DK141116B - Analogifremgangsmåde til fremstilling af en di-(2-acetoxybenzoyl)-ester af 1,8,9-trihydroxyanthracen eller en 9-anthrontautomer deraf. - Google Patents
Analogifremgangsmåde til fremstilling af en di-(2-acetoxybenzoyl)-ester af 1,8,9-trihydroxyanthracen eller en 9-anthrontautomer deraf. Download PDFInfo
- Publication number
- DK141116B DK141116B DK587672AA DK587672A DK141116B DK 141116 B DK141116 B DK 141116B DK 587672A A DK587672A A DK 587672AA DK 587672 A DK587672 A DK 587672A DK 141116 B DK141116 B DK 141116B
- Authority
- DK
- Denmark
- Prior art keywords
- trihydroxyanthracene
- preparation
- acetoxybenzoyl
- ester
- anthronutomer
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title description 8
- YUTJCNNFTOIOGT-UHFFFAOYSA-N anthracene-1,8,9-triol Chemical compound C1=CC(O)=C2C(O)=C3C(O)=CC=CC3=CC2=C1 YUTJCNNFTOIOGT-UHFFFAOYSA-N 0.000 title description 6
- 238000000034 method Methods 0.000 title description 6
- 238000002360 preparation method Methods 0.000 title description 6
- -1 2-acetoxybenzoyl Chemical group 0.000 title description 2
- 230000003902 lesion Effects 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 208000003251 Pruritus Diseases 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229960002311 dithranol Drugs 0.000 description 4
- 230000007794 irritation Effects 0.000 description 4
- 230000007803 itching Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 206010015946 Eye irritation Diseases 0.000 description 3
- 201000004681 Psoriasis Diseases 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- NUZWLKWWNNJHPT-UHFFFAOYSA-N anthralin Chemical class C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O NUZWLKWWNNJHPT-UHFFFAOYSA-N 0.000 description 3
- 231100000013 eye irritation Toxicity 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- DSGKWFGEUBCEIE-UHFFFAOYSA-N (2-carbonochloridoylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1C(Cl)=O DSGKWFGEUBCEIE-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 238000004299 exfoliation Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 150000005691 triesters Chemical class 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 208000033856 Chemical eye injury Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000364057 Peoria Species 0.000 description 1
- 206010037888 Rash pustular Diseases 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 206010023332 keratitis Diseases 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 208000029561 pustule Diseases 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/78—Benzoic acid esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/88—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/92—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with etherified hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
(¾^ (11) FREMUE66El$ESSKIIIFT 1 Μ 1 1 6 DANMARK (61) int. Cl.3 C 07 C 69/90 §(21) Antegning nr. 5876/72 (22) Indleveret den 24. nOV.
(23) Lebedag 24. nOV. 1972 (44) Ansøgningen fremtogt og framlmgBetooMkrtftBt otfam8gg)ort dan 21 . j&n. 1980
Dl REKTORATET FOR
PATENT-OG VAREMÆRKEVÆSENET (30) Prtorttet begæret fra dan
26. nov. 1971, 54927/71, GB
(71) STERWIN AG, Zeughausgasse 9, Zug, CH.
(72) Opfinder? Andrew Robertson, 7 Aisgill Drive, West Denton, Newcastle-upon-Tyne, GB.
(74) Fuldm»gtig under tagene behandling:
Patentagentfirmaet Magnus Jensens Eftf.
(M) Analogifremgangsmåde til fremstilling af en di-(2-acetoxybenzoyl)-ester af 1,8,9-trlhydroxyanthracen eller en 9-anthrontautomer deraf.
Opfindelsen angår en analogifreagangsaåde til fremstilling af en di-(2-acetoxybenaoyl)-ester af 1,8,9-trihydroxyanthracen eller en 9-anthrontautomer deraf, og denne fremgangsmåde er ejendommelig ved det i kravets kendetegnende del anførte· Det benyttede funktionelle derivat kan være syreehloridet, og katalysatoren pyridin. 1,8,9-trlaoetoxyanthraoen ér kendt til behandling af peoriaeis· Imidlertid er det velkendt, at stoffet har alvorlige bivirkninger, eoa gør det uegnet til brug af patienter uden nøje medioinek overvågning. Den alvorligste ulempe er, at det er skadeligt for øjnene, idet det fremkalder akut keratitis eller kemisk conjunctivitis. Dette er f.eks. beskrevet i The Lancet, 1967, II, side 195 og side 311.
Den ved fremgangsmåden ifølge opfindelsen fremstillede 2 tAl116 forbindelse har ikke det usubstituerede dithranols ulemper, idet den ikke svider og ikke pletter, og den har heller ikke triacetozyderivatets ulemper. Sen indeholder ikke en hydrolyserbar acetylgruppe, og den har ikke vist sig at fremkalde nogen væsentlig irritation i kontakt med øjet, jvfr. de ne-, denfor anførte forsøgsresultater.
Behandling af psoriasislasioner under anvendelse af di-2-acetoxy-benzovldithranol.
Ti exteme patienter med psoriasis læsioner påførte daglig de pågældende hudområder di-2-acetoxybenzoyldithranol i en periode på 1-8 uger. Patienterne blev undersøgt hver uge, og følgende resultater foreligger nus
Vurderingen af patienternes tilstand skete ved en undersøgelse af følgende kriterier: induration rødme afskalning kløe hudløshed og pusteler
Efter 2 ugers behandling viste patienterne betydelig bedring, og navnlig iagttoges følgende fremskridt: induration: 75^'s forbedring rødme: 50#’s forbedring afskalning: 50#'s forbedring kløe: 25#'s forbedring
Ved f.eks. 7596 * s forbedring menes, at 6 ud af 8 undersøgte patienter har en bedring i det pågældende kriterium.
Efter 6 ugers forløb foreligger der kun resultater fra 1 patient, som udviste betydelig forbedring med hensyn til induration og rødme, som han hidtil havde lidt af som følge af sin psoriasis.
Der udførtes et yderligere forsøg under anvendelse af det samme aktive stof på 3 mandlige patienter. De samme kriterier blev undersøgt, og tykkelsen af læsionerne blev også målt.
I tilfælde nr. 1 led patienten til at begynde med af let afskalning og moderat induration og rødme. Tykkelsen af læsionerne vurderedes til 2 (moderat hævet). Efter 3 ugers behandling med di-2-acetoxybenzoyldithranol var der en betydelig forbedring. En let afskalning forekom stadig, men indurationen og rødmen var aftaget, og tykkelsen af læsionerne vurderedes til kun 1 (svag hæv- 141116 3 ning). Der forekom ingen irritation eller pietning, og der noteredes ingen irritation af øjnene.
I tilfælde nr. 2 led patienten til at begynde med af læsioner, som blev vurderet til 3 (udtalt hævning), med kraftig induration, rødme og afskalning og moderat kløe* Efter behandling i 1 måned med di-2-acetoxybenzoyldithranol iagttoges der en betydelig forbedring, læsionerne havde aftaget i tykkelse til grad 1, og der var kun svag induration, rødme, afskalning og kløe· ler iagttoges ikke nogen pietning og kun ringe irritation· ler blev ikke noteret nogen irritation af øjnene« I tilfælde nr, 3 led patienten af læsioner vurderet til 2 i bedømmelsesekalaen, ledsaget af moderat induration, rødme og afskalning. Efter 3 ugere behandling med di-2-acetoiybenzoyl-dithranol var der en betydelig forbedring, læsionerne blev da vurderet til 0 (niveauet for den omgivende hud), og der var ikke nogen induration eller afskalning og kun svag rødme· ler var ikke nogen pletning eller irritation og heller ingen øjenirritation.
ledenstående eksempel illustrerer fremgangsmåden Ifølge opfindelsen· 141116 4
Eksempel,
Fremstilling af mono- og di-(2-aeetoxy-benzoyl)-esterne af 1,8.9--trih.vdrox.vanthracen og separation af diesteren.
1) Fremstilling af en blanding af esterne.
1,8,9-trihydroxyanthracen (6 g), xylen (60 g) og pyridin (5 g) omrøres under nitrogenatmosfære i 10 minutter ved 60°C. 2--acetoxy-benzoylchlorid (10,5 g, 2 mol ækvivalenter) tilsættes dråbevis i løbet af 5 minutter, og efter yderligere 10 minutters forløb standses opvarmningen. Der tilsættes aktivkul og diatoméjord, og omrøringen fortsættes i 10 minutter. Blandingen filtreres gennem diatomljord, og filtratet sættes dråbevis til petroleumsether under omrøring (kp. 40-60°C, 750 ml). Produktet isoleres som et bleggrønt amorft stof (4 g).
Undersøgelse af produktet ved tyndtlagsehromatografi viser tilstedeværelsen af kun en lille mængde frit 1,8,9-trihydroxyanthra-een. Pletter, som angiver tilstedeværelsen af lavmolekylære estere, iagttages foruden pletterne svarende til triesteren.
Der udføres en lignende fremstilling under anvendelse af kun 1 mol ækvivalent 2-acetoxy-benzoylehlorid og pyridin for hver ækvivalent 1,8,9-trihydroxyanthracen. I dette tilfælde fås et gulbrunt produkt, som viser sig at indeholde en forholdsvis stor mængde frit 1,8,9-trihydroxyanthracen, og det anses for at være mindre egnet til yderligere adskillelse end det ovenfor beskrevne produkt.
2) Adskillelse af esterne ved tørsø.ilechromatografi.
Adskillelsen udføres på 1 g materiale, som opløses i chloroform (50 ml) og sættes til silieagel af kvalitet til tørsøjlechroma-tografi (15 g), og opløsningsmidlet fordampes under formindsket tryk. Den fremkomne dispersion af blandede estere på silieagel anbringes på en tør søjle (3 x 50 cm) og elueres med toluen.
De fremkomne syv klart adskilte bånd adskilles fysisk, elueres med chloroform gennem sintret glas, og de fremkomne opløsninger undersøges ved tyndtlagsehromatografi, idet de nummereres 1-7 i aftagende orden af -værdier.
Prøverne nr. 5, 6 og 7 er de største prøver, og disse inddampes til tørhed. De faste produkter fra disse prøver, som muligvis ikke er helt rene, undersøges ved massespektrometri og viser sig at være henholdsvis monoesteren, diesteren og triesteren. De relevante data er: 5 U1116 m/e m/e
Prøve ester beregnet fundet 5 mono- 388 388 (med en fraktion ved 550) 6 di- 550 550 7 tri- 712 712 (med en fraktion ved 550 og mindre ved 388)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5492771 | 1971-11-26 | ||
| GB5492771A GB1361879A (en) | 1971-11-26 | 1971-11-26 | Benzoyl esters of 1,8,9-trihydroxy-anthracene processes for their preparation and compositions incorporating them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK141116B true DK141116B (da) | 1980-01-21 |
| DK141116C DK141116C (da) | 1980-06-30 |
Family
ID=10472486
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK587672AA DK141116B (da) | 1971-11-26 | 1972-11-24 | Analogifremgangsmåde til fremstilling af en di-(2-acetoxybenzoyl)-ester af 1,8,9-trihydroxyanthracen eller en 9-anthrontautomer deraf. |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS5531766B2 (da) |
| BE (1) | BE791643A (da) |
| CA (1) | CA996134A (da) |
| CH (1) | CH584181A5 (da) |
| CS (1) | CS161968B2 (da) |
| DK (1) | DK141116B (da) |
| FI (1) | FI56371C (da) |
| FR (1) | FR2161058B1 (da) |
| GB (1) | GB1361879A (da) |
| HU (1) | HU167374B (da) |
| IE (1) | IE37193B1 (da) |
| NL (1) | NL7215802A (da) |
| PL (1) | PL89681B1 (da) |
| SE (2) | SE400548B (da) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2426971A1 (fr) * | 1978-05-26 | 1979-12-21 | Peugeot | Dispositif contacteur electrique associe a un levier de commande |
| US4843097A (en) * | 1984-06-13 | 1989-06-27 | Groupement D'interet Economique Dit: Centre International De Recherches Dermatologiques C.I.R.D. | 10-aryl-1,8-dihydroxy-9-anthrones and their esters, process for preparing same, and use of same in human and veterinary medicine and in cosmetics |
| FR2591222B1 (fr) * | 1985-12-11 | 1988-07-22 | Cird | Mono, di et tri-esters de dihydroxy-1,8 phenyl-10 anthrone-9 ou anthranol-9, leur procede de preparation et leur utilisation en medecine humaine ou veterinaire et en cosmetique |
| JP6255210B2 (ja) * | 2013-10-24 | 2017-12-27 | アーゼッド・エレクトロニック・マテリアルズ（ルクセンブルグ）ソシエテ・ア・レスポンサビリテ・リミテ | レジスト下層膜形成組成物 |
-
0
- BE BE791643D patent/BE791643A/xx not_active IP Right Cessation
-
1971
- 1971-11-26 GB GB5492771A patent/GB1361879A/en not_active Expired
-
1972
- 1972-11-22 NL NL7215802A patent/NL7215802A/xx not_active Application Discontinuation
- 1972-11-23 PL PL1972159046A patent/PL89681B1/pl unknown
- 1972-11-23 CS CS7976A patent/CS161968B2/cs unknown
- 1972-11-23 IE IE1633/72A patent/IE37193B1/xx unknown
- 1972-11-24 FI FI3329/72A patent/FI56371C/fi active
- 1972-11-24 CH CH1713572A patent/CH584181A5/xx not_active IP Right Cessation
- 1972-11-24 SE SE7215395A patent/SE400548B/xx unknown
- 1972-11-24 DK DK587672AA patent/DK141116B/da not_active IP Right Cessation
- 1972-11-24 HU HUSE1652A patent/HU167374B/hu unknown
- 1972-11-24 FR FR7241854A patent/FR2161058B1/fr not_active Expired
- 1972-11-24 CA CA157,483A patent/CA996134A/en not_active Expired
- 1972-11-27 JP JP11816272A patent/JPS5531766B2/ja not_active Expired
-
1976
- 1976-05-11 SE SE7605364A patent/SE7605364L/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE791643A (fr) | 1973-03-16 |
| FR2161058B1 (da) | 1976-04-23 |
| CS161968B2 (da) | 1975-06-10 |
| JPS4862749A (da) | 1973-09-01 |
| JPS5531766B2 (da) | 1980-08-20 |
| PL89681B1 (da) | 1976-12-31 |
| GB1361879A (en) | 1974-07-30 |
| DK141116C (da) | 1980-06-30 |
| NL7215802A (da) | 1973-05-29 |
| FI56371C (fi) | 1980-01-10 |
| IE37193L (en) | 1973-05-26 |
| CH584181A5 (da) | 1977-01-31 |
| DE2257442B2 (de) | 1977-03-10 |
| IE37193B1 (en) | 1977-05-25 |
| DE2257442A1 (de) | 1973-05-30 |
| SE7605364L (sv) | 1976-05-11 |
| CA996134A (en) | 1976-08-31 |
| SE400548B (sv) | 1978-04-03 |
| FI56371B (fi) | 1979-09-28 |
| HU167374B (da) | 1975-09-27 |
| FR2161058A1 (da) | 1973-07-06 |
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| DK141116B (da) | Analogifremgangsmåde til fremstilling af en di-(2-acetoxybenzoyl)-ester af 1,8,9-trihydroxyanthracen eller en 9-anthrontautomer deraf. | |
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