CN1227224C - 光化学方法 - Google Patents
光化学方法 Download PDFInfo
- Publication number
- CN1227224C CN1227224C CNB991086740A CN99108674A CN1227224C CN 1227224 C CN1227224 C CN 1227224C CN B991086740 A CNB991086740 A CN B991086740A CN 99108674 A CN99108674 A CN 99108674A CN 1227224 C CN1227224 C CN 1227224C
- Authority
- CN
- China
- Prior art keywords
- previtamin
- emitter
- dehydrocholesterol
- radiation
- photochemical
- 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.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 9
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 claims abstract description 16
- UCTLRSWJYQTBFZ-UHFFFAOYSA-N Dehydrocholesterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)CCCC(C)C)CCC33)C)C3=CC=C21 UCTLRSWJYQTBFZ-UHFFFAOYSA-N 0.000 claims abstract description 11
- YUGCAAVRZWBXEQ-WHTXLNIXSA-N previtamin D3 Chemical compound C=1([C@@H]2CC[C@@H]([C@]2(CCC=1)C)[C@H](C)CCCC(C)C)\C=C/C1=C(C)CC[C@H](O)C1 YUGCAAVRZWBXEQ-WHTXLNIXSA-N 0.000 claims abstract description 7
- 230000005855 radiation Effects 0.000 claims description 10
- 230000005281 excited state Effects 0.000 claims description 5
- 239000011647 vitamin D3 Substances 0.000 claims description 4
- 238000004220 aggregation Methods 0.000 claims description 2
- 230000002776 aggregation Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- YUGCAAVRZWBXEQ-UHFFFAOYSA-N Precholecalciferol Natural products C=1CCC2(C)C(C(C)CCCC(C)C)CCC2C=1C=CC1=C(C)CCC(O)C1 YUGCAAVRZWBXEQ-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000011552 falling film Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- UCTLRSWJYQTBFZ-DDPQNLDTSA-N cholesta-5,7-dien-3beta-ol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@H](C)CCCC(C)C)CC[C@H]33)C)C3=CC=C21 UCTLRSWJYQTBFZ-DDPQNLDTSA-N 0.000 description 4
- 238000000295 emission spectrum Methods 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000006862 quantum yield reaction Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- XQFJZHAVTPYDIQ-LETJEVNCSA-N (1s)-3-[(e)-2-[(1r,3ar,7ar)-1-[(e,2r,5r)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-1,2,3,3a,6,7-hexahydroinden-4-yl]ethenyl]-4-methylcyclohex-3-en-1-ol Chemical compound C=1([C@@H]2CC[C@@H]([C@]2(CCC=1)C)[C@H](C)/C=C/[C@H](C)C(C)C)\C=C\C1=C(C)CC[C@H](O)C1 XQFJZHAVTPYDIQ-LETJEVNCSA-N 0.000 description 1
- -1 acyloxy previtamin D3 Chemical compound 0.000 description 1
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical class C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- ILFGODHCYAHKOR-UHFFFAOYSA-N dibromoxenon Chemical compound Br[Xe]Br ILFGODHCYAHKOR-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- BUNBVCKYYMRTNS-UHFFFAOYSA-N tachysterol Natural products C=1CCC2(C)C(C(C)CCC(C)C(C)C)CCC2C=1C=CC1=C(C)CCC(O)C1 BUNBVCKYYMRTNS-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/59—Compounds containing 9, 10- seco- cyclopenta[a]hydrophenanthrene ring systems
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
- B01J19/12—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor employing electromagnetic waves
- B01J19/121—Coherent waves, e.g. laser beams
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Physics & Mathematics (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Toxicology (AREA)
- Electromagnetism (AREA)
- Organic Chemistry (AREA)
- Optics & Photonics (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98111492 | 1998-06-23 | ||
| EP98111492.9 | 1998-06-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1243123A CN1243123A (zh) | 2000-02-02 |
| CN1227224C true CN1227224C (zh) | 2005-11-16 |
Family
ID=8232158
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB991086740A Expired - Fee Related CN1227224C (zh) | 1998-06-23 | 1999-06-22 | 光化学方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6180805B1 (enExample) |
| EP (1) | EP0967202B1 (enExample) |
| JP (1) | JP2000026405A (enExample) |
| KR (1) | KR100682807B1 (enExample) |
| CN (1) | CN1227224C (enExample) |
| BR (1) | BR9903271A (enExample) |
| CA (1) | CA2275558A1 (enExample) |
| DE (1) | DE59905410D1 (enExample) |
| DK (1) | DK0967202T3 (enExample) |
| ES (1) | ES2197547T3 (enExample) |
| IN (1) | IN188477B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL140560A0 (en) | 1998-07-03 | 2002-02-10 | Chugai Pharmaceutical Co Ltd | Ultraviolet irradiation apparatus for photochemical reaction and preparation process of vitamin d derivatiive making use of the same |
| FR2823206B1 (fr) * | 2001-04-05 | 2004-02-20 | Atofina | Procede photochimique semi-continu et dispositif pour sa mise en oeuvre |
| WO2008128783A2 (en) * | 2007-04-24 | 2008-10-30 | Dsm Ip Assets B.V. | Photochemical process for the preparation of a previtamin d |
| CN101663269A (zh) * | 2007-04-24 | 2010-03-03 | 帝斯曼知识产权资产管理有限公司 | 用于制造前维生素d的光化学方法 |
| US20140221692A1 (en) | 2013-02-04 | 2014-08-07 | Chevron Phillips Chemical Company Lp | Flow Reactor Vessels and Reactor Systems |
| WO2015108058A1 (ja) * | 2014-01-17 | 2015-07-23 | 協和発酵バイオ株式会社 | ７デヒドロコレステロール及びビタミンｄ３の製造法 |
| WO2016056610A1 (ja) * | 2014-10-08 | 2016-04-14 | 協和発酵バイオ株式会社 | ７デヒドロコレステロール及びビタミンｄ３の製造法 |
| US12286454B2 (en) | 2019-05-10 | 2025-04-29 | Fermenta Biotech Limited | Irradiation process of pro vitamin D |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3270978D1 (en) * | 1981-07-17 | 1986-06-12 | Duphar Int Res | Method of preparing 1-alpha-hydroxyvitamin d and 1-alpha-hydroxy-previtamin d compounds, and adduct of a previtamin d or tachysterol compound with a suitable dienophile |
| US4388242A (en) * | 1982-03-15 | 1983-06-14 | Canadian Patents & Development Limited | Method of production of vitamin-D |
| DE3308592C2 (de) * | 1983-03-10 | 1986-08-07 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V., 3400 Göttingen | Photochemisches Verfahren zur Herstellung von Prävitamin D↓2↓ und D↓3↓ aus Ergosterin bzw.7-Dehydrocholesterin |
| DD279668A1 (de) * | 1984-10-15 | 1990-06-13 | Univ Schiller Jena | Verfahren zur sensibilisierten photoisomerisierung von 5.7-dien-steroiden |
| US4686023A (en) * | 1985-11-26 | 1987-08-11 | Solarchem Research, Division Of Brolor Investments, Ltd. | Sensitized photochemical preparation of vitamin D |
| US5543016A (en) * | 1991-07-12 | 1996-08-06 | Inrad | Photoconversion of steroids in microreactors |
| DE4136949A1 (de) * | 1991-11-11 | 1993-05-13 | Roswitha Niedermeier | Verfahren und vorrichtung zur photooxidativen reinigung von organisch belastetem wasser |
| DE59409236D1 (de) * | 1994-08-15 | 2000-04-27 | Sulzer Chemtech Ag Winterthur | Vorrichtung zum Behandeln von Fluiden mit UV-Strahlung |
-
1999
- 1999-05-07 IN IN657MA1999 patent/IN188477B/en unknown
- 1999-06-16 DE DE59905410T patent/DE59905410D1/de not_active Expired - Fee Related
- 1999-06-16 EP EP99111626A patent/EP0967202B1/de not_active Expired - Lifetime
- 1999-06-16 ES ES99111626T patent/ES2197547T3/es not_active Expired - Lifetime
- 1999-06-16 DK DK99111626T patent/DK0967202T3/da active
- 1999-06-18 CA CA002275558A patent/CA2275558A1/en not_active Abandoned
- 1999-06-22 BR BR9903271-6A patent/BR9903271A/pt not_active Application Discontinuation
- 1999-06-22 JP JP11175754A patent/JP2000026405A/ja active Pending
- 1999-06-22 KR KR1019990023456A patent/KR100682807B1/ko not_active Expired - Fee Related
- 1999-06-22 CN CNB991086740A patent/CN1227224C/zh not_active Expired - Fee Related
- 1999-06-23 US US09/338,784 patent/US6180805B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE59905410D1 (de) | 2003-06-12 |
| IN188477B (enExample) | 2002-09-28 |
| CN1243123A (zh) | 2000-02-02 |
| DK0967202T3 (da) | 2003-08-25 |
| EP0967202A1 (de) | 1999-12-29 |
| KR20000006343A (ko) | 2000-01-25 |
| BR9903271A (pt) | 2000-05-16 |
| ES2197547T3 (es) | 2004-01-01 |
| JP2000026405A (ja) | 2000-01-25 |
| KR100682807B1 (ko) | 2007-02-15 |
| EP0967202B1 (de) | 2003-05-07 |
| CA2275558A1 (en) | 1999-12-23 |
| US6180805B1 (en) | 2001-01-30 |
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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 | ||
| ASS | Succession or assignment of patent right |
Owner name: DSM IP ASSET CO., LTD. Free format text: FORMER OWNER: FUEL HA FUMAN-LALUOQI LTD. Effective date: 20040317 |
|
| C41 | Transfer of patent application or patent right or utility model | ||
| TA01 | Transfer of patent application right |
Effective date of registration: 20040317 Address after: Holland Heerlen Applicant after: D Sm I P Assets Limited Address before: Basel Applicant before: F. Hoffmann-La Roche AG |
|
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20051116 Termination date: 20180622 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |