JP5009992B2 - 結晶性3−o−置換されたアスコルビン酸の製造方法 - Google Patents
結晶性3−o−置換されたアスコルビン酸の製造方法 Download PDFInfo
- Publication number
- JP5009992B2 JP5009992B2 JP2009532274A JP2009532274A JP5009992B2 JP 5009992 B2 JP5009992 B2 JP 5009992B2 JP 2009532274 A JP2009532274 A JP 2009532274A JP 2009532274 A JP2009532274 A JP 2009532274A JP 5009992 B2 JP5009992 B2 JP 5009992B2
- Authority
- JP
- Japan
- Prior art keywords
- ascorbic acid
- substituted
- chemical formula
- producing
- exchange resin
- 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.)
- Active
Links
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 title claims abstract description 62
- 229960005070 ascorbic acid Drugs 0.000 title claims abstract description 54
- 239000011668 ascorbic acid Substances 0.000 title claims abstract description 50
- 235000010323 ascorbic acid Nutrition 0.000 title claims abstract description 46
- 238000004519 manufacturing process Methods 0.000 title claims description 18
- 125000003289 ascorbyl group Chemical class [H]O[C@@]([H])(C([H])([H])O*)[C@@]1([H])OC(=O)C(O*)=C1O* 0.000 title 1
- 239000003957 anion exchange resin Substances 0.000 claims abstract description 18
- 150000000996 L-ascorbic acids Chemical class 0.000 claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 10
- 239000003960 organic solvent Substances 0.000 claims abstract description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 12
- 150000001450 anions Chemical class 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- 238000010511 deprotection reaction Methods 0.000 claims description 5
- 125000002346 iodo group Chemical group I* 0.000 claims description 4
- 239000012046 mixed solvent Substances 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002366 halogen compounds Chemical class 0.000 claims description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- 239000011347 resin Substances 0.000 claims description 2
- 229920005989 resin Polymers 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- -1 iodo anion Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 9
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 230000008901 benefit Effects 0.000 abstract description 3
- 229910052740 iodine Inorganic materials 0.000 abstract description 3
- 239000011630 iodine Substances 0.000 abstract description 3
- 150000004820 halides Chemical class 0.000 abstract 1
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 229920000557 Nafion® Polymers 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- 229940120145 3-o-ethylascorbic acid Drugs 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000002211 L-ascorbic acid Substances 0.000 description 4
- 235000000069 L-ascorbic acid Nutrition 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 150000001350 alkyl halides Chemical class 0.000 description 4
- 238000005804 alkylation reaction Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- LEEANUDEDHYDTG-UHFFFAOYSA-N 1,2-dimethoxypropane Chemical compound COCC(C)OC LEEANUDEDHYDTG-UHFFFAOYSA-N 0.000 description 2
- ZGSCRDSBTNQPMS-UJURSFKZSA-N 3-O-Ethylascorbic acid Chemical compound CCOC1=C(O)C(=O)O[C@@H]1[C@@H](O)CO ZGSCRDSBTNQPMS-UJURSFKZSA-N 0.000 description 2
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 206010014970 Ephelides Diseases 0.000 description 1
- 208000003351 Melanosis Diseases 0.000 description 1
