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GB1437801A - Synthetic antigens - Google Patents

Synthetic antigens

Info

Publication number
GB1437801A
GB1437801A GB2295973A GB2295973A GB1437801A GB 1437801 A GB1437801 A GB 1437801A GB 2295973 A GB2295973 A GB 2295973A GB 2295973 A GB2295973 A GB 2295973A GB 1437801 A GB1437801 A GB 1437801A
Authority
GB
United Kingdom
Prior art keywords
hemisuccinate
ol
compound
carboxyphenylhydrazone
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB2295973A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Biological Developments Inc
Original Assignee
Biological Developments Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to US25363272A priority Critical
Application filed by Biological Developments Inc filed Critical Biological Developments Inc
Publication of GB1437801A publication Critical patent/GB1437801A/en
Application status is Expired legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D457/00Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid
    • C07D457/04Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid 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 in position 8
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D489/00Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula:
    • C07D489/02Heterocyclic compounds containing 4aH-8, 9 c- Iminoethano-phenanthro [4, 5-b, c, d] furan ring systems, e.g. derivatives of [4, 5-epoxy]-morphinan of the formula: with oxygen atoms attached in positions 3 and 6, e.g. morphine, morphinone
    • GPHYSICS
    • G01MEASURING; TESTING
    • G01NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/94Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving narcotics or drugs or pharmaceuticals, neurotransmitters or associated receptors
    • G01N33/9406Neurotransmitters

Abstract

1437801 Steriod-protein conjugates BIOLOGICAL DEVELOPMENTS Inc 15 May 1973 [15 May 1972] 22959/73 Headings C2C and C2U [Also in Division A5] The following steroid and drug derivatives are prepared (as intermediates in the preparation of antigen conjugates) as follows: (i) 4-pregnen- 6# - ol - 3,20 - diene - 6 - hemisuccinate; 5- cholesten - 3#,7# - diol - 7 - hemisuccinate and 1,3,5(10) - estratrien - 3,6x,17# - triol - 6 - hemisuccinate by treating the corresponding free base with succinic anhydride in pyridine; (ii) 4 - androstan - 15#ol - 6 - hemisuccinate; 5- cholesten - 3# - ol - 7 - hemisuccinate; 1,3,5(10)- estratrien - 3,17# - diol - 6 - hemisuccinate and dihydroteolosterone - 6 - hemisuccinate by reacting the corresponding 6- or 7-chloro compound with mono-tetramethylammonium succinate; (iii) 4-androsten-17#-ol-3,6-dione 6 - (p - carboxyphenylhydrazone); 5 - cholesten- 3# - ol - 7 - one 7 - (p - carboxyphenylhydrazone); 1,3,5(10) - estratrien - 3,17# - diol - 6- one 6 - (p - carboxyphenylhydrazone and dihydrotestosterone - 6 - (p - carboxyphenylhydrazone) by reacting the corresponding parent ketone with p-carboxyphenylhydrazine; (iv) the compound of the formula is prepared by reacting benzene 1,4-diisocyanate with 4-pregnen-6#-ol-3,20-dione in acetone. The compound of formula is obtained analogously using benzene 1,4- diisothiocyanate. The same steroid gives the compound of formula on reaction with benzene 1,4-dicarboxylic acid chloride. The compound of formula is prepared by reacting morphine-2-amino-3- methylether with 4 - carboxybenzaldehyde; PGE - methylester - 10 - hemisuccinate is prepared by reacting 10-bromo PGE with monotetramethylammonium succinate and reaction of the 4-formaldehyde derivative of phenobarbital gives the compound of formula on treatment with p-phenylenediamino. The compound 4-androsten-17#-ol-3,6-dione 6-(p-carboxyphenylhydrazone) prepared as described above is coupled with keyhole limpet homocyanin, immune gamma globulin and bovine serum albumin by treating the steroid with 1-cyclohexyl-3-(2-morpholinoethyl)-carbodiimide metho-p-toluene sulphonate to form an azo-pseudourea which couples with the above proteins on contact. A conjugate is also produced by treating a mixture of #-9-tetrahydrocannibol azobenzoic acid and tributylamine with isobutylchlorocarbonate and adding bovine serum albumin to the resultant.
GB2295973A 1972-05-15 1973-05-15 Synthetic antigens Expired GB1437801A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US25363272A true 1972-05-15 1972-05-15

Publications (1)

Publication Number Publication Date
GB1437801A true GB1437801A (en) 1976-06-03

Family

ID=22961066

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2295973A Expired GB1437801A (en) 1972-05-15 1973-05-15 Synthetic antigens

Country Status (5)

Country Link
JP (1) JPS4941526A (en)
AT (1) AT340065B (en)
DE (1) DE2324544A1 (en)
FR (1) FR2184847B1 (en)
GB (1) GB1437801A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0028795A2 (en) * 1979-11-13 1981-05-20 Miles Laboratories, Inc. Valproic acid conjugates and antibodies thereto

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1446536A (en) * 1975-02-21 1976-08-18 Yeda Res & Dev Pharmaceutically active compositions
JPS6139622B2 (en) * 1975-02-28 1986-09-04 Daiichi Seiyaku Co
IL47372A (en) * 1975-05-27 1979-10-31 Yeda Res & Dev Fab'dimers bound to daunomycin or adriamycin,their preparation and pharmaceutical compositions containing same
JPS5728910B2 (en) * 1976-11-25 1982-06-19
US4069105A (en) * 1977-03-03 1978-01-17 Syva Company Lidocaine antigens and antibodies
GB2013688B (en) * 1978-01-26 1982-06-30 Technicon Instr Insolubilised proteins and immunoassays utilising them
US4264571A (en) * 1979-01-22 1981-04-28 George Washington University Radioimmunoassay of thymosin α1
US4243608A (en) * 1979-05-14 1981-01-06 E. R. Squibb & Sons, Inc. 3-(4-Hydroxyphenyl)pentanedioic acid, monohydrazide, derivatives and analogs
US4587046A (en) * 1982-05-18 1986-05-06 The Regents Of The University Of California Drug-carrier conjugates
US4486344A (en) * 1983-03-28 1984-12-04 Miles Laboratories, Inc. Urea-linked immunogens, antibodies, and preparative method

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0028795A2 (en) * 1979-11-13 1981-05-20 Miles Laboratories, Inc. Valproic acid conjugates and antibodies thereto
EP0028795A3 (en) * 1979-11-13 1982-03-31 Miles Laboratories Inc. Valproic acid konjugates, antibodies thereto and intermediates for their preparation

Also Published As

Publication number Publication date
AU5570273A (en) 1974-11-21
JPS4941526A (en) 1974-04-18
FR2184847A1 (en) 1973-12-28
DE2324544A1 (en) 1973-11-29
ATA426073A (en) 1977-03-15
AT340065B (en) 1977-11-25
FR2184847B1 (en) 1978-05-26

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee