CN104086496B - A kind of antithrombotic compound, Preparation Method And The Use - Google Patents
A kind of antithrombotic compound, Preparation Method And The Use Download PDFInfo
- Publication number
- CN104086496B CN104086496B CN201410352063.3A CN201410352063A CN104086496B CN 104086496 B CN104086496 B CN 104086496B CN 201410352063 A CN201410352063 A CN 201410352063A CN 104086496 B CN104086496 B CN 104086496B
- Authority
- CN
- China
- Prior art keywords
- compound
- preparation
- acid
- par
- formula
- 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 10
- 150000001875 compounds Chemical class 0.000 title claims description 20
- 239000003146 anticoagulant agent Substances 0.000 title claims description 11
- 230000002785 anti-thrombosis Effects 0.000 title claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims description 3
- 239000002262 Schiff base Substances 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 3
- 150000004753 Schiff bases Chemical class 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- 208000007536 Thrombosis Diseases 0.000 abstract description 13
- 239000003814 drug Substances 0.000 abstract description 10
- 229940098892 Protease-activated receptor-1 antagonist Drugs 0.000 abstract description 5
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 210000001772 blood platelet Anatomy 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 102100037136 Proteinase-activated receptor 1 Human genes 0.000 description 5
- 101710121440 Proteinase-activated receptor 1 Proteins 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 230000000630 rising effect Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 3
- 230000000702 anti-platelet effect Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 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
- 239000000556 agonist Substances 0.000 description 2
- 229940127218 antiplatelet drug Drugs 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
- 239000012267 brine Substances 0.000 description 2
- QNEFNFIKZWUAEQ-UHFFFAOYSA-N carbonic acid;potassium Chemical compound [K].OC(O)=O QNEFNFIKZWUAEQ-UHFFFAOYSA-N 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
- 238000004440 column chromatography Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229960000935 dehydrated alcohol Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 210000002381 plasma Anatomy 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 2
- 238000012360 testing method Methods 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
- 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
- 101000783577 Dendroaspis angusticeps Thrombostatin Proteins 0.000 description 1
- 101000783578 Dendroaspis jamesoni kaimosae Dendroaspin Proteins 0.000 description 1
- 229940123900 Direct thrombin inhibitor Drugs 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
- 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
- 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
- 230000006502 antiplatelets effects Effects 0.000 description 1
- 229960004676 antithrombotic agent Drugs 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000023555 blood coagulation Effects 0.000 description 1
- 230000037396 body weight Effects 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
- 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
- 239000012141 concentrate Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 239000003260 cyclooxygenase 1 inhibitor Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 239000003527 fibrinolytic agent Substances 0.000 description 1
- 108700032141 ganirelix Proteins 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
- 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
- 230000000144 pharmacologic effect Effects 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
- 239000000106 platelet aggregation inhibitor Substances 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
- 239000002994 raw material Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 238000000611 regression analysis 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
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- -1 triazole Schiff bases Chemical class 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (3)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410352063.3A CN104086496B (en) | 2014-07-23 | 2014-07-23 | A kind of antithrombotic compound, Preparation Method And The Use |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410352063.3A CN104086496B (en) | 2014-07-23 | 2014-07-23 | A kind of antithrombotic compound, Preparation Method And The Use |
Publications (2)
Publication Number | Publication Date |
---|---|
CN104086496A CN104086496A (en) | 2014-10-08 |
CN104086496B true CN104086496B (en) | 2015-09-30 |
Family
ID=51634286
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201410352063.3A Active CN104086496B (en) | 2014-07-23 | 2014-07-23 | A kind of antithrombotic compound, Preparation Method And The Use |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN104086496B (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104529928A (en) * | 2015-01-13 | 2015-04-22 | 佛山市赛维斯医药科技有限公司 | One category of oxadiazole sulfoxide compounds, and preparation method and application thereof |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6518254B1 (en) * | 2002-04-11 | 2003-02-11 | Henry Joseph Niemczyk | Ribonucleoside-TRIBOSE |
CN101747322A (en) * | 2010-01-20 | 2010-06-23 | 贵州大学 | Pyridazinone derivatives with 1,2,4-triazole schiff base, preparation method and application thereof |
CN102329273A (en) * | 2011-07-15 | 2012-01-25 | 中国科学院海洋研究所 | Schiff base containing nitrogenous heterocyclic compound and preparation method and application thereof |
CN103739594A (en) * | 2012-10-17 | 2014-04-23 | 南京大学 | Schiff base derivatives containing pyrazine ring and triazole structure and preparation method of the derivatives |
-
2014
- 2014-07-23 CN CN201410352063.3A patent/CN104086496B/en 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 (en) * | 2010-01-20 | 2010-06-23 | 贵州大学 | Pyridazinone derivatives with 1,2,4-triazole schiff base, preparation method and application thereof |
CN102329273A (en) * | 2011-07-15 | 2012-01-25 | 中国科学院海洋研究所 | Schiff base containing nitrogenous heterocyclic compound and preparation method and application thereof |
CN103739594A (en) * | 2012-10-17 | 2014-04-23 | 南京大学 | Schiff base derivatives containing pyrazine ring and triazole structure and preparation method of the derivatives |
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 |
---|---|
CN104086496A (en) | 2014-10-08 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN104072436A (en) | Para-position substituted tetrazole acetophenone compound, preparation method and application | |
CN104072434A (en) | Meta-substituted tetrazole acetophenone as well as preparation method and usage thereof | |
CN104086501A (en) | PAR (Protease Activated Receptor)-1 antagonist as well as preparation method and application of PAR-1 antagonist | |
CN104098520A (en) | Phenyl triazole schiff base compound as well as preparation method and application thereof | |
CN104529927B (en) | One class is containing oxadiazoles sulfoxide compound, the Preparation Method And The Use of halogeno-benzene | |
CN104086503B (en) | PAR-1 antagonist and uses thereof | |
CN104086500B (en) | A kind of PAR-1 antagonist and uses thereof | |
CN104072437A (en) | Disubstituted tetrazole acetophenone compound and preparation method and use thereof | |
CN104072439A (en) | Halogen-substituted four nitrogen azole acetophenone compound,preparation method and application thereof | |
CN104086496B (en) | A kind of antithrombotic compound, Preparation Method And The Use | |
CN104086492B (en) | Antithrombotic compound, Preparation Method And The Use | |
CN104072432A (en) | Compound containing phenyl substituted triazole schiff base structure, as well as preparation method and application thereof | |
CN104140398A (en) | Compound of methyl triazole Schiff base structure, and preparation method and applications of compound | |
CN104072431A (en) | Compound of phenyl triazole Schiff base structure substituted for alkoxy and application | |
CN104086497A (en) | Triazole Schiff base compounds as well as preparation methods and applications of triazole Schiff base compounds | |
CN104086494A (en) | Compounds with terminally-disubstituted methyl triazole Schiff base structures as well as preparation methods and applications of compounds | |
CN104086493A (en) | Compounds with terminally-substituted phenyl triazole Schiff base structures and applications of compounds | |
CN104086498A (en) | Compounds with terminally-substituted triazole Schiff base structures as well as preparation methods and applications of compounds | |
CN104086495A (en) | Compounds with terminally-disubstituted triazole Schiff base structure as well as preparation methods and applications of compounds | |
CN104513212B (en) | Oxadiazoles sulfoxide compound, the Preparation Method And The Use of one class nitrobenzene-containing | |
CN104529930B (en) | One class nitrile group-containing Ben oxadiazole sulfoxide compound, Preparation Method And The Use | |
CN104356059B (en) | Trans cvclohexvl alkyl amide compound containing halogenated pyridyl and purposes | |
CN104496931A (en) | Oxadiazole sulfoxide compound containing amino substituted benzene and preparation method and purposes thereof | |
CN104529860A (en) | Compound containing nitrobenzene and diene fluoro adamantane structure and preparation method thereof | |
CN104496932A (en) | Oxadiazole sulfoxide compound containing alkyl-para-substituted phenyl, preparation method thereof and application thereof |
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: 20170728 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: Xu Xiaohong Inventor before: Zhang Yuanqiang |
|
CB03 | Change of inventor or designer information | ||
TR01 | Transfer of patent right |
Effective date of registration: 20170825 Address after: 063000, Tangshan City Road, North District, Hebei Construction South Road, Shanxi north, 1 floor, 1 gate, No. 301 Patentee after: Xu Xiaohong 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: 20190917 Address after: 272000 East of Yingxiu Road and South of Torch Industrial Park, Jining City, Shandong Province Patentee after: Company limited of Jining Huaneng Pharmaceutical Factory Address before: 063000 Hebei Tangshan City Road North Road Construction South Road Shanxi North Lane 1 Building 1 doors 301 Patentee before: Xu Xiao Hong |
|
TR01 | Transfer of patent right |