CN100516063C - 硝呋太尔的生产方法 - Google Patents
硝呋太尔的生产方法 Download PDFInfo
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- CN100516063C CN100516063C CNB2006100648880A CN200610064888A CN100516063C CN 100516063 C CN100516063 C CN 100516063C CN B2006100648880 A CNB2006100648880 A CN B2006100648880A CN 200610064888 A CN200610064888 A CN 200610064888A CN 100516063 C CN100516063 C CN 100516063C
- Authority
- CN
- China
- Prior art keywords
- nifuratel
- described production
- methylthiomethyl
- alkali
- alkali metal
- 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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- SRQKTCXJCCHINN-NYYWCZLTSA-N nifuratel Chemical compound O=C1OC(CSC)CN1\N=C\C1=CC=C([N+]([O-])=O)O1 SRQKTCXJCCHINN-NYYWCZLTSA-N 0.000 title claims abstract description 47
- 229960002136 nifuratel Drugs 0.000 title claims abstract description 46
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 53
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims abstract description 16
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000003513 alkali Substances 0.000 claims abstract description 13
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims description 37
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 18
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical group OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 13
- 238000010438 heat treatment Methods 0.000 claims description 13
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical group [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052783 alkali metal Inorganic materials 0.000 claims description 11
- 150000001340 alkali metals Chemical class 0.000 claims description 11
- 239000000047 product Substances 0.000 claims description 11
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 10
- 239000003444 phase transfer catalyst Substances 0.000 claims description 10
- KQJQICVXLJTWQD-UHFFFAOYSA-N N-Methylthiourea Chemical compound CNC(N)=S KQJQICVXLJTWQD-UHFFFAOYSA-N 0.000 claims description 9
- CQKZEBKYHVVNFJ-UHFFFAOYSA-N NN1[CH-]OC(C1=O)CSC Chemical compound NN1[CH-]OC(C1=O)CSC CQKZEBKYHVVNFJ-UHFFFAOYSA-N 0.000 claims description 9
- 239000012312 sodium hydride Substances 0.000 claims description 9
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 9
- OSIXFNQHNPOVIA-UHFFFAOYSA-N 2-(methylsulfanylmethyl)oxirane Chemical compound CSCC1CO1 OSIXFNQHNPOVIA-UHFFFAOYSA-N 0.000 claims description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 8
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical group [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 8
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 7
- -1 polyoxyethylene Polymers 0.000 claims description 7
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 7
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 claims description 6
- HYBBIBNJHNGZAN-UHFFFAOYSA-N Furaldehyde Natural products O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 6
- 238000001953 recrystallisation Methods 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 5
- 229960000583 acetic acid Drugs 0.000 claims description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 5
- 239000012362 glacial acetic acid Substances 0.000 claims description 4
- 239000012467 final product Substances 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 239000001117 sulphuric acid Substances 0.000 claims description 2
- 235000011149 sulphuric acid Nutrition 0.000 claims description 2
- 229910052728 basic metal Inorganic materials 0.000 claims 2
- 150000003818 basic metals Chemical class 0.000 claims 2
- 238000006555 catalytic reaction Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 17
- 239000003814 drug Substances 0.000 abstract description 9
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 abstract description 7
- 230000006872 improvement Effects 0.000 abstract description 4
- 230000008901 benefit Effects 0.000 abstract description 3
- UQVUGWOKYIMFCM-UHFFFAOYSA-N 1-hydrazinyl-3-methylsulfanylpropan-2-ol Chemical compound CSCC(O)CNN UQVUGWOKYIMFCM-UHFFFAOYSA-N 0.000 abstract 1
