DE2202441C3 - - Google Patents
Info
- Publication number
- DE2202441C3 DE2202441C3 DE2202441A DE2202441A DE2202441C3 DE 2202441 C3 DE2202441 C3 DE 2202441C3 DE 2202441 A DE2202441 A DE 2202441A DE 2202441 A DE2202441 A DE 2202441A DE 2202441 C3 DE2202441 C3 DE 2202441C3
- Authority
- DE
- Germany
- Prior art keywords
- barbituric acid
- substituted
- acid derivative
- unsubstituted
- protein
- 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
Links
- 102000036639 antigens Human genes 0.000 claims description 42
- 108091007433 antigens Proteins 0.000 claims description 42
- 102000004169 proteins and genes Human genes 0.000 claims description 42
- 108090000623 proteins and genes Proteins 0.000 claims description 42
- 239000000427 antigen Substances 0.000 claims description 41
- 150000007656 barbituric acids Chemical class 0.000 claims description 31
- DNZPLHRZXUJATK-UHFFFAOYSA-N 2-sulfanylidene-5-[[5-[2-(trifluoromethyl)phenyl]furan-2-yl]methyl]-1,3-diazinane-4,6-dione Chemical class FC(F)(F)C1=CC=CC=C1C(O1)=CC=C1CC1C(=O)NC(=S)NC1=O DNZPLHRZXUJATK-UHFFFAOYSA-N 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 24
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 claims description 24
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 16
- 229920001184 polypeptide Polymers 0.000 claims description 15
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 15
- 241001465754 Metazoa Species 0.000 claims description 14
- 229960001412 pentobarbital Drugs 0.000 claims description 12
- 230000003053 immunization Effects 0.000 claims description 8
- FTOAOBMCPZCFFF-UHFFFAOYSA-N 5,5-diethylbarbituric acid Chemical compound CCC1(CC)C(=O)NC(=O)NC1=O FTOAOBMCPZCFFF-UHFFFAOYSA-N 0.000 claims description 6
- 230000005764 inhibitory process Effects 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 230000009918 complex formation Effects 0.000 claims description 4
- 108010074605 gamma-Globulins Proteins 0.000 claims description 4
- 108010044091 Globulins Proteins 0.000 claims description 3
- 102000006395 Globulins Human genes 0.000 claims description 3
- 229960002319 barbital Drugs 0.000 claims description 3
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 claims description 3
- 229960002695 phenobarbital Drugs 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 2
- 230000010807 negative regulation of binding Effects 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 235000018102 proteins Nutrition 0.000 description 36
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 25
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 125000003277 amino group Chemical group 0.000 description 12
- -1 alkyl radicals Chemical class 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 238000000502 dialysis Methods 0.000 description 6
- 210000002966 serum Anatomy 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000000890 antigenic effect Effects 0.000 description 4
- 239000013060 biological fluid Substances 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 241000283690 Bos taurus Species 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 150000001718 carbodiimides Chemical class 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000932 sedative agent Substances 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- 238000004435 EPR spectroscopy Methods 0.000 description 2
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical class N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229940098773 bovine serum albumin Drugs 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000012024 dehydrating agents Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229960002989 glutamic acid Drugs 0.000 description 2
