CN104974165A - 一种治疗男性勃起功能障碍的枸橼酸西地那非化合物 - Google Patents
一种治疗男性勃起功能障碍的枸橼酸西地那非化合物 Download PDFInfo
- Publication number
- CN104974165A CN104974165A CN201510436399.2A CN201510436399A CN104974165A CN 104974165 A CN104974165 A CN 104974165A CN 201510436399 A CN201510436399 A CN 201510436399A CN 104974165 A CN104974165 A CN 104974165A
- Authority
- CN
- China
- Prior art keywords
- sildenafil citrate
- citrate compound
- ethanol
- methylene dichloride
- methyl pyrrolidone
- 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.)
- Granted
Links
- 229960002639 sildenafil citrate Drugs 0.000 title claims abstract description 78
- -1 Sildenafil citrate compound Chemical class 0.000 title claims abstract description 34
- 230000004064 dysfunction Effects 0.000 title abstract 2
- 229910017488 Cu K Inorganic materials 0.000 claims abstract description 6
- 229910017541 Cu-K Inorganic materials 0.000 claims abstract description 6
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 48
- DEIYFTQMQPDXOT-UHFFFAOYSA-N sildenafil citrate Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.CCCC1=NN(C)C(C(N2)=O)=C1N=C2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(C)CC1 DEIYFTQMQPDXOT-UHFFFAOYSA-N 0.000 claims description 44
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 24
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 24
- 239000012046 mixed solvent Substances 0.000 claims description 21
- 238000003756 stirring Methods 0.000 claims description 15
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 9
- 238000001035 drying Methods 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 208000010228 Erectile Dysfunction Diseases 0.000 claims description 7
- 201000001881 impotence Diseases 0.000 claims description 7
- 238000005259 measurement Methods 0.000 claims description 6
- 230000005260 alpha ray Effects 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 4
- 238000005516 engineering process Methods 0.000 abstract description 2
- 239000012535 impurity Substances 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 15
- 239000003814 drug Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 7
- 101100189582 Dictyostelium discoideum pdeD gene Proteins 0.000 description 4
- 101150098694 PDE5A gene Proteins 0.000 description 4
- 241000405119 Virga Species 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 102100029175 cGMP-specific 3',5'-cyclic phosphodiesterase Human genes 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000013112 stability test Methods 0.000 description 3
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- 210000005226 corpus cavernosum Anatomy 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000001856 erectile effect Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 210000002460 smooth muscle Anatomy 0.000 description 2
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 210000001772 blood platelet Anatomy 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000003899 penis Anatomy 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 239000000955 prescription drug Substances 0.000 description 1
- 230000036259 sexual stimuli Effects 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000009278 visceral effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (7)
Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201711374500.1A CN107955009A (zh) | 2015-07-23 | 2015-07-23 | 一种制备治疗男性勃起功能障碍的化合物的方法 |
CN201711329369.7A CN107722020A (zh) | 2015-07-23 | 2015-07-23 | 一种治疗男性勃起功能障碍的枸橼酸西地那非化合物 |
CN201510436399.2A CN104974165B (zh) | 2015-07-23 | 2015-07-23 | 一种治疗男性勃起功能障碍的枸橼酸西地那非化合物 |
CN201711328270.5A CN107880047A (zh) | 2015-07-23 | 2015-07-23 | 一种枸橼酸西地那非化合物 |
CN201711327343.9A CN107722018A (zh) | 2015-07-23 | 2015-07-23 | 一种治疗男性勃起功能障碍的枸橼酸西地那非化合物 |
CN201711374498.8A CN107973799A (zh) | 2015-07-23 | 2015-07-23 | 制备治疗男性勃起功能障碍的枸橼酸西地那非化合物的方法 |
CN201711375487.1A CN107827895A (zh) | 2015-07-23 | 2015-07-23 | 一种制备治疗男性勃起功能障碍的枸橼酸西地那非化合物的方法 |
CN201711327352.8A CN107722019A (zh) | 2015-07-23 | 2015-07-23 | 一种治疗男性勃起功能障碍的枸橼酸西地那非化合物 |
CN201711329418.7A CN107903270A (zh) | 2015-07-23 | 2015-07-23 | 一种治疗男性勃起功能障碍的枸橼酸西地那非化合物 |
CN201711329368.2A CN107880048A (zh) | 2015-07-23 | 2015-07-23 | 一种枸橼酸西地那非化合物 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510436399.2A CN104974165B (zh) | 2015-07-23 | 2015-07-23 | 一种治疗男性勃起功能障碍的枸橼酸西地那非化合物 |
Related Child Applications (9)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201711329418.7A Division CN107903270A (zh) | 2015-07-23 | 2015-07-23 | 一种治疗男性勃起功能障碍的枸橼酸西地那非化合物 |
CN201711374500.1A Division CN107955009A (zh) | 2015-07-23 | 2015-07-23 | 一种制备治疗男性勃起功能障碍的化合物的方法 |
CN201711328270.5A Division CN107880047A (zh) | 2015-07-23 | 2015-07-23 | 一种枸橼酸西地那非化合物 |
CN201711327343.9A Division CN107722018A (zh) | 2015-07-23 | 2015-07-23 | 一种治疗男性勃起功能障碍的枸橼酸西地那非化合物 |
CN201711374498.8A Division CN107973799A (zh) | 2015-07-23 | 2015-07-23 | 制备治疗男性勃起功能障碍的枸橼酸西地那非化合物的方法 |
CN201711375487.1A Division CN107827895A (zh) | 2015-07-23 | 2015-07-23 | 一种制备治疗男性勃起功能障碍的枸橼酸西地那非化合物的方法 |
CN201711329368.2A Division CN107880048A (zh) | 2015-07-23 | 2015-07-23 | 一种枸橼酸西地那非化合物 |
CN201711329369.7A Division CN107722020A (zh) | 2015-07-23 | 2015-07-23 | 一种治疗男性勃起功能障碍的枸橼酸西地那非化合物 |
CN201711327352.8A Division CN107722019A (zh) | 2015-07-23 | 2015-07-23 | 一种治疗男性勃起功能障碍的枸橼酸西地那非化合物 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN104974165A true CN104974165A (zh) | 2015-10-14 |
CN104974165B CN104974165B (zh) | 2017-12-01 |
Family
ID=54271176
Family Applications (10)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201711375487.1A Withdrawn CN107827895A (zh) | 2015-07-23 | 2015-07-23 | 一种制备治疗男性勃起功能障碍的枸橼酸西地那非化合物的方法 |
CN201711374500.1A Withdrawn CN107955009A (zh) | 2015-07-23 | 2015-07-23 | 一种制备治疗男性勃起功能障碍的化合物的方法 |
CN201510436399.2A Active CN104974165B (zh) | 2015-07-23 | 2015-07-23 | 一种治疗男性勃起功能障碍的枸橼酸西地那非化合物 |
CN201711327352.8A Pending CN107722019A (zh) | 2015-07-23 | 2015-07-23 | 一种治疗男性勃起功能障碍的枸橼酸西地那非化合物 |
CN201711374498.8A Withdrawn CN107973799A (zh) | 2015-07-23 | 2015-07-23 | 制备治疗男性勃起功能障碍的枸橼酸西地那非化合物的方法 |
CN201711329369.7A Pending CN107722020A (zh) | 2015-07-23 | 2015-07-23 | 一种治疗男性勃起功能障碍的枸橼酸西地那非化合物 |
CN201711329368.2A Withdrawn CN107880048A (zh) | 2015-07-23 | 2015-07-23 | 一种枸橼酸西地那非化合物 |
