GB1579862A - N-phenylacyl-2-hydroxyethylamines - Google Patents

N-phenylacyl-2-hydroxyethylamines Download PDF

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Publication number
GB1579862A
GB1579862A GB3668/79A GB366879A GB1579862A GB 1579862 A GB1579862 A GB 1579862A GB 3668/79 A GB3668/79 A GB 3668/79A GB 366879 A GB366879 A GB 366879A GB 1579862 A GB1579862 A GB 1579862A
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alkyl
halo
compound
formula
hydrogen
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GB3668/79A
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Wyeth Holdings LLC
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American Cyanamid Co
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Priority claimed from US05/739,924 external-priority patent/US4090025A/en
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB1579862A publication Critical patent/GB1579862A/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/70—One oxygen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/30—Oxygen or sulfur atoms
    • C07D233/32—One oxygen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/30—Oxygen or sulfur atoms
    • C07D233/32—One oxygen atom
    • C07D233/38—One oxygen atom with acyl radicals or hetero atoms directly attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/30—Oxygen or sulfur atoms
    • C07D233/42—Sulfur atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

PATENT SPECIFICATION
Application No 3668/79 ( 22) Filed 17 March 1977 Divided out of 1579861 Convention Application No 680311 Filed 26 April 1976 Convention Application No 739924 Filed 8 Nov 1976 in United States of America (US) Complete Specification published 26 Nov 1980
INT CL 3 C 07 C 97/10 ( 11) 1 579 862 ( 1 ( 52) Index at acceptance C 2 C 220 227 22 Y 30 Y 311 313 314 31 Y 322 32 Y 338 339 351 355 358 35 Y 360 361 364 366 368 36 Y 620 623 624 625 628 633 650 652 662 665 694 699 AA LM LZ ( 72) Inventors SIVARAMAN RAGHU ARTHUR KENTARO HOFFMANN and BALWANT SINGH ( 54) N-PHENYLACYL-2-HYDROXYETHYLAMINES ( 71) We, AMERICAN CYANAMID COMPANY, a Corporation organized and existing under the laws of the State of Maine, United States of America, of Berdan Avenue, Township of Wayne, State of New Jersey, United States of America, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement:-
This invention relates to novel secondary amines, which may, for example, be used as intermediates in the preparation of novel non-asymmetric tetramisoles, levamisoles and derivatives thereof described and claimed in our co-pending Parent Application No 11485/77 Serial No.
1,579,861, from which the present Application is divided, and to a method of preparing said novel secondary amines.
The compounds in accordance with the present invention are represented by the following general formula:
O 11 R 2-C-CH 2-NH-CH 2-CH 2-OR (I) wherein R is chosen from: hydrogen, alkyl C,-C 6, halo alkyl C,-C 6, phenyl optionally substituted with up to three groups consisting of alkyl C,-C 6, halo and alkoxy C,-C 6; or R is a moiety of the formula COR 3 wherein R 3 is hydrogen, alkyl C,-C 6, halo Cl-C 6 alkyl alkoxy C,-C 6, phenyl or phenoxy optionally substituted with up to four groups consisting of alkyl C,-C 6, halo, trifluoromethyl or alkoxy C 1 l-C'6; and R 2 is phenyl optionally substituted with up to two groups consisting of alkyl C,-C 6, alkoxy C,-C 6, halo or trifluoromethyl, with the proviso that R is not hydrogen when R 2 is unsubstituted phenyl.
Another aspect of the present invention provides a method for the preparation of the above defined compounds, comprising reacting an a-substituted ketone of the formula:
0 R 2-C-CH 2-X (II) in which R 2 is as defined above, and X is a group (e g chlorine, fluorine, bromine, iodine and p-toluene sulfonate) which can be displaced by a nucleophilic reagent, with an amine, of the formula:
H 2 N-CH 2-CH 2-OR (III) wherein R is as defined above, or its acid addition salt, in an excess of said amine, or in the presence of a tertiary amine, or in the presence of a hydroxide source (e g sodium carbonate), at a temperature from O C to C, for at least 30 minutes The reaction is generally carried out in a solvent such as an alcohol or halocarbon Reaction time may be from 30 minutes up to 3 hours.
