NO161347B - Innretninger og utrustninger for immunologisk analyse og anvendelse av samme. - Google Patents
Innretninger og utrustninger for immunologisk analyse og anvendelse av samme. Download PDFInfo
- Publication number
- NO161347B NO161347B NO821411A NO821411A NO161347B NO 161347 B NO161347 B NO 161347B NO 821411 A NO821411 A NO 821411A NO 821411 A NO821411 A NO 821411A NO 161347 B NO161347 B NO 161347B
- Authority
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- Norway
- Prior art keywords
- undecane
- immunoassays
- aminotricyclo
- sets
- tricyclo
- Prior art date
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- 230000001900 immune effect Effects 0.000 title 1
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 claims description 111
- 150000001875 compounds Chemical class 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 239000007787 solid Substances 0.000 abstract description 7
- 238000006243 chemical reaction Methods 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 3
- 229920006395 saturated elastomer Polymers 0.000 abstract description 2
- 239000000427 antigen Substances 0.000 abstract 4
- 238000003018 immunoassay Methods 0.000 abstract 4
- 108060003951 Immunoglobulin Proteins 0.000 abstract 3
- 102000036639 antigens Human genes 0.000 abstract 3
- 108091007433 antigens Proteins 0.000 abstract 3
- 102000018358 immunoglobulin Human genes 0.000 abstract 3
- 229940072221 immunoglobulins Drugs 0.000 abstract 3
- 239000000020 Nitrocellulose Substances 0.000 abstract 2
- 238000001514 detection method Methods 0.000 abstract 2
- 229920001220 nitrocellulos Polymers 0.000 abstract 2
- 102000000989 Complement System Proteins Human genes 0.000 abstract 1
- 108010069112 Complement System Proteins Proteins 0.000 abstract 1
- VAYOSLLFUXYJDT-RDTXWAMCSA-N Lysergic acid diethylamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N(CC)CC)C2)=C3C2=CNC3=C1 VAYOSLLFUXYJDT-RDTXWAMCSA-N 0.000 abstract 1
- 102000003992 Peroxidases Human genes 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 229920002678 cellulose Polymers 0.000 abstract 1
- 239000003593 chromogenic compound Substances 0.000 abstract 1
- 238000000326 densiometry Methods 0.000 abstract 1
- 238000011156 evaluation Methods 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 230000009871 nonspecific binding Effects 0.000 abstract 1
- 108040007629 peroxidase activity proteins Proteins 0.000 abstract 1
- 210000002966 serum Anatomy 0.000 abstract 1
- 239000007790 solid phase Substances 0.000 abstract 1
- 238000001179 sorption measurement Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- -1 3-(N-ethyl-N-methylamino)-tricyclo-[4,3,1,13,8]Undecane Chemical compound 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000007792 addition Methods 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 239000012280 lithium aluminium hydride Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- JSMDUOFOPDSKIQ-UHFFFAOYSA-N 3-methoxypropanoyl chloride Chemical compound COCCC(Cl)=O JSMDUOFOPDSKIQ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 208000036142 Viral infection Diseases 0.000 description 2
- 241000700605 Viruses Species 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 230000000840 anti-viral effect Effects 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 2
- 208000037797 influenza A Diseases 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 230000009385 viral infection Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 238000006969 Curtius rearrangement reaction Methods 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010035737 Pneumonia viral Diseases 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 206010057190 Respiratory tract infections Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241000282898 Sus scrofa Species 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-M carbonochloridate Chemical compound [O-]C(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-M 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 208000009305 pseudorabies Diseases 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 201000010740 swine influenza Diseases 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- YIMVAVCBOZTFKH-UHFFFAOYSA-N tricyclo[4.3.1.13,8]undecan-3-amine Chemical compound C1C(C2)CC3CC2CC1(N)CC3 YIMVAVCBOZTFKH-UHFFFAOYSA-N 0.000 description 1
