GB1114116A – Isoxazole derivative and processes for its preparation
– Google Patents
GB1114116A – Isoxazole derivative and processes for its preparation
– Google Patents
Isoxazole derivative and processes for its preparation
Info
Publication number
GB1114116A
GB1114116A
GB2227265A
GB2227265A
GB1114116A
GB 1114116 A
GB1114116 A
GB 1114116A
GB 2227265 A
GB2227265 A
GB 2227265A
GB 2227265 A
GB2227265 A
GB 2227265A
GB 1114116 A
GB1114116 A
GB 1114116A
Authority
GB
United Kingdom
Prior art keywords
isoxazole
hydroxy
acid
benzyloxy
give
Prior art date
1964-07-22
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
GB2227265A
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.)
Novartis AG
Original Assignee
JR Geigy AG
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.)
1964-07-22
Filing date
1965-05-26
Publication date
1968-05-15
1965-03-23
Priority claimed from CH405365A
external-priority
patent/CH454146A/en
1965-04-15
Priority claimed from CH530965A
external-priority
patent/CH454147A/en
1965-05-26
Application filed by JR Geigy AG
filed
Critical
JR Geigy AG
1968-05-15
Publication of GB1114116A
publication
Critical
patent/GB1114116A/en
Status
Expired
legal-status
Critical
Current
Links
Espacenet
Global Dossier
Discuss
Classifications
A—HUMAN NECESSITIES
A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
A61K36/06—Fungi, e.g. yeasts
A61K36/07—Basidiomycota, e.g. Cryptococcus
A—HUMAN NECESSITIES
A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
A61K31/00—Medicinal preparations containing organic active ingredients
A61K31/33—Heterocyclic compounds
A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
A61K31/42—Oxazoles
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07D—HETEROCYCLIC COMPOUNDS
C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07D—HETEROCYCLIC COMPOUNDS
C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07D—HETEROCYCLIC COMPOUNDS
C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
C07D261/12—Oxygen atoms
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07D—HETEROCYCLIC COMPOUNDS
C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
Abstract
The novel 3-hydroxy-5-(a -amino-carboxymethyl)-isoxazole is prepared (1) by reacting a reactive ester of the corresponding a -hydroxy compound with ammonia and, if desired, liberating the acid from the ammonium salt obtained; (2) by hydrolysing a novel ester or imino ester or the corresponding nitrile of the acid; or (3) by isolation as a hydrate from the fungus Amanita muscaria. Salts with bases are prepared by standard procedures. The starting materials for (1) can be prepared by reacting 3 – (methoxy or benzyloxy) – 5 – formyl – isoxazole with HCN to give 3-(methoxy or benzyloxy)-5 – (a – hydroxy – cyanomethyl) – isoxazole, reacting this with HCl and a C1- 4 alkanol to give the corresponding imino-ester, hydrolysing this to a 3 – (methoxy or benzyloxy) – 5 – (a – hydroxy-alkoxycarbonylmethyl) – isoxazole, acylating this with a carboxylic or sulphonic acid halide, if desired converting this to a 3-(methoxy or benzyloxy) – 5 – (a – halo – alkoxycarbonylmethyl)-isoxazole by reaction with an alkali metal halide and hydrolysing either the a -acyloxy or the a -halo compound with HBr in acetic acid. The starting materials for (2) can be prepared by reacting a reactive ester of 5-hydroxymethyl-3-hydroxy-isoxazol with a salt of HCN to give 3 – hydroxy – 5 – cyanomethyl – isoxazole, brominating this to the a -bromo compound, and, if desired, converting this to an ester or imino ester of the corresponding acid. 3 – Benzyloxy – 5 – formyl – isoxazole is prepared by heating 2-(2-nitrovinyl)-furan with HBr in acetic acid to give 3-bromo-5-(b -carboxyethyl)-isoxazole, this is heated with chromium trioxide in sulphuric acid to give 3-bromo-5-carboxy-isoxazole, this with benzyl alcohol and KOH gives 3-benzyloxy-5-carboxy-isoxazole, and this gives the required product via the acid chloride and N,N-ethylene amide and reduction of the latter. 3 – Hydroxy – 5 – chloromethyl – isoxazole is prepared by converting methyl 4-chloroacetoacetate into ethyl 4-chloro-3,3-dimethoxy-butyrate, reacting this with hydroxylamine to give 4-chloro – 3,3 – dimethoxy – butyrohydroxamic acid and treating this with HCl in acetic acid. The compound of the invention, which is stated to have an inhibiting action on the central nervous system and to be suitable for the treatment of disturbed sleep and conditions of excitement, may be made up into pharmaceutical compositions for oral, rectal or parenteral administration.
GB2227265A
1964-07-22
1965-05-26
Isoxazole derivative and processes for its preparation
Expired
GB1114116A
(en)
Applications Claiming Priority (4)
Application Number
Priority Date
Filing Date
Title
CH956564
1964-07-22
CH405365A
CH454146A
(en)
1964-07-22
1965-03-23
Process for the preparation of the ammonium salt of the new α-amino-3-hydroxy-5-isoxazole acetic acid
CH525665
1965-04-14
CH530965A
CH454147A
(en)
1965-04-15
1965-04-15
Process for the production of a new isoxazole derivative
Publications (1)
Publication Number
Publication Date
GB1114116A
true
GB1114116A
(en)
1968-05-15
Family
ID=27428720
Family Applications (1)
Application Number
Title
Priority Date
Filing Date
GB2227265A
Expired
GB1114116A
(en)
1964-07-22
1965-05-26
Isoxazole derivative and processes for its preparation
Country Status (4)
Country
Link
BE
(1)
BE665249A
(en)
FR
(2)
FR1440257A
(en)
GB
(1)
GB1114116A
(en)
IL
(1)
IL23592A
(en)
1965
1965-05-24
IL
IL2359265A
patent/IL23592A/en
unknown
1965-05-26
GB
GB2227265A
patent/GB1114116A/en
not_active
Expired
1965-05-31
FR
FR18944A
patent/FR1440257A/en
not_active
Expired
1965-06-10
BE
BE665249D
patent/BE665249A/xx
unknown
1965-08-30
FR
FR29813A
patent/FR4592M/fr
not_active
Expired
Also Published As
Publication number
Publication date
FR1440257A
(en)
1966-05-27
BE665249A
(en)
1965-12-10
IL23592A
(en)
1969-01-29
FR4592M
(en)
1966-12-19
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