- 235000013922 glutamic acid Nutrition 0.000 description 2
- 239000004220 glutamic acid Substances 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 229920002643 polyglutamic acid Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000002285 radioactive effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229940125723 sedative agent Drugs 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RNXVXXXZBIXZMS-UHFFFAOYSA-N (4-aminophenyl)arsinic acid Chemical compound NC1=CC=C([AsH](O)=O)C=C1 RNXVXXXZBIXZMS-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical class CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 108010017384 Blood Proteins Proteins 0.000 description 1
- 102000004506 Blood Proteins Human genes 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 206010010071 Coma Diseases 0.000 description 1
- 206010013654 Drug abuse Diseases 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 108091006905 Human Serum Albumin Proteins 0.000 description 1
- 102000008100 Human Serum Albumin Human genes 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 108010020346 Polyglutamic Acid Proteins 0.000 description 1
- 108010039918 Polylysine Proteins 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 108010071390 Serum Albumin Proteins 0.000 description 1
- 102000007562 Serum Albumin Human genes 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- IUJDSEJGGMCXSG-UHFFFAOYSA-N Thiopental Chemical compound CCCC(C)C1(CC)C(=O)NC(=S)NC1=O IUJDSEJGGMCXSG-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 125000000539 amino acid group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- XKNKHVGWJDPIRJ-UHFFFAOYSA-N arsanilic acid Chemical compound NC1=CC=C([As](O)(O)=O)C=C1 XKNKHVGWJDPIRJ-UHFFFAOYSA-N 0.000 description 1
- 229950002705 arsanilic acid Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 238000004638 bioanalytical method Methods 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 239000012888 bovine serum Substances 0.000 description 1
- 244000144987 brood Species 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000006957 competitive inhibition Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- AWADHHRPTLLUKK-UHFFFAOYSA-N diazanium sulfuric acid sulfate Chemical compound [NH4+].[NH4+].OS(O)(=O)=O.[O-]S([O-])(=O)=O AWADHHRPTLLUKK-UHFFFAOYSA-N 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 1
- 229960002456 hexobarbital Drugs 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 230000002163 immunogen Effects 0.000 description 1
- 238000001114 immunoprecipitation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 229920000729 poly(L-lysine) polymer Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000656 polylysine Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 238000011896 sensitive detection Methods 0.000 description 1
- 230000000405 serological effect Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229960003279 thiopental Drugs 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 239000000080 wetting agent Substances 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
- G01N33/94—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
- G01N33/948—Sedatives, e.g. cannabinoids, barbiturates
-
- 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
-
- 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
- Y10S436/815—Test for named compound or class of compounds
- Y10S436/816—Alkaloids, amphetamines, and barbiturates
-
- 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
- Y10S436/823—Immunogenic carrier or carrier per se
-
- 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
- Y10S530/00—Chemistry: natural resins or derivatives; peptides or proteins; lignins or reaction products thereof