- RSJKGSCJYJTIGS-BJUDXGSMSA-N undecane Chemical group CCCCCCCCCC[11CH3] RSJKGSCJYJTIGS-BJUDXGSMSA-N 0.000 description 1
- 208000009421 viral pneumonia Diseases 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
Classifications
-
- 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
- G01N33/543—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals
- G01N33/54393—Improving reaction conditions or stability, e.g. by coating or irradiation of surface, by reduction of non-specific binding, by promotion of specific binding
-
- 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
- G01N33/543—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals
- G01N33/54366—Apparatus specially adapted for solid-phase testing
- G01N33/54386—Analytical elements
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/97—Test strip or test slide
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/975—Kit
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S436/00—Chemistry: analytical and immunological testing
- Y10S436/807—Apparatus included in process claim, e.g. physical support structures
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S436/00—Chemistry: analytical and immunological testing
- Y10S436/821—Chemistry: analytical and immunological testing involving complement factors or complement systems
Landscapes
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Food Science & Technology (AREA)
- Biochemistry (AREA)
- Cell Biology (AREA)
- Biotechnology (AREA)
- Medicinal Chemistry (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Microbiology (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Peptides Or Proteins (AREA)
- Apparatus Associated With Microorganisms And Enzymes (AREA)
Abstract
Oppfinnelsen vedrører nye innretninger og sett for immuno-analyser, spesielt faste-fase-immuno-analyser, omfattende en fast, porøs bærer, fortrinnsvis i form av et ark, hvor antigenet eller immunoglobuliner, eller begge, er bundet ved direkte påfring med ingen ytterligere kjemisk eller elektrokjemisk behandling. Anvendelsen av slike bærere gjør det mulig å utføre et ubegrenset antall av antistoff-antigenreaksjoner samtidig og i en operasjon. Analysene med disse nye sett er teknisk meget enkle i praksis. Antigenene eller lmmunoglobullnene på den faste bæreren kan påføres i en hvilken som helst egnet valgt geometri, f.eks. som en oppstilling av prikker, fortrinnsvis mikroprikker eller linjer. Et foretrukket materiale for den faste bæreren er nitrocellulose eller nitrocellulose blandet med andre celluloseestere.Før utførelse av immuno-analysene må gjenværende adsorbsjonssteder på bæreren mettes med helt serum av heterolog art for å forhindre ikke-spesifikk binding. Oppfinnelsen er også spesielt rettet på innretninger og sett behandlet på denne måte, og, dersom ønsket, vasket og trket. De kan lagres i en ubegrenset tid uten tap av aktivitet.Ved immuno-analyser som skal utfres i henhold til foreliggende oppfinnelse anvendes ved det foretrukne påvisningssystem anti-primære arter av antistoff koblet til peroksydase med et kromogent substrat. Farveintensiteten kan kvantiseres og kalibreres med standarder av kjente mengder av immunoglobuliner bundet til den samme bærer. Densiometri tillater • evaluering av farvereaksjonen over et 1000-fold konsentrasjons-områder.De nye sett kan også anvendes med spesifikke antistoffer i en bestemt oppstilling på den faste bæreren for påvisning av spesifikke antigener og med komplementproteiner for å påvise antigen-antistoffkomplekser.
Description
Fremgangsmåte ved fremstilling av terapeutisk aktive 3-substituerte tricyclo [4,3,1,13'8] undecaner.
Foreliggende oppfinnelse angår fremstilling av nye tricyclo[4,3,l,13,8]undecaner
med en substituert aminogruppe bundet
til et tertiært carbonatom i 3-stilling.
Det er stadig behov for effektive anti-virusmidler som er nyttige ved behandling
av virusinfeksjoner. Det har nu vist seg at
visse nye N-substituerte 3-aminotricyclo-[4,3,l,l3>8]imdecaner har fremragende evne
til å hindre eller sinke forekomsten og
veksten av forskjellige skadelige virus.
Forbindelser fremstilt ifølge oppfinnelsen er i besittelse av en fremragende kombinasjon av egenskaper som viser seg ved
standardprøver i såvel vevskultur som i
dyr. Antiviral aktivitet av de fremstilte
forbindelser har vært iakttatt overfor in-fluensa A (stammer WSN og svin), influ-ensa A-2 (stammer Michigan A/AA og
JPC) og pseudorabies.