- 239000005916 Methomyl Substances 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 239000000543 intermediate Substances 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 238000003756 stirring Methods 0.000 description 8
- 229940125898 compound 5 Drugs 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000003912 environmental pollution Methods 0.000 description 4
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- KLOHDWPABZXLGI-YWUHCJSESA-M ampicillin sodium Chemical compound [Na+].C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C([O-])=O)(C)C)=CC=CC=C1 KLOHDWPABZXLGI-YWUHCJSESA-M 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- RTYJTGSCYUUYAL-YCAHSCEMSA-L carbenicillin disodium Chemical compound [Na+].[Na+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)C(C([O-])=O)C1=CC=CC=C1 RTYJTGSCYUUYAL-YCAHSCEMSA-L 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910017053 inorganic salt Inorganic materials 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 210000001215 vagina Anatomy 0.000 description 2
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
- LQOBMKYCRQDMTN-UHFFFAOYSA-N 3-(2-ethylphenyl)pentan-3-amine;hydrochloride Chemical compound Cl.CCC1=CC=CC=C1C(N)(CC)CC LQOBMKYCRQDMTN-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 206010067484 Adverse reaction Diseases 0.000 description 1
- 208000004926 Bacterial Vaginosis Diseases 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 206010007134 Candida infections Diseases 0.000 description 1
- 241000606153 Chlamydia trachomatis Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 241000204031 Mycoplasma Species 0.000 description 1
- 241001502500 Trichomonadida Species 0.000 description 1
- 230000006838 adverse reaction Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical group 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 201000003984 candidiasis Diseases 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229940038705 chlamydia trachomatis Drugs 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 208000021302 gastroesophageal reflux disease Diseases 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 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
- 239000000203 mixture Substances 0.000 description 1
- IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical compound NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 description 1
- 229960001907 nitrofurazone Drugs 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000003408 phase transfer catalysis Methods 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Abstract
Description
Claims (16)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CNB2006100648880A CN100516063C (zh) | 2006-03-16 | 2006-03-16 | 硝呋太尔的生产方法 |
Applications Claiming Priority (1)
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CNB2006100648880A CN100516063C (zh) | 2006-03-16 | 2006-03-16 | 硝呋太尔的生产方法 |
Publications (2)
Publication Number | Publication Date |
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CN101037434A CN101037434A (zh) | 2007-09-19 |
CN100516063C true CN100516063C (zh) | 2009-07-22 |
Family
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Family Applications (1)
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CNB2006100648880A Active CN100516063C (zh) | 2006-03-16 | 2006-03-16 | 硝呋太尔的生产方法 |
Country Status (1)
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CN (1) | CN100516063C (zh) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101676284B (zh) * | 2008-09-17 | 2013-12-04 | 北京德众万全药物技术开发有限公司 | 一种高纯度的硝呋太尔的制备方法 |
EP2662371A1 (en) * | 2012-05-11 | 2013-11-13 | Polichem SA | (R)-Nifuratel and synthesis of (R) and (S)-Nifuratel |
CN102863434B (zh) * | 2012-10-19 | 2014-05-28 | 山东罗欣药业股份有限公司 | 一种硝呋太尔的合成方法 |
CN103396413A (zh) * | 2013-08-14 | 2013-11-20 | 盐城凯利药业有限公司 | 一种硝呋太尔的制备方法 |
CN104402874B (zh) * | 2013-12-02 | 2016-08-03 | 四川摩尔生物制药有限公司 | 一种如式e所示的化合物硝呋太尔的制备方法 |
CN107162996B (zh) * | 2017-05-31 | 2019-09-03 | 湖南方盛制药股份有限公司 | 一种高纯度硝呋太尔中间体的制备方法 |
CN108383834A (zh) * | 2018-04-13 | 2018-08-10 | 北京朗依制药有限公司沧州分公司 | 硝呋太尔环合杂质的去除工艺 |
CN108707146A (zh) * | 2018-08-15 | 2018-10-26 | 黄石法姆药业股份有限公司 | 一种硝呋太尔的合成方法 |
CN114478510B (zh) * | 2022-02-24 | 2022-11-01 | 盐城凯利药业有限公司 | 一种硝呋太尔的制备方法 |
-
2006
- 2006-03-16 CN CNB2006100648880A patent/CN100516063C/zh active Active
Non-Patent Citations (2)
Title |
---|
抗感染药物硝呋太尔的合成工艺改进. 李志万等人.解放军药学学报,第21卷第4期. 2005 |
抗感染药物硝呋太尔的合成工艺改进. 李志万等人.解放军药学学报,第21卷第4期. 2005 * |
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Assignee: Taiyangshi (Tangshan) Pharm Ind Co., Ltd. Assignor: Han Zhiqiang Contract fulfillment period: The duration of the contract is from 2007.09.12 to 2026.03.16 Contract record no.: Contract filing No. 2007990000068 Denomination of invention: Production method of the invention of Nifuratel Granted publication date: Unauthorized authorization day License type: Exclusive license Record date: 20071012 Assignee: Taiyangshi (Tangshan) Pharm Ind Co., Ltd. Assignor: Han Zhiqiang Contract fulfillment period: The duration of the contract is from 2007.09.12 to 2026.03.16 Contract record no.: Contract filing No. 2007990000068 Denomination of invention: Production method of the invention of Nifuratel Granted publication date: unauthorized License type: Exclusive license Record date: 20071012 |
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Assignee: Taiyangshi (Tangshan) Pharm Ind Co., Ltd. Assignor: Han Zhiqiang Contract fulfillment period: 2009.10.20 to 2014.10.19 contract change Contract record no.: 2009990001300 Denomination of invention: Production method of Nifuratel Granted publication date: 20090722 License type: General permission Record date: 20091130 Assignee: Taiyangshi (Tangshan) Pharm Ind Co., Ltd. Assignor: Han Zhiqiang Contract fulfillment period: 2009.12.16 to 2026.5.30 contract change Contract record no.: 2009990001331 Denomination of invention: Production method of Nifuratel Granted publication date: 20090722 License type: Exclusive license Record date: 20091217 Assignee: Taiyangshi (Tangshan) Pharm Ind Co., Ltd. Assignor: Han Zhiqiang Contract fulfillment period: 2009.10.20 to 2014.10.19 Contract record no.: 2009990001300 Denomination of invention: Production method of Nifuratel Granted publication date: 20090722 License type: General permission Record date: 20091130 Assignee: Taiyangshi (Tangshan) Pharm Ind Co., Ltd. Assignor: Han Zhiqiang Contract fulfillment period: 2009.12.16 to 2026.5.30 Contract record no.: 2009990001331 Denomination of invention: Production method of Nifuratel Granted publication date: 20090722 License type: Exclusive license Record date: 20091217 |
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Free format text: CORRECT: ADDRESS; FROM: 063020 SUNSTONE PHARMACEUTICAL CO., LTD., HUOJU ROAD, HIGH-TECH. DEVELOPMENT AREA, TANGSHAN CITY, HEBEI PROVINCE TO: 063020 NO. 139, HUOJU ROAD, HIGH-TECH. DEVELOPMENT AREA, TANGSHAN CITY, HEBEI PROVINCE |
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Effective date of registration: 20101119 Address after: 063020 Torch Road, Tangshan City hi tech Development Zone, Hebei 139, China Patentee after: Taiyangshi (Tangshan) Pharm Ind Co., Ltd. Address before: 063020 Hebei Tangshan City hi tech Development Zone Torch Road sun stone pharmaceutical industry Patentee before: Han Zhiqiang Effective date of registration: 20101119 Address after: 063020 Torch Road, Tangshan City hi tech Development Zone, Hebei 139, China Patentee after: Taiyangshi (Tangshan) Pharm Ind Co., Ltd. Address before: 063020 Hebei Tangshan City hi tech Development Zone Torch Road sun stone pharmaceutical industry Patentee before: Han Zhiqiang |
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Address after: 063020 Torch Road, Tangshan City hi tech Development Zone, Hebei 139, China Patentee after: China Resources Sanjiu (Tangshan) Pharmaceutical Co., Ltd Address before: 063020 Torch Road, Tangshan City hi tech Development Zone, Hebei 139, China Patentee before: SUNSTONE (TANGSHAN) PHARMACEUTICAL Co.,Ltd. |
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