CN104974165B - 一种治疗男性***功能障碍的枸橼酸西地那非化合物 - Google Patents
一种治疗男性***功能障碍的枸橼酸西地那非化合物 Download PDFInfo
- Publication number
- CN104974165B CN104974165B CN201510436399.2A CN201510436399A CN104974165B CN 104974165 B CN104974165 B CN 104974165B CN 201510436399 A CN201510436399 A CN 201510436399A CN 104974165 B CN104974165 B CN 104974165B
- Authority
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- China
- Prior art keywords
- sildenafil citrate
- compound
- ethanol
- growing
- grain
- 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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- 229960002639 sildenafil citrate Drugs 0.000 title claims abstract description 59
- -1 sildenafil citrate compound Chemical class 0.000 title claims abstract description 22
- 208000010228 Erectile Dysfunction Diseases 0.000 title claims abstract description 9
- 201000001881 impotence Diseases 0.000 title claims abstract description 9
- 238000005259 measurement Methods 0.000 claims abstract description 7
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 7
- 230000005260 alpha ray Effects 0.000 claims abstract description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 40
- 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 37
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 20
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 19
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 17
- 239000012046 mixed solvent Substances 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- 238000003756 stirring Methods 0.000 claims description 15
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical class CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 claims description 7
- 229910017488 Cu K Inorganic materials 0.000 claims description 5
- 229910017541 Cu-K Inorganic materials 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 238000012360 testing method Methods 0.000 abstract description 15
- 239000012535 impurity Substances 0.000 abstract description 6
- 238000010521 absorption reaction Methods 0.000 abstract description 4
- 238000005516 engineering process Methods 0.000 abstract description 3
- 239000003814 drug Substances 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 7
- 235000015165 citric acid Nutrition 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 101100189582 Dictyostelium discoideum pdeD gene Proteins 0.000 description 4
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 4
- 101150098694 PDE5A gene Proteins 0.000 description 4
- 102100029175 cGMP-specific 3',5'-cyclic phosphodiesterase Human genes 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- 240000004307 Citrus medica Species 0.000 description 2
- 230000015572 biosynthetic process Effects 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
- 238000001914 filtration Methods 0.000 description 2
- 238000007689 inspection Methods 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 210000002460 smooth muscle Anatomy 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 235000002710 Ilex cornuta Nutrition 0.000 description 1
- 241001310146 Ilex cornuta Species 0.000 description 1
- 235000010326 Osmanthus heterophyllus Nutrition 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 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
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical class ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 210000003899 penis Anatomy 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 229940126532 prescription medicine Drugs 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 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
- 239000000126 substance 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 (2)
Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201711375487.1A CN107827895A (zh) | 2015-07-23 | 2015-07-23 | 一种制备治疗男性***功能障碍的枸橼酸西地那非化合物的方法 |
CN201711328270.5A CN107880047A (zh) | 2015-07-23 | 2015-07-23 | 一种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 |
CN201510436399.2A CN104974165B (zh) | 2015-07-23 | 2015-07-23 | 一种治疗男性***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***功能障碍的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***功能障碍的枸橼酸西地那非化合物 |
CN201711374500.1A CN107955009A (zh) | 2015-07-23 | 2015-07-23 | 一种制备治疗男性***功能障碍的化合物的方法 |
CN201711327352.8A CN107722019A (zh) | 2015-07-23 | 2015-07-23 | 一种治疗男性***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***功能障碍的枸橼酸西地那非化合物的方法 |
CN201711329369.7A CN107722020A (zh) | 2015-07-23 | 2015-07-23 | 一种治疗男性***功能障碍的枸橼酸西地那非化合物 |
Applications Claiming Priority (1)
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CN201510436399.2A CN104974165B (zh) | 2015-07-23 | 2015-07-23 | 一种治疗男性***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 |
---|---|---|---|
CN201711329368.2A Division CN107880048A (zh) | 2015-07-23 | 2015-07-23 | 一种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***功能障碍的枸橼酸西地那非化合物的方法 |
CN201711329418.7A Division CN107903270A (zh) | 2015-07-23 | 2015-07-23 | 一种治疗男性***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***功能障碍的枸橼酸西地那非化合物 |
CN201711375487.1A Division CN107827895A (zh) | 2015-07-23 | 2015-07-23 | 一种制备治疗男性***功能障碍的枸橼酸西地那非化合物的方法 |
CN201711327343.9A Division CN107722018A (zh) | 2015-07-23 | 2015-07-23 | 一种治疗男性***功能障碍的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***功能障碍的枸橼酸西地那非化合物 |
CN201711328270.5A Division CN107880047A (zh) | 2015-07-23 | 2015-07-23 | 一种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***功能障碍的化合物的方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN104974165A CN104974165A (zh) | 2015-10-14 |
CN104974165B true CN104974165B (zh) | 2017-12-01 |
Family
ID=54271176
Family Applications (10)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201711374500.1A Withdrawn CN107955009A (zh) | 2015-07-23 | 2015-07-23 | 一种制备治疗男性***功能障碍的化合物的方法 |
CN201711374498.8A Withdrawn CN107973799A (zh) | 2015-07-23 | 2015-07-23 | 制备治疗男性***功能障碍的枸橼酸西地那非化合物的方法 |
CN201711375487.1A Withdrawn CN107827895A (zh) | 2015-07-23 | 2015-07-23 | 一种制备治疗男性***功能障碍的枸橼酸西地那非化合物的方法 |
CN201510436399.2A Active CN104974165B (zh) | 2015-07-23 | 2015-07-23 | 一种治疗男性***功能障碍的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***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 |
CN201711327343.9A Pending CN107722018A (zh) | 2015-07-23 | 2015-07-23 | 一种治疗男性***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 |
CN201711329369.7A Pending CN107722020A (zh) | 2015-07-23 | 2015-07-23 | 一种治疗男性***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***功能障碍的枸橼酸西地那非化合物 |
Family Applications Before (3)
Application Number | Title | Priority Date | Filing Date |
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CN201711374500.1A Withdrawn CN107955009A (zh) | 2015-07-23 | 2015-07-23 | 一种制备治疗男性***功能障碍的化合物的方法 |
CN201711374498.8A Withdrawn CN107973799A (zh) | 2015-07-23 | 2015-07-23 | 制备治疗男性***功能障碍的枸橼酸西地那非化合物的方法 |
CN201711375487.1A Withdrawn CN107827895A (zh) | 2015-07-23 | 2015-07-23 | 一种制备治疗男性***功能障碍的枸橼酸西地那非化合物的方法 |
Family Applications After (6)
Application Number | Title | Priority Date | Filing Date |
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CN201711329418.7A Withdrawn CN107903270A (zh) | 2015-07-23 | 2015-07-23 | 一种治疗男性***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 |
CN201711327343.9A Pending CN107722018A (zh) | 2015-07-23 | 2015-07-23 | 一种治疗男性***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 |
CN201711329369.7A Pending CN107722020A (zh) | 2015-07-23 | 2015-07-23 | 一种治疗男性***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***功能障碍的枸橼酸西地那非化合物 |
Country Status (1)
Country | Link |
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CN (10) | CN107955009A (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 |
---|---|---|---|---|
AU3744800A (en) * | 1999-03-16 | 2000-10-04 | Pentech Pharmaceuticals, Inc. | Controlled release of sildenafil delivered by sublingual or buccal administration |
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 |
US8071765B2 (en) * | 2006-12-21 | 2011-12-06 | Topharman Shanghai Co., Ltd. | Process for the preparation of sildenafil and intermediates thereof |
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******功能障碍的泡腾片及其制备方法 |
-
2015
- 2015-07-23 CN CN201711374500.1A patent/CN107955009A/zh not_active Withdrawn
- 2015-07-23 CN CN201711374498.8A patent/CN107973799A/zh not_active Withdrawn
- 2015-07-23 CN CN201711375487.1A patent/CN107827895A/zh not_active Withdrawn
- 2015-07-23 CN CN201510436399.2A patent/CN104974165B/zh active Active
- 2015-07-23 CN CN201711329418.7A patent/CN107903270A/zh not_active Withdrawn
- 2015-07-23 CN CN201711329368.2A patent/CN107880048A/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
- 2015-07-23 CN CN201711329369.7A patent/CN107722020A/zh active Pending
- 2015-07-23 CN CN201711327352.8A patent/CN107722019A/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 |
---|
Molecular and Crystal Structure of Sildenafil Base;Dmitrijs Stepanovs et al.;《Zeitschrift Fur Naturforschung B》;20040123;第67卷(第5期);491-494 * |
枸橼酸西地那非合成工艺改进;向红琳等;《湖南医学高等专科学校学报》;20001231;第2卷(第1期);47-48 * |
Also Published As
Publication number | Publication date |
---|---|
CN107880048A (zh) | 2018-04-06 |
CN107903270A (zh) | 2018-04-13 |
CN107827895A (zh) | 2018-03-23 |
CN107880047A (zh) | 2018-04-06 |
CN107722020A (zh) | 2018-02-23 |
CN107973799A (zh) | 2018-05-01 |
CN104974165A (zh) | 2015-10-14 |
CN107722018A (zh) | 2018-02-23 |
CN107955009A (zh) | 2018-04-24 |
CN107722019A (zh) | 2018-02-23 |
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Inventor after: Bi Binna Inventor before: Wang Yumei |
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TA01 | Transfer of patent application right |
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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