Forbindelsene fremstilt ifølge oppfinnelsen har formelen:
hvor R er -NR1R2 hvor'. Ri er en alkylgruppe med 1—6 carbonatomer eller en substituert alkylgruppe, hvor alkylgruppen har 1—6 carbonatomer, og substituenten er en hydroxylgruppe, en alkoxygruppe med 1—2 carbonatomer, -NH2, -NHR3 eller -NR3R4, hvor R3 og R4 kan være like eller forskjellige og er alkylgrupper med 1—4 carbonatomer, og R2 er hydrogen eller har samme betydning som Ri.
Det vil forståes at forbindelsene som faller under formel I som har en basisk aminogruppe, danner syreaddisjonssalter av slike basiske aminer og fremstillingen av slike salter er også innbefattet i oppfinnelsen. Eksempler på slike salter er hydrokloridet, hydrobromidet, sulfatet, fosfa-tet, acetatet, succinatet, adipatet, propio-natet, tartratet, citratet og bicarbonatet. Av disse er hydrokloridet og acetatet de foretrukne.
De ovenfor beskrevne salter øker nyt-tigheten av de relativt uoppløselige aminer ved farmasøytiske anvendelser.
De forbindelser ifølge ovenstående formel I foretrekkes hvor aminet på unde-canenheten er substituert med dialkyl på grunn av deres fremragende kombinasjon av uvanlige egenskaper. Skjønt usubstitu-ert dialkyl er mest fordelaktig, kan noen formuleringsfordeler oppnåes ved anvendelse av spesielle substituerte produkter såsom hydroxy- eller alkoxysubstituerte forbindelser som det vil forståes.
Lavere alkylsubstituenter ' såsom di-methyl og diethyl er de mest foretrukne. Imidlertid er monomethyl- og monoethyl-derivatene foretrukne i forhold til de fleste av de substituerte alkylaminoderivater.
Særlig foretrukne er hydrokloridene av følgende forbindelser: 3-N,N-dimethylaminotricyclo[4,3,l,13.s]-undecan
3-N-methylaminotricyclo [4,3,1,13,8]undecan
3-(N-ethyl-N-methylamino)-tricyclo-[4,3,l,l3,8]Undecan 3-N,N-diethylaminotricyclo[4,3,l,13.8]-undecan
3-N-ethylaminotricyclo [4,3,1,13,8]undecan
Ovenstående forbindelser fremstilles ved at en forbindelse med en generell formel som tilsvarer formel I, men hvor R betyr NH2 eller NHRi hvor Ri har samme betydning som ovenfor og hvor en eventuell substituent NH? eller NHR3 på Ri om nødvendig er beskyttet, acyleres med et passende acyleringsmiddel slik at det dannede acylamid ved påfølgende reduksjon danner substituenten R2, idet eventuelle beskyttende grupper fjernes, hvor-efter den dannede forbindelse om ønskes omdannes til et syreaddisjonssalt derav.
Utgangsmaterialet 3-aminotricyclo-[4,3,l,13.s]undecan kan lett fremstilles fra den kjente forbindelse 3-carboxy tricyclo -
[4,3,l,13,8]undecan ved overføring til syre-kloridet med thionylklorid, fulgt av ami-nering til det tilsvarende amid. Amidet omsettes derpå med metallisk natrium og brom under dannelse av 3-carbomethoxy-aminotricyclo[4,3,l,13,s]undecan som hydrolyseres under basiske betingelser, hvorved man får det ønskede 3-aminotricyclo-[4,3,1,is,s]undecan. Dette er i grunntrek-ket Hofman-fremgangsmåten for omdan-nelse av en carboxylsyre til det tilsvarende amin. Syren kan også omsettes med ethyl-
klorcarbonat og natriumazid og det dannede acylazid spaltes ved opphetning under dannelse av isocyanatet som kan omsettes med methanol under dannelse av methylurethanet som hydrolyseres til aminet med alkali. Dette er en tillempning av Curtius-reaksjonen. Disse to fremgangs-måter for fremstilling av 3-aminotricyclo-[4,3,l,13,8]undecan er beskrevet i de norske patenter nr. 111908 og nr. 111910.
