JPS63500033A - １α―ヒドロキシビタミンＤ化合物の中間体の調製方法 - Google Patents
１α―ヒドロキシビタミンＤ化合物の中間体の調製方法Info
- Publication number
- JPS63500033A JPS63500033A JP61503063A JP50306386A JPS63500033A JP S63500033 A JPS63500033 A JP S63500033A JP 61503063 A JP61503063 A JP 61503063A JP 50306386 A JP50306386 A JP 50306386A JP S63500033 A JPS63500033 A JP S63500033A
- Authority
- JP
- Japan
- Prior art keywords
- group
- hydroxy
- hydrogen
- compound
- formula
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 31
- OFHCOWSQAMBJIW-AVJTYSNKSA-N alfacalcidol Chemical class C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C OFHCOWSQAMBJIW-AVJTYSNKSA-N 0.000 title description 6
- 239000000543 intermediate Substances 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims description 40
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 150000001299 aldehydes Chemical class 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical group FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 claims description 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
- 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 description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound 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 claims description 4
- 150000002009 diols Chemical group 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 235000012000 cholesterol Nutrition 0.000 claims description 2
- HALQELOKLVRWRI-VDBOFHIQSA-N doxycycline hyclate Chemical group O.[Cl-].[Cl-].CCO.O=C1C2=C(O)C=CC=C2[C@H](C)[C@@H]2C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H]([NH+](C)C)[C@@H]1[C@H]2O.O=C1C2=C(O)C=CC=C2[C@H](C)[C@@H]2C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H]([NH+](C)C)[C@@H]1[C@H]2O HALQELOKLVRWRI-VDBOFHIQSA-N 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 claims 1
- RQOCXCFLRBRBCS-UHFFFAOYSA-N (22E)-cholesta-5,7,22-trien-3beta-ol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CCC(C)C)CCC33)C)C3=CC=C21 RQOCXCFLRBRBCS-UHFFFAOYSA-N 0.000 claims 1
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- DNVPQKQSNYMLRS-NXVQYWJNSA-N Ergosterol Natural products CC(C)[C@@H](C)C=C[C@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@H]3CC[C@]12C DNVPQKQSNYMLRS-NXVQYWJNSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229910021386 carbon form Inorganic materials 0.000 claims 1
- DNVPQKQSNYMLRS-SOWFXMKYSA-N ergosterol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H](CC[C@]3([C@H]([C@H](C)/C=C/[C@@H](C)C(C)C)CC[C@H]33)C)C3=CC=C21 DNVPQKQSNYMLRS-SOWFXMKYSA-N 0.000 claims 1
- 150000004678 hydrides Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- -1 hydroxyethyl group Chemical group 0.000 description 12
- 230000008569 process Effects 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000000284 extract Substances 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 229930003316 Vitamin D Natural products 0.000 description 5
- 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 5
- 229910000489 osmium tetroxide Inorganic materials 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 235000019166 vitamin D Nutrition 0.000 description 5
- 239000011710 vitamin D Substances 0.000 description 5
- 150000003710 vitamin D derivatives Chemical class 0.000 description 5
- 229940046008 vitamin d Drugs 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000012285 osmium tetroxide Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 229930003231 vitamin Natural products 0.000 description 4
- 229940088594 vitamin Drugs 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012634 fragment Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 238000012552 review Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 239000011782 vitamin Substances 0.000 description 3
- 235000013343 vitamin Nutrition 0.000 description 3
- 150000003722 vitamin derivatives Chemical class 0.000 description 3
- ULDHMXUKGWMISQ-VIFPVBQESA-N (+)-carvone Chemical compound CC(=C)[C@H]1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-VIFPVBQESA-N 0.000 description 2
