CN102293741B - Bromhexine hydrochlorie injection, its preparation method and application - Google Patents
Bromhexine hydrochlorie injection, its preparation method and application Download PDFInfo
- Publication number
- CN102293741B CN102293741B CN 201110246847 CN201110246847A CN102293741B CN 102293741 B CN102293741 B CN 102293741B CN 201110246847 CN201110246847 CN 201110246847 CN 201110246847 A CN201110246847 A CN 201110246847A CN 102293741 B CN102293741 B CN 102293741B
- Authority
- CN
- China
- Prior art keywords
- bisolvon
- injection
- preparation
- glucose
- aqueous solution
- 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.)
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- 238000002347 injection Methods 0.000 title claims abstract description 43
- 239000007924 injection Substances 0.000 title claims abstract description 43
- 238000002360 preparation method Methods 0.000 title claims abstract description 43
- 229960003870 bromhexine Drugs 0.000 title claims abstract description 8
- OJGDCBLYJGHCIH-UHFFFAOYSA-N bromhexine Chemical compound C1CCCCC1N(C)CC1=CC(Br)=CC(Br)=C1N OJGDCBLYJGHCIH-UHFFFAOYSA-N 0.000 title claims abstract description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title abstract 6
- 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 claims abstract description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 42
- 239000008103 glucose Substances 0.000 claims abstract description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000000034 method Methods 0.000 claims abstract description 28
- 230000008569 process Effects 0.000 claims abstract description 20
- UCDKONUHZNTQPY-UHFFFAOYSA-N bromhexine hydrochloride Chemical compound Cl.C1CCCCC1N(C)CC1=CC(Br)=CC(Br)=C1N UCDKONUHZNTQPY-UHFFFAOYSA-N 0.000 claims description 100
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 20
- 239000008215 water for injection Substances 0.000 claims description 16
- 239000007864 aqueous solution Substances 0.000 claims description 15
- 238000003756 stirring Methods 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 238000001914 filtration Methods 0.000 claims description 10
- 239000003172 expectorant agent Substances 0.000 claims description 7
- 230000003419 expectorant effect Effects 0.000 claims description 7
- YENKYLWBLTUEQL-UHFFFAOYSA-N 2-bromohexanoic acid hydrochloride Chemical compound BrC(C(=O)O)CCCC.Cl YENKYLWBLTUEQL-UHFFFAOYSA-N 0.000 claims description 6
- 238000005262 decarbonization Methods 0.000 claims description 5
- 238000012856 packing Methods 0.000 claims description 5
- 238000010521 absorption reaction Methods 0.000 claims description 4
- 239000000706 filtrate Substances 0.000 claims description 4
- 239000012982 microporous membrane Substances 0.000 claims description 4
- 238000001179 sorption measurement Methods 0.000 claims description 4
- 230000001954 sterilising effect Effects 0.000 claims description 4
- 238000004659 sterilization and disinfection Methods 0.000 claims description 3
- 238000001802 infusion Methods 0.000 claims description 2
- 239000000243 solution Substances 0.000 abstract description 25
- 239000003814 drug Substances 0.000 abstract description 10
- 239000007788 liquid Substances 0.000 abstract description 8
- 229940079593 drug Drugs 0.000 abstract description 4
- 230000003115 biocidal effect Effects 0.000 abstract description 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 abstract description 2
- 230000033228 biological regulation Effects 0.000 abstract description 2
- 206010067484 Adverse reaction Diseases 0.000 abstract 1
- 230000006838 adverse reaction Effects 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 238000009210 therapy by ultrasound Methods 0.000 abstract 1
- 229940090044 injection Drugs 0.000 description 31
- 238000001556 precipitation Methods 0.000 description 13
- 229940093181 glucose injection Drugs 0.000 description 12
- 229960002335 bromhexine hydrochloride Drugs 0.000 description 10
- YRSGDLIATOURQO-UHFFFAOYSA-N ethyl 4-acetyl-5-oxohexanoate Chemical compound CCOC(=O)CCC(C(C)=O)C(C)=O YRSGDLIATOURQO-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000012360 testing method Methods 0.000 description 7
- 238000005303 weighing Methods 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 5
- 206010001598 Alcohol intolerance Diseases 0.000 description 4
- 206010036790 Productive cough Diseases 0.000 description 4
- 239000003242 anti bacterial agent Substances 0.000 description 4
- 229940088710 antibiotic agent Drugs 0.000 description 4
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- 238000002474 experimental method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 230000008859 change Effects 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 206010006451 bronchitis Diseases 0.000 description 2
- 229960004682 cefoperazone Drugs 0.000 description 2
- GCFBRXLSHGKWDP-XCGNWRKASA-N cefoperazone Chemical compound O=C1C(=O)N(CC)CCN1C(=O)N[C@H](C=1C=CC(O)=CC=1)C(=O)N[C@@H]1C(=O)N2C(C(O)=O)=C(CSC=3N(N=NN=3)C)CS[C@@H]21 GCFBRXLSHGKWDP-XCGNWRKASA-N 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 description 1
