CN100475773C - Synthesis method of naphthalene disulfonic acid aclatonium and similar compound thereof - Google Patents
Synthesis method of naphthalene disulfonic acid aclatonium and similar compound thereof Download PDFInfo
- Publication number
- CN100475773C CN100475773C CNB2006101456958A CN200610145695A CN100475773C CN 100475773 C CN100475773 C CN 100475773C CN B2006101456958 A CNB2006101456958 A CN B2006101456958A CN 200610145695 A CN200610145695 A CN 200610145695A CN 100475773 C CN100475773 C CN 100475773C
- Authority
- CN
- China
- Prior art keywords
- compound
- carry out
- organic solvent
- naphthalene disulfonic
- disulfonic acid
- 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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- 150000001875 compounds Chemical class 0.000 title claims description 53
- SRZGFCNCQUMTCP-UHFFFAOYSA-N aclatonium Chemical compound CC(=O)OC(C)C(=O)OCC[N+](C)(C)C SRZGFCNCQUMTCP-UHFFFAOYSA-N 0.000 title abstract description 14
- 229950008605 aclatonium Drugs 0.000 title abstract description 14
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 title description 16
- 238000001308 synthesis method Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 33
- 238000006243 chemical reaction Methods 0.000 claims description 48
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- 239000003960 organic solvent Substances 0.000 claims description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 9
- 230000032050 esterification Effects 0.000 claims description 8
- 238000005886 esterification reaction Methods 0.000 claims description 8
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 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 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 238000005917 acylation reaction Methods 0.000 claims description 4
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 claims description 4
- 150000001263 acyl chlorides Chemical class 0.000 claims description 3
- 150000001414 amino alcohols Chemical class 0.000 claims description 3
- 229960001701 chloroform Drugs 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000012454 non-polar solvent Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 abstract description 10
- 239000002994 raw material Substances 0.000 abstract description 7
- 239000004310 lactic acid Substances 0.000 abstract description 5
- 235000014655 lactic acid Nutrition 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 2
- 230000002194 synthesizing effect Effects 0.000 abstract description 2
- 230000001713 cholinergic effect Effects 0.000 abstract 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 235000019260 propionic acid Nutrition 0.000 description 8
- 238000001816 cooling Methods 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 238000010189 synthetic method Methods 0.000 description 6
- 238000010792 warming Methods 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 5
- 239000012346 acetyl chloride Substances 0.000 description 5
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 230000006837 decompression Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 210000002784 stomach Anatomy 0.000 description 3
- 208000007882 Gastritis Diseases 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 210000003445 biliary tract Anatomy 0.000 description 2
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 2
- 229960001231 choline Drugs 0.000 description 2
- 208000023652 chronic gastritis Diseases 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 230000001079 digestive effect Effects 0.000 description 2
- HCXPJMZQMWIBMO-UHFFFAOYSA-N dimethyl naphthalene-1,5-disulfonate Chemical compound C1=CC=C2C(S(=O)(=O)OC)=CC=CC2=C1S(=O)(=O)OC HCXPJMZQMWIBMO-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- ZGGKQVMITFBIRB-UHFFFAOYSA-N (1-chloro-1-oxopropan-2-yl) propanoate Chemical compound CCC(=O)OC(C)C(Cl)=O ZGGKQVMITFBIRB-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- IIXDEBPBOJRJKB-UHFFFAOYSA-N 2-propanoyloxypropanoic acid Chemical compound CCC(=O)OC(C)C(O)=O IIXDEBPBOJRJKB-UHFFFAOYSA-N 0.000 description 1
- DUBIROXGYMPWGD-UHFFFAOYSA-N 5-methoxysulfonylnaphthalene-1-sulfonic acid Chemical class C1=C(S(=O)(=O)O)C2=C(C=C1)C(S(=O)(=O)OC)=CC=C2 DUBIROXGYMPWGD-UHFFFAOYSA-N 0.000 description 1
- 206010000060 Abdominal distension Diseases 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 230000036528 appetite Effects 0.000 description 1
- 235000019789 appetite Nutrition 0.000 description 1
- 210000000941 bile Anatomy 0.000 description 1
- 208000003770 biliary dyskinesia Diseases 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 210000001198 duodenum Anatomy 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 230000007659 motor function Effects 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 210000001187 pylorus Anatomy 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- 210000001186 vagus nerve Anatomy 0.000 description 1
