CS241109B2 - Method of 5-hydroxy-6-substituted thio-6-substituted hexane acids production - Google Patents
Method of 5-hydroxy-6-substituted thio-6-substituted hexane acids production Download PDFInfo
- Publication number
- CS241109B2 CS241109B2 CS824565A CS456582A CS241109B2 CS 241109 B2 CS241109 B2 CS 241109B2 CS 824565 A CS824565 A CS 824565A CS 456582 A CS456582 A CS 456582A CS 241109 B2 CS241109 B2 CS 241109B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- hydroxy
- acid
- solution
- substituted
- group
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 title description 34
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 72
- 239000002253 acid Substances 0.000 claims abstract description 51
- 125000001424 substituent group Chemical group 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical group NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid group Chemical class C(CCCCC)(=O)O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000004471 Glycine Substances 0.000 claims description 3
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical group C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 2
- 235000004279 alanine Nutrition 0.000 claims description 2
- 229910001413 alkali metal ion Inorganic materials 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
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims description 2
- 150000003462 sulfoxides Chemical class 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- -1 and X is OH Chemical group 0.000 abstract description 26
- 229910052736 halogen Inorganic materials 0.000 abstract description 6
- 150000002367 halogens Chemical class 0.000 abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 5
- 208000010668 atopic eczema Diseases 0.000 abstract description 4
- 230000000172 allergic effect Effects 0.000 abstract description 3
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 abstract description 2
- 125000003118 aryl group Chemical group 0.000 abstract 6
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 4
- 125000001072 heteroaryl group Chemical group 0.000 abstract 4
- 125000000304 alkynyl group Chemical group 0.000 abstract 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
- 125000000539 amino acid group Chemical group 0.000 abstract 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 230000001364 causal effect Effects 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 208000027866 inflammatory disease Diseases 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 125000004953 trihalomethyl group Chemical group 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 93
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 83
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- 239000000203 mixture Substances 0.000 description 50
- 239000003921 oil Substances 0.000 description 38
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 150000004702 methyl esters Chemical class 0.000 description 18
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- 239000000284 extract Substances 0.000 description 16
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 150000002118 epoxides Chemical class 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- 150000003573 thiols Chemical class 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 8
- 150000002596 lactones Chemical class 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- 159000000000 sodium salts Chemical class 0.000 description 8
