JP2002514654A5 - - Google Patents
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- Publication number
- JP2002514654A5 JP2002514654A5 JP2000548346A JP2000548346A JP2002514654A5 JP 2002514654 A5 JP2002514654 A5 JP 2002514654A5 JP 2000548346 A JP2000548346 A JP 2000548346A JP 2000548346 A JP2000548346 A JP 2000548346A JP 2002514654 A5 JP2002514654 A5 JP 2002514654A5
- Authority
- JP
- Japan
- Prior art keywords
- organic solvent
- amino alcohol
- group
- optionally substituted
- acid
- 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 description 14
- 150000001414 amino alcohols Chemical class 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 230000006181 N-acylation Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- -1 organic acid halide Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 150000003410 sphingosines Chemical class 0.000 description 2
- WWUZIQQURGPMPG-UHFFFAOYSA-N (-)-D-erythro-Sphingosine Natural products CCCCCCCCCCCCCC=CC(O)C(N)CO WWUZIQQURGPMPG-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- AERBNCYCJBRYDG-UHFFFAOYSA-N D-ribo-phytosphingosine Natural products CCCCCCCCCCCCCCC(O)C(O)C(N)CO AERBNCYCJBRYDG-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- OTKJDMGTUTTYMP-UHFFFAOYSA-N dihydrosphingosine Natural products CCCCCCCCCCCCCCCC(O)C(N)CO OTKJDMGTUTTYMP-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical group 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000011065 in-situ storage 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
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- AERBNCYCJBRYDG-KSZLIROESA-N phytosphingosine Chemical compound CCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@@H](N)CO AERBNCYCJBRYDG-KSZLIROESA-N 0.000 description 1
- 229940033329 phytosphingosine Drugs 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- OTKJDMGTUTTYMP-ZWKOTPCHSA-N sphinganine Chemical group CCCCCCCCCCCCCCC[C@@H](O)[C@@H](N)CO OTKJDMGTUTTYMP-ZWKOTPCHSA-N 0.000 description 1
- WWUZIQQURGPMPG-KRWOKUGFSA-N sphingosine Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO WWUZIQQURGPMPG-KRWOKUGFSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98201647 | 1998-05-14 | ||
| EP98201647.9 | 1998-05-14 | ||
| PCT/EP1999/003250 WO1999058542A1 (en) | 1998-05-14 | 1999-05-07 | Process for the acylation of amino alcohols |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002514654A JP2002514654A (ja) | 2002-05-21 |
| JP2002514654A5 true JP2002514654A5 (https=) | 2006-01-05 |
| JP4255621B2 JP4255621B2 (ja) | 2009-04-15 |
Family
ID=8233735
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000548346A Expired - Fee Related JP4255621B2 (ja) | 1998-05-14 | 1999-05-07 | アミノアルコールのアシル化方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6420604B1 (https=) |
| EP (1) | EP0994888B1 (https=) |
| JP (1) | JP4255621B2 (https=) |
| KR (1) | KR100539197B1 (https=) |
| CN (1) | CN1200945C (https=) |
| BR (1) | BR9906444A (https=) |
| DE (1) | DE69914560T2 (https=) |
| ES (1) | ES2214856T3 (https=) |
| WO (1) | WO1999058542A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003217508A1 (en) * | 2003-03-07 | 2004-09-28 | Korea Atomic Energy Research Institute | A composition comprising phytosphingosine or a derivative thereof |
| DE102008002409A1 (de) | 2008-06-13 | 2009-12-17 | Evonik Goldschmidt Gmbh | Enzymatische Synthese von Sphingolipiden |
| DE102008002410A1 (de) | 2008-06-13 | 2009-12-17 | Evonik Goldschmidt Gmbh | Enzymatische Synthese von Sphingolipiden |
| HUE034436T2 (en) * | 2008-11-18 | 2018-02-28 | Bracco Imaging Spa | A method for producing iodinated contrast media |
| JP5575718B2 (ja) * | 2011-09-13 | 2014-08-20 | 花王株式会社 | Ｎ−アシルアミノトリオールの製造法 |
| DE102011085497A1 (de) | 2011-10-31 | 2013-05-02 | Evonik Industries Ag | Kosmetische Formulierung |
| US11000458B2 (en) | 2017-03-27 | 2021-05-11 | Evonik Operations Gmbh | Method and product for producing formulations containing ceramide |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4036843A (en) * | 1975-11-14 | 1977-07-19 | Interx Research Corporation | Certain chloroamino esters of pyridine carboxylates and derivatives thereof |
| EP0212400B1 (de) | 1985-08-13 | 1992-01-02 | Solco Basel AG | Neues Verfahren zur Herstellung von Sphingosinderivaten |
| EP0633875B1 (en) * | 1992-04-03 | 1997-01-02 | Gist-Brocades N.V. | Selective n-acylation of amino alcohols |
| JP3782102B2 (ja) * | 1993-10-28 | 2006-06-07 | コスモフェルム ベースローテン フェンノートシャップ | フィトスフィンゴシンを基体としたセラミドｉアナログ |
| RU2071465C1 (ru) * | 1994-03-16 | 1997-01-10 | Волгоградское акционерное общество открытого типа "Химпром" | Способ получения водного раствора производных n-ацил-n-гидроксиалкилглицината натрия |
| DE69507006T2 (de) * | 1994-09-30 | 1999-06-02 | Gist-Brocades B.V., Delft | Ceramid-3-derivate von einfachungesättigten fettsäuren |
-
1999
- 1999-05-07 US US09/462,348 patent/US6420604B1/en not_active Expired - Lifetime
- 1999-05-07 BR BR9906444-8A patent/BR9906444A/pt not_active IP Right Cessation
- 1999-05-07 EP EP99924945A patent/EP0994888B1/en not_active Expired - Lifetime
- 1999-05-07 KR KR10-2000-7000384A patent/KR100539197B1/ko not_active Expired - Lifetime
- 1999-05-07 CN CNB99800748XA patent/CN1200945C/zh not_active Expired - Fee Related
- 1999-05-07 ES ES99924945T patent/ES2214856T3/es not_active Expired - Lifetime
- 1999-05-07 WO PCT/EP1999/003250 patent/WO1999058542A1/en not_active Ceased
- 1999-05-07 DE DE69914560T patent/DE69914560T2/de not_active Expired - Lifetime
- 1999-05-07 JP JP2000548346A patent/JP4255621B2/ja not_active Expired - Fee Related
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