CN201711329418.7A Withdrawn CN107903270A (zh) | 2015-07-23 | 2015-07-23 | 一种治疗男性勃起功能障碍的枸橼酸西地那非化合物 |
CN201711327343.9A Pending CN107722018A (zh) | 2015-07-23 | 2015-07-23 | 一种治疗男性勃起功能障碍的枸橼酸西地那非化合物 |
CN201711328270.5A Pending CN107880047A (zh) | 2015-07-23 | 2015-07-23 | 一种枸橼酸西地那非化合物 |
Family Applications Before (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201711375487.1A Withdrawn CN107827895A (zh) | 2015-07-23 | 2015-07-23 | 一种制备治疗男性勃起功能障碍的枸橼酸西地那非化合物的方法 |
CN201711374500.1A Withdrawn CN107955009A (zh) | 2015-07-23 | 2015-07-23 | 一种制备治疗男性勃起功能障碍的化合物的方法 |
Family Applications After (7)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201711327352.8A Pending CN107722019A (zh) | 2015-07-23 | 2015-07-23 | 一种治疗男性勃起功能障碍的枸橼酸西地那非化合物 |
CN201711374498.8A Withdrawn CN107973799A (zh) | 2015-07-23 | 2015-07-23 | 制备治疗男性勃起功能障碍的枸橼酸西地那非化合物的方法 |
CN201711329369.7A Pending CN107722020A (zh) | 2015-07-23 | 2015-07-23 | 一种治疗男性勃起功能障碍的枸橼酸西地那非化合物 |
CN201711329368.2A Withdrawn CN107880048A (zh) | 2015-07-23 | 2015-07-23 | 一种枸橼酸西地那非化合物 |
CN201711329418.7A Withdrawn CN107903270A (zh) | 2015-07-23 | 2015-07-23 | 一种治疗男性勃起功能障碍的枸橼酸西地那非化合物 |
CN201711327343.9A Pending CN107722018A (zh) | 2015-07-23 | 2015-07-23 | 一种治疗男性勃起功能障碍的枸橼酸西地那非化合物 |
CN201711328270.5A Pending CN107880047A (zh) | 2015-07-23 | 2015-07-23 | 一种枸橼酸西地那非化合物 |
Country Status (1)
Country | Link |
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CN (10) | CN107827895A (zh) |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0463756A1 (en) * | 1990-06-20 | 1992-01-02 | Pfizer Limited | Pyrazolopyrimidinone antianginal agents |
CN104370915A (zh) * | 2014-11-06 | 2015-02-25 | 成都医路康医学技术服务有限公司 | 枸橼酸西地那非的制备方法 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002539165A (ja) * | 1999-03-16 | 2002-11-19 | ペンテツク・フアーマシユーテイカルズ・インコーポレイテツド | 舌下またはバッカル投与により送出されるシルデナフィルの制御放出 |
CN1092660C (zh) * | 1999-07-12 | 2002-10-16 | 广东天普生物化学制药有限公司 | 制备西地那非的方法 |
CN1925860A (zh) * | 2004-01-05 | 2007-03-07 | 特瓦制药工业有限公司 | 制备西地那非碱及其柠檬酸盐的方法 |
WO2008074194A1 (fr) * | 2006-12-21 | 2008-06-26 | Topharman Shanghai Co., Ltd. | Procédé de préparation du sildénafil et de ses intermédiaires |
WO2009125415A1 (en) * | 2008-04-07 | 2009-10-15 | Hetero Research Foundation | Amorphous form of sildenafil citrate |
CN101530400B (zh) * | 2009-04-14 | 2011-05-04 | 李浪辉 | 一种治疗阴茎勃起功能障碍的泡腾片及其制备方法 |
-
2015
- 2015-07-23 CN CN201711375487.1A patent/CN107827895A/zh not_active Withdrawn
- 2015-07-23 CN CN201711374500.1A patent/CN107955009A/zh not_active Withdrawn
- 2015-07-23 CN CN201510436399.2A patent/CN104974165B/zh active Active
- 2015-07-23 CN CN201711327352.8A patent/CN107722019A/zh active Pending
- 2015-07-23 CN CN201711374498.8A patent/CN107973799A/zh not_active Withdrawn
- 2015-07-23 CN CN201711329369.7A patent/CN107722020A/zh active Pending
- 2015-07-23 CN CN201711329368.2A patent/CN107880048A/zh not_active Withdrawn
- 2015-07-23 CN CN201711329418.7A patent/CN107903270A/zh not_active Withdrawn
- 2015-07-23 CN CN201711327343.9A patent/CN107722018A/zh active Pending
- 2015-07-23 CN CN201711328270.5A patent/CN107880047A/zh active Pending
