TWI781177B - 作為C5a抑制劑之6-5稠合環 - Google Patents
作為C5a抑制劑之6-5稠合環 Download PDFInfo
- Publication number
- TWI781177B TWI781177B TW107118601A TW107118601A TWI781177B TW I781177 B TWI781177 B TW I781177B TW 107118601 A TW107118601 A TW 107118601A TW 107118601 A TW107118601 A TW 107118601A TW I781177 B TWI781177 B TW I781177B
- Authority
- TW
- Taiwan
- Prior art keywords
- mmol
- alkyl
- fluoro
- diethylphenyl
- pyridine
- Prior art date
Links
- 108010073240 complement C5a-inhibitors Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 142
- 150000003839 salts Chemical class 0.000 claims abstract description 52
- 102100031506 Complement C5 Human genes 0.000 claims abstract description 48
- 101000941598 Homo sapiens Complement C5 Proteins 0.000 claims abstract description 48
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 46
- 201000010099 disease Diseases 0.000 claims abstract description 37
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
- 230000004913 activation Effects 0.000 claims abstract description 12
- 208000035475 disorder Diseases 0.000 claims abstract description 6
- 230000001575 pathological effect Effects 0.000 claims abstract description 4
- -1 cyano, hydroxyl Chemical group 0.000 claims description 173
- 239000000203 mixture Substances 0.000 claims description 162
- 125000000217 alkyl group Chemical group 0.000 claims description 108
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- 125000005842 heteroatom Chemical group 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 229910052760 oxygen Inorganic materials 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 229910052717 sulfur Inorganic materials 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 239000003814 drug Substances 0.000 claims description 21
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 125000001188 haloalkyl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 210000000265 leukocyte Anatomy 0.000 claims description 11
- 229940079593 drug Drugs 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 206010047115 Vasculitis Diseases 0.000 claims description 8
- 125000006648 (C1-C8) haloalkyl group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 230000001404 mediated effect Effects 0.000 claims description 7
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 6
- 208000005777 Lupus Nephritis Diseases 0.000 claims description 6
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
- 208000023275 Autoimmune disease Diseases 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000002837 carbocyclic group Chemical group 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 201000008383 nephritis Diseases 0.000 claims description 5
- 210000000056 organ Anatomy 0.000 claims description 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
- 208000035913 Atypical hemolytic uremic syndrome Diseases 0.000 claims description 4
- 206010018364 Glomerulonephritis Diseases 0.000 claims description 4
- 206010025323 Lymphomas Diseases 0.000 claims description 4
- 208000009956 adenocarcinoma Diseases 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 230000008021 deposition Effects 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 208000004235 neutropenia Diseases 0.000 claims description 4
- 208000003154 papilloma Diseases 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 3
- 125000005218 alkyleneheteroaryl group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 230000001363 autoimmune Effects 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 208000017169 kidney disease Diseases 0.000 claims description 3
- 206010025135 lupus erythematosus Diseases 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
- 208000003200 Adenoma Diseases 0.000 claims description 2
- 201000003076 Angiosarcoma Diseases 0.000 claims description 2
- 206010004146 Basal cell carcinoma Diseases 0.000 claims description 2
- 206010006417 Bronchial carcinoma Diseases 0.000 claims description 2
- 208000016323 C3 glomerulonephritis Diseases 0.000 claims description 2
- 208000029574 C3 glomerulopathy Diseases 0.000 claims description 2
- 201000009030 Carcinoma Diseases 0.000 claims description 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
- 201000005262 Chondroma Diseases 0.000 claims description 2
- 208000005243 Chondrosarcoma Diseases 0.000 claims description 2
- 208000006332 Choriocarcinoma Diseases 0.000 claims description 2
- 206010048832 Colon adenoma Diseases 0.000 claims description 2
- 201000005171 Cystadenoma Diseases 0.000 claims description 2
- 201000008808 Fibrosarcoma Diseases 0.000 claims description 2
- 206010072579 Granulomatosis with polyangiitis Diseases 0.000 claims description 2
- 208000001258 Hemangiosarcoma Diseases 0.000 claims description 2
- 208000032759 Hemolytic-Uremic Syndrome Diseases 0.000 claims description 2
- 208000011200 Kawasaki disease Diseases 0.000 claims description 2
- 208000018142 Leiomyosarcoma Diseases 0.000 claims description 2
- 206010024612 Lipoma Diseases 0.000 claims description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 2
- 206010025219 Lymphangioma Diseases 0.000 claims description 2
- 206010027406 Mesothelioma Diseases 0.000 claims description 2
- 208000006265 Renal cell carcinoma Diseases 0.000 claims description 2
- 208000005678 Rhabdomyoma Diseases 0.000 claims description 2
- 206010039491 Sarcoma Diseases 0.000 claims description 2
- 201000010208 Seminoma Diseases 0.000 claims description 2
- 206010052779 Transplant rejections Diseases 0.000 claims description 2
- 208000008383 Wilms tumor Diseases 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 208000003362 bronchogenic carcinoma Diseases 0.000 claims description 2
- 208000026106 cerebrovascular disease Diseases 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 208000002445 cystadenocarcinoma Diseases 0.000 claims description 2
- 230000002526 effect on cardiovascular system Effects 0.000 claims description 2
- 208000014616 embryonal neoplasm Diseases 0.000 claims description 2
- 206010016629 fibroma Diseases 0.000 claims description 2
- 201000011066 hemangioma Diseases 0.000 claims description 2
- 230000002949 hemolytic effect Effects 0.000 claims description 2
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 2
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 2
- 201000010260 leiomyoma Diseases 0.000 claims description 2
- 208000032839 leukemia Diseases 0.000 claims description 2
- 206010024627 liposarcoma Diseases 0.000 claims description 2
- 201000005202 lung cancer Diseases 0.000 claims description 2
- 208000020816 lung neoplasm Diseases 0.000 claims description 2
- 208000012804 lymphangiosarcoma Diseases 0.000 claims description 2
- 201000001441 melanoma Diseases 0.000 claims description 2
- 206010027191 meningioma Diseases 0.000 claims description 2
- 208000001725 mucocutaneous lymph node syndrome Diseases 0.000 claims description 2
- 201000008026 nephroblastoma Diseases 0.000 claims description 2
- 230000002988 nephrogenic effect Effects 0.000 claims description 2
- 208000027134 non-immunoglobulin-mediated membranoproliferative glomerulonephritis Diseases 0.000 claims description 2
- 208000008798 osteoma Diseases 0.000 claims description 2
- 201000008968 osteosarcoma Diseases 0.000 claims description 2
- 201000010198 papillary carcinoma Diseases 0.000 claims description 2
- 208000004333 pleomorphic adenoma Diseases 0.000 claims description 2
- 201000009410 rhabdomyosarcoma Diseases 0.000 claims description 2
- 206010041823 squamous cell carcinoma Diseases 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- 230000003582 thrombocytopenic effect Effects 0.000 claims description 2
- 206010044412 transitional cell carcinoma Diseases 0.000 claims description 2
- 208000022271 tubular adenoma Diseases 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- XGWFJBFNAQHLEF-UHFFFAOYSA-N 9-anthroic acid Chemical compound C1=CC=C2C(C(=O)O)=C(C=CC=C3)C3=CC2=C1 XGWFJBFNAQHLEF-UHFFFAOYSA-N 0.000 claims 1
- 208000033694 Generalised erythema Diseases 0.000 claims 1
- 208000010159 IgA glomerulonephritis Diseases 0.000 claims 1
- 206010021263 IgA nephropathy Diseases 0.000 claims 1
- 230000000919 anti-host Effects 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 230000034196 cell chemotaxis Effects 0.000 claims 1
- 201000008171 proliferative glomerulonephritis Diseases 0.000 claims 1
- 230000001105 regulatory effect Effects 0.000 claims 1
- 201000008753 synovium neoplasm Diseases 0.000 claims 1
- 108010059426 Anaphylatoxin C5a Receptor Proteins 0.000 abstract description 53
- 102000005590 Anaphylatoxin C5a Receptor Human genes 0.000 abstract description 53
- 238000011282 treatment Methods 0.000 abstract description 26
- 238000000034 method Methods 0.000 abstract description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 508
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 305
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 292
- 235000019439 ethyl acetate Nutrition 0.000 description 251
- PUACTIIESPYWSI-UHFFFAOYSA-N 3-propan-2-ylpyridine Chemical compound CC(C)C1=CC=CN=C1 PUACTIIESPYWSI-UHFFFAOYSA-N 0.000 description 250
- 239000011541 reaction mixture Substances 0.000 description 184
- 239000002904 solvent Substances 0.000 description 168
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 166
- 230000002829 reductive effect Effects 0.000 description 159
- 239000000741 silica gel Substances 0.000 description 121
- 229910002027 silica gel Inorganic materials 0.000 description 121
- 238000003818 flash chromatography Methods 0.000 description 120
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 117
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 110
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 98
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 89
- 239000000725 suspension Substances 0.000 description 81
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 78
- 239000012267 brine Substances 0.000 description 77
- 238000005481 NMR spectroscopy Methods 0.000 description 75
- 230000015572 biosynthetic process Effects 0.000 description 69
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 68
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 66
- 239000000243 solution Substances 0.000 description 65
- 238000003786 synthesis reaction Methods 0.000 description 63
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 58
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 55
- 239000000460 chlorine Substances 0.000 description 55
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 52
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 44
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 37
- 238000001816 cooling Methods 0.000 description 36
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 35
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 34
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 34
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 33
- 229910052938 sodium sulfate Inorganic materials 0.000 description 33
- 235000011152 sodium sulphate Nutrition 0.000 description 33
- 239000011734 sodium Substances 0.000 description 32
- 239000007832 Na2SO4 Substances 0.000 description 30
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 28
- 239000012044 organic layer Substances 0.000 description 24
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 20
- 238000004809 thin layer chromatography Methods 0.000 description 20
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 19
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 17
- 229910052808 lithium carbonate Inorganic materials 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 16
- 238000001665 trituration Methods 0.000 description 16
- 239000002253 acid Substances 0.000 description 15
- 238000004128 high performance liquid chromatography Methods 0.000 description 15
- 239000004480 active ingredient Substances 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- TYCYTQLXAIDJNF-UHFFFAOYSA-N 2-chloro-5-(trifluoromethyl)pyrimidine Chemical compound FC(F)(F)C1=CN=C(Cl)N=C1 TYCYTQLXAIDJNF-UHFFFAOYSA-N 0.000 description 13
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
- 210000000440 neutrophil Anatomy 0.000 description 13
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 13
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 12
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 12
- 229920006395 saturated elastomer Polymers 0.000 description 12
- 230000027455 binding Effects 0.000 description 11
- IBHRUOJKLLUBQG-UHFFFAOYSA-L magnesium;ethene;dibromide Chemical compound [Mg+2].[Br-].[Br-].C=C IBHRUOJKLLUBQG-UHFFFAOYSA-L 0.000 description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 10
- 230000035605 chemotaxis Effects 0.000 description 10
- 238000000338 in vitro Methods 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 210000001519 tissue Anatomy 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- PIFZPZCEFJKXGQ-UHFFFAOYSA-N BrC=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1F)C(F)(F)F)C1=C(C=CC=C1CC)CC Chemical compound BrC=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1F)C(F)(F)F)C1=C(C=CC=C1CC)CC PIFZPZCEFJKXGQ-UHFFFAOYSA-N 0.000 description 9
- 206010061218 Inflammation Diseases 0.000 description 9
- 238000003556 assay Methods 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 150000002431 hydrogen Chemical class 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 229940124597 therapeutic agent Drugs 0.000 description 9
- FVHLVUNLODSXNU-UHFFFAOYSA-N Cl.CCc1cccc(CC)c1-n1nc2CCNCc2c1-c1ccc(Cl)c2[nH]ccc12 Chemical compound Cl.CCc1cccc(CC)c1-n1nc2CCNCc2c1-c1ccc(Cl)c2[nH]ccc12 FVHLVUNLODSXNU-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 239000005557 antagonist Substances 0.000 description 8
- 230000004054 inflammatory process Effects 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 238000003760 magnetic stirring Methods 0.000 description 8
- 230000037361 pathway Effects 0.000 description 8
- 239000000523 sample Substances 0.000 description 8
- 210000002966 serum Anatomy 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 235000019270 ammonium chloride Nutrition 0.000 description 7
- 210000004369 blood Anatomy 0.000 description 7
- 239000008280 blood Substances 0.000 description 7
- 230000004154 complement system Effects 0.000 description 7
- 208000010125 myocardial infarction Diseases 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 239000000546 pharmaceutical excipient Substances 0.000 description 7
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 6
- XIFCGIKPAAZFFS-UHFFFAOYSA-N 2,3-difluoro-5-(trifluoromethyl)pyridine Chemical compound FC1=CC(C(F)(F)F)=CN=C1F XIFCGIKPAAZFFS-UHFFFAOYSA-N 0.000 description 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 6
- CPCHRGFQWZMVNX-UHFFFAOYSA-N 5-(trifluoromethyl)pyrimidine Chemical compound FC(F)(F)C1=CN=CN=C1 CPCHRGFQWZMVNX-UHFFFAOYSA-N 0.000 description 6
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- 201000004681 Psoriasis Diseases 0.000 description 6
- 206010063837 Reperfusion injury Diseases 0.000 description 6
- 206010040047 Sepsis Diseases 0.000 description 6
- 150000007513 acids Chemical class 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
- 150000008049 diazo compounds Chemical class 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000000796 flavoring agent Substances 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 239000003446 ligand Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 230000001681 protective effect Effects 0.000 description 6
- 102000005962 receptors Human genes 0.000 description 6
- 108020003175 receptors Proteins 0.000 description 6
- 239000003765 sweetening agent Substances 0.000 description 6
- 208000024891 symptom Diseases 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- QTGARLPTMPKZOI-UHFFFAOYSA-N Cl.BrC=1N(N=C2C=1CNCC2)C1=C(C=CC=C1CC)CC Chemical compound Cl.BrC=1N(N=C2C=1CNCC2)C1=C(C=CC=C1CC)CC QTGARLPTMPKZOI-UHFFFAOYSA-N 0.000 description 5
- 102100022133 Complement C3 Human genes 0.000 description 5
- 101000901154 Homo sapiens Complement C3 Proteins 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 208000004852 Lung Injury Diseases 0.000 description 5
- 208000010718 Multiple Organ Failure Diseases 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 206010069363 Traumatic lung injury Diseases 0.000 description 5
- 229940024606 amino acid Drugs 0.000 description 5
- 235000001014 amino acid Nutrition 0.000 description 5
- 150000001413 amino acids Chemical class 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 230000024203 complement activation Effects 0.000 description 5
- 239000007859 condensation product Substances 0.000 description 5
- 230000006378 damage Effects 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 5
- 235000003599 food sweetener Nutrition 0.000 description 5
- 231100001261 hazardous Toxicity 0.000 description 5
- 125000004404 heteroalkyl group Chemical group 0.000 description 5
- 230000001965 increasing effect Effects 0.000 description 5
- 230000028709 inflammatory response Effects 0.000 description 5
- 231100000515 lung injury Toxicity 0.000 description 5
- 208000029744 multiple organ dysfunction syndrome Diseases 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 230000036961 partial effect Effects 0.000 description 5
- 229940002612 prodrug Drugs 0.000 description 5