- 208000004476 Acute Coronary Syndrome Diseases 0.000 description 1
- 206010002199 Anaphylactic shock Diseases 0.000 description 1
- 235000005749 Anthriscus sylvestris Nutrition 0.000 description 1
- 206010006458 Bronchitis chronic Diseases 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 208000000059 Dyspnea Diseases 0.000 description 1
- 206010013975 Dyspnoeas Diseases 0.000 description 1
- 206010014561 Emphysema Diseases 0.000 description 1
- 208000004547 Hallucinations Diseases 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 208000008454 Hyperhidrosis Diseases 0.000 description 1
- 206010062717 Increased upper airway secretion Diseases 0.000 description 1
- 240000004836 Justicia adhatoda Species 0.000 description 1
- YIICVSCAKJMMDJ-UHFFFAOYSA-N L-vasicine Natural products C1=CC=C2N=C3C(O)CCN3CC2=C1 YIICVSCAKJMMDJ-UHFFFAOYSA-N 0.000 description 1
- 208000009481 Laryngeal Edema Diseases 0.000 description 1
- 206010023845 Laryngeal oedema Diseases 0.000 description 1
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- YIICVSCAKJMMDJ-SNVBAGLBSA-N Peganine Chemical compound C1=CC=C2N=C3[C@H](O)CCN3CC2=C1 YIICVSCAKJMMDJ-SNVBAGLBSA-N 0.000 description 1
- YIICVSCAKJMMDJ-JTQLQIEISA-N Peganine Natural products C1=CC=C2N=C3[C@@H](O)CCN3CC2=C1 YIICVSCAKJMMDJ-JTQLQIEISA-N 0.000 description 1
- 208000018569 Respiratory Tract disease Diseases 0.000 description 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
- 206010041349 Somnolence Diseases 0.000 description 1
- 208000035286 Spontaneous Remission Diseases 0.000 description 1
- HJLSLZFTEKNLFI-UHFFFAOYSA-N Tinidazole Chemical compound CCS(=O)(=O)CCN1C(C)=NC=C1[N+]([O-])=O HJLSLZFTEKNLFI-UHFFFAOYSA-N 0.000 description 1
- JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 1
- 208000003443 Unconsciousness Diseases 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- ADNBOFQFSCPWBA-RJMJUYIDSA-N [Na].O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O Chemical compound [Na].O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O ADNBOFQFSCPWBA-RJMJUYIDSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- -1 biochemistry Substances 0.000 description 1
- 201000009267 bronchiectasis Diseases 0.000 description 1
- 229960004261 cefotaxime Drugs 0.000 description 1
- GPRBEKHLDVQUJE-VINNURBNSA-N cefotaxime Chemical compound N([C@@H]1C(N2C(=C(COC(C)=O)CS[C@@H]21)C(O)=O)=O)C(=O)/C(=N/OC)C1=CSC(N)=N1 GPRBEKHLDVQUJE-VINNURBNSA-N 0.000 description 1
- 229960000479 ceftriaxone sodium Drugs 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 1
- 229940097572 chloromycetin Drugs 0.000 description 1
- 208000007451 chronic bronchitis Diseases 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- FDRNWTJTHBSPMW-GNXCPKRQSA-L disodium;(6r,7r)-7-[[(2e)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(2-methyl-6-oxido-5-oxo-1,2,4-triazin-3-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound [Na+].[Na+].S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)/C(=N/OC)C=2N=C(N)SC=2)CC=1CSC1=NC(=O)C([O-])=NN1C FDRNWTJTHBSPMW-GNXCPKRQSA-L 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000004438 eyesight Effects 0.000 description 1
- PLHJDBGFXBMTGZ-WEVVVXLNSA-N furazolidone Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)OCC1 PLHJDBGFXBMTGZ-WEVVVXLNSA-N 0.000 description 1
- 229960001625 furazolidone Drugs 0.000 description 1
- 229960004580 glibenclamide Drugs 0.000 description 1
- ZNNLBTZKUZBEKO-UHFFFAOYSA-N glyburide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZNNLBTZKUZBEKO-UHFFFAOYSA-N 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000037315 hyperhidrosis Effects 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 206010022437 insomnia Diseases 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229960004125 ketoconazole Drugs 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229960000282 metronidazole Drugs 0.000 description 1
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 1
- 229940066491 mucolytics Drugs 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- ICFJFFQQTFMIBG-UHFFFAOYSA-N phenformin Chemical compound NC(=N)NC(=N)NCCC1=CC=CC=C1 ICFJFFQQTFMIBG-UHFFFAOYSA-N 0.000 description 1
- 229960003243 phenformin Drugs 0.000 description 1
- 208000026435 phlegm Diseases 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 208000024794 sputum Diseases 0.000 description 1
- 210000003802 sputum Anatomy 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 229960005053 tinidazole Drugs 0.000 description 1
- 229960005371 tolbutamide Drugs 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
Landscapes
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (8)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 201110246847 CN102293741B (en) | 2011-08-24 | 2011-08-24 | Bromhexine hydrochlorie injection, its preparation method and application |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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CN 201110246847 CN102293741B (en) | 2011-08-24 | 2011-08-24 | Bromhexine hydrochlorie injection, its preparation method and application |
Publications (2)
Publication Number | Publication Date |
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CN102293741A CN102293741A (en) | 2011-12-28 |
CN102293741B true CN102293741B (en) | 2013-02-20 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CN 201110246847 Active CN102293741B (en) | 2011-08-24 | 2011-08-24 | Bromhexine hydrochlorie injection, its preparation method and application |
Country Status (1)
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CN (1) | CN102293741B (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103976945B8 (en) * | 2014-06-04 | 2016-12-21 | 回音必集团(江西)东亚制药有限公司 | A kind of Bisolvon glucose injection |
CN104434786B (en) * | 2014-12-09 | 2017-04-12 | 河北仁合益康药业有限公司 | Stable bromhexine hydrochloride sodium chloride injection composition |
CN105534889B (en) * | 2016-01-07 | 2018-11-02 | 河北仁合益康药业有限公司 | A kind of sucking bromhexine hydrochloride liquid composite and preparation method thereof |
CN111714477B (en) * | 2020-07-23 | 2021-06-15 | 山东迅达康兽药有限公司 | Phlegm eliminating composition and preparation method of oral liquid thereof |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH085784B2 (en) * | 1987-06-17 | 1996-01-24 | 興和株式会社 | Syrup |
AU2002366588A1 (en) * | 2001-12-13 | 2003-06-23 | Council Of Scientific And Industrial Research | Bioavailability enhancing activity of zingiber officinale linn and its extracts/fractions thereof |
CN1184963C (en) * | 2002-09-10 | 2005-01-19 | 张嵩 | Bromhexine hydrochloride injection and its preparation method |
CN1259041C (en) * | 2004-02-05 | 2006-06-14 | 马小歧 | Bromhexine Hydrochloride aseptic freeze-drying formulation for injection and its preparation method |
DE102004023930A1 (en) * | 2004-05-12 | 2005-12-08 | Boehringer Ingelheim Vetmedica Gmbh | Fast-dissolving granules of bromhexine / bromhexine hydrochloride, process for its preparation and its use |
CN1634589A (en) * | 2004-10-04 | 2005-07-06 | 杨喜鸿 | Injection using invert sugar water solution as carrier |
CN100409835C (en) * | 2007-04-06 | 2008-08-13 | 张嵩 | Composition and great volume injection containing bromhexine salt and the injection preparing process |
-
2011
- 2011-08-24 CN CN 201110246847 patent/CN102293741B/en active Active
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Publication number | Publication date |
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CN102293741A (en) | 2011-12-28 |
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SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
C53 | Correction of patent for invention or patent application | ||
CB03 | Change of inventor or designer information |
Inventor after: Zhang Kai Inventor after: Du Yumin Inventor after: Xue Na Inventor after: Han Fengnian Inventor after: Ma Xuwei Inventor before: Zhang Kai Inventor before: Du Yumin Inventor before: Xue Na Inventor before: Han Fengnian Inventor before: Ma Xuwei |
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EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20111228 Assignee: Shijiazhuang Sinopharm Co., Ltd. Assignor: Shijiazhuang Dongfang Pharmaceutical Co., Ltd. Contract record no.: 2014130000104 Denomination of invention: Bromhexine hydrochlorie injection, its preparation method and application Granted publication date: 20130220 License type: Common License Record date: 20140625 |
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LICC | Enforcement, change and cancellation of record of contracts on the licence for exploitation of a patent or utility model | ||
C41 | Transfer of patent application or patent right or utility model | ||
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Effective date of registration: 20151225 Address after: Hebei province Shijiazhuang City Xinshi road 050000 No. 375 Patentee after: Shijiazhuang Hankang Biology Chemistry Medicine Co., Ltd. Address before: 050017 No. 17 battalion Avenue, Shijiazhuang, Hebei Patentee before: Shijiazhuang Dongfang Pharmaceutical Co., Ltd. |
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CI01 | Correction of invention patent gazette |
Correction item: Assignee of record for patent exploitation license contracts Correct: Shijiazhuang No.4 Pharmaceutical Co., Ltd. False: Shijiazhuang Sinopharm Co., Ltd. Number: 35 Volume: 30 |
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ERR | Gazette correction | ||
EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20111228 Assignee: Shijiazhuang No.4 Pharmaceutical Co., Ltd. Assignor: Shijiazhuang Hankang Biology Chemistry Medicine Co., Ltd. Contract record no.: 2018130000012 Denomination of invention: Bromhexine hydrochlorie injection, its preparation method and application Granted publication date: 20130220 License type: Common License Record date: 20190104 |
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EE01 | Entry into force of recordation of patent licensing contract |