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- 208000035480 Ring chromosome 8 syndrome Diseases 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 230000021615 conjugation Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- GMRQFYUYWCNGIN-UHFFFAOYSA-N 1,25-Dihydroxy-vitamin D3' Natural products C1CCC2(C)C(C(CCCC(C)(C)O)C)CCC2C1=CC=C1CC(O)CC(O)C1=C GMRQFYUYWCNGIN-UHFFFAOYSA-N 0.000 description 1
- GMRQFYUYWCNGIN-ZVUFCXRFSA-N 1,25-dihydroxy vitamin D3 Chemical compound C1([C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(C)O)C)=CC=C1C[C@@H](O)C[C@H](O)C1=C GMRQFYUYWCNGIN-ZVUFCXRFSA-N 0.000 description 1
- JWUBBDSIWDLEOM-UHFFFAOYSA-N 25-Hydroxycholecalciferol Natural products C1CCC2(C)C(C(CCCC(C)(C)O)C)CCC2C1=CC=C1CC(O)CCC1=C JWUBBDSIWDLEOM-UHFFFAOYSA-N 0.000 description 1
- JWUBBDSIWDLEOM-DCHLRESJSA-N 25-Hydroxyvitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(C)O)C)=C/C=C1\C[C@@H](O)CCC1=C JWUBBDSIWDLEOM-DCHLRESJSA-N 0.000 description 1
- 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 description 1
- INBGSXNNRGWLJU-ZHHJOTBYSA-N 25-hydroxycholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@@H](CCCC(C)(C)O)C)[C@@]1(C)CC2 INBGSXNNRGWLJU-ZHHJOTBYSA-N 0.000 description 1
- INBGSXNNRGWLJU-UHFFFAOYSA-N 25epsilon-Hydroxycholesterin Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(CCCC(C)(C)O)C)C1(C)CC2 INBGSXNNRGWLJU-UHFFFAOYSA-N 0.000 description 1
- BDDLHHRCDSJVKV-UHFFFAOYSA-N 7028-40-2 Chemical compound CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O BDDLHHRCDSJVKV-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- OKMTZCDWZRFJKW-UHFFFAOYSA-N C(C)O[AlH2].[Na] Chemical compound C(C)O[AlH2].[Na] OKMTZCDWZRFJKW-UHFFFAOYSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 208000013725 Chronic Kidney Disease-Mineral and Bone disease Diseases 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 241000283715 Damaliscus lunatus Species 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- MECHNRXZTMCUDQ-UHFFFAOYSA-N Vitamin D2 Natural products C1CCC2(C)C(C(C)C=CC(C)C(C)C)CCC2C1=CC=C1CC(O)CCC1=C MECHNRXZTMCUDQ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 125000005103 alkyl silyl group Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- QLFNUXTWJGXNLH-UHFFFAOYSA-N bis(2-methoxyethoxy)alumane Chemical compound COCCO[AlH]OCCOC QLFNUXTWJGXNLH-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 230000000125 calcaemic effect Effects 0.000 description 1
- GMRQFYUYWCNGIN-NKMMMXOESA-N calcitriol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(C)O)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C GMRQFYUYWCNGIN-NKMMMXOESA-N 0.000 description 1
- 235000020964 calcitriol Nutrition 0.000 description 1
- 239000011612 calcitriol Substances 0.000 description 1
- 230000004094 calcium homeostasis Effects 0.000 description 1
- 230000003913 calcium metabolism Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229960002061 ergocalciferol Drugs 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- XUFQPHANEAPEMJ-UHFFFAOYSA-N famotidine Chemical compound NC(N)=NC1=NC(CSCCC(N)=NS(N)(=O)=O)=CS1 XUFQPHANEAPEMJ-UHFFFAOYSA-N 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- QKGYJVXSKCDGOK-UHFFFAOYSA-N hexane;propan-2-ol Chemical compound CC(C)O.CCCCCC QKGYJVXSKCDGOK-UHFFFAOYSA-N 0.000 description 1
- 230000013632 homeostatic process Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229930003658 monoterpene Natural products 0.000 description 1
- 150000002773 monoterpene derivatives Chemical class 0.000 description 1
- 235000002577 monoterpenes Nutrition 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 208000005368 osteomalacia Diseases 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 201000006409 renal osteodystrophy Diseases 0.000 description 1
- 208000007442 rickets Diseases 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 150000005671 trienes Chemical class 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000001892 vitamin D2 Nutrition 0.000 description 1
- 239000011653 vitamin D2 Substances 0.000 description 1
- MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 0.000 description 1
