CN104817523A - 一种治疗胃病的药物盐酸雷尼替丁化合物及其制备方法 - Google Patents
一种治疗胃病的药物盐酸雷尼替丁化合物及其制备方法 Download PDFInfo
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- CN104817523A CN104817523A CN201510273209.XA CN201510273209A CN104817523A CN 104817523 A CN104817523 A CN 104817523A CN 201510273209 A CN201510273209 A CN 201510273209A CN 104817523 A CN104817523 A CN 104817523A
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- ranitidine hydrochloride
- hydrochloride compound
- acetone
- compound
- compound according
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- 229960001520 ranitidine hydrochloride Drugs 0.000 title claims abstract description 79
- -1 ranitidine hydrochloride compound Chemical class 0.000 title claims abstract description 41
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- 239000003814 drug Substances 0.000 title claims abstract description 14
- 210000002784 stomach Anatomy 0.000 title claims abstract description 8
- 229940079593 drug Drugs 0.000 title abstract description 3
- GGWBHVILAJZWKJ-KJEVSKRMSA-N ranitidine hydrochloride Chemical compound [H+].[Cl-].[O-][N+](=O)\C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 GGWBHVILAJZWKJ-KJEVSKRMSA-N 0.000 claims abstract description 41
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 8
- 229910017488 Cu K Inorganic materials 0.000 claims abstract description 5
- 229910017541 Cu-K Inorganic materials 0.000 claims abstract description 5
- 230000005260 alpha ray Effects 0.000 claims abstract description 5
- 238000005259 measurement Methods 0.000 claims abstract description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 48
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- 238000003756 stirring Methods 0.000 claims description 17
- 239000012046 mixed solvent Substances 0.000 claims description 15
- JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 9
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-Lutidine Substances CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims description 7
- 238000001816 cooling Methods 0.000 claims description 5
- 238000004090 dissolution Methods 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 239000013078 crystal Substances 0.000 abstract description 8
- 238000002474 experimental method Methods 0.000 abstract description 4
- 238000010521 absorption reaction Methods 0.000 description 10
- 238000002425 crystallisation Methods 0.000 description 9
- 238000012360 testing method Methods 0.000 description 8
- 230000008025 crystallization Effects 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 238000012552 review Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 238000004806 packaging method and process Methods 0.000 description 4
- 238000005070 sampling Methods 0.000 description 4
- 238000007789 sealing Methods 0.000 description 4
- 238000004088 simulation Methods 0.000 description 4
- VNFPBHJOKIVQEB-UHFFFAOYSA-N clotrimazole Chemical compound ClC1=CC=CC=C1C(N1C=NC=C1)(C=1C=CC=CC=1)C1=CC=CC=C1 VNFPBHJOKIVQEB-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000005286 illumination Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 108010079943 Pentagastrin Proteins 0.000 description 2
- 230000001133 acceleration Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 208000000718 duodenal ulcer Diseases 0.000 description 2
- 230000027119 gastric acid secretion Effects 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- ANRIQLNBZQLTFV-DZUOILHNSA-N pentagastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1[C]2C=CC=CC2=NC=1)NC(=O)CCNC(=O)OC(C)(C)C)CCSC)C(N)=O)C1=CC=CC=C1 ANRIQLNBZQLTFV-DZUOILHNSA-N 0.000 description 2
- 229960000444 pentagastrin Drugs 0.000 description 2
- 229940002612 prodrug Drugs 0.000 description 2
- 239000000651 prodrug Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010583 slow cooling Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical class [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102100021022 Gastrin Human genes 0.000 description 1
- 108010052343 Gastrins Proteins 0.000 description 1
- 208000008469 Peptic Ulcer Diseases 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 229940069428 antacid Drugs 0.000 description 1
- 239000003159 antacid agent Substances 0.000 description 1
- 230000001458 anti-acid effect Effects 0.000 description 1