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0463756A1 (en) * | 1990-06-20 | 1992-01-02 | Pfizer Limited | Pyrazolopyrimidinone antianginal agents |
CN104370915A (zh) * | 2014-11-06 | 2015-02-25 | 成都医路康医学技术服务有限公司 | 枸橼酸西地那非的制备方法 |
Non-Patent Citations (2)
Title |
---|
DMITRIJS STEPANOVS ET AL.: "Molecular and Crystal Structure of Sildenafil Base", 《ZEITSCHRIFT FUR NATURFORSCHUNG B》 * |
向红琳等: "枸橼酸西地那非合成工艺改进", 《湖南医学高等专科学校学报》 * |
Also Published As
Publication number | Publication date |
---|---|
CN107722020A (zh) | 2018-02-23 |
CN107880047A (zh) | 2018-04-06 |
CN107955009A (zh) | 2018-04-24 |
CN107722018A (zh) | 2018-02-23 |
CN107827895A (zh) | 2018-03-23 |
CN107722019A (zh) | 2018-02-23 |
CN107903270A (zh) | 2018-04-13 |
CN104974165B (zh) | 2017-12-01 |
CN107973799A (zh) | 2018-05-01 |
CN107880048A (zh) | 2018-04-06 |
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Inventor after: Bi Binna Inventor before: Wang Yumei |
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Effective date of registration: 20171108 Address after: Twenty-seventh, No. 396, Emei Mountain Road, Huangdao District, Shandong City, Qingdao Province, Qingdao 266555, Optics Valley Software Park, second floors Applicant after: QINGDAO HUAZHICAO PHARMACEUTICAL Co.,Ltd. Applicant after: Bi Binna Address before: 108, room 2, building 266109, Qingdao blue bio Pharmaceutical Industrial Park, 368 Hedong Road, Hedong District, Qingdao, Shandong Applicant before: QINGDAO LANSHENGYANG PHARMACEUTICAL AND BIOTECHNOLOGY Co.,Ltd. |
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Effective date of registration: 20171120 Address after: Twenty-seventh, No. 396, Emei Mountain Road, Huangdao District, Shandong City, Qingdao Province, Qingdao 266555, Optics Valley Software Park, second floors Patentee after: QINGDAO HUAZHICAO PHARMACEUTICAL Co.,Ltd. Address before: Twenty-seventh, No. 396, Emei Mountain Road, Huangdao District, Shandong City, Qingdao Province, Qingdao 266555, Optics Valley Software Park, second floors Co-patentee before: Bi Binna Patentee before: QINGDAO HUAZHICAO PHARMACEUTICAL Co.,Ltd. |
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Effective date of registration: 20181011 Address after: 276017 Shandong Linyi high tech Zone, double moon road science and Technology Pioneer Park A321 Patentee after: LINYI CAOZHIMEI PHARMACEUTICAL TECHNOLOGY Co.,Ltd. Address before: 266555 second second layers of Qingdao Optics Valley Software Park, 396 Emei Mountain Road, Huangdao District, Qingdao, Shandong, China Patentee before: QINGDAO HUAZHICAO PHARMACEUTICAL Co.,Ltd. |
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Effective date of registration: 20230802 Address after: No. 50 Caiyuan Bay, Lidingwu Village, Wuxue Street, Wuxue City, Huanggang City, Hubei Province, 435400 Patentee after: Cai Kunyuan Address before: 276017 Shandong Linyi high tech Zone, double moon road science and Technology Pioneer Park A321 Patentee before: LINYI CAOZHIMEI PHARMACEUTICAL TECHNOLOGY Co.,Ltd. |
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