DE05715124T1 - Neues verfahren zur herstellung von für die synthese von vitamin-d-analoga geeigneten zwischenprodukten - Google Patents
Neues verfahren zur herstellung von für die synthese von vitamin-d-analoga geeigneten zwischenprodukten Download PDFInfo
- Publication number
- DE05715124T1 DE05715124T1 DE05715124T DE05715124T DE05715124T1 DE 05715124 T1 DE05715124 T1 DE 05715124T1 DE 05715124 T DE05715124 T DE 05715124T DE 05715124 T DE05715124 T DE 05715124T DE 05715124 T1 DE05715124 T1 DE 05715124T1
- Authority
- DE
- Germany
- Prior art keywords
- general structure
- compound
- hydrogen
- aralkyl
- hydroxy
- 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 claims abstract 5
- 238000003786 synthesis reaction Methods 0.000 title claims abstract 5
- 239000000543 intermediate Substances 0.000 title 1
- 238000004519 manufacturing process 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 140
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 57
- 238000000034 method Methods 0.000 claims abstract 45
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 38
- 125000000217 alkyl group Chemical group 0.000 claims abstract 38
- 125000000304 alkynyl group Chemical group 0.000 claims abstract 38
- 125000003118 aryl group Chemical group 0.000 claims abstract 38
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract 38
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract 38
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims abstract 20
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 19
- 238000002360 preparation method Methods 0.000 claims abstract 19
- 125000001424 substituent group Chemical group 0.000 claims abstract 19
- 229930003316 Vitamin D Natural products 0.000 claims abstract 8
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products 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-XFEUOLMDSA-N 0.000 claims abstract 8
- 229910052799 carbon Inorganic materials 0.000 claims abstract 8
- 239000012634 fragment Substances 0.000 claims abstract 8
- 235000019166 vitamin D Nutrition 0.000 claims abstract 8
- 239000011710 vitamin D Substances 0.000 claims abstract 8
- 150000003710 vitamin D derivatives Chemical class 0.000 claims abstract 8
- 229940046008 vitamin d Drugs 0.000 claims abstract 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract 4
- 150000001721 carbon Chemical group 0.000 claims abstract 4
- 239000002243 precursor Substances 0.000 claims abstract 4
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 61
- 229910052739 hydrogen Inorganic materials 0.000 claims 59
- 239000001257 hydrogen Substances 0.000 claims 59
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 48
- 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 45
- 125000006239 protecting group Chemical group 0.000 claims 40
- 229960002882 calcipotriol Drugs 0.000 claims 27
- -1 carboxy, sulfo Chemical group 0.000 claims 24
- 239000000203 mixture Substances 0.000 claims 24
- 239000002585 base Substances 0.000 claims 21
- 125000003545 alkoxy group Chemical group 0.000 claims 18
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 18
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 18
- 125000004043 oxo group Chemical group O=* 0.000 claims 18
- 229910052736 halogen Inorganic materials 0.000 claims 15
- 150000002367 halogens Chemical class 0.000 claims 15
- 150000002431 hydrogen Chemical class 0.000 claims 11
- 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 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 9
- 239000003638 chemical reducing agent Substances 0.000 claims 8
- 239000003960 organic solvent Substances 0.000 claims 8
- 230000002341 photoisomerizing effect Effects 0.000 claims 7
- 230000000640 hydroxylating effect Effects 0.000 claims 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 239000003153 chemical reaction reagent Substances 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- 238000010438 heat treatment Methods 0.000 claims 3
- 239000003223 protective agent Substances 0.000 claims 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 claims 2
