GB1427097A - Optically-active morpholine derivatives - Google Patents

Optically-active morpholine derivatives

Info

Publication number
GB1427097A
GB1427097A GB4849073A GB4849073A GB1427097A GB 1427097 A GB1427097 A GB 1427097A GB 4849073 A GB4849073 A GB 4849073A GB 4849073 A GB4849073 A GB 4849073A GB 1427097 A GB1427097 A GB 1427097A
Authority
GB
United Kingdom
Prior art keywords
formula
optically
radical
stands
active
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
GB4849073A
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries 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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB4849073A priority Critical patent/GB1427097A/en
Priority to DE19742446046 priority patent/DE2446046A1/en
Priority to FR7434682A priority patent/FR2248049B2/fr
Priority to JP12022374A priority patent/JPS5064279A/ja
Publication of GB1427097A publication Critical patent/GB1427097A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings

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

1427097 Optically active morpholine derivatives IMPERIAL CHEMICAL INDUSTRIES Ltd 22 Aug 1974 [18 Oct 1973] 48490/73 Addition to 1138405 Heading C2C The invention comprises optically-active morpholine derivatives of the general Formula I wherein R<SP>1</SP> stands for hydrogen or a methyl, isopropyl or allyl radical, wherein R<SP>2</SP>, R<SP>3</SP> and R<SP>4</SP> which may be the same or different, stand for hydrogen or a methyl radical, and wherein X stands for a phenyl radical which may be unsubstituted or substituted by one substituent selected from methyl, n-propyl, allyl, propenyl, methoxy, ethoxy, n-propoxy, isopropoxy, nheptyloxy, alkyloxy, phenoxy, phenyl, methylthio and acetyl radicals and a chlorine atom or substituted by two methyl radicals; and the acid addition salts thereof, the optically-active derivative being that enantiomer having the (S) absolute configuration, as hereinafter defined, about the carbon atom of the morpholine ring bearing the side-chain. By a morpholine derivative having the (S) absolute configuration is meant one which, as a solution of its hydrochloride salt in methanol, exhibits a plain negative optical rotatory dispension curve between 16,000 and 43,000 cm.<SP>-1</SP> (6250 and 2330 Š units). The compounds of Formula I may be prepared by (a) resolution of the corresponding racemic morpholine derivative by conventional means, (b) reducing of an opticallyactive compound of the formula with a complex metal halide, (c) for those compounds in which R<SP>1</SP> is hydrogen, removal of the removable α-aryl alkyl or alkyl radical from an optically-active compound of the formula wherein R<SP>5</SP> stands for a removable α-aryl alkyl radical of up to 11 carbon atoms or a removable alkyl radical of 1 to 6 carbon atoms. (d) cyclization of an optically-active compound of the formula wherein Y stands for a displaceable radical, with a base or (e) reacting an optically-active compound of formula wherein Z stands for a displaceable radical, with a phenol of the formula The compounds of Formula I are used as pharmaceuticals.
GB4849073A 1973-10-18 1973-10-18 Optically-active morpholine derivatives Expired GB1427097A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
GB4849073A GB1427097A (en) 1973-10-18 1973-10-18 Optically-active morpholine derivatives
DE19742446046 DE2446046A1 (en) 1973-10-18 1974-09-26 OPTICALLY ACTIVE MORPHOLINE DERIVATIVES
FR7434682A FR2248049B2 (en) 1973-10-18 1974-10-15
JP12022374A JPS5064279A (en) 1973-10-18 1974-10-18

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4849073A GB1427097A (en) 1973-10-18 1973-10-18 Optically-active morpholine derivatives

Publications (1)

Publication Number Publication Date
GB1427097A true GB1427097A (en) 1976-03-03

Family

ID=10448816

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4849073A Expired GB1427097A (en) 1973-10-18 1973-10-18 Optically-active morpholine derivatives

Country Status (4)

Country Link
JP (1) JPS5064279A (en)
DE (1) DE2446046A1 (en)
FR (1) FR2248049B2 (en)
GB (1) GB1427097A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4410734A (en) 1980-01-16 1983-10-18 Basf Aktiengesellschaft Optically active phenylpropane derivatives, their preparation and their use for the preparation of fungicides

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL56369A (en) * 1978-01-20 1984-05-31 Erba Farmitalia Alpha-phenoxybenzyl propanolamine derivatives,their preparation and pharmaceutical compositions comprising them
US4931557A (en) * 1988-10-17 1990-06-05 Eli Lilly And Company Method of resolving cis 3-amino-4-(2-furyl)vinyl)-1-methoxycarbonylmethyl-azetidin-2-one and di-p-toluoyl-tartaric acid salts thereof
WO1993015052A1 (en) * 1992-01-28 1993-08-05 Smithkline Beecham Plc Compounds as calcium channel antagonists
WO1998007710A1 (en) * 1996-08-23 1998-02-26 Neurosearch A/S Disubstituted morpholine, oxazepine or thiazepine derivatives, their preparation and their use as dopamine d4 receptor antagonists
CA2422055A1 (en) 2000-09-11 2002-03-21 Sepracor, Inc. Ligands for monoamine receptors and transporters, and methods of use thereof (neurotransmission)
US7294637B2 (en) 2000-09-11 2007-11-13 Sepracor, Inc. Method of treating addiction or dependence using a ligand for a monamine receptor or transporter

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3712890A (en) * 1969-06-20 1973-01-23 Ici Ltd Process for making 2-aryloxymethyl morpholines
US4022957A (en) * 1973-05-23 1977-05-10 Standard Oil Company Thermoplastic nitrile resins

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4410734A (en) 1980-01-16 1983-10-18 Basf Aktiengesellschaft Optically active phenylpropane derivatives, their preparation and their use for the preparation of fungicides

Also Published As

Publication number Publication date
FR2248049B2 (en) 1978-07-21
DE2446046A1 (en) 1975-04-24
JPS5064279A (en) 1975-05-31
FR2248049A2 (en) 1975-05-16

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Legal Events

Date Code Title Description
PS Patent sealed
PE20 Patent expired after termination of 20 years