GB1160468A - Morpholine Derivative - Google Patents

Morpholine Derivative

Info

Publication number
GB1160468A
GB1160468A GB50681/67A GB5068167A GB1160468A GB 1160468 A GB1160468 A GB 1160468A GB 50681/67 A GB50681/67 A GB 50681/67A GB 5068167 A GB5068167 A GB 5068167A GB 1160468 A GB1160468 A GB 1160468A
Authority
GB
United Kingdom
Prior art keywords
dimethoxyphenyl
compound
formula
reacting
bromopropionyl
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
Application number
GB50681/67A
Inventor
David George Bamford
David Frederick Biggs
Glyn Evan Lee
Anthony Joseph Owen
Derek William Pulsford
William Robert Wragg
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
May and Baker Ltd
Original Assignee
May and Baker Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by May and Baker Ltd filed Critical May and Baker Ltd
Priority to GB50681/67A priority Critical patent/GB1160468A/en
Priority to NL6806086A priority patent/NL6806086A/xx
Priority to SE05961/68A priority patent/SE331475B/xx
Priority to BE714777D priority patent/BE714777A/xx
Priority to IL29954A priority patent/IL29954A0/en
Priority to FR1584266D priority patent/FR1584266A/fr
Priority to FR150877A priority patent/FR7613M/fr
Priority to ES353657A priority patent/ES353657A1/en
Priority to CH685168A priority patent/CH487920A/en
Priority to IE539/68A priority patent/IE31900B1/en
Priority to DE19681770355 priority patent/DE1770355A1/en
Priority to AT918068A priority patent/AT286307B/en
Publication of GB1160468A publication Critical patent/GB1160468A/en
Expired legal-status Critical Current

Links

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.
GB50681/67A 1967-05-08 1967-05-08 Morpholine Derivative Expired GB1160468A (en)

Priority Applications (12)

Application Number Priority Date Filing Date Title
GB50681/67A GB1160468A (en) 1967-05-08 1967-05-08 Morpholine Derivative
NL6806086A NL6806086A (en) 1967-05-08 1968-04-29
SE05961/68A SE331475B (en) 1967-05-08 1968-05-02
BE714777D BE714777A (en) 1967-05-08 1968-05-07
IL29954A IL29954A0 (en) 1967-05-08 1968-05-07 Process for the preparation of morpholine derivatives and pharmaceutical compositions containing them
FR1584266D FR1584266A (en) 1967-05-08 1968-05-07
FR150877A FR7613M (en) 1967-05-08 1968-05-07
ES353657A ES353657A1 (en) 1967-05-08 1968-05-08 Morpholine Derivative
CH685168A CH487920A (en) 1967-05-08 1968-05-08 Process for preparing a new derivative of morpholine
IE539/68A IE31900B1 (en) 1967-05-08 1968-05-08 Morpholine derivative
DE19681770355 DE1770355A1 (en) 1967-05-08 1968-05-08 New morpholine derivatives and processes for their preparation
AT918068A AT286307B (en) 1967-11-07 1968-05-08 PROCESS FOR THE PREPARATION OF THE NEW 2,6-DIMETHOXYPHENYL-2-MORPHOLINOPROPIONATE IN OPTICALLY ACTIVE FORM, AND ITS ACID-ADDITION SALTS

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 (1)

Publication Number Publication Date
GB1160468A true GB1160468A (en) 1969-08-06

Family

ID=26255224

Family Applications (1)

Application Number Title Priority Date Filing Date
GB50681/67A Expired GB1160468A (en) 1967-05-08 1967-05-08 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) FR1584266A (en)
GB (1) GB1160468A (en)
IE (1) IE31900B1 (en)
IL (1) IL29954A0 (en)
NL (1) NL6806086A (en)
SE (1) SE331475B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6451854B1 (en) 1998-07-22 2002-09-17 Akzo Nobel N.V. α-amino acid phenyl ester derivatives
DE10306761B3 (en) * 2003-02-17 2004-08-26 Völkl, Klaus Peter, Dr. Process for the production of sterile active pharmaceutical ingredients
US7141560B2 (en) 2001-01-19 2006-11-28 Akzo Nobel N.V. Alanine 2,6-dialkoxyphenyl ester derivatives as hypnotics

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6451854B1 (en) 1998-07-22 2002-09-17 Akzo Nobel N.V. α-amino acid phenyl ester derivatives
US7141560B2 (en) 2001-01-19 2006-11-28 Akzo Nobel N.V. Alanine 2,6-dialkoxyphenyl ester derivatives as hypnotics
DE10306761B3 (en) * 2003-02-17 2004-08-26 Völkl, Klaus Peter, Dr. Process for the production of sterile active pharmaceutical ingredients
DE10306761B9 (en) * 2003-02-17 2004-12-23 Völkl, Klaus Peter, Dr. Process for the production of sterile active pharmaceutical ingredients

Also Published As

Publication number Publication date
BE714777A (en) 1968-11-07
FR7613M (en) 1970-01-19
IL29954A0 (en) 1968-07-25
DE1770355A1 (en) 1972-03-16
IE31900L (en) 1968-11-08
IE31900B1 (en) 1973-02-07
SE331475B (en) 1971-01-04
CH487920A (en) 1970-03-31
NL6806086A (en) 1968-11-11
ES353657A1 (en) 1969-10-16
FR1584266A (en) 1969-12-19

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PLNP Patent lapsed through nonpayment of renewal fees