- 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 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 239000012259 ether extract Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 208000006673 asthma Diseases 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000010902 straw Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- INKQLYSQWHBEGS-UHFFFAOYSA-N (Z)-nonadec-2-enoic acid Chemical compound C(C=C/CCCCCCCCCCCCCCCC)(=O)O INKQLYSQWHBEGS-UHFFFAOYSA-N 0.000 description 3
- PHHNNTANZBVDCX-QHHAFSJGSA-N (e)-6-naphthalen-2-ylhex-5-enoic acid Chemical compound C1=CC=CC2=CC(/C=C/CCCC(=O)O)=CC=C21 PHHNNTANZBVDCX-QHHAFSJGSA-N 0.000 description 3
- IRWGNRPDRSDNPL-UPHRSURJSA-N (z)-8-phenyloct-5-enoic acid Chemical compound OC(=O)CCC\C=C/CCC1=CC=CC=C1 IRWGNRPDRSDNPL-UPHRSURJSA-N 0.000 description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- AYVPTAOSEQFSHG-HNENSFHCSA-N COC(\C=C/CCCCCCCCCCCCCCCC)=O Chemical compound COC(\C=C/CCCCCCCCCCCCCCCC)=O AYVPTAOSEQFSHG-HNENSFHCSA-N 0.000 description 3
- 206010020751 Hypersensitivity Diseases 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000012258 stirred mixture Substances 0.000 description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- IQLUYYHUNSSHIY-GKYQVSAZSA-N (2z)-icosa-2,4,6,8-tetraenoic acid Chemical compound CCCCCCCCCCCC=CC=CC=C\C=C/C(O)=O IQLUYYHUNSSHIY-GKYQVSAZSA-N 0.000 description 2
- 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 2
- YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical compound O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 description 2
- MLOSJPZSZWUDSK-UHFFFAOYSA-N 4-carboxybutyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCC(=O)O)C1=CC=CC=C1 MLOSJPZSZWUDSK-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 206010006482 Bronchospasm Diseases 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- 208000019693 Lung disease Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
- WTRNXHQNTGJCBK-UHFFFAOYSA-N dimethyl 2-sulfanylbutanedioate Chemical compound COC(=O)CC(S)C(=O)OC WTRNXHQNTGJCBK-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- NSIFOGPAKNSGNW-UHFFFAOYSA-M dodecyl(triphenyl)phosphonium bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCCCCCCCCC)C1=CC=CC=C1 NSIFOGPAKNSGNW-UHFFFAOYSA-M 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000000543 intermediate Substances 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
- AGGAPCMHKPZNTJ-BUHFOSPRSA-N methyl (E)-2-hydroxynonadec-7-enoate Chemical compound CCCCCCCCCCC/C=C/CCCCC(C(=O)OC)O AGGAPCMHKPZNTJ-BUHFOSPRSA-N 0.000 description 2
- MSCOCENDJFTIPB-SNAWJCMRSA-N methyl (E)-2-hydroxyoct-5-enoate Chemical compound CC\C=C\CCC(O)C(=O)OC MSCOCENDJFTIPB-SNAWJCMRSA-N 0.000 description 2
- VSGUVLFDQAFAFJ-XVNBXDOJSA-N methyl (e)-6-naphthalen-2-ylhex-5-enoate Chemical compound C1=CC=CC2=CC(/C=C/CCCC(=O)OC)=CC=C21 VSGUVLFDQAFAFJ-XVNBXDOJSA-N 0.000 description 2
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 2
- MOZVYFLGFQZCRR-UHFFFAOYSA-N methyl 7-oxooct-5-enoate Chemical compound COC(=O)CCCC=CC(C)=O MOZVYFLGFQZCRR-UHFFFAOYSA-N 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 210000002345 respiratory system Anatomy 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- XJRIDJAGAYGJCK-UHFFFAOYSA-N (1-acetyl-5-bromoindol-3-yl) acetate Chemical compound C1=C(Br)C=C2C(OC(=O)C)=CN(C(C)=O)C2=C1 XJRIDJAGAYGJCK-UHFFFAOYSA-N 0.000 description 1
- PZSXRVFFCOEADI-VKHMYHEASA-N (2R)-2-[methyl-(2,2,2-trifluoroacetyl)amino]-3-sulfanylpropanoic acid Chemical compound SC[C@@H](C(O)=O)N(C)C(=O)C(F)(F)F PZSXRVFFCOEADI-VKHMYHEASA-N 0.000 description 1
- LTJLUCQHTRQZFA-REOHCLBHSA-N (2r)-3-sulfanyl-2-[(2,2,2-trifluoroacetyl)amino]propanoic acid Chemical compound OC(=O)[C@H](CS)NC(=O)C(F)(F)F LTJLUCQHTRQZFA-REOHCLBHSA-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
- LAQPKDLYOBZWBT-NYLDSJSYSA-N (2s,4s,5r,6r)-5-acetamido-2-{[(2s,3r,4s,5s,6r)-2-{[(2r,3r,4r,5r)-5-acetamido-1,2-dihydroxy-6-oxo-4-{[(2s,3s,4r,5s,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-6-[(1r,2r)-1,2,3-trihydrox Chemical compound O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@H]([C@@H](NC(C)=O)C=O)[C@@H]([C@H](O)CO)O[C@H]1[C@H](O)[C@@H](O[C@]2(O[C@H]([C@H](NC(C)=O)[C@@H](O)C2)[C@H](O)[C@H](O)CO)C(O)=O)[C@@H](O)[C@@H](CO)O1 LAQPKDLYOBZWBT-NYLDSJSYSA-N 0.000 description 1
- PXUFLONILGQOFT-FARCUNLSSA-N (e)-6-naphthalen-1-ylhex-5-enoic acid Chemical class C1=CC=C2C(/C=C/CCCC(=O)O)=CC=CC2=C1 PXUFLONILGQOFT-FARCUNLSSA-N 0.000 description 1
- PHHNNTANZBVDCX-KXFIGUGUSA-N (z)-6-naphthalen-2-ylhex-5-enoic acid Chemical compound C1=CC=CC2=CC(\C=C/CCCC(=O)O)=CC=C21 PHHNNTANZBVDCX-KXFIGUGUSA-N 0.000 description 1
- KAANTNXREIRLCT-UHFFFAOYSA-N 1-(triphenyl-$l^{5}-phosphanylidene)propan-2-one Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)C)C1=CC=CC=C1 KAANTNXREIRLCT-UHFFFAOYSA-N 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- 238000004565 12C NMR spectroscopy Methods 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- ZFFTZDQKIXPDAF-UHFFFAOYSA-N 2-Furanmethanethiol Chemical compound SCC1=CC=CO1 ZFFTZDQKIXPDAF-UHFFFAOYSA-N 0.000 description 1
- VQKFNUFAXTZWDK-UHFFFAOYSA-N 2-Methylfuran Chemical compound CC1=CC=CO1 VQKFNUFAXTZWDK-UHFFFAOYSA-N 0.000 description 1
- PJKVFARRVXDXAD-UHFFFAOYSA-N 2-naphthaldehyde Chemical compound C1=CC=CC2=CC(C=O)=CC=C21 PJKVFARRVXDXAD-UHFFFAOYSA-N 0.000 description 1
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 1
- CKOZVEHVVHCMGD-UHFFFAOYSA-N 5-[(4-fluorophenyl)methyl]-n,n-dimethyltetrazole-1-carboxamide Chemical compound CN(C)C(=O)N1N=NN=C1CC1=CC=C(F)C=C1 CKOZVEHVVHCMGD-UHFFFAOYSA-N 0.000 description 1
- HPDPNQKWAHKIKF-UHFFFAOYSA-N 6-ethylsulfanyl-5-hydroxy-8-phenyloctanoic acid Chemical compound OC(=O)CCCC(O)C(SCC)CCC1=CC=CC=C1 HPDPNQKWAHKIKF-UHFFFAOYSA-N 0.000 description 1
- 241000220479 Acacia Species 0.000 description 1
- 241000238876 Acari Species 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
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 208000028185 Angioedema Diseases 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 208000009079 Bronchial Spasm Diseases 0.000 description 1
- 208000014181 Bronchial disease Diseases 0.000 description 1
- JQNKKMGOBCHUHJ-UHFFFAOYSA-N C(C)N(CC)CC.C1(O)=CC=C(O)C=C1 Chemical compound C(C)N(CC)CC.C1(O)=CC=C(O)C=C1 JQNKKMGOBCHUHJ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- 241000272201 Columbiformes Species 0.000 description 1
- 201000003883 Cystic fibrosis Diseases 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-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
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 206010012438 Dermatitis atopic Diseases 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 241000755093 Gaidropsarus vulgaris Species 0.000 description 1
- 108010010803 Gelatin Proteins 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
- 206010061218 Inflammation Diseases 0.000 description 1
- 239000004201 L-cysteine Substances 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
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- UUIQMZJEGPQKFD-UHFFFAOYSA-N Methyl butyrate Chemical compound CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- 208000025047 Non-histaminic angioedema Diseases 0.000 description 1
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 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 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 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
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- BNQRPLGZFADFGA-UHFFFAOYSA-N benzyl(triphenyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 BNQRPLGZFADFGA-UHFFFAOYSA-N 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
- 239000011230 binding agent Substances 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- WPWNIQBSYQVEKJ-UHFFFAOYSA-M chembl2028451 Chemical compound [Na+].CC1=CC(S([O-])(=O)=O)=CC=C1N=NC1=C(O)C=CC2=CC=CC=C12 WPWNIQBSYQVEKJ-UHFFFAOYSA-M 0.000 description 1
- 208000010247 contact dermatitis Diseases 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- GVPLMQGXUUHCSB-UHFFFAOYSA-M decyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCCCCCCC)C1=CC=CC=C1 GVPLMQGXUUHCSB-UHFFFAOYSA-M 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 229960005215 dichloroacetic acid Drugs 0.000 description 1
- 239000002027 dichloromethane extract Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000010696 ester oil Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- COQRGFWWJBEXRC-UHFFFAOYSA-N hydron;methyl 2-aminoacetate;chloride Chemical compound Cl.COC(=O)CN COQRGFWWJBEXRC-UHFFFAOYSA-N 0.000 description 1
- 210000003405 ileum Anatomy 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229960000310 isoleucine Drugs 0.000 description 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000007273 lactonization reaction Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 230000004199 lung function Effects 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 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
- 229960000582 mepyramine Drugs 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- VWGSQMAKRLENER-VKHMYHEASA-N methyl (2r)-3-sulfanyl-2-[(2,2,2-trifluoroacetyl)amino]propanoate Chemical compound COC(=O)[C@H](CS)NC(=O)C(F)(F)F VWGSQMAKRLENER-VKHMYHEASA-N 0.000 description 1
- LHTQTTPCVGQXLI-JLHYYAGUSA-N methyl (e)-6-(4-octylphenyl)hex-5-enoate Chemical compound CCCCCCCCC1=CC=C(\C=C\CCCC(=O)OC)C=C1 LHTQTTPCVGQXLI-JLHYYAGUSA-N 0.000 description 1
- NGCZXEZDGTUCMN-XBXARRHUSA-N methyl (e)-6-(4-phenylphenyl)hex-5-enoate Chemical compound C1=CC(/C=C/CCCC(=O)OC)=CC=C1C1=CC=CC=C1 NGCZXEZDGTUCMN-XBXARRHUSA-N 0.000 description 1
- WAPHZSQXQXYBJJ-GQCTYLIASA-N methyl (e)-6-(6-methylnaphthalen-2-yl)hex-5-enoate Chemical compound C1=C(C)C=CC2=CC(/C=C/CCCC(=O)OC)=CC=C21 WAPHZSQXQXYBJJ-GQCTYLIASA-N 0.000 description 1
- HVCAEGKPSFLHGR-FPYGCLRLSA-N methyl (e)-6-naphthalen-1-ylhex-5-enoate Chemical compound C1=CC=C2C(/C=C/CCCC(=O)OC)=CC=CC2=C1 HVCAEGKPSFLHGR-FPYGCLRLSA-N 0.000 description 1
- MBIDEUCNOFLFPC-IHWYPQMZSA-N methyl (z)-8-phenyloct-5-enoate Chemical compound COC(=O)CCC\C=C/CCC1=CC=CC=C1 MBIDEUCNOFLFPC-IHWYPQMZSA-N 0.000 description 1
- MBMVGTHOCLYAOI-UHFFFAOYSA-N methyl 5-ethylsulfanyl-6-hydroxy-8-phenyloctanoate Chemical compound COC(=O)CCCC(SCC)C(O)CCC1=CC=CC=C1 MBMVGTHOCLYAOI-UHFFFAOYSA-N 0.000 description 1
- VVYNOPVDUMQBNU-UHFFFAOYSA-N methyl 6-ethylsulfanyl-5-hydroxy-8-phenyloctanoate Chemical compound COC(=O)CCCC(O)C(SCC)CCC1=CC=CC=C1 VVYNOPVDUMQBNU-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
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- PHWISQNXPLXQRU-UHFFFAOYSA-N n,n-dimethylcarbamothioyl chloride Chemical compound CN(C)C(Cl)=S PHWISQNXPLXQRU-UHFFFAOYSA-N 0.000 description 1
- GTQBDKSAYITDPT-UHFFFAOYSA-N n-(2-ethyl-2-methyl-4-oxothietan-3-yl)acetamide Chemical compound CCC1(C)SC(=O)C1NC(C)=O GTQBDKSAYITDPT-UHFFFAOYSA-N 0.000 description 1
- MOYSMPXSEXYEJV-UHFFFAOYSA-M naphthalen-1-ylmethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC2=CC=CC=C2C=1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 MOYSMPXSEXYEJV-UHFFFAOYSA-M 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- LZFIOSVZIQOVFW-UHFFFAOYSA-N propyl 2-hydroxybenzoate Chemical compound CCCOC(=O)C1=CC=CC=C1O LZFIOSVZIQOVFW-UHFFFAOYSA-N 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 235000011182 sodium carbonates Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000008275 solid aerosol Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000012058 sterile packaged powder Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 125000005270 trialkylamine 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
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- JFQMKACNTNIVEM-UHFFFAOYSA-N undec-5-enoic acid Chemical compound CCCCCC=CCCCC(O)=O JFQMKACNTNIVEM-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B45/00—Formation or introduction of functional groups containing sulfur
- C07B45/04—Formation or introduction of functional groups containing sulfur of sulfonyl or sulfinyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- C07C317/46—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/56—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
- C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D303/40—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by ester radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D303/40—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by ester radicals
- C07D303/42—Acyclic compounds having a chain of seven or more carbon atoms, e.g. epoxidised fats
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/30—Oxygen atoms, e.g. delta-lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
- C07D313/02—Seven-membered rings
- C07D313/04—Seven-membered rings not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/5304—Acyclic saturated phosphine oxides or thioxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/5325—Aromatic phosphine oxides or thioxides (P-C aromatic linkage)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB8118720 | 1981-06-18 | ||
GB8213211 | 1982-05-07 |
Publications (2)
Publication Number | Publication Date |
---|---|
CS456582A2 CS456582A2 (en) | 1985-07-16 |
CS241109B2 true CS241109B2 (en) | 1986-03-13 |
Family
ID=26279835
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CS824565A CS241109B2 (en) | 1981-06-18 | 1982-06-18 | Method of 5-hydroxy-6-substituted thio-6-substituted hexane acids production |
Country Status (23)
Country | Link |
---|---|
US (1) | US4513005A (xx) |
EP (1) | EP0068739B1 (xx) |
KR (1) | KR890000622B1 (xx) |
AU (1) | AU549814B2 (xx) |
BG (1) | BG37226A3 (xx) |
CA (1) | CA1224795A (xx) |
CS (1) | CS241109B2 (xx) |
DD (1) | DD202697A5 (xx) |
DE (1) | DE3261237D1 (xx) |
DK (1) | DK271682A (xx) |
ES (3) | ES513221A0 (xx) |
FI (1) | FI77847C (xx) |
GB (1) | GB2101594B (xx) |
GR (1) | GR76838B (xx) |
HU (1) | HU192105B (xx) |
IE (1) | IE53522B1 (xx) |
IL (1) | IL66056A0 (xx) |
NZ (1) | NZ200984A (xx) |
PH (1) | PH23051A (xx) |
PL (4) | PL137766B1 (xx) |
PT (1) | PT75058B (xx) |
RO (1) | RO83706B (xx) |
ZA (1) | ZA824294B (xx) |
Families Citing this family (50)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2480747A1 (fr) * | 1980-04-17 | 1981-10-23 | Roques Bernard | Derives d'acides amines et leur application therapeutique |
US4537723A (en) * | 1982-02-04 | 1985-08-27 | The Upjohn Company | Derivatives of leukotrienes A and C |
DK130984A (da) * | 1983-03-07 | 1984-09-08 | Smithkline Beckman Corp | Leukotrien-antagonister |
US4775662A (en) * | 1983-03-07 | 1988-10-04 | Smithkline Beckman Corporation | Leukotriene antagonists |
US4609744A (en) * | 1983-04-21 | 1986-09-02 | Merck Frosst Canada Inc. | 4-oxo-benzopyran carboxylic acids |
US5017583A (en) * | 1983-04-21 | 1991-05-21 | Merck Frosst Canada, Inc. | Leukotriene antagonists |
EP0123543B1 (en) * | 1983-04-21 | 1988-02-03 | Merck Frosst Canada Inc. | Leukotriene antagonists, their production and use and compositions containing them |
US4720505A (en) * | 1983-06-27 | 1988-01-19 | Merck Frosst Canada, Inc. | Leukotriene antagonists |
GB8320943D0 (en) * | 1983-08-03 | 1983-09-07 | Lilly Industries Ltd | Organic compounds |
US4761425A (en) * | 1983-12-27 | 1988-08-02 | Merck Frosst Canada, Inc. | Leukotriene antagonists |
AU572615B2 (en) | 1983-12-27 | 1988-05-12 | Sony Corporation | Electrically conductive adhesive sheet circuit board and electrical connection structure |
EP0147217A3 (en) * | 1983-12-27 | 1986-08-13 | Merck Frosst Canada Inc. | Leukotriene antagonists |
US4769386A (en) * | 1984-06-18 | 1988-09-06 | Smithkline Beckman Corporation | Imidazolylthioalkenoic acids and -alkenols and leukotriene antagonistic composition containing them |
IL75620A (en) * | 1984-06-28 | 1989-05-15 | Ciba Geigy | Aliphatic thioethers of alkanoic acid derivatives,their manufacture and pharmaceutical compositions containing them |
US4889873A (en) * | 1984-07-18 | 1989-12-26 | Schering Corporation | Inhibitors of slow reacting substance of anaphylaxis |
US4758594A (en) * | 1984-07-18 | 1988-07-19 | Schering Corporation | Inhibitors of slow reacting substance of anaphylaxis |
US4988716A (en) * | 1984-07-18 | 1991-01-29 | Schering Corporation | Inhibitors of slow reacting substance of anaphylaxis |
US4798842A (en) * | 1984-07-18 | 1989-01-17 | Schering Corporation | Inhibitors of slow reacting substance of anaphylaxis |
GB8502258D0 (en) * | 1985-01-30 | 1985-02-27 | Lilly Industries Ltd | Organic compounds |
US4939279A (en) * | 1985-04-19 | 1990-07-03 | Smithkline Beecham Corporation | Leukotriene antagonists |
DE3672130D1 (de) * | 1985-04-19 | 1990-07-26 | Smithkline Beecham Corp | Leukotrien-antagonisten. |
US4874792A (en) * | 1985-04-19 | 1989-10-17 | Smithkline Beckman Corporation | Thiophenyl Alkanoic acids useful as leukotriene antagonists |
US4937253A (en) * | 1985-04-19 | 1990-06-26 | Smithkline Beecham Corporation | Ester prodrugs |
CA1309557C (en) | 1985-06-18 | 1992-10-27 | Robert N. Young | Leukotriene antagonists |
US4990526A (en) * | 1985-06-18 | 1991-02-05 | Merck Frosst Canada, Inc. | Leukotriene antagonists, compositions and methods of use thereof |
US4696946A (en) * | 1985-08-30 | 1987-09-29 | Schering Corporation | Topical Treatment of hyperproliferative skin diseases |
US4783483A (en) * | 1985-10-03 | 1988-11-08 | Ortho Pharmaceutical Corporation | Epoxides useful as antiallergic agents |
FI864901A (fi) * | 1985-12-06 | 1987-06-07 | Ciba Geigy Ag | Hydroxitioetrar. |
KR870011086A (ko) * | 1986-05-29 | 1987-12-19 | 벤자민 에프. 램버트 | 포스포리파제 a₂억제제 및 그의 합성방법 |
GB8709547D0 (en) * | 1987-04-22 | 1987-05-28 | Lilly Industries Ltd | Organic compounds |
DE3724669A1 (de) * | 1987-07-25 | 1989-02-02 | Hoechst Ag | Leukotrienantagonisten, verfahren zu ihrer herstellung und ihre anwendung zur behandlung von krankheiten |
DE3724735A1 (de) * | 1987-07-25 | 1989-02-02 | Hoechst Ag | Leukotrienantagonisten, verfahren zu ihrer herstellung, ihre anwendung zur behandlung von krankheiten, sowie vorprodukte |
GB8725260D0 (en) * | 1987-10-28 | 1987-12-02 | Lilly Industries Ltd | Organic compounds |
AU610528B2 (en) * | 1987-10-29 | 1991-05-23 | Smithkline Beckman Corporation | Leukotriene antagonists |
GB8807016D0 (en) * | 1988-03-24 | 1988-04-27 | Lilly Industries Ltd | Organic compounds & their pharmaceutical use |
