CN104086495B - 末端双取代的三唑希夫碱结构化合物、其制备方法和用途 - Google Patents
末端双取代的三唑希夫碱结构化合物、其制备方法和用途 Download PDFInfo
- Publication number
- CN104086495B CN104086495B CN201410352062.9A CN201410352062A CN104086495B CN 104086495 B CN104086495 B CN 104086495B CN 201410352062 A CN201410352062 A CN 201410352062A CN 104086495 B CN104086495 B CN 104086495B
- Authority
- CN
- China
- Prior art keywords
- compound
- preparation
- schiff bases
- present
- triazole schiff
- 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.)
- Active
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 150000001875 compounds Chemical class 0.000 title claims description 26
- 239000002262 Schiff base Substances 0.000 title abstract description 5
- -1 triazole schiff bases Chemical class 0.000 title abstract description 4
- 239000003146 anticoagulant agent Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 230000002785 anti-thrombosis Effects 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 208000007536 Thrombosis Diseases 0.000 abstract description 15
- 239000003814 drug Substances 0.000 abstract description 9
- 229940098892 Protease-activated receptor-1 antagonist Drugs 0.000 abstract description 5
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 2
- 210000001772 blood platelet Anatomy 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 102100037136 Proteinase-activated receptor 1 Human genes 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 101710121440 Proteinase-activated receptor 1 Proteins 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 230000000702 anti-platelet effect Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 208000032843 Hemorrhage Diseases 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 108010070519 PAR-1 Receptor Proteins 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 102000002020 Protease-activated receptors Human genes 0.000 description 2
- 108050009310 Protease-activated receptors Proteins 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 102000003790 Thrombin receptors Human genes 0.000 description 2
- 108090000166 Thrombin receptors Proteins 0.000 description 2
- 208000035896 Twin-reversed arterial perfusion sequence Diseases 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000000556 agonist Substances 0.000 description 2
- 208000034158 bleeding Diseases 0.000 description 2
- 230000000740 bleeding effect Effects 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 210000002381 plasma Anatomy 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OVBICQMTCPFEBS-SATRDZAXSA-N (2s)-1-[(2s)-2-[[(2s)-2-[[(2r)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-acetamido-3-naphthalen-2-ylpropanoyl]amino]-3-(4-chlorophenyl)propanoyl]amino]-3-pyridin-3-ylpropanoyl]amino]-3-hydroxypropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-6-[bi Chemical compound CC(O)=O.CC(O)=O.C([C@@H](C(=O)N[C@H](CCCCN=C(NCC)NCC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN=C(NCC)NCC)C(=O)N1[C@@H](CCC1)C(=O)N[C@H](C)C(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](CC=1C=NC=CC=1)NC(=O)[C@@H](CC=1C=CC(Cl)=CC=1)NC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(C)=O)C1=CC=C(O)C=C1 OVBICQMTCPFEBS-SATRDZAXSA-N 0.000 description 1
- GMVPRGQOIOIIMI-UHFFFAOYSA-N (8R,11R,12R,13E,15S)-11,15-Dihydroxy-9-oxo-13-prostenoic acid Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CCCCCCC(O)=O GMVPRGQOIOIIMI-UHFFFAOYSA-N 0.000 description 1
- DQXKOHDUMJLXKH-PHEQNACWSA-N (e)-n-[2-[2-[[(e)-oct-2-enoyl]amino]ethyldisulfanyl]ethyl]oct-2-enamide Chemical compound CCCCC\C=C\C(=O)NCCSSCCNC(=O)\C=C\CCCCC DQXKOHDUMJLXKH-PHEQNACWSA-N 0.000 description 1
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
- 208000004476 Acute Coronary Syndrome Diseases 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 239000005552 B01AC04 - Clopidogrel Substances 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 229940123900 Direct thrombin inhibitor Drugs 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 102000003886 Glycoproteins Human genes 0.000 description 1
- 108090000288 Glycoproteins Proteins 0.000 description 1
- 239000007995 HEPES buffer Substances 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 102000032626 PAR-1 Receptor Human genes 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 206010050661 Platelet aggregation inhibition Diseases 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 102000007466 Purinergic P2 Receptors Human genes 0.000 description 1
- 108010085249 Purinergic P2 Receptors Proteins 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- 150000004753 Schiff bases Chemical class 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
- 108090000190 Thrombin Proteins 0.000 description 1
- 229930003448 Vitamin K Natural products 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229960000711 alprostadil Drugs 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000010100 anticoagulation Effects 0.000 description 1
- 229940127218 antiplatelet drug Drugs 0.000 description 1
- 230000006502 antiplatelets effects Effects 0.000 description 1
- 229960004676 antithrombotic agent Drugs 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000023555 blood coagulation Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- QNEFNFIKZWUAEQ-UHFFFAOYSA-N carbonic acid;potassium Chemical compound [K].OC(O)=O QNEFNFIKZWUAEQ-UHFFFAOYSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- GKTWGGQPFAXNFI-HNNXBMFYSA-N clopidogrel Chemical compound C1([C@H](N2CC=3C=CSC=3CC2)C(=O)OC)=CC=CC=C1Cl GKTWGGQPFAXNFI-HNNXBMFYSA-N 0.000 description 1
- 229960003009 clopidogrel Drugs 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003260 cyclooxygenase 1 inhibitor Substances 0.000 description 1
- 229960000935 dehydrated alcohol Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003527 fibrinolytic agent Substances 0.000 description 1
- 108700032141 ganirelix Proteins 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 230000012447 hatching Effects 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 description 1
- 235000019419 proteases Nutrition 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000611 regression analysis Methods 0.000 description 1
- 230000000452 restraining effect Effects 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 229960004072 thrombin Drugs 0.000 description 1
- 239000003868 thrombin inhibitor Substances 0.000 description 1
- 230000001732 thrombotic effect Effects 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 235000019168 vitamin K Nutrition 0.000 description 1
- 239000011712 vitamin K Substances 0.000 description 1
- 150000003721 vitamin K derivatives Chemical class 0.000 description 1
- 229940046010 vitamin k Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/12—Oxygen or sulfur atoms
Abstract
Description
化合物 | 血小板凝聚的抑制 IC50 (nM) |
化合物I-1 | 1.7 |
化合物I-2 | 3.9 |
化合物I-3 | 5.1 |
化合物I-4 | 3.7 |
Claims (3)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410352062.9A CN104086495B (zh) | 2014-07-23 | 2014-07-23 | 末端双取代的三唑希夫碱结构化合物、其制备方法和用途 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410352062.9A CN104086495B (zh) | 2014-07-23 | 2014-07-23 | 末端双取代的三唑希夫碱结构化合物、其制备方法和用途 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN104086495A CN104086495A (zh) | 2014-10-08 |
CN104086495B true CN104086495B (zh) | 2015-09-09 |
Family
ID=51634285
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201410352062.9A Active CN104086495B (zh) | 2014-07-23 | 2014-07-23 | 末端双取代的三唑希夫碱结构化合物、其制备方法和用途 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN104086495B (zh) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104529928A (zh) * | 2015-01-13 | 2015-04-22 | 佛山市赛维斯医药科技有限公司 | 一类恶二唑亚砜化合物、其制备方法和用途 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6518254B1 (en) * | 2002-04-11 | 2003-02-11 | Henry Joseph Niemczyk | Ribonucleoside-TRIBOSE |
CN101747322A (zh) * | 2010-01-20 | 2010-06-23 | 贵州大学 | 含1,2,4-三唑席夫碱哒嗪酮类衍生物及其制备方法和用途 |
CN102329273A (zh) * | 2011-07-15 | 2012-01-25 | 中国科学院海洋研究所 | 一种含席夫碱类氮杂环化合物及其制备和应用 |
CN103739594A (zh) * | 2012-10-17 | 2014-04-23 | 南京大学 | 一类含吡嗪环和三氮唑结构的席夫碱类衍生物及其制法 |
-
2014
- 2014-07-23 CN CN201410352062.9A patent/CN104086495B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6518254B1 (en) * | 2002-04-11 | 2003-02-11 | Henry Joseph Niemczyk | Ribonucleoside-TRIBOSE |
CN101747322A (zh) * | 2010-01-20 | 2010-06-23 | 贵州大学 | 含1,2,4-三唑席夫碱哒嗪酮类衍生物及其制备方法和用途 |
CN102329273A (zh) * | 2011-07-15 | 2012-01-25 | 中国科学院海洋研究所 | 一种含席夫碱类氮杂环化合物及其制备和应用 |
CN103739594A (zh) * | 2012-10-17 | 2014-04-23 | 南京大学 | 一类含吡嗪环和三氮唑结构的席夫碱类衍生物及其制法 |
Non-Patent Citations (2)
Title |
---|
Synthesis, spectral characterization, in vitro antibacterial, antifungal and cytotoxic activities of Co (II), Ni (II) and Cu (II) complexes with 1, 2, 4-triazole Schiff bases;Bagihalli G B, Avaji P G, Patil S A, et al.;《European journal of medicinal chemistry》;20080229;第43卷(第12期);2639-2649 * |
Thrombin receptor (protease activated receptor-1) antagonists as potent antithrombotic agents with strong antiplatelet effects;Chackalamannil S.;《Journal of medicinal chemistry》;20060831;第49卷(第18期);5389-5403 * |
Also Published As
Publication number | Publication date |
---|---|
CN104086495A (zh) | 2014-10-08 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN104072436B (zh) | 对位取代的四氮唑苯乙酮化合物、其制备方法和用途 | |
CN104098520B (zh) | 苯基三唑希夫碱类化合物、其制备方法和用途 | |
CN104072434B (zh) | 间位取代的四氮唑苯乙酮化合物、其制备方法和用途 | |
CN104529927A (zh) | 一类含卤代苯的恶二唑亚砜化合物、其制备方法和用途 | |
CN104072438B (zh) | 二烷氧代四氮唑苯乙酮化合物、其制备方法和用途 | |
CN104086503B (zh) | Par-1拮抗剂及其用途 | |
CN104072437B (zh) | 双取代的四氮唑苯乙酮化合物、其制备方法和用途 | |
CN104072439B (zh) | 卤素取代的四氮唑苯乙酮化合物、其制备方法和用途 | |
CN104086500B (zh) | 一种par-1拮抗剂及其用途 | |
CN104086495B (zh) | 末端双取代的三唑希夫碱结构化合物、其制备方法和用途 | |
CN104086494B (zh) | 末端双取代的甲基三唑希夫碱结构化合物、其制备方法和用途 | |
CN104140398B (zh) | 甲基三唑希夫碱类结构的化合物、其制备方法和用途 | |
CN104086497B (zh) | 三唑希夫碱类化合物、其制备方法和用途 | |
CN104086498B (zh) | 末端取代的三唑希夫碱类结构的化合物、其制备方法和用途 | |
CN104072432B (zh) | 含苯基取代三唑希夫碱类结构的化合物、其制备方法和用途 | |
CN104072431B (zh) | 烷氧基取代的苯基三唑希夫碱结构的化合物及用途 | |
CN104086496B (zh) | 一种抗血栓化合物、其制备方法和用途 | |
CN104086502B (zh) | 卤代四氮唑苯乙酮化合物、其制备方法和用途 | |
CN104072435B (zh) | 双烷基取代的四氮唑苯乙酮化合物和用途 | |
CN104086493A (zh) | 末端取代的苯基三唑希夫碱结构的化合物及其用途 | |
CN104513212B (zh) | 一类含硝基苯的恶二唑亚砜化合物、其制备方法和用途 | |
CN104356059A (zh) | 含卤代吡啶基的反式环己烷酰胺类化合物及用途 | |
CN104496931A (zh) | 含胺基取代苯的恶二唑亚砜化合物、其制备方法和用途 | |
CN104496932A (zh) | 一类含胺基对位取代苯的恶二唑亚砜化合物、其制备方法和用途 | |
CN104529928A (zh) | 一类恶二唑亚砜化合物、其制备方法和用途 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20170803 Address after: 510640 Guangdong City, Tianhe District Province, No. five, road, public education building, unit 371-1, unit 2401 Patentee after: Guangdong Gaohang Intellectual Property Operation Co., Ltd. Address before: 528000 Guangdong, Foshan District, Pu Lan Road, the first floor of the first floor, No. 5, Chancheng Patentee before: Zhang Yuanqiang |
|
CB03 | Change of inventor or designer information |
Inventor after: Wang Rui Inventor before: Zhang Yuanqiang |
|
CB03 | Change of inventor or designer information | ||
TR01 | Transfer of patent right |
Effective date of registration: 20170822 Address after: 132000 247-2-33 street, Changyi District, Jilin, Jilin, Sichuan Patentee after: Wang Rui Address before: 510640 Guangdong City, Tianhe District Province, No. five, road, public education building, unit 371-1, unit 2401 Patentee before: Guangdong Gaohang Intellectual Property Operation Co., Ltd. |
|
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20180621 Address after: 226500 No. 999 Wanshou South Road, Chengnan street, Rugao City, Nantong, Jiangsu (room 3A08-26, 8 building, Rugao hi tech Zone) Patentee after: Jiangsu hundred sword Pharmaceutical Technology Co., Ltd. Address before: 132000 247-2-33, Sichuan street, Changyi District, Jilin, Jilin. Patentee before: Wang Rui |
|
TR01 | Transfer of patent right |