CN103626819B - 雄甾-3β,5α,6β-三醇的晶型化合物及其制备方法 - Google Patents
雄甾-3β,5α,6β-三醇的晶型化合物及其制备方法 Download PDFInfo
- Publication number
- CN103626819B CN103626819B CN201310393373.5A CN201310393373A CN103626819B CN 103626819 B CN103626819 B CN 103626819B CN 201310393373 A CN201310393373 A CN 201310393373A CN 103626819 B CN103626819 B CN 103626819B
- Authority
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- China
- Prior art keywords
- crystal
- diffraction
- androstane
- triols
- beta
- 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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Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 30
- 150000001875 compounds Chemical class 0.000 title claims abstract description 22
- 239000013078 crystal Substances 0.000 claims abstract description 116
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 40
- 238000010790 dilution Methods 0.000 claims description 23
- 239000012895 dilution Substances 0.000 claims description 23
- 125000006850 spacer group Chemical group 0.000 claims description 9
- 230000007704 transition Effects 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 3
- 238000000634 powder X-ray diffraction Methods 0.000 abstract description 27
- 230000015572 biosynthetic process Effects 0.000 abstract description 18
- 230000000857 drug effect Effects 0.000 abstract description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 28
- 239000002904 solvent Substances 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
- 238000007605 air drying Methods 0.000 description 15
- 238000000967 suction filtration Methods 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000004090 dissolution Methods 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000001757 thermogravimetry curve Methods 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- QNRATNLHPGXHMA-XZHTYLCXSA-N (r)-(6-ethoxyquinolin-4-yl)-[(2s,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]methanol;hydrochloride Chemical compound Cl.C([C@H]([C@H](C1)CC)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OCC)C=C21 QNRATNLHPGXHMA-XZHTYLCXSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000002050 diffraction method Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000000324 neuroprotective effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
- C07J1/0003—Androstane derivatives
- C07J1/0007—Androstane derivatives not substituted in position 17
-
- 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)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210060611.6A CN102617685B (zh) | 2012-03-08 | 2012-03-08 | 雄甾-3β,5α,6β-三醇的晶型化合物及其制备方法 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201210060611.6A Division CN102617685B (zh) | 2012-03-08 | 2012-03-08 | 雄甾-3β,5α,6β-三醇的晶型化合物及其制备方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103626819A CN103626819A (zh) | 2014-03-12 |
| CN103626819B true CN103626819B (zh) | 2016-01-20 |
Family
ID=46557937
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310393373.5A Active CN103626819B (zh) | 2012-03-08 | 2012-03-08 | 雄甾-3β,5α,6β-三醇的晶型化合物及其制备方法 |
| CN201210060611.6A Active CN102617685B (zh) | 2012-03-08 | 2012-03-08 | 雄甾-3β,5α,6β-三醇的晶型化合物及其制备方法 |
| CN201310393026.2A Active CN103626818B (zh) | 2012-03-08 | 2012-03-08 | 雄甾-3β,5α,6β-三醇的晶型化合物及其制备方法 |
| CN201310392426.1A Active CN103626817B (zh) | 2012-03-08 | 2012-03-08 | 雄甾-3β,5α,6β-三醇的晶型化合物及其制备方法 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201210060611.6A Active CN102617685B (zh) | 2012-03-08 | 2012-03-08 | 雄甾-3β,5α,6β-三醇的晶型化合物及其制备方法 |
| CN201310393026.2A Active CN103626818B (zh) | 2012-03-08 | 2012-03-08 | 雄甾-3β,5α,6β-三醇的晶型化合物及其制备方法 |
| CN201310392426.1A Active CN103626817B (zh) | 2012-03-08 | 2012-03-08 | 雄甾-3β,5α,6β-三醇的晶型化合物及其制备方法 |
Country Status (13)
| Country | Link |
|---|---|
| US (3) | US9688716B2 (https=) |
| EP (2) | EP3112374A1 (https=) |
| JP (1) | JP2015511587A (https=) |
| KR (1) | KR20150002653A (https=) |
| CN (4) | CN103626819B (https=) |
| AU (1) | AU2012372640B2 (https=) |
| CA (2) | CA2866398C (https=) |
| IL (1) | IL234492A (https=) |
| IN (1) | IN2014DN08198A (https=) |
| RU (1) | RU2608894C2 (https=) |
| SG (1) | SG11201405376TA (https=) |
| TW (1) | TW201336861A (https=) |
| WO (1) | WO2013131305A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR112014027878A2 (pt) * | 2012-05-07 | 2017-06-27 | Procter & Gamble | recipientes flexíveis |
| CN109985048B (zh) * | 2017-12-29 | 2021-06-29 | 广州市赛普特医药科技股份有限公司 | 2β,3α,5α-三羟基雄甾-6-酮用于炎症反应的治疗 |
| US11532903B2 (en) * | 2021-04-01 | 2022-12-20 | Ideal Industries, Inc. | Universal electrical connector |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0075189A1 (en) * | 1981-09-21 | 1983-03-30 | Schering Aktiengesellschaft | 3-Beta,7-beta,15-alpha-trihydroxy-5-androsten-17-one, its 3,15-dipivalate, and its preparation |
| CN101884638A (zh) * | 2010-07-09 | 2010-11-17 | 中山大学 | 5α-雄甾(烷)-3β,5,6β-三醇在制备神经元保护药物中的应用 |
| CN101961311A (zh) * | 2010-09-21 | 2011-02-02 | 中山大学 | 一种5α-雄甾(烷)-3β,5,6β-三醇注射剂及其制备方法 |
| CN102180928A (zh) * | 2011-03-15 | 2011-09-14 | 中山大学 | 3β,5α,6β-三羟基甾体化合物及其合成方法和应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2191576A (en) | 1936-11-21 | 1940-02-27 | Soc Of Chemical Ind | 3,5,6-trihydroxy androstane and pregnane compounds |
| US2191578A (en) | 1939-07-24 | 1940-02-27 | Crosley Corp | Ice-cream tray |
| US6046185A (en) * | 1996-07-11 | 2000-04-04 | Inflazyme Pharmaceuticals Ltd. | 6,7-oxygenated steroids and uses related thereto |
-
2012
- 2012-03-08 CN CN201310393373.5A patent/CN103626819B/zh active Active
- 2012-03-08 CN CN201210060611.6A patent/CN102617685B/zh active Active
- 2012-03-08 CN CN201310393026.2A patent/CN103626818B/zh active Active
- 2012-03-08 CN CN201310392426.1A patent/CN103626817B/zh active Active
- 2012-04-11 CA CA2866398A patent/CA2866398C/en active Active
- 2012-04-11 EP EP16184231.5A patent/EP3112374A1/en not_active Ceased
- 2012-04-11 SG SG11201405376TA patent/SG11201405376TA/en unknown
- 2012-04-11 CA CA2909998A patent/CA2909998A1/en not_active Abandoned
- 2012-04-11 WO PCT/CN2012/073854 patent/WO2013131305A1/zh not_active Ceased
- 2012-04-11 US US14/383,405 patent/US9688716B2/en active Active
- 2012-04-11 KR KR1020147028362A patent/KR20150002653A/ko not_active Ceased
- 2012-04-11 EP EP12870566.2A patent/EP2889303A4/en not_active Withdrawn
- 2012-04-11 JP JP2014560211A patent/JP2015511587A/ja active Pending
- 2012-04-11 RU RU2014136891A patent/RU2608894C2/ru active
- 2012-04-11 AU AU2012372640A patent/AU2012372640B2/en active Active
- 2012-04-11 IN IN8198DEN2014 patent/IN2014DN08198A/en unknown
-
2013
- 2013-03-07 TW TW102108093A patent/TW201336861A/zh unknown
-
2014
- 2014-09-07 IL IL234492A patent/IL234492A/en active IP Right Grant
-
2017
- 2017-05-08 US US15/589,228 patent/US9944672B2/en active Active
- 2017-05-08 US US15/589,268 patent/US9944673B2/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0075189A1 (en) * | 1981-09-21 | 1983-03-30 | Schering Aktiengesellschaft | 3-Beta,7-beta,15-alpha-trihydroxy-5-androsten-17-one, its 3,15-dipivalate, and its preparation |
| CN101884638A (zh) * | 2010-07-09 | 2010-11-17 | 中山大学 | 5α-雄甾(烷)-3β,5,6β-三醇在制备神经元保护药物中的应用 |
| CN101961311A (zh) * | 2010-09-21 | 2011-02-02 | 中山大学 | 一种5α-雄甾(烷)-3β,5,6β-三醇注射剂及其制备方法 |
| CN102180928A (zh) * | 2011-03-15 | 2011-09-14 | 中山大学 | 3β,5α,6β-三羟基甾体化合物及其合成方法和应用 |
Non-Patent Citations (1)
| Title |
|---|
| The reaction of Lead Tetraacetate with 3β-Hydroxy Steroids;Rikio Ohuchi et al;《Chem. Pharm. Bull.》;19811231;第29卷(第1期);第45页示意图和第48页倒数第三段 * |
Also Published As
| Publication number | Publication date |
|---|---|
| US20170305957A1 (en) | 2017-10-26 |
| AU2012372640A1 (en) | 2014-09-25 |
| WO2013131305A1 (zh) | 2013-09-12 |
| EP2889303A4 (en) | 2016-02-17 |
| CN103626817A (zh) | 2014-03-12 |
| TW201336861A (zh) | 2013-09-16 |
| EP3112374A1 (en) | 2017-01-04 |
| CA2909998A1 (en) | 2013-09-12 |
| CN103626818B (zh) | 2016-03-30 |
| RU2608894C2 (ru) | 2017-01-26 |
| US20150045566A1 (en) | 2015-02-12 |
| CN103626817B (zh) | 2016-01-20 |
| AU2012372640B2 (en) | 2015-07-09 |
| CN103626818A (zh) | 2014-03-12 |
| EP2889303A1 (en) | 2015-07-01 |
| CN102617685A (zh) | 2012-08-01 |
| CN102617685B (zh) | 2014-01-22 |
| US9944672B2 (en) | 2018-04-17 |
| RU2014136891A (ru) | 2016-05-10 |
| US9688716B2 (en) | 2017-06-27 |
| SG11201405376TA (en) | 2014-11-27 |
| CA2866398A1 (en) | 2013-09-12 |
| CN103626819A (zh) | 2014-03-12 |
| US9944673B2 (en) | 2018-04-17 |
| JP2015511587A (ja) | 2015-04-20 |
| IL234492A (en) | 2017-02-28 |
| IN2014DN08198A (https=) | 2015-05-01 |
| US20170305958A1 (en) | 2017-10-26 |
| CA2866398C (en) | 2016-06-28 |
| KR20150002653A (ko) | 2015-01-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | 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 | ||
| C56 | Change in the name or address of the patentee | ||
| CP03 | Change of name, title or address |
Address after: The city on 510663 Guangzhou Road, Guangdong province science No. 3 Guangzhou International Business Incubator Building G 401-415 Patentee after: GUANGZHOU SAIPUTE PHARMACEUTICAL TECHNOLOGY CO., LTD. Address before: 510663 Guangdong city of Guangzhou province high tech Industrial Development Zone of Guangzhou Science City skim Springs Road No. 3, Guangzhou international business incubator C C208 Patentee before: Guangzhou Saipute Medical Technology Co., Ltd. |