSA-N epalrestat Chemical compound C=1C=CC=CC=1\C=C(/C)\C=C1/SC(=S)N(CC(O)=O)C1=O CHNUOJQWGUIOLD-NFZZJPOKSA-N 0.000 description 1
- 229950010170 epalrestat Drugs 0.000 description 1
- CHNUOJQWGUIOLD-UHFFFAOYSA-N epalrestate Natural products C=1C=CC=CC=1C=C(C)C=C1SC(=S)N(CC(O)=O)C1=O CHNUOJQWGUIOLD-UHFFFAOYSA-N 0.000 description 1
- 229960004563 eprosartan Drugs 0.000 description 1
- OROAFUQRIXKEMV-LDADJPATSA-N eprosartan Chemical compound C=1C=C(C(O)=O)C=CC=1CN1C(CCCC)=NC=C1\C=C(C(O)=O)/CC1=CC=CS1 OROAFUQRIXKEMV-LDADJPATSA-N 0.000 description 1
- AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- ZZCHHVUQYRMYLW-HKBQPEDESA-N farglitazar Chemical compound N([C@@H](CC1=CC=C(C=C1)OCCC=1N=C(OC=1C)C=1C=CC=CC=1)C(O)=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 ZZCHHVUQYRMYLW-HKBQPEDESA-N 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 229960001582 fenfluramine Drugs 0.000 description 1
- 229940125753 fibrate Drugs 0.000 description 1
- WAAPEIZFCHNLKK-PELKAZGASA-N fidarestat Chemical compound C([C@@H](OC1=CC=C(F)C=C11)C(=O)N)[C@@]21NC(=O)NC2=O WAAPEIZFCHNLKK-PELKAZGASA-N 0.000 description 1
- 229950007256 fidarestat Drugs 0.000 description 1
- 239000007941 film coated tablet Substances 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 229960003765 fluvastatin Drugs 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- DSLZVSRJTYRBFB-DUHBMQHGSA-N galactaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O DSLZVSRJTYRBFB-DUHBMQHGSA-N 0.000 description 1
- FODTZLFLDFKIQH-FSVGXZBPSA-N gamma-Oryzanol (TN) Chemical compound C1=C(O)C(OC)=CC(\C=C\C(=O)O[C@@H]2C([C@@H]3CC[C@H]4[C@]5(C)CC[C@@H]([C@@]5(C)CC[C@@]54C[C@@]53CC2)[C@H](C)CCC=C(C)C)(C)C)=C1 FODTZLFLDFKIQH-FSVGXZBPSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 229960005219 gentisic acid Drugs 0.000 description 1
- GNKDKYIHGQKHHM-RJKLHVOGSA-N ghrelin Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)CN)COC(=O)CCCCCCC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1N=CNC=1)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C1=CC=CC=C1 GNKDKYIHGQKHHM-RJKLHVOGSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- ZKUDBRCEOBOWLF-UHFFFAOYSA-N glisoxepide Chemical compound O1C(C)=CC(C(=O)NCCC=2C=CC(=CC=2)S(=O)(=O)NC(=O)NN2CCCCCC2)=N1 ZKUDBRCEOBOWLF-UHFFFAOYSA-N 0.000 description 1
- 229960003236 glisoxepide Drugs 0.000 description 1
- 229940124828 glucokinase activator Drugs 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 239000000174 gluconic acid Chemical group 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 229940095884 glucophage Drugs 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- 230000009229 glucose formation Effects 0.000 description 1
- 239000004220 glutamic acid Chemical group 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 229960005150 glycerol Drugs 0.000 description 1
- NFRPNQDSKJJQGV-UHFFFAOYSA-N glyhexamide Chemical compound C=1C=C2CCCC2=CC=1S(=O)(=O)NC(=O)NC1CCCCC1 NFRPNQDSKJJQGV-UHFFFAOYSA-N 0.000 description 1
- 229950008290 glyhexamide Drugs 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 210000002216 heart Anatomy 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
- 125000005553 heteroaryloxy group Chemical group 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 1
- 208000006575 hypertriglyceridemia Diseases 0.000 description 1
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 description 1
- INSWZAQOISIYDT-UHFFFAOYSA-N imidazo[1,2-a]pyrimidine Chemical compound C1=CC=NC2=NC=CN21 INSWZAQOISIYDT-UHFFFAOYSA-N 0.000 description 1
- PQWQQQGKMHENOC-UHFFFAOYSA-N imidazo[1,2-c]pyrimidine Chemical compound C1=NC=CC2=NC=CN21 PQWQQQGKMHENOC-UHFFFAOYSA-N 0.000 description 1
- JMANUKZDKDKBJP-UHFFFAOYSA-N imidazo[1,5-a]pyridine Chemical compound C1=CC=CC2=CN=CN21 JMANUKZDKDKBJP-UHFFFAOYSA-N 0.000 description 1
- LXYHLTOJFGNEKG-UHFFFAOYSA-N imidazo[1,5-a]pyrimidine Chemical compound C1=CC=NC2=CN=CN21 LXYHLTOJFGNEKG-UHFFFAOYSA-N 0.000 description 1
- AGYYYBIAZFILKT-UHFFFAOYSA-N imidazo[1,5-c]pyrimidine Chemical compound C1=NC=CC2=CN=CN21 AGYYYBIAZFILKT-UHFFFAOYSA-N 0.000 description 1
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 description 1
- 125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- MGXWVYUBJRZYPE-YUGYIWNOSA-N incretin Chemical class C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCC(N)=O)C(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1C=CC(O)=CC=1)[C@@H](C)O)[C@@H](C)CC)C1=CC=C(O)C=C1 MGXWVYUBJRZYPE-YUGYIWNOSA-N 0.000 description 1
- 239000000859 incretin Substances 0.000 description 1
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- PBGKTOXHQIOBKM-FHFVDXKLSA-N insulin (human) 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=3NC=NC=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](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C=CC=CC=1)C(C)C)C1=CN=CN1 PBGKTOXHQIOBKM-FHFVDXKLSA-N 0.000 description 1
- 230000004155 insulin signaling pathway Effects 0.000 description 1
- 230000031146 intracellular signal transduction Effects 0.000 description 1
- 238000007913 intrathecal administration Methods 0.000 description 1
- BVJUXXYBIMHHDW-UHFFFAOYSA-N iodane Chemical compound I.I BVJUXXYBIMHHDW-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229960002198 irbesartan Drugs 0.000 description 1
- YCPOHTHPUREGFM-UHFFFAOYSA-N irbesartan Chemical compound O=C1N(CC=2C=CC(=CC=2)C=2C(=CC=CC=2)C=2[N]N=NN=2)C(CCCC)=NC21CCCC2 YCPOHTHPUREGFM-UHFFFAOYSA-N 0.000 description 1
- 229940045996 isethionic acid Drugs 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- 230000000155 isotopic effect Effects 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 238000011813 knockout mouse model Methods 0.000 description 1
- 229940001447 lactate Drugs 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 150000003903 lactic acid esters Chemical class 0.000 description 1
- 229940099584 lactobionate Drugs 0.000 description 1
- JYTUSYBCFIZPBE-AMTLMPIISA-N lactobionic acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O JYTUSYBCFIZPBE-AMTLMPIISA-N 0.000 description 1
- 201000010901 lateral sclerosis Diseases 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 description 1
- 229940039781 leptin Drugs 0.000 description 1
- 229960004194 lidocaine Drugs 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 235000019136 lipoic acid Nutrition 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 208000007903 liver failure Diseases 0.000 description 1
- 231100000835 liver failure Toxicity 0.000 description 1
- 229960004773 losartan Drugs 0.000 description 1
- KJJZZJSZUJXYEA-UHFFFAOYSA-N losartan Chemical compound CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C=2[N]N=NN=2)C=C1 KJJZZJSZUJXYEA-UHFFFAOYSA-N 0.000 description 1
- 229960004844 lovastatin Drugs 0.000 description 1
- PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 description 1
- QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 description 1
- 239000008176 lyophilized powder Substances 0.000 description 1
- 229960003646 lysine Drugs 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 229960001708 magnesium carbonate Drugs 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 210000004962 mammalian cell Anatomy 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- ANEBWFXPVPTEET-UHFFFAOYSA-N manidipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN2CCN(CC2)C(C=2C=CC=CC=2)C=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ANEBWFXPVPTEET-UHFFFAOYSA-N 0.000 description 1
- 229960003963 manidipine Drugs 0.000 description 1
- FYGDTMLNYKFZSV-UHFFFAOYSA-N mannotriose Natural products OC1C(O)C(O)C(CO)OC1OC1C(CO)OC(OC2C(OC(O)C(O)C2O)CO)C(O)C1O FYGDTMLNYKFZSV-UHFFFAOYSA-N 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 229960000299 mazindol Drugs 0.000 description 1
- 229960003194 meglumine Drugs 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 125000005341 metaphosphate group Chemical group 0.000 description 1
- OETHQSJEHLVLGH-UHFFFAOYSA-N metformin hydrochloride Chemical compound Cl.CN(C)C(=N)N=C(N)N OETHQSJEHLVLGH-UHFFFAOYSA-N 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
- FWMHZWMPUWAUPL-NDEPHWFRSA-N methyl (4s)-3-[3-[4-(3-acetamidophenyl)piperidin-1-yl]propylcarbamoyl]-4-(3,4-difluorophenyl)-6-(methoxymethyl)-2-oxo-1,4-dihydropyrimidine-5-carboxylate Chemical compound N1([C@H](C(=C(NC1=O)COC)C(=O)OC)C=1C=C(F)C(F)=CC=1)C(=O)NCCCN(CC1)CCC1C1=CC=CC(NC(C)=O)=C1 FWMHZWMPUWAUPL-NDEPHWFRSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 229920000609 methyl cellulose Polymers 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
- 229960001047 methyl salicylate Drugs 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 229960003404 mexiletine Drugs 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 210000003470 mitochondria Anatomy 0.000 description 1
- 230000002438 mitochondrial effect Effects 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 208000005264 motor neuron disease Diseases 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- 229950001135 muraglitazar Drugs 0.000 description 1
- 230000020763 muscle atrophy Effects 0.000 description 1
- 201000000585 muscular atrophy Diseases 0.000 description 1
- ODPQHUSFLNJHTE-UHFFFAOYSA-N n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)-2,2-diphenylacetamide Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)C(=O)NC(=NC1=CC=NN11)C=C1N1CCOCC1 ODPQHUSFLNJHTE-UHFFFAOYSA-N 0.000 description 1
