IN2014MN01086A - - Google Patents
Info
- Publication number
- IN2014MN01086A IN2014MN01086A IN1086MUN2014A IN2014MN01086A IN 2014MN01086 A IN2014MN01086 A IN 2014MN01086A IN 1086MUN2014 A IN1086MUN2014 A IN 1086MUN2014A IN 2014MN01086 A IN2014MN01086 A IN 2014MN01086A
- Authority
- IN
- India
- Prior art keywords
- carbon atoms
- ceramide
- produced
- optically active
- optionally
- Prior art date
Links
- 125000004432 carbon atom Chemical group C* 0.000 abstract 6
- YDNKGFDKKRUKPY-JHOUSYSJSA-N C16 ceramide Natural products CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C=CCCCCCCCCCCCCC YDNKGFDKKRUKPY-JHOUSYSJSA-N 0.000 abstract 5
- CRJGESKKUOMBCT-VQTJNVASSA-N N-acetylsphinganine Chemical compound CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(C)=O CRJGESKKUOMBCT-VQTJNVASSA-N 0.000 abstract 5
- 229940106189 ceramide Drugs 0.000 abstract 5
- ZVEQCJWYRWKARO-UHFFFAOYSA-N ceramide Natural products CCCCCCCCCCCCCCC(O)C(=O)NC(CO)C(O)C=CCCC=C(C)CCCCCCCCC ZVEQCJWYRWKARO-UHFFFAOYSA-N 0.000 abstract 5
- VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 abstract 5
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 230000009435 amidation Effects 0.000 abstract 1
- 238000007112 amidation reaction Methods 0.000 abstract 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 abstract 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000013078 crystal Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/08—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cephalosporin Compounds (AREA)
Abstract
Provided is a method for producing an optically active ceramide by an N acylation (amidation) reaction of an optically active aminodiol wherein a crude ceramide produced therein is purified by an industrially advantageous process. Namely provided is a method for producing a high purity ceramide that has high diastereo purity with high yield. A high purity ceramide is produced by: a step wherein a ceramide represented by general formula (1) is produced by reacting an aminodiol with an alkyl ester having 1 5 carbon atoms of an aliphatic carboxylic acid having 12 24 carbon atoms said aliphatic carboxylic acid optionally having a hydroxyl group in a hydrocarbon solvent having 5 10 carbon atoms; and a step wherein an alcohol having 1 3 carbon atoms is added into the reaction mixture obtained in the preceding step thereby causing crystals to precipitate. (In the formula R represents an alkyl group which has 13 17 carbon atoms and optionally has a carbon carbon unsaturated bond; R represents an alkyl group which has 11 23 carbon atoms and optionally has a hydroxyl group; and * represents an optically active state.)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2011281654A JP5825672B2 (en) | 2011-12-22 | 2011-12-22 | Method for producing high purity ceramides |
| PCT/JP2012/007122 WO2013094108A1 (en) | 2011-12-22 | 2012-11-07 | Method for producing high-purity ceramide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IN2014MN01086A true IN2014MN01086A (en) | 2015-07-03 |
Family
ID=48668028
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IN1086MUN2014 IN2014MN01086A (en) | 2011-12-22 | 2012-11-07 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US9079826B2 (en) |
| EP (1) | EP2796444B1 (en) |
| JP (1) | JP5825672B2 (en) |
| CN (1) | CN103974930B (en) |
| IN (1) | IN2014MN01086A (en) |
| WO (1) | WO2013094108A1 (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6232008B2 (en) | 2015-03-19 | 2017-11-15 | 国立大学法人北海道大学 | Oxidation inhibitor and oil-containing food and drink using the same |
| CN112759535B (en) * | 2019-11-01 | 2024-04-05 | 广东东阳光药业股份有限公司 | Preparation method of PF-06651600 intermediate |
| EP4482820A1 (en) | 2022-02-21 | 2025-01-01 | Cataya Bio (Shanghai) Co., Ltd. | Sphingolipid production |
| CN120957967A (en) * | 2023-03-16 | 2025-11-14 | 柯泰亚生物科技(上海)有限公司 | Ceramide production |
| CN121219259A (en) | 2023-05-29 | 2025-12-26 | 柯泰亚生物科技(上海)有限公司 | lipid blends |
| CN117567311A (en) * | 2023-11-28 | 2024-02-20 | 重庆智合生物医药有限公司 | Method for efficiently preparing alpha-hydroxy fatty acid ceramide |
| CN117567310A (en) * | 2023-11-28 | 2024-02-20 | 重庆智合生物医药有限公司 | Synthesis method of ceramide NP1 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0692349B2 (en) * | 1986-03-06 | 1994-11-16 | 和光純薬工業株式会社 | A new method for producing optically active unsaturated amino alcohol derivatives. |
| WO1995025716A1 (en) | 1994-03-18 | 1995-09-28 | Gist-Brocades B.V. | Linoleoylamide based ceramide derivative and its use in cosmetic preparations for the treatment of dry skin |
| EP0688871A3 (en) | 1994-06-24 | 1998-07-08 | Quest International B.V. | Preparation of phytosphingosine derivative |
| FR2732680B1 (en) | 1995-04-05 | 1997-05-09 | Oreal | CERAMID-LIKE COMPOUNDS, PROCESS FOR THEIR PREPARATION AND THEIR USE |
| JP4101320B2 (en) * | 1996-10-11 | 2008-06-18 | 高砂香料工業株式会社 | Method for producing primary amide derivative |
| JP3148136B2 (en) | 1996-12-26 | 2001-03-19 | 高砂香料工業株式会社 | Novel chiral diphosphine compound, intermediate for producing the same, transition metal complex having the diphosphine compound as a ligand, and asymmetric hydrogenation catalyst containing the complex |
| JP3485232B2 (en) * | 1997-01-31 | 2004-01-13 | 高砂香料工業株式会社 | Optically active compound and method for producing the same |
| JP3549390B2 (en) | 1998-03-23 | 2004-08-04 | 高砂香料工業株式会社 | Ruthenium-phosphine complex and method for producing the same |
| WO2008041571A1 (en) * | 2006-09-26 | 2008-04-10 | Kaneka Corporation | Process for producing optically active beta-hydroxy-alpha-aminocarboxylic acid ester |
-
2011
- 2011-12-22 JP JP2011281654A patent/JP5825672B2/en active Active
-
2012
- 2012-11-07 IN IN1086MUN2014 patent/IN2014MN01086A/en unknown
- 2012-11-07 WO PCT/JP2012/007122 patent/WO2013094108A1/en not_active Ceased
- 2012-11-07 US US14/366,883 patent/US9079826B2/en active Active
- 2012-11-07 CN CN201280059943.0A patent/CN103974930B/en not_active Expired - Fee Related
- 2012-11-07 EP EP12859986.7A patent/EP2796444B1/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US20140364649A1 (en) | 2014-12-11 |
| CN103974930B (en) | 2016-09-28 |
| CN103974930A (en) | 2014-08-06 |
| EP2796444A1 (en) | 2014-10-29 |
| EP2796444A4 (en) | 2015-12-16 |
| JP2013129640A (en) | 2013-07-04 |
| US9079826B2 (en) | 2015-07-14 |
| EP2796444B1 (en) | 2017-03-15 |
| WO2013094108A1 (en) | 2013-06-27 |
| JP5825672B2 (en) | 2015-12-02 |
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