- 239000000651 prodrug Substances 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 125000004434 sulfur atom Chemical group 0.000 description 5
- 208000011580 syndromic disease Diseases 0.000 description 5
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 5
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 5
- WYWHKKSPHMUBEB-UHFFFAOYSA-N tioguanine Chemical compound N1C(N)=NC(=S)C2=C1N=CN2 WYWHKKSPHMUBEB-UHFFFAOYSA-N 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- DOZAAVRVYZXAHI-UHFFFAOYSA-N 7-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-indole Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(Cl)C2=C1C=CN2 DOZAAVRVYZXAHI-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- AYJMKNWNTNQSFM-UHFFFAOYSA-N Cl.CCc1cccc(CC)c1-n1nc2CCNCc2c1-c1c(F)cc(Cl)c2[nH]ccc12 Chemical compound Cl.CCc1cccc(CC)c1-n1nc2CCNCc2c1-c1c(F)cc(Cl)c2[nH]ccc12 AYJMKNWNTNQSFM-UHFFFAOYSA-N 0.000 description 4
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 4
- 108010036949 Cyclosporine Proteins 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 241000282412 Homo Species 0.000 description 4
- 229910010084 LiAlH4 Inorganic materials 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 241000288906 Primates Species 0.000 description 4
- 206010040070 Septic Shock Diseases 0.000 description 4
- 241000282887 Suidae Species 0.000 description 4
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 description 4
- 208000007536 Thrombosis Diseases 0.000 description 4
- 229940022663 acetate Drugs 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000007900 aqueous suspension Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000003399 chemotactic effect Effects 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 230000000295 complement effect Effects 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 238000000132 electrospray ionisation Methods 0.000 description 4
- 210000002889 endothelial cell Anatomy 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 235000013355 food flavoring agent Nutrition 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000012280 lithium aluminium hydride Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 201000006417 multiple sclerosis Diseases 0.000 description 4
- 208000031225 myocardial ischemia Diseases 0.000 description 4
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 4
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 4
- 231100000252 nontoxic Toxicity 0.000 description 4
- 230000003000 nontoxic effect Effects 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000003755 preservative agent Substances 0.000 description 4
- 108090000765 processed proteins & peptides Proteins 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000012047 saturated solution Substances 0.000 description 4
- 210000003491 skin Anatomy 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 235000017550 sodium carbonate Nutrition 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 235000011149 sulphuric acid Nutrition 0.000 description 4
- 239000000375 suspending agent Substances 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- 230000000451 tissue damage Effects 0.000 description 4
- 231100000827 tissue damage Toxicity 0.000 description 4
- 238000002054 transplantation Methods 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- NCWDBNBNYVVARF-UHFFFAOYSA-N 1,3,2-dioxaborolane Chemical compound B1OCCO1 NCWDBNBNYVVARF-UHFFFAOYSA-N 0.000 description 3
- AGRIQBHIKABLPJ-UHFFFAOYSA-N 1-Pyrrolidinecarboxaldehyde Chemical compound O=CN1CCCC1 AGRIQBHIKABLPJ-UHFFFAOYSA-N 0.000 description 3
- WCXFPLXZZSWROM-UHFFFAOYSA-N 1h-pyrazolo[4,3-c]pyridine Chemical compound C1=NC=C2C=NNC2=C1 WCXFPLXZZSWROM-UHFFFAOYSA-N 0.000 description 3
- FCJRWVLIOXVZFS-UHFFFAOYSA-N 2,3-difluoro-5-propan-2-ylpyridine Chemical compound CC(C)C1=CN=C(F)C(F)=C1 FCJRWVLIOXVZFS-UHFFFAOYSA-N 0.000 description 3
- KYUDTBPIZLFHNU-UHFFFAOYSA-N 2-fluoro-5-propan-2-ylpyridine Chemical compound CC(C)C1=CC=C(F)N=C1 KYUDTBPIZLFHNU-UHFFFAOYSA-N 0.000 description 3
- KNECNPCFKNMBHM-UHFFFAOYSA-N 3-bromo-2-(2,6-dimethylphenyl)-5-[3-fluoro-5-(trifluoromethyl)pyridin-2-yl]-6,7-dihydro-4H-pyrazolo[4,3-c]pyridine Chemical compound BrC=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1F)C(F)(F)F)C1=C(C=CC=C1C)C KNECNPCFKNMBHM-UHFFFAOYSA-N 0.000 description 3
- VGMJQHONPAXABH-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1h-pyrazolo[4,3-c]pyridine Chemical compound C1NCCC2=C1C=NN2 VGMJQHONPAXABH-UHFFFAOYSA-N 0.000 description 3
- STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 description 3
- 208000030507 AIDS Diseases 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 3
- 208000024827 Alzheimer disease Diseases 0.000 description 3
- BNBJEUIKDKOIOO-UHFFFAOYSA-N C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CN(CC2)C2=NC=C(C=C2F)C(F)(F)F)=C1C1=C2C=CNC2=C(C=C1)C(=O)N Chemical compound C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CN(CC2)C2=NC=C(C=C2F)C(F)(F)F)=C1C1=C2C=CNC2=C(C=C1)C(=O)N BNBJEUIKDKOIOO-UHFFFAOYSA-N 0.000 description 3
- JQRDNVXQYYRNDZ-UHFFFAOYSA-N C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CN(CC2)C2=NC=C(C=C2F)C(F)(F)F)=C1C1=C2C=CNC2=C(C=C1)C(=O)OC Chemical compound C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CN(CC2)C2=NC=C(C=C2F)C(F)(F)F)=C1C1=C2C=CNC2=C(C=C1)C(=O)OC JQRDNVXQYYRNDZ-UHFFFAOYSA-N 0.000 description 3
- CFCXGTJYYJSXKX-UHFFFAOYSA-N C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CN(CC2)C2=NC=C(C=N2)C(F)(F)F)=C1C1=C2C=CNC2=C(C(=C1)F)C Chemical compound C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CN(CC2)C2=NC=C(C=N2)C(F)(F)F)=C1C1=C2C=CNC2=C(C(=C1)F)C CFCXGTJYYJSXKX-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 3
- FXVFFTDOCZKYOK-UHFFFAOYSA-N Cl.C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CNCC2)=C1C1=C2C=CNC2=C(C(=C1)F)CO Chemical compound Cl.C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CNCC2)=C1C1=C2C=CNC2=C(C(=C1)F)CO FXVFFTDOCZKYOK-UHFFFAOYSA-N 0.000 description 3
- JMHSLISHDBRZAA-UHFFFAOYSA-N Cl.C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CNCC2)=C1C1=C2C=CNC2=C(C=C1)OC Chemical compound Cl.C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CNCC2)=C1C1=C2C=CNC2=C(C=C1)OC JMHSLISHDBRZAA-UHFFFAOYSA-N 0.000 description 3
- QUVSXONXACTJLY-UHFFFAOYSA-N Cl.CCc1cccc(CC)c1-n1nc2CCNCc2c1-c1c(F)cc(OC)c2[nH]ccc12 Chemical compound Cl.CCc1cccc(CC)c1-n1nc2CCNCc2c1-c1c(F)cc(OC)c2[nH]ccc12 QUVSXONXACTJLY-UHFFFAOYSA-N 0.000 description 3
- YSGOSJGASFLSTG-UHFFFAOYSA-N Cl.CCc1cccc(CC)c1-n1nc2CCNCc2c1-c1cc(Cl)c(C)c2[nH]ccc12 Chemical compound Cl.CCc1cccc(CC)c1-n1nc2CCNCc2c1-c1cc(Cl)c(C)c2[nH]ccc12 YSGOSJGASFLSTG-UHFFFAOYSA-N 0.000 description 3
- PIVCNRAOVBOBFK-UHFFFAOYSA-N Cl.FC=1C(=C2C=NNC2=C(C=1)C)C=1N(N=C2C=1CNCC2)C1=C(C=CC=C1C)C Chemical compound Cl.FC=1C(=C2C=NNC2=C(C=1)C)C=1N(N=C2C=1CNCC2)C1=C(C=CC=C1C)C PIVCNRAOVBOBFK-UHFFFAOYSA-N 0.000 description 3
- FBRAWBYQGRLCEK-AVVSTMBFSA-N Clobetasone butyrate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CCl)(OC(=O)CCC)[C@@]1(C)CC2=O FBRAWBYQGRLCEK-AVVSTMBFSA-N 0.000 description 3
- 108010034753 Complement Membrane Attack Complex Proteins 0.000 description 3
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 3
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 3
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 208000031886 HIV Infections Diseases 0.000 description 3
- 208000037357 HIV infectious disease Diseases 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 3
- 240000007472 Leucaena leucocephala Species 0.000 description 3
- 229910010082 LiAlH Inorganic materials 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 208000034486 Multi-organ failure Diseases 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000556 agonist Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 210000004204 blood vessel Anatomy 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 230000002612 cardiopulmonary effect Effects 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- CBGUOGMQLZIXBE-XGQKBEPLSA-N clobetasol propionate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CCl)(OC(=O)CC)[C@@]1(C)C[C@@H]2O CBGUOGMQLZIXBE-XGQKBEPLSA-N 0.000 description 3
- 229960004397 cyclophosphamide Drugs 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 229960002949 fluorouracil Drugs 0.000 description 3
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 230000014509 gene expression Effects 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 230000036541 health Effects 0.000 description 3
- 210000003630 histaminocyte Anatomy 0.000 description 3
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 3
- 239000003018 immunosuppressive agent Substances 0.000 description 3
- 230000001939 inductive effect Effects 0.000 description 3
- 230000008595 infiltration Effects 0.000 description 3
- 238000001764 infiltration Methods 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 208000014674 injury Diseases 0.000 description 3
- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 3
- 210000003734 kidney Anatomy 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229940057995 liquid paraffin Drugs 0.000 description 3
- 239000007937 lozenge Substances 0.000 description 3
- 210000004072 lung Anatomy 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 3
- 210000001616 monocyte Anatomy 0.000 description 3
- 208000015122 neurodegenerative disease Diseases 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 239000004006 olive oil Substances 0.000 description 3
- 235000008390 olive oil Nutrition 0.000 description 3
- 230000008506 pathogenesis Effects 0.000 description 3
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 3
- 210000005134 plasmacytoid dendritic cell Anatomy 0.000 description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
- 230000003389 potentiating effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 229960002794 prednicarbate Drugs 0.000 description 3
- FNPXMHRZILFCKX-KAJVQRHHSA-N prednicarbate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)CC)(OC(=O)OCC)[C@@]1(C)C[C@@H]2O FNPXMHRZILFCKX-KAJVQRHHSA-N 0.000 description 3
- 229960004618 prednisone Drugs 0.000 description 3
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 3
- 238000002953 preparative HPLC Methods 0.000 description 3
- 230000027425 release of sequestered calcium ion into cytosol Effects 0.000 description 3
- 230000028327 secretion Effects 0.000 description 3
- 230000036303 septic shock Effects 0.000 description 3
- 230000007781 signaling event Effects 0.000 description 3
- QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 229960005294 triamcinolone Drugs 0.000 description 3
- GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 3
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- UVLLWONKDNEWDL-UHFFFAOYSA-N (2,6-diethylphenyl)hydrazine;hydrochloride Chemical compound Cl.CCC1=CC=CC(CC)=C1NN UVLLWONKDNEWDL-UHFFFAOYSA-N 0.000 description 2
- 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
- FPVKHBSQESCIEP-UHFFFAOYSA-N (8S)-3-(2-deoxy-beta-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol Natural products C1C(O)C(CO)OC1N1C(NC=NCC2O)=C2N=C1 FPVKHBSQESCIEP-UHFFFAOYSA-N 0.000 description 2
- FDKXTQMXEQVLRF-ZHACJKMWSA-N (E)-dacarbazine Chemical compound CN(C)\N=N\c1[nH]cnc1C(N)=O FDKXTQMXEQVLRF-ZHACJKMWSA-N 0.000 description 2
- AFZZYIJIWUTJFO-UHFFFAOYSA-N 1,3-diethylbenzene Chemical compound CCC1=CC=CC(CC)=C1 AFZZYIJIWUTJFO-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
- WKQCPUMQBMFPLC-ZWFCQKKLSA-N 11beta,21-Dihydroxypregn-4-ene-3,20-dione 21-acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)COC(=O)C)[C@@]1(C)C[C@@H]2O WKQCPUMQBMFPLC-ZWFCQKKLSA-N 0.000 description 2
- BQDJLAWUTBCDHK-UHFFFAOYSA-N 2-(trifluoromethyl)pyrimidine Chemical compound FC(F)(F)C1=NC=CC=N1 BQDJLAWUTBCDHK-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- HKPSEPKHIOHODX-UHFFFAOYSA-N 2-bromo-5-chloro-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=CC(Cl)=CC=C1Br HKPSEPKHIOHODX-UHFFFAOYSA-N 0.000 description 2
- JQYBPXNUAJSJBK-UHFFFAOYSA-N 2-fluoro-5-prop-1-en-2-ylpyridine Chemical compound CC(=C)C1=CC=C(F)N=C1 JQYBPXNUAJSJBK-UHFFFAOYSA-N 0.000 description 2
- IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 2
- NYVQCSJKUKTWRU-UHFFFAOYSA-N 2h-pyrrolo[3,4-c]pyridine Chemical compound C1=NC=CC2=CNC=C21 NYVQCSJKUKTWRU-UHFFFAOYSA-N 0.000 description 2
- FHQWUIZMJXPGRG-UHFFFAOYSA-N 3,5-dichloro-2-fluoropyridine Chemical compound FC1=NC=C(Cl)C=C1Cl FHQWUIZMJXPGRG-UHFFFAOYSA-N 0.000 description 2
- GWTMPNXPVMDUTM-UHFFFAOYSA-N 3-fluoro-5-(trifluoromethyl)pyridine Chemical compound FC1=CN=CC(C(F)(F)F)=C1 GWTMPNXPVMDUTM-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- DJRYWPGOQTUJMQ-UHFFFAOYSA-N 4-bromo-1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Br)=CC=C1Cl DJRYWPGOQTUJMQ-UHFFFAOYSA-N 0.000 description 2
- NDJPAWIBZAMBIT-UHFFFAOYSA-N 4-bromo-2-fluoro-6-nitrobenzoic acid Chemical compound OC(=O)c1c(F)cc(Br)cc1[N+]([O-])=O NDJPAWIBZAMBIT-UHFFFAOYSA-N 0.000 description 2
- PCQMVARIFZIVLE-UHFFFAOYSA-N 4-bromo-3-chloro-7-fluoro-1H-indole Chemical compound Fc1ccc(Br)c2c(Cl)c[nH]c12 PCQMVARIFZIVLE-UHFFFAOYSA-N 0.000 description 2
- FSYLMKGDYWCVJG-UHFFFAOYSA-N 4-bromo-3-chloro-7-methyl-1H-indole Chemical compound Cc1ccc(Br)c2c(Cl)c[nH]c12 FSYLMKGDYWCVJG-UHFFFAOYSA-N 0.000 description 2
- VBEREHXOPRSXBI-UHFFFAOYSA-N 4-bromo-5-fluoro-7-methyl-1h-indole Chemical compound CC1=CC(F)=C(Br)C2=C1NC=C2 VBEREHXOPRSXBI-UHFFFAOYSA-N 0.000 description 2
- DFVFXVDSICLMAC-UHFFFAOYSA-N 4-bromo-6,7-difluoro-1h-indole Chemical compound FC1=CC(Br)=C2C=CNC2=C1F DFVFXVDSICLMAC-UHFFFAOYSA-N 0.000 description 2
- PQWHJIZXLSZLTC-UHFFFAOYSA-N 4-bromo-6-chloro-7-methyl-1h-indole Chemical compound CC1=C(Cl)C=C(Br)C2=C1NC=C2 PQWHJIZXLSZLTC-UHFFFAOYSA-N 0.000 description 2
- APJWRMDDRQDBDX-UHFFFAOYSA-N 4-bromo-6-fluoro-7-methyl-1h-indole Chemical compound CC1=C(F)C=C(Br)C2=C1NC=C2 APJWRMDDRQDBDX-UHFFFAOYSA-N 0.000 description 2
- ABBUZRXDYLQKRH-UHFFFAOYSA-N 4-bromo-7-chloro-1h-indole Chemical compound ClC1=CC=C(Br)C2=C1NC=C2 ABBUZRXDYLQKRH-UHFFFAOYSA-N 0.000 description 2
- QULWOGLBWMRZGR-UHFFFAOYSA-N 4-bromo-7-chloro-1h-pyrrolo[3,2-c]pyridine Chemical compound ClC1=CN=C(Br)C2=C1NC=C2 QULWOGLBWMRZGR-UHFFFAOYSA-N 0.000 description 2
- DUUKASPZHPJXHG-UHFFFAOYSA-N 4-bromo-7-chloro-3-methyl-1H-indole Chemical compound Cc1c[nH]c2c(Cl)ccc(Br)c12 DUUKASPZHPJXHG-UHFFFAOYSA-N 0.000 description 2
- JSRNNMJLUUHMNE-UHFFFAOYSA-N 4-bromo-7-chloro-5-fluoro-1H-indole Chemical compound BrC1=C2C=CNC2=C(C=C1F)Cl JSRNNMJLUUHMNE-UHFFFAOYSA-N 0.000 description 2
- PBQKMEMSAFAVKF-UHFFFAOYSA-N 4-bromo-7-fluoro-1h-indole Chemical compound FC1=CC=C(Br)C2=C1NC=C2 PBQKMEMSAFAVKF-UHFFFAOYSA-N 0.000 description 2
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 2
- XHJAOEKASUFHHN-UHFFFAOYSA-N 5-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=C=NC=C[CH]1 XHJAOEKASUFHHN-UHFFFAOYSA-N 0.000 description 2
- NESQKIOPMZAINF-UHFFFAOYSA-N 5-bromo-1-chloro-2-methoxy-3-nitrobenzene Chemical compound BrC=1C=C(C(=C(C=1)Cl)OC)[N+](=O)[O-] NESQKIOPMZAINF-UHFFFAOYSA-N 0.000 description 2
- QZUIGBPWEFMEEV-UHFFFAOYSA-N 5-bromo-1-fluoro-2-methyl-3-nitrobenzene Chemical compound CC1=C(F)C=C(Br)C=C1[N+]([O-])=O QZUIGBPWEFMEEV-UHFFFAOYSA-N 0.000 description 2
- QVIQXJRQVOPYGI-UHFFFAOYSA-N 5-bromo-2,3-difluoropyridine Chemical compound FC1=CC(Br)=CN=C1F QVIQXJRQVOPYGI-UHFFFAOYSA-N 0.000 description 2
- AQVSGQVOLJDRTE-UHFFFAOYSA-N 6-bromo-2,4-difluoro-3-methoxybenzaldehyde Chemical compound COC1=C(F)C=C(Br)C(C=O)=C1F AQVSGQVOLJDRTE-UHFFFAOYSA-N 0.000 description 2
- VOVCSVCFVXVNJD-UHFFFAOYSA-N 7-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-indole Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(F)C2=C1C=CN2 VOVCSVCFVXVNJD-UHFFFAOYSA-N 0.000 description 2
- ZZIBGCFXRVADHU-UHFFFAOYSA-N 7-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-indazole Chemical compound C1=2C=NNC=2C(OC)=CC=C1B1OC(C)(C)C(C)(C)O1 ZZIBGCFXRVADHU-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- 108010089414 Anaphylatoxins Proteins 0.000 description 2
- 239000004475 Arginine Substances 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- 102100022005 B-lymphocyte antigen CD20 Human genes 0.000 description 2
- KZKNWJNMPADDRY-UHFFFAOYSA-N B1CCCO1 Chemical compound B1CCCO1 KZKNWJNMPADDRY-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- IFBNFSKGGLZXSA-UHFFFAOYSA-N BrC1=C2C=CNC2=C(C(=C1)Cl)OC Chemical compound BrC1=C2C=CNC2=C(C(=C1)Cl)OC IFBNFSKGGLZXSA-UHFFFAOYSA-N 0.000 description 2
- HKCAXYXYCBRBAN-UHFFFAOYSA-N BrC1=C2C=CNC2=C(C(=C1)F)Cl Chemical compound BrC1=C2C=CNC2=C(C(=C1)F)Cl HKCAXYXYCBRBAN-UHFFFAOYSA-N 0.000 description 2
- OYFVZLMXEKRBJW-UHFFFAOYSA-N BrC1=C2C=CNC2=C(C(=C1)F)OC Chemical compound BrC1=C2C=CNC2=C(C(=C1)F)OC OYFVZLMXEKRBJW-UHFFFAOYSA-N 0.000 description 2
- DTNWBNPWFHXWKI-UHFFFAOYSA-N BrC1=C2C=CNC2=C(C=C1F)OC Chemical compound BrC1=C2C=CNC2=C(C=C1F)OC DTNWBNPWFHXWKI-UHFFFAOYSA-N 0.000 description 2
- RJZBYWMZDAQMTL-UHFFFAOYSA-N BrC1=C2C=NNC2=C(C(=C1)F)OC Chemical compound BrC1=C2C=NNC2=C(C(=C1)F)OC RJZBYWMZDAQMTL-UHFFFAOYSA-N 0.000 description 2
- JJTJCFOOJGQYDX-UHFFFAOYSA-N BrC=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1Cl)Cl)C1=C(C=CC=C1C)C Chemical compound BrC=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1Cl)Cl)C1=C(C=CC=C1C)C JJTJCFOOJGQYDX-UHFFFAOYSA-N 0.000 description 2
- VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 description 2
- ODXTUWNAUNTCHQ-UHFFFAOYSA-N C(C(C)C)OC1=C(C(=CC=C1)C)[N+](=O)[O-] Chemical compound C(C(C)C)OC1=C(C(=CC=C1)C)[N+](=O)[O-] ODXTUWNAUNTCHQ-UHFFFAOYSA-N 0.000 description 2
- QXXZQZQDRXYXRP-UHFFFAOYSA-N C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CN(CC2)C(=O)OC(C)(C)C)=C1C1=C2C=CNC2=C(C(=C1)F)C(=O)OC Chemical compound C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CN(CC2)C(=O)OC(C)(C)C)=C1C1=C2C=CNC2=C(C(=C1)F)C(=O)OC QXXZQZQDRXYXRP-UHFFFAOYSA-N 0.000 description 2
- POOCARFBMKQYHU-UHFFFAOYSA-N C1(CC1)C=1C=C(C(=NC1)F)F Chemical compound C1(CC1)C=1C=C(C(=NC1)F)F POOCARFBMKQYHU-UHFFFAOYSA-N 0.000 description 2
- NBJCISJSVMLGJI-UHFFFAOYSA-N CC1=C(C(=CC=C1)C)N1N=C2C(CN(CC2)C(=O)OC(C)(C)C)=C1C1=C2C=CNC2=C(C=C1F)C(=O)OC Chemical compound CC1=C(C(=CC=C1)C)N1N=C2C(CN(CC2)C(=O)OC(C)(C)C)=C1C1=C2C=CNC2=C(C=C1F)C(=O)OC NBJCISJSVMLGJI-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 description 2
- LUKZNWIVRBCLON-GXOBDPJESA-N Ciclesonide Chemical compound C1([C@H]2O[C@@]3([C@H](O2)C[C@@H]2[C@@]3(C[C@H](O)[C@@H]3[C@@]4(C)C=CC(=O)C=C4CC[C@H]32)C)C(=O)COC(=O)C(C)C)CCCCC1 LUKZNWIVRBCLON-GXOBDPJESA-N 0.000 description 2
- XSMZEZWIGWWGKO-UHFFFAOYSA-N Cl.BrC=1N(N=C2C=1CNCC2)C1=C(C=CC=C1C)C Chemical compound Cl.BrC=1N(N=C2C=1CNCC2)C1=C(C=CC=C1C)C XSMZEZWIGWWGKO-UHFFFAOYSA-N 0.000 description 2
- CATKXZMPAUPYHA-UHFFFAOYSA-N Cl.CC(C)COc1cccc(C)c1NN Chemical compound Cl.CC(C)COc1cccc(C)c1NN CATKXZMPAUPYHA-UHFFFAOYSA-N 0.000 description 2
- VDTWMVQYUHFXCN-UHFFFAOYSA-N Cl.CCc1cccc(CC)c1-n1nc2CCNCc2c1-c1c(F)cc(CO)c2[nH]ccc12 Chemical compound Cl.CCc1cccc(CC)c1-n1nc2CCNCc2c1-c1c(F)cc(CO)c2[nH]ccc12 VDTWMVQYUHFXCN-UHFFFAOYSA-N 0.000 description 2
- BGDPLTWGQHXDFY-UHFFFAOYSA-N Cl.CCc1cccc(CC)c1-n1nc2CCNCc2c1-c1cc(F)c(C)c2[nH]ccc12 Chemical compound Cl.CCc1cccc(CC)c1-n1nc2CCNCc2c1-c1cc(F)c(C)c2[nH]ccc12 BGDPLTWGQHXDFY-UHFFFAOYSA-N 0.000 description 2
- DUSBXTIXJICSRC-UHFFFAOYSA-N Cl.CCc1cccc(CC)c1-n1nc2CCNCc2c1-c1cc(F)c(F)c2[nH]ccc12 Chemical compound Cl.CCc1cccc(CC)c1-n1nc2CCNCc2c1-c1cc(F)c(F)c2[nH]ccc12 DUSBXTIXJICSRC-UHFFFAOYSA-N 0.000 description 2
- JJWNWXKEJDIEMD-UHFFFAOYSA-N Cl.CCc1cccc(CC)c1-n1nc2CCNCc2c1-c1cc(F)c(OC)c2[nH]ccc12 Chemical compound Cl.CCc1cccc(CC)c1-n1nc2CCNCc2c1-c1cc(F)c(OC)c2[nH]ccc12 JJWNWXKEJDIEMD-UHFFFAOYSA-N 0.000 description 2
- SIBJETVGYNLMNX-UHFFFAOYSA-N Cl.CCc1cccc(CC)c1-n1nc2CCNCc2c1-c1cc(F)c(OC)c2[nH]ncc12 Chemical compound Cl.CCc1cccc(CC)c1-n1nc2CCNCc2c1-c1cc(F)c(OC)c2[nH]ncc12 SIBJETVGYNLMNX-UHFFFAOYSA-N 0.000 description 2
- HLBOOHFOZYMRTG-UHFFFAOYSA-N Cl.CCc1cccc(CC)c1-n1nc2CCNCc2c1-c1ccc(C)c2[nH]ccc12 Chemical compound Cl.CCc1cccc(CC)c1-n1nc2CCNCc2c1-c1ccc(C)c2[nH]ccc12 HLBOOHFOZYMRTG-UHFFFAOYSA-N 0.000 description 2
- HCPWTOYDHABGIB-UHFFFAOYSA-N Cl.CCc1cccc(CC)c1-n1nc2CCNCc2c1-c1ccc(Cl)c2[nH]ncc12 Chemical compound Cl.CCc1cccc(CC)c1-n1nc2CCNCc2c1-c1ccc(Cl)c2[nH]ncc12 HCPWTOYDHABGIB-UHFFFAOYSA-N 0.000 description 2
- YHFSSZGLWFBIAG-UHFFFAOYSA-N Cl.CCc1cccc(CC)c1-n1nc2CCNCc2c1-c1ccc(F)c2[nH]ccc12 Chemical compound Cl.CCc1cccc(CC)c1-n1nc2CCNCc2c1-c1ccc(F)c2[nH]ccc12 YHFSSZGLWFBIAG-UHFFFAOYSA-N 0.000 description 2
- OMUXTZUDOTUBEV-UHFFFAOYSA-N Cl.COC=1C=CC(=C2C=NNC=12)C=1N(N=C2C=1CNCC2)C1=C(C=CC=C1CC)CC Chemical compound Cl.COC=1C=CC(=C2C=NNC=12)C=1N(N=C2C=1CNCC2)C1=C(C=CC=C1CC)CC OMUXTZUDOTUBEV-UHFFFAOYSA-N 0.000 description 2
- ZDSONMDORBCAHE-UHFFFAOYSA-N Cl.Cc1cccc(C)c1-n1nc2CCNCc2c1-c1c(F)cc(CO)c2[nH]ccc12 Chemical compound Cl.Cc1cccc(C)c1-n1nc2CCNCc2c1-c1c(F)cc(CO)c2[nH]ccc12 ZDSONMDORBCAHE-UHFFFAOYSA-N 0.000 description 2
- LPFHRLSQRCFGAM-UHFFFAOYSA-N Cl.Cc1cccc(C)c1-n1nc2CCNCc2c1-c1cc(F)c(C)c2[nH]ccc12 Chemical compound Cl.Cc1cccc(C)c1-n1nc2CCNCc2c1-c1cc(F)c(C)c2[nH]ccc12 LPFHRLSQRCFGAM-UHFFFAOYSA-N 0.000 description 2
- YNRZNIHSFWHIBV-UHFFFAOYSA-N ClC1=CNC2=C(C=CC(=C12)B1OC(C(O1)(C)C)(C)C)C Chemical compound ClC1=CNC2=C(C=CC(=C12)B1OC(C(O1)(C)C)(C)C)C YNRZNIHSFWHIBV-UHFFFAOYSA-N 0.000 description 2
- PYTVFJMGOBSRGH-UHFFFAOYSA-N ClC1=CNC2=C(C=CC(=C12)B1OC(C(O1)(C)C)(C)C)F Chemical compound ClC1=CNC2=C(C=CC(=C12)B1OC(C(O1)(C)C)(C)C)F PYTVFJMGOBSRGH-UHFFFAOYSA-N 0.000 description 2
- NXNFNJFERDYBPE-UHFFFAOYSA-N ClC=1C=CC(=C2C(=CNC=12)C)B1OC(C(O1)(C)C)(C)C Chemical compound ClC=1C=CC(=C2C(=CNC=12)C)B1OC(C(O1)(C)C)(C)C NXNFNJFERDYBPE-UHFFFAOYSA-N 0.000 description 2
- UDOXWPRPHFKEHW-UHFFFAOYSA-N ClC=1C=CC(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C(=N1)C(=O)OC)C)C1=C(C=CC=C1CC)CC Chemical compound ClC=1C=CC(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C(=N1)C(=O)OC)C)C1=C(C=CC=C1CC)CC UDOXWPRPHFKEHW-UHFFFAOYSA-N 0.000 description 2
- KEKLZQROUFICER-UHFFFAOYSA-N ClC=1C=CC(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=N1)C(=O)OC)C1=C(C=CC=C1CC)CC Chemical compound ClC=1C=CC(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=N1)C(=O)OC)C1=C(C=CC=C1CC)CC KEKLZQROUFICER-UHFFFAOYSA-N 0.000 description 2
- UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 description 2
- 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 2
- 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 2
- WEAHRLBPCANXCN-UHFFFAOYSA-N Daunomycin Natural products CCC1(O)CC(OC2CC(N)C(O)C(C)O2)c3cc4C(=O)c5c(OC)cccc5C(=O)c4c(O)c3C1 WEAHRLBPCANXCN-UHFFFAOYSA-N 0.000 description 2
- 206010012438 Dermatitis atopic Diseases 0.000 description 2
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 2
- 241000283086 Equidae Species 0.000 description 2
- 108010008165 Etanercept Proteins 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- RPNMAZUWZAWYOA-UHFFFAOYSA-N FC1=NC=C(C=C1F)C(=C)C Chemical compound FC1=NC=C(C=C1F)C(=C)C RPNMAZUWZAWYOA-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- 206010016654 Fibrosis Diseases 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 2
- 208000007465 Giant cell arteritis Diseases 0.000 description 2
- 239000007821 HATU Substances 0.000 description 2
- 101000897405 Homo sapiens B-lymphocyte antigen CD20 Proteins 0.000 description 2
- 101000867983 Homo sapiens C5a anaphylatoxin chemotactic receptor 1 Proteins 0.000 description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 2
- 108090001090 Lectins Proteins 0.000 description 2
- 102000004856 Lectins Human genes 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- FQISKWAFAHGMGT-SGJOWKDISA-M Methylprednisolone sodium succinate Chemical compound [Na+].C([C@@]12C)=CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2[C@@H](O)C[C@]2(C)[C@@](O)(C(=O)COC(=O)CCC([O-])=O)CC[C@H]21 FQISKWAFAHGMGT-SGJOWKDISA-M 0.000 description 2
- MITFXPHMIHQXPI-UHFFFAOYSA-N Oraflex Chemical compound N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 2
- 229930012538 Paclitaxel Natural products 0.000 description 2
- 241001494479 Pecora Species 0.000 description 2
- 206010034277 Pemphigoid Diseases 0.000 description 2
- 201000011152 Pemphigus Diseases 0.000 description 2
- 229920000954 Polyglycolide Polymers 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 description 2
- GIIZNNXWQWCKIB-UHFFFAOYSA-N Serevent Chemical compound C1=C(O)C(CO)=CC(C(O)CNCCCCCCOCCCCC=2C=CC=CC=2)=C1 GIIZNNXWQWCKIB-UHFFFAOYSA-N 0.000 description 2
- ZSJLQEPLLKMAKR-UHFFFAOYSA-N Streptozotocin Natural products O=NN(C)C(=O)NC1C(O)OC(CO)C(O)C1O ZSJLQEPLLKMAKR-UHFFFAOYSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- 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 2
- 206010051379 Systemic Inflammatory Response Syndrome Diseases 0.000 description 2
- 210000001744 T-lymphocyte Anatomy 0.000 description 2
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 2
- 229920001615 Tragacanth Polymers 0.000 description 2
- ZZHLYYDVIOPZBE-UHFFFAOYSA-N Trimeprazine Chemical compound C1=CC=C2N(CC(CN(C)C)C)C3=CC=CC=C3SC2=C1 ZZHLYYDVIOPZBE-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 2
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 2
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 2
- 206010052568 Urticaria chronic Diseases 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- GYXAMGQJBZYFRL-UHFFFAOYSA-N [O-][N+](=O)c1cc(Br)ncc1Cl Chemical compound [O-][N+](=O)c1cc(Br)ncc1Cl GYXAMGQJBZYFRL-UHFFFAOYSA-N 0.000 description 2
- LBGKSTIPMPVHBF-UHFFFAOYSA-N [O-][n+]1cc(Cl)ccc1Br.[O-][N+](=O)c1cc(Br)[n+]([O-])cc1Cl Chemical compound [O-][n+]1cc(Cl)ccc1Br.[O-][N+](=O)c1cc(Br)[n+]([O-])cc1Cl LBGKSTIPMPVHBF-UHFFFAOYSA-N 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 229960004892 acemetacin Drugs 0.000 description 2
- FSQKKOOTNAMONP-UHFFFAOYSA-N acemetacin Chemical compound CC1=C(CC(=O)OCC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 FSQKKOOTNAMONP-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 2
- 230000000172 allergic effect Effects 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N anhydrous methyl formate Natural products COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 238000009175 antibody therapy Methods 0.000 description 2
- 239000000739 antihistaminic agent Substances 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 230000006907 apoptotic process Effects 0.000 description 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 2
- 206010003246 arthritis Diseases 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 201000008937 atopic dermatitis Diseases 0.000 description 2
- 208000010668 atopic eczema Diseases 0.000 description 2
- AUJRCFUBUPVWSZ-XTZHGVARSA-M auranofin Chemical compound CCP(CC)(CC)=[Au]S[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O AUJRCFUBUPVWSZ-XTZHGVARSA-M 0.000 description 2
- 229960005207 auranofin Drugs 0.000 description 2
- 238000000376 autoradiography Methods 0.000 description 2
- KLNFSAOEKUDMFA-UHFFFAOYSA-N azanide;2-hydroxyacetic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OCC(O)=O KLNFSAOEKUDMFA-UHFFFAOYSA-N 0.000 description 2
- 210000002469 basement membrane Anatomy 0.000 description 2
- 210000003651 basophil Anatomy 0.000 description 2
- 229940092705 beclomethasone Drugs 0.000 description 2
- NBMKJKDGKREAPL-DVTGEIKXSA-N beclomethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O NBMKJKDGKREAPL-DVTGEIKXSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 2
- 229960002537 betamethasone Drugs 0.000 description 2
- UREBDLICKHMUKA-DVTGEIKXSA-N betamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-DVTGEIKXSA-N 0.000 description 2
- 229960001102 betamethasone dipropionate Drugs 0.000 description 2
- CIWBQSYVNNPZIQ-XYWKZLDCSA-N betamethasone dipropionate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O CIWBQSYVNNPZIQ-XYWKZLDCSA-N 0.000 description 2
- PLCQGRYPOISRTQ-LWCNAHDDSA-L betamethasone sodium phosphate Chemical compound [Na+].[Na+].C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COP([O-])([O-])=O)(O)[C@@]1(C)C[C@@H]2O PLCQGRYPOISRTQ-LWCNAHDDSA-L 0.000 description 2
- 229960005354 betamethasone sodium phosphate Drugs 0.000 description 2
- SNHRLVCMMWUAJD-SUYDQAKGSA-N betamethasone valerate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(OC(=O)CCCC)[C@@]1(C)C[C@@H]2O SNHRLVCMMWUAJD-SUYDQAKGSA-N 0.000 description 2
- 229960004311 betamethasone valerate Drugs 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 208000002352 blister Diseases 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229960004436 budesonide Drugs 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
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 235000010216 calcium carbonate Nutrition 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- 229910000389 calcium phosphate Inorganic materials 0.000 description 2
- 235000011010 calcium phosphates Nutrition 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 210000000038 chest Anatomy 0.000 description 2
- 239000007910 chewable tablet Substances 0.000 description 2
- 208000024376 chronic urticaria Diseases 0.000 description 2
- 229960003728 ciclesonide Drugs 0.000 description 2
- 229960001265 ciclosporin Drugs 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 229960004703 clobetasol propionate Drugs 0.000 description 2
- 229960005465 clobetasone butyrate Drugs 0.000 description 2
- 238000002648 combination therapy Methods 0.000 description 2
- 238000013270 controlled release Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000003246 corticosteroid Substances 0.000 description 2
- 229960001334 corticosteroids Drugs 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 229960000975 daunorubicin Drugs 0.000 description 2
- 230000002939 deleterious effect Effects 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- WBGKWQHBNHJJPZ-LECWWXJVSA-N desonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O WBGKWQHBNHJJPZ-LECWWXJVSA-N 0.000 description 2
- 229960003662 desonide Drugs 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 229960003957 dexamethasone Drugs 0.000 description 2
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 2
- 229960002344 dexamethasone sodium phosphate Drugs 0.000 description 2
- PLCQGRYPOISRTQ-FCJDYXGNSA-L dexamethasone sodium phosphate Chemical compound [Na+].[Na+].C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)COP([O-])([O-])=O)(O)[C@@]1(C)C[C@@H]2O PLCQGRYPOISRTQ-FCJDYXGNSA-L 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 2
- 239000000890 drug combination Substances 0.000 description 2
- 210000003979 eosinophil Anatomy 0.000 description 2
- 229960000403 etanercept Drugs 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- ODKNJVUHOIMIIZ-RRKCRQDMSA-N floxuridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(F)=C1 ODKNJVUHOIMIIZ-RRKCRQDMSA-N 0.000 description 2
- 238000001943 fluorescence-activated cell sorting Methods 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 229960002442 glucosamine Drugs 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
- 239000008187 granular material Substances 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 238000001631 haemodialysis Methods 0.000 description 2
- GGXMRPUKBWXVHE-MIHLVHIWSA-N halometasone Chemical compound C1([C@@H](F)C2)=CC(=O)C(Cl)=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]2(C)C[C@@H]1O GGXMRPUKBWXVHE-MIHLVHIWSA-N 0.000 description 2
- 229960002475 halometasone Drugs 0.000 description 2
- 210000002216 heart Anatomy 0.000 description 2
- 230000000322 hemodialysis Effects 0.000 description 2
- NDJKXXJCMXVBJW-UHFFFAOYSA-N heptadecane Chemical compound CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 description 2
- 125000004474 heteroalkylene group Chemical group 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- CYWFCPPBTWOZSF-UHFFFAOYSA-N ibufenac Chemical compound CC(C)CC1=CC=C(CC(O)=O)C=C1 CYWFCPPBTWOZSF-UHFFFAOYSA-N 0.000 description 2
- 229950009183 ibufenac Drugs 0.000 description 2
- 230000028993 immune response Effects 0.000 description 2
- 229960003444 immunosuppressant agent Drugs 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 208000028867 ischemia Diseases 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 210000002510 keratinocyte Anatomy 0.000 description 2
- 239000000787 lecithin Substances 0.000 description 2
- 235000010445 lecithin Nutrition 0.000 description 2
- 229940067606 lecithin Drugs 0.000 description 2
- 239000002523 lectin Substances 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 150000002617 leukotrienes Chemical class 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 244000144972 livestock Species 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- RMGJCSHZTFKPNO-UHFFFAOYSA-M magnesium;ethene;bromide Chemical compound [Mg+2].[Br-].[CH-]=C RMGJCSHZTFKPNO-UHFFFAOYSA-M 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 description 2
- 210000004379 membrane Anatomy 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 229960001428 mercaptopurine Drugs 0.000 description 2
- 239000002207 metabolite Substances 0.000 description 2
- VJOKXLBQCKCWLV-UHFFFAOYSA-N methyl 2-chloropyrimidine-5-carboxylate Chemical compound COC(=O)C1=CN=C(Cl)N=C1 VJOKXLBQCKCWLV-UHFFFAOYSA-N 0.000 description 2
- 229960004584 methylprednisolone Drugs 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 229960002744 mometasone furoate Drugs 0.000 description 2
- WOFMFGQZHJDGCX-ZULDAHANSA-N mometasone furoate Chemical compound O([C@]1([C@@]2(C)C[C@H](O)[C@]3(Cl)[C@@]4(C)C=CC(=O)C=C4CC[C@H]3[C@@H]2C[C@H]1C)C(=O)CCl)C(=O)C1=CC=CO1 WOFMFGQZHJDGCX-ZULDAHANSA-N 0.000 description 2
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 2
- RTGDFNSFWBGLEC-SYZQJQIISA-N mycophenolate mofetil Chemical compound COC1=C(C)C=2COC(=O)C=2C(O)=C1C\C=C(/C)CCC(=O)OCCN1CCOCC1 RTGDFNSFWBGLEC-SYZQJQIISA-N 0.000 description 2
- 229960004866 mycophenolate mofetil Drugs 0.000 description 2
- 229950007221 nedaplatin Drugs 0.000 description 2
- 230000004770 neurodegeneration Effects 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000000346 nonvolatile oil Substances 0.000 description 2
- 229960003347 obinutuzumab Drugs 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 2
- 229960001592 paclitaxel Drugs 0.000 description 2
- 239000004031 partial agonist Substances 0.000 description 2
- 230000001717 pathogenic effect Effects 0.000 description 2
- 229960002340 pentostatin Drugs 0.000 description 2
- FPVKHBSQESCIEP-JQCXWYLXSA-N pentostatin Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(N=CNC[C@H]2O)=C2N=C1 FPVKHBSQESCIEP-JQCXWYLXSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 150000003904 phospholipids Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229950010765 pivalate Drugs 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000747 poly(lactic acid) Polymers 0.000 description 2
- 239000004633 polyglycolic acid Substances 0.000 description 2
- 239000004626 polylactic acid Substances 0.000 description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920006324 polyoxymethylene Polymers 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229960005205 prednisolone Drugs 0.000 description 2
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 2
- 230000000770 proinflammatory effect Effects 0.000 description 2
- 238000011321 prophylaxis Methods 0.000 description 2
- 229940090181 propyl acetate Drugs 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
- 230000006824 pyrimidine synthesis Effects 0.000 description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 description 2
- 201000008158 rapidly progressive glomerulonephritis Diseases 0.000 description 2
- 238000011552 rat model Methods 0.000 description 2
- 239000002151 riboflavin Substances 0.000 description 2
- 229960004641 rituximab Drugs 0.000 description 2
- RZJQGNCSTQAWON-UHFFFAOYSA-N rofecoxib Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)C(=O)OC1 RZJQGNCSTQAWON-UHFFFAOYSA-N 0.000 description 2
- 229960002052 salbutamol Drugs 0.000 description 2
- 229960004017 salmeterol Drugs 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 229960002930 sirolimus Drugs 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 150000003431 steroids Chemical class 0.000 description 2
- 229960001052 streptozocin Drugs 0.000 description 2
- ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 229960001603 tamoxifen Drugs 0.000 description 2
- 230000008685 targeting Effects 0.000 description 2
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 2
- 206010043207 temporal arteritis Diseases 0.000 description 2
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
- DHQSSOMDHCLBEX-UHFFFAOYSA-N tert-butyl 2-(2,6-diethylphenyl)-3-(5-fluoro-7-methoxycarbonyl-1H-indol-4-yl)-6,7-dihydro-4H-pyrazolo[4,3-c]pyridine-5-carboxylate Chemical compound C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CN(CC2)C(=O)OC(C)(C)C)=C1C1=C2C=CNC2=C(C=C1F)C(=O)OC DHQSSOMDHCLBEX-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 2
- 229960003087 tioguanine Drugs 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 230000000699 topical effect Effects 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
- 238000011269 treatment regimen Methods 0.000 description 2
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 2
- 229960002117 triamcinolone acetonide Drugs 0.000 description 2
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 229910052722 tritium Inorganic materials 0.000 description 2
- 229940070710 valerate Drugs 0.000 description 2
- 230000002792 vascular Effects 0.000 description 2
- 230000008728 vascular permeability Effects 0.000 description 2
- 230000003156 vasculitic effect Effects 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- MWLSOWXNZPKENC-SSDOTTSWSA-N zileuton Chemical compound C1=CC=C2SC([C@H](N(O)C(N)=O)C)=CC2=C1 MWLSOWXNZPKENC-SSDOTTSWSA-N 0.000 description 2
- 229960005332 zileuton Drugs 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 description 1
- GQKQMDUOOZVZFD-UHFFFAOYSA-N (2,6-dimethylphenyl)hydrazine;hydron;chloride Chemical compound [Cl-].CC1=CC=CC(C)=C1N[NH3+] GQKQMDUOOZVZFD-UHFFFAOYSA-N 0.000 description 1
- YVQSSVXSNUVPRH-UHFFFAOYSA-N (2-chloropyrimidin-5-yl)-pyrrolidin-1-ylmethanone Chemical compound Clc1ncc(cn1)C(=O)N1CCCC1 YVQSSVXSNUVPRH-UHFFFAOYSA-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
- RJMIEHBSYVWVIN-LLVKDONJSA-N (2r)-2-[4-(3-oxo-1h-isoindol-2-yl)phenyl]propanoic acid Chemical compound C1=CC([C@H](C(O)=O)C)=CC=C1N1C(=O)C2=CC=CC=C2C1 RJMIEHBSYVWVIN-LLVKDONJSA-N 0.000 description 1
- ZEYYDOLCHFETHQ-JOCHJYFZSA-N (2r)-2-cyclopentyl-2-[4-(quinolin-2-ylmethoxy)phenyl]acetic acid Chemical compound C1([C@@H](C(=O)O)C=2C=CC(OCC=3N=C4C=CC=CC4=CC=3)=CC=2)CCCC1 ZEYYDOLCHFETHQ-JOCHJYFZSA-N 0.000 description 1
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- RDJGLLICXDHJDY-NSHDSACASA-N (2s)-2-(3-phenoxyphenyl)propanoic acid Chemical compound OC(=O)[C@@H](C)C1=CC=CC(OC=2C=CC=CC=2)=C1 RDJGLLICXDHJDY-NSHDSACASA-N 0.000 description 1
- GUHPRPJDBZHYCJ-SECBINFHSA-N (2s)-2-(5-benzoylthiophen-2-yl)propanoic acid Chemical compound S1C([C@H](C(O)=O)C)=CC=C1C(=O)C1=CC=CC=C1 GUHPRPJDBZHYCJ-SECBINFHSA-N 0.000 description 1
- MDKGKXOCJGEUJW-VIFPVBQESA-N (2s)-2-[4-(thiophene-2-carbonyl)phenyl]propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C(=O)C1=CC=CS1 MDKGKXOCJGEUJW-VIFPVBQESA-N 0.000 description 1
- PZIFPMYXXCAOCC-JWQCQUIFSA-N (2s,3r)-3-(2-carboxyethylsulfanyl)-2-hydroxy-3-[2-(8-phenyloctyl)phenyl]propanoic acid Chemical compound OC(=O)CCS[C@@H]([C@@H](O)C(O)=O)C1=CC=CC=C1CCCCCCCCC1=CC=CC=C1 PZIFPMYXXCAOCC-JWQCQUIFSA-N 0.000 description 1
- OQANPHBRHBJGNZ-FYJGNVAPSA-N (3e)-6-oxo-3-[[4-(pyridin-2-ylsulfamoyl)phenyl]hydrazinylidene]cyclohexa-1,4-diene-1-carboxylic acid Chemical compound C1=CC(=O)C(C(=O)O)=C\C1=N\NC1=CC=C(S(=O)(=O)NC=2N=CC=CC=2)C=C1 OQANPHBRHBJGNZ-FYJGNVAPSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- 125000000196 1,4-pentadienyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])=C([H])[H] 0.000 description 1
- YHIIJNLSGULWAA-UHFFFAOYSA-N 1,4-thiazinane 1-oxide Chemical compound O=S1CCNCC1 YHIIJNLSGULWAA-UHFFFAOYSA-N 0.000 description 1
- DHSGXAGGBXJPEL-UHFFFAOYSA-N 1-bromo-2-fluoro-4-methoxy-5-nitrobenzene Chemical compound COC1=CC(F)=C(Br)C=C1[N+]([O-])=O DHSGXAGGBXJPEL-UHFFFAOYSA-N 0.000 description 1
- MTTNTJRJOFVWSY-UHFFFAOYSA-N 1-bromo-2-fluoro-4-methyl-5-nitrobenzene Chemical compound CC1=CC(F)=C(Br)C=C1[N+]([O-])=O MTTNTJRJOFVWSY-UHFFFAOYSA-N 0.000 description 1
- BTUGGGLMQBJCBN-UHFFFAOYSA-N 1-iodo-2-methylpropane Chemical compound CC(C)CI BTUGGGLMQBJCBN-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- JZVCMOJSPCGLTC-UHFFFAOYSA-N 1020717-99-0 Chemical compound OC(=O)C1=CC(F)=C(Br)C=C1[N+]([O-])=O JZVCMOJSPCGLTC-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- OKRROXQXGNEUSS-UHFFFAOYSA-N 1h-imidazol-1-ium-1-carboxylate Chemical compound OC(=O)N1C=CN=C1 OKRROXQXGNEUSS-UHFFFAOYSA-N 0.000 description 1
- USJUQEVUEBCLLR-UHFFFAOYSA-N 1h-indol-4-ylboronic acid Chemical compound OB(O)C1=CC=CC2=C1C=CN2 USJUQEVUEBCLLR-UHFFFAOYSA-N 0.000 description 1
- VHADYSUJZAPXOW-UHFFFAOYSA-N 1h-indol-5-ylboronic acid Chemical compound OB(O)C1=CC=C2NC=CC2=C1 VHADYSUJZAPXOW-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- OGVLEPMNNPZAPS-UHFFFAOYSA-N 2,3-difluoropyridine Chemical compound FC1=CC=CN=C1F OGVLEPMNNPZAPS-UHFFFAOYSA-N 0.000 description 1
- FOYHNROGBXVLLX-UHFFFAOYSA-N 2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1N FOYHNROGBXVLLX-UHFFFAOYSA-N 0.000 description 1
- KLIVRBFRQSOGQI-UHFFFAOYSA-N 2-(11-oxo-6h-benzo[c][1]benzothiepin-3-yl)acetic acid Chemical compound S1CC2=CC=CC=C2C(=O)C2=CC=C(CC(=O)O)C=C12 KLIVRBFRQSOGQI-UHFFFAOYSA-N 0.000 description 1
- KORYPFNDGBUNLL-UHFFFAOYSA-N 2-(2,6-diethylphenyl)-5-[3-fluoro-5-(trifluoromethyl)pyridin-2-yl]-3-(7-methoxy-1H-indol-4-yl)-6,7-dihydro-4H-pyrazolo[4,3-c]pyridine Chemical compound C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CN(CC2)C2=NC=C(C=C2F)C(F)(F)F)=C1C1=C2C=CNC2=C(C=C1)OC KORYPFNDGBUNLL-UHFFFAOYSA-N 0.000 description 1
- MYQXHLQMZLTSDB-UHFFFAOYSA-N 2-(2-ethyl-2,3-dihydro-1-benzofuran-5-yl)acetic acid Chemical compound OC(=O)CC1=CC=C2OC(CC)CC2=C1 MYQXHLQMZLTSDB-UHFFFAOYSA-N 0.000 description 1
- DCXHLPGLBYHNMU-UHFFFAOYSA-N 2-[1-(4-azidobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(N=[N+]=[N-])C=C1 DCXHLPGLBYHNMU-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- APBSKHYXXKHJFK-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)-1,3-thiazol-4-yl]acetic acid Chemical compound OC(=O)CC1=CSC(C=2C=CC(Cl)=CC=2)=N1 APBSKHYXXKHJFK-UHFFFAOYSA-N 0.000 description 1
- TYCOFFBAZNSQOJ-UHFFFAOYSA-N 2-[4-(3-fluorophenyl)phenyl]propanoic acid Chemical compound C1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC(F)=C1 TYCOFFBAZNSQOJ-UHFFFAOYSA-N 0.000 description 1
- JIEKMACRVQTPRC-UHFFFAOYSA-N 2-[4-(4-chlorophenyl)-2-phenyl-5-thiazolyl]acetic acid Chemical compound OC(=O)CC=1SC(C=2C=CC=CC=2)=NC=1C1=CC=C(Cl)C=C1 JIEKMACRVQTPRC-UHFFFAOYSA-N 0.000 description 1
- WGDADRBTCPGSDG-UHFFFAOYSA-N 2-[[4,5-bis(4-chlorophenyl)-1,3-oxazol-2-yl]sulfanyl]propanoic acid Chemical compound O1C(SC(C)C(O)=O)=NC(C=2C=CC(Cl)=CC=2)=C1C1=CC=C(Cl)C=C1 WGDADRBTCPGSDG-UHFFFAOYSA-N 0.000 description 1
- XKSAJZSJKURQRX-UHFFFAOYSA-N 2-acetyloxy-5-(4-fluorophenyl)benzoic acid Chemical compound C1=C(C(O)=O)C(OC(=O)C)=CC=C1C1=CC=C(F)C=C1 XKSAJZSJKURQRX-UHFFFAOYSA-N 0.000 description 1
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 1
- BZUUVQCSPHPUQA-UHFFFAOYSA-N 2-bromo-5-chloropyridine Chemical compound ClC1=CC=C(Br)N=C1 BZUUVQCSPHPUQA-UHFFFAOYSA-N 0.000 description 1
- JZXOFYWUUZOAAN-UHFFFAOYSA-N 2-chloro-5-methylpyrimidine-4-carboxylic acid Chemical compound CC1=CN=C(Cl)N=C1C(O)=O JZXOFYWUUZOAAN-UHFFFAOYSA-N 0.000 description 1
- QFLAUXDLHKYUIA-UHFFFAOYSA-N 2-chloro-5-propan-2-ylpyrimidine Chemical compound CC(C)C1=CN=C(Cl)N=C1 QFLAUXDLHKYUIA-UHFFFAOYSA-N 0.000 description 1
- DUCXUPKLVVSJKA-UHFFFAOYSA-N 2-chloropyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=C(Cl)N=C1 DUCXUPKLVVSJKA-UHFFFAOYSA-N 0.000 description 1
- CPCVDCYAKMUIKW-UHFFFAOYSA-N 2-cyclopropylpyrimidine Chemical compound C1CC1C1=NC=CC=N1 CPCVDCYAKMUIKW-UHFFFAOYSA-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
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 1
- MGOLNIXAPIAKFM-UHFFFAOYSA-N 2-isocyanato-2-methylpropane Chemical compound CC(C)(C)N=C=O MGOLNIXAPIAKFM-UHFFFAOYSA-N 0.000 description 1
- WFECKOIIFLSNQE-UHFFFAOYSA-N 2-methyl-6-(2-methylpropoxy)aniline Chemical compound CC(C)COC1=CC=CC(C)=C1N WFECKOIIFLSNQE-UHFFFAOYSA-N 0.000 description 1
- CTRPRMNBTVRDFH-UHFFFAOYSA-N 2-n-methyl-1,3,5-triazine-2,4,6-triamine Chemical compound CNC1=NC(N)=NC(N)=N1 CTRPRMNBTVRDFH-UHFFFAOYSA-N 0.000 description 1
- ILYSAKHOYBPSPC-UHFFFAOYSA-N 2-phenylbenzoic acid Chemical class OC(=O)C1=CC=CC=C1C1=CC=CC=C1 ILYSAKHOYBPSPC-UHFFFAOYSA-N 0.000 description 1
- PFYPDUUXDADWKC-UHFFFAOYSA-N 2-propan-2-ylpyridine Chemical compound CC(C)C1=CC=CC=N1 PFYPDUUXDADWKC-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-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
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- QIORDSKCCHRSSD-UHFFFAOYSA-N 3-methyl-2-nitrophenol Chemical compound CC1=CC=CC(O)=C1[N+]([O-])=O QIORDSKCCHRSSD-UHFFFAOYSA-N 0.000 description 1
- JVQIKJMSUIMUDI-UHFFFAOYSA-N 3-pyrroline Chemical compound C1NCC=C1 JVQIKJMSUIMUDI-UHFFFAOYSA-N 0.000 description 1
- AOJJSUZBOXZQNB-VTZDEGQISA-N 4'-epidoxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-VTZDEGQISA-N 0.000 description 1
- MHJBZVSGOZTKRH-IZHYLOQSSA-N 4-Hydroxy-N-desmethyltamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCNC)=CC=1)/C1=CC=C(O)C=C1 MHJBZVSGOZTKRH-IZHYLOQSSA-N 0.000 description 1
- DODQJNMQWMSYGS-QPLCGJKRSA-N 4-[(z)-1-[4-[2-(dimethylamino)ethoxy]phenyl]-1-phenylbut-1-en-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 DODQJNMQWMSYGS-QPLCGJKRSA-N 0.000 description 1
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical group C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 1
- SCQYUKGOAZBRQL-UHFFFAOYSA-N 4-bromo-2-chloro-6-nitrophenol Chemical compound OC1=C(Cl)C=C(Br)C=C1[N+]([O-])=O SCQYUKGOAZBRQL-UHFFFAOYSA-N 0.000 description 1
- UXLRNUCHBXKRBL-UHFFFAOYSA-N 4-bromo-2-fluoro-6-nitroaniline Chemical compound NC1=C(F)C=C(Br)C=C1[N+]([O-])=O UXLRNUCHBXKRBL-UHFFFAOYSA-N 0.000 description 1
- ZMSFGDZCAYKXOE-UHFFFAOYSA-N 4-bromo-5-fluoro-2-nitrophenol Chemical compound OC1=CC(F)=C(Br)C=C1[N+]([O-])=O ZMSFGDZCAYKXOE-UHFFFAOYSA-N 0.000 description 1
- SIKUFDVMQXXDET-UHFFFAOYSA-N 4-bromo-7-methoxy-1h-indazole Chemical compound COC1=CC=C(Br)C2=C1NN=C2 SIKUFDVMQXXDET-UHFFFAOYSA-N 0.000 description 1
- WCEJDYPAEFIBCD-UHFFFAOYSA-N 4-bromo-7-methoxy-1h-indole Chemical compound COC1=CC=C(Br)C2=C1NC=C2 WCEJDYPAEFIBCD-UHFFFAOYSA-N 0.000 description 1
- FEMJIOSKNKIMBM-UHFFFAOYSA-N 4-bromo-7-methyl-1h-indole Chemical compound CC1=CC=C(Br)C2=C1NC=C2 FEMJIOSKNKIMBM-UHFFFAOYSA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- SYCHUQUJURZQMO-UHFFFAOYSA-N 4-hydroxy-2-methyl-1,1-dioxo-n-(1,3-thiazol-2-yl)-1$l^{6},2-benzothiazine-3-carboxamide Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=NC=CS1 SYCHUQUJURZQMO-UHFFFAOYSA-N 0.000 description 1
- LNOJNUZUBPSRTB-UHFFFAOYSA-N 5-(3-chloro-5-fluoropyridin-2-yl)-3-(7-chloro-1H-indol-4-yl)-2-(2,6-diethylphenyl)-6,7-dihydro-4H-pyrazolo[4,3-c]pyridine Chemical compound ClC=1C=CC(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1Cl)F)C1=C(C=CC=C1CC)CC LNOJNUZUBPSRTB-UHFFFAOYSA-N 0.000 description 1
- LSLYOANBFKQKPT-DIFFPNOSSA-N 5-[(1r)-1-hydroxy-2-[[(2r)-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]benzene-1,3-diol Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(O)C=C(O)C=1)C1=CC=C(O)C=C1 LSLYOANBFKQKPT-DIFFPNOSSA-N 0.000 description 1
- CDOQKISJPOWBKC-UHFFFAOYSA-N 5-bromo-1,3-difluoro-2-methoxybenzene Chemical compound COC1=C(F)C=C(Br)C=C1F CDOQKISJPOWBKC-UHFFFAOYSA-N 0.000 description 1
- KQMXGSGRIHBQGJ-UHFFFAOYSA-N 5-bromo-1-chloro-2-methyl-3-nitrobenzene Chemical compound CC1=C(Cl)C=C(Br)C=C1[N+]([O-])=O KQMXGSGRIHBQGJ-UHFFFAOYSA-N 0.000 description 1
- CVCAYLYLJKBSNV-UHFFFAOYSA-N 5-bromo-1-fluoro-2-methoxy-3-nitrobenzene Chemical compound COC1=C(F)C=C(Br)C=C1[N+]([O-])=O CVCAYLYLJKBSNV-UHFFFAOYSA-N 0.000 description 1
- AFFZHZYWAUZGCC-UHFFFAOYSA-N 5-bromo-2-chloro-1-fluoro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Br)=CC(F)=C1Cl AFFZHZYWAUZGCC-UHFFFAOYSA-N 0.000 description 1
- MYUQKYGWKHTRPG-UHFFFAOYSA-N 5-bromo-2-fluoropyridine Chemical compound FC1=CC=C(Br)C=N1 MYUQKYGWKHTRPG-UHFFFAOYSA-N 0.000 description 1
- UGJWQTANPAEJOT-UHFFFAOYSA-N 5-cyclopropylpyrimidine Chemical compound C1CC1C1=CN=CN=C1 UGJWQTANPAEJOT-UHFFFAOYSA-N 0.000 description 1
- IXJCHVMUTFCRBH-SDUHDBOFSA-N 7-[(1r,2s,3e,5z)-10-(4-acetyl-3-hydroxy-2-propylphenoxy)-1-hydroxy-1-[3-(trifluoromethyl)phenyl]deca-3,5-dien-2-yl]sulfanyl-4-oxochromene-2-carboxylic acid Chemical compound CCCC1=C(O)C(C(C)=O)=CC=C1OCCCC\C=C/C=C/[C@@H]([C@H](O)C=1C=C(C=CC=1)C(F)(F)F)SC1=CC=C2C(=O)C=C(C(O)=O)OC2=C1 IXJCHVMUTFCRBH-SDUHDBOFSA-N 0.000 description 1
- XONKJZDHGCMRRF-UHFFFAOYSA-N 7-fluoro-1h-indole Chemical compound FC1=CC=CC2=C1NC=C2 XONKJZDHGCMRRF-UHFFFAOYSA-N 0.000 description 1
- AZDGIPLCIYTFRY-UHFFFAOYSA-N 7-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-indole Chemical compound C1=2C=CNC=2C(OC)=CC=C1B1OC(C)(C)C(C)(C)O1 AZDGIPLCIYTFRY-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 206010001233 Adenoma benign Diseases 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 235000003911 Arachis Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- WYBVBIHNJWOLCJ-IUCAKERBSA-N Arg-Leu Chemical compound CC(C)C[C@@H](C(O)=O)NC(=O)[C@@H](N)CCCNC(N)=N WYBVBIHNJWOLCJ-IUCAKERBSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 229930003347 Atropine Natural products 0.000 description 1
- XHVAWZZCDCWGBK-WYRLRVFGSA-M Aurothioglucose Chemical compound OC[C@H]1O[C@H](S[Au])[C@H](O)[C@@H](O)[C@@H]1O XHVAWZZCDCWGBK-WYRLRVFGSA-M 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- 208000009137 Behcet syndrome Diseases 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- URGAPSVLEDDYJT-UHFFFAOYSA-N BrC1=C2C=CNC2=C(C(=C1)F)C(=O)OC Chemical compound BrC1=C2C=CNC2=C(C(=C1)F)C(=O)OC URGAPSVLEDDYJT-UHFFFAOYSA-N 0.000 description 1
- BNJXCORZLBRWCN-UHFFFAOYSA-N BrC1=C2C=CNC2=C(C=C1F)C(=O)OC Chemical compound BrC1=C2C=CNC2=C(C=C1F)C(=O)OC BNJXCORZLBRWCN-UHFFFAOYSA-N 0.000 description 1
- ILHDFXCFLXFAKT-UHFFFAOYSA-N BrC1=NC=C(C2=C1C=CN2C(=O)OC(C)(C)C)Cl Chemical compound BrC1=NC=C(C2=C1C=CN2C(=O)OC(C)(C)C)Cl ILHDFXCFLXFAKT-UHFFFAOYSA-N 0.000 description 1
- FRXMFTCORIWOBP-UHFFFAOYSA-N BrC=1N(N=C2C=1CN(CC2)C(=O)OC(C)(C)C)C1=C(C=CC=C1C)C Chemical class BrC=1N(N=C2C=1CN(CC2)C(=O)OC(C)(C)C)C1=C(C=CC=C1C)C FRXMFTCORIWOBP-UHFFFAOYSA-N 0.000 description 1
- GMJDLBYVJLACIO-UHFFFAOYSA-N BrC=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1Cl)C(F)(F)F)C1=C(C=CC=C1CC)CC Chemical compound BrC=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1Cl)C(F)(F)F)C1=C(C=CC=C1CC)CC GMJDLBYVJLACIO-UHFFFAOYSA-N 0.000 description 1
- VQUDVNLXRASOLE-UHFFFAOYSA-N BrC=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1Cl)Cl)C1=C(C=CC=C1CC)CC Chemical compound BrC=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1Cl)Cl)C1=C(C=CC=C1CC)CC VQUDVNLXRASOLE-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 206010006482 Bronchospasm Diseases 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- KFESBKWDDLGKRJ-UHFFFAOYSA-N C(C(C)C)ONC1=CC=CC=C1C Chemical compound C(C(C)C)ONC1=CC=CC=C1C KFESBKWDDLGKRJ-UHFFFAOYSA-N 0.000 description 1
- RSQNXEXRINBLFV-UHFFFAOYSA-N C(C)(C)(C)C1=NCCC=2C1=C(N(N2)C2=C(C=CC=C2C)OCC(C)C)C=2C=C1C=CNC1=CC2 Chemical compound C(C)(C)(C)C1=NCCC=2C1=C(N(N2)C2=C(C=CC=C2C)OCC(C)C)C=2C=C1C=CNC1=CC2 RSQNXEXRINBLFV-UHFFFAOYSA-N 0.000 description 1
- ZJQMCFNUTMTWKZ-UHFFFAOYSA-N C(C)(C)(C)OC(=O)N1CC=2C(CC1)=NN(C=2C=1C=C2C=CNC2=CC=1)C1=C(C=CC=C1C)OCC(C)C Chemical compound C(C)(C)(C)OC(=O)N1CC=2C(CC1)=NN(C=2C=1C=C2C=CNC2=CC=1)C1=C(C=CC=C1C)OCC(C)C ZJQMCFNUTMTWKZ-UHFFFAOYSA-N 0.000 description 1
- RXQRQTQTAUZCEJ-UHFFFAOYSA-N C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CN(CC2)C(=O)OC(C)(C)C)=C1C1=C2C=CNC2=C(C(=C1)F)F Chemical compound C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CN(CC2)C(=O)OC(C)(C)C)=C1C1=C2C=CNC2=C(C(=C1)F)F RXQRQTQTAUZCEJ-UHFFFAOYSA-N 0.000 description 1
- OBVYZKJYPDGHLX-UHFFFAOYSA-N C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CN(CC2)C(=O)OC(C)(C)C)=C1C1=C2C=CNC2=C(C=C1F)CO Chemical compound C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CN(CC2)C(=O)OC(C)(C)C)=C1C1=C2C=CNC2=C(C=C1F)CO OBVYZKJYPDGHLX-UHFFFAOYSA-N 0.000 description 1
- WPFOMTCITOFHBG-UHFFFAOYSA-N C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CN(CC2)C(=O)OC(C)(C)C)=C1C1=C2C=CNC2=C(C=C1F)OC Chemical compound C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CN(CC2)C(=O)OC(C)(C)C)=C1C1=C2C=CNC2=C(C=C1F)OC WPFOMTCITOFHBG-UHFFFAOYSA-N 0.000 description 1
- BGBIHHMLYLOSDB-UHFFFAOYSA-N C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CN(CC2)C2=NC=C(C=C2F)C(F)(F)F)=C1C1=C2C=CNC2=C(C=C1)C(=O)O Chemical compound C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CN(CC2)C2=NC=C(C=C2F)C(F)(F)F)=C1C1=C2C=CNC2=C(C=C1)C(=O)O BGBIHHMLYLOSDB-UHFFFAOYSA-N 0.000 description 1
- BUJZFTWQAQXFJD-UHFFFAOYSA-N C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CN(CC2)C2=NC=C(C=C2F)C(F)(F)F)=C1C1=C2C=CNC2=C(C=C1)CO Chemical compound C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CN(CC2)C2=NC=C(C=C2F)C(F)(F)F)=C1C1=C2C=CNC2=C(C=C1)CO BUJZFTWQAQXFJD-UHFFFAOYSA-N 0.000 description 1
- JTQQZIAFEOCZEQ-UHFFFAOYSA-N C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CN(CC2)C2=NC=C(C=C2F)C(F)(F)F)=C1C1=C2C=CNC2=C(C=C1)F Chemical compound C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CN(CC2)C2=NC=C(C=C2F)C(F)(F)F)=C1C1=C2C=CNC2=C(C=C1)F JTQQZIAFEOCZEQ-UHFFFAOYSA-N 0.000 description 1
- GYSSDAJHSILYDJ-UHFFFAOYSA-N C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CN(CC2)C2=NC=C(C=C2F)C(F)(F)F)=C1C1=C2C=CNC2=C(C=C1F)C Chemical compound C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CN(CC2)C2=NC=C(C=C2F)C(F)(F)F)=C1C1=C2C=CNC2=C(C=C1F)C GYSSDAJHSILYDJ-UHFFFAOYSA-N 0.000 description 1
- UVLUAEKAFOAUPP-UHFFFAOYSA-N C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CN(CC2)C2=NC=C(C=C2F)C(F)(F)F)=C1C1=C2C=CNC2=C(C=C1F)OC Chemical compound C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CN(CC2)C2=NC=C(C=C2F)C(F)(F)F)=C1C1=C2C=CNC2=C(C=C1F)OC UVLUAEKAFOAUPP-UHFFFAOYSA-N 0.000 description 1
- ORWCQIGRUFDAKI-UHFFFAOYSA-N C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CN(CC2)C2=NC=C(C=C2F)C(F)(F)F)=C1C1=C2C=NNC2=C(C(=C1)F)OC Chemical compound C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CN(CC2)C2=NC=C(C=C2F)C(F)(F)F)=C1C1=C2C=NNC2=C(C(=C1)F)OC ORWCQIGRUFDAKI-UHFFFAOYSA-N 0.000 description 1
- FFMOLNIIIYECSQ-UHFFFAOYSA-N C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CN(CC2)C2=NC=C(C=N2)C(C)C)=C1C1=C2C=CNC2=C(C=C1)F Chemical compound C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CN(CC2)C2=NC=C(C=N2)C(C)C)=C1C1=C2C=CNC2=C(C=C1)F FFMOLNIIIYECSQ-UHFFFAOYSA-N 0.000 description 1
- WLRIQVVCKXDBMM-UHFFFAOYSA-N C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CN(CC2)C2=NC=C(C=N2)C(F)(F)F)=C1C1=C2C=CNC2=C(C(=C1)F)F Chemical compound C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CN(CC2)C2=NC=C(C=N2)C(F)(F)F)=C1C1=C2C=CNC2=C(C(=C1)F)F WLRIQVVCKXDBMM-UHFFFAOYSA-N 0.000 description 1
- ANHDGHAGHHSOIO-UHFFFAOYSA-N C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CN(CC2)C2=NC=C(C=N2)C(F)(F)F)=C1C1=C2C=CNC2=C(C=C1F)CO Chemical compound C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CN(CC2)C2=NC=C(C=N2)C(F)(F)F)=C1C1=C2C=CNC2=C(C=C1F)CO ANHDGHAGHHSOIO-UHFFFAOYSA-N 0.000 description 1
- ZHXYKWYIXPOMSH-UHFFFAOYSA-N C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CNC(C2)C2=NC=C(C=N2)C(F)(F)F)=C1C1=C2C=CNC2=C(C=C1F)CO Chemical compound C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CNC(C2)C2=NC=C(C=N2)C(F)(F)F)=C1C1=C2C=CNC2=C(C=C1F)CO ZHXYKWYIXPOMSH-UHFFFAOYSA-N 0.000 description 1
- 102100031151 C-C chemokine receptor type 2 Human genes 0.000 description 1
- 101710149815 C-C chemokine receptor type 2 Proteins 0.000 description 1
- 102100024167 C-C chemokine receptor type 3 Human genes 0.000 description 1
- 101710149862 C-C chemokine receptor type 3 Proteins 0.000 description 1
- 102100037853 C-C chemokine receptor type 4 Human genes 0.000 description 1
- 101710149863 C-C chemokine receptor type 4 Proteins 0.000 description 1
- 102100036301 C-C chemokine receptor type 7 Human genes 0.000 description 1
- 108010074051 C-Reactive Protein Proteins 0.000 description 1
- 102100028989 C-X-C chemokine receptor type 2 Human genes 0.000 description 1
- 102100028990 C-X-C chemokine receptor type 3 Human genes 0.000 description 1
- 102100025618 C-X-C chemokine receptor type 6 Human genes 0.000 description 1
- 102100032752 C-reactive protein Human genes 0.000 description 1
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 description 1
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 description 1
- CJNJKFMWKDJXBT-UHFFFAOYSA-N CC(C)(C)OC(=O)N1C=CC2=CN=CC2=C1 Chemical compound CC(C)(C)OC(=O)N1C=CC2=CN=CC2=C1 CJNJKFMWKDJXBT-UHFFFAOYSA-N 0.000 description 1
- KKGBXIHHIDLMRO-UHFFFAOYSA-N CC1=C(C(=CC=C1)C)N1N=C2C(CN(CC2)C2=NC=C(C=C2F)C(F)(F)F)=C1C1=C2C=CNC2=C(C=C1)F Chemical compound CC1=C(C(=CC=C1)C)N1N=C2C(CN(CC2)C2=NC=C(C=C2F)C(F)(F)F)=C1C1=C2C=CNC2=C(C=C1)F KKGBXIHHIDLMRO-UHFFFAOYSA-N 0.000 description 1
- JSVYMSKXTMLVON-UHFFFAOYSA-N CC1=C(C(=CC=C1)C)N1N=C2C(CN(CC2)C2=NC=C(C=N2)C(F)(F)F)=C1C1=C2C=CNC2=C(C(=C1)F)C Chemical compound CC1=C(C(=CC=C1)C)N1N=C2C(CN(CC2)C2=NC=C(C=N2)C(F)(F)F)=C1C1=C2C=CNC2=C(C(=C1)F)C JSVYMSKXTMLVON-UHFFFAOYSA-N 0.000 description 1
- OMHRXPSKTGARML-UHFFFAOYSA-N CC1=C(C(=CC=C1)C)N1N=C2C(CNC(C2)C2=NC=C(C=N2)C(F)(F)F)=C1C1=C2C=CNC2=C(C=C1F)CO Chemical compound CC1=C(C(=CC=C1)C)N1N=C2C(CNC(C2)C2=NC=C(C=N2)C(F)(F)F)=C1C1=C2C=CNC2=C(C=C1F)CO OMHRXPSKTGARML-UHFFFAOYSA-N 0.000 description 1
- VRQSKIAPKRVFMO-UHFFFAOYSA-N CC=1C=CC(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1)C(C)C)C1=C(C=CC=C1CC)CC Chemical compound CC=1C=CC(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1)C(C)C)C1=C(C=CC=C1CC)CC VRQSKIAPKRVFMO-UHFFFAOYSA-N 0.000 description 1
- FSBKWSLKAJLIPG-UHFFFAOYSA-N CCc1cccc(CC)c1-n1nc2CCN(Cc2c1Br)C(O)=O Chemical compound CCc1cccc(CC)c1-n1nc2CCN(Cc2c1Br)C(O)=O FSBKWSLKAJLIPG-UHFFFAOYSA-N 0.000 description 1
- KICZVBFIYGNORH-UHFFFAOYSA-N COC=1C=CC(=C2C=NNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=N1)C(F)(F)F)C1=C(C=CC=C1CC)CC Chemical compound COC=1C=CC(=C2C=NNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=N1)C(F)(F)F)C1=C(C=CC=C1CC)CC KICZVBFIYGNORH-UHFFFAOYSA-N 0.000 description 1
- 108090000835 CX3C Chemokine Receptor 1 Proteins 0.000 description 1
- 102100039196 CX3C chemokine receptor 1 Human genes 0.000 description 1
- FVLVBPDQNARYJU-XAHDHGMMSA-N C[C@H]1CCC(CC1)NC(=O)N(CCCl)N=O Chemical compound C[C@H]1CCC(CC1)NC(=O)N(CCCl)N=O FVLVBPDQNARYJU-XAHDHGMMSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 1
- ZKLPARSLTMPFCP-UHFFFAOYSA-N Cetirizine Chemical compound C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-UHFFFAOYSA-N 0.000 description 1
- 102000009410 Chemokine receptor Human genes 0.000 description 1
- 108050000299 Chemokine receptor Proteins 0.000 description 1
- 208000017667 Chronic Disease Diseases 0.000 description 1
- XGJVVJCEOOGKFN-UHFFFAOYSA-N Cl.C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CNCC2)=C1 Chemical compound Cl.C(C)C1=C(C(=CC=C1)CC)N1N=C2C(CNCC2)=C1 XGJVVJCEOOGKFN-UHFFFAOYSA-N 0.000 description 1
- CHNPFCRDSHVVEV-UHFFFAOYSA-N Cl.CCc1cccc(CC)c1-n1nc2CCNCc2c1-c1cc(Cl)c(OC)c2[nH]ccc12 Chemical compound Cl.CCc1cccc(CC)c1-n1nc2CCNCc2c1-c1cc(Cl)c(OC)c2[nH]ccc12 CHNPFCRDSHVVEV-UHFFFAOYSA-N 0.000 description 1
- VUYSIOVKEHQSIO-UHFFFAOYSA-N Cl.ClC=1C(=CC(=C2C=CNC=12)C=1N(N=C2C=1CNCC2)C1=C(C=CC=C1CC)CC)F Chemical compound Cl.ClC=1C(=CC(=C2C=CNC=12)C=1N(N=C2C=1CNCC2)C1=C(C=CC=C1CC)CC)F VUYSIOVKEHQSIO-UHFFFAOYSA-N 0.000 description 1
- GMTGUTWZELPTFN-UHFFFAOYSA-N Cl.ClC=1C=C(C(=C2C=CNC=12)C=1N(N=C2C=1CNCC2)C1=C(C=CC=C1C)C)F Chemical compound Cl.ClC=1C=C(C(=C2C=CNC=12)C=1N(N=C2C=1CNCC2)C1=C(C=CC=C1C)C)F GMTGUTWZELPTFN-UHFFFAOYSA-N 0.000 description 1
- BXPJLEMKTCLMCX-UHFFFAOYSA-N ClC1=CC(=C2C=CNC2=C1OC)B1OC(C(O1)(C)C)(C)C Chemical compound ClC1=CC(=C2C=CNC2=C1OC)B1OC(C(O1)(C)C)(C)C BXPJLEMKTCLMCX-UHFFFAOYSA-N 0.000 description 1
- YKZPSAZBOZMQHW-UHFFFAOYSA-N ClC1=CC(=C2C=CNC2=C1OC)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=N1)C(F)(F)F)C1=C(C=CC=C1CC)CC Chemical compound ClC1=CC(=C2C=CNC2=C1OC)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=N1)C(F)(F)F)C1=C(C=CC=C1CC)CC YKZPSAZBOZMQHW-UHFFFAOYSA-N 0.000 description 1
- UEYNEJSYIZJFIN-UHFFFAOYSA-N ClC1=CNC2=C(C=CC(=C12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1F)C(F)(F)F)C1=C(C=CC=C1C)C)F Chemical compound ClC1=CNC2=C(C=CC(=C12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1F)C(F)(F)F)C1=C(C=CC=C1C)C)F UEYNEJSYIZJFIN-UHFFFAOYSA-N 0.000 description 1
- PAHJKEPHNOTKIX-UHFFFAOYSA-N ClC1=CNC2=C(C=CC(=C12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1F)C(F)(F)F)C1=C(C=CC=C1CC)CC)C Chemical compound ClC1=CNC2=C(C=CC(=C12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1F)C(F)(F)F)C1=C(C=CC=C1CC)CC)C PAHJKEPHNOTKIX-UHFFFAOYSA-N 0.000 description 1
- RTBFJFFHQBJERL-UHFFFAOYSA-N ClC1=CNC2=C(C=CC(=C12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1F)C(F)(F)F)C1=C(C=CC=C1CC)CC)F Chemical compound ClC1=CNC2=C(C=CC(=C12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1F)C(F)(F)F)C1=C(C=CC=C1CC)CC)F RTBFJFFHQBJERL-UHFFFAOYSA-N 0.000 description 1
- TXAPSBZNTOZTDS-UHFFFAOYSA-N ClC=1C(=CC(=C2C=CNC=12)B1OC(C(O1)(C)C)(C)C)F Chemical compound ClC=1C(=CC(=C2C=CNC=12)B1OC(C(O1)(C)C)(C)C)F TXAPSBZNTOZTDS-UHFFFAOYSA-N 0.000 description 1
- OSZJLULKUMEZMT-UHFFFAOYSA-N ClC=1C(=CC(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=N1)C(F)(F)F)C1=C(C=CC=C1CC)CC)F Chemical compound ClC=1C(=CC(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=N1)C(F)(F)F)C1=C(C=CC=C1CC)CC)F OSZJLULKUMEZMT-UHFFFAOYSA-N 0.000 description 1
- PRAYKQIIRMYDNH-UHFFFAOYSA-N ClC=1C=C(C(=C2C=CNC=12)B1OC(C(O1)(C)C)(C)C)F Chemical compound ClC=1C=C(C(=C2C=CNC=12)B1OC(C(O1)(C)C)(C)C)F PRAYKQIIRMYDNH-UHFFFAOYSA-N 0.000 description 1
- TXASVEOLVMRMRL-UHFFFAOYSA-N ClC=1C=C(C(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1)C(C)C)C1=C(C=CC=C1CC)CC)F Chemical compound ClC=1C=C(C(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1)C(C)C)C1=C(C=CC=C1CC)CC)F TXASVEOLVMRMRL-UHFFFAOYSA-N 0.000 description 1
- KORPAWLWOLQXSV-UHFFFAOYSA-N ClC=1C=C(C(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1F)C(C)C)C1=C(C=CC=C1C)C)F Chemical compound ClC=1C=C(C(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1F)C(C)C)C1=C(C=CC=C1C)C)F KORPAWLWOLQXSV-UHFFFAOYSA-N 0.000 description 1
- PCBBDKNKBTUXQH-UHFFFAOYSA-N ClC=1C=C(C(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1F)C(C)C)C1=C(C=CC=C1CC)CC)F Chemical compound ClC=1C=C(C(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1F)C(C)C)C1=C(C=CC=C1CC)CC)F PCBBDKNKBTUXQH-UHFFFAOYSA-N 0.000 description 1
- ZHMUFRXRZXLJDP-UHFFFAOYSA-N ClC=1C=C(C(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=N1)C1CC1)C1=C(C=CC=C1CC)CC)F Chemical compound ClC=1C=C(C(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=N1)C1CC1)C1=C(C=CC=C1CC)CC)F ZHMUFRXRZXLJDP-UHFFFAOYSA-N 0.000 description 1
- VWCCNIPOGDQYTG-UHFFFAOYSA-N ClC=1C=CC(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C(=O)NC1=CC=CC=C1)C1=C(C=CC=C1CC)CC Chemical compound ClC=1C=CC(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C(=O)NC1=CC=CC=C1)C1=C(C=CC=C1CC)CC VWCCNIPOGDQYTG-UHFFFAOYSA-N 0.000 description 1
- CSUMPBBDBAYOQJ-UHFFFAOYSA-N ClC=1C=CC(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C(=N1)C(=O)O)C)C1=C(C=CC=C1CC)CC Chemical compound ClC=1C=CC(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C(=N1)C(=O)O)C)C1=C(C=CC=C1CC)CC CSUMPBBDBAYOQJ-UHFFFAOYSA-N 0.000 description 1
- YQADPVABCXRNPJ-UHFFFAOYSA-N ClC=1C=CC(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1)C(F)(F)F)C1=C(C=CC=C1CC)CC Chemical compound ClC=1C=CC(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1)C(F)(F)F)C1=C(C=CC=C1CC)CC YQADPVABCXRNPJ-UHFFFAOYSA-N 0.000 description 1
- GXMREGOXQFHIHJ-UHFFFAOYSA-N ClC=1C=CC(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1)OC(F)(F)F)C1=C(C=CC=C1CC)CC Chemical compound ClC=1C=CC(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1)OC(F)(F)F)C1=C(C=CC=C1CC)CC GXMREGOXQFHIHJ-UHFFFAOYSA-N 0.000 description 1
- YLZKDONQKOGHIM-UHFFFAOYSA-N ClC=1C=CC(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1C)C(F)(F)F)C1=C(C=CC=C1CC)CC Chemical compound ClC=1C=CC(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1C)C(F)(F)F)C1=C(C=CC=C1CC)CC YLZKDONQKOGHIM-UHFFFAOYSA-N 0.000 description 1
- ZUXKDEPEPDRIPL-UHFFFAOYSA-N ClC=1C=CC(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1F)C(F)(F)F)C1=C(C=CC=C1C)C Chemical compound ClC=1C=CC(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1F)C(F)(F)F)C1=C(C=CC=C1C)C ZUXKDEPEPDRIPL-UHFFFAOYSA-N 0.000 description 1
- KXVNBZIUANIDLC-UHFFFAOYSA-N ClC=1C=CC(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1F)C(F)(F)F)C1=C(C=CC=C1CC)CC Chemical compound ClC=1C=CC(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1F)C(F)(F)F)C1=C(C=CC=C1CC)CC KXVNBZIUANIDLC-UHFFFAOYSA-N 0.000 description 1
- JXPFLPCELGOYBJ-UHFFFAOYSA-N ClC=1C=CC(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1F)C1CC1)C1=C(C=CC=C1CC)CC Chemical compound ClC=1C=CC(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=C1F)C1CC1)C1=C(C=CC=C1CC)CC JXPFLPCELGOYBJ-UHFFFAOYSA-N 0.000 description 1
- JSOSAKGIPJPMRQ-UHFFFAOYSA-N ClC=1C=CC(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=N1)C(=O)N)C1=C(C=CC=C1CC)CC Chemical compound ClC=1C=CC(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=N1)C(=O)N)C1=C(C=CC=C1CC)CC JSOSAKGIPJPMRQ-UHFFFAOYSA-N 0.000 description 1
- LKNAKRNPZLHLOG-UHFFFAOYSA-N ClC=1C=CC(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=N1)C(=O)O)C1=C(C=CC=C1CC)CC Chemical compound ClC=1C=CC(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=N1)C(=O)O)C1=C(C=CC=C1CC)CC LKNAKRNPZLHLOG-UHFFFAOYSA-N 0.000 description 1
- WEZXJTVYQUFOAR-UHFFFAOYSA-N ClC=1C=CC(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=N1)C(C)(C)O)C1=C(C=CC=C1CC)CC Chemical compound ClC=1C=CC(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=N1)C(C)(C)O)C1=C(C=CC=C1CC)CC WEZXJTVYQUFOAR-UHFFFAOYSA-N 0.000 description 1
- DVCWVWGXVZRIQE-UHFFFAOYSA-N ClC=1C=CC(=C2C=NNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=N1)C(F)(F)F)C1=C(C=CC=C1CC)CC Chemical compound ClC=1C=CC(=C2C=NNC=12)C=1N(N=C2C=1CN(CC2)C1=NC=C(C=N1)C(F)(F)F)C1=C(C=CC=C1CC)CC DVCWVWGXVZRIQE-UHFFFAOYSA-N 0.000 description 1
- OIRAEJWYWSAQNG-UHFFFAOYSA-N Clidanac Chemical compound ClC=1C=C2C(C(=O)O)CCC2=CC=1C1CCCCC1 OIRAEJWYWSAQNG-UHFFFAOYSA-N 0.000 description 1
- 101710172562 Cobra venom factor Proteins 0.000 description 1
- 206010009895 Colitis ischaemic Diseases 0.000 description 1
- 108010078546 Complement C5a Proteins 0.000 description 1
- 108010069112 Complement System Proteins Proteins 0.000 description 1
- 102000000989 Complement System Proteins Human genes 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 206010011091 Coronary artery thrombosis Diseases 0.000 description 1
- OMFXVFTZEKFJBZ-UHFFFAOYSA-N Corticosterone Natural products O=C1CCC2(C)C3C(O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 OMFXVFTZEKFJBZ-UHFFFAOYSA-N 0.000 description 1
- 208000011231 Crohn disease Diseases 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- 229930105110 Cyclosporin A Natural products 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- IGXWBGJHJZYPQS-SSDOTTSWSA-N D-Luciferin Chemical compound OC(=O)[C@H]1CSC(C=2SC3=CC=C(O)C=C3N=2)=N1 IGXWBGJHJZYPQS-SSDOTTSWSA-N 0.000 description 1
- 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 1
- AEMOLEFTQBMNLQ-YMDCURPLSA-N D-galactopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-YMDCURPLSA-N 0.000 description 1
- AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 description 1
- CYCGRDQQIOGCKX-UHFFFAOYSA-N Dehydro-luciferin Natural products OC(=O)C1=CSC(C=2SC3=CC(O)=CC=C3N=2)=N1 CYCGRDQQIOGCKX-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 206010012689 Diabetic retinopathy Diseases 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 206010048554 Endothelial dysfunction Diseases 0.000 description 1
- 206010014824 Endotoxic shock Diseases 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- HTIJFSOGRVMCQR-UHFFFAOYSA-N Epirubicin Natural products COc1cccc2C(=O)c3c(O)c4CC(O)(CC(OC5CC(N)C(=O)C(C)O5)c4c(O)c3C(=O)c12)C(=O)CO HTIJFSOGRVMCQR-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 208000009386 Experimental Arthritis Diseases 0.000 description 1
- KIEGQFJTVVZNIA-UHFFFAOYSA-N FC1=CC(=C2C=CNC2=C1C(=O)OC)B1OC(C(O1)(C)C)(C)C Chemical compound FC1=CC(=C2C=CNC2=C1C(=O)OC)B1OC(C(O1)(C)C)(C)C KIEGQFJTVVZNIA-UHFFFAOYSA-N 0.000 description 1
- POHOJUPNMOHHAE-UHFFFAOYSA-N FC1=CC(=C2C=CNC2=C1C)B1OC(C(O1)(C)C)(C)C Chemical compound FC1=CC(=C2C=CNC2=C1C)B1OC(C(O1)(C)C)(C)C POHOJUPNMOHHAE-UHFFFAOYSA-N 0.000 description 1
- JHYUWJYGGHIPCF-UHFFFAOYSA-N FC1=CC(=C2C=CNC2=C1F)B1OC(C(O1)(C)C)(C)C Chemical compound FC1=CC(=C2C=CNC2=C1F)B1OC(C(O1)(C)C)(C)C JHYUWJYGGHIPCF-UHFFFAOYSA-N 0.000 description 1
- UFWWYYDCECYNRL-UHFFFAOYSA-N FC1=CC(=C2C=CNC2=C1OC)B1OC(C(O1)(C)C)(C)C Chemical compound FC1=CC(=C2C=CNC2=C1OC)B1OC(C(O1)(C)C)(C)C UFWWYYDCECYNRL-UHFFFAOYSA-N 0.000 description 1
- SUIMBHPADQNKPV-UHFFFAOYSA-N FC1=CC(=C2C=NNC2=C1OC)B1OC(C(O1)(C)C)(C)C Chemical compound FC1=CC(=C2C=NNC2=C1OC)B1OC(C(O1)(C)C)(C)C SUIMBHPADQNKPV-UHFFFAOYSA-N 0.000 description 1
- SYCCYEKDHDQTGY-UHFFFAOYSA-N FC=1C(=C2C=CNC2=C(C=1)C(=O)OC)B1OC(C(O1)(C)C)(C)C Chemical compound FC=1C(=C2C=CNC2=C(C=1)C(=O)OC)B1OC(C(O1)(C)C)(C)C SYCCYEKDHDQTGY-UHFFFAOYSA-N 0.000 description 1
- MZFCZWWSDCZQPN-UHFFFAOYSA-N FC=1C(=C2C=CNC2=C(C=1)C)B1OC(C(O1)(C)C)(C)C Chemical compound FC=1C(=C2C=CNC2=C(C=1)C)B1OC(C(O1)(C)C)(C)C MZFCZWWSDCZQPN-UHFFFAOYSA-N 0.000 description 1
- QNYLPOZKCINHCZ-UHFFFAOYSA-N FC=1C(=C2C=CNC2=C(C=1)OC)B1OC(C(O1)(C)C)(C)C Chemical compound FC=1C(=C2C=CNC2=C(C=1)OC)B1OC(C(O1)(C)C)(C)C QNYLPOZKCINHCZ-UHFFFAOYSA-N 0.000 description 1
- USCGMLQDXYHARW-UHFFFAOYSA-N FC=1C(=C2C=NNC2=C(C=1)C)C=1N(N=C2C=1CN(CC2)C1(NC=C(C=C1)C(F)(F)F)F)C1=C(C=CC=C1C)C Chemical compound FC=1C(=C2C=NNC2=C(C=1)C)C=1N(N=C2C=1CN(CC2)C1(NC=C(C=C1)C(F)(F)F)F)C1=C(C=CC=C1C)C USCGMLQDXYHARW-UHFFFAOYSA-N 0.000 description 1
- XZTWIOLWWBDOFH-UHFFFAOYSA-N FC=1C=CC(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C(=O)OC(C)(C)C)C1=C(C=CC=C1CC)CC Chemical compound FC=1C=CC(=C2C=CNC=12)C=1N(N=C2C=1CN(CC2)C(=O)OC(C)(C)C)C1=C(C=CC=C1CC)CC XZTWIOLWWBDOFH-UHFFFAOYSA-N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- RBBWCVQDXDFISW-UHFFFAOYSA-N Feprazone Chemical compound O=C1C(CC=C(C)C)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 RBBWCVQDXDFISW-UHFFFAOYSA-N 0.000 description 1
- BJGNCJDXODQBOB-UHFFFAOYSA-N Fivefly Luciferin Natural products OC(=O)C1CSC(C=2SC3=CC(O)=CC=C3N=2)=N1 BJGNCJDXODQBOB-UHFFFAOYSA-N 0.000 description 1
- WJOHZNCJWYWUJD-IUGZLZTKSA-N Fluocinonide Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)COC(=O)C)[C@@]2(C)C[C@@H]1O WJOHZNCJWYWUJD-IUGZLZTKSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 201000011240 Frontotemporal dementia Diseases 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
- 108010010803 Gelatin Proteins 0.000 description 1
- 206010018370 Glomerulonephritis membranoproliferative Diseases 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 208000009329 Graft vs Host Disease Diseases 0.000 description 1
- MUQNGPZZQDCDFT-JNQJZLCISA-N Halcinonide Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CCl)[C@@]1(C)C[C@@H]2O MUQNGPZZQDCDFT-JNQJZLCISA-N 0.000 description 1
- 208000032843 Hemorrhage Diseases 0.000 description 1
- 101000716065 Homo sapiens C-C chemokine receptor type 7 Proteins 0.000 description 1
- 101000916050 Homo sapiens C-X-C chemokine receptor type 3 Proteins 0.000 description 1
- 101000856683 Homo sapiens C-X-C chemokine receptor type 6 Proteins 0.000 description 1
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 1
- 208000035150 Hypercholesterolemia Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
- XDXDZDZNSLXDNA-TZNDIEGXSA-N Idarubicin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XDXDZDZNSLXDNA-TZNDIEGXSA-N 0.000 description 1
- XDXDZDZNSLXDNA-UHFFFAOYSA-N Idarubicin Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XDXDZDZNSLXDNA-UHFFFAOYSA-N 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- 206010061216 Infarction Diseases 0.000 description 1
- 108010008212 Integrin alpha4beta1 Proteins 0.000 description 1
- 108010002352 Interleukin-1 Proteins 0.000 description 1
- 102000000589 Interleukin-1 Human genes 0.000 description 1
- 102000003777 Interleukin-1 beta Human genes 0.000 description 1
- 108090000193 Interleukin-1 beta Proteins 0.000 description 1
- 108090001005 Interleukin-6 Proteins 0.000 description 1
- 102000004889 Interleukin-6 Human genes 0.000 description 1
- 108090001007 Interleukin-8 Proteins 0.000 description 1
- 102000004890 Interleukin-8 Human genes 0.000 description 1
- 108010018951 Interleukin-8B Receptors Proteins 0.000 description 1
- 206010022680 Intestinal ischaemia Diseases 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
- HUYWAWARQUIQLE-UHFFFAOYSA-N Isoetharine Chemical compound CC(C)NC(CC)C(O)C1=CC=C(O)C(O)=C1 HUYWAWARQUIQLE-UHFFFAOYSA-N 0.000 description 1
- PWWVAXIEGOYWEE-UHFFFAOYSA-N Isophenergan Chemical compound C1=CC=C2N(CC(C)N(C)C)C3=CC=CC=C3SC2=C1 PWWVAXIEGOYWEE-UHFFFAOYSA-N 0.000 description 1
- UETNIIAIRMUTSM-UHFFFAOYSA-N Jacareubin Natural products CC1(C)OC2=CC3Oc4c(O)c(O)ccc4C(=O)C3C(=C2C=C1)O UETNIIAIRMUTSM-UHFFFAOYSA-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
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 208000032514 Leukocytoclastic vasculitis Diseases 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- GQYIWUVLTXOXAJ-UHFFFAOYSA-N Lomustine Chemical compound ClCCN(N=O)C(=O)NC1CCCCC1 GQYIWUVLTXOXAJ-UHFFFAOYSA-N 0.000 description 1
- DDWFXDSYGUXRAY-UHFFFAOYSA-N Luciferin Natural products CCc1c(C)c(CC2NC(=O)C(=C2C=C)C)[nH]c1Cc3[nH]c4C(=C5/NC(CC(=O)O)C(C)C5CC(=O)O)CC(=O)c4c3C DDWFXDSYGUXRAY-UHFFFAOYSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 102000009112 Mannose-Binding Lectin Human genes 0.000 description 1
- 108010087870 Mannose-Binding Lectin Proteins 0.000 description 1
- SBDNJUWAMKYJOX-UHFFFAOYSA-N Meclofenamic Acid Chemical compound CC1=CC=C(Cl)C(NC=2C(=CC=CC=2)C(O)=O)=C1Cl SBDNJUWAMKYJOX-UHFFFAOYSA-N 0.000 description 1
- 208000004451 Membranoproliferative Glomerulonephritis Diseases 0.000 description 1
- UCHDWCPVSPXUMX-TZIWLTJVSA-N Montelukast Chemical compound CC(C)(O)C1=CC=CC=C1CC[C@H](C=1C=C(\C=C\C=2N=C3C=C(Cl)C=CC3=CC=2)C=CC=1)SCC1(CC(O)=O)CC1 UCHDWCPVSPXUMX-TZIWLTJVSA-N 0.000 description 1
- HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 1
- IJHNSHDBIRRJRN-UHFFFAOYSA-N N,N-dimethyl-3-phenyl-3-(2-pyridinyl)-1-propanamine Chemical compound C=1C=CC=NC=1C(CCN(C)C)C1=CC=CC=C1 IJHNSHDBIRRJRN-UHFFFAOYSA-N 0.000 description 1
- WYBVBIHNJWOLCJ-UHFFFAOYSA-N N-L-arginyl-L-leucine Natural products CC(C)CC(C(O)=O)NC(=O)C(N)CCCN=C(N)N WYBVBIHNJWOLCJ-UHFFFAOYSA-N 0.000 description 1
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 description 1
- 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
- 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 1
- WWCSHJPVSJSJIA-UHFFFAOYSA-N N1C(=NC=C1)C(=O)N.CN(N=N)C Chemical compound N1C(=NC=C1)C(=O)N.CN(N=N)C WWCSHJPVSJSJIA-UHFFFAOYSA-N 0.000 description 1
- FKBUKTMQLDBUJO-UHFFFAOYSA-N N1C=CC2=CC(=CC=C12)C=1N(N=C2C=1CNCC2)C1=C(C=CC=C1C)OCC(C)C Chemical compound N1C=CC2=CC(=CC=C12)C=1N(N=C2C=1CNCC2)C1=C(C=CC=C1C)OCC(C)C FKBUKTMQLDBUJO-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 1
- JAUOIFJMECXRGI-UHFFFAOYSA-N Neoclaritin Chemical compound C=1C(Cl)=CC=C2C=1CCC1=CC=CN=C1C2=C1CCNCC1 JAUOIFJMECXRGI-UHFFFAOYSA-N 0.000 description 1
- 208000001738 Nervous System Trauma Diseases 0.000 description 1
- JZFPYUNJRRFVQU-UHFFFAOYSA-N Niflumic acid Chemical compound OC(=O)C1=CC=CN=C1NC1=CC=CC(C(F)(F)F)=C1 JZFPYUNJRRFVQU-UHFFFAOYSA-N 0.000 description 1
- 229910003849 O-Si Inorganic materials 0.000 description 1
- YXDCOZHIFZNRGH-UHFFFAOYSA-N OC1=CC=CB1 Chemical compound OC1=CC=CB1 YXDCOZHIFZNRGH-UHFFFAOYSA-N 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 206010053159 Organ failure Diseases 0.000 description 1
- 229910003872 O—Si Inorganic materials 0.000 description 1
- 206010033645 Pancreatitis Diseases 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 241000721454 Pemphigus Species 0.000 description 1
- 208000027086 Pemphigus foliaceus Diseases 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 1
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 1
- 208000000609 Pick Disease of the Brain Diseases 0.000 description 1
- VQDBNKDJNJQRDG-UHFFFAOYSA-N Pirbuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=N1 VQDBNKDJNJQRDG-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 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
- TVQZAMVBTVNYLA-UHFFFAOYSA-N Pranoprofen Chemical compound C1=CC=C2CC3=CC(C(C(O)=O)C)=CC=C3OC2=N1 TVQZAMVBTVNYLA-UHFFFAOYSA-N 0.000 description 1
- 208000024777 Prion disease Diseases 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 206010037394 Pulmonary haemorrhage Diseases 0.000 description 1
- 206010037549 Purpura Diseases 0.000 description 1
- 241001672981 Purpura Species 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
- 208000034541 Rare lymphatic malformation Diseases 0.000 description 1
- 101100006979 Rattus norvegicus C4 gene Proteins 0.000 description 1
- 206010038563 Reocclusion Diseases 0.000 description 1
- 241000219061 Rheum Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 206010039710 Scleroderma Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229940123237 Taxane Drugs 0.000 description 1
- FOCVUCIESVLUNU-UHFFFAOYSA-N Thiotepa Chemical compound C1CN1P(N1CC1)(=S)N1CC1 FOCVUCIESVLUNU-UHFFFAOYSA-N 0.000 description 1
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
- UFLGIAIHIAPJJC-UHFFFAOYSA-N Tripelennamine Chemical compound C=1C=CC=NC=1N(CCN(C)C)CC1=CC=CC=C1 UFLGIAIHIAPJJC-UHFFFAOYSA-N 0.000 description 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
- 206010053648 Vascular occlusion Diseases 0.000 description 1
- CJWLNZTYZMEELO-UHFFFAOYSA-N [CH2-]C(=O)C.[F] Chemical compound [CH2-]C(=O)C.[F] CJWLNZTYZMEELO-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 description 1
- MJBWDEQAUQTVKK-IAGOWNOFSA-N aflatoxin M1 Chemical compound C=1([C@]2(O)C=CO[C@@H]2OC=1C=C(C1=2)OC)C=2OC(=O)C2=C1CCC2=O MJBWDEQAUQTVKK-IAGOWNOFSA-N 0.000 description 1
- 206010064930 age-related macular degeneration Diseases 0.000 description 1
- 229960005142 alclofenac Drugs 0.000 description 1
- ARHWPKZXBHOEEE-UHFFFAOYSA-N alclofenac Chemical compound OC(=O)CC1=CC=C(OCC=C)C(Cl)=C1 ARHWPKZXBHOEEE-UHFFFAOYSA-N 0.000 description 1
- DJHCCTTVDRAMEH-DUUJBDRPSA-N alclometasone dipropionate Chemical compound C([C@H]1Cl)C2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O DJHCCTTVDRAMEH-DUUJBDRPSA-N 0.000 description 1
- 229960004229 alclometasone dipropionate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 229960003790 alimemazine Drugs 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 125000005237 alkyleneamino group Chemical group 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- 125000005530 alkylenedioxy group Chemical group 0.000 description 1
- 125000005529 alkyleneoxy group Chemical group 0.000 description 1
- 125000004419 alkynylene group Chemical group 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 229960004663 alminoprofen Drugs 0.000 description 1
- FPHLBGOJWPEVME-UHFFFAOYSA-N alminoprofen Chemical compound OC(=O)C(C)C1=CC=C(NCC(C)=C)C=C1 FPHLBGOJWPEVME-UHFFFAOYSA-N 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229960000473 altretamine Drugs 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- ILKJAFIWWBXGDU-MOGDOJJUSA-N amcinonide Chemical compound O([C@@]1([C@H](O2)C[C@@H]3[C@@]1(C[C@H](O)[C@]1(F)[C@@]4(C)C=CC(=O)C=C4CC[C@H]13)C)C(=O)COC(=O)C)C12CCCC1 ILKJAFIWWBXGDU-MOGDOJJUSA-N 0.000 description 1
- 229960003099 amcinonide Drugs 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229920000469 amphiphilic block copolymer Polymers 0.000 description 1
- 230000002052 anaphylactic effect Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229960002469 antazoline Drugs 0.000 description 1
- REYFJDPCWQRWAA-UHFFFAOYSA-N antazoline Chemical compound N=1CCNC=1CN(C=1C=CC=CC=1)CC1=CC=CC=C1 REYFJDPCWQRWAA-UHFFFAOYSA-N 0.000 description 1
- 229940045799 anthracyclines and related substance Drugs 0.000 description 1
- 230000001088 anti-asthma Effects 0.000 description 1
- 230000003367 anti-collagen effect Effects 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 230000000340 anti-metabolite Effects 0.000 description 1
- 239000000924 antiasthmatic agent Substances 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 229940111133 antiinflammatory and antirheumatic drug oxicams Drugs 0.000 description 1
- 229940111131 antiinflammatory and antirheumatic product propionic acid derivative Drugs 0.000 description 1
- 229940100197 antimetabolite Drugs 0.000 description 1
- 239000002256 antimetabolite Substances 0.000 description 1
- 229940045687 antimetabolites folic acid analogs Drugs 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940045719 antineoplastic alkylating agent nitrosoureas Drugs 0.000 description 1
- 238000002617 apheresis Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229960003121 arginine Drugs 0.000 description 1
- 206010003230 arteritis Diseases 0.000 description 1
- 239000002473 artificial blood Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- GXDALQBWZGODGZ-UHFFFAOYSA-N astemizole Chemical compound C1=CC(OC)=CC=C1CCN1CCC(NC=2N(C3=CC=CC=C3N=2)CC=2C=CC(F)=CC=2)CC1 GXDALQBWZGODGZ-UHFFFAOYSA-N 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 210000001130 astrocyte Anatomy 0.000 description 1
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 1
- 229960000396 atropine Drugs 0.000 description 1
- 229960001799 aurothioglucose Drugs 0.000 description 1
- VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 description 1
- WOIIIUDZSOLAIW-NSHDSACASA-N azapropazone Chemical compound C1=C(C)C=C2N3C(=O)[C@H](CC=C)C(=O)N3C(N(C)C)=NC2=C1 WOIIIUDZSOLAIW-NSHDSACASA-N 0.000 description 1
- 229960001671 azapropazone Drugs 0.000 description 1
- 229960000383 azatadine Drugs 0.000 description 1
- SEBMTIQKRHYNIT-UHFFFAOYSA-N azatadine Chemical compound C1CN(C)CCC1=C1C2=NC=CC=C2CCC2=CC=CC=C21 SEBMTIQKRHYNIT-UHFFFAOYSA-N 0.000 description 1
- 125000002393 azetidinyl group Chemical group 0.000 description 1
- 229960004669 basiliximab Drugs 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229960005430 benoxaprofen Drugs 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
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- GPRLTFBKWDERLU-UHFFFAOYSA-N bicyclo[2.2.2]octane Chemical compound C1CC2CCC1CC2 GPRLTFBKWDERLU-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000002306 biochemical method Methods 0.000 description 1
- 229920002988 biodegradable polymer Polymers 0.000 description 1
- 239000004621 biodegradable polymer Substances 0.000 description 1
- 229920001222 biopolymer Polymers 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- FZGVEKPRDOIXJY-UHFFFAOYSA-N bitolterol Chemical compound C1=CC(C)=CC=C1C(=O)OC1=CC=C(C(O)CNC(C)(C)C)C=C1OC(=O)C1=CC=C(C)C=C1 FZGVEKPRDOIXJY-UHFFFAOYSA-N 0.000 description 1
- 229960004620 bitolterol Drugs 0.000 description 1
- 210000001772 blood platelet Anatomy 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- ZDIGNSYAACHWNL-UHFFFAOYSA-N brompheniramine Chemical compound C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Br)C=C1 ZDIGNSYAACHWNL-UHFFFAOYSA-N 0.000 description 1
- 229960000725 brompheniramine Drugs 0.000 description 1
- 230000007885 bronchoconstriction Effects 0.000 description 1
- IJTPQQVCKPZIMV-UHFFFAOYSA-N bucloxic acid Chemical compound ClC1=CC(C(=O)CCC(=O)O)=CC=C1C1CCCCC1 IJTPQQVCKPZIMV-UHFFFAOYSA-N 0.000 description 1
- 229950005608 bucloxic acid Drugs 0.000 description 1
- 208000000594 bullous pemphigoid Diseases 0.000 description 1
- 229960002092 busulfan Drugs 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
- 210000004899 c-terminal region Anatomy 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
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 230000004856 capillary permeability Effects 0.000 description 1
- 229960004562 carboplatin Drugs 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 229960005243 carmustine Drugs 0.000 description 1
- 229960003184 carprofen Drugs 0.000 description 1
- IVUMCTKHWDRRMH-UHFFFAOYSA-N carprofen Chemical compound C1=CC(Cl)=C[C]2C3=CC=C(C(C(O)=O)C)C=C3N=C21 IVUMCTKHWDRRMH-UHFFFAOYSA-N 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 229940047495 celebrex Drugs 0.000 description 1
- 229960000590 celecoxib Drugs 0.000 description 1
- 230000006037 cell lysis Effects 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 229960001803 cetirizine Drugs 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 229960004630 chlorambucil Drugs 0.000 description 1
- JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 description 1
- SOYKEARSMXGVTM-UHFFFAOYSA-N chlorphenamine Chemical compound C=1C=CC=NC=1C(CCN(C)C)C1=CC=C(Cl)C=C1 SOYKEARSMXGVTM-UHFFFAOYSA-N 0.000 description 1
- 229960003291 chlorphenamine 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
- 230000001684 chronic effect Effects 0.000 description 1
- 230000007882 cirrhosis Effects 0.000 description 1
- 208000019425 cirrhosis of liver Diseases 0.000 description 1
- 229960004316 cisplatin Drugs 0.000 description 1
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
- 229960002881 clemastine Drugs 0.000 description 1
- YNNUSGIPVFPVBX-NHCUHLMSSA-N clemastine Chemical compound CN1CCC[C@@H]1CCO[C@@](C)(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 YNNUSGIPVFPVBX-NHCUHLMSSA-N 0.000 description 1
- 229950010886 clidanac Drugs 0.000 description 1
- 229960002842 clobetasol Drugs 0.000 description 1
- 229960001146 clobetasone Drugs 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 230000006999 cognitive decline Effects 0.000 description 1
- 208000010877 cognitive disease Diseases 0.000 description 1
- 229940126681 complement 5a receptor antagonist Drugs 0.000 description 1
- 208000010247 contact dermatitis Diseases 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 208000002528 coronary thrombosis Diseases 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229960000265 cromoglicic acid Drugs 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 201000003278 cryoglobulinemia Diseases 0.000 description 1
- 210000004748 cultured cell Anatomy 0.000 description 1
- 208000004921 cutaneous lupus erythematosus Diseases 0.000 description 1
- SNRCKKQHDUIRIY-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloromethane;dichloropalladium;iron(2+) Chemical compound [Fe+2].ClCCl.Cl[Pd]Cl.C1=C[CH-]C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.C1=C[CH-]C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 SNRCKKQHDUIRIY-UHFFFAOYSA-L 0.000 description 1
- WLVKDFJTYKELLQ-UHFFFAOYSA-N cyclopropylboronic acid Chemical compound OB(O)C1CC1 WLVKDFJTYKELLQ-UHFFFAOYSA-N 0.000 description 1
- 229930182912 cyclosporin Natural products 0.000 description 1
- 229960001140 cyproheptadine Drugs 0.000 description 1
- JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 1
- 229960000684 cytarabine Drugs 0.000 description 1
- 230000001086 cytosolic effect Effects 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 229960002806 daclizumab Drugs 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 201000001981 dermatomyositis Diseases 0.000 description 1
- 229960001271 desloratadine Drugs 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 238000002059 diagnostic imaging Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 229960001259 diclofenac Drugs 0.000 description 1
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- HUPFGZXOMWLGNK-UHFFFAOYSA-N diflunisal Chemical compound C1=C(O)C(C(=O)O)=CC(C=2C(=CC(F)=CC=2)F)=C1 HUPFGZXOMWLGNK-UHFFFAOYSA-N 0.000 description 1
- 229960000616 diflunisal Drugs 0.000 description 1
- 229960000520 diphenhydramine Drugs 0.000 description 1
- OWQUZNMMYNAXSL-UHFFFAOYSA-N diphenylpyraline Chemical compound C1CN(C)CCC1OC(C=1C=CC=CC=1)C1=CC=CC=C1 OWQUZNMMYNAXSL-UHFFFAOYSA-N 0.000 description 1
- 229960000879 diphenylpyraline Drugs 0.000 description 1
- 208000037765 diseases and disorders Diseases 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- VLARUOGDXDTHEH-UHFFFAOYSA-L disodium cromoglycate Chemical compound [Na+].[Na+].O1C(C([O-])=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C([O-])=O)O2 VLARUOGDXDTHEH-UHFFFAOYSA-L 0.000 description 1
- 229960003668 docetaxel Drugs 0.000 description 1
- 229960004679 doxorubicin Drugs 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000008694 endothelial dysfunction Effects 0.000 description 1
- 239000002158 endotoxin Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229960001904 epirubicin Drugs 0.000 description 1
- 210000002919 epithelial cell Anatomy 0.000 description 1
- 210000005081 epithelial layer Anatomy 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 201000001155 extrinsic allergic alveolitis Diseases 0.000 description 1
- ZWJINEZUASEZBH-UHFFFAOYSA-N fenamic acid Chemical class OC(=O)C1=CC=CC=C1NC1=CC=CC=C1 ZWJINEZUASEZBH-UHFFFAOYSA-N 0.000 description 1
- ZPAKPRAICRBAOD-UHFFFAOYSA-N fenbufen Chemical compound C1=CC(C(=O)CCC(=O)O)=CC=C1C1=CC=CC=C1 ZPAKPRAICRBAOD-UHFFFAOYSA-N 0.000 description 1
- 229960001395 fenbufen Drugs 0.000 description 1
- 229950006236 fenclofenac Drugs 0.000 description 1
- IDKAXRLETRCXKS-UHFFFAOYSA-N fenclofenac Chemical compound OC(=O)CC1=CC=CC=C1OC1=CC=C(Cl)C=C1Cl IDKAXRLETRCXKS-UHFFFAOYSA-N 0.000 description 1
- 229950011481 fenclozic acid Drugs 0.000 description 1
- 229960001419 fenoprofen Drugs 0.000 description 1
- 229960001022 fenoterol Drugs 0.000 description 1
- 229960002679 fentiazac Drugs 0.000 description 1
- 229960000489 feprazone Drugs 0.000 description 1
- 229960003592 fexofenadine Drugs 0.000 description 1
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 description 1
- 230000004761 fibrosis Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229960000961 floxuridine Drugs 0.000 description 1
- 229960004369 flufenamic acid Drugs 0.000 description 1
- LPEPZBJOKDYZAD-UHFFFAOYSA-N flufenamic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=CC(C(F)(F)F)=C1 LPEPZBJOKDYZAD-UHFFFAOYSA-N 0.000 description 1
- 229950007979 flufenisal Drugs 0.000 description 1
- 229960001347 fluocinolone acetonide Drugs 0.000 description 1
- FEBLZLNTKCEFIT-VSXGLTOVSA-N fluocinolone acetonide Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O FEBLZLNTKCEFIT-VSXGLTOVSA-N 0.000 description 1
- 229960000785 fluocinonide Drugs 0.000 description 1
- 229960003973 fluocortolone Drugs 0.000 description 1
- GAKMQHDJQHZUTJ-ULHLPKEOSA-N fluocortolone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@@H](C)[C@H](C(=O)CO)[C@@]2(C)C[C@@H]1O GAKMQHDJQHZUTJ-ULHLPKEOSA-N 0.000 description 1
- 229940091249 fluoride supplement Drugs 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229940060037 fluorine Drugs 0.000 description 1
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 1
- 229950001284 fluprofen Drugs 0.000 description 1
- 229960002390 flurbiprofen Drugs 0.000 description 1
- SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 description 1
- 229960002714 fluticasone Drugs 0.000 description 1
- MGNNYOODZCAHBA-GQKYHHCASA-N fluticasone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(O)[C@@]2(C)C[C@@H]1O MGNNYOODZCAHBA-GQKYHHCASA-N 0.000 description 1
- 150000002224 folic acids Chemical class 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229950010931 furofenac Drugs 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 230000001434 glomerular Effects 0.000 description 1
- 125000004383 glucosinolate group Chemical group 0.000 description 1
- 229940097043 glucuronic acid Drugs 0.000 description 1
- 229940074045 glyceryl distearate Drugs 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 150000002344 gold compounds Chemical class 0.000 description 1
- 208000024908 graft versus host disease Diseases 0.000 description 1
- 239000003979 granulating agent Substances 0.000 description 1
- 229960002383 halcinonide Drugs 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 210000003709 heart valve Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 210000003494 hepatocyte Anatomy 0.000 description 1
- UUVWYPNAQBNQJQ-UHFFFAOYSA-N hexamethylmelamine Chemical compound CN(C)C1=NC(N(C)C)=NC(N(C)C)=N1 UUVWYPNAQBNQJQ-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 229960002885 histidine Drugs 0.000 description 1
- 102000056190 human C5AR1 Human genes 0.000 description 1
- 208000010544 human prion disease Diseases 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 229940091173 hydantoin Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 229960000930 hydroxyzine Drugs 0.000 description 1
- ZQDWXGKKHFNSQK-UHFFFAOYSA-N hydroxyzine Chemical compound C1CN(CCOCCO)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZQDWXGKKHFNSQK-UHFFFAOYSA-N 0.000 description 1
- 208000022098 hypersensitivity pneumonitis Diseases 0.000 description 1
- 201000006362 hypersensitivity vasculitis Diseases 0.000 description 1
- 229960001680 ibuprofen Drugs 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229960000908 idarubicin Drugs 0.000 description 1
- HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 description 1
- 229960001101 ifosfamide Drugs 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000003100 immobilizing effect Effects 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 229940027941 immunoglobulin g Drugs 0.000 description 1
- 229940125721 immunosuppressive agent Drugs 0.000 description 1
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 229960004187 indoprofen Drugs 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 230000007574 infarction Effects 0.000 description 1
- 239000012678 infectious agent Substances 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 230000006749 inflammatory damage Effects 0.000 description 1
- 229960000598 infliximab Drugs 0.000 description 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 229940102213 injectable suspension Drugs 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 230000017306 interleukin-6 production Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- ZCYVEMRRCGMTRW-YPZZEJLDSA-N iodine-125 Chemical compound [125I] ZCYVEMRRCGMTRW-YPZZEJLDSA-N 0.000 description 1
- 229940044173 iodine-125 Drugs 0.000 description 1
- 229960001361 ipratropium bromide Drugs 0.000 description 1
- KEWHKYJURDBRMN-ZEODDXGYSA-M ipratropium bromide hydrate Chemical compound O.[Br-].O([C@H]1C[C@H]2CC[C@@H](C1)[N@@+]2(C)C(C)C)C(=O)C(CO)C1=CC=CC=C1 KEWHKYJURDBRMN-ZEODDXGYSA-M 0.000 description 1
- 229950000831 iralukast Drugs 0.000 description 1
- 208000002551 irritable bowel syndrome Diseases 0.000 description 1
- 208000012947 ischemia reperfusion injury Diseases 0.000 description 1
- 201000008222 ischemic colitis Diseases 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 229960001268 isoetarine Drugs 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 229940039009 isoproterenol Drugs 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 230000000155 isotopic effect Effects 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- QFGMXJOBTNZHEL-UHFFFAOYSA-N isoxepac Chemical compound O1CC2=CC=CC=C2C(=O)C2=CC(CC(=O)O)=CC=C21 QFGMXJOBTNZHEL-UHFFFAOYSA-N 0.000 description 1
- 229950011455 isoxepac Drugs 0.000 description 1
- 229950002252 isoxicam Drugs 0.000 description 1
- YYUAYBYLJSNDCX-UHFFFAOYSA-N isoxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC=1C=C(C)ON=1 YYUAYBYLJSNDCX-UHFFFAOYSA-N 0.000 description 1
- 210000001503 joint Anatomy 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
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 description 1
- 229960000991 ketoprofen Drugs 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000011268 leukocyte chemotaxis Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000004807 localization Effects 0.000 description 1
- 230000007762 localization of cell Effects 0.000 description 1
- 229960002247 lomustine Drugs 0.000 description 1
- 229960003088 loratadine Drugs 0.000 description 1
- JCCNYMKQOSZNPW-UHFFFAOYSA-N loratadine Chemical compound C1CN(C(=O)OCC)CCC1=C1C2=NC=CC=C2CCC2=CC(Cl)=CC=C21 JCCNYMKQOSZNPW-UHFFFAOYSA-N 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000002132 lysosomal effect Effects 0.000 description 1
- JVGUNCHERKJFCM-UHFFFAOYSA-N mabuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(=O)NCCO)C=C1 JVGUNCHERKJFCM-UHFFFAOYSA-N 0.000 description 1
- 229950001846 mabuprofen Drugs 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 208000002780 macular degeneration Diseases 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000013507 mapping Methods 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 229960003803 meclofenamic acid Drugs 0.000 description 1
- 229960003464 mefenamic acid Drugs 0.000 description 1
- HYYBABOKPJLUIN-UHFFFAOYSA-N mefenamic acid Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)C(O)=O)=C1C HYYBABOKPJLUIN-UHFFFAOYSA-N 0.000 description 1
- 229960001924 melphalan Drugs 0.000 description 1
- 229960000582 mepyramine Drugs 0.000 description 1
- YECBIJXISLIIDS-UHFFFAOYSA-N mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 1
- LMOINURANNBYCM-UHFFFAOYSA-N metaproterenol Chemical compound CC(C)NCC(O)C1=CC(O)=CC(O)=C1 LMOINURANNBYCM-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- HTMIBDQKFHUPSX-UHFFFAOYSA-N methdilazine Chemical compound C1N(C)CCC1CN1C2=CC=CC=C2SC2=CC=CC=C21 HTMIBDQKFHUPSX-UHFFFAOYSA-N 0.000 description 1
- 229960004056 methdilazine Drugs 0.000 description 1
- 229960000485 methotrexate Drugs 0.000 description 1
- QGMRHJXVQJIKHE-UHFFFAOYSA-N methyl 2-amino-4-bromo-6-fluoro-3-nitrobenzoate Chemical compound COC(=O)C1=C(F)C=C(Br)C([N+]([O-])=O)=C1N QGMRHJXVQJIKHE-UHFFFAOYSA-N 0.000 description 1
- JTBLJEGYYYHKGQ-UHFFFAOYSA-N methyl 4-bromo-1h-indole-7-carboxylate Chemical compound COC(=O)C1=CC=C(Br)C2=C1NC=C2 JTBLJEGYYYHKGQ-UHFFFAOYSA-N 0.000 description 1
- DDVIBOYOSCQHPQ-UHFFFAOYSA-N methyl 4-bromo-2,6-difluoro-3-nitrobenzoate Chemical compound COC(=O)C1=C(F)C=C(Br)C([N+]([O-])=O)=C1F DDVIBOYOSCQHPQ-UHFFFAOYSA-N 0.000 description 1
- JBXJLZRTTCGLNR-UHFFFAOYSA-N methyl 4-bromo-2,6-difluorobenzoate Chemical compound COC(=O)C1=C(F)C=C(Br)C=C1F JBXJLZRTTCGLNR-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 210000000274 microglia Anatomy 0.000 description 1
- 206010063344 microscopic polyangiitis Diseases 0.000 description 1
- 238000010232 migration assay Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229960001156 mitoxantrone Drugs 0.000 description 1
- KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229960005285 mofebutazone Drugs 0.000 description 1
- REOJLIXKJWXUGB-UHFFFAOYSA-N mofebutazone Chemical compound O=C1C(CCCC)C(=O)NN1C1=CC=CC=C1 REOJLIXKJWXUGB-UHFFFAOYSA-N 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000006682 monohaloalkyl group Chemical group 0.000 description 1
- 229960005127 montelukast Drugs 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 206010028417 myasthenia gravis Diseases 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- PRVZYDDRMVHWOS-UHFFFAOYSA-N n'-benzhydrylethane-1,2-diamine Chemical compound C=1C=CC=CC=1C(NCCN)C1=CC=CC=C1 PRVZYDDRMVHWOS-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229960002009 naproxen Drugs 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 229940063121 neoral Drugs 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 208000028412 nervous system injury Diseases 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 229960000916 niflumic acid Drugs 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- GYCKQBWUSACYIF-UHFFFAOYSA-N o-hydroxybenzoic acid ethyl ester Natural products CCOC(=O)C1=CC=CC=C1O GYCKQBWUSACYIF-UHFFFAOYSA-N 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 229950005751 ocrelizumab Drugs 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229960002657 orciprenaline Drugs 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 229960001756 oxaliplatin Drugs 0.000 description 1
- DWAFYCQODLXJNR-BNTLRKBRSA-L oxaliplatin Chemical compound O1C(=O)C(=O)O[Pt]11N[C@@H]2CCCC[C@H]2N1 DWAFYCQODLXJNR-BNTLRKBRSA-L 0.000 description 1
- 229960002739 oxaprozin Drugs 0.000 description 1
- OFPXSFXSNFPTHF-UHFFFAOYSA-N oxaprozin Chemical compound O1C(CCC(=O)O)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 OFPXSFXSNFPTHF-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229960000649 oxyphenbutazone Drugs 0.000 description 1
- CNDQSXOVEQXJOE-UHFFFAOYSA-N oxyphenbutazone hydrate Chemical compound O.O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=C(O)C=C1 CNDQSXOVEQXJOE-UHFFFAOYSA-N 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000007310 pathophysiology Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 201000001976 pemphigus vulgaris Diseases 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 229960001190 pheniramine Drugs 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 229950005566 picoplatin Drugs 0.000 description 1
- IIMIOEBMYPRQGU-UHFFFAOYSA-L picoplatin Chemical compound N.[Cl-].[Cl-].[Pt+2].CC1=CC=CC=N1 IIMIOEBMYPRQGU-UHFFFAOYSA-L 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229960005414 pirbuterol Drugs 0.000 description 1
- 229960002702 piroxicam Drugs 0.000 description 1
- QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 description 1
- 229960000851 pirprofen Drugs 0.000 description 1
- PIDSZXPFGCURGN-UHFFFAOYSA-N pirprofen Chemical compound ClC1=CC(C(C(O)=O)C)=CC=C1N1CC=CC1 PIDSZXPFGCURGN-UHFFFAOYSA-N 0.000 description 1
- 229960004403 pixantrone Drugs 0.000 description 1
- PEZPMAYDXJQYRV-UHFFFAOYSA-N pixantrone Chemical compound O=C1C2=CN=CC=C2C(=O)C2=C1C(NCCN)=CC=C2NCCN PEZPMAYDXJQYRV-UHFFFAOYSA-N 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 238000002616 plasmapheresis Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229950011515 pobilukast Drugs 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 201000006292 polyarteritis nodosa Diseases 0.000 description 1
- 229920002721 polycyanoacrylate Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 125000006684 polyhaloalkyl group Polymers 0.000 description 1
- 229920000656 polylysine Polymers 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 150000004804 polysaccharides Chemical class 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 238000002600 positron emission tomography Methods 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 229960004583 pranlukast Drugs 0.000 description 1
- UAJUXJSXCLUTNU-UHFFFAOYSA-N pranlukast Chemical compound C=1C=C(OCCCCC=2C=CC=CC=2)C=CC=1C(=O)NC(C=1)=CC=C(C(C=2)=O)C=1OC=2C=1N=NNN=1 UAJUXJSXCLUTNU-UHFFFAOYSA-N 0.000 description 1
- 229960003101 pranoprofen Drugs 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003141 primary amines Chemical class 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
- 230000008569 process Effects 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229940072288 prograf Drugs 0.000 description 1
- 229960003910 promethazine Drugs 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 150000005599 propionic acid derivatives Chemical class 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000001185 psoriatic effect Effects 0.000 description 1
- 230000008695 pulmonary vasoconstriction Effects 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- QDXGKRWDQCEABB-UHFFFAOYSA-N pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=CN=C1 QDXGKRWDQCEABB-UHFFFAOYSA-N 0.000 description 1
- IIVUJUOJERNGQX-UHFFFAOYSA-N pyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=CN=C1 IIVUJUOJERNGQX-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000003653 radioligand binding assay Methods 0.000 description 1
- 229940099538 rapamune Drugs 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940075993 receptor modulator Drugs 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229940116176 remicade Drugs 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229960000371 rofecoxib Drugs 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 229940063122 sandimmune Drugs 0.000 description 1
- 229960005399 satraplatin Drugs 0.000 description 1
- 190014017285 satraplatin Chemical compound 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound 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
- 238000003345 scintillation counting Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229960003440 semustine Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000009919 sequestration Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229940115586 simulect Drugs 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 230000016160 smooth muscle contraction Effects 0.000 description 1
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229960003339 sodium phosphate Drugs 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical class [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 210000000434 stratum corneum Anatomy 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229950005175 sudoxicam Drugs 0.000 description 1
- 229960001940 sulfasalazine Drugs 0.000 description 1
- NCEXYHBECQHGNR-UHFFFAOYSA-N sulfasalazine Natural products C1=C(O)C(C(=O)O)=CC(N=NC=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-UHFFFAOYSA-N 0.000 description 1
- 229960000894 sulindac Drugs 0.000 description 1
- MLKXDPUZXIRXEP-MFOYZWKCSA-N sulindac Chemical compound CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(S(C)=O)C=C1 MLKXDPUZXIRXEP-MFOYZWKCSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 229960004492 suprofen Drugs 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 238000007892 surgical revascularization Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000002636 symptomatic treatment Methods 0.000 description 1
- 210000001258 synovial membrane Anatomy 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 210000004876 tela submucosa Anatomy 0.000 description 1
- 229960002871 tenoxicam Drugs 0.000 description 1
- WZWYJBNHTWCXIM-UHFFFAOYSA-N tenoxicam Chemical compound O=C1C=2SC=CC=2S(=O)(=O)N(C)C1=C(O)NC1=CC=CC=N1 WZWYJBNHTWCXIM-UHFFFAOYSA-N 0.000 description 1
- 229960000195 terbutaline Drugs 0.000 description 1
- 229960000351 terfenadine Drugs 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- VPFTZTMJPFIRAN-UHFFFAOYSA-N tert-butyl 3-cyano-4-oxopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(=O)C(C#N)C1 VPFTZTMJPFIRAN-UHFFFAOYSA-N 0.000 description 1
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
- 239000012414 tert-butyl nitrite Substances 0.000 description 1
- JYEVUDXCQHLXNG-UHFFFAOYSA-N tert-butyl pyridine-3-carboxylate Chemical compound CC(C)(C)OC(=O)C1=CC=CN=C1 JYEVUDXCQHLXNG-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229960004559 theobromine Drugs 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000004588 thienopyridyl group Chemical group S1C(=CC2=C1C=CC=N2)* 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005309 thioalkoxy group Chemical group 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229960001196 thiotepa Drugs 0.000 description 1
- 229960001312 tiaprofenic acid Drugs 0.000 description 1
- GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 229950002345 tiopinac Drugs 0.000 description 1
- 229950006150 tioxaprofen Drugs 0.000 description 1
- 208000037816 tissue injury Diseases 0.000 description 1
- 229960003114 tixocortol pivalate Drugs 0.000 description 1
- BISFDZNIUZIKJD-XDANTLIUSA-N tixocortol pivalate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)CSC(=O)C(C)(C)C)(O)[C@@]1(C)C[C@@H]2O BISFDZNIUZIKJD-XDANTLIUSA-N 0.000 description 1
- 229960002905 tolfenamic acid Drugs 0.000 description 1
- YEZNLOUZAIOMLT-UHFFFAOYSA-N tolfenamic acid Chemical compound CC1=C(Cl)C=CC=C1NC1=CC=CC=C1C(O)=O YEZNLOUZAIOMLT-UHFFFAOYSA-N 0.000 description 1
- 229960001017 tolmetin Drugs 0.000 description 1
- UPSPUYADGBWSHF-UHFFFAOYSA-N tolmetin Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(O)=O)N1C UPSPUYADGBWSHF-UHFFFAOYSA-N 0.000 description 1
- 238000003325 tomography Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- 150000004654 triazenes Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- XPDWGBQVDMORPB-UHFFFAOYSA-N trifluoromethane acid Natural products FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 1
- 229960003223 tripelennamine Drugs 0.000 description 1
- 229960001128 triprolidine Drugs 0.000 description 1
- CBEQULMOCCWAQT-WOJGMQOQSA-N triprolidine Chemical compound C1=CC(C)=CC=C1C(\C=1N=CC=CC=1)=C/CN1CCCC1 CBEQULMOCCWAQT-WOJGMQOQSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 208000035408 type 1 diabetes mellitus 1 Diseases 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical group CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229960000653 valrubicin Drugs 0.000 description 1
- ZOCKGBMQLCSHFP-KQRAQHLDSA-N valrubicin Chemical compound O([C@H]1C[C@](CC2=C(O)C=3C(=O)C4=CC=CC(OC)=C4C(=O)C=3C(O)=C21)(O)C(=O)COC(=O)CCCC)[C@H]1C[C@H](NC(=O)C(F)(F)F)[C@H](O)[C@H](C)O1 ZOCKGBMQLCSHFP-KQRAQHLDSA-N 0.000 description 1
- 208000021331 vascular occlusion disease Diseases 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229940087652 vioxx Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 229950007802 zidometacin Drugs 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229960003414 zomepirac Drugs 0.000 description 1
- ZXVNMYWKKDOREA-UHFFFAOYSA-N zomepirac Chemical compound C1=C(CC(O)=O)N(C)C(C(=O)C=2C=CC(Cl)=CC=2)=C1C ZXVNMYWKKDOREA-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- 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
- A61K31/4965—Non-condensed pyrazines
- A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Liquid Crystal Substances (AREA)
- Glass Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762513010P | 2017-05-31 | 2017-05-31 | |
| US62/513,010 | 2017-05-31 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201902895A TW201902895A (zh) | 2019-01-16 |
| TWI781177B true TWI781177B (zh) | 2022-10-21 |
Family
ID=64456009
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW107118601A TWI781177B (zh) | 2017-05-31 | 2018-05-31 | 作為C5a抑制劑之6-5稠合環 |
Country Status (14)
| Country | Link |
|---|---|
| US (3) | US10562896B2 (enExample) |
| EP (1) | EP3630775B1 (enExample) |
| JP (1) | JP7141130B2 (enExample) |
| KR (1) | KR102638253B1 (enExample) |
| CN (1) | CN110997674B (enExample) |
| AR (1) | AR111983A1 (enExample) |
| AU (1) | AU2018277520B2 (enExample) |
| IL (1) | IL270828B2 (enExample) |
| MA (1) | MA48803A (enExample) |
| MX (1) | MX392259B (enExample) |
| NZ (1) | NZ759297A (enExample) |
| TW (1) | TWI781177B (enExample) |
| WO (1) | WO2018222598A1 (enExample) |
| ZA (1) | ZA201907746B (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7141129B2 (ja) | 2017-05-31 | 2022-09-22 | ケモセントリックス，インコーポレイティド | Ｃ５ａ阻害剤としての５－５融合環 |
| KR102638253B1 (ko) * | 2017-05-31 | 2024-02-16 | 케모센트릭스, 인크. | C5a 억제제로서의 6-5 융합 고리 |
| MA51327A (fr) | 2017-12-22 | 2021-05-26 | Chemocentryx Inc | Composés cycliques fusionnés en 5,5 à substitution diaryle, utilisés en tant qu'inhibiteurs du c5ar |
| MX2020006459A (es) | 2017-12-22 | 2020-11-06 | Chemocentryx Inc | Compuestos de anillos fusionados 6,5 diaril sustituidos como inhibidores de c5ar. |
| ES2993034T3 (en) * | 2018-04-02 | 2024-12-20 | Chemocentryx Inc | Prodrugs of fused-bicyclic c5ar antagonists |
| KR102890201B1 (ko) | 2019-07-10 | 2025-11-24 | 케모센트릭스, 인크. | Pd-l1 억제제로서의 인단 |
| CN112625036A (zh) | 2019-10-08 | 2021-04-09 | 上海海和药物研究开发股份有限公司 | 一类具有brd4抑制活性的化合物、其制备方法及用途 |
| ES3068390T3 (en) | 2019-10-16 | 2026-05-29 | Chemocentryx Inc | Heteroaryl-biphenyl amides for the treatment of pd-l1 diseases |
| AU2020368392B2 (en) | 2019-10-16 | 2026-01-08 | Chemocentryx, Inc. | Heteroaryl-biphenyl amines for the treatment of PD-L1 diseases |
| EP4178955A1 (en) | 2020-07-11 | 2023-05-17 | Pfizer Inc. | Antiviral heteroaryl ketone derivatives |
| US20220047592A1 (en) * | 2020-08-13 | 2022-02-17 | Chemocentryx, Inc. | METHODS OF TREATING RESPIRATORY DISEASES USING C5a INHIBITORS |
| US11351149B2 (en) | 2020-09-03 | 2022-06-07 | Pfizer Inc. | Nitrile-containing antiviral compounds |
| CA3192880A1 (en) | 2020-10-28 | 2022-05-05 | Chemocentryx, Inc. | Methods of treating hidradenitis suppurativa |
| CN112979646B (zh) * | 2021-03-08 | 2022-01-14 | 北京富龙康泰生物技术有限公司 | 一种咪唑并吡啶类衍生物 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040214856A1 (en) * | 2003-04-23 | 2004-10-28 | Pfizer Inc | Cannabinoid receptor ligands and uses thereof |
| US20130184253A1 (en) * | 2011-07-22 | 2013-07-18 | Novartis Ag | Tetrahydropyrido-pyridine and tetrahydropyrido-pyrimidine compounds and use thereof as c5a receptor modulators |
| TW201803850A (zh) * | 2016-04-04 | 2018-02-01 | 卡默森屈有限公司 | 可溶性C5aR拮抗劑 |
Family Cites Families (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK27383A (da) | 1982-02-17 | 1983-08-18 | Lepetit Spa | Fremgangsmaade til fremstilling af pyrazol(4,3-c)pyridiner |
| GB8613591D0 (en) | 1986-06-04 | 1986-07-09 | Roussel Lab Ltd | Chemical compounds |
| FR2761266B1 (fr) | 1997-03-28 | 1999-07-02 | Sanofi Sa | Composition pharmaceutique formee par granulation humide pour l'administration orale d'un derive du n-piperidino-3- pyrazolecarboxamide, de ses sels et de leurs solvates |
| CA2416527C (en) | 2000-08-10 | 2009-12-22 | Pharmacia Italia S.P.A. | Bicyclo-pyrazoles active as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them |
| AU7622500A (en) | 2000-09-29 | 2002-07-01 | Neurogen Corp | High affinity small molecule c5a receptor modulators |
| SE524438C2 (sv) | 2000-10-05 | 2004-08-10 | Magnus Georg Goertz | Fjärrstyrt dörrelaterat låsarrangemang, första och andra datorpogramprodukt, bärande medium och ett datorlösbart medium |
| US7902179B2 (en) | 2001-04-26 | 2011-03-08 | Ajinomoto Co., Inc. | Heterocyclic compounds |
| ITMI20012025A1 (it) | 2001-09-28 | 2003-03-28 | Dompe Spa | Sali di ammonio quaternari di omega-amminoalchilammidi di acidi r 2-aril-propionici e composizioni farmaceutiche che li contengono |
| WO2003082828A1 (en) | 2002-03-28 | 2003-10-09 | Neurogen Corporation | Substituted tetrahydroisoquinolines as c5a receptor modulators |
| CA2479928A1 (en) | 2002-03-28 | 2003-10-09 | Neurogen Corporation | Substituted biaryl amides as c5a receptor modulators |
| WO2003084524A1 (en) | 2002-03-29 | 2003-10-16 | Neurogen Corporation | Combination therapy for the treatment of conditions with pathogenic inflammatory components |
| WO2004016592A1 (en) * | 2002-08-14 | 2004-02-26 | Ppd Discovery, Inc. | Prenylation inhibitors and methods of their synthesis and use |
| US7169775B2 (en) | 2002-08-21 | 2007-01-30 | Neurogen Corporation | Amino methyl imidazoles as C5a receptor modulators |
| AU2003291403A1 (en) | 2002-11-08 | 2004-06-03 | Neurogen Corporation | 3-substituted-6-aryl pyridined as ligands of c5a receptors |
| US7145012B2 (en) | 2003-04-23 | 2006-12-05 | Pfizer Inc. | Cannabinoid receptor ligands and uses thereof |
| AU2003902354A0 (en) | 2003-05-15 | 2003-05-29 | Harkin, Denis W. | Treatment of haemorrhagic shock |
| US20060154917A1 (en) | 2003-07-03 | 2006-07-13 | Neurogen Corporation | Substituted (heterocycloalkyl)methyl azole derivatives as c5a receptor modulators |
| WO2006042102A2 (en) | 2004-10-05 | 2006-04-20 | Neurogen Corporation | Pyrrolo-pyridine, pyrrolo-pyrimidine and related heterocyclic compounds |
| EP1928461B1 (en) | 2005-08-04 | 2012-01-04 | Janssen Pharmaceutica NV | Pyrimidine compounds as serotonin receptor modulators |
| US7598255B2 (en) | 2005-08-04 | 2009-10-06 | Janssen Pharmaceutica Nv | Pyrimidine compounds as serotonin receptor modulators |
| US20070112015A1 (en) | 2005-10-28 | 2007-05-17 | Chemocentryx, Inc. | Substituted dihydropyridines and methods of use |
| US20080119457A1 (en) | 2006-08-24 | 2008-05-22 | Serenex, Inc. | Benzene, Pyridine, and Pyridazine Derivatives |
| PE20110063A1 (es) | 2008-06-20 | 2011-02-16 | Genentech Inc | DERIVADOS DE [1, 2, 4]TRIAZOLO[1, 5-a]PIRIDINA COMO INHIBIDORES DE JAK |
| US20110275639A1 (en) | 2008-12-22 | 2011-11-10 | Chemocentryx, Inc. | C5aR ANTAGONISTS |
| JP5819730B2 (ja) | 2008-12-22 | 2015-11-24 | ケモセントリックス，インコーポレイティド | Ｃ５ａＲアンタゴニスト |
| IN2012DN00721A (enExample) | 2009-09-02 | 2015-06-19 | Merck Sharp & Dohme | |
| DK2585064T3 (en) | 2010-06-24 | 2017-07-24 | Chemocentryx Inc | C5aR antagonists |
| PE20151139A1 (es) | 2012-08-16 | 2015-08-07 | Janssen Pharmaceutica Nv | Pirrolopirazoles como bloqueadores del canal de calcio tipo n |
| CN103421006B (zh) * | 2013-08-18 | 2016-06-22 | 上海师范大学 | 2,3,5,7-四取代二氢吡唑并六氢吡啶衍生物及其制备方法和应用 |
| GB201321746D0 (en) | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic agents |
| KR102638253B1 (ko) | 2017-05-31 | 2024-02-16 | 케모센트릭스, 인크. | C5a 억제제로서의 6-5 융합 고리 |
| JP7141129B2 (ja) | 2017-05-31 | 2022-09-22 | ケモセントリックス，インコーポレイティド | Ｃ５ａ阻害剤としての５－５融合環 |
| US10589871B2 (en) | 2017-09-25 | 2020-03-17 | Hamilton Sundstrand Corporation | Prognostic health monitoring and jam detection for use with an aircraft |
| MX2020006459A (es) | 2017-12-22 | 2020-11-06 | Chemocentryx Inc | Compuestos de anillos fusionados 6,5 diaril sustituidos como inhibidores de c5ar. |
| MA51327A (fr) | 2017-12-22 | 2021-05-26 | Chemocentryx Inc | Composés cycliques fusionnés en 5,5 à substitution diaryle, utilisés en tant qu'inhibiteurs du c5ar |
| ES2993034T3 (en) | 2018-04-02 | 2024-12-20 | Chemocentryx Inc | Prodrugs of fused-bicyclic c5ar antagonists |
-
2018
- 2018-05-29 KR KR1020197038669A patent/KR102638253B1/ko active Active
- 2018-05-29 NZ NZ759297A patent/NZ759297A/en unknown
- 2018-05-29 CN CN201880036662.0A patent/CN110997674B/zh active Active
- 2018-05-29 WO PCT/US2018/034905 patent/WO2018222598A1/en not_active Ceased
- 2018-05-29 US US15/991,703 patent/US10562896B2/en active Active
- 2018-05-29 AU AU2018277520A patent/AU2018277520B2/en active Active
- 2018-05-29 EP EP18809537.6A patent/EP3630775B1/en active Active
- 2018-05-29 MA MA048803A patent/MA48803A/fr unknown
- 2018-05-29 JP JP2019565833A patent/JP7141130B2/ja active Active
- 2018-05-29 MX MX2019014294A patent/MX392259B/es unknown
- 2018-05-31 TW TW107118601A patent/TWI781177B/zh active
- 2018-05-31 AR ARP180101449A patent/AR111983A1/es active IP Right Grant
-
2019
- 2019-11-21 IL IL270828A patent/IL270828B2/en unknown
- 2019-11-22 ZA ZA2019/07746A patent/ZA201907746B/en unknown
- 2019-12-20 US US16/723,433 patent/US11384079B2/en active Active
-
2022
- 2022-05-03 US US17/735,283 patent/US11773091B2/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040214856A1 (en) * | 2003-04-23 | 2004-10-28 | Pfizer Inc | Cannabinoid receptor ligands and uses thereof |
| US20130184253A1 (en) * | 2011-07-22 | 2013-07-18 | Novartis Ag | Tetrahydropyrido-pyridine and tetrahydropyrido-pyrimidine compounds and use thereof as c5a receptor modulators |
| TW201803850A (zh) * | 2016-04-04 | 2018-02-01 | 卡默森屈有限公司 | 可溶性C5aR拮抗劑 |
Also Published As
| Publication number | Publication date |
|---|---|
| TW201902895A (zh) | 2019-01-16 |
| MX392259B (es) | 2025-03-24 |
| JP7141130B2 (ja) | 2022-09-22 |
| EP3630775A4 (en) | 2020-10-07 |
| MA48803A (fr) | 2020-04-08 |
| WO2018222598A1 (en) | 2018-12-06 |
| KR20200015604A (ko) | 2020-02-12 |
| CA3064017A1 (en) | 2018-12-06 |
| CN110997674B (zh) | 2022-12-20 |
| RU2019142942A3 (enExample) | 2021-09-03 |
| AU2018277520B2 (en) | 2022-03-17 |
| US10562896B2 (en) | 2020-02-18 |
| US11773091B2 (en) | 2023-10-03 |
| EP3630775B1 (en) | 2022-12-14 |
| NZ759297A (en) | 2026-03-27 |
| US20230151002A1 (en) | 2023-05-18 |
| IL270828B2 (en) | 2023-04-01 |
| AR111983A1 (es) | 2019-09-11 |
| CN110997674A (zh) | 2020-04-10 |
| US20180370967A1 (en) | 2018-12-27 |
| IL270828A (en) | 2020-01-30 |
| KR102638253B1 (ko) | 2024-02-16 |
| BR112019025049A2 (pt) | 2020-06-16 |
| IL270828B (en) | 2022-12-01 |
| ZA201907746B (en) | 2023-10-25 |
| US11384079B2 (en) | 2022-07-12 |
| EP3630775A1 (en) | 2020-04-08 |
| AU2018277520A1 (en) | 2019-12-12 |
| JP2020522484A (ja) | 2020-07-30 |
| RU2019142942A (ru) | 2021-06-30 |
| US20200347049A1 (en) | 2020-11-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US11773091B2 (en) | 6-5 fused rings as C5a inhibitors | |
| TWI789470B (zh) | 作為C5aR抑制劑之經二芳基取代之6,5-稠合環化合物 | |
| TWI813570B (zh) | 作為C5a抑制劑之5-5稠合環 | |
| CA2893597A1 (en) | Diazole lactams | |
| RU2780338C2 (ru) | 6-5 КОНДЕНСИРОВАННЫЕ КОЛЬЦА КАК ИНГИБИТОРЫ С5а | |
| CA3064017C (en) | 6-5 fused rings as c5a inhibitors | |
| HK40026727B (en) | 6-5 fused rings as c5a inhibitors | |
| HK40026727A (en) | 6-5 fused rings as c5a inhibitors | |
| BR122024024491B1 (pt) | Método in vitro para inibir a quimiotaxia celular mediada por c5a | |
| RU2780322C2 (ru) | 5-5 КОНДЕНСИРОВАННЫЕ КОЛЬЦА КАК ИНГИБИТОРЫ С5а | |
| BR112019025049B1 (pt) | Compostos com anéis 6- 5 fundidos e composição farmacêutica que os compreende | |
| BR122024024491A2 (pt) | Compostos com anéis 6- 5 fundidos, composição farmacêutica, seus usos como inibidores de c5a e método in vitro para inibir a quimiotaxia celular mediada por c5a | |
| HK40026719A (en) | 5-5 fused rings as c5a inhibitors | |
| HK40026719B (en) | 5-5 fused rings as c5a inhibitors |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| GD4A | Issue of patent certificate for granted invention patent |