- ANHRAERHKBURGU-UHFFFAOYSA-N n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)-2-phenoxyacetamide Chemical compound C1=C(N2CCOCC2)N2N=CC=C2N=C1NC(=O)COC1=CC=CC=C1 ANHRAERHKBURGU-UHFFFAOYSA-N 0.000 description 1
- UUGWWIWVDPLPDR-UHFFFAOYSA-N n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)-3-phenylpropanamide Chemical compound C1=C(N2CCOCC2)N2N=CC=C2N=C1NC(=O)CCC1=CC=CC=C1 UUGWWIWVDPLPDR-UHFFFAOYSA-N 0.000 description 1
- SPPIUFAMJAKYEK-UHFFFAOYSA-N n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)-4-oxopentanamide Chemical compound N12N=CC=C2N=C(NC(=O)CCC(=O)C)C=C1N1CCOCC1 SPPIUFAMJAKYEK-UHFFFAOYSA-N 0.000 description 1
- WQUFXMPFBACIHI-UHFFFAOYSA-N n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)heptanamide Chemical compound N12N=CC=C2N=C(NC(=O)CCCCCC)C=C1N1CCOCC1 WQUFXMPFBACIHI-UHFFFAOYSA-N 0.000 description 1
- LLIGESDIWPCIMY-UHFFFAOYSA-N n-(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)hex-5-enamide Chemical compound N12N=CC=C2N=C(NC(=O)CCCC=C)C=C1N1CCOCC1 LLIGESDIWPCIMY-UHFFFAOYSA-N 0.000 description 1
- VGPBPWRBXBKGRE-UHFFFAOYSA-N n-(oxomethylidene)hydroxylamine Chemical compound ON=C=O VGPBPWRBXBKGRE-UHFFFAOYSA-N 0.000 description 1
- XECDNMLGEUMMCP-UHFFFAOYSA-N n-[2-[(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)amino]-2-oxoethyl]benzamide Chemical compound C1=C(N2CCOCC2)N2N=CC=C2N=C1NC(=O)CNC(=O)C1=CC=CC=C1 XECDNMLGEUMMCP-UHFFFAOYSA-N 0.000 description 1
- OQTNNEJILVYISQ-UHFFFAOYSA-N n-[3-[(7-morpholin-4-ylpyrazolo[1,5-a]pyrimidin-5-yl)amino]-3-oxopropyl]benzamide Chemical compound C1=C(N2CCOCC2)N2N=CC=C2N=C1NC(=O)CCNC(=O)C1=CC=CC=C1 OQTNNEJILVYISQ-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- JAIIZWCZERLWEK-UHFFFAOYSA-N n-[4-[2-(diethylamino)ethoxy]-3-methoxyphenyl]-n-methyl-4-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=C(OC)C(OCCN(CC)CC)=CC=C1N(C)C(=O)C1=CC=C(C=2C=CC(=CC=2)C(F)(F)F)C=C1 JAIIZWCZERLWEK-UHFFFAOYSA-N 0.000 description 1
- ROJMRKGMGPXJJZ-UHFFFAOYSA-N n-[5-(5-aminopyrazolo[1,5-a]pyrimidin-7-yl)pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC=C1C1=CC(N)=NC2=CC=NN12 ROJMRKGMGPXJJZ-UHFFFAOYSA-N 0.000 description 1
- OVOMHNSKJAVDTG-UHFFFAOYSA-N n-[7-(4-hydroxypiperidin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=CC(C(C)(O)C)=CC=C1C(=O)NC1=NC2=CC=NN2C(N2CCC(O)CC2)=C1 OVOMHNSKJAVDTG-UHFFFAOYSA-N 0.000 description 1
- YUIHSJPQWUJXRG-KRWDZBQOSA-N n-[7-[(3s)-3-(dimethylamino)pyrrolidin-1-yl]pyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1[C@@H](N(C)C)CCN1C1=CC(NC(=O)C=2C=CC(=CC=2)C(C)(C)O)=NC2=CC=NN12 YUIHSJPQWUJXRG-KRWDZBQOSA-N 0.000 description 1
- BHDYIUXAVFNTTA-UHFFFAOYSA-N n-[7-[4-(2-hydroxyethyl)piperidin-1-yl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(N2CCC(CCO)CC2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 BHDYIUXAVFNTTA-UHFFFAOYSA-N 0.000 description 1
- WURDOVBEVHXNIQ-UHFFFAOYSA-N n-[7-[4-(benzenesulfonyl)piperazin-1-yl]-2-methylpyrazolo[1,5-a]pyrimidin-5-yl]-4-(2-hydroxypropan-2-yl)benzamide Chemical compound C1=C(N2CCN(CC2)S(=O)(=O)C=2C=CC=CC=2)N2N=C(C)C=C2N=C1NC(=O)C1=CC=C(C(C)(C)O)C=C1 WURDOVBEVHXNIQ-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 229920001206 natural gum Polymers 0.000 description 1
- 239000003900 neurotrophic factor Substances 0.000 description 1
- 230000032064 neurotrophin production Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229960001783 nicardipine Drugs 0.000 description 1
- 229960000827 niceritrol Drugs 0.000 description 1
- 229950001071 nicomol Drugs 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 1
- 229960001597 nifedipine Drugs 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- ZHCAAFJSYLFLPX-UHFFFAOYSA-N nitrocyclohexatriene Chemical group [O-][N+](=O)C1=CC=C=C[CH]1 ZHCAAFJSYLFLPX-UHFFFAOYSA-N 0.000 description 1
- 150000002829 nitrogen Chemical group 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000000346 nonvolatile oil Substances 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- URPYMXQQVHTUDU-OFGSCBOVSA-N nucleopeptide y Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(N)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 URPYMXQQVHTUDU-OFGSCBOVSA-N 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 210000004940 nucleus Anatomy 0.000 description 1
- 235000003170 nutritional factors Nutrition 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 1
- 229960001199 olmesartan medoxomil Drugs 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229940125395 oral insulin Drugs 0.000 description 1
- 239000007935 oral tablet Substances 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 1
- 229960001243 orlistat Drugs 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 150000003901 oxalic acid esters Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000006179 pH buffering agent Substances 0.000 description 1
- 229940116369 pancreatic lipase Drugs 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Chemical group OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 235000019371 penicillin G benzathine Nutrition 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229960003562 phentermine Drugs 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- DLNKOYKMWOXYQA-APPZFPTMSA-N phenylpropanolamine Chemical compound C[C@@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-APPZFPTMSA-N 0.000 description 1
- 229960000395 phenylpropanolamine Drugs 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229960002797 pitavastatin Drugs 0.000 description 1
- VGYFMXBACGZSIL-MCBHFWOFSA-N pitavastatin Chemical compound OC(=O)C[C@H](O)C[C@H](O)\C=C\C1=C(C2CC2)N=C2C=CC=CC2=C1C1=CC=C(F)C=C1 VGYFMXBACGZSIL-MCBHFWOFSA-N 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 description 1
- 235000002378 plant sterols Nutrition 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920000747 poly(lactic acid) Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229940057838 polyethylene glycol 4000 Drugs 0.000 description 1
- 239000004633 polyglycolic acid Substances 0.000 description 1
- 239000004626 polylactic acid Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
- 229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000000291 postprandial effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- WSHYKIAQCMIPTB-UHFFFAOYSA-M potassium;2-oxo-3-(3-oxo-1-phenylbutyl)chromen-4-olate Chemical compound [K+].[O-]C=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 WSHYKIAQCMIPTB-UHFFFAOYSA-M 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 229960003611 pramlintide Drugs 0.000 description 1
- 108010029667 pramlintide Proteins 0.000 description 1
- NRKVKVQDUCJPIZ-MKAGXXMWSA-N pramlintide acetate Chemical compound C([C@@H](C(=O)NCC(=O)N1CCC[C@H]1C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CS)NC(=O)[C@@H](N)CCCCN)[C@@H](C)O)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 NRKVKVQDUCJPIZ-MKAGXXMWSA-N 0.000 description 1
- 229960002965 pravastatin Drugs 0.000 description 1
- TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- FYPMFJGVHOHGLL-UHFFFAOYSA-N probucol Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1SC(C)(C)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FYPMFJGVHOHGLL-UHFFFAOYSA-N 0.000 description 1
- 229960003912 probucol Drugs 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 150000003151 propanoic acid esters Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229940093625 propylene glycol monostearate Drugs 0.000 description 1
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 230000004952 protein activity Effects 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- VUVGMQNYJPPCCC-UHFFFAOYSA-N pyrido[1,2-a]indole Chemical compound C1=CC=CC2=CC3=CC=CC=C3N21 VUVGMQNYJPPCCC-UHFFFAOYSA-N 0.000 description 1
- 125000005494 pyridonyl group Chemical group 0.000 description 1
- 235000008151 pyridoxamine Nutrition 0.000 description 1
- 239000011699 pyridoxamine Substances 0.000 description 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
- JBDKAABFESSFMV-UHFFFAOYSA-N pyrrolo[1,2-a]pyrimidine Chemical compound N1=CC=CN2C=CC=C21 JBDKAABFESSFMV-UHFFFAOYSA-N 0.000 description 1
- NISJKLIMPQPAQS-UHFFFAOYSA-N pyrrolo[1,2-b]pyridazine Chemical compound C1=CC=NN2C=CC=C21 NISJKLIMPQPAQS-UHFFFAOYSA-N 0.000 description 1
- RIEKLTCRUGDAPM-UHFFFAOYSA-N pyrrolo[1,2-c]pyrimidine Chemical compound C1=CN=CN2C=CC=C21 RIEKLTCRUGDAPM-UHFFFAOYSA-N 0.000 description 1
- WMHRXFNTQPIYDT-UHFFFAOYSA-N pyrrolo[2,3-b]pyrazine Chemical compound C1=C[N]C2=NC=CC2=N1 WMHRXFNTQPIYDT-UHFFFAOYSA-N 0.000 description 1
- 229940076788 pyruvate Drugs 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 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
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 229950004123 ranirestat Drugs 0.000 description 1
- 229940044601 receptor agonist Drugs 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000022983 regulation of cell cycle Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 108091092562 ribozyme Proteins 0.000 description 1
- JZCPYUJPEARBJL-UHFFFAOYSA-N rimonabant Chemical compound CC=1C(C(=O)NN2CCCCC2)=NN(C=2C(=CC(Cl)=CC=2)Cl)C=1C1=CC=C(Cl)C=C1 JZCPYUJPEARBJL-UHFFFAOYSA-N 0.000 description 1
- CRPGRUONUFDYBG-UHFFFAOYSA-N risarestat Chemical compound C1=C(OCC)C(OCCCCC)=CC=C1C1C(=O)NC(=O)S1 CRPGRUONUFDYBG-UHFFFAOYSA-N 0.000 description 1
- XMSXOLDPMGMWTH-UHFFFAOYSA-N rivoglitazone Chemical compound CN1C2=CC(OC)=CC=C2N=C1COC(C=C1)=CC=C1CC1SC(=O)NC1=O XMSXOLDPMGMWTH-UHFFFAOYSA-N 0.000 description 1
- BPRHUIZQVSMCRT-VEUZHWNKSA-N rosuvastatin Chemical compound CC(C)C1=NC(N(C)S(C)(=O)=O)=NC(C=2C=CC(F)=CC=2)=C1\C=C\[C@@H](O)C[C@@H](O)CC(O)=O BPRHUIZQVSMCRT-VEUZHWNKSA-N 0.000 description 1
- 229960000672 rosuvastatin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 239000000523 sample Substances 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
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000000580 secretagogue effect Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 235000019615 sensations Nutrition 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000011450 sequencing therapy Methods 0.000 description 1
- 150000003354 serine derivatives Chemical class 0.000 description 1
- 229960004425 sibutramine Drugs 0.000 description 1
- UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 description 1
- 229960004058 simfibrate Drugs 0.000 description 1
- 229960002855 simvastatin Drugs 0.000 description 1
- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 1
- IZTQOLKUZKXIRV-YRVFCXMDSA-N sincalide Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](N)CC(O)=O)C1=CC=C(OS(O)(=O)=O)C=C1 IZTQOLKUZKXIRV-YRVFCXMDSA-N 0.000 description 1
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229960003885 sodium benzoate Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 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
- 229960001462 sodium cyclamate Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- DCQXTYAFFMSNNH-UHFFFAOYSA-M sodium;2-[bis(2-hydroxyethyl)amino]ethanol;acetate Chemical compound [Na+].CC([O-])=O.OCCN(CCO)CCO DCQXTYAFFMSNNH-UHFFFAOYSA-M 0.000 description 1
- RCOSUMRTSQULBK-UHFFFAOYSA-N sodium;propan-1-olate Chemical compound [Na+].CCC[O-] RCOSUMRTSQULBK-UHFFFAOYSA-N 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 229940033331 soy sterol Drugs 0.000 description 1
- 239000004059 squalene synthase inhibitor Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003900 succinic acid esters Chemical class 0.000 description 1
- 125000001010 sulfinic acid amide group Chemical group 0.000 description 1
- 150000003455 sulfinic acids Chemical class 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003899 tartaric acid esters Chemical class 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229960000651 tasosartan Drugs 0.000 description 1
- ADXGNEYLLLSOAR-UHFFFAOYSA-N tasosartan Chemical compound C12=NC(C)=NC(C)=C2CCC(=O)N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 ADXGNEYLLLSOAR-UHFFFAOYSA-N 0.000 description 1
- 229960005187 telmisartan Drugs 0.000 description 1
- RKSOPLXZQNSWAS-UHFFFAOYSA-N tert-butyl bromide Chemical compound CC(C)(C)Br RKSOPLXZQNSWAS-UHFFFAOYSA-N 0.000 description 1
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 229960004559 theobromine Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- SMZMHUCIDGHERP-UHFFFAOYSA-N thieno[2,3-b]pyridine Chemical compound C1=CN=C2SC=CC2=C1 SMZMHUCIDGHERP-UHFFFAOYSA-N 0.000 description 1
- GDQBPBMIAFIRIU-UHFFFAOYSA-N thieno[2,3-c]pyridine Chemical compound C1=NC=C2SC=CC2=C1 GDQBPBMIAFIRIU-UHFFFAOYSA-N 0.000 description 1
- DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical compound C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 description 1
- 125000005297 thienyloxy group Chemical group S1C(=CC=C1)O* 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 150000003556 thioamides Chemical class 0.000 description 1
- 229960002663 thioctic acid Drugs 0.000 description 1
- 125000005323 thioketone group Chemical group 0.000 description 1
- 125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 description 1
- 229940094937 thioredoxin Drugs 0.000 description 1
- 230000030968 tissue homeostasis Effects 0.000 description 1
- LUBHDINQXIHVLS-UHFFFAOYSA-N tolrestat Chemical compound OC(=O)CN(C)C(=S)C1=CC=CC2=C(C(F)(F)F)C(OC)=CC=C21 LUBHDINQXIHVLS-UHFFFAOYSA-N 0.000 description 1
- 229960003069 tolrestat Drugs 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- LENLQGBLVGGAMF-UHFFFAOYSA-N tributyl([1,2,4]triazolo[1,5-a]pyridin-6-yl)stannane Chemical compound C1=C([Sn](CCCC)(CCCC)CCCC)C=CC2=NC=NN21 LENLQGBLVGGAMF-UHFFFAOYSA-N 0.000 description 1
- 229940117013 triethanolamine oleate Drugs 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 229960001729 voglibose Drugs 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- SXONDGSPUVNZLO-UHFFFAOYSA-N zenarestat Chemical compound O=C1N(CC(=O)O)C2=CC(Cl)=CC=C2C(=O)N1CC1=CC=C(Br)C=C1F SXONDGSPUVNZLO-UHFFFAOYSA-N 0.000 description 1
- 229950006343 zenarestat Drugs 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229950005346 zopolrestat Drugs 0.000 description 1
