GB849541A - Preparation of unsaturated cyclic urea derivatives - Google Patents
Preparation of unsaturated cyclic urea derivativesInfo
- Publication number
- GB849541A GB849541A GB5621/57A GB562157A GB849541A GB 849541 A GB849541 A GB 849541A GB 5621/57 A GB5621/57 A GB 5621/57A GB 562157 A GB562157 A GB 562157A GB 849541 A GB849541 A GB 849541A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- polymer
- urea
- aldehyde
- acetaldehyde
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
Abstract
Cyclic ureas of the formula: <FORM:0849541/IV(b)/1> are prepared by reacting ethylene-urea or trimethylene-urea with an aldehyde RR1CH, CHO, R being H, phenyl, tolyl, benzyl, cyclohexyl or C1-C8 alkyl, R1 being H or C1-C4 alkyl, and n being 1 or 2. The reaction may be carried out with or without a solvent such as water or a C1-C4 alcohol. It is preferable to work at a temperature of 15 DEG -220 DEG C. and to add an acid to bring the pH to 1-6,5. The first stage of the reaction probably produces an N-(a -hydroxy-alkyl) compound which self-condenses to give a polymer. On heating to 185 DEG -300 DEG C. the polymer decomposes and the N-vinyl compound distils over; this stage is aided by the addition of alkali to bring the pH to 7-8. When a C1-C4 alcohol (e.g. methanol or isopropanol) is used as solvent the aldehyde initially forms a hemiacetal which reacts with the cyclic urea to give the N-(a -alkoxyalkyl) and N: N1-bis-(a -alkoxy-alkyl) compounds as well as the polymer. The alkoxy compounds can be distilled off separately before pyrolysis of the polymer, but if an alkali alkoxide is added they too yield the desired vinyl compound on heating and then need not be separated. In examples, the aldehydes used are acetaldehyde, propionalde hyde, capric aldehyde, phenylacetaldehyde, cyclohexyl-acetaldehyde and hydrocinnamaldehyde.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US849541XA | 1956-02-23 | 1956-02-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB849541A true GB849541A (en) | 1960-09-28 |
Family
ID=22188248
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5621/57A Expired GB849541A (en) | 1956-02-23 | 1957-02-19 | Preparation of unsaturated cyclic urea derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB849541A (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2445343A1 (en) * | 2009-06-25 | 2012-05-02 | Alkermes, Inc. | Prodrugs of nh-acidic compounds |
| US8796276B2 (en) | 2009-06-25 | 2014-08-05 | Alkermes Pharma Ireland Limited | Heterocyclic compounds for the treatment of neurological and psychological disorders |
| US8969337B2 (en) | 2011-12-15 | 2015-03-03 | Alkermes Pharma Ireland Limited | Prodrugs of secondary amine compounds |
| US9034867B2 (en) | 2011-03-18 | 2015-05-19 | Alkermes Pharma Ireland Limited | Pharmaceutical compositions comprising sorbitan esters |
| US9193685B2 (en) | 2012-09-19 | 2015-11-24 | Alkermes Pharma Ireland Limited | Pharmaceutical compositions having improved storage stability |
| US9452131B2 (en) | 2014-03-20 | 2016-09-27 | Alkermes Pharma Ireland Limited | Aripiprazole formulations having increased injection speeds |
| US9999670B2 (en) | 2012-03-19 | 2018-06-19 | Alkermes Pharma Ireland Limited | Pharmaceutical compositions comprising benzyl alcohol |
| WO2019101444A1 (en) * | 2017-11-24 | 2019-05-31 | Henkel Ag & Co. Kgaa | Hydrolytically labile heterocycles of odoriferous ketones or odoriferous aldehydes |
| US11273158B2 (en) | 2018-03-05 | 2022-03-15 | Alkermes Pharma Ireland Limited | Aripiprazole dosing strategy |
-
1957
- 1957-02-19 GB GB5621/57A patent/GB849541A/en not_active Expired
Cited By (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10023537B2 (en) | 2009-06-25 | 2018-07-17 | Alkermes Pharma Ireland Limited | Heterocyclic compounds for the treatment of neurological and psychological disorders |
| JP2012531434A (en) * | 2009-06-25 | 2012-12-10 | アルカーメス，インコーポレイテッド | Prodrugs of NH acidic compounds |
| EP2445343A4 (en) * | 2009-06-25 | 2012-12-26 | Alkermes Inc | Prodrugs of nh-acidic compounds |
| US8686009B2 (en) | 2009-06-25 | 2014-04-01 | Alkermes Pharma Ireland Limited | Prodrugs of NH-acidic compounds |