- Y10S530/806—Antigenic peptides or proteins
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Biochemistry (AREA)
- Urology & Nephrology (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Hematology (AREA)
- Organic Chemistry (AREA)
- Biomedical Technology (AREA)
- Genetics & Genomics (AREA)
- Microbiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Anesthesiology (AREA)
- Biotechnology (AREA)
- Cell Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biophysics (AREA)
- Food Science & Technology (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Peptides Or Proteins (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17451771A | 1971-08-24 | 1971-08-24 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2202441A1 DE2202441A1 (de) | 1973-03-01 |
| DE2202441B2 DE2202441B2 (de) | 1980-04-10 |
| DE2202441C3 true DE2202441C3 (OSRAM) | 1981-01-15 |
Family
ID=22636461
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2202441A Granted DE2202441B2 (de) | 1971-08-24 | 1972-01-19 | Barbitursäureantigene und spezifische Antikörper hierfür |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3766162A (OSRAM) |
| JP (1) | JPS5928864B2 (OSRAM) |
| CA (1) | CA956889A (OSRAM) |
| DE (1) | DE2202441B2 (OSRAM) |
| GB (1) | GB1327545A (OSRAM) |
Families Citing this family (76)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL171930C (nl) * | 1972-05-11 | 1983-06-01 | Akzo Nv | Werkwijze voor het aantonen en bepalen van haptenen, alsmede testverpakkingen. |
| US4022878A (en) * | 1972-05-15 | 1977-05-10 | Biological Developments, Inc. | Methods and compounds for producing specific antibodies |
| US3995021A (en) * | 1972-05-15 | 1976-11-30 | Biological Developments, Inc. | Antigens of 5,5'alkylphenyl barbituric acids and related hydantoin compounds |
| US3856469A (en) * | 1973-01-02 | 1974-12-24 | Syva Corp | Interferant removal from amphetamine immunoassay |
| US3998943A (en) * | 1973-10-02 | 1976-12-21 | Syva Company | Double receptor fluorescent immunoassay |
| US3979507A (en) * | 1973-11-23 | 1976-09-07 | Wilson Pharmaceutical & Chemical Corporation | Diagnostic system for organ abnormalities |
| US3963691A (en) * | 1974-10-07 | 1976-06-15 | Merck & Co., Inc. | Synthetic antigens of luteinizing hormone releasing hormone |
| US3952091A (en) * | 1974-10-23 | 1976-04-20 | Hoffmann-La Roche Inc. | Simultaneous multiple radioimmunoassay |
| US4036823A (en) * | 1975-04-28 | 1977-07-19 | Biological Developments, Inc. | Barbituric acid antigenic conjugates, their preparation, antibodies and use |
| USRE32696E (en) * | 1975-09-04 | 1988-06-14 | Akzona Incorporated | Enzymatic immunological method for determination of antigens and antibodies |
| US4101549A (en) * | 1976-05-26 | 1978-07-18 | Hoffmann-La Roche Inc. | Aminophenyl esters of 5-carboxyalkyl barbituric acids |
| JPS5341420A (en) * | 1976-09-29 | 1978-04-14 | Mochida Pharm Co Ltd | Immunochemically measuring methoa of hapten |
| US4816253A (en) * | 1977-12-08 | 1989-03-28 | Likhite Vilas V | Novel mutant strain of Listeria monocytogenes and its use in production of IgM antibodies and as an immunotherapeutic agent |
| US4567041A (en) * | 1977-12-08 | 1986-01-28 | Likhite Vilas V | Mutant strain of Listeria monocytogenes and its use in production of IgM antibodies and as an immunotherapeutic agent |
| JPS55500053A (OSRAM) * | 1978-01-16 | 1980-01-31 | ||
| US4347312A (en) * | 1980-03-20 | 1982-08-31 | Research Triangle Institute | Detection of antibiotics in milk |
| US4645828A (en) | 1984-03-23 | 1987-02-24 | Oncogen | Platelet related growth regulator |
| IE64785B1 (en) | 1985-04-08 | 1995-09-06 | Genetic Systems Corp | Expression of immunologically reactive viral proteins |
| US4721704A (en) * | 1986-05-09 | 1988-01-26 | Peninsula Laboratories, Inc. | Potent synthetic atrial peptide analogs |
| US5099020A (en) * | 1989-11-27 | 1992-03-24 | Abbott Laboratories | Barbiturate assay compositions and methods |
| CH678394A5 (OSRAM) * | 1990-08-22 | 1991-09-13 | Cerny Erich H | |
| US6699474B1 (en) * | 1990-08-20 | 2004-03-02 | Erich Hugo Cerny | Vaccine and immunserum against drugs of abuse |
| US5414085A (en) * | 1992-04-06 | 1995-05-09 | Biosite Diagnostics, Inc. | Barbiturate derivatives and protein and polypeptide barbiturate derivative conjugates and labels |
| US5869445A (en) * | 1993-03-17 | 1999-02-09 | University Of Washington | Methods for eliciting or enhancing reactivity to HER-2/neu protein |
| US5801005A (en) * | 1993-03-17 | 1998-09-01 | University Of Washington | Immune reactivity to HER-2/neu protein for diagnosis of malignancies in which the HER-2/neu oncogene is associated |
| US6953573B1 (en) | 1993-03-17 | 2005-10-11 | University Of Washington | Compounds for eliciting or enhancing immune reactivity to HER-2/neu protein for prevention or treatment of malignancies in which the HER-2/neu oncogene is associated |
| DK0814843T3 (da) * | 1995-03-31 | 2004-03-29 | Xenova Res Ltd | Haptenbærerkonjugater til anvendelse i behandling af stofmisbrug |
| US5876727A (en) * | 1995-03-31 | 1999-03-02 | Immulogic Pharmaceutical Corporation | Hapten-carrier conjugates for use in drug-abuse therapy and methods for preparation of same |
| US5840307A (en) * | 1995-03-31 | 1998-11-24 | Immulogic Pharmacuetical Corp. | Hapten-carrier conjugates for use in drug-abuse therapy and methods for preparation |
| US6942862B2 (en) * | 1996-04-01 | 2005-09-13 | University Of Washington | Methods and compositions to generate immunity in humans against self tumor antigens by immunization with homologous foreign proteins |
| US6232082B1 (en) | 1998-12-01 | 2001-05-15 | Nabi | Hapten-carrier conjugates for treating and preventing nicotine addiction |
| US6696254B2 (en) | 2001-11-21 | 2004-02-24 | Kimberly-Clark Worldwide, Inc. | Detection and identification of enteric bacteria |
| CA2704273C (en) | 2002-02-21 | 2016-01-05 | Institute Of Virology | Mn/ca ix-antibody binding specifically to non-immunodominant epitope of mn/ca ix and uses thereof |
| AU2003230925A1 (en) * | 2002-04-16 | 2003-11-03 | The Regents Of The University Of California | Methods or renal cell carcinoma prognosis and treatment selection with carbonic anhydrase ix |
| US20070041971A1 (en) * | 2003-07-07 | 2007-02-22 | Wagner David H | Methods for predicting development of auto-immune diseases and treatment of same |
| DE602004028270D1 (de) | 2003-11-04 | 2010-09-02 | Novartis Vaccines & Diagnostic | Verwendung von antagonisten-anti-cd40-antikörpern zur behandlung von chronisch lymphozytischer leukämie |
| JP4765040B2 (ja) | 2003-11-04 | 2011-09-07 | ノバルティス バクシンズ アンド ダイアグノスティックス，インコーポレーテッド | 多発性骨髄腫の処置のためのアンタゴニスト抗ｃｄ４０モノクローナル抗体の使用 |
| PT1680141E (pt) | 2003-11-04 | 2010-12-20 | Novartis Vaccines & Diagnostic | Métodos terapêuticos para tumores sólidos que expressam o antigénio de superfície celular cd40 |
| SI1694360T1 (sl) | 2003-11-04 | 2010-12-31 | Novartis Vaccines & Diagnostic | Uporaba antagonističnih anti-CD40 protiteles za zdravljenje avtoimunskih in vnetnih bolezni in zavrnitve transplantata organa |
| US7022492B2 (en) * | 2003-12-15 | 2006-04-04 | Dade Behring Inc. | Ecstasy haptens and immunogens |
| US6991911B2 (en) * | 2003-12-15 | 2006-01-31 | Dade Behring Inc. | Assay for entactogens |
| US20050130243A1 (en) * | 2003-12-15 | 2005-06-16 | Zheng Yi F. | Assay for entactogens |