The compounds of Formula I may then be further reacted as described in our copending Application Nos 10270/77 and 11485/77 serial no 1,579,861 to form imidazolinones.
Yet another aspect of the invention provides a method for the preparation of compounds of Formula I, which comprises reacting a compound of the formula:
( 21) ( 62) ( 31) ( 32) ( 31) ( 32) ( 33) ( 44) ( 51) 1,579,862 R 2 COCH 2 X wherein R 2 and X are as defined abov, with a compound of the formula:
R 3 l wherein R 3 is as defined above, at temperature of 25 C to 65 C in a suitabl solvent (e g chloroform) Thus th compound of formula I wherein R is an ac.
group may be made by a procedur represented in the following flow diagrar R 2 COCH 2 X + N R 3 Y 250-650 C solvent e g chloroform Xe R 2 CO-CH 2 R 3 (H 2 a a a II II R 2 CH NHCH 2 CH 20 H 2 OCR 3 One group of compounds within tl scope of this invention are those Formula I above wherein R is chosen fro hydrogen, C,-C 6 alkyl, halo C 1-C 6 alk) or phenyl optionally substituted with or halogen atom or R is the moiety COR 3 which R 3 is chosen from hydrogen, C,-( alkyl, halo C,-C 6 alkyl, and phen optionally substituted with one haloge atom; and R 2 is chosen fro trifluorophenylmethyl and phen.
optionally substituted with one or tm halogen atoms, with the proviso that R not hydrogen when R 2 is unsubstitute phenyl.
Preferred embodiments of the prese invention are compounds of the abo formula I, wherein R is selected fro hydrogen, C,-C 6 alkyl, phenyl, and C Ol wherein R 3 is selected from hydroge C,-C 6 alkyl and phenyl; and R 2 is select( from phenyl and m-halophenyl but is halophenyl when R is hydrogen Mo preferred embodiments of the presei invention are compounds of the formula wherein R is selected from C C 4 alk 3 phenyl and COR 3 wherein R 3 is selected from hydrogen, C,-C 6 alkyl and phenyl; e, and R 2 is phenyl The invention is illustrated in the following Examples in which Examples I to 7 describe the preparation of compounds in accordance with the invention, as intermediaries in the course of preparation of substituted imidazolines which form the subject of the a parent Application.
a e EXAMPLE I le 1 -( 2 M ethoxyethyl)-4-phenyl-4Yl imidazolin-2-one e Phenacyl bromide ( 60 g), in 200 ml of I methylene chloride, is added over one hour to 2-methoxyethylamine ( 52 g), in 100 ml.
of methylene chloride, and cooled with an ice bath The mixture is stirred for two hours at O C Water ( 400 ml) is added and the organic layer is separated, dried over anhydrous sodium sulfate and concentrated under aspirator vacuum (at room temperature) The viscous oil ( 260 g), identified by infrared and proton magnetic spectroscopy as N (phenacyl) 2 methoxyethylamine, is dissolved in methanol ( 200 ml), cooled to O C and acetic acid ( 80 ml) and potassium cyanate ( 30 g) is added The mixture is refluxed for minutes, the solvent removed under reduced pressure and the residue is taken up in 600 ml of chloroform and washed with saturated sodium bicarbonate solution The chloroform layer is washed, dried over sodium sulfate and concentrated to give a semisolid Trituration with ether and filtration yields the title product as a yellow crystal; m p 152 -153 C.
he of.
m EXAMPLE 2 yl, 1-( 2-methoxyethyl)-4-phenyl-4ne imidazolin-2-one in Phenacyl bromide ( 199 g), in 400 ml of C 6 chloroform, is added over one half hour to yl a mixture of 2 methoxyethylamine ( 82 g) en and triethylamine ( 152 g) in 200 ml of m chloroform at O C The mixture is stirred yl for two hours at O -10 C Water ( 400 ml) vo is added and the organic layer is separated is and washed with another 400 ml of water.
ed The chloroform layer, containing N (phenacyl) 2 methoxyethylamine as nt identified above, is cooled to O C with an ve ice bath and glacial acetic acid ( 72 g) m potassium cyanate ( 89 g) and methanol R 3 ( 100 ml) are added The mixture is refluxed n, for ninety minutes, cooled and washed with ed saturated sodium bicarbonate solution, and m the organic layer is dried over anhydrous st sodium sulfate and then concentrated to nt give a semisolid Trituration with 300 ml of I ether and filtration gives the title product as yl, a yellow crystal; m p 152 -154 C.
1,579,862 EXAMPLE 3
