CA2138631A1 - 6,8-dioxabicyclo¬3.2.1|octanes utilises comme inhibiteurs de la biosynthese de la leukotriene - Google Patents

Info

Publication number

CA2138631A1

CA2138631A1 CA 2138631 CA2138631A CA2138631A1 CA 2138631 A1 CA2138631 A1 CA 2138631A1 CA 2138631 CA2138631 CA 2138631 CA 2138631 A CA2138631 A CA 2138631A CA 2138631 A1 CA2138631 A1 CA 2138631A1

Authority

CA

Canada

Prior art keywords

lower alkyl

naphthol

hydroxy

mixture

mmol

Prior art date

1993-12-28

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

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 230000015572 biosynthetic process Effects 0.000 title claims abstract description 24
• 150000002617 leukotrienes Chemical class 0.000 title claims abstract description 19
• 239000003112 inhibitor Substances 0.000 title claims abstract description 11
• 150000001875 compounds Chemical class 0.000 claims abstract description 162
• 238000000034 method Methods 0.000 claims description 84
• UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 66
• 125000000217 alkyl group Chemical group 0.000 claims description 63
• 229920006395 saturated elastomer Polymers 0.000 claims description 27
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 22
• 150000003839 salts Chemical class 0.000 claims description 22
• 125000003545 alkoxy group Chemical group 0.000 claims description 20
• 125000004414 alkyl thio group Chemical group 0.000 claims description 19
• 125000003118 aryl group Chemical group 0.000 claims description 19
• 239000004480 active ingredient Substances 0.000 claims description 18
• 229910052717 sulfur Inorganic materials 0.000 claims description 18
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 16
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
• 125000004432 carbon atom Chemical group C* 0.000 claims description 10
• 239000008194 pharmaceutical composition Substances 0.000 claims description 9
• 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 8
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 7
• 239000000730 antalgic agent Substances 0.000 claims description 7
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 229910052736 halogen Inorganic materials 0.000 claims description 7
• 150000002367 halogens Chemical class 0.000 claims description 7
• 229910052757 nitrogen Inorganic materials 0.000 claims description 7
• 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 238000003786 synthesis reaction Methods 0.000 claims description 6
• 230000009471 action Effects 0.000 claims description 5
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 5
• 150000001413 amino acids Chemical group 0.000 claims description 5
• 208000006673 asthma Diseases 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
• ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 claims description 4
• GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical compound OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 claims description 4
• CVQUWLDCFXOXEN-UHFFFAOYSA-N Pyran-4-one Chemical compound O=C1C=COC=C1 CVQUWLDCFXOXEN-UHFFFAOYSA-N 0.000 claims description 4
• UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 4
• 125000000732 arylene group Chemical group 0.000 claims description 3
• 125000002619 bicyclic group Chemical group 0.000 claims description 3
• 239000005557 antagonist Substances 0.000 claims description 2
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
• 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 2
• 125000005842 heteroatom Chemical group 0.000 claims description 2
• 239000003199 leukotriene receptor blocking agent Substances 0.000 claims description 2
• 125000001624 naphthyl group Chemical group 0.000 claims description 2
• 230000002093 peripheral effect Effects 0.000 claims description 2
• 239000002089 prostaglandin antagonist Substances 0.000 claims description 2
• 239000002599 prostaglandin synthase inhibitor Substances 0.000 claims description 2
• 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 claims description 2
• 241000124008 Mammalia Species 0.000 claims 8
• 108090000110 Histamine H1 Receptors Proteins 0.000 claims 1
• 239000000739 antihistaminic agent Substances 0.000 claims 1
• 229940125715 antihistaminic agent Drugs 0.000 claims 1
• 235000019256 formaldehyde Nutrition 0.000 claims 1
• 229940077716 histamine h2 receptor antagonists for peptic ulcer and gord Drugs 0.000 claims 1
• 208000027866 inflammatory disease Diseases 0.000 claims 1
• 230000001120 cytoprotective effect Effects 0.000 abstract description 9
• 239000003795 chemical substances by application Substances 0.000 abstract description 7
• 239000000924 antiasthmatic agent Substances 0.000 abstract description 6
• 230000003266 anti-allergic effect Effects 0.000 abstract description 5
• 230000001088 anti-asthma Effects 0.000 abstract description 5
• 206010002383 Angina Pectoris Diseases 0.000 abstract description 3
• 208000037260 Atherosclerotic Plaque Diseases 0.000 abstract description 3
• 208000037487 Endotoxemia Diseases 0.000 abstract description 3
• 208000005392 Spasm Diseases 0.000 abstract description 3
• 206010046851 Uveitis 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
• 206010018364 Glomerulonephritis Diseases 0.000 abstract description 2
• 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 203
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 185
• 239000000203 mixture Substances 0.000 description 133
• 239000000243 solution Substances 0.000 description 125
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 114
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 101
• 235000019439 ethyl acetate Nutrition 0.000 description 101
• KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 93
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 91
• -1 heterocyclic ethers Chemical class 0.000 description 88
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 80
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 76
• 229910001868 water Inorganic materials 0.000 description 66
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 65
• 239000002904 solvent Substances 0.000 description 63
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
• 239000000047 product Substances 0.000 description 60
• 239000007787 solid Substances 0.000 description 55
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 54
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 50
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 43
• 238000006243 chemical reaction Methods 0.000 description 42
• 239000012267 brine Substances 0.000 description 41
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 41
• 235000019341 magnesium sulphate Nutrition 0.000 description 40
• 239000000741 silica gel Substances 0.000 description 39
• 229910002027 silica gel Inorganic materials 0.000 description 39
• 238000002360 preparation method Methods 0.000 description 37
• 239000003921 oil Substances 0.000 description 32
• 239000011541 reaction mixture Substances 0.000 description 32
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 29
• 239000012074 organic phase Substances 0.000 description 29
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 27
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
• 239000000543 intermediate Substances 0.000 description 25
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
• 150000002148 esters Chemical class 0.000 description 24
• 239000000725 suspension Substances 0.000 description 24
• QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 24
• 238000003818 flash chromatography Methods 0.000 description 23
• 239000002253 acid Substances 0.000 description 22
• 150000004820 halides Chemical class 0.000 description 22
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 20
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
• MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 19
• 239000012044 organic layer Substances 0.000 description 19
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 16
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 16
• 239000000443 aerosol Substances 0.000 description 15
• 229940079593 drug Drugs 0.000 description 15
• 239000003814 drug Substances 0.000 description 15
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 14
• 235000019270 ammonium chloride Nutrition 0.000 description 14
• 238000003556 assay Methods 0.000 description 14
• 239000012230 colorless oil Substances 0.000 description 13
• 239000012043 crude product Substances 0.000 description 13
• DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 13
• 241000700159 Rattus Species 0.000 description 12
• 239000000427 antigen Substances 0.000 description 12
• 102000036639 antigens Human genes 0.000 description 12
• 108091007433 antigens Proteins 0.000 description 12
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
• VNYSSYRCGWBHLG-AMOLWHMGSA-N leukotriene B4 Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O VNYSSYRCGWBHLG-AMOLWHMGSA-N 0.000 description 12
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
• WYUPDTVRGPHHOZ-UHFFFAOYSA-N 4-(furan-3-yl)-7-hydroxynaphthalene-2-carbonitrile Chemical compound C=1C(C#N)=CC2=CC(O)=CC=C2C=1C=1C=COC=1 WYUPDTVRGPHHOZ-UHFFFAOYSA-N 0.000 description 11
• UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 11
• 229910002091 carbon monoxide Inorganic materials 0.000 description 11
• 210000004027 cell Anatomy 0.000 description 11
• 238000001816 cooling Methods 0.000 description 11
• 230000000694 effects Effects 0.000 description 11
• 238000001704 evaporation Methods 0.000 description 11
• 230000008020 evaporation Effects 0.000 description 11
• 238000011534 incubation Methods 0.000 description 11
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 11
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 11
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
• 241000894007 species Species 0.000 description 11
• 238000012360 testing method Methods 0.000 description 11
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 11
• 238000005481 NMR spectroscopy Methods 0.000 description 10
• 239000000706 filtrate Substances 0.000 description 10
• 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 10
• 239000007788 liquid Substances 0.000 description 10
• 239000003960 organic solvent Substances 0.000 description 10
• JMJRYTGVHCAYCT-UHFFFAOYSA-N oxan-4-one Chemical compound O=C1CCOCC1 JMJRYTGVHCAYCT-UHFFFAOYSA-N 0.000 description 10
• 150000005599 propionic acid derivatives Chemical class 0.000 description 10
• 235000017557 sodium bicarbonate Nutrition 0.000 description 10
• 238000003756 stirring Methods 0.000 description 10
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 10
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
• 241000282414 Homo sapiens Species 0.000 description 9
• 239000000872 buffer Substances 0.000 description 9
• 150000007529 inorganic bases Chemical class 0.000 description 9
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
• 238000003127 radioimmunoassay Methods 0.000 description 9
• 239000003826 tablet Substances 0.000 description 9
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 9
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
• 241001494479 Pecora Species 0.000 description 8
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 8
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 8
• 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 description 8
• 239000002585 base Substances 0.000 description 8
• 239000000463 material Substances 0.000 description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 8
• 239000000843 powder Substances 0.000 description 8
• 230000004044 response Effects 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
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
• 150000001242 acetic acid derivatives Chemical class 0.000 description 7
• 150000007513 acids Chemical class 0.000 description 7
• 239000002775 capsule Substances 0.000 description 7
• 125000004122 cyclic group Chemical group 0.000 description 7
• ZWJINEZUASEZBH-UHFFFAOYSA-N fenamic acid Chemical class OC(=O)C1=CC=CC=C1NC1=CC=CC=C1 ZWJINEZUASEZBH-UHFFFAOYSA-N 0.000 description 7
• 238000010438 heat treatment Methods 0.000 description 7
• 229910052744 lithium Inorganic materials 0.000 description 7
• 150000007530 organic bases Chemical class 0.000 description 7
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 7
• 230000000241 respiratory effect Effects 0.000 description 7
• 230000003637 steroidlike Effects 0.000 description 7
• 239000006228 supernatant Substances 0.000 description 7
• WJIFKOVZNJTSGO-UHFFFAOYSA-N 1-bromo-3-methylbenzene Chemical compound CC1=CC=CC(Br)=C1 WJIFKOVZNJTSGO-UHFFFAOYSA-N 0.000 description 6
• 239000007832 Na2SO4 Substances 0.000 description 6
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
• 230000037396 body weight Effects 0.000 description 6
• 201000010099 disease Diseases 0.000 description 6
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
• 239000000284 extract Substances 0.000 description 6
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 6
• 150000002576 ketones Chemical class 0.000 description 6
• 150000002596 lactones Chemical class 0.000 description 6
• 239000010410 layer Substances 0.000 description 6
• 238000005259 measurement Methods 0.000 description 6
• YVUXLHOKNGBRDU-UHFFFAOYSA-N methyl 7-hydroxy-4-phenylnaphthalene-2-carboxylate Chemical compound C=12C=CC(O)=CC2=CC(C(=O)OC)=CC=1C1=CC=CC=C1 YVUXLHOKNGBRDU-UHFFFAOYSA-N 0.000 description 6
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
• 229910000027 potassium carbonate Inorganic materials 0.000 description 6
• 230000002685 pulmonary effect Effects 0.000 description 6
• 238000000746 purification Methods 0.000 description 6
• AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 6
• SHNUBALDGXWUJI-UHFFFAOYSA-N pyridin-2-ylmethanol Chemical compound OCC1=CC=CC=N1 SHNUBALDGXWUJI-UHFFFAOYSA-N 0.000 description 6
• 238000010992 reflux Methods 0.000 description 6
• 229910052938 sodium sulfate Inorganic materials 0.000 description 6
• 235000011152 sodium sulphate Nutrition 0.000 description 6
• WBYXNUMKRHPAGH-UHFFFAOYSA-N 7-hydroxy-4-phenylnaphthalene-2-carboxylic acid Chemical compound C=12C=CC(O)=CC2=CC(C(=O)O)=CC=1C1=CC=CC=C1 WBYXNUMKRHPAGH-UHFFFAOYSA-N 0.000 description 5
• 241000244188 Ascaris suum Species 0.000 description 5
• 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 5
• 101000620009 Homo sapiens Polyunsaturated fatty acid 5-lipoxygenase Proteins 0.000 description 5
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 5
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 5
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
• 150000001412 amines Chemical class 0.000 description 5
• 230000000202 analgesic effect Effects 0.000 description 5
• 239000008346 aqueous phase Substances 0.000 description 5
• AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
• 244000309464 bull Species 0.000 description 5
• 230000008859 change Effects 0.000 description 5
• 239000002552 dosage form Substances 0.000 description 5
• 229960000905 indomethacin Drugs 0.000 description 5
• 239000004615 ingredient Substances 0.000 description 5
• 239000002207 metabolite Substances 0.000 description 5
• 235000015320 potassium carbonate Nutrition 0.000 description 5
• 238000011084 recovery Methods 0.000 description 5
• 125000001424 substituent group Chemical group 0.000 description 5
• 235000020357 syrup Nutrition 0.000 description 5
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