- 229950002342 bisfentidine Drugs 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- AOXOCDRNSPFDPE-UKEONUMOSA-N chembl413654 Chemical compound C([C@H](C(=O)NCC(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](C)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)CNC(=O)[C@@H](N)CCC(O)=O)C1=CC=C(O)C=C1 AOXOCDRNSPFDPE-UKEONUMOSA-N 0.000 description 1
- 229940000406 drug candidate Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- FXJAOWANXXJWGJ-UHFFFAOYSA-N n-[4-(2-methyl-1h-imidazol-5-yl)phenyl]-n'-propan-2-ylmethanimidamide Chemical compound C1=CC(NC=NC(C)C)=CC=C1C1=CN=C(C)N1 FXJAOWANXXJWGJ-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
Abstract
Description
Claims (8)
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610807242.0A CN106397374A (zh) | 2015-05-26 | 2015-05-26 | 一种制备治疗胃病的药物盐酸雷尼替丁化合物的方法 |
CN201610823211.4A CN106432148B (zh) | 2015-05-26 | 2015-05-26 | 一种治疗胃病的药物盐酸雷尼替丁化合物的制备方法 |
CN201610823327.8A CN106432149B (zh) | 2015-05-26 | 2015-05-26 | 一种制备治疗胃病的药物盐酸雷尼替丁化合物的方法 |
CN201510273209.XA CN104817523B (zh) | 2015-05-26 | 2015-05-26 | 一种治疗胃病的药物盐酸雷尼替丁化合物及其制备方法 |
CN201610823158.8A CN106432147B (zh) | 2015-05-26 | 2015-05-26 | 一种制备治疗胃病的药物盐酸雷尼替丁化合物的方法 |
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CN201510273209.XA CN104817523B (zh) | 2015-05-26 | 2015-05-26 | 一种治疗胃病的药物盐酸雷尼替丁化合物及其制备方法 |
Related Child Applications (4)
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CN201610823211.4A Division CN106432148B (zh) | 2015-05-26 | 2015-05-26 | 一种治疗胃病的药物盐酸雷尼替丁化合物的制备方法 |
CN201610807242.0A Division CN106397374A (zh) | 2015-05-26 | 2015-05-26 | 一种制备治疗胃病的药物盐酸雷尼替丁化合物的方法 |
CN201610823158.8A Division CN106432147B (zh) | 2015-05-26 | 2015-05-26 | 一种制备治疗胃病的药物盐酸雷尼替丁化合物的方法 |
CN201610823327.8A Division CN106432149B (zh) | 2015-05-26 | 2015-05-26 | 一种制备治疗胃病的药物盐酸雷尼替丁化合物的方法 |
Publications (2)
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CN104817523A true CN104817523A (zh) | 2015-08-05 |
CN104817523B CN104817523B (zh) | 2016-11-09 |
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CN201610807242.0A Withdrawn CN106397374A (zh) | 2015-05-26 | 2015-05-26 | 一种制备治疗胃病的药物盐酸雷尼替丁化合物的方法 |
CN201510273209.XA Active CN104817523B (zh) | 2015-05-26 | 2015-05-26 | 一种治疗胃病的药物盐酸雷尼替丁化合物及其制备方法 |
CN201610823158.8A Active CN106432147B (zh) | 2015-05-26 | 2015-05-26 | 一种制备治疗胃病的药物盐酸雷尼替丁化合物的方法 |
CN201610823211.4A Active CN106432148B (zh) | 2015-05-26 | 2015-05-26 | 一种治疗胃病的药物盐酸雷尼替丁化合物的制备方法 |
CN201610823327.8A Active CN106432149B (zh) | 2015-05-26 | 2015-05-26 | 一种制备治疗胃病的药物盐酸雷尼替丁化合物的方法 |
Family Applications Before (1)
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CN201610807242.0A Withdrawn CN106397374A (zh) | 2015-05-26 | 2015-05-26 | 一种制备治疗胃病的药物盐酸雷尼替丁化合物的方法 |
Family Applications After (3)
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CN201610823158.8A Active CN106432147B (zh) | 2015-05-26 | 2015-05-26 | 一种制备治疗胃病的药物盐酸雷尼替丁化合物的方法 |
CN201610823211.4A Active CN106432148B (zh) | 2015-05-26 | 2015-05-26 | 一种治疗胃病的药物盐酸雷尼替丁化合物的制备方法 |
CN201610823327.8A Active CN106432149B (zh) | 2015-05-26 | 2015-05-26 | 一种制备治疗胃病的药物盐酸雷尼替丁化合物的方法 |
Country Status (1)
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CN (5) | CN106397374A (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105055396A (zh) * | 2015-09-17 | 2015-11-18 | 青岛华之草医药科技有限公司 | 一种治疗胃病的药物盐酸雷尼替丁组合物冻干粉针剂 |
CN107382922A (zh) * | 2017-08-03 | 2017-11-24 | 江苏汉斯通药业有限公司 | 高透光度盐酸雷尼替丁的制备方法 |
Citations (5)
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US4521431A (en) * | 1980-10-01 | 1985-06-04 | Glaxo Group Limited | Aminoalkyl furan derivative |
CN1098720A (zh) * | 1991-12-20 | 1995-02-15 | 多坎化学有限公司 | 晶形1呋喃硝胺氢氯化物的制备 |
US5523423A (en) * | 1994-04-08 | 1996-06-04 | Acic (Canada) Inc. | Form of form 1 Ranitidine |
US5621120A (en) * | 1994-05-13 | 1997-04-15 | Ranbaxy Laboratories Limited | Process for the manufacture of form 1 ranitidine hydrochloride |
WO1999065890A1 (en) * | 1998-06-17 | 1999-12-23 | Russinsky Limited | Ranitidine adduct |
Family Cites Families (7)
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GR852557B (zh) * | 1985-10-23 | 1985-11-27 | Chemica Farmakeutiki Viomihani | |
KR0152469B1 (ko) * | 1995-07-13 | 1998-10-15 | 이승웅 | 아민염산염을 이용한 라니티딘 염산염의 제조방법 |
AU1972097A (en) * | 1996-03-25 | 1997-10-17 | Hoechst Marion Roussel, Inc. | Process for the preparation of form 1 ranitidine hydrochloride |
US20020151729A1 (en) * | 1997-02-26 | 2002-10-17 | Cheng Wen J. | Novel process for the preparation of form 1 ranitidine hydrochloride |
CN1315818C (zh) * | 2005-07-11 | 2007-05-16 | 石药集团中诺药业(石家庄)有限公司 | 一种雷尼替丁碱及其盐酸盐的合成方法 |
CN102010389B (zh) * | 2009-09-04 | 2012-11-14 | 江苏汉斯通药业有限公司 | 一种制备盐酸雷尼替丁的方法 |
MX345168B (es) * | 2010-06-02 | 2017-01-19 | Laboratorios Senosiain S A De C V * | Proceso para preparar ranitidina clorhidrato forma 2. |
-
2015
- 2015-05-26 CN CN201610807242.0A patent/CN106397374A/zh not_active Withdrawn
- 2015-05-26 CN CN201510273209.XA patent/CN104817523B/zh active Active
- 2015-05-26 CN CN201610823158.8A patent/CN106432147B/zh active Active
- 2015-05-26 CN CN201610823211.4A patent/CN106432148B/zh active Active
- 2015-05-26 CN CN201610823327.8A patent/CN106432149B/zh active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4521431A (en) * | 1980-10-01 | 1985-06-04 | Glaxo Group Limited | Aminoalkyl furan derivative |
CN1098720A (zh) * | 1991-12-20 | 1995-02-15 | 多坎化学有限公司 | 晶形1呋喃硝胺氢氯化物的制备 |
US5523423A (en) * | 1994-04-08 | 1996-06-04 | Acic (Canada) Inc. | Form of form 1 Ranitidine |
US5621120A (en) * | 1994-05-13 | 1997-04-15 | Ranbaxy Laboratories Limited | Process for the manufacture of form 1 ranitidine hydrochloride |
WO1999065890A1 (en) * | 1998-06-17 | 1999-12-23 | Russinsky Limited | Ranitidine adduct |
Non-Patent Citations (1)
Title |
---|
黄龙祥等: "盐酸雷尼替丁精制方法的改进", 《中国医药工业杂志》 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105055396A (zh) * | 2015-09-17 | 2015-11-18 | 青岛华之草医药科技有限公司 | 一种治疗胃病的药物盐酸雷尼替丁组合物冻干粉针剂 |
CN107382922A (zh) * | 2017-08-03 | 2017-11-24 | 江苏汉斯通药业有限公司 | 高透光度盐酸雷尼替丁的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
CN106432148B (zh) | 2018-04-17 |
CN106432149A (zh) | 2017-02-22 |
CN106432148A (zh) | 2017-02-22 |
CN104817523B (zh) | 2016-11-09 |
CN106432149B (zh) | 2018-04-17 |
CN106432147B (zh) | 2018-04-17 |
CN106397374A (zh) | 2017-02-15 |
CN106432147A (zh) | 2017-02-22 |
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Effective date of registration: 20160901 Address after: 264003 high tech Zone, Shandong, Yantai science and technology Avenue, No. 39 Applicant after: YANTAI HUAWEN XINXIN PHARMACEUTICAL CO., LTD. Applicant after: Wang Yufeng Applicant after: Li Xianmeng Address before: 276017 Shandong city of Linyi province or Linyi high tech Industrial Development Zone Technology Park Road, room A321 Applicant before: Miao Yiwen |
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Effective date of registration: 20170215 Address after: 264003 high tech Zone, Shandong, Yantai science and technology Avenue, No. 39 Patentee after: YANTAI HUAWEN XINXIN PHARMACEUTICAL CO., LTD. Address before: 264003 high tech Zone, Shandong, Yantai science and technology Avenue, No. 39 Patentee before: YANTAI HUAWEN XINXIN PHARMACEUTICAL CO., LTD. Patentee before: Wang Yufeng Patentee before: Li Xianmeng |
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Inventor after: Wang Yufeng Inventor after: Li Xianmeng Inventor after: Zhu Kongxi Inventor after: Zhang Xiaolei Inventor after: Bai Qingning Inventor after: Peng Xueyang Inventor after: Shen Xiang Inventor before: Wang Yufeng Inventor before: Li Xianmeng |
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Effective date of registration: 20170524 Address after: The 26 group and the village Yin Yang Zhen Qidong city 226000 Jiangsu city of Nantong Province Patentee after: Qidong and Hong agricultural by-products professional cooperatives Address before: 264003 high tech Zone, Shandong, Yantai science and technology Avenue, No. 39 Patentee before: YANTAI HUAWEN XINXIN PHARMACEUTICAL CO., LTD. |
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TR01 | Transfer of patent right | ||
CB03 | Change of inventor or designer information |
Inventor after: Wang Yufeng Inventor after: Li Xianmeng Inventor after: Zhu Kongxi Inventor after: Zhang Xiaolei Inventor after: Bai Qingning Inventor after: Peng Xueyang Inventor after: Shen Xiang Inventor after: Wang Lingzhang Inventor before: Wang Yufeng Inventor before: Li Xianmeng Inventor before: Zhu Kongxi Inventor before: Zhang Xiaolei Inventor before: Bai Qingning Inventor before: Peng Xueyang Inventor before: Shen Xiang |