KR920004488B1 - 1-히드록시비타민 d 화합물의 제조방법 - Google Patents
1-히드록시비타민 d 화합물의 제조방법 Download PDFInfo
- Publication number
- KR920004488B1 KR920004488B1 KR1019860700400A KR860700400A KR920004488B1 KR 920004488 B1 KR920004488 B1 KR 920004488B1 KR 1019860700400 A KR1019860700400 A KR 1019860700400A KR 860700400 A KR860700400 A KR 860700400A KR 920004488 B1 KR920004488 B1 KR 920004488B1
- Authority
- KR
- South Korea
- Prior art keywords
- cyclovitamin
- hydroxy
- compound
- mixture
- hydroxyvitamin
- 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
- 150000001875 compounds Chemical class 0.000 title claims description 41
- 238000000034 method Methods 0.000 title claims description 26
- 239000000203 mixture Substances 0.000 claims description 39
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 12
- -1 phenyl-substituted maleimide Chemical class 0.000 claims description 12
- 238000004587 chromatography analysis Methods 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
- 239000011976 maleic acid Substances 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- 239000003125 aqueous solvent Substances 0.000 claims description 2
- YTIVTFGABIZHHX-UHFFFAOYSA-N butynedioic acid Chemical class OC(=O)C#CC(O)=O YTIVTFGABIZHHX-UHFFFAOYSA-N 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 238000000638 solvent extraction Methods 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 239000011710 vitamin D Substances 0.000 description 11
- 229940046008 vitamin d Drugs 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229930003316 Vitamin D Natural products 0.000 description 9
- 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 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 235000019166 vitamin D Nutrition 0.000 description 9
- OFHCOWSQAMBJIW-AVJTYSNKSA-N alfacalcidol 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)C[C@H](O)C1=C OFHCOWSQAMBJIW-AVJTYSNKSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 5
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 5
- 150000003710 vitamin D derivatives Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 238000005805 hydroxylation reaction Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 230000007928 solubilization Effects 0.000 description 3
- 238000005063 solubilization Methods 0.000 description 3
- 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 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical group 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000003797 solvolysis reaction Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- FCKJYANJHNLEEP-XRWYNYHCSA-N (24R)-24,25-dihydroxycalciol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CC[C@@H](O)C(C)(C)O)C)=C\C=C1\C[C@@H](O)CCC1=C FCKJYANJHNLEEP-XRWYNYHCSA-N 0.000 description 1
- USVVENVKYJZFMW-ONEGZZNKSA-N (e)-carboxyiminocarbamic acid Chemical compound OC(=O)\N=N\C(O)=O USVVENVKYJZFMW-ONEGZZNKSA-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
- ZGLHBRQAEXKACO-XJRQOBMKSA-N 1alpha,25-dihydroxyvitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](\C=C\[C@H](C)C(C)(C)O)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C ZGLHBRQAEXKACO-XJRQOBMKSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- JWUBBDSIWDLEOM-NQZHSCJISA-N 25-hydroxy-3 epi cholecalciferol Chemical group 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
- KJKIIUAXZGLUND-ICCVIKJNSA-N 25-hydroxyvitamin D2 Chemical group C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](\C=C\[C@H](C)C(C)(C)O)C)=C\C=C1\C[C@@H](O)CCC1=C KJKIIUAXZGLUND-ICCVIKJNSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000218645 Cedrus Species 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000005103 alkyl silyl group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 238000013475 authorization Methods 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000033558 biomineral tissue development Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- HKXBNHCUPKIYDM-CGMHZMFXSA-N doxercalciferol 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)C[C@H](O)C1=C HKXBNHCUPKIYDM-CGMHZMFXSA-N 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000013632 homeostatic process Effects 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 150000002689 maleic acids Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000037345 metabolism of vitamins Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003431 steroids Chemical group 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 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
- 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
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 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
- MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical class 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US667296 | 1984-11-01 | ||
| US06/667,296 US4555364A (en) | 1984-11-01 | 1984-11-01 | Method for preparing 1-hydroxyvitamin D compounds |
| PCT/US1985/001995 WO1986002649A1 (en) | 1984-11-01 | 1985-10-15 | Method for preparing 1-hydroxyvitamin d compounds |
| US667,296 | 1991-03-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR860700353A KR860700353A (ko) | 1986-10-06 |
| KR920004488B1 true KR920004488B1 (ko) | 1992-06-05 |
Family
ID=24677643
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019860700400A Expired KR920004488B1 (ko) | 1984-11-01 | 1985-10-15 | 1-히드록시비타민 d 화합물의 제조방법 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4555364A (enExample) |
| EP (1) | EP0198892B1 (enExample) |
| JP (1) | JPS62500717A (enExample) |
| KR (1) | KR920004488B1 (enExample) |
| AU (1) | AU589580B2 (enExample) |
| CA (1) | CA1233187A (enExample) |
| DE (1) | DE3581200D1 (enExample) |
| DK (1) | DK153943C (enExample) |
| IE (1) | IE58164B1 (enExample) |
| IL (1) | IL76754A (enExample) |
| NZ (1) | NZ213844A (enExample) |
| WO (1) | WO1986002649A1 (enExample) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5602116A (en) * | 1988-08-02 | 1997-02-11 | Bone Care International, Inc. | Method for treating and preventing secondary hyperparathyroidism |
| US5869473A (en) * | 1988-08-02 | 1999-02-09 | Bone Care International, Inc. | Method for treating and preventing hyperparathyroidism |
| CA1333616C (en) * | 1989-03-09 | 1994-12-20 | Hector F. Deluca | 19-nor-vitamin d compounds |
| NZ232734A (en) * | 1989-03-09 | 1991-11-26 | Wisconsin Alumni Res Found | 19-nor vitamin d derivatives and pharmaceutical compositions |
| US5246925A (en) * | 1989-03-09 | 1993-09-21 | Wisconsin Alumni Research Foundation | 19-nor-vitamin D compounds for use in treating hyperparathyroidism |
| US5801164A (en) * | 1990-09-21 | 1998-09-01 | Bone Care International, Inc. | Methods of treating osteoporosis prophylactically or therapeutically |
| US5798345A (en) * | 1990-09-21 | 1998-08-25 | Bone Care International, Inc. | Method of inhibiting the hyperproliferation of malignant cells |
| US5763428A (en) * | 1990-09-21 | 1998-06-09 | Bone Care International, Inc. | Methods of treating skin disorders with novel 1a-hydroxy vitamin D4 compounds and derivatives thereof |
| US6025346A (en) * | 1990-09-21 | 2000-02-15 | Bone Care International, Inc. | 1α-hydroxy vitamin D4 and novel intermediates and analogues |
| US20040009958A1 (en) * | 1991-01-08 | 2004-01-15 | Bone Care International, Inc. | Methods for preparation and use of 1alpha,24(S)-dihydroxyvitamin D2 |
| US5763429A (en) * | 1993-09-10 | 1998-06-09 | Bone Care International, Inc. | Method of treating prostatic diseases using active vitamin D analogues |
| US6121469A (en) * | 1993-12-23 | 2000-09-19 | The Regents Of The University Of California | Therapeutically effective 1α,25-dihydroxyvitamin D3 analogs |