| US8796276B2 (en) | 2009-06-25 | 2014-08-05 | Alkermes Pharma Ireland Limited | Heterocyclic compounds for the treatment of neurological and psychological disorders |
| US11518745B2 (en) | 2009-06-25 | 2022-12-06 | Alkermes Pharma Ireland Limited | Heterocyclic compounds for the treatment of neurological and psychological disorders |
| US10822306B2 (en) | 2009-06-25 | 2020-11-03 | Alkermes Pharma Ireland Limited | Heterocyclic compounds for the treatment of neurological and psychological disorders |
| US10723728B2 (en) | 2009-06-25 | 2020-07-28 | Alkermes Pharma Ireland Limited | Prodrugs of Nh-acidic compounds |
| US10428058B2 (en) | 2009-06-25 | 2019-10-01 | Alkermes Pharma Ireland Limited | Prodrugs of NH-acidic compounds |
| US10351529B2 (en) | 2009-06-25 | 2019-07-16 | Alkermes Pharma Ireland Limited | Heterocyclic compounds for the treatment of neurological and psychological disorders |
| EP2445343A1 (en) * | 2009-06-25 | 2012-05-02 | Alkermes, Inc. | Prodrugs of nh-acidic compounds |
| US10112903B2 (en) | 2009-06-25 | 2018-10-30 | Alkermes Pharma Ireland Limited | Heterocyclic compounds for the treatment of neurological and psychological disorders |
| US10226458B2 (en) | 2011-03-18 | 2019-03-12 | Alkermes Pharma Ireland Limited | Pharmaceutical compositions comprising sorbitan esters |
| US9034867B2 (en) | 2011-03-18 | 2015-05-19 | Alkermes Pharma Ireland Limited | Pharmaceutical compositions comprising sorbitan esters |
| US9351976B2 (en) | 2011-03-18 | 2016-05-31 | Alkermes Pharma Ireland Limited | Pharmaceutical compositions comprising sorbitan esters |
| US8969337B2 (en) | 2011-12-15 | 2015-03-03 | Alkermes Pharma Ireland Limited | Prodrugs of secondary amine compounds |
| US9999670B2 (en) | 2012-03-19 | 2018-06-19 | Alkermes Pharma Ireland Limited | Pharmaceutical compositions comprising benzyl alcohol |
| US9193685B2 (en) | 2012-09-19 | 2015-11-24 | Alkermes Pharma Ireland Limited | Pharmaceutical compositions having improved storage stability |
| US10639376B2 (en) | 2012-09-19 | 2020-05-05 | Alkermes Pharma Ireland Limited | Pharmaceutical compositions having improved storage stability |
| US10342877B2 (en) | 2012-09-19 | 2019-07-09 | Alkermes Pharma Ireland Limited | Pharmaceutical compositions having improved storage stability |
| US11097006B2 (en) | 2012-09-19 | 2021-08-24 | Alkermes Pharma Ireland Limited | Pharmaceutical compositions having improved storage stability |
| US9861699B2 (en) | 2012-09-19 | 2018-01-09 | Alkermes Pharma Ireland Limited | Pharmaceutical compositions having improved storage stability |
| US10813928B2 (en) | 2014-03-20 | 2020-10-27 | Alkermes Pharma Ireland Limited | Aripiprazole formulations having increased injection speeds |
| US10085980B2 (en) | 2014-03-20 | 2018-10-02 | Alkermes Pharma Ireland Limited | Aripiprazole formulations having increased injection speeds |
| US10238651B2 (en) | 2014-03-20 | 2019-03-26 | Alkermes Pharma Ireland Limited | Aripiprazole formulations having increased injection speeds |
| US9452131B2 (en) | 2014-03-20 | 2016-09-27 | Alkermes Pharma Ireland Limited | Aripiprazole formulations having increased injection speeds |
| US11406632B2 (en) | 2014-03-20 | 2022-08-09 | Alkermes Pharma Ireland Limited | Aripiprazole formulations having increased injection speeds |
| US9526726B2 (en) | 2014-03-20 | 2016-12-27 | Alkermes Pharma Ireland Limited | Aripiprazole formulations having increased injection speeds |
| US11931355B2 (en) | 2014-03-20 | 2024-03-19 | Alkermes Pharma Ireland Limited | Aripiprazole formulations having increased injection speeds |
| WO2019101444A1 (en) * | 2017-11-24 | 2019-05-31 | Henkel Ag & Co. Kgaa | Hydrolytically labile heterocycles of odoriferous ketones or odoriferous aldehydes |
| US11542457B2 (en) | 2017-11-24 | 2023-01-03 | Henkel Ag & Co. Kgaa | Hydrolytically labile heterocycles of odoriferous ketones or odoriferous aldehydes |
| US11273158B2 (en) | 2018-03-05 | 2022-03-15 | Alkermes Pharma Ireland Limited | Aripiprazole dosing strategy |
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