GB1427097A - Optically-active morpholine derivatives - Google Patents
Optically-active morpholine derivativesInfo
- 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
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.
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)
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)
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)
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 |
-
1973
- 1973-10-18 GB GB4849073A patent/GB1427097A/en not_active Expired
-
1974
- 1974-09-26 DE DE19742446046 patent/DE2446046A1/en not_active Ceased
- 1974-10-15 FR FR7434682A patent/FR2248049B2/fr not_active Expired
- 1974-10-18 JP JP12022374A patent/JPS5064279A/ja active Pending
Cited By (1)
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 |