- 230000001720 vestibular Effects 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C219/06—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having the hydroxy groups esterified by carboxylic acids having the esterifying carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms of an acyclic saturated carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Nutrition Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (9)
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB2006101456958A CN100475773C (en) | 2006-11-24 | 2006-11-24 | Synthesis method of naphthalene disulfonic acid aclatonium and similar compound thereof |
JP2008551635A JP5007309B2 (en) | 2006-11-24 | 2007-10-24 | Method for the synthesis of acratonium napadisylate and its analogues |
PCT/CN2007/070948 WO2008061466A1 (en) | 2006-11-24 | 2007-10-24 | Synthetic methods of aclatonium napadisilate and analogs thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB2006101456958A CN100475773C (en) | 2006-11-24 | 2006-11-24 | Synthesis method of naphthalene disulfonic acid aclatonium and similar compound thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1948271A CN1948271A (en) | 2007-04-18 |
CN100475773C true CN100475773C (en) | 2009-04-08 |
Family
ID=38017914
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB2006101456958A Active CN100475773C (en) | 2006-11-24 | 2006-11-24 | Synthesis method of naphthalene disulfonic acid aclatonium and similar compound thereof |
Country Status (3)
Country | Link |
---|---|
JP (1) | JP5007309B2 (en) |
CN (1) | CN100475773C (en) |
WO (1) | WO2008061466A1 (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100475773C (en) * | 2006-11-24 | 2009-04-08 | 李晓祥 | Synthesis method of naphthalene disulfonic acid aclatonium and similar compound thereof |
CN110386878B (en) * | 2018-04-20 | 2022-04-22 | 扬子江药业集团有限公司 | Industrial preparation method of diethyl cholamine napadisylate |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2546845A1 (en) * | 1975-10-18 | 1977-04-28 | Basf Ag | Herbicidal (iso)quinolyloxy-alkanoic acid derivs. - prepd. e.g. by reacting hydroxy-(iso)quinoline cpds. with halo-alkanamides |
US5011973A (en) * | 1982-04-19 | 1991-04-30 | Toyama Chemical Co., Ltd. | Novel process for producing bischoline-disulfonate derivatives |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5414092B1 (en) * | 1970-12-28 | 1979-06-05 | ||
JPS551251B2 (en) * | 1973-06-20 | 1980-01-12 | ||
DE2425983C3 (en) * | 1973-06-12 | 1978-09-14 | Toyama Chemical Co. Ltd., Tokio | Sulphonic acid salts of acylcholines, processes for their preparation and pharmaceutical compositions containing them |
US4937367A (en) * | 1987-07-15 | 1990-06-26 | Zambon Group S.P.A. | Process for the preparation of intermediates for the synthesis of fosfomycin |
CN100475773C (en) * | 2006-11-24 | 2009-04-08 | 李晓祥 | Synthesis method of naphthalene disulfonic acid aclatonium and similar compound thereof |
-
2006
- 2006-11-24 CN CNB2006101456958A patent/CN100475773C/en active Active
-
2007
- 2007-10-24 WO PCT/CN2007/070948 patent/WO2008061466A1/en active Application Filing
- 2007-10-24 JP JP2008551635A patent/JP5007309B2/en not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2546845A1 (en) * | 1975-10-18 | 1977-04-28 | Basf Ag | Herbicidal (iso)quinolyloxy-alkanoic acid derivs. - prepd. e.g. by reacting hydroxy-(iso)quinoline cpds. with halo-alkanamides |
US5011973A (en) * | 1982-04-19 | 1991-04-30 | Toyama Chemical Co., Ltd. | Novel process for producing bischoline-disulfonate derivatives |
Non-Patent Citations (2)
Title |
---|
Acyloxyalkanoylcholine derivatives. Synthesis and contractingactivity on smooth muscle. Miura Koji etc.Yakugaku Zasshi,Vol.99 No.12. 1979 |
Acyloxyalkanoylcholine derivatives. Synthesis and contractingactivity on smooth muscle. Miura Koji etc.Yakugaku Zasshi,Vol.99 No.12. 1979 * |
Also Published As
Publication number | Publication date |
---|---|
JP2009524606A (en) | 2009-07-02 |
JP5007309B2 (en) | 2012-08-22 |
WO2008061466A1 (en) | 2008-05-29 |
CN1948271A (en) | 2007-04-18 |
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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 | ||
EE01 | Entry into force of recordation of patent licensing contract |
Application publication date: 20070418 Assignee: Xinxing Medicament Development Co., Ltd., Anhui Prov. Assignor: Li Xiaoxiang Contract record no.: 2012340000313 Denomination of invention: Synthesis method of naphthalene disulfonic acid aclatonium and its similar compound Granted publication date: 20090408 License type: Exclusive License Record date: 20120905 |
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TR01 | Transfer of patent right |
Effective date of registration: 20170615 Address after: 400000 Zhongxian water Ping Industrial Park, Chongqing Patentee after: Chongqing Juqinuomei Pharmaceutical Co., Ltd. Address before: 230031 No. 312, Suixi Road, Hefei, Anhui Patentee before: Li Xiaoxiang |
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TR01 | Transfer of patent right |