- 108010057081 Merozoite Surface Protein 1 Proteins 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 206010064127 Solar lentigo Diseases 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 206010047623 Vitamin C deficiency Diseases 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000036570 collagen biosynthesis Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 208000010233 scurvy Diseases 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 1
- 235000010378 sodium ascorbate Nutrition 0.000 description 1
- 229960005055 sodium ascorbate Drugs 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/62—Three oxygen atoms, e.g. ascorbic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Toxicology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Claims (6)
- 下記化学式1の3−O−置換されたアスコルビン酸の製造方法であって、
a)下記化学式2の5,6−O−イソプロピリデンアスコルビン酸を多ヨードアニオンが吸着されたアニオン交換樹脂の存在下において、化学式3のハロゲン化合物を有機溶媒で反応させて化学式4の3−O−置換−5,6−O−イソプロピリデンアスコルビン酸を製造する段階;と
b)製造された化学式4の3−O−置換−5,6−O−イソプロピリデンアスコルビン酸を脱保護化する段階;
とを備えていることを特徴とするアスコルビン酸の製造方法。
[化学式1]
[化学式2]
[化学式3]
[化学式4]
(前記式中、化学式1、化学式3及び化学式4のRはC1乃至C7のアルキルまたはアルケニル基であり、Xはハロゲン元素である。) - ヨードアニオンが吸着されたアニオン交換樹脂は、アルカリヨード化塩とヨード(I2)が1:1乃至5モル比で製造された多ヨードアニオン溶液に前記アニオン交換樹脂含有のポリマーを浸漬させて製造されたことを特徴とする請求項1に記載の3−O−置換されたアスコルビン酸の製造方法。
- ヨードアニオンが吸着されたアニオン交換樹脂は、3−O−置換−5,6−O−イソプロピリデンアスコルビン酸の0.5乃至5重量%であることを特徴とする請求項1に記載の3−O−置換されたアスコルビン酸の製造方法。
- a)段階における反応温度が常温乃至70℃であることを特徴とする請求項1に記載の3−O−置換されたアスコルビン酸の製造方法。
- a)段階において、有機溶媒はジメチルスルホキシド、ジメチルホルムアミド、メチルピロリドン、ジメチルアセトアミド、及び、アセトニトリルから選ばれる少なくとも1種であることを特徴とする請求項1に記載の3−O−置換されたアスコルビン酸の製造方法。
- b)段階の脱保護化はペルフルオロスルホン酸樹脂の存在下において、エタノールと水との混合溶媒で行われることを特徴とする請求項1に記載の3−O−置換されたアスコルビン酸の製造方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020060099554A KR100761959B1 (ko) | 2006-10-12 | 2006-10-12 | 결정성 3-o-치환된 아스코르빈산의 제조방법 |
KR10-2006-0099554 | 2006-10-12 | ||
PCT/KR2006/005274 WO2008044809A1 (en) | 2006-10-12 | 2006-12-07 | Method for preparing crystalline 3-0-alkyl-ascorbic acid |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2010506830A JP2010506830A (ja) | 2010-03-04 |
JP5009992B2 true JP5009992B2 (ja) | 2012-08-29 |
Family
ID=39282988
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2009532274A Active JP5009992B2 (ja) | 2006-10-12 | 2006-12-07 | 結晶性3−o−置換されたアスコルビン酸の製造方法 |
Country Status (9)
Country | Link |
---|---|
US (1) | US7838690B2 (ja) |
EP (1) | EP2081920B1 (ja) |
JP (1) | JP5009992B2 (ja) |
KR (1) | KR100761959B1 (ja) |
CN (1) | CN101528722B (ja) |
AT (1) | ATE498617T1 (ja) |
DE (1) | DE602006020196D1 (ja) |
ES (1) | ES2361189T3 (ja) |
WO (1) | WO2008044809A1 (ja) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101119027B1 (ko) * | 2009-05-07 | 2012-03-14 | (주)코스몰 | 아스코르빈산 유도체의 제조방법 |
KR101350540B1 (ko) | 2012-02-01 | 2014-01-14 | 주식회사 카이로켐 | 엘-3-오-알킬 아스코르빈산의 제조방법 |
CN105367524A (zh) * | 2015-06-19 | 2016-03-02 | 上海珈叶实业有限公司 | 3-o-烷基抗坏血酸的制备方法 |
CN110305085A (zh) * | 2019-07-23 | 2019-10-08 | 宁夏启元药业有限公司 | 3-o-乙基抗坏血酸醚的晶型a、其制备方法和美白组合物 |
CN110642816A (zh) * | 2019-09-25 | 2020-01-03 | 旖肽(上海)生物科技有限公司 | 结晶型3-o-乙基维生素c及其制备方法和应用 |
KR102325062B1 (ko) * | 2021-08-15 | 2021-11-11 | (주)삼양정밀화학 | 3-o-알킬-아스코르빈산의 제조방법 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5857373A (ja) | 1981-10-01 | 1983-04-05 | Sunstar Inc | L−アスコルビン酸誘導体の製法 |
US4552888A (en) * | 1982-01-15 | 1985-11-12 | Eli Lilly And Company | Ascorbic acid ethers in angiogene |
JPH0780865B2 (ja) * | 1986-09-06 | 1995-08-30 | 美浜 久春 | L−アスコルビン酸のレチノイルエステル |
KR940007418B1 (ko) * | 1991-03-05 | 1994-08-18 | 주식회사 태평양 | L-아스코빌-2-인산에스테르염 유도체 및 그의 제조방법 |
JP3253735B2 (ja) * | 1993-02-26 | 2002-02-04 | 日本サーファクタント工業株式会社 | アスコルビン酸誘導体 |
JPH08134055A (ja) * | 1994-11-08 | 1996-05-28 | Nippon High Potsukusu:Kk | 3−o−置換アスコルビン酸の製造方法 |
KR100500503B1 (ko) | 2001-05-30 | 2005-07-14 | (주)코스몰 | 결정성 3-0-알킬아스코르빈산의 제조방법 |
KR100548989B1 (ko) * | 2003-04-09 | 2006-02-08 | (주)코스몰 | 3-o-치환된-아스코르빈산의 제조방법 |
KR100600435B1 (ko) | 2005-02-05 | 2006-07-13 | 신호상 | 살균 폴리머의 새로운 제조방법 |
-
2006
- 2006-10-12 KR KR1020060099554A patent/KR100761959B1/ko active IP Right Grant
- 2006-12-07 CN CN2006800560755A patent/CN101528722B/zh active Active
- 2006-12-07 EP EP06823981A patent/EP2081920B1/en active Active
- 2006-12-07 US US12/444,821 patent/US7838690B2/en active Active
- 2006-12-07 DE DE602006020196T patent/DE602006020196D1/de active Active
- 2006-12-07 AT AT06823981T patent/ATE498617T1/de not_active IP Right Cessation
- 2006-12-07 ES ES06823981T patent/ES2361189T3/es active Active
- 2006-12-07 JP JP2009532274A patent/JP5009992B2/ja active Active
- 2006-12-07 WO PCT/KR2006/005274 patent/WO2008044809A1/en active Application Filing
Also Published As
Publication number | Publication date |
---|---|
CN101528722B (zh) | 2012-06-20 |
EP2081920A4 (en) | 2010-01-20 |
DE602006020196D1 (de) | 2011-03-31 |
WO2008044809A1 (en) | 2008-04-17 |
ES2361189T3 (es) | 2011-06-14 |
KR100761959B1 (ko) | 2007-10-04 |
JP2010506830A (ja) | 2010-03-04 |
ATE498617T1 (de) | 2011-03-15 |
US7838690B2 (en) | 2010-11-23 |
CN101528722A (zh) | 2009-09-09 |
US20100048919A1 (en) | 2010-02-25 |
EP2081920A1 (en) | 2009-07-29 |
EP2081920B1 (en) | 2011-02-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5009992B2 (ja) | 結晶性3−o−置換されたアスコルビン酸の製造方法 | |
JP7373598B2 (ja) | ジヌクレオシドポリリン酸化合物の製造方法 | |
CN103382160B (zh) | 碘帕醇的合成及其合成中间体的制备 | |
JP6225103B2 (ja) | 9−アザノルアダマンタンn−オキシル化合物及びその製造方法、並びに9−アザノルアダマンタンn−オキシル化合物を用いた有機分子酸化触媒及びアルコール類の酸化方法 | |
TWI462913B (zh) | 製備抗壞血酸衍生物之方法 | |
JP2005154379A (ja) | 4、4’−ジビニル置換芳香族化合物の製造方法 | |
JP3059007B2 (ja) | 1−(2−カルボキシフェニル)インダゾール誘導体の製造方法 | |
JP3176098B2 (ja) | ビス(4−アリルオキシ−3,5−ジブロモフェニル)スルホンの製造方法 | |
JP3924027B2 (ja) | オルソヒドロキシマンデル酸ナトリウム/フエノール/水錯体、その製造法及びオルソヒドロキシマンデル酸ナトリウムの分離のための使用 | |
JP7128629B2 (ja) | ルビプロストンの製造方法 | |
JPS5931509B2 (ja) | 3−ヒドロキシ−3−メチルフタリド又はその核置換体の製造法 | |
JP2005538080A (ja) | 2−デオキシ−l−リボースの合成方法 | |
JP2005053836A (ja) | アセトアミジン誘導体の製造方法 | |
JP2853244B2 (ja) | ビス[3,5―ジブロモ―4―(ジブロモプロポキシ)フェニル]スルホンの製法 | |
JP5179532B2 (ja) | アセトアミジン誘導体の製造方法 | |
CN118239857A (zh) | 一种碘克沙醇杂质i的制备方法 | |
JP4402500B2 (ja) | イオパミドールの精製方法 | |
KR20010070672A (ko) | 결정성 3-0-알킬아스코르빈산의 제조방법 | |
WO2018127236A1 (zh) | 一种(2s,3r,4s)-2,3,4,5-四羟基-戊醛的制备方法 | |
JP4886938B2 (ja) | イミダゾリジノン誘導体の製法 | |
JP4917721B2 (ja) | イミダゾリジノン誘導体の製造方法 | |
EP3438090A1 (en) | Novel method for producing hydroxamic acid derivative, and intermediate thereof | |
JP2021095378A (ja) | ケトン誘導体の製造方法 | |
JP2010168295A (ja) | 1‐(ペンタフルオロスルファニルベンゼン)‐2‐フェニルエタン‐1,2−ジオン化合物の製造方法 | |
CN111732526A (zh) | 一种二苯砜衍生物的组合物及其制法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20120522 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20120531 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5009992 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20150608 Year of fee payment: 3 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |