DK141116B - Analogous process for the preparation of a di- (2-acetoxybenzoyl) ester of 1,8,9-trihydroxyanthracene or a 9-anthronutomer thereof. - Google Patents

Analogous process for the preparation of a di- (2-acetoxybenzoyl) ester of 1,8,9-trihydroxyanthracene or a 9-anthronutomer thereof. Download PDF

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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
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trihydroxyanthracene
preparation
acetoxybenzoyl
ester
anthronutomer
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DK587672AA
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Danish (da)
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DK141116C (en
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Andrew Robertson
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Sterwin Ag
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    • 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

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  • 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.(¾ ^ (11) FREMUE66El $ ESSKIIIFT 1 Μ 1 1 6 DENMARK (61) Int. Cl.3 C 07 C 69/90 § (21) Note 5858/72 (22) Filed on Nov. 24.

(23) Lebedag 24. nOV. 1972 (44) Ansøgningen fremtogt og framlmgBetooMkrtftBt otfam8gg)ort dan 21 . j&n. 1980(23) Live day 24. nov. 1972 (44) The application was presented and presented BetaMcrtftBt otfam8gg) ort dan 21. j & n. 1980

Dl REKTORATET FORDl THE RECTORATE FOR

PATENT-OG VAREMÆRKEVÆSENET (30) Prtorttet begæret fra danPATENT AND TRADEMARKET (30) Prtorttet request from dan

26. nov. 1971, 54927/71, GBNov 26 1971, 54927/71, GB

(71) STERWIN AG, Zeughausgasse 9, Zug, CH.(71) STERWIN AG, Zeughausgasse 9, Zug, CH.

(72) Opfinder? Andrew Robertson, 7 Aisgill Drive, West Denton, Newcastle-upon-Tyne, GB.(72) Inventor? Andrew Robertson, 7 Aisgill Drive, West Denton, Newcastle-upon-Tyne, GB.

(74) Fuldm»gtig under tagene behandling:(74) Completely covered under the roofs:

Patentagentfirmaet Magnus Jensens Eftf.Patent law firm Magnus Jensens Eftf.

(M) Analogifremgangsmåde til fremstilling af en di-(2-acetoxybenzoyl)-ester af 1,8,9-trlhydroxyanthracen eller en 9-anthrontautomer deraf.(M) Analogous process for the preparation of a di- (2-acetoxybenzoyl) ester of 1,8,9-trihydroxyanthracene or a 9-anthronutomer thereof.

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.The invention relates to an analogous process for the preparation of a di- (2-acetoxybenaoyl) ester of 1,8,9-trihydroxyanthracene or a 9-anthronutomer thereof and this process is characterized by the characterizing part of the claim. be the acid chloride and the catalyst pyridine. The 1,8,9-triethoxyanthra is known for the treatment of peoria ice cream · However, it is well known that the drug has serious side effects, which makes it unsuitable for use by patients without careful mediocre monitoring. The most serious disadvantage is that it is harmful to the eyes as it causes acute keratitis or chemical conjunctivitis. This is e.g. described in The Lancet, 1967, II, page 195 and page 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.The 2 tAl116 compound prepared by the process of the invention does not have the disadvantages of the unsubstituted dithranol in that it does not stain and does not stain, nor does it have the disadvantages of the triacetozide derivative. Sen does not contain a hydrolyzable acetyl group, and it has not been shown to cause any significant irritation to the eye, cf. the following test results.

Behandling af psoriasislasioner under anvendelse af di-2-acetoxy-benzovldithranol.Treatment of psoriasis lesions using 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 nusTen extreme patients with psoriasis lesions daily applied the affected skin areas di-2-acetoxybenzoyldithranol for a period of 1-8 weeks. The patients were examined weekly and the following results are available

Vurderingen af patienternes tilstand skete ved en undersøgelse af følgende kriterier: induration rødme afskalning kløe hudløshed og pustelerThe assessment of patients' condition was done by examining the following criteria: induration flushing peel itching skinlessness and pustules

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 forbedringAfter 2 weeks of treatment, patients showed significant improvement, and in particular, the following progress was observed: induration: 75 ^ improvement redness: 50 # improvement peeling: 50 # improvement itching: 25 # improvement

Ved f.eks. 7596 * s forbedring menes, at 6 ud af 8 undersøgte patienter har en bedring i det pågældende kriterium.For example, 7596 * s improvement is believed that 6 out of 8 patients studied have an improvement in that criterion.

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.After 6 weeks, there were only results from 1 patient who showed significant improvement in induration and redness, which he had so far suffered from as a result of his 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.A further experiment was performed using the same active substance in 3 male patients. The same criteria were investigated and the thickness of the lesions was also measured.

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.In case # 1, the patient initially suffered from mild peeling and moderate induration and redness. The thickness of the lesions was assessed at 2 (moderately elevated). After 3 weeks of treatment with di-2-acetoxybenzoyl dithranol, there was a significant improvement. Slight peeling still occurred, but induration and redness had subsided, and the thickness of the lesions was assessed to only 1 (slight elevation). There was no irritation or tingling, and no eye irritation was noted.

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.In case # 2, the patient initially suffered from lesions assessed at 3 (pronounced swelling), with vigorous induration, redness and exfoliation and moderate itching * After 1 month of treatment with di-2-acetoxybenzoyl dithranol, significant improvement, the lesions had decreased in thickness to grade 1, and there was only slight induration, redness, peeling and itching · clay was not observed pitting and only slight irritation · clay was not noted eye irritation 'In case # 3, the patient suffered of lesions rated at 2 in the rating scale, accompanied by moderate induration, redness, and peeling. After 3 weeks of treatment with di-2-acetoiybenzoyl-dithranol, there was a significant improvement, the lesions were then assessed at 0 (the level of the surrounding skin), and there was no induration or exfoliation and only slight redness was no stain or irritation and no eye irritation either.

ledenstående eksempel illustrerer fremgangsmåden Ifølge opfindelsen· 141116 4The following example illustrates the method of the invention

Eksempel,Example,

Fremstilling af mono- og di-(2-aeetoxy-benzoyl)-esterne af 1,8.9--trih.vdrox.vanthracen og separation af diesteren.Preparation of the mono- and di- (2-aethoxy-benzoyl) esters of 1,8,9-trihydroxypyrthracene and separation of the diester.

1) Fremstilling af en blanding af esterne.1) Preparation of a mixture of the esters.

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).1,8,9-trihydroxyanthracene (6 g), xylene (60 g) and pyridine (5 g) are stirred under nitrogen atmosphere for 10 minutes at 60 ° C. 2 - Acetoxybenzoyl chloride (10.5 g, 2 mole equivalents) is added dropwise over 5 minutes and after another 10 minutes heating is stopped. Activated charcoal and diatomaceous earth are added and stirring is continued for 10 minutes. The mixture is filtered through diatomaceous earth and the filtrate is added dropwise to petroleum ether with stirring (b.p. 40-60 ° C, 750 ml). The product is isolated as a pale green amorphous substance (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.Examination of the product by thin layer chromatography shows the presence of only a small amount of free 1,8,9-trihydroxyanthraene. Spots indicating the presence of low molecular weight esters are observed in addition to the spots corresponding to the triester.

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.A similar preparation is carried out using only 1 mole equivalent of 2-acetoxy-benzoyl chloride and pyridine for each equivalent of 1,8,9-trihydroxyanthracene. In this case, a tan product is obtained which is found to contain a relatively large amount of free 1,8,9-trihydroxyanthracene, and it is considered less suitable for further separation than the product described above.

2) Adskillelse af esterne ved tørsø.ilechromatografi.2) Separation of the esters by dry-oil chromatography.

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.The separation is carried out on 1 g of material which is dissolved in chloroform (50 ml) and added to silica gel of high quality for dry column chromatography (15 g) and the solvent is evaporated under reduced pressure. The resulting dispersion of mixed esters on silica gel is placed on a dry column (3 x 50 cm) and eluted with toluene.

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.The resulting seven clearly separated bands are physically separated, eluted with chloroform through sintered glass, and the solutions obtained are examined by thin layer chromatography, numbering 1-7 in decreasing order of values.

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/eSamples Nos 5, 6 and 7 are the largest samples and these are evaporated to dryness. The solid products from these samples, which may not be completely pure, are examined by mass spectrometry and found to be the monoester, diester and triester, respectively. The relevant data is: 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)Sample ester calculated found 5 mono- 388 388 (with a fraction at 550) 6 di- 550 550 7 tri- 712 712 (with a fraction at 550 and less at 388)

DK587672AA 1971-11-26 1972-11-24 Analogous process for the preparation of a di- (2-acetoxybenzoyl) ester of 1,8,9-trihydroxyanthracene or a 9-anthronutomer thereof. DK141116B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
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
GB5492771 1971-11-26

Publications (2)

Publication Number Publication Date
DK141116B true DK141116B (en) 1980-01-21
DK141116C DK141116C (en) 1980-06-30

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DK587672AA DK141116B (en) 1971-11-26 1972-11-24 Analogous process for the preparation of a di- (2-acetoxybenzoyl) ester of 1,8,9-trihydroxyanthracene or a 9-anthronutomer thereof.

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JP (1) JPS5531766B2 (en)
BE (1) BE791643A (en)
CA (1) CA996134A (en)
CH (1) CH584181A5 (en)
CS (1) CS161968B2 (en)
DK (1) DK141116B (en)
FI (1) FI56371C (en)
FR (1) FR2161058B1 (en)
GB (1) GB1361879A (en)
HU (1) HU167374B (en)
IE (1) IE37193B1 (en)
NL (1) NL7215802A (en)
PL (1) PL89681B1 (en)
SE (2) SE400548B (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2426971A1 (en) * 1978-05-26 1979-12-21 Peugeot Vehicle speed changing control lever - has flexible rod contact which closes with another electrical contact on lateral displacement of lever
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 (en) * 1985-12-11 1988-07-22 Cird MONO, DI AND TRI-ESTERS OF 1,8-DIHYDROXY PHENYL-10 ANTHRONE-9 OR ANTHRANOL-9, THEIR PREPARATION PROCESS AND THEIR USE IN HUMAN OR VETERINARY MEDICINE AND IN COSMETICS
JP6255210B2 (en) * 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 Resist underlayer film forming composition

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CH584181A5 (en) 1977-01-31
JPS5531766B2 (en) 1980-08-20
PL89681B1 (en) 1976-12-31
DE2257442B2 (en) 1977-03-10
DK141116C (en) 1980-06-30
HU167374B (en) 1975-09-27
CS161968B2 (en) 1975-06-10
SE7605364L (en) 1976-05-11
SE400548B (en) 1978-04-03
DE2257442A1 (en) 1973-05-30
JPS4862749A (en) 1973-09-01
FR2161058B1 (en) 1976-04-23
IE37193L (en) 1973-05-26
BE791643A (en) 1973-03-16
FI56371B (en) 1979-09-28
IE37193B1 (en) 1977-05-25
NL7215802A (en) 1973-05-29
FI56371C (en) 1980-01-10
FR2161058A1 (en) 1973-07-06
GB1361879A (en) 1974-07-30
CA996134A (en) 1976-08-31

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