| US7115383B2 (en) * | 2004-03-22 | 2006-10-03 | Dade Behring Inc. | Assays for amphetamine and methamphetamine |
| US7037669B2 (en) * | 2004-03-22 | 2006-05-02 | Dade Behring Inc. | Assays for amphetamine and methamphetamine using stereospecific reagents |
| WO2006048262A2 (en) * | 2004-11-04 | 2006-05-11 | Roche Diagnostics Gmbh | Classification of acute myeloid leukemia |
| US7842794B2 (en) | 2004-12-17 | 2010-11-30 | Roche Molecular Systems, Inc. | Reagents and methods for detecting Neisseria gonorrhoeae |
| WO2006125117A2 (en) | 2005-05-18 | 2006-11-23 | Novartis Ag | Methods for diagnosis and treatment of diseases having an autoimmune and/or inflammatory component |
| BRPI0710826A2 (pt) | 2006-04-21 | 2011-08-23 | Novartis Ag | composições farmacêuticas de anticorpo anti-cd40 antagonista |
| GB0700133D0 (en) | 2007-01-04 | 2007-02-14 | Humabs Llc | Human cytomegalovirus neutralising antibodies and use thereof |
| WO2010007463A1 (en) | 2008-07-16 | 2010-01-21 | Humabs Llc | Human cytomegalovirus neutralising antibodies and use thereof |
| PL3009449T3 (pl) | 2008-07-16 | 2018-09-28 | Institute For Research In Biomedicine | Przeciwciała neutralizujące ludzkie cytomegalowirusy i ich zastosowanie |
| RU2553325C2 (ru) * | 2008-07-25 | 2015-06-10 | Институт Фо Ресёч Ин Биомедицин | Нейтрализующие антитела против вируса гриппа а и их использование |
| US8871207B2 (en) | 2008-07-25 | 2014-10-28 | Humabs, LLC | Neutralizing anti-influenza A virus antibodies and uses thereof |
| US20130183326A9 (en) | 2009-11-20 | 2013-07-18 | St. Jude Children's Research Hospital | Methods and compositions for modulating the activity of the interleukin-35 receptor complex |
| WO2012075111A1 (en) | 2010-11-30 | 2012-06-07 | Novartis Ag | Uses of anti-cd40 antibodies in combination therapy for b cell-related cancers |
| MX352338B (es) | 2011-07-18 | 2017-11-17 | Inst Res Biomedicine | Anticuerpos neutralizantes del virus de la influenza a y usos de estos. |
| NZ630920A (en) | 2012-03-20 | 2017-01-27 | Humabs Biomed Sa | Antibodies that neutralize rsv, mpv and pvm and uses thereof |
| RS60938B1 (sr) | 2013-10-02 | 2020-11-30 | Medimmune Llc | Neutrališuća antitela na grip a i njihova upotreba |
| WO2016011035A2 (en) | 2014-07-15 | 2016-01-21 | Medlmmune, Llc | Neutralizing anti-influenza b antibodies and uses thereof |
| WO2016055950A1 (en) | 2014-10-08 | 2016-04-14 | Novartis Ag | Combination of human cytomegalovirus neutralizing antibodies |
| WO2016075546A2 (en) | 2014-11-14 | 2016-05-19 | Antonio Lanzavecchia | Antibodies that neutralize ebola virus and uses thereof |
| SI3220947T1 (sl) | 2014-11-18 | 2021-02-26 | Humabs Biomed S.A. | Protitelesa, ki močno nevtralizirajo virus stekline in druge lisaviruse in njihove uporabe |
| PT3303384T (pt) | 2015-06-01 | 2021-10-14 | Medimmune Llc | Moléculas de ligação neutralizantes anti-influenza e suas utilizações |
| US20180179274A1 (en) | 2015-06-26 | 2018-06-28 | Institute For Research In Biomedicine | Proteins comprising a mutated lair-1 fragment and uses thereof |
| WO2017059878A1 (en) | 2015-10-07 | 2017-04-13 | Humabs Biomed Sa | Antibodies that potently neutralize hepatitis b virus and uses thereof |
| IL304940A (en) | 2016-01-13 | 2023-10-01 | Medimmune Llc | A method for treating type A influenza |
| WO2018010789A1 (en) | 2016-07-13 | 2018-01-18 | Humabs Biomed Sa | Novel antibodies specifically binding to zika virus epitopes and uses thereof |
| WO2018193063A2 (en) | 2017-04-19 | 2018-10-25 | Institute For Research In Biomedicine | Novel malaria vaccines and antibodies binding to plasmodium sporozoites |
| WO2019042555A1 (en) | 2017-08-31 | 2019-03-07 | Humabs Biomed Sa | MULTISPECIFIC ANTIBODIES SPECIFICALLY BINDING TO ZIKA VIRUS EPITOPES AND USES THEREOF |
| HRP20231440T1 (hr) | 2018-12-19 | 2024-03-01 | Humabs Biomed Sa | Protutijela koja neutraliziraju virus hepatitisa b i njihova upotreba |
| MX2022002231A (es) | 2019-08-29 | 2022-03-22 | Vir Biotechnology Inc | Composiciones de anticuerpos y metodos para tratar la infeccion por el virus de la hepatitis b. |
| CN118465272B (zh) | 2019-12-04 | 2025-08-19 | 珠海泰诺麦博制药股份有限公司 | 抗人巨细胞病毒抗体及其用途 |
| BR112022026316A2 (pt) | 2020-06-24 | 2023-03-07 | Vir Biotechnology Inc | Anticorpos neutralizantes do vírus da hepatite b engenheirados e usos dos mesmos |
| AU2021389671A1 (en) | 2020-11-24 | 2023-06-22 | Monash University | Induced stem cells |
| TW202245838A (zh) | 2021-01-26 | 2022-12-01 | 美商維爾生物科技股份有限公司 | 用於治療b型肝炎病毒感染的組成物及方法 |
| EP4305058A2 (en) | 2021-03-10 | 2024-01-17 | Mabylon AG | Antibodies against tdp-43 and methods of using the same |
-
1971
- 1971-08-24 US US00174517A patent/US3766162A/en not_active Expired - Lifetime
-
1972
- 1972-01-18 CA CA132,656A patent/CA956889A/en not_active Expired
- 1972-01-18 GB GB240572A patent/GB1327545A/en not_active Expired
- 1972-01-18 JP JP47006720A patent/JPS5928864B2/ja not_active Expired
- 1972-01-19 DE DE2202441A patent/DE2202441B2/de active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB1327545A (en) | 1973-08-22 |
| JPS5928864B2 (ja) | 1984-07-16 |
| US3766162A (en) | 1973-10-16 |
| JPS4828623A (OSRAM) | 1973-04-16 |
| CA956889A (en) | 1974-10-29 |
| DE2202441B2 (de) | 1980-04-10 |
| DE2202441A1 (de) | 1973-03-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2202441C3 (OSRAM) | ||
| DE69332988T2 (de) | Reagenzien zum Nachweis und zur Quantifizierung von Thyroxin in flüssigen Proben | |
| DE3785038T2 (de) | Monoklonale antikoerper gegen nicht reduzierte, nicht enzymatisch glykolysierte proteine. | |
| DE69218981T2 (de) | Verfahren zum Nachweis freier IGF-I, IGF-II, und GH Spiegel in Körperflüssigkeiten | |
| DE2805663C3 (OSRAM) | ||
| DE2953449A1 (de) | Verfahren und ausruestung fuer die enzym-immunoassay von biologischen substanzen | |
| EP0013930B1 (de) | Immunogen, Antikörper für ein Thymus-Hormon, markiertes Thymus-Hormon und Verfahren zur Bestimmung dieses Thymushormons | |
| DE2901218A1 (de) | Ung von theophyllin | |
| DE2653032A1 (de) | Radioimmun-nachweisverfahren fuer ein schilddruesenhormon und dafuer geeignetes reagens | |
| DE69132122T2 (de) | Reinigung von cytokeratinfragmenten | |
| DE3218312C2 (de) | Monoklonale Antikörper, Hybridoma-Zellklone, Verfahren zu ihrer Herstellung und ihre Verwendung zur Erkennung von Brustkrebs und maligner Lymphogranulomatose | |
| DE2608096C2 (OSRAM) | ||
| DE2716536C2 (de) | Methadon-Antigene und Verfahren zur Herstellung dieser | |
| DE1961541A1 (de) | Immunologisches Indikatorreagens | |
| DE60035267T2 (de) | Verfahren zur analyse der menge an intraabdominalem fettgewebe | |
| EP0183901B1 (de) | Bifunktionelle Haptene, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE2548196A1 (de) | Antigene auf basis von methaqualon- hapten sowie deren verwendung | |
| DE2310280A1 (de) | Tubocurarin-antigene | |
| DE3025226C2 (de) | Pterinderivate und ihre Verwendung zur radioimmunologischen Bestimmung von Pterinen | |
| EP0124779A2 (de) | Radioimmunverfahren für Thymosin beta 4 | |
| DE3887727T2 (de) | Partikelstabilisierte Epitope zur Standardisierung und Kontrolle von Immuntests. | |
| DE2714751C2 (OSRAM) | ||
| DE3509958A1 (de) | Monoklonale antikoerper gegen atriale, natriuretische peptide vom menschen | |
| DE2738156A1 (de) | Bestimmung von catecholaminen | |
| DE2126128A1 (de) | Medizinisches Testverfahren, Reagens und Additiv zur Durchführung des Verfahrens |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |