DE05706821T1 - Stereoselektive synthese von vitamin-d-analoga - Google Patents
Stereoselektive synthese von vitamin-d-analoga Download PDFInfo
- Publication number
- DE05706821T1 DE05706821T1 DE05706821T DE05706821T DE05706821T1 DE 05706821 T1 DE05706821 T1 DE 05706821T1 DE 05706821 T DE05706821 T DE 05706821T DE 05706821 T DE05706821 T DE 05706821T DE 05706821 T1 DE05706821 T1 DE 05706821T1
- Authority
- DE
- Germany
- Prior art keywords
- general structure
- compound
- hydrogen
- defined above
- mixture
- 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.)
- Pending
Links
- 230000015572 biosynthetic process Effects 0.000 title 1
- 230000000707 stereoselective effect Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 229940088594 vitamin Drugs 0.000 title 1
- 229930003231 vitamin Natural products 0.000 title 1
- 235000013343 vitamin Nutrition 0.000 title 1
- 239000011782 vitamin Substances 0.000 title 1
- 150000003722 vitamin derivatives Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 51
- 238000000034 method Methods 0.000 claims abstract 29
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 24
- 239000001257 hydrogen Substances 0.000 claims abstract 24
- 239000000203 mixture Substances 0.000 claims abstract 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 16
- 239000003638 chemical reducing agent Substances 0.000 claims abstract 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 10
- 125000006239 protecting group Chemical group 0.000 claims abstract 10
- 239000012442 inert solvent Substances 0.000 claims abstract 5
- XBKHACNRWFKJNC-MANNPBRJSA-N calcipotriol hydrate Chemical compound O.C1([C@H](O)/C=C/[C@@H](C)[C@@H]2[C@]3(CCCC(/[C@@H]3CC2)=C\C=C\2C([C@@H](O)C[C@H](O)C/2)=C)C)CC1 XBKHACNRWFKJNC-MANNPBRJSA-N 0.000 claims 15
- 229960002882 calcipotriol Drugs 0.000 claims 9
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 230000000640 hydroxylating effect Effects 0.000 claims 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- LWQQLNNNIPYSNX-UROSTWAQSA-N calcipotriol Chemical compound C1([C@H](O)/C=C/[C@@H](C)[C@@H]2[C@]3(CCCC(/[C@@H]3CC2)=C\C=C\2C([C@@H](O)C[C@H](O)C/2)=C)C)CC1 LWQQLNNNIPYSNX-UROSTWAQSA-N 0.000 claims 3
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 125000005103 alkyl silyl group Chemical group 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- LOPKSXMQWBYUOI-DTWKUNHWSA-N (1r,2s)-1-amino-2,3-dihydro-1h-inden-2-ol Chemical class C1=CC=C2[C@@H](N)[C@@H](O)CC2=C1 LOPKSXMQWBYUOI-DTWKUNHWSA-N 0.000 claims 1
- LOPKSXMQWBYUOI-BDAKNGLRSA-N (1s,2r)-1-amino-2,3-dihydro-1h-inden-2-ol Chemical compound C1=CC=C2[C@H](N)[C@H](O)CC2=C1 LOPKSXMQWBYUOI-BDAKNGLRSA-N 0.000 claims 1
- 150000000179 1,2-aminoalcohols Chemical class 0.000 claims 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 1
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical class [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims 1
- MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 claims 1
- KHYAFFAGZNCWPT-UHFFFAOYSA-N boron;n,n-diethylaniline Chemical compound [B].CCN(CC)C1=CC=CC=C1 KHYAFFAGZNCWPT-UHFFFAOYSA-N 0.000 claims 1