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 238000006546 Horner-Wadsworth-Emmons reaction Methods 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 125000005103 alkyl silyl group Chemical group 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- MJUJXFBTEFXVKU-UHFFFAOYSA-N diethyl phosphonate Chemical compound CCOP(=O)OCC MJUJXFBTEFXVKU-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 239000003444 phase transfer catalyst Substances 0.000 claims 1
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- 0 C[C@@]([C@@](CC1)([C@@](C)(CCC2)[C@]1(*)C2=CC=C(C[C@](CC1)O*I)C1=C)I)C=O Chemical compound C[C@@]([C@@](CC1)([C@@](C)(CCC2)[C@]1(*)C2=CC=C(C[C@](CC1)O*I)C1=C)I)C=O 0.000 description 8
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B37/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving either the formation of a carbon-to-carbon bond between two carbon atoms not directly linked already or the disconnection of two directly linked carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C401/00—Irradiation products of cholesterol or its derivatives; Vitamin D derivatives, 9,10-seco cyclopenta[a]phenanthrene or analogues obtained by chemical preparation without irradiation
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55854604P | 2004-04-02 | 2004-04-02 | |
| US558546P | 2004-04-02 | ||
| PCT/DK2005/000203 WO2005095336A2 (en) | 2004-04-02 | 2005-03-23 | Novel method for the preparation of intermediates useful for the synthesis of vitamin d analogues |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE05715124T1 true DE05715124T1 (de) | 2008-02-21 |
Family
ID=34961754
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE05715124T Pending DE05715124T1 (de) | 2004-04-02 | 2005-03-23 | Neues verfahren zur herstellung von für die synthese von vitamin-d-analoga geeigneten zwischenprodukten |
| DE602005026378T Expired - Lifetime DE602005026378D1 (de) | 2004-04-02 | 2005-03-23 | Neues verfahren zur herstellung von für die synthese von vitamin-d-analoga geeigneten zwischenprodukten |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE602005026378T Expired - Lifetime DE602005026378D1 (de) | 2004-04-02 | 2005-03-23 | Neues verfahren zur herstellung von für die synthese von vitamin-d-analoga geeigneten zwischenprodukten |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US20070135395A1 (enExample) |
| EP (1) | EP1735276B1 (enExample) |
| JP (1) | JP4744507B2 (enExample) |
| KR (1) | KR20070056001A (enExample) |
| CN (1) | CN1938268B (enExample) |
| AR (1) | AR048462A1 (enExample) |
| AT (1) | ATE498609T1 (enExample) |
| BR (1) | BRPI0508704A (enExample) |
| CA (1) | CA2561590C (enExample) |
| DE (2) | DE05715124T1 (enExample) |
| ES (1) | ES2361389T3 (enExample) |
| IL (1) | IL177357A (enExample) |
| MX (1) | MXPA06010824A (enExample) |
| MY (1) | MY146099A (enExample) |
| RU (1) | RU2378252C2 (enExample) |
| TW (1) | TWI322800B (enExample) |
| UA (1) | UA94568C2 (enExample) |
| WO (1) | WO2005095336A2 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1948283B (zh) * | 2005-10-14 | 2010-12-29 | 台耀化学股份有限公司 | 维生素d衍生物的制备方法 |
| BRPI0621471A2 (pt) * | 2006-03-17 | 2012-09-11 | Leo Pharma As | métodos de isomerização de uma solução de um derivado de vitamina d, para produzir e preparar calcipotriol ou monoidrato de calcipotriol, e para a fabricação de uma formulação farmacêutica ou medicamento, e, uso de um reator foto-reator de fluxo direto ou foto-reator de fluxo contìnuo |
| WO2009057136A2 (en) * | 2007-08-03 | 2009-05-07 | Glenmark Generics Limited | Epimerization by stereoselective synthesis of vitamin d analogues |
| WO2009153782A1 (en) * | 2008-06-17 | 2009-12-23 | Ben Gurion University Of The Negev R&D Authority | Substituted cyclohexylidene-ethylidene-octahydro-indene compounds |
| WO2011002756A2 (en) * | 2009-07-01 | 2011-01-06 | Vitamin Derivatives, Inc. | Vitamin d compounds and methods for preparing same |
| CN101607932B (zh) * | 2009-07-23 | 2012-05-09 | 青岛正大海尔制药有限公司 | 一种光化学反应制备骨化三醇的方法及其装置 |
| CN103980172A (zh) * | 2014-04-26 | 2014-08-13 | 湖南华腾制药有限公司 | 一种1α,25-二羟基维生素D2的制备方法 |
| CN103980173A (zh) * | 2014-04-26 | 2014-08-13 | 湖南华腾制药有限公司 | 一种帕立骨化醇中间体的制备方法 |