| US5869472A (en) * | 1994-07-18 | 1999-02-09 | Bone Care International, Inc. | Synthesis of 1α-hydroxy vitamin D |
| US6376479B1 (en) | 1995-04-03 | 2002-04-23 | Bone Care International, Inc. | Method for treating and preventing hyperparathyroidism |
| US20040043971A1 (en) * | 1995-04-03 | 2004-03-04 | Bone Care International, Inc. | Method of treating and preventing hyperparathyroidism with active vitamin D analogs |
| US20020183288A1 (en) * | 1995-04-03 | 2002-12-05 | Bone Care International, Inc. | Method for treating and preventing hyperparathyroidism |
| US6242434B1 (en) | 1997-08-08 | 2001-06-05 | Bone Care International, Inc. | 24-hydroxyvitamin D, analogs and uses thereof |
| US6566353B2 (en) | 1996-12-30 | 2003-05-20 | Bone Care International, Inc. | Method of treating malignancy associated hypercalcemia using active vitamin D analogues |
| US6573256B2 (en) | 1996-12-30 | 2003-06-03 | Bone Care International, Inc. | Method of inhibiting angiogenesis using active vitamin D analogues |
| US6503893B2 (en) | 1996-12-30 | 2003-01-07 | Bone Care International, Inc. | Method of treating hyperproliferative diseases using active vitamin D analogues |
| US20030129194A1 (en) * | 1997-02-13 | 2003-07-10 | Bone Care International, Inc. | Targeted therapeutic delivery of vitamin D compounds |
| CA2279590A1 (en) * | 1997-02-13 | 1998-08-20 | Bone Care International, Inc. | Targeted therapeutic delivery of vitamin d compounds |
| US5972917A (en) * | 1998-05-29 | 1999-10-26 | Bone Care Int Inc | 1 α-hydroxy-25-ene-vitamin D, analogs and uses thereof |
| EP2070911A2 (en) * | 2000-07-18 | 2009-06-17 | Bone Care International, Inc. | Stabilized 1Alpha-Hydroxy vitamin D |
| US20040053895A1 (en) * | 2002-09-18 | 2004-03-18 | Bone Care International, Inc. | Multi-use vessels for vitamin D formulations |
| US7148211B2 (en) | 2002-09-18 | 2006-12-12 | Genzyme Corporation | Formulation for lipophilic agents |
| US20050239756A1 (en) * | 2004-04-23 | 2005-10-27 | Bone Care International, Inc. | Methods of treating various vitamin D metabolism conditions with 1alpha-hydroxyvitamin D2 |
| US7094775B2 (en) | 2004-06-30 | 2006-08-22 | Bone Care International, Llc | Method of treating breast cancer using a combination of vitamin D analogues and other agents |
| JP5303276B2 (ja) * | 2005-10-12 | 2013-10-02 | プロヴェンティヴ セラピュティックス リミテッド ライアビリティ カンパニー | ２５−ヒドロキシビタミンｄ不足および欠乏を治療するための方法および製品 |
| CA2882048C (en) * | 2006-02-03 | 2020-03-24 | Proventiv Therapeutics, Llc | Treating vitamin d insufficiency and deficiency with 25-hydroxyvitamin d2 and 25-hydroxyvitamin d3 |
| EP2679228B1 (en) | 2006-06-21 | 2018-03-21 | Opko Ireland Global Holdings, Ltd. | Therapy using vitamin D repletion agent and vitamin D hormone replacement agent |
| KR101759244B1 (ko) | 2007-04-25 | 2017-07-18 | 사이토크로마 인코포레이티드 | 비타민 ｄ 화합물과 밀랍성 담체를 포함하는 경구 조절성 방출 조성물 |
| US8592401B2 (en) * | 2007-04-25 | 2013-11-26 | Proventiv Therapeutics, Llc | Methods and compounds for vitamin D therapy |
| EP3225243B1 (en) | 2007-04-25 | 2025-09-03 | Opko Renal, LLC | Method of safely and effectively treating and preventing secondary hyperparathyroidism in chronic kidney disease |
| WO2009047644A2 (en) * | 2007-04-25 | 2009-04-16 | Cytochroma Inc. | Method of treating vitamin d insufficiency and deficiency |
| CN106853250A (zh) | 2008-04-02 | 2017-06-16 | 赛特克罗公司 | 用于维生素d缺乏症和相关障碍的方法、组合物、用途和试剂盒 |
| SI2552484T1 (sl) | 2010-03-29 | 2020-07-31 | Opko Ireland Global Holdings, Ltd. | Postopki in sestavki za znižanje ravni paratiroidnega hormona |
| KR101847947B1 (ko) | 2013-03-15 | 2018-05-28 | 옵코 아이피 홀딩스 Ⅱ 인코포레이티드 | 안정화되고 변형된 비타민 ｄ 방출 제형 |
| US10220047B2 (en) | 2014-08-07 | 2019-03-05 | Opko Ireland Global Holdings, Ltd. | Adjunctive therapy with 25-hydroxyvitamin D and articles therefor |
| CA3018019A1 (en) | 2016-03-28 | 2017-10-26 | Opko Ireland Global Holdings, Limited | Methods of vitamin d treatment |
| CN117126090A (zh) * | 2023-09-01 | 2023-11-28 | 正大制药（青岛）有限公司 | 一种骨化醇类原料药5,6-trans杂质的除杂方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4195027A (en) * | 1978-01-16 | 1980-03-25 | Wisconsin Alumni Research Foundation | Process for preparing 1α-hydroxylated compounds |
| US4234495A (en) * | 1979-09-10 | 1980-11-18 | Wisconsin Alumni Research Foundation | Process for preparing 1α-hydroxyvitamin D compounds from 1α-hydroxy-3,5-cyclovitamin D compounds |
| US4367177A (en) * | 1981-04-15 | 1983-01-04 | Wisconsin Alumni Research Foundation | Process for preparing 23,25-dihydroxyvitamin D3 |
| US4512925A (en) * | 1983-09-14 | 1985-04-23 | Wisconsin Alumini Research Foundation | 1,23-Dihydroxyvitamin D compounds |
| US4554106A (en) * | 1984-11-01 | 1985-11-19 | Wisconsin Alumni Research Foundation | Method for preparing 1α-hydroxyvitamin D compounds |
-
1984
- 1984-11-01 US US06/667,296 patent/US4555364A/en not_active Expired - Lifetime
-
1985
- 1985-10-15 KR KR1019860700400A patent/KR920004488B1/ko not_active Expired
- 1985-10-15 JP JP60504750A patent/JPS62500717A/ja active Granted
- 1985-10-15 DE DE8585905353T patent/DE3581200D1/de not_active Expired - Lifetime
- 1985-10-15 EP EP85905353A patent/EP0198892B1/en not_active Expired - Lifetime
- 1985-10-15 AU AU48674/85A patent/AU589580B2/en not_active Expired
- 1985-10-15 WO PCT/US1985/001995 patent/WO1986002649A1/en not_active Ceased
- 1985-10-16 NZ NZ213844A patent/NZ213844A/xx unknown
- 1985-10-18 CA CA000493353A patent/CA1233187A/en not_active Expired
- 1985-10-18 IL IL76754A patent/IL76754A/xx not_active IP Right Cessation
- 1985-11-01 IE IE270685A patent/IE58164B1/en not_active IP Right Cessation
-
1986
- 1986-06-26 DK DK301986A patent/DK153943C/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0198892B1 (en) | 1990-12-27 |
| IL76754A0 (en) | 1986-02-28 |
| DK301986A (da) | 1986-06-26 |
| DK301986D0 (da) | 1986-06-26 |
| AU589580B2 (en) | 1989-10-19 |
| IE852706L (en) | 1986-05-01 |
| JPS62500717A (ja) | 1987-03-26 |
| KR860700353A (ko) | 1986-10-06 |
| US4555364A (en) | 1985-11-26 |
| DK153943B (da) | 1988-09-26 |
| NZ213844A (en) | 1989-08-29 |
| JPH0432062B2 (enExample) | 1992-05-28 |
| DK153943C (da) | 1989-01-30 |
| EP0198892A4 (en) | 1987-03-12 |
| DE3581200D1 (de) | 1991-02-07 |
| CA1233187A (en) | 1988-02-23 |
| WO1986002649A1 (en) | 1986-05-09 |
| AU4867485A (en) | 1986-05-15 |
| IE58164B1 (en) | 1993-07-28 |
| IL76754A (en) | 1989-10-31 |
| EP0198892A1 (en) | 1986-10-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR920004488B1 (ko) | 1-히드록시비타민 d 화합물의 제조방법 | |
| EP0198901B1 (en) | Method for preparing 1alpha-hydroxyvitamin d compounds | |
| US4260549A (en) | Process for preparing 1α-hydroxylated compounds | |
| DE2954557C2 (enExample) | ||
| US4769181A (en) | 1,25-dihydroxyvitamin D2 compounds | |
| KR900008120B1 (ko) | 비타민 d₃유도체의 제조방법 | |
| HU210032B (en) | Process for the production of 24-homo-d-vitamin derivatives and pharmaceutical compositions containing the same | |
| IE50195B1 (en) | Process for preparing 1alpha-hydroxyvitamin d compounds from 1alpha-hydroxy-3,5-cyclovitamin d compounds | |
| US5030772A (en) | Process for preparing vitamin D2 compounds and the corresponding 1 α-hydroxylated derivatives | |
| US5250523A (en) | Side chain unsaturated 1α-hydroxyvitanim D homologs | |
| FR2517677A1 (fr) | Nouveaux ethers dont les restes organiques comportent des atomes chiraux, leur procede de preparation et leur application au dedoublement des alcools ou de certains composes de structure hemiacetalique. | |
| GB2217716A (en) | Vitamin d homologs | |
| US5354744A (en) | Side chain unsaturated 1 alpha-hydroxyvitamin D analogs | |
| US5036061A (en) | Process for the preparation of 1 alpha,25-dihydroxylated vitamin D2 and related compounds | |
| KR950008970B1 (ko) | t-부틸 에르골린 유도체의 제조방법 | |
| WO1988003527A1 (fr) | Reduction cetonique amelioree d'intermediaires de carbacycline | |
| IE44292B1 (en) | Cyclopentanol derivatives | |
| EP0404936B1 (en) | Preparation of vitamin d2 and vitamin d3, or active vitamin d2 and active vitamin d3, or their derivatives | |
| IL97163A (en) | Preparation of appropriate vitamin D2 compounds and A-hydroxy history | |
| Okamura et al. | Studies on vitamin D (calciferol) and its analogs. 13. 3-Deoxy-3. alpha.-methyl-1. alpha.-hydroxyvitamin D3, 3-deoxy-3. alpha.-methyl-1. alpha., 25-dihydroxyvitamin D3, and 1. alpha.-hydroxy-3-epivitamin D3. Analogs with conformationally biased a rings | |
| JPS5988429A (ja) | 有機過酸による酸化方法 | |
| EP0753510A1 (de) | Verfahren zur Herstellung von 9,10-Secocholesta-5,7,10(19)-trienen | |
| JPH04211052A (ja) | ビタミンＤ２ 化合物及び対応の１α−ヒドロキシル化誘導体の製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19860628 |
|
| PG1501 | Laying open of application | ||
| A201 | Request for examination | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 19900731 Comment text: Request for Examination of Application Patent event code: PA02011R01I Patent event date: 19860628 Comment text: Patent Application |
|
| G160 | Decision to publish patent application | ||
| PG1605 | Publication of application before grant of patent |
Comment text: Decision on Publication of Application Patent event code: PG16051S01I Patent event date: 19920506 |
|
| E701 | Decision to grant or registration of patent right | ||
| PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 19920826 |
|
| GRNT | Written decision to grant | ||
| PR0701 | Registration of establishment |
Comment text: Registration of Establishment Patent event date: 19921005 Patent event code: PR07011E01D |
|
| PR1002 | Payment of registration fee |
Payment date: 19921005 End annual number: 3 Start annual number: 1 |
|
| PR1001 | Payment of annual fee |
Payment date: 19950517 Start annual number: 4 End annual number: 4 |
|
| J206 | Request for trial to confirm the scope of a patent right | ||
| PJ0206 | Trial to confirm the scope of a patent |
Patent event code: PJ02062R01D Patent event date: 19960412 Comment text: Request for Trial Patent event code: PJ02061E01I Patent event date: 19921005 Comment text: Registration of Establishment Decision date: 19980131 Request date: 19960412 Appeal identifier: 1996100000431 Appeal kind category: Confirmation of the scope of right_defensive |
|
| PR1001 | Payment of annual fee |
Payment date: 19960517 Start annual number: 5 End annual number: 5 |
|
| PR1001 | Payment of annual fee |
Payment date: 19970527 Start annual number: 6 End annual number: 6 |
|
| J2X1 | Appeal (before the patent court) |
Free format text: CONFIRMATION OF THE SCOPE OF RIGHT |
|
| PJ2001 | Appeal |
Appeal kind category: Confirmation of the scope of right Decision date: 19980616 Appeal identifier: 1998200003644 Request date: 19980320 |
|
| PR1001 | Payment of annual fee |
Payment date: 19980526 Start annual number: 7 End annual number: 7 |
|
| PR1001 | Payment of annual fee |
Payment date: 19990518 Start annual number: 8 End annual number: 8 |
|
| PR1001 | Payment of annual fee |
Payment date: 20000531 Start annual number: 9 End annual number: 9 |
|
| PR1001 | Payment of annual fee |
Payment date: 20010530 Start annual number: 10 End annual number: 10 |
|
| PR1001 | Payment of annual fee |
Payment date: 20020521 Start annual number: 11 End annual number: 11 |
|
| PR1001 | Payment of annual fee |
Payment date: 20030522 Start annual number: 12 End annual number: 12 |
|
| PR1001 | Payment of annual fee |
Payment date: 20040524 Start annual number: 13 End annual number: 13 |
|
| FPAY | Annual fee payment |
Payment date: 20050524 Year of fee payment: 14 |
|
| PR1001 | Payment of annual fee |
Payment date: 20050524 Start annual number: 14 End annual number: 14 |
|
| EXPY | Expiration of term | ||
| PC1801 | Expiration of term |