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 150000004682 monohydrates Chemical class 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/72—Benzo[c]thiophenes; Hydrogenated benzo[c]thiophenes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dermatology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55396204P | 2004-03-18 | 2004-03-18 | |
| US553962P | 2004-03-18 | ||
| DKPA200400454 | 2004-03-22 | ||
| DK200400454 | 2004-03-22 | ||
| PCT/DK2005/000161 WO2005087719A1 (en) | 2004-03-18 | 2005-03-10 | Stereoselective synthesis of vitamin d analogues |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE05706821T1 true DE05706821T1 (de) | 2008-02-07 |
Family
ID=34961016
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE05706821T Pending DE05706821T1 (de) | 2004-03-18 | 2005-03-10 | Stereoselektive synthese von vitamin-d-analoga |
| DE602005005645T Expired - Lifetime DE602005005645T2 (de) | 2004-03-18 | 2005-03-10 | Stereoselektive synthese von vitamin-d-analoga |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE602005005645T Expired - Lifetime DE602005005645T2 (de) | 2004-03-18 | 2005-03-10 | Stereoselektive synthese von vitamin-d-analoga |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP1730108B1 (https=) |
| JP (1) | JP4667450B2 (https=) |
| KR (1) | KR100859277B1 (https=) |
| CN (1) | CN1934078B (https=) |
| AR (1) | AR048274A1 (https=) |
| AT (1) | ATE390411T1 (https=) |
| BR (1) | BRPI0507318A (https=) |
| CA (1) | CA2555260C (https=) |
| CY (1) | CY1108156T1 (https=) |
| DE (2) | DE05706821T1 (https=) |
| ES (1) | ES2304686T3 (https=) |
| IL (1) | IL176718A (https=) |
| PL (1) | PL1730108T3 (https=) |
| RU (1) | RU2380359C2 (https=) |
| SI (1) | SI1730108T1 (https=) |
| TW (1) | TWI324063B (https=) |
| WO (1) | WO2005087719A1 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA94568C2 (ru) * | 2004-04-02 | 2011-05-25 | Лео Фарма А/С | Способ получения промежуточных соединений, которые применяют для синтеза аналогов витамина d |
| EP1844010B1 (en) | 2006-03-17 | 2013-02-13 | Leo Pharma A/S | Isomerisation of pharmaceutical intermediates |
| US8013189B2 (en) * | 2007-09-21 | 2011-09-06 | Basf Se | Accelerated amide and ester reductions with amine boranes and additives |
| WO2009153782A1 (en) * | 2008-06-17 | 2009-12-23 | Ben Gurion University Of The Negev R&D Authority | Substituted cyclohexylidene-ethylidene-octahydro-indene compounds |
| CN103265528B (zh) * | 2013-05-10 | 2015-05-06 | 湖南千金湘江药业股份有限公司 | 埃索美拉唑镁的制备方法 |
| CN106908524B (zh) * | 2015-12-23 | 2021-05-04 | 重庆华邦胜凯制药有限公司 | 卡泊三醇中间体l及其潜在基因毒性杂质的分离与测定方法 |
| CN107643354B (zh) * | 2016-07-22 | 2022-02-01 | 重庆华邦胜凯制药有限公司 | 卡泊三醇起始原料a及相关杂质的分离与测定方法 |
| ES2945426B2 (es) * | 2021-12-30 | 2024-01-22 | Laboratorios Vinas S A | Procedimiento para obtener epímeros 24S a partir de derivados de vitaminas D y procedimiento de obtención de vitaminas D relacionado |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07100685B2 (ja) * | 1985-08-02 | 1995-11-01 | レオ・ファ−マシュ−ティカル・プロダクツ・リミテッド・エイ／エス（レ−ベンス・ケミスケ・ファブリック・プロデュクチオンスアクチ−セルスカブ） | 新規ビタミンｄ類似体 |
| JPH075542B2 (ja) * | 1988-09-14 | 1995-01-25 | 呉羽化学工業株式会社 | ビタミンｄ▲下３▼誘導体及びその製造方法 |
| US5247104A (en) * | 1992-11-04 | 1993-09-21 | Wisconsin Alumni Research Foundation | Preparation of 1α, 24-dihydroxyvitamin D analogs |
