PH26257A - Novel 6-phenoxymethyl-4- hydroxytetrahydropyran-2-ones and 6-thiophenoxymethyl-4-hydroxytetrahydropyran-2- ones and the corresponding dihydroxycarboxylic acid derivatives salts and esters processes for the preparation of these compounds their use as pharmaceuticals pharmaceutical preparations and novel phenols and thiophenols - Google Patents

Novel 6-phenoxymethyl-4- hydroxytetrahydropyran-2-ones and 6-thiophenoxymethyl-4-hydroxytetrahydropyran-2- ones and the corresponding dihydroxycarboxylic acid derivatives salts and esters processes for the preparation of these compounds their use as pharmaceuticals pharmaceutical preparations and novel phenols and thiophenols Download PDF

Info

Publication number: PH26257A
Authority: PH; Philippines
Prior art keywords: formula; solution; hydroxytetrahydropyran; ones; compounds
Prior art date: 1988-05-13

Application number

PH38636A

Other languages

English (en)

Inventor

Heiner Jendralla

Gerhard Beck

Gunther Wess

Wilheim Bartmann

Original Assignee

Hoechst Ag

Priority date (The priority date 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 date listed.)

1988-05-13

Filing date

1989-05-11

Publication date

1992-04-01

1988-05-13 Priority claimed from DE3816388A external-priority patent/DE3816388A1/de

1988-06-11 Priority claimed from DE19883819999 external-priority patent/DE3819999A1/de

1989-05-11 Application filed by Hoechst Ag filed Critical Hoechst Ag

1992-04-01 Publication of PH26257A publication Critical patent/PH26257A/en

Links

150000001875 compounds Chemical class 0.000 title claims description 64
-1 dihydroxycarboxylic acid derivatives salts Chemical class 0.000 title claims description 26
238000000034 method Methods 0.000 title claims description 13
150000002148 esters Chemical class 0.000 title claims description 11
239000000825 pharmaceutical preparation Substances 0.000 title claims description 3
238000002360 preparation method Methods 0.000 title description 8
230000008569 process Effects 0.000 title description 7
150000002989 phenols Chemical class 0.000 title description 6
239000003814 drug Substances 0.000 title description 2
WWRUMEPVBDVWTM-UHFFFAOYSA-N 4-hydroxy-6-(phenoxymethyl)oxan-2-one Chemical class O1C(=O)CC(O)CC1COC1=CC=CC=C1 WWRUMEPVBDVWTM-UHFFFAOYSA-N 0.000 title 1
KUWPQLRPLIACDU-UHFFFAOYSA-N 4-hydroxy-6-(phenylsulfanylmethyl)oxan-2-one Chemical class S(C1=CC=CC=C1)CC1CC(CC(O1)=O)O KUWPQLRPLIACDU-UHFFFAOYSA-N 0.000 title 1
125000004432 carbon atom Chemical group C* 0.000 claims description 22
229910052736 halogen Inorganic materials 0.000 claims description 15
150000002367 halogens Chemical class 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 3
ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
241000124008 Mammalia Species 0.000 claims 2
206010003210 Arteriosclerosis Diseases 0.000 claims 1
241000238370 Sepia Species 0.000 claims 1
208000011775 arteriosclerosis disease Diseases 0.000 claims 1
150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
229940125904 compound 1 Drugs 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 87
239000000243 solution Substances 0.000 description 59
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 52
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 35
239000000203 mixture Substances 0.000 description 32
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 19
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
238000002844 melting Methods 0.000 description 18
230000008018 melting Effects 0.000 description 18
239000000047 product Substances 0.000 description 18
238000010168 coupling process Methods 0.000 description 17
238000005859 coupling reaction Methods 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 16
239000007787 solid Substances 0.000 description 16
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 14
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
230000015572 biosynthetic process Effects 0.000 description 13
239000003921 oil Substances 0.000 description 13
235000019198 oils Nutrition 0.000 description 13
125000001424 substituent group Chemical group 0.000 description 13
238000005481 NMR spectroscopy Methods 0.000 description 11
239000002253 acid Substances 0.000 description 11
235000012000 cholesterol Nutrition 0.000 description 11
150000003839 salts Chemical class 0.000 description 11
238000003786 synthesis reaction Methods 0.000 description 11
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
238000001816 cooling Methods 0.000 description 10
230000008878 coupling Effects 0.000 description 10
239000000741 silica gel Substances 0.000 description 10
229910002027 silica gel Inorganic materials 0.000 description 10
239000011734 sodium Substances 0.000 description 10
239000000725 suspension Substances 0.000 description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
150000002596 lactones Chemical class 0.000 description 9
229910052708 sodium Inorganic materials 0.000 description 9
238000004809 thin layer chromatography Methods 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
229910052799 carbon Inorganic materials 0.000 description 8
239000000284 extract Substances 0.000 description 8
150000007513 acids Chemical class 0.000 description 7
210000004027 cell Anatomy 0.000 description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
239000000843 powder Substances 0.000 description 7
239000002904 solvent Substances 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
125000003545 alkoxy group Chemical group 0.000 description 6
238000009835 boiling Methods 0.000 description 6
MMCOUVMKNAHQOY-UHFFFAOYSA-N carbonoperoxoic acid Chemical class OOC(O)=O MMCOUVMKNAHQOY-UHFFFAOYSA-N 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 6
230000005764 inhibitory process Effects 0.000 description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
229920006395 saturated elastomer Polymers 0.000 description 6
239000007858 starting material Substances 0.000 description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 5
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 5
238000007792 addition Methods 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
239000012230 colorless oil Substances 0.000 description 5
239000010949 copper Substances 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 5
229910052740 iodine Inorganic materials 0.000 description 5
239000012071 phase Substances 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
159000000000 sodium salts Chemical class 0.000 description 5
238000012360 testing method Methods 0.000 description 5
238000005160 1H NMR spectroscopy Methods 0.000 description 4
102000004190 Enzymes Human genes 0.000 description 4
108090000790 Enzymes Proteins 0.000 description 4
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
102000004286 Hydroxymethylglutaryl CoA Reductases Human genes 0.000 description 4
108090000895 Hydroxymethylglutaryl CoA Reductases Proteins 0.000 description 4
102000004316 Oxidoreductases Human genes 0.000 description 4
108090000854 Oxidoreductases Proteins 0.000 description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
201000010099 disease Diseases 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
230000000694 effects Effects 0.000 description 4
229940088598 enzyme Drugs 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
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 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
KQDJTBPASNJQFQ-UHFFFAOYSA-N 2-iodophenol Chemical class OC1=CC=CC=C1I KQDJTBPASNJQFQ-UHFFFAOYSA-N 0.000 description 3
MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
201000001320 Atherosclerosis Diseases 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
238000005801 aryl-aryl coupling reaction Methods 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
239000000499 gel Substances 0.000 description 3
150000004795 grignard reagents Chemical class 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
239000011630 iodine Substances 0.000 description 3
239000010410 layer Substances 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
230000002265 prevention Effects 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
230000009467 reduction Effects 0.000 description 3
150000003385 sodium Chemical class 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Substances C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 3
CABVTRNMFUVUDM-VRHQGPGLSA-N (3S)-3-hydroxy-3-methylglutaryl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C[C@@](O)(CC(O)=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 CABVTRNMFUVUDM-VRHQGPGLSA-N 0.000 description 2
KJTLQQUUPVSXIM-ZCFIWIBFSA-N (R)-mevalonic acid Chemical compound OCC[C@](O)(C)CC(O)=O KJTLQQUUPVSXIM-ZCFIWIBFSA-N 0.000 description 2
AITNMTXHTIIIBB-UHFFFAOYSA-N 1-bromo-4-fluorobenzene Chemical class FC1=CC=C(Br)C=C1 AITNMTXHTIIIBB-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
239000007818 Grignard reagent Substances 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 description 2
LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Natural products OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 2
239000000654 additive Substances 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
150000001502 aryl halides Chemical class 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
229940073608 benzyl chloride Drugs 0.000 description 2
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
210000000941 bile Anatomy 0.000 description 2
239000003613 bile acid Substances 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
238000006555 catalytic reaction Methods 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000006114 decarboxylation reaction Methods 0.000 description 2
238000011161 development Methods 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000010828 elution Methods 0.000 description 2
230000007717 exclusion Effects 0.000 description 2
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 2
125000001207 fluorophenyl group Chemical group 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
239000012535 impurity Substances 0.000 description 2
238000011534 incubation Methods 0.000 description 2
PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 description 2
QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
AGJSNMGHAVDLRQ-IWFBPKFRSA-N methyl (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-IWFBPKFRSA-N 0.000 description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
102000004169 proteins and genes Human genes 0.000 description 2
108090000623 proteins and genes Proteins 0.000 description 2
238000000746 purification Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
229960004889 salicylic acid Drugs 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
238000003756 stirring Methods 0.000 description 2
VEPTXBCIDSFGBF-UHFFFAOYSA-M tetrabutylazanium;fluoride;trihydrate Chemical compound O.O.O.[F-].CCCC[N+](CCCC)(CCCC)CCCC VEPTXBCIDSFGBF-UHFFFAOYSA-M 0.000 description 2
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical group SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 2
URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
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238000010537 deprotonation reaction Methods 0.000 description 1
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229940079919 digestives enzyme preparation Drugs 0.000 description 1
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239000007788 liquid Substances 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
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BLQJIBCZHWBKSL-UHFFFAOYSA-L magnesium iodide Chemical compound [Mg+2].[I-].[I-] BLQJIBCZHWBKSL-UHFFFAOYSA-L 0.000 description 1
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238000010907 mechanical stirring Methods 0.000 description 1
AGJSNMGHAVDLRQ-HUUJSLGLSA-N methyl (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-HUUJSLGLSA-N 0.000 description 1
210000001589 microsome Anatomy 0.000 description 1
239000012452 mother liquor Substances 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
VOKXPKSMYJLAIW-UHFFFAOYSA-N nickel;phosphane Chemical class P.[Ni] VOKXPKSMYJLAIW-UHFFFAOYSA-N 0.000 description 1
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231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
238000006384 oligomerization reaction Methods 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
QJPQVXSHYBGQGM-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 QJPQVXSHYBGQGM-UHFFFAOYSA-N 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920001282 polysaccharide Polymers 0.000 description 1
239000005017 polysaccharide Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 description 1
229960002965 pravastatin Drugs 0.000 description 1
238000011533 pre-incubation Methods 0.000 description 1
XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 1
GPKJTRJOBQGKQK-UHFFFAOYSA-N quinacrine Chemical compound C1=C(OC)C=C2C(NC(C)CCCN(CC)CC)=C(C=CC(Cl)=C3)C3=NC2=C1 GPKJTRJOBQGKQK-UHFFFAOYSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
229910052761 rare earth metal Inorganic materials 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 description 1
238000006894 reductive elimination reaction Methods 0.000 description 1
238000012552 review Methods 0.000 description 1
230000033764 rhythmic process Effects 0.000 description 1
230000028327 secretion Effects 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
230000002226 simultaneous effect Effects 0.000 description 1
RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
229940032330 sulfuric acid Drugs 0.000 description 1
239000002600 sunflower oil Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
238000012353 t test Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
229960002622 triacetin Drugs 0.000 description 1
229910052722 tritium Inorganic materials 0.000 description 1
238000000825 ultraviolet detection Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- 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
- C07C323/01—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 halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton
- C07C323/09—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 halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton having sulfur atoms of thio groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- 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

