IE31900L - 2, 6-dimethoxyphenyl 2-morpholinopropionate - Google Patents
2, 6-dimethoxyphenyl 2-morpholinopropionateInfo
- Publication number
- IE31900L IE31900L IE680539A IE53968A IE31900L IE 31900 L IE31900 L IE 31900L IE 680539 A IE680539 A IE 680539A IE 53968 A IE53968 A IE 53968A IE 31900 L IE31900 L IE 31900L
- Authority
- IE
- Ireland
- Prior art keywords
- dimethoxyphenyl
- compound
- formula
- reacting
- morpholinopropionate
- Prior art date
Links
- QCQWVVNWUYVAGV-UHFFFAOYSA-N (2,6-dimethoxyphenyl) 2-morpholin-4-ylpropanoate Chemical compound COC1=CC=CC(OC)=C1OC(=O)C(C)N1CCOCC1 QCQWVVNWUYVAGV-UHFFFAOYSA-N 0.000 title abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- 239000002253 acid Substances 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical compound COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 abstract 2
- OZGMODDEIHYPRY-UHFFFAOYSA-N 2-bromopropanoyl chloride Chemical compound CC(Br)C(Cl)=O OZGMODDEIHYPRY-UHFFFAOYSA-N 0.000 abstract 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 231100000252 nontoxic Toxicity 0.000 abstract 2
- 230000003000 nontoxic effect Effects 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- -1 (-) - 2,6 - Dimethoxyphenyl Chemical group 0.000 abstract 1
- YXMMSZOODALKHJ-UHFFFAOYSA-N (2,6-dimethoxyphenyl) 2-aminopropanoate Chemical compound NC(C(=O)OC1=C(C=CC=C1OC)OC)C YXMMSZOODALKHJ-UHFFFAOYSA-N 0.000 abstract 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 239000002671 adjuvant Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical group 0.000 abstract 1
- 230000003444 anaesthetic effect Effects 0.000 abstract 1
- 239000002270 dispersing agent Substances 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 230000001804 emulsifying effect Effects 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 238000010348 incorporation Methods 0.000 abstract 1
- 150000002780 morpholines Chemical class 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 abstract 1
- 239000003755 preservative agent Substances 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000003206 sterilizing agent Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 238000009736 wetting Methods 0.000 abstract 1
- 239000000080 wetting agent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,160,468. Morpholine derivative. MAY & BAKER Ltd. 6 May, 1968 [8 May, 1967: 7 Nov., 1967]. Nos. 21240/67 and 50681/67. Heading C2C. Novel 2,6-dimethoxyphenyl 2-morpholinopropionate in the form of the racemate or an optically active isomer, and non-toxic acid addition salts thereof is prepared by:- (a) reacting a compound of the Formula III: where X is the acid residue of a reactive ester with morpholine. or (b) reacting a compound of the Formula IV where Z is hydrogen or an alkali metal atom: with a compound of the Formula VII: where X 1 is a halogen atom; or (c) reacting 2,6-dimethoxyphenyl 2-aminopropionate with a compound of the formula X-(CH 2 ) 2 -O-(CH 2 ) 2 -X, where X is as defined above, in the presence of concentrated sulphuric acid. Enantiomorphic forms may be obtained by resolution of the racemate, or use of optically active starting materials. ( - )-α-Bromopropionyl chloride is obtained by treating the corresponding acid with thionyl chloride and phosphorus trichloride. (Œ) - 2,6 - Dimethoxyphenyl 2 - bromopropionate is obtained by adding (Œ)-α-bromopropionyl bromide in anhydrous benzene to a solution of 2,6-dimethoxyphenol and anhydrous pyridine in anhydrous benzene and then refluxing. (-) - 2,6 - Dimethoxyphenyl 2 - bromcpropionate is prepared similarly, but using ( - )- α-bromopropionyl chloride. Pharmaceutical compositions having local anaesthetic activity and containing 2,6-dimethoxyphenyl 2-morpholinopropionate and non- toxic acid addition salts thereof are administered parenterally in association with a pharmaceutical carrier. These compositions may also contain adjuvants such as preserving, wetting, emulsifying, dispersing and solubilizing agents. They may be sterilized, e.g. by filtration through a bacteria-retaining filter, by incorporation of sterilizing agents in the composition or by irradiation.
[GB1160468A]
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2124067 | 1967-05-08 | ||
| GB50681/67A GB1160468A (en) | 1967-05-08 | 1967-05-08 | Morpholine Derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE31900L true IE31900L (en) | 1968-11-08 |
| IE31900B1 IE31900B1 (en) | 1973-02-07 |
Family
ID=26255224
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE539/68A IE31900B1 (en) | 1967-05-08 | 1968-05-08 | Morpholine derivative |
Country Status (10)
| Country | Link |
|---|---|
| BE (1) | BE714777A (en) |
| CH (1) | CH487920A (en) |
| DE (1) | DE1770355A1 (en) |
| ES (1) | ES353657A1 (en) |
| FR (2) | FR7613M (en) |
| GB (1) | GB1160468A (en) |
| IE (1) | IE31900B1 (en) |
| IL (1) | IL29954A0 (en) |
| NL (1) | NL6806086A (en) |
| SE (1) | SE331475B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69909486T2 (en) | 1998-07-22 | 2004-05-27 | Akzo Nobel N.V. | PHENYLESTER DERIVATIVES OF ALPHA AMINO ACIDS |
| US7141560B2 (en) | 2001-01-19 | 2006-11-28 | Akzo Nobel N.V. | Alanine 2,6-dialkoxyphenyl ester derivatives as hypnotics |
| DE10306761B9 (en) * | 2003-02-17 | 2004-12-23 | Völkl, Klaus Peter, Dr. | Process for the production of sterile active pharmaceutical ingredients |
-
1967
- 1967-05-08 GB GB50681/67A patent/GB1160468A/en not_active Expired
-
1968
- 1968-04-29 NL NL6806086A patent/NL6806086A/xx unknown
- 1968-05-02 SE SE05961/68A patent/SE331475B/xx unknown
- 1968-05-07 FR FR150877A patent/FR7613M/fr not_active Expired
- 1968-05-07 IL IL29954A patent/IL29954A0/en unknown
- 1968-05-07 FR FR1584266D patent/FR1584266A/fr not_active Expired
- 1968-05-07 BE BE714777D patent/BE714777A/xx unknown
- 1968-05-08 CH CH685168A patent/CH487920A/en not_active IP Right Cessation
- 1968-05-08 DE DE19681770355 patent/DE1770355A1/en active Pending
- 1968-05-08 IE IE539/68A patent/IE31900B1/en unknown
- 1968-05-08 ES ES353657A patent/ES353657A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1584266A (en) | 1969-12-19 |
| FR7613M (en) | 1970-01-19 |
| NL6806086A (en) | 1968-11-11 |
| IL29954A0 (en) | 1968-07-25 |
| SE331475B (en) | 1971-01-04 |
| GB1160468A (en) | 1969-08-06 |
| CH487920A (en) | 1970-03-31 |
| ES353657A1 (en) | 1969-10-16 |
| DE1770355A1 (en) | 1972-03-16 |
| BE714777A (en) | 1968-11-07 |
| IE31900B1 (en) | 1973-02-07 |
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