CN105273075B - 一种托品酰胺人工抗原的制备方法 - Google Patents
一种托品酰胺人工抗原的制备方法 Download PDFInfo
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- CN105273075B CN105273075B CN201510802311.4A CN201510802311A CN105273075B CN 105273075 B CN105273075 B CN 105273075B CN 201510802311 A CN201510802311 A CN 201510802311A CN 105273075 B CN105273075 B CN 105273075B
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- Prior art keywords
- tropicamide
- artificial antigen
- solution
- reaction
- stirred
- Prior art date
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- BGDKAVGWHJFAGW-UHFFFAOYSA-N Tropicamide Chemical compound C=1C=CC=CC=1C(CO)C(=O)N(CC)CC1=CC=NC=C1 BGDKAVGWHJFAGW-UHFFFAOYSA-N 0.000 title claims abstract description 70
- 229960004791 tropicamide Drugs 0.000 title claims abstract description 70
- 102000036639 antigens Human genes 0.000 title claims abstract description 44
- 108091007433 antigens Proteins 0.000 title claims abstract description 44
- 239000000427 antigen Substances 0.000 title claims abstract description 42
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- 108010074605 gamma-Globulins Proteins 0.000 claims abstract description 21
- 241000283690 Bos taurus Species 0.000 claims abstract description 11
- TXTWXQXDMWILOF-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl)azanium;chloride Chemical compound [Cl-].CCOC(=O)C[NH3+] TXTWXQXDMWILOF-UHFFFAOYSA-N 0.000 claims abstract description 6
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229940014800 succinic anhydride Drugs 0.000 claims abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 30
- 239000000243 solution Substances 0.000 claims description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 235000019441 ethanol Nutrition 0.000 claims description 15
- 238000004809 thin layer chromatography Methods 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 9
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 239000000908 ammonium hydroxide Substances 0.000 claims description 9
- 239000012074 organic phase Substances 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 9
- 239000007853 buffer solution Substances 0.000 claims description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 238000004090 dissolution Methods 0.000 claims description 4
- 239000012153 distilled water Substances 0.000 claims description 4
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims description 3
- OOSZCNKVJAVHJI-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]piperazine Chemical compound C1=CC(F)=CC=C1CN1CCNCC1 OOSZCNKVJAVHJI-UHFFFAOYSA-N 0.000 claims description 3
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 claims description 3
- 238000004587 chromatography analysis Methods 0.000 claims description 3
- 230000006837 decompression Effects 0.000 claims description 3
- 238000000502 dialysis Methods 0.000 claims description 3
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims description 3
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 3
- 238000004321 preservation Methods 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 239000011780 sodium chloride Substances 0.000 claims description 3
- 229940074545 sodium dihydrogen phosphate dihydrate Drugs 0.000 claims description 3
- 239000012265 solid product Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000006228 supernatant Substances 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 239000006227 byproduct Substances 0.000 claims description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims description 2
- 235000019341 magnesium sulphate Nutrition 0.000 claims description 2
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims description 2
- 229910001415 sodium ion Inorganic materials 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 239000005864 Sulphur Substances 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 238000010025 steaming Methods 0.000 claims 1
- 238000001514 detection method Methods 0.000 abstract description 13
- 238000000034 method Methods 0.000 abstract description 9
- 150000001875 compounds Chemical class 0.000 abstract description 8
- 238000003018 immunoassay Methods 0.000 abstract description 4
- 238000005917 acylation reaction Methods 0.000 abstract description 3
- 150000008064 anhydrides Chemical class 0.000 abstract description 3
- 238000013459 approach Methods 0.000 abstract description 3
- 238000006482 condensation reaction Methods 0.000 abstract description 3
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 3
- 241001465754 Metazoa Species 0.000 abstract description 2
- 230000007062 hydrolysis Effects 0.000 abstract description 2
- 238000011160 research Methods 0.000 abstract description 2
- 230000031700 light absorption Effects 0.000 description 16
- 238000010521 absorption reaction Methods 0.000 description 8
- 230000008878 coupling Effects 0.000 description 8
- 238000010168 coupling process Methods 0.000 description 8
- 238000005859 coupling reaction Methods 0.000 description 8
- 102000004169 proteins and genes Human genes 0.000 description 7
- 108090000623 proteins and genes Proteins 0.000 description 7
- 230000000890 antigenic effect Effects 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 208000006550 Mydriasis Diseases 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- NKLPQNGYXWVELD-UHFFFAOYSA-M coomassie brilliant blue Chemical compound [Na+].C1=CC(OCC)=CC=C1NC1=CC=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=C1 NKLPQNGYXWVELD-UHFFFAOYSA-M 0.000 description 2
- 239000006196 drop Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000005375 photometry Methods 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 238000010408 sweeping Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- XQJMXPAEFMWDOZ-UHFFFAOYSA-N 3exo-benzoyloxy-tropane Natural products CN1C(C2)CCC1CC2OC(=O)C1=CC=CC=C1 XQJMXPAEFMWDOZ-UHFFFAOYSA-N 0.000 description 1
- 206010003445 Ascites Diseases 0.000 description 1
- 108010044091 Globulins Proteins 0.000 description 1
- 102000006395 Globulins Human genes 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- 206010020843 Hyperthermia Diseases 0.000 description 1
- 206010022941 Iridocyclitis Diseases 0.000 description 1
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 1
- QQXLDOJGLXJCSE-UHFFFAOYSA-N N-methylnortropinone Natural products C1C(=O)CC2CCC1N2C QQXLDOJGLXJCSE-UHFFFAOYSA-N 0.000 description 1
- QIZDQFOVGFDBKW-DHBOJHSNSA-N Pseudotropine Natural products OC1C[C@@H]2[N+](C)[C@H](C1)CC2 QIZDQFOVGFDBKW-DHBOJHSNSA-N 0.000 description 1
- 208000001431 Psychomotor Agitation Diseases 0.000 description 1
- 206010037211 Psychomotor hyperactivity Diseases 0.000 description 1
- 206010038490 Renal pain Diseases 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- 206010044565 Tremor Diseases 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 201000004612 anterior uveitis Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 230000001886 ciliary effect Effects 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 230000036031 hyperthermia Effects 0.000 description 1
- 230000002163 immunogen Effects 0.000 description 1
- 230000005847 immunogenicity Effects 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 208000001491 myopia Diseases 0.000 description 1
- 230000004379 myopia Effects 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 210000005037 parasympathetic nerve Anatomy 0.000 description 1
- 210000001747 pupil Anatomy 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- CYHOMWAPJJPNMW-JIGDXULJSA-N tropine Chemical compound C1[C@@H](O)C[C@H]2CC[C@@H]1N2C CYHOMWAPJJPNMW-JIGDXULJSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K19/00—Hybrid peptides, i.e. peptides covalently bound to nucleic acids, or non-covalently bound protein-protein complexes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/46—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates
- C07K14/47—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates from mammals
- C07K14/4701—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates from mammals not used
- C07K14/4717—Plasma globulins, lactoglobulin
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- Toxicology (AREA)
- Zoology (AREA)
- Gastroenterology & Hepatology (AREA)
- Peptides Or Proteins (AREA)
Abstract
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Priority Applications (1)
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CN201510802311.4A CN105273075B (zh) | 2015-11-16 | 2015-11-16 | 一种托品酰胺人工抗原的制备方法 |
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CN201510802311.4A CN105273075B (zh) | 2015-11-16 | 2015-11-16 | 一种托品酰胺人工抗原的制备方法 |
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CN105273075A CN105273075A (zh) | 2016-01-27 |
CN105273075B true CN105273075B (zh) | 2018-11-30 |
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CN201510802311.4A Active CN105273075B (zh) | 2015-11-16 | 2015-11-16 | 一种托品酰胺人工抗原的制备方法 |
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Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
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CN106046143A (zh) * | 2016-07-25 | 2016-10-26 | 杭州莱和生物技术有限公司 | 一种苯胺绿人工抗原的制备方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101671345A (zh) * | 2009-09-28 | 2010-03-17 | 桂林医学院 | 一种莪术醇半抗原和人工抗原及其制备方法 |
CN103360487A (zh) * | 2013-07-05 | 2013-10-23 | 杭州博林生物技术有限公司 | 一种丙氧酚人工抗原的制备方法 |
CN104558153A (zh) * | 2014-12-26 | 2015-04-29 | 杭州奥泰生物技术有限公司 | 一种咖啡因人工抗原的制备方法 |
-
2015
- 2015-11-16 CN CN201510802311.4A patent/CN105273075B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101671345A (zh) * | 2009-09-28 | 2010-03-17 | 桂林医学院 | 一种莪术醇半抗原和人工抗原及其制备方法 |
CN103360487A (zh) * | 2013-07-05 | 2013-10-23 | 杭州博林生物技术有限公司 | 一种丙氧酚人工抗原的制备方法 |
CN104558153A (zh) * | 2014-12-26 | 2015-04-29 | 杭州奥泰生物技术有限公司 | 一种咖啡因人工抗原的制备方法 |
Non-Patent Citations (3)
Title |
---|
半抗原的设计、修饰及人工抗原的制备;宋娟,王榕妹;《分析化学评述与进展》;20100831;1211-1218 * |
小分子半抗原抗体制备技术的研究进展;晁博,薛飞群;《中国兽医科学》;20060930;757-761 * |
小分子药物人工抗原的合成与鉴定研究进展;张煜超,王芳芳,李周敏,姚开安,方慧群;《药物分析杂志》;20140630;947-950 * |
Also Published As
Publication number | Publication date |
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CN105273075A (zh) | 2016-01-27 |
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Address after: 310018 550 Yinhai street, Hangzhou economic and Technological Development Zone, Zhejiang Applicant after: Hangzhou Aotai biotechnology Limited by Share Ltd Address before: 310018 550 Yinhai street, Hangzhou economic and Technological Development Zone, Zhejiang Applicant before: Hangzhou Ao Tai Bioisystech Co., Ltd |
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Address after: 310018 Building 5, building 4, building 3, No. 550, Yinhai street, Baiyang street, Hangzhou Economic and Technological Development Zone, Jianggan District, Hangzhou City, Zhejiang Province Patentee after: Hangzhou Aotai biotechnology Limited by Share Ltd Address before: 310018 No. 550, Yinhai street, Hangzhou economic and Technological Development Zone, Zhejiang Patentee before: Hangzhou Aotai biotechnology Limited by Share Ltd |