PH26375A - 7-[1H-pyrrol-3-yl]-substituted 3,5-dihydroxyhept-6-enoic acids-7-[1H-pyrrol-3-YL]-substituted 3,5-dihydroxyheptanoic acids and their pharmaceutical preparation thereof - Google Patents

7-[1H-pyrrol-3-yl]-substituted 3,5-dihydroxyhept-6-enoic acids-7-[1H-pyrrol-3-YL]-substituted 3,5-dihydroxyheptanoic acids and their pharmaceutical preparation thereof Download PDF

Info

Publication number: PH26375A
Authority: PH; Philippines
Prior art keywords: fluorophenyl; formula; isopropyl; denotes; phenyl
Prior art date: 1987-07-10

Application number

PH37199A

Other languages

English (en)

Inventor

Heiner Jendralla

Gerhard Beck

Ekkehard Baader

Bela Kerekjarto

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.)

1987-07-10

Filing date

1988-07-08

Publication date

1992-06-01

1988-07-08 Application filed by Hoechst Ag filed Critical Hoechst Ag

1992-06-01 Publication of PH26375A publication Critical patent/PH26375A/en

Links

239000000825 pharmaceutical preparation Substances 0.000 title claims description 4
PDBMVYIMAMQDCW-UHFFFAOYSA-N 3,5-dihydroxyheptanoic acid Chemical class CCC(O)CC(O)CC(O)=O PDBMVYIMAMQDCW-UHFFFAOYSA-N 0.000 title 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 67
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 62
150000001875 compounds Chemical class 0.000 claims description 50
238000000034 method Methods 0.000 claims description 41
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 40
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 32
-1 ethanediyl group Chemical group 0.000 claims description 24
239000002253 acid Substances 0.000 claims description 21
239000011734 sodium Substances 0.000 claims description 21
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 claims description 18
229910052708 sodium Inorganic materials 0.000 claims description 18
150000007513 acids Chemical class 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 14
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 12
125000004429 atom Chemical group 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 9
229910052731 fluorine Inorganic materials 0.000 claims description 9
239000011737 fluorine Substances 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
208000035150 Hypercholesterolemia Diseases 0.000 claims description 2
240000008042 Zea mays Species 0.000 claims description 2
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 2
235000002017 Zea mays subsp mays Nutrition 0.000 claims description 2
239000003513 alkali Substances 0.000 claims description 2
235000005822 corn Nutrition 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims 2
150000002431 hydrogen Chemical class 0.000 claims 2
102100033356 Lecithin retinol acyltransferase Human genes 0.000 claims 1
125000000753 cycloalkyl group Chemical group 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
239000000835 fiber Substances 0.000 claims 1
108010084957 lecithin-retinol acyltransferase Proteins 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
239000000243 solution Substances 0.000 description 58
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 56
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 51
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
239000000203 mixture Substances 0.000 description 39
239000007787 solid Substances 0.000 description 38
239000000047 product Substances 0.000 description 37
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 31
239000000460 chlorine Substances 0.000 description 29
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
238000002844 melting Methods 0.000 description 26
230000008018 melting Effects 0.000 description 26
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 25
125000001207 fluorophenyl group Chemical group 0.000 description 24
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 23
230000015572 biosynthetic process Effects 0.000 description 23
238000006243 chemical reaction Methods 0.000 description 22
150000001299 aldehydes Chemical class 0.000 description 20
235000019439 ethyl acetate Nutrition 0.000 description 20
239000000741 silica gel Substances 0.000 description 20
229910002027 silica gel Inorganic materials 0.000 description 20
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 20
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
230000008569 process Effects 0.000 description 19
239000003921 oil Substances 0.000 description 17
235000019198 oils Nutrition 0.000 description 17
229910052761 rare earth metal Inorganic materials 0.000 description 17
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 16
150000002148 esters Chemical class 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 15
238000003786 synthesis reaction Methods 0.000 description 14
239000004698 Polyethylene Substances 0.000 description 13
235000012000 cholesterol Nutrition 0.000 description 13
239000011651 chromium Substances 0.000 description 13
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
239000000706 filtrate Substances 0.000 description 13
239000002904 solvent Substances 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
102220047090 rs6152 Human genes 0.000 description 12
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
238000010992 reflux Methods 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 10
238000002360 preparation method Methods 0.000 description 10
239000000725 suspension Substances 0.000 description 10
150000003931 anilides Chemical class 0.000 description 8
125000000623 heterocyclic group Chemical group 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
230000009467 reduction Effects 0.000 description 8
239000013078 crystal Substances 0.000 description 7
230000005764 inhibitory process Effects 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
102000004190 Enzymes Human genes 0.000 description 6
108090000790 Enzymes Proteins 0.000 description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 6
229930194542 Keto Natural products 0.000 description 6
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
108090000854 Oxidoreductases Proteins 0.000 description 6
102000004316 Oxidoreductases Human genes 0.000 description 6
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
238000007792 addition Methods 0.000 description 6
229910052794 bromium Inorganic materials 0.000 description 6
210000004027 cell Anatomy 0.000 description 6
229910052801 chlorine Inorganic materials 0.000 description 6
238000012053 enzymatic serum creatinine assay Methods 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
239000012267 brine Substances 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
238000004113 cell culture Methods 0.000 description 5
238000004821 distillation Methods 0.000 description 5
229910052740 iodine Inorganic materials 0.000 description 5
125000000468 ketone group Chemical group 0.000 description 5
150000002596 lactones Chemical class 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
239000012071 phase Substances 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
239000007858 starting material Substances 0.000 description 5
125000001424 substituent group Chemical group 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
239000008186 active pharmaceutical agent Substances 0.000 description 4
239000012230 colorless oil Substances 0.000 description 4
238000005984 hydrogenation reaction Methods 0.000 description 4
239000011777 magnesium Substances 0.000 description 4
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
150000004702 methyl esters Chemical class 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
238000007254 oxidation reaction Methods 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
239000002243 precursor Substances 0.000 description 4
230000002829 reductive effect Effects 0.000 description 4
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 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 3
241000282326 Felis catus Species 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
102000004286 Hydroxymethylglutaryl CoA Reductases Human genes 0.000 description 3
108090000895 Hydroxymethylglutaryl CoA Reductases Proteins 0.000 description 3
LXZBFUBRYYVRQJ-UHFFFAOYSA-M Lovastatin hydroxy acid Chemical class [Na+].C1=CC(C)C(CCC(O)CC(O)CC([O-])=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 LXZBFUBRYYVRQJ-UHFFFAOYSA-M 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
230000008901 benefit Effects 0.000 description 3
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 3
239000003245 coal Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
150000004678 hydrides Chemical class 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
239000002480 mineral oil Substances 0.000 description 3
235000010446 mineral oil Nutrition 0.000 description 3
239000012452 mother liquor Substances 0.000 description 3
150000002825 nitriles Chemical class 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
230000036961 partial effect Effects 0.000 description 3
239000000843 powder Substances 0.000 description 3
230000001681 protective effect Effects 0.000 description 3
239000011347 resin Substances 0.000 description 3
229920005989 resin Polymers 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
150000003385 sodium Chemical class 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
235000012976 tarts Nutrition 0.000 description 3
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 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
CHNYVNOFAWYUEG-UHFFFAOYSA-N 1h-pyrrole-3-carbaldehyde Chemical compound O=CC=1C=CNC=1 CHNYVNOFAWYUEG-UHFFFAOYSA-N 0.000 description 2
HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 2
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
VGMFHMLQOYWYHN-UHFFFAOYSA-N Compactin Natural products OCC1OC(OC2C(O)C(O)C(CO)OC2Oc3cc(O)c4C(=O)C(=COc4c3)c5ccc(O)c(O)c5)C(O)C(O)C1O VGMFHMLQOYWYHN-UHFFFAOYSA-N 0.000 description 2
KJTLQQUUPVSXIM-UHFFFAOYSA-N DL-mevalonic acid Natural products OCCC(O)(C)CC(O)=O KJTLQQUUPVSXIM-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
102100039250 Essential MCU regulator, mitochondrial Human genes 0.000 description 2
101000813097 Homo sapiens Essential MCU regulator, mitochondrial Proteins 0.000 description 2
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 2
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
150000001204 N-oxides Chemical class 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
241000183024 Populus tremula Species 0.000 description 2
235000014443 Pyrus communis Nutrition 0.000 description 2
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
AJLFOPYRIVGYMJ-UHFFFAOYSA-N SJ000287055 Natural products C12C(OC(=O)C(C)CC)CCC=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 AJLFOPYRIVGYMJ-UHFFFAOYSA-N 0.000 description 2
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FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
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239000007983 Tris buffer Substances 0.000 description 2
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JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
229940051881 anilide analgesics and antipyretics Drugs 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
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125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
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HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
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239000003153 chemical reaction reagent Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
229940117975 chromium trioxide Drugs 0.000 description 2
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238000000354 decomposition reaction Methods 0.000 description 2
235000013367 dietary fats Nutrition 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000010828 elution Methods 0.000 description 2
QPMJENKZJUFOON-PLNGDYQASA-N ethyl (z)-3-chloro-2-cyano-4,4,4-trifluorobut-2-enoate Chemical compound CCOC(=O)C(\C#N)=C(/Cl)C(F)(F)F QPMJENKZJUFOON-PLNGDYQASA-N 0.000 description 2
238000009472 formulation Methods 0.000 description 2
239000010520 ghee Substances 0.000 description 2
150000003278 haem Chemical class 0.000 description 2
125000005343 heterocyclic alkyl group Chemical group 0.000 description 2
230000000055 hyoplipidemic effect Effects 0.000 description 2
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230000002401 inhibitory effect Effects 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
150000002632 lipids Chemical class 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
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ITRHZWKEZJYJQO-UHFFFAOYSA-N gamma-costol Natural products C1C(C(=C)CO)CCC2(C)CCCC(C)=C21 ITRHZWKEZJYJQO-UHFFFAOYSA-N 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000001087 glyceryl triacetate Substances 0.000 description 1
235000013773 glyceryl triacetate Nutrition 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
238000000291 inelastic electron tunnelling spectroscopy Methods 0.000 description 1
101150032953 ins1 gene Proteins 0.000 description 1
239000011630 iodine Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
210000001853 liver microsome Anatomy 0.000 description 1
235000015250 liver sausages Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
235000019988 mead Nutrition 0.000 description 1
238000010907 mechanical stirring Methods 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
WPHGSKGZRAQSGP-UHFFFAOYSA-N methylenecyclohexane Natural products C1CCCC2CC21 WPHGSKGZRAQSGP-UHFFFAOYSA-N 0.000 description 1
VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
MZPAQCAPWLAKSD-UHFFFAOYSA-N n-phenyl-1h-pyrrole-2-carboxamide Chemical compound C=1C=CNC=1C(=O)NC1=CC=CC=C1 MZPAQCAPWLAKSD-UHFFFAOYSA-N 0.000 description 1
101150115538 nero gene Proteins 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
229960003512 nicotinic acid Drugs 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
RPMXALUWKZHYOV-UHFFFAOYSA-N nitroethene Chemical group [O-][N+](=O)C=C RPMXALUWKZHYOV-UHFFFAOYSA-N 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
208000014380 ornithine aminotransferase deficiency Diseases 0.000 description 1
210000001672 ovary Anatomy 0.000 description 1
MQHIQUBXFFAOMK-UHFFFAOYSA-N pazopanib hydrochloride Chemical compound Cl.C1=CC2=C(C)N(C)N=C2C=C1N(C)C(N=1)=CC=NC=1NC1=CC=C(C)C(S(N)(=O)=O)=C1 MQHIQUBXFFAOMK-UHFFFAOYSA-N 0.000 description 1
150000004714 phosphonium salts Chemical class 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
239000011148 porous material Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 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
230000002265 prevention Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
UWYCMJHIERYINA-UHFFFAOYSA-N pyrrol-1-ylmethanol Chemical compound OCN1C=CC=C1 UWYCMJHIERYINA-UHFFFAOYSA-N 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
229910052704 radon Inorganic materials 0.000 description 1
SYUHGPGVQRZVTB-UHFFFAOYSA-N radon atom Chemical compound [Rn] SYUHGPGVQRZVTB-UHFFFAOYSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000001172 regenerating effect Effects 0.000 description 1
238000002271 resection Methods 0.000 description 1
NXLOLUFNDSBYTP-UHFFFAOYSA-N retene Chemical compound C1=CC=C2C3=CC=C(C(C)C)C=C3C=CC2=C1C NXLOLUFNDSBYTP-UHFFFAOYSA-N 0.000 description 1
108010035322 rhamnogalacturonan acetylesterase Proteins 0.000 description 1
230000033764 rhythmic process Effects 0.000 description 1
FESBVLZDDCQLFY-UHFFFAOYSA-N sete Chemical compound [Te]=[Se] FESBVLZDDCQLFY-UHFFFAOYSA-N 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical class [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000010959 steel Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
239000002600 sunflower oil Substances 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
229910052715 tantalum Inorganic materials 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
229960002622 triacetin Drugs 0.000 description 1
LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
238000001665 trituration Methods 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
101150070667 ureD gene Proteins 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
235000014101 wine Nutrition 0.000 description 1
CZPRKINNVBONSF-UHFFFAOYSA-M zinc;dioxido(oxo)phosphanium Chemical compound [Zn+2].[O-][P+]([O-])=O CZPRKINNVBONSF-UHFFFAOYSA-M 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/337—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
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Obesity (AREA)
Diabetes (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Hematology (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)
Pyrrole Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)

PH37199A 1987-07-10 1988-07-08 7-[1H-pyrrol-3-yl]-substituted 3,5-dihydroxyhept-6-enoic acids-7-[1H-pyrrol-3-YL]-substituted 3,5-dihydroxyheptanoic acids and their pharmaceutical preparation thereof PH26375A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19873722806 DE3722806A1 (de)	1987-07-10	1987-07-10	7-(1h-pyrrol-3-yl)-substituierte 3,5-dihydroxy-hept-6-ensaeuren, 7-(1h-pyrrol-3-yl)-substituierte 3,5-dihydroxy-heptansaeuren, ihre entsprechenden (delta)-lactone und salze, verfahren zu ihrer herstellung ihre verwendung als arzneimittel, pharmazeutische praeparate und zwischenprodukte

Publications (1)

Publication Number	Publication Date
PH26375A true PH26375A (en)	1992-06-01

Family

ID=6331291

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PH37199A PH26375A (en)	1987-07-10	1988-07-08	7-[1H-pyrrol-3-yl]-substituted 3,5-dihydroxyhept-6-enoic acids-7-[1H-pyrrol-3-YL]-substituted 3,5-dihydroxyheptanoic acids and their pharmaceutical preparation thereof

Country Status (19)

Country	Link
US (1)	US5055484A (es)
EP (1)	EP0300249B1 (es)
JP (1)	JPS6434959A (es)
KR (1)	KR890002135A (es)
AT (1)	ATE85324T1 (es)
AU (1)	AU1888088A (es)
DE (2)	DE3722806A1 (es)
DK (1)	DK384288A (es)
ES (1)	ES2043736T3 (es)
FI (1)	FI883247A7 (es)
GR (1)	GR3007611T3 (es)
HU (1)	HU208672B (es)
IE (1)	IE63205B1 (es)
IL (1)	IL87036A0 (es)
NO (1)	NO883072L (es)
NZ (1)	NZ225342A (es)
PH (1)	PH26375A (es)
PT (1)	PT87927B (es)
ZA (1)	ZA884918B (es)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3826814A1 (de) *	1988-08-06	1990-02-08	Hoechst Ag	Neue 6-fluor-3,5-dihydroxycarbonsaeuren und deren derivate, verfahren zu ihrer herstellung, ihre verwendung als arzneimittel, pharmazeutische praeparate und zwischenprodukte
FI94339C (fi) *	1989-07-21	1995-08-25	Warner Lambert Co	Menetelmä farmaseuttisesti käyttökelpoisen /R-(R,R)/-2-(4-fluorifenyyli)- , -dihydroksi-5-(1-metyylietyyli)-3-fenyyli-4-/(fenyyliamino)karbonyyli/-1H-pyrroli-1-heptaanihapon ja sen farmaseuttisesti hyväksyttävien suolojen valmistamiseksi
IT1237793B (it) *	1989-12-21	1993-06-17	Zambon Spa	Composti attivi come inibitori dell'enzima hmg-coa reduttasi
US5128366A (en) *	1990-07-05	1992-07-07	Shinogi & Co., Ltd.	Pyrrole derivatives
DE4243279A1 (de) *	1992-12-21	1994-06-23	Bayer Ag	Substituierte Triole
US7250444B2 (en) *	2003-08-11	2007-07-31	Pfizer Inc.	Pyrrole-based HMG-CoA reductase inhibitors

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3928380A (en) *	1973-03-29	1975-12-23	Sterling Drug Inc	1,1{40 -Spirobis(cyclopenta-{8 4,5-c{9 pyrroles)
US4647576A (en) *	1984-09-24	1987-03-03	Warner-Lambert Company	Trans-6-[2-(substitutedpyrrol-1-yl)alkyl]-pyran-2-one inhibitors of cholesterol synthesis
US4851427A (en) *	1985-10-25	1989-07-25	Sandoz Pharm. Corp.	Pyrrole analogs of mevalonolactone, derivatives thereof and pharmaceutical use
AU598775B2 (en) *	1985-10-25	1990-07-05	Sandoz Ag	Heterocyclic analogs of mevalonolactone
US4681893A (en) *	1986-05-30	1987-07-21	Warner-Lambert Company	Trans-6-[2-(3- or 4-carboxamido-substituted pyrrol-1-yl)alkyl]-4-hydroxypyran-2-one inhibitors of cholesterol synthesis
NO881411L (no) *	1987-04-14	1988-10-17	Bayer Ag	Substituerte pyrroler.

1987
- 1987-07-10 DE DE19873722806 patent/DE3722806A1/de not_active Withdrawn
1988
- 1988-07-01 EP EP88110533A patent/EP0300249B1/de not_active Expired - Lifetime
- 1988-07-01 ES ES88110533T patent/ES2043736T3/es not_active Expired - Lifetime
- 1988-07-01 DE DE8888110533T patent/DE3878067D1/de not_active Expired - Fee Related
- 1988-07-01 AT AT88110533T patent/ATE85324T1/de not_active IP Right Cessation
- 1988-07-07 FI FI883247A patent/FI883247A7/fi not_active Application Discontinuation
- 1988-07-07 PT PT87927A patent/PT87927B/pt not_active IP Right Cessation
- 1988-07-08 IL IL87036A patent/IL87036A0/xx unknown
- 1988-07-08 ZA ZA884918A patent/ZA884918B/xx unknown
- 1988-07-08 AU AU18880/88A patent/AU1888088A/en not_active Abandoned
- 1988-07-08 JP JP63169159A patent/JPS6434959A/ja active Pending
- 1988-07-08 NO NO88883072A patent/NO883072L/no unknown
- 1988-07-08 NZ NZ225342A patent/NZ225342A/en unknown
- 1988-07-08 DK DK384288A patent/DK384288A/da not_active Application Discontinuation
- 1988-07-08 IE IE209788A patent/IE63205B1/en not_active IP Right Cessation
- 1988-07-08 US US07/216,423 patent/US5055484A/en not_active Expired - Fee Related
- 1988-07-08 PH PH37199A patent/PH26375A/en unknown
- 1988-07-08 HU HU883600A patent/HU208672B/hu not_active IP Right Cessation
- 1988-07-09 KR KR1019880008546A patent/KR890002135A/ko not_active Withdrawn
1993
- 1993-04-09 GR GR930400426T patent/GR3007611T3/el unknown

Also Published As

Publication number	Publication date
IE63205B1 (en)	1995-04-05
FI883247A7 (fi)	1989-01-11
EP0300249A1 (de)	1989-01-25
DE3878067D1 (de)	1993-03-18
US5055484A (en)	1991-10-08
FI883247A0 (fi)	1988-07-07
GR3007611T3 (es)	1993-08-31
ATE85324T1 (de)	1993-02-15
DE3722806A1 (de)	1989-01-19
IL87036A0 (en)	1988-12-30
HU208672B (en)	1993-12-28
JPS6434959A (en)	1989-02-06
PT87927A (pt)	1989-06-30
NZ225342A (en)	1991-03-26
KR890002135A (ko)	1989-04-08
ZA884918B (en)	1989-01-18
EP0300249B1 (de)	1993-02-03
NO883072D0 (no)	1988-07-08
PT87927B (pt)	1995-03-01
NO883072L (no)	1989-01-11
IE882097L (en)	1989-01-10
HUT48580A (en)	1989-06-28
ES2043736T3 (es)	1994-01-01
DK384288D0 (da)	1988-07-08
AU1888088A (en)	1989-01-12
DK384288A (da)	1989-01-11

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ZA841734B (en)	1984-10-31	Manufacturing of kraft paper
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US5055484A (en)	1991-10-08	7(1h-pyrrol-3-yl)-substituted 3,5-dihydroxyhept-6-enoic acids, 7-(1h-pyrrol-3-yl)-substituted 3,5-dihyroxyhept-anoic acids, their corresponding delta-lactones and salts, their use as medicaments and pharmaceutical products and intermediates
JPH04234834A (ja)	1992-08-24	新規なα−マンノシダーゼ及びフコシダーゼ阻害剤
PT86821B (pt)	1992-05-29	Processo para a preparacao de novos compostos derivados de tetrazol utilizados como compostos intermedios na preparacao de compostos antihipercolesterolemicos