| GB9300763D0 (en) * | 1993-01-15 | 1993-03-03 | Leo Pharm Prod Ltd | Chemical compound |
| US5449668A (en) * | 1993-06-04 | 1995-09-12 | Duphar International Research B.V. | Vitamin D compounds and method of preparing these compounds |
| GB9524812D0 (en) * | 1995-12-05 | 1996-02-07 | Leo Pharm Prod Ltd | Chemical compounds |
| GB9622590D0 (en) * | 1996-10-30 | 1997-01-08 | Leo Pharm Prod Ltd | Chemical compounds |
| US6262283B1 (en) * | 1996-12-06 | 2001-07-17 | Magainin Pharmaceuticals Inc. | Stereoselective synthesis of 24-hydroxylated compounds useful for the preparation of aminosterols, vitamin D analogs, and other compounds |
| AU758792B2 (en) * | 1998-10-23 | 2003-03-27 | Teijin Limited | Vitamin D3 derivatives and remedies for inflammatory respiratory diseases containing the same |
-
2005
- 2005-03-10 AT AT05706821T patent/ATE390411T1/de active
- 2005-03-10 BR BRPI0507318-9A patent/BRPI0507318A/pt not_active IP Right Cessation
- 2005-03-10 RU RU2006129922/04A patent/RU2380359C2/ru active
- 2005-03-10 DE DE05706821T patent/DE05706821T1/de active Pending
- 2005-03-10 JP JP2007503195A patent/JP4667450B2/ja not_active Expired - Fee Related
- 2005-03-10 WO PCT/DK2005/000161 patent/WO2005087719A1/en not_active Ceased
- 2005-03-10 CA CA2555260A patent/CA2555260C/en not_active Expired - Fee Related
- 2005-03-10 KR KR1020067015590A patent/KR100859277B1/ko not_active Expired - Fee Related
- 2005-03-10 ES ES05706821T patent/ES2304686T3/es not_active Expired - Lifetime
- 2005-03-10 EP EP05706821A patent/EP1730108B1/en not_active Expired - Lifetime
- 2005-03-10 PL PL05706821T patent/PL1730108T3/pl unknown
- 2005-03-10 CN CN2005800086209A patent/CN1934078B/zh not_active Expired - Fee Related
- 2005-03-10 DE DE602005005645T patent/DE602005005645T2/de not_active Expired - Lifetime
- 2005-03-10 SI SI200530248T patent/SI1730108T1/sl unknown
- 2005-03-16 TW TW094108053A patent/TWI324063B/zh not_active IP Right Cessation
- 2005-03-17 AR ARP050101046A patent/AR048274A1/es unknown
-
2006
- 2006-07-05 IL IL176718A patent/IL176718A/en active IP Right Grant
-
2008
- 2008-06-26 CY CY20081100667T patent/CY1108156T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| TWI324063B (en) | 2010-05-01 |
| CA2555260A1 (en) | 2005-09-22 |
| IL176718A (en) | 2007-07-04 |
| HK1098122A1 (en) | 2007-07-13 |
| EP1730108A1 (en) | 2006-12-13 |
| CN1934078B (zh) | 2011-07-06 |
| CN1934078A (zh) | 2007-03-21 |
| PL1730108T3 (pl) | 2008-09-30 |
| JP2007529433A (ja) | 2007-10-25 |
| BRPI0507318A (pt) | 2007-06-26 |
| WO2005087719A1 (en) | 2005-09-22 |
| RU2006129922A (ru) | 2008-02-27 |
| ATE390411T1 (de) | 2008-04-15 |
| EP1730108B1 (en) | 2008-03-26 |
| CA2555260C (en) | 2011-12-06 |
| DE602005005645D1 (de) | 2008-05-08 |
| ES2304686T3 (es) | 2008-10-16 |
| TW200539866A (en) | 2005-12-16 |
| SI1730108T1 (sl) | 2008-08-31 |
| KR20060134045A (ko) | 2006-12-27 |
| JP4667450B2 (ja) | 2011-04-13 |
| RU2380359C2 (ru) | 2010-01-27 |
| DE602005005645T2 (de) | 2009-06-18 |
| CY1108156T1 (el) | 2014-02-12 |
| AR048274A1 (es) | 2006-04-12 |
| KR100859277B1 (ko) | 2008-09-19 |
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