NO164969B - BULK MATERIAL FLUIDIZATION SYSTEM. - Google Patents
BULK MATERIAL FLUIDIZATION SYSTEM. Download PDFInfo
- Publication number
- NO164969B NO164969B NO882031A NO882031A NO164969B NO 164969 B NO164969 B NO 164969B NO 882031 A NO882031 A NO 882031A NO 882031 A NO882031 A NO 882031A NO 164969 B NO164969 B NO 164969B
- Authority
- NO
- Norway
- Prior art keywords
- cymarin
- bulk material
- digoxin
- formula
- fluidization system
- Prior art date
Links
- 239000013590 bulk material Substances 0.000 title abstract 2
- 238000005243 fluidization Methods 0.000 title 1
- XQCGNURMLWFQJR-UESCRGIISA-N Cymarin Natural products O=C[C@@]12[C@@](O)(C[C@@H](O[C@H]3O[C@@H](C)[C@@H](O)[C@@H](OC)C3)CC1)CC[C@H]1[C@]3(O)[C@@](C)([C@H](C4=CC(=O)OC4)CC3)CC[C@H]21 XQCGNURMLWFQJR-UESCRGIISA-N 0.000 claims description 15
- 229960003083 cymarin Drugs 0.000 claims description 15
- XQCGNURMLWFQJR-ZNDDOCHDSA-N Cymarin Chemical compound O1[C@H](C)[C@@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)CC[C@@H]3[C@@]2(C=O)CC1 XQCGNURMLWFQJR-ZNDDOCHDSA-N 0.000 claims description 11
- 206010019280 Heart failures Diseases 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000006260 foam Substances 0.000 abstract 1
- LTMHDMANZUZIPE-AMTYYWEZSA-N Digoxin Natural products O([C@H]1[C@H](C)O[C@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@](C)([C@H](O)C4)[C@H](C4=CC(=O)OC4)CC5)CC3)CC2)C[C@@H]1O)[C@H]1O[C@H](C)[C@@H](O[C@H]2O[C@@H](C)[C@H](O)[C@@H](O)C2)[C@@H](O)C1 LTMHDMANZUZIPE-AMTYYWEZSA-N 0.000 description 11
- 229960005156 digoxin Drugs 0.000 description 11
- LTMHDMANZUZIPE-PUGKRICDSA-N digoxin Chemical compound C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)[C@H](O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O LTMHDMANZUZIPE-PUGKRICDSA-N 0.000 description 11
- LTMHDMANZUZIPE-UHFFFAOYSA-N digoxine Natural products C1C(O)C(O)C(C)OC1OC1C(C)OC(OC2C(OC(OC3CC4C(C5C(C6(CCC(C6(C)C(O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)CC2O)C)CC1O LTMHDMANZUZIPE-UHFFFAOYSA-N 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 5
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- -1 cymarin ester Chemical class 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 206010007559 Cardiac failure congestive Diseases 0.000 description 2
- 241000511943 Strophanthus Species 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 230000000747 cardiac effect Effects 0.000 description 2
- 229940097217 cardiac glycoside Drugs 0.000 description 2
- 239000002368 cardiac glycoside Substances 0.000 description 2
- 229930182470 glycoside Natural products 0.000 description 2
- 150000002338 glycosides Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229930002534 steroid glycoside Natural products 0.000 description 2
- 150000008143 steroidal glycosides Chemical class 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 231100000816 toxic dose Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- WPKQVDYSPWCVGM-UHFFFAOYSA-N (3beta,5beta)-3-[(2,6-dideoxy-3-O-methyl-beta-D-ribo-hexopyranosyl)oxy]-5,14,19-trihydroxycard-20(22)-enolide Natural products O1C(C)C(O)C(OC)CC1OC1CC2(O)CCC3C4(O)CCC(C=5COC(=O)C=5)C4(C)CCC3C2(CO)CC1 WPKQVDYSPWCVGM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- WPKQVDYSPWCVGM-ZNDDOCHDSA-N 3-[(3S,5S,8R,9S,10R,13R,14S,17R)-5,14-dihydroxy-3-[(2R,4S,5R,6R)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-10-(hydroxymethyl)-13-methyl-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one Chemical compound O1[C@H](C)[C@@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)CC[C@@H]3[C@@]2(CO)CC1 WPKQVDYSPWCVGM-ZNDDOCHDSA-N 0.000 description 1
- 206010003658 Atrial Fibrillation Diseases 0.000 description 1
- 206010003671 Atrioventricular Block Diseases 0.000 description 1
- 208000020446 Cardiac disease Diseases 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241000208011 Digitalis Species 0.000 description 1
- 240000001879 Digitalis lutea Species 0.000 description 1
- 208000010271 Heart Block Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 206010033557 Palpitations Diseases 0.000 description 1
- 244000035964 Strophanthus nicholsonii Species 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000001746 atrial effect Effects 0.000 description 1
- 208000006218 bradycardia Diseases 0.000 description 1
- 230000036471 bradycardia Effects 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 208000028831 congenital heart disease Diseases 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000003205 diastolic effect Effects 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229940082663 other cardiac glycosides in atc Drugs 0.000 description 1
- 208000008510 paroxysmal tachycardia Diseases 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B63—SHIPS OR OTHER WATERBORNE VESSELS; RELATED EQUIPMENT
- B63B—SHIPS OR OTHER WATERBORNE VESSELS; EQUIPMENT FOR SHIPPING
- B63B27/00—Arrangement of ship-based loading or unloading equipment for cargo or passengers
- B63B27/24—Arrangement of ship-based loading or unloading equipment for cargo or passengers of pipe-lines
- B63B27/25—Arrangement of ship-based loading or unloading equipment for cargo or passengers of pipe-lines for fluidised bulk material
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B63—SHIPS OR OTHER WATERBORNE VESSELS; RELATED EQUIPMENT
- B63B—SHIPS OR OTHER WATERBORNE VESSELS; EQUIPMENT FOR SHIPPING
- B63B25/00—Load-accommodating arrangements, e.g. stowing, trimming; Vessels characterised thereby
- B63B25/02—Load-accommodating arrangements, e.g. stowing, trimming; Vessels characterised thereby for bulk goods
- B63B25/04—Load-accommodating arrangements, e.g. stowing, trimming; Vessels characterised thereby for bulk goods solid
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- B65D88/00—Large containers
- B65D88/54—Large containers characterised by means facilitating filling or emptying
- B65D88/72—Fluidising devices
Landscapes
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Combustion & Propulsion (AREA)
- Ocean & Marine Engineering (AREA)
- Pit Excavations, Shoring, Fill Or Stabilisation Of Slopes (AREA)
- Processing And Handling Of Plastics And Other Materials For Molding In General (AREA)
- Ship Loading And Unloading (AREA)
- Air Transport Of Granular Materials (AREA)
- Filling Or Discharging Of Gas Storage Vessels (AREA)
- Buffer Packaging (AREA)
Abstract
Et system for fluidisering av bulkmateriale i et fartøys (2). lasterom (3) er oppbygget av flere blokker (5) som er demonterbart montert på lasterommets (3) bunn (4) og hvis overside (6). danner en skrånende glidebane C7) mens dens lang- og kortsider (13,14) sammen med glidebanen begrenser et hulrom (17) som er fylt med et skumplastlegeme (18).A system for fluidizing bulk material in a vessel (2). cargo space (3) is made up of several blocks (5) which are removably mounted on the bottom (4) of the cargo space (3) and whose upper side (6). forms a sloping slide C7) while its long and short sides (13, 14) together with the slide define a cavity (17) which is filled with a foam body (18).
Description
Fremgangsmåte til fremstilling av 4'-monoestere Process for the production of 4'-monoesters
av cymarin for behandling av hjerteinsuffisiens. of cymarin for the treatment of heart failure.
Foreliggende oppfinnelse vedrører en fremgangsmåte til fremstilling av steroider til bruk for behandling a,v hjerteinsuffisiens, spesielt derivater av 53-card-20(22)-enolid-systemet hvis struktur er som følger: The present invention relates to a method for the production of steroids for use in the treatment of heart failure, in particular derivatives of the 53-card-20(22)-enolide system whose structure is as follows:
Denne struktur forekommer i de hjerteglykosider som tilveie-bringes fra Strophanthus spp. og Digitalis spp., hvorav flere har blitt anvendt i medisinen og vanligvis igjennom munnen. This structure occurs in the cardiac glycosides obtained from Strophanthus spp. and Digitalis spp., several of which have been used in medicine and usually by mouth.
Glykosidet digoxin (fra Digitalis lanata), 3a-tri-(g-D-di-gitoksosyl)oksy-12a,l4-dihydroksy-5g-card-20(22)-enolid, har f.eks. funnet utstrakt bruk ved behandling av pasienter med hjertelidelser, og det antas å virke på myokardinale fibre. De iaktagbare forandringer som finner-sted er en økning i den systoliske kontraksjons-kraften, en nedsettelse i hjertehastighet, en nedsettelse i diasto-lisk størrelse, og en økning i hjerteutløpet. Effekten av legemidlet på hjertet antydes ved forandringer i bølgemønsteret som vises i elek-trokardiogrammet: bradycardia, en økning av QRS-potensialet og en senkning av ST-segmentet. I toksiske doser forårsaker digoxin emesis og eventuelt død ved hjerteblokkering. Skjønt digoxin er meget potent, er det også temmelig giftig og i noen tilfeller ved f.eks. kongestiv hjertefeil er den dose som kreves for terapien nær den toksiske dose. The glycoside digoxin (from Digitalis lanata), 3a-tri-(g-D-di-gitoxosyl)oxy-12a,14-dihydroxy-5g-card-20(22)-enolide, has e.g. found extensive use in the treatment of patients with cardiac disorders, and it is believed to act on myocardial fibers. The observable changes that take place are an increase in the systolic contraction force, a decrease in heart rate, a decrease in diastolic size, and an increase in cardiac output. The effect of the drug on the heart is indicated by changes in the wave pattern shown in the electrocardiogram: bradycardia, an increase in the QRS potential and a lowering of the ST segment. In toxic doses, digoxin causes emesis and eventually death from heart block. Although digoxin is very potent, it is also quite toxic and in some cases, e.g. congestive heart failure the dose required for therapy is close to the toxic dose.
Andre hjerteglykosider har lignende virkninger på hjertet Other cardiac glycosides have similar effects on the heart
og potensen går ofte parallelt med toksisiteten. En av disse er cymarin, 3$-8-D-cymarosyloksy-5,l4-dihydroksy-19-okso-5B-card-20(22)-enolid, som har samme type virkning som digoxin på hjertefeil, men i motsetning til digoxin har det lav potens når det administreres oralt og har funnet liten anvendelse i klinisk medisin. Cymarin kan til-veiebringes fra Strophanthus spp. f.eks. S. kombé<*>, S. nicholsonii og S. ledienii. and potency often goes hand in hand with toxicity. One of these is cymarin, 3$-8-D-cymarosyloxy-5,14-dihydroxy-19-oxo-5B-card-20(22)-enolide, which has the same type of action as digoxin on heart defects, but unlike digoxin has low potency when administered orally and has found little use in clinical medicine. Cymarin can be obtained from Strophanthus spp., e.g. S. kombé<*>, S. nicholsonii and S. ledienii.
Det er nå funnet at estere med formel I kan gjenopprette hjertefeil med en mindre mengde av den orale dødlige dose enn det som er tilfelle med enten digoxin eller cymarol. It has now been found that esters of formula I can restore heart failure with a smaller amount of the oral lethal dose than is the case with either digoxin or cymarol.
Ifølge foreliggende oppfinnelse fremstilles 4<1->monoestere According to the present invention, 4<1->monoesters are produced
av cymarin med den generelle formel: of cymarin with the general formula:
hvor R er en etyl- eller propylgruppe. where R is an ethyl or propyl group.
De terapeutiske egenskaper til disse estrene med formel I The therapeutic properties of these esters of formula I
er illustrert ved eksperimentelle resultater som er gitt nedenfor. is illustrated by experimental results given below.
Dose-reaksjonsforholdet til digoxin og 4'-monobutyrylcymarin ble undersøkt i et hjerte-lungepreparat hos marsvin. Den maksimale effektive dose for begge glykosider var 50 ug (for 200 ml sirku-lerende væske). Digoxin bevirket ca. 85 - 90 % gjenopprettelse av hjerteutløp i forhold til utløpet før hjertesvikt, men i motsetning til dette forårsaket cymarinesteren ca. 110 % rekonvalesens. Denne maksimale effekt ble for digoxin opprettholdt i 25 minutter, og for cymarinesteren i 40 minutter. The dose-response relationship of digoxin and 4'-monobutyrylcymarin was investigated in a heart-lung preparation in guinea pigs. The maximum effective dose for both glycosides was 50 µg (for 200 ml of circulating fluid). Digoxin caused approx. 85 - 90% recovery of cardiac output compared to the output before heart failure, but in contrast the cymarin ester caused approx. 110% recovery. This maximum effect was maintained for digoxin for 25 minutes, and for the cymarin ester for 40 minutes.
De toksiske virkninger av digoxin målt som en stigning i The toxic effects of digoxin measured as a rise in
det høyre venøse trykk, oppsto 30 minutter etter doseinngivning og med cymarinesteren etter 52 minutter. Disse resultater antyder at 4'-monobutyrylcymarin er mer effektiv enn digoxin. the right venous pressure, occurred 30 minutes after dosing and with the cymarin ester after 52 minutes. These results suggest that 4'-monobutyrylcymarin is more effective than digoxin.
Det kan feks. brukes en cymarinester med formel I, i tilfeller for kongestiv hjertefeil, atrial fibrillasjon, atrial hjerte-bank, og paroksysmal tachycardia. I likhet med det som vanligvis er tilfelle med terapeutisk nyttige hjerteglykosider, er det best å gi estrene med formel I gjennom munnen unntatt i uvanlige omstendigheter.■ Den egnede dose vil naturligvis avhenge av symptomenes natur og al-vorlighet, og vil avhenge av legens skjønn. It can e.g. A cymarin ester of formula I is used in cases of congestive heart failure, atrial fibrillation, atrial palpitations, and paroxysmal tachycardia. As is usually the case with therapeutically useful cardiac glycosides, the esters of formula I are best given orally except in unusual circumstances.■ The appropriate dose will, of course, depend on the nature and severity of the symptoms and will depend on the discretion of the physician .
Estrene med formel (I) kan fremstilles ved forestring av cymarin med et hvilket som helst egnet acyleringsmiddel, f.eks. syre-anhydridet eller syrekloridet. På grunn av at acylgruppene i den fremstilte ester lett fraspaltes under sterkt sure eller sterkt al-kaliske betingelser, utføres reaksjonen fortrinnsvis i oppløsning i en organisk base slik som pyridin eller dimetylformamid mellom ca. The esters of formula (I) can be prepared by esterification of cymarin with any suitable acylating agent, e.g. the acid anhydride or the acid chloride. Because the acyl groups in the produced ester are easily split off under strongly acidic or strongly alkaline conditions, the reaction is preferably carried out in solution in an organic base such as pyridine or dimethylformamide between approx.
10° og 45°C, men fortrinnsvis ved romtemperatur. Når det anvendes et syre-anhydrid som acyleringsmiddel, kan den organiske basen erstattes som oppløsningsmiddel med en oppløsning av et metallisk salt av den tilsvarende syre i anhydridet. 10° and 45°C, but preferably at room temperature. When an acid anhydride is used as acylating agent, the organic base can be replaced as solvent with a solution of a metallic salt of the corresponding acid in the anhydride.
De ovenfor definerte forbindelser med formel (I) fremstilles således ifølge foreliggende fremgangsmåte ved acylering av cymarin med et acyleringsmiddel med formel R.CO.X, hvori X er et proton-aksepterende radikal, og R har den ovenfor angitte betydning. The above-defined compounds of formula (I) are thus prepared according to the present method by acylating cymarin with an acylating agent of formula R.CO.X, in which X is a proton-accepting radical, and R has the above meaning.
Følgende eksempler illustrerer oppfinnelsen. Rf-verdiene ble oppnådd, hvis ikke annet er angitt, i et kromat^ografisk system bestående av et oppløsningsmiddel av xylol/butanon (1/1:v/v) mettet med formamid og Whatman-papir nr. 1 impregnert med 25 % (v/v) formamid i aceton. I dette kromatografiske system har cymarin Rf 0.6. The following examples illustrate the invention. The Rf values were obtained, unless otherwise stated, in a chromatographic system consisting of a solvent of xylol/butanone (1/1:v/v) saturated with formamide and Whatman No. 1 paper impregnated with 25% ( v/v) formamide in acetone. In this chromatographic system, cymarin has an Rf of 0.6.
Eksempel 1 Example 1
Cymarin (10 g) ble oppløst i pyridin (66 ml) og propionsyre-anhydrid (60 ml) ble tilsatt. Etter å ha stått ved omgivelsestempera-tur i nærvær av nitrogen i to timer, ble blandingen heilt på knust is, det faste stoffet ble frafiltrert, vasket med vann og omkrystallisert fra vandig metanol. Det ble oppnådd krystaller av 33-4'-0-propionyl-3-D-cymarocyloksy-5,l4-dihydroksy-19-okso-53-card-20(22)-enolid Cymarin (10 g) was dissolved in pyridine (66 ml) and propionic anhydride (60 ml) was added. After standing at ambient temperature in the presence of nitrogen for two hours, the mixture was poured onto crushed ice, the solid was filtered off, washed with water and recrystallized from aqueous methanol. Crystals of 33-4'-0-propionyl-3-D-cymarocyloxy-5,14-dihydroxy-19-oxo-53-card-20(22)-enolide were obtained
(synonym: 4'-monopropionylcymarin), som smeltet ved 156°C, Rf 0.87, [a]p<3> = +49.8° (c = 1.0 i metanol). (synonym: 4'-monopropionylcymarin), which melted at 156°C, Rf 0.87, [a]p<3> = +49.8° (c = 1.0 in methanol).
Eksempel 2 Example 2
På samme måte som beskrevet i eksempel 1, ble cymarin acy-lert med smørsyre-anhydrid for således å gi 33-4'-O-butyryl-g-D-cymarocyloksy-S ,l4-dihydroksy-19-okso-53-cård-20 (22 )-enolid (synonym: 4'-monobutyrylcymarin), smeltepunkt 155°C, Rf 0.91, ta]jp = +51.5° In the same manner as described in Example 1, cymarin was acylated with butyric anhydride to thus give 33-4'-O-butyryl-g-D-cymarocyloxy-S,14-dihydroxy-19-oxo-53-cardo-20 (22 )-enolide (synonym: 4'-monobutyrylcymarin), melting point 155°C, Rf 0.91, ta]jp = +51.5°
(c = 1 i metanol). (c = 1 in methanol).
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8603814A SE464125B (en) | 1986-09-12 | 1986-09-12 | SYSTEM FOR FLUIDIZATION OF BULK MATERIAL |
| PCT/SE1987/000407 WO1988001963A1 (en) | 1986-09-12 | 1987-09-10 | System for fluidising bulk material |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| NO882031D0 NO882031D0 (en) | 1988-05-10 |
| NO882031L NO882031L (en) | 1988-05-13 |
| NO164969B true NO164969B (en) | 1990-08-27 |
| NO164969C NO164969C (en) | 1990-12-12 |
Family
ID=20365555
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO882031A NO164969C (en) | 1986-09-12 | 1988-05-10 | BULK MATERIAL FLUIDIZATION SYSTEM. |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0335864B1 (en) |
| JP (1) | JP2708164B2 (en) |
| DE (1) | DE3782946D1 (en) |
| HK (1) | HK68993A (en) |
| NO (1) | NO164969C (en) |
| SE (1) | SE464125B (en) |
| SG (1) | SG54293G (en) |
| WO (1) | WO1988001963A1 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2219784B (en) * | 1988-05-27 | 1992-09-30 | Gary Kenneth Busch | Element for adapting a bulk transport container or hold of a ship to fluidise and discharge its contents and method therefor |
| GB2227482A (en) * | 1989-01-26 | 1990-08-01 | Exprocad Services Ltd | Fluidising bulk particulate material |
| US8312818B2 (en) * | 2006-05-12 | 2012-11-20 | Jean-Claude Poncet | Modular vibratory floor |
| SG169253A1 (en) * | 2009-09-03 | 2011-03-30 | Viking Dredging As | A method of preparing a dry bulk carrier |
| BE1029471B1 (en) * | 2021-05-27 | 2023-01-09 | Gitra Bv | Bottom element for forming a fluidization bottom |
| WO2022249143A1 (en) * | 2021-05-27 | 2022-12-01 | Gitra Bv | Bottom element for forming a fluidization bottom |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3367723A (en) * | 1966-04-07 | 1968-02-06 | Halliburton Co | Steady flow bin for pulverulent material |
-
1986
- 1986-09-12 SE SE8603814A patent/SE464125B/en not_active IP Right Cessation
-
1987
- 1987-09-10 WO PCT/SE1987/000407 patent/WO1988001963A1/en active IP Right Grant
- 1987-09-10 EP EP87906027A patent/EP0335864B1/en not_active Expired - Lifetime
- 1987-09-10 JP JP62505394A patent/JP2708164B2/en not_active Expired - Lifetime
- 1987-09-10 DE DE8787906027T patent/DE3782946D1/en not_active Expired - Lifetime
-
1988
- 1988-05-10 NO NO882031A patent/NO164969C/en unknown
-
1993
- 1993-04-28 SG SG54293A patent/SG54293G/en unknown
- 1993-07-15 HK HK689/93A patent/HK68993A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO1988001963A1 (en) | 1988-03-24 |
| SE8603814D0 (en) | 1986-09-12 |
| SG54293G (en) | 1993-07-09 |
| EP0335864A1 (en) | 1989-10-11 |
| EP0335864B1 (en) | 1992-12-02 |
| NO164969C (en) | 1990-12-12 |
| NO882031L (en) | 1988-05-13 |
| HK68993A (en) | 1993-07-23 |
| SE464125B (en) | 1991-03-11 |
| JP2708164B2 (en) | 1998-02-04 |
| JPH02500585A (en) | 1990-03-01 |
| SE8603814L (en) | 1988-03-13 |
| DE3782946D1 (en) | 1993-01-14 |
| NO882031D0 (en) | 1988-05-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| IL104089A (en) | Glycosylated steroid derivatives for transport across biological membranes pharmaceutical compositions containing them and process for making same | |
| NO168302B (en) | PROCEDURE FOR PREPARING CRYSTAL FORM (B) OF 2-ETHOXY-4- (N- (1- (2-PIPERIDINO-PHENYL) -3-METHYL-1-BUTYL) -AMINOCARBONYLMETHYL) -BENZOIC ACID | |
| FI89055B (en) | FOERFARANDE FOER FRAMSTAELLNING AV NYA ANDROSTAN-17-KARBOXYLSYRAESTRAR | |
| NO144178B (en) | UNDERWATER BRIDGE HEAD. | |
| NO164969B (en) | BULK MATERIAL FLUIDIZATION SYSTEM. | |
| DE3852579T2 (en) | Castanospermine esters and glycosides. | |
| US3223587A (en) | Cardiac active acyl cymarols | |
| NO135789B (en) | ||
| NO157864B (en) | ANALOGY PROCEDURE FOR THE PREPARATION OF NEW THERAPEUTICALLY EFFECTIVE DICHLORATED 16ALFA METHYL PREPARATION DERIVATIVES. | |
| RU2153503C2 (en) | Oligosaccharide-containing 14-aminosteroids, method of their synthesis, pharmaceutical composition, method of treatment, method of amino-group incorporation | |
| DEFERRARI et al. | Reaction of Ammonia with Some Acetylated and Benzoylated Monosaccharides. VI. Derivatives of L-Arabinose, D-Xylose, and D-Ribose | |
| JPH09502984A (en) | Novel urethane-containing aminosteroid compound | |
| US3812097A (en) | Yranuronosyl)oxy)olean-12-en-30-oic acid | |
| US3758524A (en) | Process for the manufacture of 21-fluorosteroids | |
| DE60106246T2 (en) | MALTO OLIGOSACCHARIDES AND ITS USE | |
| DE69519053T2 (en) | 7-glycosyloxybenzopyran derivative and antiallergic agent containing it | |
| EP0523499B1 (en) | Acetohydroxamic acid compound, medicaments containing it and method for the preparation of this compound and the medicaments | |
| US4515786A (en) | 11α-Amino-androstanes | |
| CH673280A5 (en) | ||
| US6291434B1 (en) | Benzylmaltotriosides as inhibitors of smooth muscle cell proliferation | |
| US2959584A (en) | 4-hydroxyprogesterone and intermediate therefor | |
| NO156624B (en) | PROCEDURE FOR AUTOMATICALLY FEEDING WASTE TO A COMBUSTION OVEN. | |
| NO125975B (en) | ||
| Horner et al. | Selective benzoylation of methyl 2-benzamido-2-deoxy-α-D-glucopyranoside: a convenient preparation of derivatives of 2-amino-2-deoxy-D-galactose | |
| US3741955A (en) | 3beta-hydroxy - 14,15beta-oxido - 14beta-bufa-4,20,22-trienalide-3beta-(alpha-l-rhamnopyranoside) |