| CN105624215B (zh) * | 2014-10-27 | 2020-10-27 | 天津金耀集团有限公司 | 一种卡泊三醇合成新方法 |
| CN104447211A (zh) * | 2014-12-12 | 2015-03-25 | 重庆华邦制药有限公司 | 维生素d类药物的中间体化合物及制备方法 |
| CN105777665B (zh) * | 2014-12-17 | 2018-11-06 | 上虞京新药业有限公司 | 卡泊三醇的中间体化合物及其制备方法 |
| ES2575744B1 (es) * | 2014-12-30 | 2017-02-09 | Laboratorios Viñas S.A. | Procedimiento para proteger derivados de vitamina D con SO2 y uso correspondiente |
| CN106905358B (zh) * | 2015-12-23 | 2020-12-01 | 重庆华邦胜凯制药有限公司 | 一种制备维生素d3类似物中间体的方法 |
| CN105717206B (zh) * | 2016-01-27 | 2018-02-06 | 重庆华邦制药有限公司 | 分离测定卡泊三醇中间体f及其杂质的方法 |
| 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 |
| ES2674336B1 (es) * | 2016-12-28 | 2019-04-11 | Laboratorios Vinas S A | Procedimiento para reducir derivados carbonilicos de vitamina d y uso correspondiente |
| CN113845541B (zh) * | 2021-10-19 | 2023-11-07 | 重庆华邦胜凯制药有限公司 | 一种制备维生素d3类似物的方法 |
| CN116396268A (zh) * | 2021-12-27 | 2023-07-07 | 上海信谊万象药业股份有限公司 | 一种阿法骨化醇中间体合成方法 |
Family Cites Families (7)
| 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 |
| US5244104A (en) * | 1992-01-02 | 1993-09-14 | Sias Equipment Company | Drying rack and spacer |
| US5247104A (en) * | 1992-11-04 | 1993-09-21 | Wisconsin Alumni Research Foundation | Preparation of 1α, 24-dihydroxyvitamin D analogs |
| JPH08325226A (ja) * | 1995-05-30 | 1996-12-10 | Teijin Ltd | ビタミンｄ３ 誘導体の製造法 |
| PL376148A1 (en) * | 2002-10-23 | 2005-12-27 | Leo Pharma A/S | Vitamin d analogues, compositions comprising said analogues and their use |
| ES2233209B1 (es) * | 2003-11-28 | 2006-04-01 | Laboratorios Viñas S.A. | Compuestos monohalogenovinilderivados de vitamina d. |
| JP4667450B2 (ja) * | 2004-03-18 | 2011-04-13 | レオ ファーマ アクティーゼルスカブ | ビタミンｄ類似体の立体選択的合成 |
-
2005
- 2005-03-23 RU RU2006138613/04A patent/RU2378252C2/ru active
- 2005-03-23 CA CA002561590A patent/CA2561590C/en not_active Expired - Fee Related
- 2005-03-23 BR BRPI0508704-0A patent/BRPI0508704A/pt not_active IP Right Cessation
- 2005-03-23 JP JP2007505379A patent/JP4744507B2/ja not_active Expired - Fee Related
- 2005-03-23 ES ES05715124T patent/ES2361389T3/es not_active Expired - Lifetime
- 2005-03-23 KR KR1020067022977A patent/KR20070056001A/ko not_active Abandoned
- 2005-03-23 CN CN200580009943XA patent/CN1938268B/zh not_active Expired - Fee Related
- 2005-03-23 DE DE05715124T patent/DE05715124T1/de active Pending
- 2005-03-23 AT AT05715124T patent/ATE498609T1/de active
- 2005-03-23 DE DE602005026378T patent/DE602005026378D1/de not_active Expired - Lifetime
- 2005-03-23 EP EP05715124A patent/EP1735276B1/en not_active Expired - Lifetime
- 2005-03-23 MX MXPA06010824A patent/MXPA06010824A/es active IP Right Grant
- 2005-03-23 WO PCT/DK2005/000203 patent/WO2005095336A2/en not_active Ceased
- 2005-03-23 US US10/588,800 patent/US20070135395A1/en not_active Abandoned
- 2005-03-23 UA UAA200611527A patent/UA94568C2/ru unknown
- 2005-03-25 MY MYPI20051315A patent/MY146099A/en unknown
- 2005-04-01 AR ARP050101304A patent/AR048462A1/es unknown
- 2005-04-01 TW TW094110536A patent/TWI322800B/zh not_active IP Right Cessation
-
2006
- 2006-08-08 IL IL177357A patent/IL177357A/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| TWI322800B (en) | 2010-04-01 |
| WO2005095336A2 (en) | 2005-10-13 |
| MY146099A (en) | 2012-06-29 |
| CN1938268A (zh) | 2007-03-28 |
| DE602005026378D1 (de) | 2011-03-31 |
| KR20070056001A (ko) | 2007-05-31 |
| EP1735276A2 (en) | 2006-12-27 |
| CA2561590C (en) | 2008-11-18 |
| AR048462A1 (es) | 2006-04-26 |
| JP2007530602A (ja) | 2007-11-01 |
| RU2378252C2 (ru) | 2010-01-10 |
| HK1098124A1 (en) | 2007-07-13 |
| US20070135395A1 (en) | 2007-06-14 |
| EP1735276B1 (en) | 2011-02-16 |
| CA2561590A1 (en) | 2005-10-13 |
| UA94568C2 (ru) | 2011-05-25 |
| BRPI0508704A (pt) | 2007-08-07 |
| ATE498609T1 (de) | 2011-03-15 |
| RU2006138613A (ru) | 2008-05-10 |
| CN1938268B (zh) | 2010-06-02 |
| IL177357A (en) | 2008-04-13 |
| JP4744507B2 (ja) | 2011-08-10 |
| WO2005095336A3 (en) | 2005-11-10 |
| TW200613257A (en) | 2006-05-01 |
| ES2361389T3 (es) | 2011-06-16 |
| MXPA06010824A (es) | 2007-01-17 |
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