IE31869L - Glyceryl esters of acetylsalicylic acid - Google Patents
Glyceryl esters of acetylsalicylic acidInfo
- Publication number
- IE31869L IE31869L IE680420A IE42068A IE31869L IE 31869 L IE31869 L IE 31869L IE 680420 A IE680420 A IE 680420A IE 42068 A IE42068 A IE 42068A IE 31869 L IE31869 L IE 31869L
- Authority
- IE
- Ireland
- Prior art keywords
- formula
- group
- compound
- isopropylidenedioxypropyl
- dioxolan
- Prior art date
Links
- 125000005908 glyceryl ester group Chemical group 0.000 title abstract 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 title 1
- 229960001138 acetylsalicylic acid Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 4
- -1 cyclic acetals Chemical class 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 abstract 2
- RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 abstract 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 2
- 229920002554 vinyl polymer Polymers 0.000 abstract 2
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 abstract 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 abstract 1
- 239000004593 Epoxy Substances 0.000 abstract 1
- 206010061218 Inflammation Diseases 0.000 abstract 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- ZTYZNOGSMXKEKP-UHFFFAOYSA-N cyanomethyl 2-hydroxybenzoate Chemical compound OC1=CC=CC=C1C(=O)OCC#N ZTYZNOGSMXKEKP-UHFFFAOYSA-N 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000004054 inflammatory process Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 229960001860 salicylate Drugs 0.000 abstract 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 abstract 1
- 229960004889 salicylic acid Drugs 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/24—Radicals substituted by singly bound oxygen or sulfur atoms esterified
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Epoxy Compounds (AREA)
Abstract
1,226,813. Glyceryl ester derivatives. SCHERICO Ltd. 5 April, 1968 [10 April, 1967], No. 16479/68. Heading C2C. Novel compounds of general Formula I in which R<SP>a</SP> and R<SP>b</SP> are hydrogen atoms or alkyl radicals, the total number of carbon atoms in R<SP>a</SP> and R<SP>b</SP> being not more than 3, and n is 0 or 1 and their pharmaceutically acceptable cyclic acetals and ketals, preferably of Formula II in which R<SP>1</SP> and R<SP>2</SP> are H, alkyl, aryl or aralkyl or together form a polymethylene group are prepared by condensing a compound of formula Y.CH 2 .X<SP>1</SP> by known methods with a compound of formula Z.CO.CR<SP>a</SP>R<SP>b</SP>.A in which X<SP>1</SP> is an α,#-dihydroxy-ethyl or a cyclic acetal or ketal thereof or a vinyl or epoxy ethyl group and either Y and Z represent groups capable of condensing during esterification one of Y and Z providing the grouping III and A is H or Y represents the group IV and Z and A together represent a further C-C bond and where X<SP>1</SP> is a vinyl or epoxyethyl group converting the product by known methods of oxidation or hydrolysis to the ester I. Intermediates isolated are cyanomethyl salicylate (from reaction of chloroacetonitrile with salicylic acid); #,γ - isopropylidenedioxypropyl salicylate (from reaction of cyano derivative with 2,2 - dimethyl - 4 - hydroxymethyl - 1,3- dioxolan); and 0 - (#,γ - isopropylidenedioxypropyl) - N<SP>1</SP>,N - dicyclohexyl - isourea (by reacting dicyclohexylcarbodiimide with 2,2-dimethyl- 4-hydroxymethyl-1,3-dioxolan). Pharmaceutical compositions used in relief of inflammation and pain comprise a compound I in association with a suitable excipient and may be administered enterally, parenterally or topically.
[GB1226813A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62941467A | 1967-04-10 | 1967-04-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE31869L true IE31869L (en) | 1968-10-10 |
| IE31869B1 IE31869B1 (en) | 1973-01-24 |
Family
ID=24522896
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE420/68A IE31869B1 (en) | 1967-04-10 | 1968-04-09 | Glyceryl ester compounds |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE713501A (en) |
| DE (1) | DE1768169A1 (en) |
| ES (1) | ES352580A1 (en) |
| FR (1) | FR8057M (en) |
| GB (1) | GB1226813A (en) |
| IE (1) | IE31869B1 (en) |
| IL (1) | IL29777A (en) |
| NL (1) | NL6805080A (en) |
-
1968
- 1968-04-05 GB GB1226813D patent/GB1226813A/en not_active Expired
- 1968-04-08 IL IL29777A patent/IL29777A/en unknown
- 1968-04-09 IE IE420/68A patent/IE31869B1/en unknown
- 1968-04-09 ES ES352580A patent/ES352580A1/en not_active Expired
- 1968-04-09 DE DE19681768169 patent/DE1768169A1/en active Pending
- 1968-04-10 NL NL6805080A patent/NL6805080A/xx unknown
- 1968-04-10 BE BE713501D patent/BE713501A/xx unknown
- 1968-04-10 FR FR147683A patent/FR8057M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1768169A1 (en) | 1971-11-04 |
| FR8057M (en) | 1970-07-06 |
| IL29777A0 (en) | 1968-06-20 |
| IL29777A (en) | 1972-04-27 |
| GB1226813A (en) | 1971-03-31 |
| ES352580A1 (en) | 1969-07-01 |
| NL6805080A (en) | 1968-10-11 |
| BE713501A (en) | 1968-10-10 |
| IE31869B1 (en) | 1973-01-24 |
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