KR19990083234A - 치환된 삼환식 화합물 - Google Patents

Info

Publication number

KR19990083234A

KR19990083234A KR1019990013439A KR19990013439A KR19990083234A KR 19990083234 A KR19990083234 A KR 19990083234A KR 1019990013439 A KR1019990013439 A KR 1019990013439A KR 19990013439 A KR19990013439 A KR 19990013439A KR 19990083234 A KR19990083234 A KR 19990083234A

Authority

KR

South Korea

Prior art keywords

alkyl

phenyl

arthritis

formula

nitrogen

Prior art date

1998-04-17

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Withdrawn

Links

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• 150000001875 compounds Chemical class 0.000 claims abstract description 127
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 32
• 238000011282 treatment Methods 0.000 claims abstract description 32
• 201000010099 disease Diseases 0.000 claims abstract description 28
• 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 14
• 239000000194 fatty acid Substances 0.000 claims abstract description 14
• 229930195729 fatty acid Natural products 0.000 claims abstract description 14
• 150000004665 fatty acids Chemical class 0.000 claims abstract description 14
• 230000001404 mediated effect Effects 0.000 claims abstract description 13
• 206010040070 Septic Shock Diseases 0.000 claims abstract description 10
• 230000036303 septic shock Effects 0.000 claims abstract description 10
• -1 phenoxy Phenyl Chemical group 0.000 claims description 125
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 109
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 101
• 239000002253 acid Substances 0.000 claims description 83
• 229910052757 nitrogen Inorganic materials 0.000 claims description 58
• 125000005843 halogen group Chemical group 0.000 claims description 44
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 42
• 229910052739 hydrogen Inorganic materials 0.000 claims description 40
• 239000001257 hydrogen Substances 0.000 claims description 40
• 206010003246 arthritis Diseases 0.000 claims description 39
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 34
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
• 238000000034 method Methods 0.000 claims description 33
• 125000000217 alkyl group Chemical group 0.000 claims description 30
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 30
• 229910052760 oxygen Inorganic materials 0.000 claims description 29
• 125000001424 substituent group Chemical group 0.000 claims description 29
• 229910052717 sulfur Inorganic materials 0.000 claims description 29
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 28
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 28
• 229910052799 carbon Inorganic materials 0.000 claims description 28
• 239000001301 oxygen Substances 0.000 claims description 28
• 239000011593 sulfur Substances 0.000 claims description 28
• 230000002452 interceptive effect Effects 0.000 claims description 27
• 125000004076 pyridyl group Chemical group 0.000 claims description 26
• 150000003839 salts Chemical class 0.000 claims description 25
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 20
• YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 claims description 20
• 125000005647 linker group Chemical group 0.000 claims description 20
• 125000005037 alkyl phenyl group Chemical group 0.000 claims description 18
• 239000000651 prodrug Substances 0.000 claims description 18
• 229940002612 prodrug Drugs 0.000 claims description 18
• 241000124008 Mammalia Species 0.000 claims description 17
• 125000000623 heterocyclic group Chemical group 0.000 claims description 17
• 201000008482 osteoarthritis Diseases 0.000 claims description 17
• 125000005842 heteroatom Chemical group 0.000 claims description 15
• 125000001544 thienyl group Chemical group 0.000 claims description 13
• 206010006451 bronchitis Diseases 0.000 claims description 12
• 125000002541 furyl group Chemical group 0.000 claims description 12
• 230000003287 optical effect Effects 0.000 claims description 12
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 11
• 230000002401 inhibitory effect Effects 0.000 claims description 11
• 230000005764 inhibitory process Effects 0.000 claims description 11
• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 11
• 229940114079 arachidonic acid Drugs 0.000 claims description 10
• 235000021342 arachidonic acid Nutrition 0.000 claims description 10
• 125000004429 atom Chemical group 0.000 claims description 10
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
• 208000002574 reactive arthritis Diseases 0.000 claims description 10
• 239000012453 solvate Substances 0.000 claims description 10
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 9
• 208000014674 injury Diseases 0.000 claims description 9
• 206010006448 Bronchiolitis Diseases 0.000 claims description 8
• 208000004575 Infectious Arthritis Diseases 0.000 claims description 8
• 206010033645 Pancreatitis Diseases 0.000 claims description 8
• 208000006673 asthma Diseases 0.000 claims description 8
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 8
• 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 7
• RERZNCLIYCABFS-UHFFFAOYSA-N harmaline Chemical compound C1CN=C(C)C2=C1C1=CC=C(OC)C=C1N2 RERZNCLIYCABFS-UHFFFAOYSA-N 0.000 claims description 7
• 125000001624 naphthyl group Chemical group 0.000 claims description 7
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 7
• 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 6
• 206010006458 Bronchitis chronic Diseases 0.000 claims description 6
• 201000003883 Cystic fibrosis Diseases 0.000 claims description 6
• 201000005569 Gout Diseases 0.000 claims description 6
• 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 6
• 206010040047 Sepsis Diseases 0.000 claims description 6
• 208000006011 Stroke Diseases 0.000 claims description 6
• 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 6
• 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 6
• 125000003342 alkenyl group Chemical group 0.000 claims description 6
• 125000004414 alkyl thio group Chemical group 0.000 claims description 6
• 208000007451 chronic bronchitis Diseases 0.000 claims description 6
• 230000001684 chronic effect Effects 0.000 claims description 6
• 239000003085 diluting agent Substances 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims description 6
• 208000030603 inherited susceptibility to asthma Diseases 0.000 claims description 6
• 230000001575 pathological effect Effects 0.000 claims description 6
• 230000035939 shock Effects 0.000 claims description 6
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 5
• 206010039085 Rhinitis allergic Diseases 0.000 claims description 5
• 125000000304 alkynyl group Chemical group 0.000 claims description 5
• 201000010105 allergic rhinitis Diseases 0.000 claims description 5
• 239000011575 calcium Substances 0.000 claims description 5
• 229910052791 calcium Inorganic materials 0.000 claims description 5
• KYZMWHSKQSAKMW-UHFFFAOYSA-N methyl 10-benzyl-4-methoxy-6,7,8,9-tetrahydropyrido[1,2-a]indole-6-carboxylate Chemical compound C12=CC=CC(OC)=C2N2C(C(=O)OC)CCCC2=C1CC1=CC=CC=C1 KYZMWHSKQSAKMW-UHFFFAOYSA-N 0.000 claims description 5
• 230000008733 trauma Effects 0.000 claims description 5
• YKFOLURXVRADNC-UHFFFAOYSA-N 2-[(2,9-dibenzyl-4-carbamoyl-3,4-dihydro-1h-pyrido[3,4-b]indol-5-yl)oxy]acetic acid Chemical compound C1C(N(C2=CC=CC(OCC(O)=O)=C22)CC=3C=CC=CC=3)=C2C(C(=O)N)CN1CC1=CC=CC=C1 YKFOLURXVRADNC-UHFFFAOYSA-N 0.000 claims description 4
• MHXZVTNDXLWWNN-UHFFFAOYSA-N 2-[(9-benzyl-1-carbamoyl-3,4-dihydro-2h-pyrido[2,3-b]indol-8-yl)oxy]acetic acid Chemical compound NC(=O)N1CCCC(C2=CC=CC(OCC(O)=O)=C22)=C1N2CC1=CC=CC=C1 MHXZVTNDXLWWNN-UHFFFAOYSA-N 0.000 claims description 4
• 206010000599 Acromegaly Diseases 0.000 claims description 4
• 206010003256 Arthritis gonococcal Diseases 0.000 claims description 4
• 206010003267 Arthritis reactive Diseases 0.000 claims description 4
• 206010003274 Arthritis viral Diseases 0.000 claims description 4
• 206010006811 Bursitis Diseases 0.000 claims description 4
• 201000011275 Epicondylitis Diseases 0.000 claims description 4
• 206010016207 Familial Mediterranean fever Diseases 0.000 claims description 4
• 206010017533 Fungal infection Diseases 0.000 claims description 4
• 208000018565 Hemochromatosis Diseases 0.000 claims description 4
• 102000001554 Hemoglobins Human genes 0.000 claims description 4
• 108010054147 Hemoglobins Proteins 0.000 claims description 4
• 208000031226 Hyperlipidaemia Diseases 0.000 claims description 4
• 208000012659 Joint disease Diseases 0.000 claims description 4
• 208000016604 Lyme disease Diseases 0.000 claims description 4
• 208000000112 Myalgia Diseases 0.000 claims description 4
• 206010036030 Polyarthritis Diseases 0.000 claims description 4
• 206010065159 Polychondritis Diseases 0.000 claims description 4
• 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 4
• 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 4
• 206010037549 Purpura Diseases 0.000 claims description 4
• 241001672981 Purpura Species 0.000 claims description 4
• 206010037660 Pyrexia Diseases 0.000 claims description 4
• 201000002661 Spondylitis Diseases 0.000 claims description 4
• 208000002240 Tennis Elbow Diseases 0.000 claims description 4
• 208000027418 Wounds and injury Diseases 0.000 claims description 4
• 208000021240 acute bronchiolitis Diseases 0.000 claims description 4
• 210000004369 blood Anatomy 0.000 claims description 4
• 239000008280 blood Substances 0.000 claims description 4
• 230000006378 damage Effects 0.000 claims description 4
• 208000035475 disorder Diseases 0.000 claims description 4
• 208000024386 fungal infectious disease Diseases 0.000 claims description 4
• 230000002008 hemorrhagic effect Effects 0.000 claims description 4
• 208000020346 hyperlipoproteinemia Diseases 0.000 claims description 4
• 230000001969 hypertrophic effect Effects 0.000 claims description 4
• 230000002458 infectious effect Effects 0.000 claims description 4
• 208000030428 polyarticular arthritis Diseases 0.000 claims description 4
• 230000000306 recurrent effect Effects 0.000 claims description 4
• 201000001223 septic arthritis Diseases 0.000 claims description 4
• 208000007056 sickle cell anemia Diseases 0.000 claims description 4
• 208000006379 syphilis Diseases 0.000 claims description 4
• 201000008827 tuberculosis Diseases 0.000 claims description 4
• 208000034624 Leukocytoclastic Cutaneous Vasculitis Diseases 0.000 claims description 3
• 208000032514 Leukocytoclastic vasculitis Diseases 0.000 claims description 3
• 108010031873 Secretory Phospholipases A2 Proteins 0.000 claims description 3
• 208000006045 Spondylarthropathies Diseases 0.000 claims description 3
• 201000006362 hypersensitivity vasculitis Diseases 0.000 claims description 3
• 201000005671 spondyloarthropathy Diseases 0.000 claims description 3
• 231100000331 toxic Toxicity 0.000 claims description 3
• 230000002588 toxic effect Effects 0.000 claims description 3
• 206010008690 Chondrocalcinosis pyrophosphate Diseases 0.000 claims description 2
• 208000033464 Reiter syndrome Diseases 0.000 claims description 2
• 102000005473 Secretory Phospholipases A2 Human genes 0.000 claims description 2
• 208000002849 chondrocalcinosis Diseases 0.000 claims description 2
• 208000011580 syndromic disease Diseases 0.000 claims 8
• 208000003456 Juvenile Arthritis Diseases 0.000 claims 3
• 206010059176 Juvenile idiopathic arthritis Diseases 0.000 claims 3
• 208000017442 Retinal disease Diseases 0.000 claims 3
• 206010038923 Retinopathy Diseases 0.000 claims 3
• 210000003797 carpal joint Anatomy 0.000 claims 3
• 208000003906 hydrocephalus Diseases 0.000 claims 3
• 150000002431 hydrogen Chemical class 0.000 claims 3
• 201000000596 systemic lupus erythematosus Diseases 0.000 claims 3
• 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 claims 2
• 201000002980 Hyperparathyroidism Diseases 0.000 claims 2
• 206010021143 Hypoxia Diseases 0.000 claims 2
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
• 230000006907 apoptotic process Effects 0.000 claims 2
• 230000007954 hypoxia Effects 0.000 claims 2
• 238000004519 manufacturing process Methods 0.000 claims 2
• 201000001119 neuropathy Diseases 0.000 claims 2
• 230000007823 neuropathy Effects 0.000 claims 2
• 208000033808 peripheral neuropathy Diseases 0.000 claims 2
• 206010054834 Hypergonadism Diseases 0.000 claims 1
• 206010020751 Hypersensitivity Diseases 0.000 claims 1
• 206010041591 Spinal osteoarthritis Diseases 0.000 claims 1
• 208000026935 allergic disease Diseases 0.000 claims 1
• 230000000172 allergic effect Effects 0.000 claims 1
• 208000010668 atopic eczema Diseases 0.000 claims 1
• 230000008021 deposition Effects 0.000 claims 1
• 230000009610 hypersensitivity Effects 0.000 claims 1
• 201000004990 juvenile ankylosing spondylitis Diseases 0.000 claims 1
• 230000002981 neuropathic effect Effects 0.000 claims 1
• 206010039083 rhinitis Diseases 0.000 claims 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 270
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 121
• 229960000583 acetic acid Drugs 0.000 description 94
• 239000000243 solution Substances 0.000 description 87
• 125000001041 indolyl group Chemical group 0.000 description 83
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
• 239000000203 mixture Substances 0.000 description 75
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 61
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 54
• 238000002360 preparation method Methods 0.000 description 49
• 239000000047 product Substances 0.000 description 44
• 235000019439 ethyl acetate Nutrition 0.000 description 43
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
• 239000007787 solid Substances 0.000 description 33
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 32
• 239000011541 reaction mixture Substances 0.000 description 30
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
• 238000006243 chemical reaction Methods 0.000 description 25
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 24
• 238000000921 elemental analysis Methods 0.000 description 24
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 24
• SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 23
• 150000003254 radicals Chemical class 0.000 description 23
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
• 239000012267 brine Substances 0.000 description 22
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 22
• 150000002148 esters Chemical class 0.000 description 21
• 239000003921 oil Substances 0.000 description 20
• 150000001408 amides Chemical class 0.000 description 19
• 239000012044 organic layer Substances 0.000 description 19
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 18
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
• 239000000741 silica gel Substances 0.000 description 18
• 229910002027 silica gel Inorganic materials 0.000 description 18
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
• 239000004480 active ingredient Substances 0.000 description 16
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• 210000001519 tissue Anatomy 0.000 description 16
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• 229910052938 sodium sulfate Inorganic materials 0.000 description 15
• 235000011152 sodium sulphate Nutrition 0.000 description 15
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 14
• 239000002904 solvent Substances 0.000 description 14
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
• 238000009472 formulation Methods 0.000 description 13
• 239000011734 sodium Substances 0.000 description 13
• 239000003826 tablet Substances 0.000 description 13
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
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• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 12
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 11
• 229920002472 Starch Polymers 0.000 description 11
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 11
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
• 229910000104 sodium hydride Inorganic materials 0.000 description 11
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• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 11
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• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
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• PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 10
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• JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 10
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• 239000000463 material Substances 0.000 description 9
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• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
• 229910004298 SiO 2 Inorganic materials 0.000 description 8
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
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• 238000004949 mass spectrometry Methods 0.000 description 8
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• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 7
• 125000003118 aryl group Chemical group 0.000 description 7
• 238000003556 assay Methods 0.000 description 7
• 239000002775 capsule Substances 0.000 description 7
• 238000000434 field desorption mass spectrometry Methods 0.000 description 7
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• 239000012442 inert solvent Substances 0.000 description 7
• 235000019359 magnesium stearate Nutrition 0.000 description 7
• IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 7
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• 229940079593 drug Drugs 0.000 description 6
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• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
• 239000004615 ingredient Substances 0.000 description 6
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• 239000002002 slurry Substances 0.000 description 6
• 239000007921 spray Substances 0.000 description 6
• VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 6
• LUNOXNMCFPFPMO-UHFFFAOYSA-N 4-methoxy-1h-indole Chemical compound COC1=CC=CC2=C1C=CN2 LUNOXNMCFPFPMO-UHFFFAOYSA-N 0.000 description 5
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