- 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 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/296—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with lead derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
- C07C35/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings
- C07C35/32—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings the condensed ring system being a (4.3.0) system, e.g. indenols
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/26—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing hydroxy groups
- C07C47/267—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing hydroxy groups containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/277—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US743129 | 1985-06-10 | ||
| US06/743,129 US4755329A (en) | 1985-06-10 | 1985-06-10 | Process and intermediates for preparing 1α-hydroxyvitamin D compounds |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4283646A Division JPH0662558B2 (ja) | 1985-06-10 | 1992-09-30 | １α，７，８−トリヒドロキシビタミンＤ化合物 |
| JP8028614A Division JP2741497B2 (ja) | 1985-06-10 | 1996-01-23 | １α−ヒドロキシビタミンＤ化合物の中間体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63500033A true JPS63500033A (ja) | 1988-01-07 |
| JPH0523251B2 JPH0523251B2 (enExample) | 1993-04-02 |
Family
ID=24987631
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61503063A Granted JPS63500033A (ja) | 1985-06-10 | 1986-05-20 | １α―ヒドロキシビタミンＤ化合物の中間体の調製方法 |
| JP4283646A Expired - Lifetime JPH0662558B2 (ja) | 1985-06-10 | 1992-09-30 | １α，７，８−トリヒドロキシビタミンＤ化合物 |
| JP8028614A Expired - Lifetime JP2741497B2 (ja) | 1985-06-10 | 1996-01-23 | １α−ヒドロキシビタミンＤ化合物の中間体 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4283646A Expired - Lifetime JPH0662558B2 (ja) | 1985-06-10 | 1992-09-30 | １α，７，８−トリヒドロキシビタミンＤ化合物 |
| JP8028614A Expired - Lifetime JP2741497B2 (ja) | 1985-06-10 | 1996-01-23 | １α−ヒドロキシビタミンＤ化合物の中間体 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4755329A (enExample) |
| EP (1) | EP0225915A4 (enExample) |
| JP (3) | JPS63500033A (enExample) |
| AU (1) | AU598469B2 (enExample) |
| CA (1) | CA1304389C (enExample) |
| DK (1) | DK54787D0 (enExample) |
| GB (1) | GB2178424B (enExample) |
| IE (1) | IE58441B1 (enExample) |
| WO (1) | WO1986007364A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6447739A (en) * | 1987-08-19 | 1989-02-22 | Nissan Chemical Ind Ltd | Optically active liquid crystal compound |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5283345A (en) * | 1988-03-09 | 1994-02-01 | Hoxan Corporation | 1β,7,8-trihydroxy vitamin D2, 1∘,7,8-trihydroxy vitamin D3 and their derivatives and method of manufacturing these chemicals |
| JPH0667896B2 (ja) * | 1988-03-09 | 1994-08-31 | 大同ほくさん株式会社 | １β，７，８―トリヒドロキシビタミンＤ２若しくはＤ３またはそれらの誘導体、およびそれらの製造方法 |
| US5789397A (en) * | 1991-01-08 | 1998-08-04 | Bone Care International, Inc. | Methods for preparation and use of 1A,24(S)-dihydroxy vitamin D2 |
| US20040009958A1 (en) * | 1991-01-08 | 2004-01-15 | Bone Care International, Inc. | Methods for preparation and use of 1alpha,24(S)-dihydroxyvitamin D2 |
| AU650751B2 (en) * | 1991-05-28 | 1994-06-30 | Wisconsin Alumni Research Foundation | Novel synthesis of 19-nor vitamin D compounds |
| DK0521550T3 (da) * | 1991-07-05 | 1996-11-04 | Duphar Int Res | Vitamin D forbindelse, fremgangsmåde til fremstilling af denne forbindelse og mellemprodukt derfor |
| US5300705A (en) * | 1993-03-18 | 1994-04-05 | Hoffmann-La Roche Inc. | Process for the preparation of 1α,25,26-trihydroxy-22-ene-cholecalciferol |
| SG173119A1 (en) * | 2009-01-27 | 2011-08-29 | Berg Biosystems Llc | Vitamin d3 and analogs thereof for alleviating side effects associated with chemotherapy |
| SG178382A1 (en) | 2009-08-14 | 2012-04-27 | Berg Biosystems Llc | Vitamin d3 and analogs thereof for treating alopecia |
| NZ714801A (en) | 2013-05-29 | 2021-07-30 | Berg Llc | Preventing or mitigating chemotherapy induced alopecia using vitamin d |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59212466A (ja) * | 1983-05-11 | 1984-12-01 | ウイスコンシン アラムナイ リサ−チ フオンデ−シヨン | 環ａ―及びトリエン―修飾３，５―シクロビタミンｄ化合物 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4225596A (en) * | 1978-10-13 | 1980-09-30 | Wisconsin Alumni Research Foundation | Method for treating calcium imbalance and improving calcium absorption in mammals |
| US4594432A (en) * | 1983-01-28 | 1986-06-10 | Hoffman-La Roche Inc. | Process for the synthesis of 1α,23(S),25-trihydroxycholecalciferol and 1α,23(R),25-trihydroxycholecalciferol |
| US4594340A (en) * | 1984-11-29 | 1986-06-10 | Hoffmann-La Roche Inc. | 25,26-dehydro-1α,24R-dihydroxycholecalciferol and 25,26-dehydro-1α,24S-dihydroxycholecalciferol and the epimeric mixture |
-
1985
- 1985-06-10 US US06/743,129 patent/US4755329A/en not_active Expired - Lifetime
-
1986
- 1986-05-20 JP JP61503063A patent/JPS63500033A/ja active Granted
- 1986-05-20 AU AU59511/86A patent/AU598469B2/en not_active Expired
- 1986-05-20 EP EP19860903850 patent/EP0225915A4/en not_active Withdrawn
- 1986-05-20 WO PCT/US1986/001088 patent/WO1986007364A1/en not_active Ceased
- 1986-05-23 CA CA000509865A patent/CA1304389C/en not_active Expired - Lifetime
- 1986-06-09 IE IE152686A patent/IE58441B1/en not_active IP Right Cessation
- 1986-06-09 GB GB8613945A patent/GB2178424B/en not_active Expired
-
1987
- 1987-02-03 DK DK054787A patent/DK54787D0/da not_active Application Discontinuation
-
1992
- 1992-09-30 JP JP4283646A patent/JPH0662558B2/ja not_active Expired - Lifetime
-
1996
- 1996-01-23 JP JP8028614A patent/JP2741497B2/ja not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59212466A (ja) * | 1983-05-11 | 1984-12-01 | ウイスコンシン アラムナイ リサ−チ フオンデ−シヨン | 環ａ―及びトリエン―修飾３，５―シクロビタミンｄ化合物 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6447739A (en) * | 1987-08-19 | 1989-02-22 | Nissan Chemical Ind Ltd | Optically active liquid crystal compound |
Also Published As
| Publication number | Publication date |
|---|---|
| AU5951186A (en) | 1987-01-07 |
| JPH0662558B2 (ja) | 1994-08-17 |
| EP0225915A1 (en) | 1987-06-24 |
| IE58441B1 (en) | 1993-09-22 |
| WO1986007364A1 (en) | 1986-12-18 |
| JPH0523251B2 (enExample) | 1993-04-02 |
| JPH05271182A (ja) | 1993-10-19 |
| CA1304389C (en) | 1992-06-30 |
| JP2741497B2 (ja) | 1998-04-15 |
| JPH08259479A (ja) | 1996-10-08 |
| GB2178424B (en) | 1989-07-26 |
| DK54787A (da) | 1987-02-03 |
| GB8613945D0 (en) | 1986-07-16 |
| DK54787D0 (da) | 1987-02-03 |
| GB2178424A (en) | 1987-02-11 |
| EP0225915A4 (en) | 1987-08-12 |
| US4755329A (en) | 1988-07-05 |
| AU598469B2 (en) | 1990-06-28 |
| IE861526L (en) | 1986-12-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3494637B2 (ja) | １９−ノル−ビタミンｄ化合物の中間体の製造方法 | |
| KR940010767B1 (ko) | 신규 비타민 d 동족체 | |
| FR2529888A1 (fr) | Composes 1a-hydroxyles | |
| US4554105A (en) | Process for the preparation of 1-hydroxylated vitamin D compounds | |
| JPS63500033A (ja) | １α―ヒドロキシビタミンＤ化合物の中間体の調製方法 | |
| Burger et al. | Allenic cholesteryl derivatives as inhibitors of ecdysone biosynthesis | |
| JP2804606B2 (ja) | 付加物―アルデヒドおよびビタミン―ｄ化合物の調製のためのその使用 | |
| JPS63107964A (ja) | プロビタミンｄまたはタキステロール化合物とジエノフィルとの付加物およびその製造方法 | |
| US5767111A (en) | 18-nor-vitamin D compounds | |
| JP3228488B2 (ja) | ２０−エピステロイド誘導体およびその製造方法 | |
| US5087709A (en) | Process for the preparation of 1α,25-dihydroxyvitamin D2 and the 24-epimer thereof | |
| RU2317992C2 (ru) | Новые промежуточные соединения для синтеза производных витамина d | |
| JPH0437074B2 (enExample) | ||
| JP3588367B2 (ja) | １β−ヒドロキシ−１α−低級アルキルビタミンＤ誘導体 | |
| JP2826168B2 (ja) | ステロイド誘導体及びその製造方法 | |
| JP3712077B2 (ja) | ヒドロインダン−４−オール誘導体およびその製造方法 | |
| JP2975704B2 (ja) | ステロイド誘導体 | |
| JPH05339230A (ja) | 活性型ビタミンｄ２及びその誘導体の製造法 | |
| JP2975705B2 (ja) | ステロイド誘導体 | |
| JP3228486B2 (ja) | ヒドロキシケトン誘導体およびその製造方法 | |
| JPS6314720B2 (enExample) | ||
| JPH0672928A (ja) | ７−オクチン−１−エン誘導体およびその製造方法 | |
| FR2558830A1 (fr) | 1-hydroxyvitamines d insaturees en chaine laterale, composition pharmaceutique et procede de preparation | |
| JPH06329622A (ja) | ヨードビタミンｄ３ 化合物類及びその調製方法 | |
| FR2550789A1 (fr) | 23,23-difluoro-25-hydroxy- et 1a,25-dihydroxy-vitamine d3 |