- FYGDTMLNYKFZSV-BYLHFPJWSA-N β-1,4-galactotrioside 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]2[C@@H](O[C@@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-BYLHFPJWSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic 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
-
- 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
-
- 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
-
- 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
- A61P13/06—Anti-spasmodics
-
- 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
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- 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
- A61P17/04—Antipruritics
-
- 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
- A61P17/06—Antipsoriatics
-
- 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
-
- 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
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- 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
- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
-
- 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
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
-
- 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
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Biomedical Technology (AREA)
- Physical Education & Sports Medicine (AREA)
- Neurosurgery (AREA)
- Immunology (AREA)
- Hematology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Obesity (AREA)
- Dermatology (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Endocrinology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Vascular Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Gastroenterology & Hepatology (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4116608P | 2008-03-31 | 2008-03-31 | |
| US61/041,166 | 2008-03-31 | ||
| PCT/US2009/038840 WO2009123986A1 (en) | 2008-03-31 | 2009-03-30 | Apoptosis signal-regulating kinase 1 inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011517458A JP2011517458A (ja) | 2011-06-09 |
| JP2011517458A5 JP2011517458A5 (cg-RX-API-DMAC7.html) | 2012-05-24 |
| JP5432982B2 true JP5432982B2 (ja) | 2014-03-05 |
Family
ID=40750935
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011503082A Expired - Fee Related JP5432982B2 (ja) | 2008-03-31 | 2009-03-30 | アポトーシスシグナル調節キナーゼ１阻害剤 |
Country Status (4)
| Country | Link |
|---|---|
| US (2) | US8461163B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2271646A1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP5432982B2 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2009123986A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (60)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2416660B1 (en) * | 2009-04-07 | 2014-07-02 | Infinity Pharmaceuticals, Inc. | Inhibitors of fatty acid amide hydrolase |
| TWI491606B (zh) | 2009-07-13 | 2015-07-11 | Gilead Sciences Inc | 調節細胞凋亡信號之激酶的抑制劑 |
| WO2011041293A1 (en) * | 2009-09-30 | 2011-04-07 | Takeda Pharmaceutical Company Limited | Pyrazolo [1, 5-a] pyrimidine derivatives as apoptosis signal-regulating kinase 1 inhibitors |
| US8802695B2 (en) * | 2010-02-03 | 2014-08-12 | Takeda Pharmaceutical Company Limited | Apoptosis signal-regulating kinase 1 inhibitors |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| WO2012003387A1 (en) | 2010-07-02 | 2012-01-05 | Gilead Sciences, Inc. | Apoptosis signal-regulating kinase inhibitors |
| JP5525612B2 (ja) * | 2010-07-23 | 2014-06-18 | 国立大学法人 東京大学 | 含窒素複素環誘導体 |
| JP5927201B2 (ja) * | 2010-12-16 | 2016-06-01 | カルチャン リミテッド | Ａｓｋ１阻害ピロロピリミジン誘導体 |
| EP2734520B1 (en) | 2011-07-19 | 2016-09-14 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| EP2567959B1 (en) | 2011-09-12 | 2014-04-16 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| CA2858096C (en) * | 2011-12-22 | 2020-06-23 | Gilead Sciences, Inc. | Pyrazolo[1,5-a]pyrimidines as antiviral agents |
| UY34573A (es) | 2012-01-27 | 2013-06-28 | Gilead Sciences Inc | Inhibidor de la quinasa que regula la señal de la apoptosis |
| US9745320B2 (en) * | 2013-01-18 | 2017-08-29 | Guangzhou Maxinovel Pharmaceuticals Co., Ltd. | Five-and-six-membered heterocyclic compound, and preparation method, pharmaceutical composition and use thereof |
| EP3019172B1 (en) * | 2013-07-11 | 2019-09-25 | Evestra, Inc. | Pro-drug forming compounds |
| GB201410817D0 (en) * | 2014-06-17 | 2014-07-30 | Ucb Biopharma Sprl And Katholieke Universiteit Leuven K U Leuven R & D | Therapeutic agents |
| TW201618781A (zh) | 2014-08-13 | 2016-06-01 | 吉李德科學股份有限公司 | 治療肺高血壓之方法 |
| WO2016049069A1 (en) | 2014-09-24 | 2016-03-31 | Gilead Sciences, Inc. | Methods of treating liver disease |
| EP4276095A3 (en) | 2014-12-23 | 2024-01-17 | Gilead Sciences, Inc. | Processes for preparing ask1 inhibitors |
| MA41252A (fr) | 2014-12-23 | 2017-10-31 | Gilead Sciences Inc | Formes solides d'un inhibiteur d'ask 1 |
| CN105906621A (zh) * | 2015-04-06 | 2016-08-31 | 四川百利药业有限责任公司 | 用作fgfr抑制剂的乙醇类化合物 |
| TW201718581A (zh) | 2015-10-19 | 2017-06-01 | 英塞特公司 | 作為免疫調節劑之雜環化合物 |
| CA3005727A1 (en) | 2015-11-19 | 2017-05-26 | Incyte Corporation | Substituted 2-methylbiphenyl-3-yl heterocyclic compounds and pharmaceutical compositions thereof useful as immunomodulators |
| CR20180374A (es) | 2015-12-22 | 2018-10-16 | Incyte Corp | Compuestos heterocíclicos como inmunomoduladores |
| MA44860A (fr) | 2016-05-06 | 2019-03-13 | Incyte Holdings Corp | Composés hétérocycliques utilisés comme immunomodulateurs |
| US20170342060A1 (en) | 2016-05-26 | 2017-11-30 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| CA3028685A1 (en) | 2016-06-20 | 2017-12-28 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| WO2018013789A1 (en) | 2016-07-14 | 2018-01-18 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| ES2941716T3 (es) | 2016-08-29 | 2023-05-25 | Incyte Corp | Compuestos heterocíclicos como inmunomoduladores |
| JOP20190144A1 (ar) * | 2016-12-16 | 2019-06-16 | Janssen Pharmaceutica Nv | إيميدازو بيرولو بيريدين كمثبطات لعائلة jak الخاصة بإنزيمات الكيناز |
| JP7303108B2 (ja) | 2016-12-22 | 2023-07-04 | インサイト・コーポレイション | 免疫調節剤としての二環式複素芳香環化合物 |
| US20180179201A1 (en) | 2016-12-22 | 2018-06-28 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| ES2899402T3 (es) | 2016-12-22 | 2022-03-11 | Incyte Corp | Derivados de piridina como inmunomoduladores |
| CR20190318A (es) | 2016-12-22 | 2019-10-21 | Incyte Corp | Compuestos heterocíclicos como inmunomoduladores |
| SG10202106743QA (en) | 2016-12-22 | 2021-08-30 | Incyte Corp | Tetrahydro imidazo[4,5-c]pyridine derivatives as pd-l1 internalization inducers |
| HU231057B1 (hu) * | 2017-03-13 | 2020-04-28 | Richter Gedeon Nyrt | Gyógyászatilag hatékony aril-szubsztituált pirazolo[1,5-a]pirimidin származékok |
| HU231058B1 (hu) * | 2017-03-13 | 2020-04-28 | Richter Gedeon Nyrt. | Gyógyászatilag hatékony aliciklusos-szubsztituált pirazolo[1,5-a]pirimidin származékok |
| PL3621615T3 (pl) | 2017-05-12 | 2024-03-25 | Enanta Pharmaceuticals, Inc. | Inhibitory regulujące sygnał apoptozy kinazy 1 i sposoby ich stosowania |
| WO2018218051A1 (en) | 2017-05-25 | 2018-11-29 | Enanta Pharmaceuticals, Inc. | Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| WO2018218044A2 (en) | 2017-05-25 | 2018-11-29 | Enanta Pharmaceuticals Inc | Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| WO2018218042A1 (en) | 2017-05-25 | 2018-11-29 | Enanta Pharmaceuticals, Inc. | Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| GB201711234D0 (en) | 2017-07-12 | 2017-08-23 | Galapagos Nv | Pyrrolopyrimidine and pyrrolopyridine derivatives |
| WO2019046186A1 (en) | 2017-08-28 | 2019-03-07 | Enanta Pharmaceuticals, Inc. | INHIBITORS OF KINASE 1 REGULATING THE APOPTOTIC SIGNAL CONTAINING TETRAZOLES AND METHODS OF USE THEREOF |
| EP4212529B1 (en) | 2018-03-30 | 2025-01-29 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| WO2019213244A1 (en) | 2018-05-02 | 2019-11-07 | Enanta Pharmaceuticals, Inc. | Tetrazole containing apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| US10683289B2 (en) | 2018-05-02 | 2020-06-16 | Enanta Pharmaceuticals, Inc. | Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| EP4520328A3 (en) | 2018-05-11 | 2025-04-16 | Incyte Corporation | Heterocyclic compounds as immunomodulators |
| JP2021534152A (ja) * | 2018-08-14 | 2021-12-09 | バイオジェン・エムエイ・インコーポレイテッドBiogen MA Inc. | Ａｓｋ１阻害剤 |
| WO2020041417A1 (en) | 2018-08-22 | 2020-02-27 | Enanta Pharmaceuticals, Inc. | Cycloalkyl-containing apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| US11345699B2 (en) | 2018-11-19 | 2022-05-31 | Enanta Pharmaceuticals, Inc. | Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| WO2020198214A1 (en) | 2019-03-25 | 2020-10-01 | Enanta Pharmaceuticals, Inc. | Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| WO2021030162A1 (en) | 2019-08-09 | 2021-02-18 | Incyte Corporation | Salts of a pd-1/pd-l1 inhibitor |
| CR20220190A (es) | 2019-09-30 | 2022-06-15 | Incyte Corp | Compuestos de pirido [3,2-d] primidina como inmunomoduladores |
| EP4058461A1 (en) | 2019-11-11 | 2022-09-21 | Incyte Corporation | Salts and crystalline forms of a pd-1/pd-l1 inhibitor |
| WO2022020891A1 (en) * | 2020-07-27 | 2022-02-03 | Esfam Biotech Pty Ltd | Methods of prophylaxis and treatment of corona virus |
| WO2022020889A1 (en) * | 2020-07-27 | 2022-02-03 | Esfam Biotech Pty Ltd | Method of treatment of cytomegalovirus |
| EP4188933A4 (en) * | 2020-07-27 | 2024-09-04 | Esfam Biotech Pty Ltd. | COMPOUNDS |
| WO2022099018A1 (en) | 2020-11-06 | 2022-05-12 | Incyte Corporation | Process of preparing a pd-1/pd-l1 inhibitor |
| PE20231438A1 (es) | 2020-11-06 | 2023-09-14 | Incyte Corp | Proceso para hacer un inhibidor de pd-1/pd-l1 y sales y formas cristalinas del mismo |
| US11760756B2 (en) | 2020-11-06 | 2023-09-19 | Incyte Corporation | Crystalline form of a PD-1/PD-L1 inhibitor |
| CA3213134A1 (en) | 2021-03-11 | 2022-09-15 | Janssen Pharmaceutica Nv | Lorpucitinib for use in the treatment of jak mediated disorders |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7196078B2 (en) | 2002-09-04 | 2007-03-27 | Schering Corpoartion | Trisubstituted and tetrasubstituted pyrazolopyrimidines as cyclin dependent kinase inhibitors |
| MXPA05008955A (es) * | 2003-02-28 | 2006-02-22 | Teijin Pharma Ltd | Derivados de pirazolo [1,5-a] pirimidina. |
| GB0305559D0 (en) * | 2003-03-11 | 2003-04-16 | Teijin Ltd | Compounds |
| EP1608652A1 (en) * | 2003-03-31 | 2005-12-28 | Vernalis (Cambridge) Limited | Pyrazolopyrimidine compounds and their use in medicine |
| EP1666468A4 (en) | 2003-09-09 | 2007-03-21 | Ono Pharmaceutical Co | CRF ANTAGONISTS AND HETEROBICYCLIC COMPOUNDS |
| US20070060595A1 (en) | 2003-10-10 | 2007-03-15 | Toshio Yoshizawa | Novel fused heterocyclic compound and use thereof |
| WO2007013673A1 (en) | 2005-07-29 | 2007-02-01 | Astellas Pharma Inc. | Fused heterocycles as lck inhibitors |
| JPWO2008016131A1 (ja) * | 2006-08-04 | 2009-12-24 | 武田薬品工業株式会社 | 縮合複素環化合物 |
| WO2008063671A2 (en) | 2006-11-20 | 2008-05-29 | Alantos Pharmaceuticals Holding, Inc. | Heterobicyclic metalloprotease inhibitors |
| MX2009009540A (es) | 2007-03-07 | 2009-09-16 | Alantos Pharm Holding | Inhibidores de metaloproteasa que contienen una porcion heterociclica. |
-
2009
- 2009-03-30 US US12/935,542 patent/US8461163B2/en not_active Expired - Fee Related
- 2009-03-30 JP JP2011503082A patent/JP5432982B2/ja not_active Expired - Fee Related
- 2009-03-30 WO PCT/US2009/038840 patent/WO2009123986A1/en not_active Ceased
- 2009-03-30 EP EP09728425A patent/EP2271646A1/en not_active Withdrawn
-
2013
- 2013-03-28 US US13/852,924 patent/US8921358B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2011517458A (ja) | 2011-06-09 |
| US20130203731A1 (en) | 2013-08-08 |
| WO2009123986A1 (en) | 2009-10-08 |
| US8461163B2 (en) | 2013-06-11 |
| US20110077235A1 (en) | 2011-03-31 |
| US8921358B2 (en) | 2014-12-30 |
| EP2271646A1 (en) | 2011-01-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5432982B2 (ja) | アポトーシスシグナル調節キナーゼ１阻害剤 | |
| JP5711270B2 (ja) | アポトーシスシグナル調節キナーゼ１阻害剤 | |
| US8178555B2 (en) | Apoptosis signal-regulating kinase 1 inhibitors | |
| EP2822559B1 (en) | Imidazo[1,2-b]pyridazine-based compounds, compositions comprising them, and uses thereof | |
| WO2011041293A1 (en) | Pyrazolo [1, 5-a] pyrimidine derivatives as apoptosis signal-regulating kinase 1 inhibitors | |
| EP4031552B1 (en) | Azole-fused pyridazin-3(2h)-one derivatives | |
| KR20190018645A (ko) | 무스카린성 아세틸콜린 수용체 m4의 양성 알로스테릭 조절제 | |
| CN100376580C (zh) | 作为细胞周期蛋白依赖性激酶抑制剂的吡唑并嘧啶 | |
| IL227294A (en) | Heterocyclic history and their use in the treatment of neurological disorders | |
| US20250289792A1 (en) | 3-amino-4h-benzo[e][1,2,4]thiadiazine 1,1-dioxide derivatives as inhibitors of mrgx2 | |
| AU2659099A (en) | Bicyclic pyridine and pyrimidine derivatives as neuropeptide y receptor antagonists | |
| CN103038233A (zh) | 吡啶酮和氮杂吡啶酮化合物及使用方法 | |
| JPWO2004043936A1 (ja) | Ｐｌｋ阻害剤 | |
| TW201217362A (en) | Heteroaryls and uses thereof | |
| TW201446767A (zh) | 作為磷脂肌醇3-激酶抑製劑之吡咯並三嗪衍生物 | |
| CN120712252A (zh) | 包含sos1抑制剂和抗癌药物的用于治疗癌症的药物组合物 | |
| CN101663276A (zh) | 用作激酶抑制剂的2-氨基吡啶衍生物 | |
| HK40076219B (en) | Azole-fused pyridazin-3(2h)-one derivatives | |
| HK40076219A (en) | Azole-fused pyridazin-3(2h)-one derivatives | |
| NZ615557B2 (en) | Pyrrolo [2,3-d] pyrimidine derivatives as inhibitors of tropomyosin- related kinases | |
| NZ615557A (en) | Pyrrolo [2,3-d] pyrimidine derivatives as inhibitors of tropomyosin- related kinases |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120330 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20120330 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130919 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20131029 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20131120 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20131206 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 Ref document number: 5432982 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |