GB1511571A - Lactam compounds and conjugates - Google Patents

Lactam compounds and conjugates

Info

Publication number
GB1511571A
GB1511571A GB1348875A GB1348875A GB1511571A GB 1511571 A GB1511571 A GB 1511571A GB 1348875 A GB1348875 A GB 1348875A GB 1348875 A GB1348875 A GB 1348875A GB 1511571 A GB1511571 A GB 1511571A
Authority
GB
United Kingdom
Prior art keywords
yield
acid
sodium
reacted
diphenylhydantoin
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
GB1348875A
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.)
Syva Co
Original Assignee
Syva Co
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
Application filed by Syva Co filed Critical Syva Co
Publication of GB1511571A publication Critical patent/GB1511571A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • 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
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K16/00—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies
    • C07K16/44—Immunoglobulins [IGs], e.g. monoclonal or polyclonal antibodies against material not provided for elsewhere, e.g. haptens, metals, DNA, RNA, amino acids
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
    • G01N33/531—Production of immunochemical test materials
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/94—Chemical 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
    • G01N33/9446—Antibacterials

Abstract

1511571 Lactam derivatives and intermediates therefor; spin-label compounds SYNTEX ENERGY RESEARCH Ine and VARIAN ENERGY [trading as SYVA CO] 2 April 1975 [28 June 1974] 13488/75 Heading C2C [Also in Divisions C3 and G1] (1.1) The reaction of chloroacetic acid/sodium bicarbonate and sodium diphenylhydantoin yields; 3- (N - carboxymethyl)diphenylhydantoin (1.2) The reaction of sodium diphenylhydantoin and chloroacetonitrile yields; 3-(N-cyanomethyl)- diphenylhydantoin which is hydrolysed with sodium ethoxide/ethanol to; 3 - (N - carboxymethyl)diphenylhydantoin (1.3) Sodium diphenylhydantoin is reacted with ethyl 2-bromopropionate to yield; 2-(N-diphenylhydantoinyl)- propionic acid, ethyl ester which is hydrolysed with aqueous sodium hydroxide to; 2-(N-diphenylhydantoinyl)propionic acid (1.4) Sodium diphenylhydantoin is reacted with ethyl n-5- bromopentanoate to yield; 5-(N<SP>31</SP>-diphenylhydantoinyl)pentanoic acid, ethyl ester which, on hydrolysis with aqueous hydroxide, yields 5 - (N<SP>31</SP> - diphenylhydantoinyl)pentanoic acid (1.5) Sodium diphenylhydantoin is reacted with 2 - chloroethoxyacetonitrile to yield; (2 - (N - diphenylhydantoinyl)ethoxy)acetonitrile which is hydrolysed with sodium hydroxide/ ethanol to; (2 - (N - diphenylhydantoinyl) - ethoxy)acetic acid. (1.6) 5-(p-hydroxyphenyl)- 5 - phenylhydantoin is reacted with sodium chloroacetate to yield; 5-(p-carboxymethoxyphenyl) - 5 - phenylhydantoin. (1.7) Primidone, reduced with sodium hydride, is reacted with ethyl bromoacetate to yield; 2-deoxo-1-barbiturylacetic acid, ethy elster which is hydrolysed with sodium hydroxide to yield; 2-deoxo-1- barbiturylacetic acid. (1.8) Phenyldiethyl malonate, reduced with sodium hydride and the product reacted with 6-bromo-1-hexene to yield; diethyl - 2 - phenyl - 2 - (5<SP>1 </SP>- hexenyl - 1<SP>1</SP>)- malonate which, on ozonolysis, yields; diethyl 2 - phenyl - 2 - (5<SP>1</SP>- pentanal - 1<SP>1</SP> - yl) - malonate which is treated with p-toluene sulphonic acid to yield; diethyl 2-phenyl-(5<SP>1</SP>-pentanal-1<SP>1</SP>-yl)- malonate diethyl acetal which is treated' with thiobarbituric acid, and the product hydrogenated over Raney nickel to yield; 2-deoxo-5- phenyl - 5 - (5<SP>1</SP> - pentanal - 1<SP>1</SP> - yl) - thiobarbituric acid diethyl acetal which is treated with acetic acid to yield; 2-deoxo-5-(5<SP>1</SP>-pentanal-1<SP>1</SP>-yl)barbituric acid which is oxidized with chromic acid/sulphuric acid to; 5-(2<SP>1</SP>-deoxo-5<SP>1</SP>-phenylbarbituryl)pentanoic acid. (1.9) Zerantin, reduced with sodium hydride, is reacted with iodoacetic acid to yield; 1-carboxymethylzarontin. (1.10) Ethyl cyanoacetate and ethyl levalinate are reacted to yield; diethyl 2-cyano-3- methylhex - 2 - en - 1,6 - dionate which is treated with potassium cyanide to yield 2-methyl-2- (21 - cyanomethoxyethyl) - 3 - cyanomethoxysuccinimide; which is treated with sodium hydroxide and phosphonic acid to yield 2- methyl - 2 - (2<SP>1</SP>- carbomethoxyethyl) - 3 - carbomethoxy succinimide which is treated with sodium hydroxide to yield 2-methyl-2-carboxyethyl-3- carboxysuccinimide which is refluxed with acetic acid to yield; 2-carboxyethyl-2-methylsuccinimide. Spin-label compounds were obtained by the reaction of, in triethylamine, 2,2,5,5-tetramethyl - 3 - amino - 1 - oxylpyrrolidine and (4.1) methyl (N<SP>3</SP>-diphenyl hydantoinyl)acetamidate; (4.2) 5-(p-carboxymethoxy phenyl)-5- phenylhydantoin; (4.3) 2-carboxyethyl-2-methylsuccinimide.
GB1348875A 1974-06-28 1975-04-02 Lactam compounds and conjugates Expired GB1511571A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US48402674A 1974-06-28 1974-06-28

Publications (1)

Publication Number Publication Date
GB1511571A true GB1511571A (en) 1978-05-24

Family

ID=23922433

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1348875A Expired GB1511571A (en) 1974-06-28 1975-04-02 Lactam compounds and conjugates

Country Status (5)

Country Link
JP (1) JPS511632A (en)
CA (1) CA1037475A (en)
DE (1) DE2521523A1 (en)
FR (1) FR2276317A1 (en)
GB (1) GB1511571A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0095665A1 (en) * 1982-06-01 1983-12-07 Miles Laboratories, Inc. Labelled conjugates of ethosuximide, ethosuximide immunogens, antibodies thereto, immunoassay method employing the antibodies and reagent means, test kit and test device for the immunoassay method
RU2794719C1 (en) * 2022-05-18 2023-04-24 Федеральное государственное автономное образовательное учреждение высшего образования "Национальный исследовательский Томский политехнический университет" 2-(2,5-dioxo-4,4-diarylymidazolidin-1-yl)carboxy acids, their salts and methods for their production

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4069105A (en) * 1977-03-03 1978-01-17 Syva Company Lidocaine antigens and antibodies
US4156081A (en) * 1977-04-15 1979-05-22 Syva Company Theophylline antigens and antibodies
DE3682105D1 (en) * 1985-04-01 1991-11-28 Abbott Lab SAMPLE, TRACERS, IMMUNOGENIC AND ANTIBODIES OF ETHOSUXIMID.
DE3924705A1 (en) * 1989-07-26 1991-01-31 Boehringer Mannheim Gmbh HETEROBIFUNCTIONAL CONNECTIONS
CN101863834B (en) * 2010-06-29 2012-10-10 渤海大学 Preparation method of S-carboxymethyl-5,5-diphenyl-2-thiohydantoin
KR102267919B1 (en) 2018-06-28 2021-06-23 주식회사 고영테크놀러지 Method and electronic apparatus for determining cause of mounting failure for component mounted on board
US11428644B2 (en) 2018-11-27 2022-08-30 Koh Young Technology Inc. Method and electronic apparatus for displaying inspection result of board
CN115372501B (en) * 2022-07-27 2024-03-26 广州科曼生物科技有限公司 Control extract of fritillaria thunbergii or fritillaria hubei, preparation method and application thereof

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3817837A (en) * 1971-05-14 1974-06-18 Syva Corp Enzyme amplification assay

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0095665A1 (en) * 1982-06-01 1983-12-07 Miles Laboratories, Inc. Labelled conjugates of ethosuximide, ethosuximide immunogens, antibodies thereto, immunoassay method employing the antibodies and reagent means, test kit and test device for the immunoassay method
RU2794719C1 (en) * 2022-05-18 2023-04-24 Федеральное государственное автономное образовательное учреждение высшего образования "Национальный исследовательский Томский политехнический университет" 2-(2,5-dioxo-4,4-diarylymidazolidin-1-yl)carboxy acids, their salts and methods for their production

Also Published As

Publication number Publication date
CA1037475A (en) 1978-08-29
JPS638427B2 (en) 1988-02-23
FR2276317B1 (en) 1979-04-27
FR2276317A1 (en) 1976-01-23
JPS511632A (en) 1976-01-08
DE2521523A1 (en) 1976-01-15

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Legal Events

Date Code Title Description
PS Patent sealed
PE20 Patent expired after termination of 20 years

Effective date: 19950401