3-N-alkylaminotricyclo[4,3,l,l3.8]un-decanet kan igjen acyleres og reduseres hvorved man får 3-N,N-dialkylaminotri-cyclo[4,3,l,l3.8]undecanene. Forskjellige alkylgrupper kan innføres på samme måte. Reduksjon av 3-acetamidotricyclo [4,3,1, - 13,8]undecan fulgt av omsetning av produktet med butyrylklorid, efterfulgt av reduksjon gir 3-(N-butyl-N-ethylamino)-forbindelsen. Hvis acetylklorid anvendes i stedet, blir produktet selvsagt 3-(N,N-di-ethylamino) - tricyclo [4,3,1,13, s ] undecan hvor alkylgruppene er like.
Fremgangsmåten med acylering og reduksjon kan anvendes for å fremstille forbindelser hvori alkylsubstituentene er substituert. Alkylering av 3-N-methylaminotricyclo[4,3,l,l3,8]undecån med 3-methoxypropionyl-klorid fulgt av reduksjon gir 3-[N-(3-methoxypropyl)-N-met-hylamino] -tricyclo[4,3,1,13.8]undecan. Omsetning av aminet eller monoalkylaminet med et dicarboxylsyreanhydrid for å få det N-substituerte alkansyre-halvamid, fulgt av reduksjon, innfører hydroxyalkylgrup-pen. Således gir f. eks. reduksjonen av N-[ tricyclo [4,3,1,13.s] undecyl- (3) ] -ravsyre-halvamid 3-n- (4-hydroxybutyl)-aminotri-cyclo[4,3,l,l3,8]Undecan.
Eksempler på forbindelsene som fremstilles ifølge oppfinnelsen er følgende forbindelser og deres salter: 3-N-methylaminotricyclo[4,3,l,13.8]undecan 3-N,N-dimethylaminotricyclo[4,3,l,l3,8]-undecan 3-N-hexylaminotricyclo [4,3,1,13,8]undecan 3-N-isoamylaminotricyclo [4,3,1,13,8]undecan 3-N- (1-methylpentyl) -aminotricyclo-[4,3,l,13,8]undecan 3-N- (1,1 -dimethylbutyl) -aminotricyclo-[4,3,1,13,s]undecan 3-(N,N-dihexyl)-aminotricyclo[4,3,l,l3,8]-undecan 3-(N,N-diisohexyl)-aminotricyclo[4,3,l,-13, s] undecan 3- [N,N-di- (1-methylpentyl) -amino] -tricyclo [4,3,1,13,8]undecan 3-[N,N-di-(l,l-dimethylbutyl)-amino]-tricyclo [4,3,1,13,sjundecan 3-N-(hydroxymethyl)-aminotricyclo-[4,3,1,l3.8]undecan 3-N-(methoxymethyl)-aminotricyclo-[4,3,1, la. sjundecan 3-N-(ethoxymethyl)-aminotricyclo-[4,3,1,13.s]undecan 3-N-(aminomethyl)-aminotricyclo[4,3,l,-I», s] undecan
3-N- (N'-methylaminomethyl) -aminotri-cyclo[4,3,l,13,8]undecan 3-N- (N'-butylaminomethyl) -aminotri-cyclo [4,3,1,13,8 ] undecan 3-N- (N'-isobutylaminomethyl)-amino-tricyclo [4,3,1,13, s]undecan 3-N-[N'-methylpropyl)-aminomethyl] - aminotricyclo[4,3,l,l3,8]undecan 3-N- (N'-tert.butylaminomethyl)-amino-tricyclo [4,3,1,13, sjundecan 3-N-(N,N'-dimethylaminomethyl)-amino-tricyclo[4,3,l,13,8]Undecan 3-N- (N'-butyl-N'-methylamino-methyl) - aminotricyclo [4,3,1,13,8 ] undecan 3-N-(N',N'-dibutylaminomethyl)amino-tricyclo[4,3,l,13,8]Undecan 3-N[N'-di-(tert.butyl]aminomethyl]-aminotricyclo [4,3,1,13.8 ] undecan 3-N-(6-hydroxyhexyl)-aminotricyclo-[4,3,1,13.8]Undecan 3-N-(3-hydroxyhexyl)-aminotricyclo-[4,3,1,13.s] undecan 3-N- (6-methoxyhexyl) -aminotricyclo-[4,3,1,13.s]undecan 3-N-(3-methoxyhexyl)-aminotricyclo-[4,3,1,13.sjundecan 3-N-(6-ethoxyhexyl)-aminotricyclo-[4,3,l,13,8]Undecan 3-N- (3-ethoxy-2-methylpentyl)-amino-tricyclo [4,3,1,13,8 ] undecan 3-N-(6-aminohexyl)-aminotricyclo-[4,3,1,13.8]undecan 3-N-(l-amino-l-ethylbutyl)-aminotri-cyclo[4,3,l,13.8]undecan 3-N- (N'-methylaminohexyl) -aminotri-cyclo[4,3,l,13,8]undecan 3-N- (N'-butylaminohexyl) -aminotricyclo-[4,3,1,13,8]Undecan 3-N- (N'-isobutylaminohexyl) -aminotri-cyclo [4,3,1,13. sjundecan 3-N-(N'-tert.butylaminohexyl)-aminotri-cyclo[4,3,l,13,8]undecan 3-N-(N',N'-dimethylaminohexyl)-amino-tricyclo [4,3,1,13,8 ] undecan 3-N- [3- (N',N'-dimethylamino) -hexyl] - aminotricyclo [4,3,1,13,8] undecan 3-N- (N'-butyl-N'-methylaminohexyl) - aminotricyclo [4,3,1,13,8] undecan 3-N- (N'-dibutylaminohexyl) -aminotri-cyclo [4,3,1,1 s, s ] undecan 3-N- (N',N'-diisobutylaminohexyl) -amino-tricyclo[4,3,1,13,sjundecan
3-N- (N'-di-tert.butylaminohexyl)-amino-tricyclo [4,3,1,13,8] undecan
3-N,N-di-(hydroxymethyl)-aminotri-cyclo[4,3,l,13,s]undecan 3-N,N-di-(methoxymethyl)-aminotri-cyclo[4,3,l,13.8]undecan
3 ,N,N-di- (ethoxymethyl) -aminotricyclo-[4,3,1,13,sjundecan
3-N,N-di- (aminomethyl )-aminotricyclo-[4,3,1,13.s]undecan 3-N,N-di-(N'-methylaminomethyl)-aminotricyclo [4,3,1,13,8 ] undecan
3-N,N-di- (N'-butylaminomethyl) -amino-tricyclo [4,3,1,13,8]Undecan 3-N,N-di-(N'-butyl-N'-methylamino-methyl)-aminotricyclo[4,3,l,l3,8]undecan 3-N,N-di- (N',N'-dibutylaminomethyl) - aminotricyclo[4,3,l,13,8]undecan
De følgende eksempler vil ytterligere illustrere oppfinnelsen. Alle deler og pro-senter er angitt i vekt, dersom ikke annet spesielt er angitt.
Eksempel 1.
En 10,35 g prøve (0,05 mol) av 3-acy-lert-tricyclo[4,3,1,13,8]undecan fremstilt ved acetylering av det tilsvarende amin med eddiksyreanhydrid inneholdende en dråpe svovelsyre ble oppløst i 200 ml tørr tetrahydrofuran og tilsatt til en suspensjon av 3,0 g lithiumaluminiumhydrid i 350 ml tørr ether. Efter avsluttet tilsetning ble blandingen kokt under tilbakeløp i 1 time og oppløsningsmidlet destillert av fra re-aksjonskaret. Damp ble så ført inn inntil man fikk et klart destillat. Destillatet ble så ekstrahert med ether og ekstraktet tør-ret med fast natriumhydroxyd. Tørt hydrogenklorid ble så ført inn i den filtrerte oppløsning og det utfelte aminhydroklorid fjernet ved filtrering og omkrystallisert fra ethylacetat-methanol. Utbyttet var 5,6 g 3-N- ethylaminotricyclo [4,3,1,13,8] undecan-hydr oklor id.
Analyse beregnet for C^H^NCl: N 6,09 pst., Cl 15,4 pst.
Funnet: N 6,66 pst., Cl 15,57 pst.
Eksempel 2.