I -( 2-butoxyethyl)-4-phenyl-4imrnidazolin-2-one Phenacyl bromide ( 10 g) in 50 ml of chloroform is added over 20 minutes to a mixture of 2 butoxyethylamine ( 6 g) and triethylamine ( 7 g) in 50 ml of chloroform at O C The mixture is stirred for 2 hours.
Water ( 100 ml) is added, the organic layer separated, and cooled to O C to give N (phenacyl) 2 butoxyethylamine, to which and glacial acetic acid ( 5 ml), potassium cyanate ( 5 g) and methanol ( 20 ml.) are added The mixture is refluxed for ninety minutes, cooled, washed with saturated sodium bicarbonate solution, dried, and solvent removed to give the title product.
EXAMPLE 4
1-( 2-methoxyethyl)-4-( 2-chlorophenyl)4-imidazolin-2-one To o-chlorophenacyl bromide ( 23 4 g) in ml of chloroform is added over 30 minutes 2 methoxyethylamine ( 20 g) in 100 ml of chloroform which is cooled with an ice bath The mixture is stirred for an additional hour at O C Water ( 200 ml) is added and the organic layer is separated cooled to O C with an ice bath to give N ( 2 chlorophenacyl) 2 methoxyethylamine to which glacial acetic acid ( 8 ml.), potassium cyanate ( 9 g) and methanol are added The mixture is refluxed for 90 minutes, cooled, washed with saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate and solvent removed to give the title product.
EXAMPLE 5
1-( 2-methoxyethyl)-4-(substituted phenyl)-4-imidazolin-2-ones The following 1 ( 2 methoxyethyl) 4 (substituted phenyl) 4 imidazolin 2 ones are prepared in an identical manner to that described in Example 4:
a) I ( 2 methoxyethyl) 4 ( 2,4dichlorophenyl) 4 imidazolin 2 one, via intermediate N ( 2,4 dichlorophenacyl) 2 methoxyethylamine; and b) 1 2 methoxyethyl) 4 (p trifluoromethylphenyl) 4 imidazolin 2 one, via intermediate N (p trifluoromethylphenacyl) 2 methoxyethylamine.
EXAMPLE 6 l-( 2-benzoyloxyethyl)-4-phenyl-4imidazolin-2-one Approximately 15 g of 2phenyloxazoline and 20 g of phenacyl bromide is refluxed in 100 ml of chloroform for 1 hour The solvent, containing N (phenacyl) 2 benzoyloxyethylamine, is concentrated under reduced pressure and acetic acid ( 10 ml.), potassium cyanate ( 9 g) and methanol ( 100 ml) are added and the mixture refluxed for 1 hour The methanol is removed under reduced pressure and the residue taken up in 200 ml of methylene chloride and washed with saturated sodium bicarbonate solution The organic layer is dried and concentrated to give the title compound.
EXAMPLE 7
Preparation of other 1-( 2-acyloxyethyl)4-phenyl-4-imidazolin-2-ones The following I ( 2 acyloxyethyl) 4 phenyl 4 imidazolin 2 ones are prepared by procedures identical to that described for the benzoyloxy derivatives of Example 6:
a) 1 l 2 (propionyloxy)ethyll 4phenyl 4 imidazolin 2 one via intermediate N (phenacyl) 2(propionyloxy)ethylamine; b) 1 l 2 (pmethylbenzoyloxy)ethyll 4 phenyl 4 imidazolin 2 one via intermediate N (phenacyl) 2 p methylbenzoyloxy)ethylamine; and c) 1 l 2 (p trifluoromethylbenzoyloxy)ethyll 4 phenyl 4 imidazolin 2 one via intermediate N (phenacyl) 2 (p trifluoromethylbenzoyloxyethylamine.
EXAMPLE 8
The following amino ketones of formula I are prepared by the reaction of the corresponding derivatized ethanolamines of their acid addition salts with the corresponding phenacyl bromides as in the first three sentences of Example 2:
R 2 CCH 2 NHCH 2 CH 2 OR C 6 H 5 C 6 H 5 C 6 H, C 6 H 5 C 6 H 5 C 6 H 5 C 6 H 5 C 6 H 5 C 6 H 5 C 6 H 5 C 6 H 5 C 6 H, m OCH 3 C 6 H 4 mn CI C 6 H 4 rn-B r-C 6 H 4 m CI C 6 H 4 C 6 H 5 C 6 H 5 C 6 H 5 m-OCHI-C 6 H, m Cl-CH, m-Br-C 6 H, m-Cl-C^H CTT C Hl CH, (I) R C 2 H 5 CH 7-i CH 2 CH 2 C 1 C 6 H 5 C 6 H 4-(p-CH 3) C 6 H 4-(p-Cl) C 6 H 4-(p-OCH 3) C 6 H 4-(m-OCH 3) C(O)C 2 H 5 C(O)C 4 H 9 C(O)OCH 3 C(O)OC 6 H 5 CH 3 H H C(O)CH 3 C(O)OC 6 H 4 (p-CH 3) C(O)OC 6 H 4 (o-CH 3) C(O)OC 6 H 4 (P-OCH 3) 1,579,862 C 6 H 5 C(O)C 6 H 5 C 6 H 5 C(O)C 2 H 5 C 6 Hs C(O)C 4 Hg C 6 H 5 C(O)OCH 3 C 6 H 5 C(O)OC 6 H 5 m-OCH 3-C 6 H 4 CH 3 rn-CI-C 6 H 4 H m-B r-C 6 H 4 H m-Cl-C 6 H 4 C(O)CH 3 C 6 H 5 C(O)OC 6 H 4 (p-CH 3) C 6 H 5 C(O)C 6 H 4 (o-CH 3) C 6 H 5 C(O)OC 6 H 4 (p-OCH 3) C 6 H 5 C(O)C 6 H 5 C 6 H 5 C(O)C 6 H 4 (p-CH 3) C 6 H 5 C(O)C 6 H 4 (p-OCH 3) C 6 H 5 C(O)C 6 H 4 (m-CF 3) m-Br-C 6 H 4 C(O)C 6 H 5 m-CF 3-C 6 H 4 CH 3 m-CH 3-C 6 H 4 CH 3 rnm-Cl-C 6 H 4 C 6 H 5 M-CF 3-C 6 H 4 C(O)OCH 3 P-CI-C 6 H 4 CH 3 m-Br-C 6 H 4 C 2 H 5

Claims (9)

WHAT WE CLAIM IS:-
1 A compound of the general formula; R 2-C-CH 2-NH-CH 2-CH 2-OR wherein R is chosen from: hydrogen, alky C 1,-C 6, halo alkyl C,-C 6, phenyl optionally substituted with up to three groups consisting of alkyl C,-C 6, halo and alkyl C,-C 6, halo C 1-C 6 alkyl, alkoxy formula COR; wherein R 3 is hydrogen, alkyl C 1-C 6, halo C,-C 6 alkyl, alkoxy C,-C 6, phenyl or phenoxy optionally substituted with up to four groups consisting of alkyl Cl-C 6, halo, trifluoromethyl or alkoxy C,-C 6; and R 2 is phenyl optionally substituted with up to two groups consisting of alkyl C,-C 6, alkoxy C,-C 6, halo, or trifluoro methyl, with the proviso that R is not hydrogen when R 2 is unsubstituted phenyl.
2 A compound general of the formula:
0 II R 2-C-CH 2-NH-CH 2-CH 2-O R in which R is chosen from hydrogen, C 1,-C 6 alkyl, halo C,-C 6 alkyl, or phenyl optionally substituted with one halogen atom or R is the moiety COR 3 in which R 3 is chosen from hydrogen C,-C 6 alkyl, halo C,-C 6 alkyl, and phenyl optionally substituted with one halogen atom; and R 2 is chosen from trifluorophenylmethyl and phenyl optionally substituted with one or two halogen atoms, with the proviso that R is not hydrogen when R 2 is unsubstituted phenyl.
3 A compound according to Claim l and specifically identified in any one of the Examples herein.
4 A method for the preparation of a compound defined in Claim I, which comprises reacting an a-substituted ketone of the formula:
R 2-C-CH 2-X wherein R 2 is as defined in Claim 1, and X is a group which can be displaced by a nucleophilic reagent, with an amine of the formula:
H 2 N-CH 2-CH 2 OR wherein R is as defined in Claim 1, in an excess of said amine, or in the presence of a tertiary amine, or in the presence of a hydroxide source, at a temperature from 0 C to 50 C for at least 30 minutes.
A method according to Claim 4 wherein R and R 2 are as defined in Claim 2.
6 A method of preparing a compound in accordance with Claim 1, which comprises reacting a compound of the formula:
R 2 COCH 2 X wherein R 2 and X are as defined in Claim 1 and Claim 4 respectively, with a compound of the formula:
-'u R 3 O wherein R 3 is as defined in Claim 1, at a temperature of 25 C to 65 C in a solvent for the reaction.
7 A method in accordance with Claim 6, wherein R 2 and R 3 are as defined in Claim 2.
8 A method for the preparation of a compound in accordance with Claim 1, substantially as described in any one of the Examples herein.
9 A compound according to Claim 1 and produced by methods according to any one of Claims 4 to 8.
TREGEAR, THIEMANN & BLEACH, Chartered Patent Agents, Enterprise House, Isambard Brunel Road, Portsmouth P 01 2 AN.
and 49/51, Bedford Row, London WC 1 V 6 BL.
' Printed for Her Majesty's Stationery Office, by the Courier Press, Leamington Spa 1980 Published by The Patent Office, 25 Southampton Buildings, London WC 2 A l AY from which copies may be obtained.
GB3668/79A 1976-04-26 1977-03-17 N-phenylacyl-2-hydroxyethylamines Expired GB1579862A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US68031176A 1976-04-26 1976-04-26
US05/739,924 US4090025A (en) 1976-04-26 1976-11-08 Intermediates for synthesis of tetramisole, levamisole and their derivatives

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GB3668/79A Expired GB1579862A (en) 1976-04-26 1977-03-17 N-phenylacyl-2-hydroxyethylamines
GB11485/77A Expired GB1579861A (en) 1976-04-26 1977-03-17 1,4-disubstituted 4-imidazolin-2-ones,1,4-disubstituted imidazolin-2-ones and 1,4-disubstituted imidazolidin-2-thiones and their use in non-asymmetric synthesis of tetramisole levamisole and their derivatives

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GB11485/77A Expired GB1579861A (en) 1976-04-26 1977-03-17 1,4-disubstituted 4-imidazolin-2-ones,1,4-disubstituted imidazolin-2-ones and 1,4-disubstituted imidazolidin-2-thiones and their use in non-asymmetric synthesis of tetramisole levamisole and their derivatives

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JP (1) JPS52142067A (en)
AU (1) AU2341277A (en)
DD (1) DD131175A5 (en)
DE (1) DE2718059A1 (en)
DK (1) DK181177A (en)
ES (1) ES458164A1 (en)
FR (1) FR2370735A1 (en)
GB (2) GB1579862A (en)
IL (1) IL51654A0 (en)
IT (1) IT1086883B (en)
NL (1) NL7704424A (en)
NO (1) NO771422L (en)
NZ (1) NZ183622A (en)
SE (1) SE7704745L (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL51639A0 (en) * 1976-04-26 1977-05-31 American Cyanamid Co New synthesis of tetramisole levamisole and their derivatives

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3726894A (en) * 1971-06-24 1973-04-10 American Cyanamid Co The compound 1-(2-hydroxyethyl)-4-phenyl-2-imidazolidinethione
GB1435900A (en) * 1972-10-04 1976-05-19 Agfa Gevaert Method for the preparation of planographic printing plates
FR2258379A1 (en) * 1974-01-21 1975-08-18 Aries Robert Imidazo thiazolidine anthelmintics - prepd from an ethylene thiourea and a haloethanol, halogenation and cyclisation

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NO771422L (en) 1977-10-27
NL7704424A (en) 1977-10-28
ES458164A1 (en) 1978-08-16
IL51654A0 (en) 1977-05-31
JPS52142067A (en) 1977-11-26
AU2341277A (en) 1978-09-21
NZ183622A (en) 1980-04-28
FR2370735A1 (en) 1978-06-09
DD131175A5 (en) 1978-06-07
DK181177A (en) 1977-10-27
SE7704745L (en) 1977-10-27
DE2718059A1 (en) 1977-11-10
IT1086883B (en) 1985-05-31
GB1579861A (en) 1980-11-26

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