US5073571A (en) * | 1988-06-16 | 1991-12-17 | Washington University | Method of inhibiting virus |
US4954513A (en) * | 1988-12-23 | 1990-09-04 | Smithkline Beecham Corporation | Leukotriene antagonists |
US5149835A (en) * | 1989-04-27 | 1992-09-22 | University Of New Mexico | Substituted mevalonolactones, and methods for stereoselective preparation thereof and desmethyl homologues thereof |
EP0410244A1 (en) * | 1989-07-27 | 1991-01-30 | Bayer Ag | Leukotriene antagonists |
US5238683A (en) * | 1989-11-24 | 1993-08-24 | The United States Of America As Represented By The Department Of Health And Human Services | Aerosol preparation of glutathione and a method for augmenting glutathione level in lungs |
CA2081480A1 (en) * | 1990-05-01 | 1991-11-02 | James S. Frazee | 3-naphthyl-3-carboxyalkylthio or oxy substituted alkanoic acid leukotriene antagonists |
US7842727B2 (en) * | 2001-03-27 | 2010-11-30 | Errant Gene Therapeutics, Llc | Histone deacetylase inhibitors |
US8026280B2 (en) * | 2001-03-27 | 2011-09-27 | Errant Gene Therapeutics, Llc | Histone deacetylase inhibitors |
US7312247B2 (en) * | 2001-03-27 | 2007-12-25 | Errant Gene Therapeutics, Llc | Histone deacetylase inhibitors |
US20030212191A1 (en) * | 2002-04-15 | 2003-11-13 | Nippon Bee Chemical Co., Ltd. | Aqueous primer coating composition, process for formation of coating film using said composition, and coated article |
AU2003243272A1 (en) * | 2002-05-22 | 2003-12-12 | Errant Gene Therapeutics, Llc | Histone deacetylase inhibitors based on alpha-ketoepoxide compounds |
JP2006508986A (ja) * | 2002-11-20 | 2006-03-16 | エルラント ゲネ セラペウチクス エルエルシー | ヒストンデアセチラーゼ阻害剤による肺細胞の治療方法 |
WO2006025155A1 (ja) * | 2004-08-31 | 2006-03-09 | Sumitomo Bakelite Co., Ltd. | オキシルアミノ基含有化合物およびポリマー |
WO2006052916A2 (en) * | 2004-11-08 | 2006-05-18 | Errant Gene Therapeutics, Inc. | Histone deacetylase inhibitors |
US7754838B2 (en) * | 2006-08-08 | 2010-07-13 | E.I. Du Pont De Nemours And Company | Poly(meth)acrylamides and poly(meth)acrylates containing fluorinated amide |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3177227A (en) * | 1963-01-30 | 1965-04-06 | Shell Oil Co | Lactone production |
DE2945497A1 (de) * | 1979-03-06 | 1980-10-09 | Degussa | Derivate der d-2-hydroxy-4-methylmercaptobuttersaeure, verfahren zu deren herstellung und deren verwendung |
US4311645A (en) * | 1980-03-24 | 1982-01-19 | Hoffmann-La Roche Inc. | Synthesis of SRS-active compounds |
FR2479213A1 (fr) * | 1980-03-28 | 1981-10-02 | Roussel Uclaf | Procede de preparation d'acide pentenoique possedant une fonction aldehyde |
JPS57118555A (en) * | 1981-01-13 | 1982-07-23 | Ono Pharmaceut Co Ltd | Leucotriene-analog compound, its preparation, and leucotriene-biosynthesis inhibiting agent containing said compound as active component |
US4352757A (en) * | 1981-02-02 | 1982-10-05 | Smithkline Beckman Corporation | Process for the preparation of esters of leukotriene A |
-
1982
- 1982-06-09 US US06/386,570 patent/US4513005A/en not_active Expired - Fee Related
- 1982-06-14 IL IL66056A patent/IL66056A0/xx not_active IP Right Cessation
- 1982-06-16 PT PT75058A patent/PT75058B/pt not_active IP Right Cessation
- 1982-06-16 PH PH27436A patent/PH23051A/en unknown
- 1982-06-16 HU HU821941A patent/HU192105B/hu not_active IP Right Cessation
- 1982-06-16 DK DK271682A patent/DK271682A/da not_active Application Discontinuation
- 1982-06-16 NZ NZ200984A patent/NZ200984A/en unknown
- 1982-06-17 CA CA000405382A patent/CA1224795A/en not_active Expired
- 1982-06-17 GB GB08217589A patent/GB2101594B/en not_active Expired
- 1982-06-17 BG BG057037A patent/BG37226A3/xx unknown
- 1982-06-17 ES ES513221A patent/ES513221A0/es active Granted
- 1982-06-17 RO RO107910A patent/RO83706B/ro unknown
- 1982-06-17 DE DE8282303154T patent/DE3261237D1/de not_active Expired
- 1982-06-17 DD DD82240838A patent/DD202697A5/de not_active IP Right Cessation
- 1982-06-17 ZA ZA824294A patent/ZA824294B/xx unknown
- 1982-06-17 IE IE1443/82A patent/IE53522B1/en not_active IP Right Cessation
- 1982-06-17 EP EP82303154A patent/EP0068739B1/en not_active Expired
- 1982-06-18 FI FI822205A patent/FI77847C/fi not_active IP Right Cessation
- 1982-06-18 GR GR68479A patent/GR76838B/el unknown
- 1982-06-18 AU AU85008/82A patent/AU549814B2/en not_active Ceased
- 1982-06-18 CS CS824565A patent/CS241109B2/cs unknown
- 1982-06-18 PL PL1982240482A patent/PL137766B1/pl unknown
- 1982-06-18 PL PL24048382A patent/PL240483A1/xx unknown
- 1982-06-18 PL PL24048482A patent/PL240484A1/xx unknown
- 1982-06-18 KR KR828202722A patent/KR890000622B1/ko active
- 1982-06-18 PL PL23699282A patent/PL236992A1/xx unknown
-
1983
- 1983-03-16 ES ES520670A patent/ES520670A0/es active Granted
- 1983-03-16 ES ES520671A patent/ES520671A0/es active Granted
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CS241109B2 (en) | Method of 5-hydroxy-6-substituted thio-6-substituted hexane acids production | |
EP0201823B1 (en) | Novel intermediates for the production of pharmaceuticals | |
EP0147177B1 (en) | Ether prodrugs of anti-inflammatory oxicams | |
US4122194A (en) | Aryl sulphur compounds as antiasthmatics | |
CZ280564B6 (cs) | Z-2-Acylamino-3-monosubstituované propenoáty, způsoby jejich výroby a antibakteriální přípravky s jejich obsahem | |
KR100377448B1 (ko) | 카바페넴 항생물질의 중간체 및 그의 제조방법 | |
US4588742A (en) | Thiabicycloheptane substituted prostaglandin analogs useful in the treatment of thrombotic disease | |
ES2449494T3 (es) | Procedimiento para la producción de ácido 9-cis-retinoico | |
GB2094301A (en) | Improvements in or relating to organic compounds | |
US4886885A (en) | Compound containing tetrazolyl groups and their use for treating allergies and cardiovascular disease | |
EP0127848A2 (en) | 5-Thiaalkanoic acid derivatives having antihypercholesterolemic activity | |
EP0298583B1 (en) | Aromatic thioethers | |
JPS6067458A (ja) | N−アセチルシステイン及びs−カルボキシメチルシステインの2′,4′−ジフルオロ−4−ヒドロキシ−(1,1′−ジフエニル)−3−カルボキシル誘導体、及びそれを含む組成物 | |
RU2058979C1 (ru) | Производные алкенкарбоновой кислоты, или смеси их изомеров, или их индивидуальные изомеры, или соли, обладающие свойствами антагонистов лейкотриена, способы их получения, промежуточные для их получения, и фармацевтическая композиция на их основе | |
SK58893A3 (en) | Phosphinyloxy propanaminium inner salt derivatives | |
EP0063858B1 (en) | Leukotriene analogues, their preparation and use in pharmaceutical compositions | |
US4425358A (en) | 13-Thia-prostacycline derivatives | |
US4837343A (en) | Optically active β-amino acid derivatives and their salts, and processes for producing the same | |
SK5093A3 (en) | Process and intermediate for the preparation of 2-hydroxy-3-sulfido-3-phenyl propanoic acids | |
HU180103B (en) | Process for producing analogues of 9,11,15-trideoxy-prostaglandine-f | |
IL37224A (en) | Pharmaceutical preparations containing 3 - acyloxypropyl - 2 - trimethyl ammonium (noble phosphates | |
KR820000509B1 (ko) | △2,4-11-데옥시-pge계프로스타글란딘 유도체의 제조방법 | |
KR900000738B1 (ko) | [3s(z)]-2-[[[1-(2-아미노-4-티아졸릴)-2-[[2,2-디메틸-4-옥소-1-(술포옥시)-3-아제티디닐]아미노]-2-옥소에틸리덴]아미노]옥시]아세트산 화합물 및 약물학적으로 허용되는 그의 염류, 및 그의 제조 방법 | |
EP0090603A2 (en) | Antibacterial compounds | |
IE53523B1 (en) | Oxiranyl butyric acid derivatives |