Molare ekvivalenter av 3-aminotri-cydo[4,3,1,13.sjundecan og caproylklorid ble omsatt i pyridinoppløsning til 3-(N-caproylamino)-tricyclo [4,3,1,13,sjundecan som ble isolert ved å helle reaksjonsblandingen i vann og fjerne det krystallinske amid ved filtrering. Efter forsiktig tørring av produktet ble en tetrahydrofuranopp-løsning sakte tilsatt til en suspensjon av en molekvivalent (25 pst. overskudd) av lithiumaluminiumhydrid i diethylether. Efter avsluttet tilsetning ble reaksjonsblandingen kokt under tilbakeløp i 2 timer, oppløsningsmidlet avdestillert og aminet dampdestillert inntil destillatet var klart. Produktet ble ekstrahert med ether og den etheriske oppløsning tørret over fast natriumhydroxyd. Tørt hydrogenklorid ble ført inn i den etheriske oppløsning. For-dampning av etheren ga 3-(N-hexyl-amino)-tricyclo[4,3,l,13,8]undecan-hydro-klorid.
Eksempel 3.
3-N-methylaminotricyclo [4,3,1,13,8].
undecan ble overført til acetylderivatet ved forsiktig oppvarmning av forbindelsen med et lite overskudd av eddiksyreanhydrid inneholdende en dråpe svovelsyre. Den dannede oppløsning ble heldt på is og ekstrahert med kloroform. Fjernelse av kloro-formen ga 3-N-methylacetaminotricyclo-[4,3,1,13,8]undecan som ble renset ved des-tillasjon. En oppløsning av amidet i tetrahydrofuran ble tilsatt sakte til en suspensjon av en molekvivalent av lithiumaluminiumhydrid i diethylether. Efter fullsten-dig tilsetning ble reaksjonsblandingen kokt
under tilbakeløp i 4 timer, oppløsningsmid-let fjernet og aminet isolert ved damp-destillasjon. Dampdestillatet ble ekstrahert med ether og ekstraktet tørret med fast natriumhydroxyd. Den tørre etheriske oppløsning ble mettet med hydrogenklorid og efter fjernelse av etheren fikk man hydrokloridet av 3-(N-methyl-N-ethyl-amino)-tricyclo [4,3,1,13,8]undecan.
Eksempel 4.
Eksempel 2 ble gjentatt under anvendelse av ekvivalente mengder 3-methoxy-propionylklorid i stedet for caproylkloridet for å fremstille 3-(N-methyl-3-methoxy-proplonamido) -tricyclo [4,3,1,13,8] undecan som så ble redusert med lithiumaluminiumhydrid til 3-[N-(3-methoxypropyl)-N-methylamino ] - tricyclo [4,3,1,13,8] undecan.
Eksempel 5.
En blanding av 0,10 mol 3-N-methylaminotricyclo[4,3,l,13,8]undecan og 0,33 mol 85 pst.-ig fosforsyre i 100 ml vann ble konsentrert i vakuum ved 60°C. Det dannede salt, 3-N-methyl-aminotricyclo-[4,3,1,13,s]undecan-fosfat, ble tørret i vakuum ved 60°C.
Eksempler 6- 10
Eksempel 5 ble gjentatt under anvendelse av følgende reaktanter i stedet for dem i nevnte eksempel, hvorved man fikk de angitte produkter:
Forbindelsene av formelen I ovenfor
kan tilføres ved den antivirale behandling
på en hvilken som helst måte som bevirker
kontakt mellom den aktive bestanddel og
virusinfeksjonsområdet i legemet. Det vil
forståes at dette innbefatter området før
infeksjonen finner sted såvel som efter.
Tilførselen kan således være parenteral,
dvs. subcutan, intravenøs, intramuskulær
eller intraperitoneal. Alternativt eller samtidig er forbindelsene effektive ved oral
inngivelse. Da de er særlig effektive mot
åndedrettsinfeksjoner såsom viral lunge-betennelse, kan de inngis i dampform eller
som spray gjennom munnen eller nese-veiene.
Forbindelsene som fremstilles ifølge
oppfinnelsen, er verdifulle ved viral profyl-akse, såvel som for terapeutisk behandling.
Den anvendte dose vil være avhengig
av det virus som skal behandles, alderen,
helbreden og vekten av pasienten, utstrek-ningen av infeksjonen, typen av eventuell
samtidig behandling, hyppigheten av be-handlingen og den effekt som ønskes opp-nådd. I alminnelighet vil en dagdose aktiv
forbindelse være fra ca. 1 til 50 mg pr. kg
legemsvekt, skjønt lavere såsom 0,5 mg,
eller større mengder kan anvendes. Van-ligvis er fra 1 til 20, og fortrinnsvis 1 til 10
mg pr. kg pr. dag, ved én eller flere til-førsler pr. dag, effektive til å gi det ønskede
resultat.
