JPH0113711B2 - - Google Patents
Info
- Publication number
- JPH0113711B2 JPH0113711B2 JP1436482A JP1436482A JPH0113711B2 JP H0113711 B2 JPH0113711 B2 JP H0113711B2 JP 1436482 A JP1436482 A JP 1436482A JP 1436482 A JP1436482 A JP 1436482A JP H0113711 B2 JPH0113711 B2 JP H0113711B2
- Authority
- JP
- Japan
- Prior art keywords
- hydroxyvitamin
- vitamin
- peroxylactone
- hplc
- shows
- 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
Links
- JWUBBDSIWDLEOM-NQZHSCJISA-N 25-hydroxy-3 epi cholecalciferol Chemical compound C1([C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(C)O)C)=CC=C1C[C@H](O)CCC1=C JWUBBDSIWDLEOM-NQZHSCJISA-N 0.000 claims description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 238000004128 high performance liquid chromatography Methods 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 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 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000001819 mass spectrum Methods 0.000 description 9
- 241000700159 Rattus Species 0.000 description 8
- DBDDUVJJIVBQPI-WWBRWCDLSA-N 4-hydroxy-6-[2-[(4e)-4-[(2z)-2-(5-hydroxy-2-methylidenecyclohexylidene)ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1h-inden-1-yl]propyl]-4-methyldioxan-3-one Chemical compound C1CC2\C(=C\C=C\3C(CCC(O)C/3)=C)CCCC2(C)C1C(C)CC1CC(C)(O)C(=O)OO1 DBDDUVJJIVBQPI-WWBRWCDLSA-N 0.000 description 7
- 239000011647 vitamin D3 Substances 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 6
- 239000008280 blood Substances 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- IJNDMZIDDKVXHR-MYEQSZOMSA-N 25-Hydroxyvitamin D3-26,23-lactone Chemical group C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C/1C(CC[C@@H](O)C\1)=C)C)[C@@H]1C[C@@](C)(O)C(=O)O1 IJNDMZIDDKVXHR-MYEQSZOMSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 150000002596 lactones Chemical class 0.000 description 4
- 239000002207 metabolite Substances 0.000 description 4
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 238000002211 ultraviolet spectrum Methods 0.000 description 3
- 241000287828 Gallus gallus Species 0.000 description 2
- 241000282887 Suidae Species 0.000 description 2
- 210000000702 aorta abdominal Anatomy 0.000 description 2
- 150000001793 charged compounds Chemical class 0.000 description 2
- 235000013330 chicken meat Nutrition 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 150000005671 trienes Chemical group 0.000 description 2
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 2
- 150000003704 vitamin D3 derivatives Chemical class 0.000 description 2
- NPHAVLULUWJQAS-UHFFFAOYSA-N 5,5-dimethyloxolan-2-one Chemical compound CC1(C)CCC(=O)O1 NPHAVLULUWJQAS-UHFFFAOYSA-N 0.000 description 1
- 241000725101 Clea Species 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 235000021590 normal diet Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000010421 standard material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000005282 vitamin D3 Nutrition 0.000 description 1
- 229940021056 vitamin d3 Drugs 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1436482A JPS58131980A (ja) | 1982-02-02 | 1982-02-02 | ２５−ヒドロキシビタミンｄ３−２６，２３−パ−オキシラクトン |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1436482A JPS58131980A (ja) | 1982-02-02 | 1982-02-02 | ２５−ヒドロキシビタミンｄ３−２６，２３−パ−オキシラクトン |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58131980A JPS58131980A (ja) | 1983-08-06 |
| JPH0113711B2 true JPH0113711B2 (enExample) | 1989-03-07 |
Family
ID=11858998
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1436482A Granted JPS58131980A (ja) | 1982-02-02 | 1982-02-02 | ２５−ヒドロキシビタミンｄ３−２６，２３−パ−オキシラクトン |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58131980A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4663247A (en) * | 1985-11-04 | 1987-05-05 | Union Carbide Corporation | Coiled electrode assembly cell construction with pressure contact member |
-
1982
- 1982-02-02 JP JP1436482A patent/JPS58131980A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58131980A (ja) | 1983-08-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4927815A (en) | Compounds effective in inducing cell differentiation and process for preparing same | |
| JP4511838B2 (ja) | （２０Ｓ）−１α−ヒドロキシ−２α−メチル及び２β−メチル−１９−ノル−ビタミンＤ３及びそれらの使用 | |
| Ishizuka et al. | Isolation and identification of 1. alpha., 25-dihydroxy-24-oxovitamin D3, 1. alpha., 25-dihydroxyvitamin D3 26, 23-lactone, and 1. alpha., 24 (S), 25-trihydroxyvitamin D3: in vivo metabolites of 1. alpha., 25-dihydroxyvitamin D3 | |
| JPS60502153A (ja) | ２３，２３−ジフルオロ−１α，２５−ジヒドロキシ−ビタミンＤ↓３ | |
| JP5009617B2 (ja) | ２−メチレン−１９−ノル−ビタミンｄ２化合物 | |
| JPH10509715A (ja) | １８，１９−ジノル−ビタミンｄ 化合物 | |
| KR900008120B1 (ko) | 비타민 d₃유도체의 제조방법 | |
| WO1999003829A1 (en) | 18-substituted-19-nor-vitamin d compounds | |
| US3728363A (en) | Quinone derivatives | |
| US7241747B2 (en) | 2-propylidene-19-nor-vitamin D compounds | |
| IE57935B1 (en) | Hydroxyvitamin d2 isomers | |
| JPS6342618B2 (enExample) | ||
| JPH0314303B2 (enExample) | ||
| HUP9904333A2 (hu) | D-vitamin-analógok, eljárás előállításukra és ezeket tartalmazó gyógyszerkészítmények | |
| JP3917184B2 (ja) | ２５―ヒドロキシ―１６―エン―２６，２７―ビスホモ―コレカルシフェロール類 | |
| US20010051617A1 (en) | 18-substituted-19-nor-vitamin D compounds | |
| US4360471A (en) | 23-Dehydro-25-hydroxyvitamin D3 | |
| IE67953B1 (en) | Side Chain Unsaturated 1alpha-Hydroxyvitamin D Homologs | |
| CN100402497C (zh) | 氟代维生素d3类似物 | |
| JPH05178887A (ja) | １α，３β，２５−トリヒドロキシ−２４−ホモコレスタ−５，７−ジエン類似体 | |
| Barycki et al. | Removal of the 20-methyl group from 2-methylene-19-nor-(20S)-1α, 25-dihydroxyvitamin D3 (2MD) selectively eliminates bone calcium mobilization activity | |
| US5036061A (en) | Process for the preparation of 1 alpha,25-dihydroxylated vitamin D2 and related compounds | |
| JPH0376304B2 (enExample) | ||
| NL8202832A (nl) | Steroiden met anti-aldosteronwerking. | |
| Van Gool et al. | Vitamin D: Enantioselective Synthesis of (3aR, 4R, 7aS)‐4‐Hydroxy‐7a‐methylperhydro‐1‐indenone, a Suitable CD‐Ring Fragment |