SK282409B6 - Heterocyklické kyseliny, ich použitie na výrobu farmaceutických prostriedkov a farmaceutický prostriedok s ich obsahom - Google Patents

Info

Publication number

SK282409B6

SK282409B6 SK822-95A SK82295A SK282409B6 SK 282409 B6 SK282409 B6 SK 282409B6 SK 82295 A SK82295 A SK 82295A SK 282409 B6 SK282409 B6 SK 282409B6

Authority

SK

Slovakia

Prior art keywords

formula

atom

alkyl

cycloalkyl

mmol

Prior art date

1992-12-22

Links

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• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 25
• 125000000623 heterocyclic group Chemical group 0.000 title claims abstract description 17
• 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
• 150000001875 compounds Chemical class 0.000 claims abstract description 217
• 150000003839 salts Chemical class 0.000 claims abstract description 33
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 19
• 150000002617 leukotrienes Chemical class 0.000 claims abstract description 16
• 229910052760 oxygen Chemical group 0.000 claims abstract description 15
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 14
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 13
• 239000001301 oxygen Chemical group 0.000 claims abstract description 13
• 239000011593 sulfur Substances 0.000 claims abstract description 13
• 239000001257 hydrogen Substances 0.000 claims abstract description 12
• 208000006673 asthma Diseases 0.000 claims abstract description 11
• 125000005843 halogen group Chemical group 0.000 claims abstract description 11
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
• 150000002367 halogens Chemical class 0.000 claims abstract description 6
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 271
• -1 (Methanesulfonyl) oxy Chemical group 0.000 claims description 147
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 124
• 239000000203 mixture Substances 0.000 claims description 108
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 98
• 238000000034 method Methods 0.000 claims description 77
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 75
• 238000005160 1H NMR spectroscopy Methods 0.000 claims description 68
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 63
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 51
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 48
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 42
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 40
• 239000002253 acid Substances 0.000 claims description 40
• 125000004432 carbon atom Chemical group C* 0.000 claims description 40
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 39
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
• 239000000741 silica gel Substances 0.000 claims description 34
• 229910002027 silica gel Inorganic materials 0.000 claims description 34
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 32
• 238000003818 flash chromatography Methods 0.000 claims description 32
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 29
• 125000000217 alkyl group Chemical group 0.000 claims description 29
• 239000011734 sodium Substances 0.000 claims description 29
• OQFHCJMOQCAFIL-UHFFFAOYSA-N acetic acid;cyclopropane Chemical compound C1CC1.CC(O)=O OQFHCJMOQCAFIL-UHFFFAOYSA-N 0.000 claims description 28
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 27
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 27
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
• 229910052938 sodium sulfate Inorganic materials 0.000 claims description 27
• 235000011152 sodium sulphate Nutrition 0.000 claims description 27
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 26
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 25
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 24
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 23
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
• 239000002904 solvent Substances 0.000 claims description 23
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 20
• 229910052757 nitrogen Inorganic materials 0.000 claims description 19
• 239000004480 active ingredient Substances 0.000 claims description 17
• 239000000725 suspension Substances 0.000 claims description 17
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
• 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 15
• 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 15
• 125000004122 cyclic group Chemical group 0.000 claims description 14
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 13
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 13
• 125000003342 alkenyl group Chemical group 0.000 claims description 13
• 229920006395 saturated elastomer Polymers 0.000 claims description 13
• 239000007787 solid Substances 0.000 claims description 12
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 11
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 10
• 235000019270 ammonium chloride Nutrition 0.000 claims description 10
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 10
• 235000017557 sodium bicarbonate Nutrition 0.000 claims description 10
• 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 10
• 238000010521 absorption reaction Methods 0.000 claims description 9
• 125000000304 alkynyl group Chemical group 0.000 claims description 9
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 claims description 8
• 238000004458 analytical method Methods 0.000 claims description 8
• 229930195733 hydrocarbon Natural products 0.000 claims description 8
• 150000002430 hydrocarbons Chemical group 0.000 claims description 8
• 238000010992 reflux Methods 0.000 claims description 8
• 239000012359 Methanesulfonyl chloride Substances 0.000 claims description 7
• 230000015572 biosynthetic process Effects 0.000 claims description 7
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 7
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
• 239000004215 Carbon black (E152) Substances 0.000 claims description 6
• 229910052799 carbon Inorganic materials 0.000 claims description 6
• 239000003814 drug Substances 0.000 claims description 6
• 125000005842 heteroatom Chemical group 0.000 claims description 6
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
• 241000124008 Mammalia Species 0.000 claims description 5
• 239000000730 antalgic agent Substances 0.000 claims description 5
• 125000004429 atom Chemical group 0.000 claims description 5
• 239000003112 inhibitor Substances 0.000 claims description 5
• 239000003199 leukotriene receptor blocking agent Substances 0.000 claims description 5
• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 4
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 230000000694 effects Effects 0.000 claims description 4
• 235000002906 tartaric acid Nutrition 0.000 claims description 4
• 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 4
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 208000030533 eye disease Diseases 0.000 claims description 3
• 125000002950 monocyclic group Chemical group 0.000 claims description 3
• 239000011975 tartaric acid Substances 0.000 claims description 3
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
• NVXPSQIYZCKHMN-UHFFFAOYSA-N 2-methyl-[1,3]thiazolo[5,4-b]pyridine Chemical compound C1=CN=C2SC(C)=NC2=C1 NVXPSQIYZCKHMN-UHFFFAOYSA-N 0.000 claims description 2
• 125000002015 acyclic group Chemical group 0.000 claims description 2
• 239000005557 antagonist Substances 0.000 claims description 2
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
• 230000002093 peripheral effect Effects 0.000 claims description 2
• 239000002089 prostaglandin antagonist Substances 0.000 claims description 2
• 239000012279 sodium borohydride Substances 0.000 claims description 2
• 229910000033 sodium borohydride Inorganic materials 0.000 claims description 2
• 125000004434 sulfur atom Chemical group 0.000 claims description 2
• 229930192474 thiophene Natural products 0.000 claims description 2
• 230000002757 inflammatory effect Effects 0.000 claims 2
• ZDOWDSFTSWTBEV-UHFFFAOYSA-N (2-methyl-[1,3]thiazolo[5,4-b]pyridin-5-yl)methanol Chemical compound C1=C(CO)N=C2SC(C)=NC2=C1 ZDOWDSFTSWTBEV-UHFFFAOYSA-N 0.000 claims 1
• 101000986989 Naja kaouthia Acidic phospholipase A2 CM-II Proteins 0.000 claims 1
• 125000002252 acyl group Chemical group 0.000 claims 1
• 229940125715 antihistaminic agent Drugs 0.000 claims 1
• 239000000739 antihistaminic agent Substances 0.000 claims 1
• DPLCAYUXXMMIRA-UHFFFAOYSA-N methanesulfonate triphenylphosphanium Chemical compound CS([O-])(=O)=O.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 DPLCAYUXXMMIRA-UHFFFAOYSA-N 0.000 claims 1
• 239000002599 prostaglandin synthase inhibitor Substances 0.000 claims 1
• 239000002464 receptor antagonist Substances 0.000 claims 1
• 229940044551 receptor antagonist Drugs 0.000 claims 1
• 238000001665 trituration Methods 0.000 claims 1
• 230000001120 cytoprotective effect Effects 0.000 abstract description 9
• 125000001424 substituent group Chemical group 0.000 abstract description 7
• 206010020751 Hypersensitivity Diseases 0.000 abstract description 5
• 230000009471 action Effects 0.000 abstract description 5
• 230000007815 allergy Effects 0.000 abstract description 4
• 230000004968 inflammatory condition Effects 0.000 abstract description 4
• 206010002383 Angina Pectoris Diseases 0.000 abstract description 3
• 208000007101 Muscle Cramp Diseases 0.000 abstract description 3
• 208000005392 Spasm Diseases 0.000 abstract description 3
• 230000002490 cerebral effect Effects 0.000 abstract description 3
• 208000006454 hepatitis Diseases 0.000 abstract description 3
• 231100000283 hepatitis Toxicity 0.000 abstract description 3
• 208000037487 Endotoxemia Diseases 0.000 abstract description 2
• 206010052779 Transplant rejections Diseases 0.000 abstract description 2
• 125000004093 cyano group Chemical group *C#N 0.000 abstract description 2
• 201000008383 nephritis Diseases 0.000 abstract description 2
• 150000002431 hydrogen Chemical class 0.000 abstract 1
• 239000000243 solution Substances 0.000 description 154
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 28
• 238000006243 chemical reaction Methods 0.000 description 28
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
• 239000000460 chlorine Substances 0.000 description 26
• 239000000047 product Substances 0.000 description 24
• 239000000427 antigen Substances 0.000 description 22
• 102000036639 antigens Human genes 0.000 description 22
• 108091007433 antigens Proteins 0.000 description 22
• 229910052708 sodium Inorganic materials 0.000 description 22
• 229940083542 sodium Drugs 0.000 description 22
• 239000000126 substance Substances 0.000 description 20
• USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 17
• 239000005695 Ammonium acetate Substances 0.000 description 17
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 17
• 229940043376 ammonium acetate Drugs 0.000 description 17
• 235000019257 ammonium acetate Nutrition 0.000 description 17
• JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 16
• 238000012360 testing method Methods 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 15
• 238000001704 evaporation Methods 0.000 description 15
• 230000008020 evaporation Effects 0.000 description 15
• 239000011541 reaction mixture Substances 0.000 description 15
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 14
• 239000000443 aerosol Substances 0.000 description 14
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 14
• NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 14
• 239000003921 oil Substances 0.000 description 14
• 229910052801 chlorine Inorganic materials 0.000 description 13
• 238000001816 cooling Methods 0.000 description 12
• 239000000284 extract Substances 0.000 description 12
• 238000002360 preparation method Methods 0.000 description 12
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
• UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 11
• 241000700159 Rattus Species 0.000 description 10
• 150000001299 aldehydes Chemical class 0.000 description 10
• SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 10
• 238000004587 chromatography analysis Methods 0.000 description 10
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Substances CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 10
• 150000002148 esters Chemical class 0.000 description 10
• 229910052731 fluorine Inorganic materials 0.000 description 10
• 150000004702 methyl esters Chemical class 0.000 description 10
• 229960000583 acetic acid Drugs 0.000 description 9
• 150000007513 acids Chemical class 0.000 description 9
• 230000000202 analgesic effect Effects 0.000 description 9
• 230000003110 anti-inflammatory effect Effects 0.000 description 9
• 229910052794 bromium Inorganic materials 0.000 description 9
• 238000002474 experimental method Methods 0.000 description 9
• 150000004714 phosphonium salts Chemical class 0.000 description 9
• 238000003756 stirring Methods 0.000 description 9
• 239000003826 tablet Substances 0.000 description 9
• 241001494479 Pecora Species 0.000 description 8
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
• 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 8
• 150000003254 radicals Chemical class 0.000 description 8
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
• WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 8
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
• 239000002775 capsule Substances 0.000 description 7
• 239000003795 chemical substances by application Substances 0.000 description 7
• 239000000706 filtrate Substances 0.000 description 7
• 229910052744 lithium Inorganic materials 0.000 description 7
• 210000004072 lung Anatomy 0.000 description 7
• 230000003637 steroidlike Effects 0.000 description 7
• CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 7
• YRIZYWQGELRKNT-UHFFFAOYSA-N 1,3,5-trichloro-1,3,5-triazinane-2,4,6-trione Chemical compound ClN1C(=O)N(Cl)C(=O)N(Cl)C1=O YRIZYWQGELRKNT-UHFFFAOYSA-N 0.000 description 6
• MXCOXRCQSNVLRE-UHFFFAOYSA-M C(C)(=O)[O-].[Na+].C1CC1 Chemical compound C(C)(=O)[O-].[Na+].C1CC1 MXCOXRCQSNVLRE-UHFFFAOYSA-M 0.000 description 6
• 241001465754 Metazoa Species 0.000 description 6
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
• 201000010099 disease Diseases 0.000 description 6
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
• KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 6
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
• 235000019341 magnesium sulphate Nutrition 0.000 description 6
• 239000003960 organic solvent Substances 0.000 description 6
• 239000000843 powder Substances 0.000 description 6
• ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 6
• 230000004044 response Effects 0.000 description 6
• 229950009390 symclosene Drugs 0.000 description 6
• DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical compound C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 description 6
• 229940125670 thienopyridine Drugs 0.000 description 6
• 239000002175 thienopyridine Substances 0.000 description 6
• AVCVDUDESCZFHJ-UHFFFAOYSA-N triphenylphosphane;hydrochloride Chemical compound [Cl-].C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 AVCVDUDESCZFHJ-UHFFFAOYSA-N 0.000 description 6
• 241000244188 Ascaris suum Species 0.000 description 5
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 5
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
• 241000282693 Cercopithecidae Species 0.000 description 5
• 241000282412 Homo Species 0.000 description 5
• 206010061218 Inflammation Diseases 0.000 description 5
• 229910000085 borane Inorganic materials 0.000 description 5
• 230000006378 damage Effects 0.000 description 5
• 239000002552 dosage form Substances 0.000 description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
• 238000001914 filtration Methods 0.000 description 5
• 230000004054 inflammatory process Effects 0.000 description 5
• 239000006199 nebulizer Substances 0.000 description 5
• DRFVFUCINMEBEQ-UHFFFAOYSA-N perchloryl hypofluorite Chemical compound FOCl(=O)(=O)=O DRFVFUCINMEBEQ-UHFFFAOYSA-N 0.000 description 5
• CWBYTSQAVGCXFW-UHFFFAOYSA-N thieno[3,2-b]pyridine-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2SC=CC2=N1 CWBYTSQAVGCXFW-UHFFFAOYSA-N 0.000 description 5
• QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 description 4
• KVVDRQDTODKIJD-UHFFFAOYSA-N 2-cyclopropylacetic acid Chemical compound OC(=O)CC1CC1 KVVDRQDTODKIJD-UHFFFAOYSA-N 0.000 description 4
• KAEJOFFKIBBRHI-UHFFFAOYSA-N 2-fluorothieno[3,2-b]pyridine Chemical compound C1=CC=C2SC(F)=CC2=N1 KAEJOFFKIBBRHI-UHFFFAOYSA-N 0.000 description 4
• FLWXYOZWTCSAQC-UHFFFAOYSA-N 5-methylthieno[3,2-b]pyridine Chemical compound CC1=CC=C2SC=CC2=N1 FLWXYOZWTCSAQC-UHFFFAOYSA-N 0.000 description 4
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