Forbindelsene som fremstilles ved den
foreliggende fremgangsmåte er særlig effektive mot svineinfluensa. En viktig anvendelse er derfor bekjempelse av denne
infeksjon ved inkorporering av den aktive
forbindelse i foret til det angrepne dyr. I
de fleste tilfelle vil der anvendes en meng-de av den aktive forbindelse som gir fra ca.
0,0001 til 0,1 vektprosent aktiv forbindelse,
beregnet på totalvekten av den inntatte
føde. Fortrinnsvis vil der anvendes fra
0,001 til 0,02 vektprosent.
Claims (1)
- Fremgangsmåte ved fremstilling av terapeutisk aktive 3-substituerte tricyclo-[4,3,1,13,s]undecaner med den generelle formel:hvor R er -NR1R2, hvor Ri er en alkylgruppe med 1—6 carbonatomer eller en substituert alkylgruppe, hvilken alkylgruppe har 1—6 carbonatomer idet substituenten er en hydroxylgruppe, en alkoxygruppe med 1—2 carbonatomer, -NH2, -NHR3 eller -NR3R4 hvor R3 og R4 kan være like eller forskjellige og er alkylgrupper med 1—4 carbonatomer, og R2 er hydrogen eller har samme betydning som Ri, samt syreaddisjonssalter av disse forbindelser, karakterisert ved at en forbindelse med en generell formel som tilsvarer formel (I), men hvor R betyr NH2 eller NHRi hvor Ri har samme betydning som ovenfor og hvor en eventuell substituent NH2 eller NHR3 på Ri om nødven-dig er beskyttet, acyleres med et passende acyleringsmiddel slik at det dannede acylamid ved påfølgende reduksjon danner substituenten R2, idet eventuelle beskyttende grupper fjernes, hvoretter den dannede forbindelse om ønskes omdannes til et syreaddisjonssalt derav.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB8113167 | 1981-04-29 | ||
GB8134353 | 1981-11-13 | ||
GB8201289 | 1982-01-18 |
Publications (3)
Publication Number | Publication Date |
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NO821411L NO821411L (no) | 1982-11-01 |
NO161347B true NO161347B (no) | 1989-04-24 |
NO161347C NO161347C (no) | 1989-08-02 |
Family
ID=27261173
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NO821411A NO161347C (no) | 1981-04-29 | 1982-04-28 | Innretninger og utrustninger for immunologisk analyse og anvendelse av samme. |
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CA (1) | CA1200761A (no) |
CY (1) | CY1437A (no) |
DE (1) | DE3269567D1 (no) |
DK (1) | DK160336C (no) |
ES (3) | ES511735A0 (no) |
FI (1) | FI76888C (no) |
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1982
- 1982-04-26 AR AR289207A patent/AR231590A1/es active
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- 1982-04-26 FI FI821441A patent/FI76888C/fi not_active IP Right Cessation
- 1982-04-26 DE DE8282103520T patent/DE3269567D1/de not_active Expired
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- 1982-04-27 IL IL65627A patent/IL65627A/xx not_active IP Right Cessation
- 1982-04-27 GR GR68001A patent/GR75430B/el unknown
- 1982-04-27 ES ES511735A patent/ES511735A0/es active Granted
- 1982-04-28 GB GB8212275A patent/GB2099578B/en not_active Expired
- 1982-04-28 IE IE998/82A patent/IE53295B1/en not_active IP Right Cessation
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- 1982-04-28 AU AU83069/82A patent/AU560790B2/en not_active Expired
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- 1982-04-28 DK DK189182A patent/DK160336C/da not_active IP Right Cessation
- 1982-04-29 BR BR8202492A patent/BR8202492A/pt unknown
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1983
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- 1983-06-30 ES ES523722A patent/ES523722A0/es active Granted
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1987
- 1987-04-10 US US07/038,470 patent/US5486452A/en not_active Expired - Lifetime
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1988
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1989
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