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Obesity (AREA)
Diabetes (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Hematology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (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)
Pyrane Compounds (AREA)

PH38636A 1988-05-13 1989-05-11 Novel 6-phenoxymethyl-4- hydroxytetrahydropyran-2-ones and 6-thiophenoxymethyl-4-hydroxytetrahydropyran-2- ones and the corresponding dihydroxycarboxylic acid derivatives salts and esters processes for the preparation of these compounds their use as pharmaceuticals pharmaceutical preparations and novel phenols and thiophenols PH26257A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE3816388A DE3816388A1 (de)	1988-05-13	1988-05-13	Neue-6-phenoxymethyl-4-hydroxytetrahydropyran-2-one und 6-thiophenoxymethyl-4-hydroxytetrahydropyran-2-one, verfahren zu ihrer herstellung, ihre verwendung als arzneimittel, pharmazeutische praeparate und neue phenole sowie thiophenole
DE19883819999 DE3819999A1 (de)	1988-06-11	1988-06-11	Neue 6-phenoxymethyl-4-hydroxytetrahydropyran-2-one und 6-thiphenoxymethyl-4-hydroxytetrahydropyran-2 -one, sowie die entsprechenden dihydroxycarbonsaeurederivate, salze und ester, verfahren zur herstellung dieser verbindung, ihre verwendung als arzneimittel, pharmazeutische praeparate und neue phenole sowie thiophenole

Publications (1)

Publication Number	Publication Date
PH26257A true PH26257A (en)	1992-04-01

Family

ID=25868078

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PH38636A PH26257A (en)	1988-05-13	1989-05-11	Novel 6-phenoxymethyl-4- hydroxytetrahydropyran-2-ones and 6-thiophenoxymethyl-4-hydroxytetrahydropyran-2- ones and the corresponding dihydroxycarboxylic acid derivatives salts and esters processes for the preparation of these compounds their use as pharmaceuticals pharmaceutical preparations and novel phenols and thiophenols

Country Status (16)

Country	Link
EP (1)	EP0341681B1 (fr)
JP (1)	JP2833779B2 (fr)
KR (1)	KR900018062A (fr)
AU (1)	AU615060B2 (fr)
CA (1)	CA1338018C (fr)
DE (1)	DE58906520D1 (fr)
DK (1)	DK235389A (fr)
ES (1)	ES2061779T3 (fr)
FI (1)	FI96684C (fr)
HU (1)	HU206312B (fr)
IE (1)	IE63298B1 (fr)
IL (1)	IL90249A (fr)
NO (1)	NO172538C (fr)
NZ (1)	NZ229083A (fr)
PH (1)	PH26257A (fr)
PT (1)	PT90532B (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3929913A1 (de) *	1989-09-08	1991-04-04	Hoechst Ag	4-hydroxytetrahydropyran-2-one sowie die entsprechenden dihydroxycarbonsaeurederivate, salze und ester, verfahren zu ihrer herstellung, ihre verwendung als arzneimittel, pharmazeutische praeparate sowie vorprodukte
KR950005791A (ko) *	1993-08-09	1995-03-20	후꾸야마 마사루	카르복실산 에스테르-유도체의 제조방법 및 그 방법에 사용되는 4- 플루오로비페닐 유도체
JP6186974B2 (ja) *	2012-07-30	2017-08-30	Jnc株式会社	液晶組成物、酸化防止剤および液晶表示素子

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3674521D1 (de) *	1985-08-29	1990-10-31	Hoechst Ag	6-phenoxymethyl-4-hydroxytetrahydropyran-2-one, verfahren zu ihrer herstellung, ihre verwendung als arzneimittel, pharmazeutische praeparate und zwischenprodukte.
DE3530798A1 (de) *	1985-08-29	1987-03-05	Hoechst Ag	6-phenoxymethyl-4-hydroxytetrahydropyran-2-one, verfahren zu ihrer herstellung, ihre verwendung als arzneimittel, pharmazeutische praeparate und zwischenprodukte
DE3632893A1 (de) *	1986-09-27	1988-04-07	Hoechst Ag	4-(r)-hydroxy-6(s)-arylthiomethyl-tetrahydropyran-2-one, deren entsprechende sulfoxide und sulfone, verfahren zu ihrer herstellung, ihre verwendung als arzneimittel, pharmazeutische praeparate und zwischenprodukte
DE3929913A1 (de) *	1989-09-08	1991-04-04	Hoechst Ag	4-hydroxytetrahydropyran-2-one sowie die entsprechenden dihydroxycarbonsaeurederivate, salze und ester, verfahren zu ihrer herstellung, ihre verwendung als arzneimittel, pharmazeutische praeparate sowie vorprodukte

1989
- 1989-05-09 IL IL9024989A patent/IL90249A/en not_active IP Right Cessation
- 1989-05-10 EP EP89108378A patent/EP0341681B1/fr not_active Expired - Lifetime
- 1989-05-10 DE DE89108378T patent/DE58906520D1/de not_active Expired - Lifetime
- 1989-05-10 ES ES89108378T patent/ES2061779T3/es not_active Expired - Lifetime
- 1989-05-11 PT PT90532A patent/PT90532B/pt not_active IP Right Cessation
- 1989-05-11 PH PH38636A patent/PH26257A/en unknown
- 1989-05-11 NZ NZ229083A patent/NZ229083A/en unknown
- 1989-05-11 FI FI892291A patent/FI96684C/fi not_active IP Right Cessation
- 1989-05-12 JP JP1117649A patent/JP2833779B2/ja not_active Expired - Lifetime
- 1989-05-12 AU AU34715/89A patent/AU615060B2/en not_active Ceased
- 1989-05-12 DK DK235389A patent/DK235389A/da not_active Application Discontinuation
- 1989-05-12 IE IE155489A patent/IE63298B1/en not_active IP Right Cessation
- 1989-05-12 NO NO891937A patent/NO172538C/no unknown
- 1989-05-12 HU HU892394A patent/HU206312B/hu not_active IP Right Cessation
- 1989-05-12 CA CA000599613A patent/CA1338018C/fr not_active Expired - Fee Related
- 1989-05-13 KR KR1019890006399A patent/KR900018062A/ko not_active Abandoned

Also Published As

Publication number	Publication date
EP0341681A3 (en)	1990-05-16
KR900018062A (ko)	1990-12-20
FI96684B (fi)	1996-04-30
AU615060B2 (en)	1991-09-19
PT90532A (pt)	1989-11-30
AU3471589A (en)	1989-12-21
EP0341681A2 (fr)	1989-11-15
HU206312B (en)	1992-10-28
ES2061779T3 (es)	1994-12-16
HUT58309A (en)	1992-02-28
NO891937L (no)	1989-11-14
PT90532B (pt)	1994-11-30
JP2833779B2 (ja)	1998-12-09
CA1338018C (fr)	1996-01-30
NO172538C (no)	1993-08-04
FI96684C (fi)	1996-08-12
IL90249A0 (en)	1989-12-15
NZ229083A (en)	1990-12-21
JPH01319472A (ja)	1989-12-25
IE891554L (en)	1989-11-13
DE58906520D1 (de)	1994-02-10
FI892291A7 (fi)	1989-11-14
DK235389A (da)	1989-11-14
IE63298B1 (en)	1995-04-05
DK235389D0 (da)	1989-05-12
NO891937D0 (no)	1989-05-12
IL90249A (en)	1994-01-25
EP0341681B1 (fr)	1993-12-29
FI892291A0 (fi)	1989-05-11
NO172538B (no)	1993-04-26

Publication	Publication Date	Title
CA1124244A (fr)	1982-05-25	Derives de l'imidazole, procede de preparation de composes pharmaceutiques les contenant
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DE69524428T2 (de)	2002-05-23	Dihydrobenzofuran und verwandte verbindungen als entzündungshemmende mittel
CA1060888A (fr)	1979-08-21	Derives du cyclopentane
EP0132130B1 (fr)	1990-03-07	Acides aroylbenzofuranyl-acétiques et -propioniques, acides aroylbenzothiényl-acétiques et -propioniques, procédé pour leur préparation et composition pharmaceutiques les contenant
EP0062921A1 (fr)	1982-10-20	Dérivés d'adénosine
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Faigl et al.	1997	Competition and co-operation between ortho directing groups and activating agents: Regioselective metallation of 1-(methoxyphenyl) pyrroles
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JP3164157B2 (ja)	2001-05-08	抗炎症薬として有用なジヒドロベンゾフランおよび関連化合物
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DE19958246A1 (de)	2000-06-15	Isochinuclidinderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende therapeutische Mittel gegen Hypercholesterinämie
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GB2120663A (en)	1983-12-07	Allylamine derivatives, processes for their preparation and their use
US4816473A (en)	1989-03-28	Aroyl benzofuran and benzothiophene acetic and propionic acids
US4970234A (en)	1990-11-13	Furyl, phenylene, and thienyl leukotriene B4 analogues
PH26748A (en)	1992-09-28	Substituted dibenzofurans and methods of using same
US4970229A (en)	1990-11-13	Furyl, phenylene, and thienyl leukotriene B4 analogues
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Meese et al.	1986	Dimethyl 3, 3, 4, 4,. 5,. 5, 6, 6‐(2H8)‐6‐methoxycarbonyl‐2‐oxo‐hexanephosphonate, a versatile reagent for the synthesis of deuterated ω‐carboxy prostanoids