[go: up one dir, main page]

GB1227978A - - Google Patents

Info

Publication number
GB1227978A
GB1227978A GB1227978DA GB1227978A GB 1227978 A GB1227978 A GB 1227978A GB 1227978D A GB1227978D A GB 1227978DA GB 1227978 A GB1227978 A GB 1227978A
Authority
GB
United Kingdom
Prior art keywords
group
methyl
general formula
reaction
phenoxycarbonyl
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
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 filed Critical
Publication of GB1227978A publication Critical patent/GB1227978A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
    • 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
    • A61K31/415—1,2-Diazoles
    • 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
    • A61K31/425—Thiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
    • C07C259/18—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (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

1,227,978. 1,2,4-Oxa- or thiadiazole derivatives. IMPERIAL CHEMICAL INDUSTRIES Ltd. 12 Aug., 1969 [13 Sept., 1968], No. 43628/68. Heading C2C. [Also in Division A5] 1,2,4-Oxa- or thiadiazole derivatives of the general formula wherein Y is a phenyl, monohalogenophenyl or dihalogenophenyl group in which the halogeno substituent(s) is/are fluorine, chlorine or bromine atoms and either (i) R<SP>1</SP> is a methyl group, R<SP>2</SP> is a hydrogen atom or a methyl, C 2-6 alkoxycarbonyl, benzyloxycarbonyl or phenoxycarbonyl group and R<SP>3</SP> is a carboxy, C 2-6 alkoxycarbonyl, benzyloxycarbonyl or phenoxycarbonyl group and, when R<SP>2</SP> is a C 2-6 alkoxycarbonyl, benzyloxycarbonyl or phenoxycarbonyl group, R<SP>3</SP> is the same group; or (ii) R<SP>1</SP> and R<SP>2</SP> are both a hydrogen atom and R<SP>3</SP> is a carboxymethyl, C 3-7 alkoxycarbonylmethyl, benzyloxycarbonylmethyl or phenoxycarbonyl - methyl group, and A is an oxygen or sulphur atom, and non-toxic, pharmaceutically acceptable salts thereof, which are novel with the exception of #-(3-phenyl-1,2,4-oxadiazol-5-yl) propionic acid and the ethyl ester thereof, are prepared (a) when R<SP>3</SP> is a COOR<SP>4</SP> group in which R<SP>4</SP> is a C 1-5 alkyl, benzyl or phenyl group and R<SP>1</SP> and R<SP>2</SP> are as defined under (i) above, by reaction of an alkali metal derivative of a compound of the general formula with methyl chloride, bromide or iodide; (b) when the CR<SP>1</SP>R<SP>2</SP>R<SP>2</SP> group is in the 5-position, R<SP>3</SP> is a COOR<SP>4</SP> group and R<SP>2</SP> is R<SP>5</SP> which is a hydrogen atom or a methyl group, by reaction of a compound of the general formula with sodium or potassium or a hydride, amide or C 1-4 alkoxide thereof and a carbonate of the general formula CO(OR<SP>4</SP>) 2 ; (c) when R<SP>3</SP> is a COOH group and R 2 is R 5 , -CR<SP>1</SP>R<SP>5</SP> possibly being by hydrolysis of a compound of the general formula wherein R<SP>6</SP> is a cyano, carbamoyl, C 2-6 alkoxycarbonyl, phenoxycarbonyl or benzyloxycarbonyl group; (d) when the CR<SP>1</SP>R<SP>2</SP>R<SP>3</SP> group is in the 5-position and is a -CH 2 CH 2 COOH group, by dehydration of a compound of the general formula (e) when R<SP>1</SP> is a methyl group and R<SP>3</SP> is a C 2-6 alkoxycarbonyl, benzyloxycarbonyl or phenoxycarbonyl group or R<SP>1</SP> and R<SP>2</SP> are both a hydrogen atom and R<SP>3</SP> is a C 3-7 alkoxy carbonylmethyl, benzyloxycarbonylmethyl or phenoxycarbonylmethyl group, by esterification of the corresponding carboxylic acid or a salt thereof; and (f) when R<SP>2</SP> is a hydrogen atom, R<SP>3</SP> is a COOH group and either R<SP>1</SP> is a methyl group or -CR<SP>1</SP>R<SP>2</SP> is a -CH 2 CH 2 - group, by reaction of a compound of the general formula wherein R<SP>1</SP> is a methyl group or -CR<SP>1</SP> = is a -CH 2 CH = group, with a strong inorganic base in the presence of water and under the influence of heat; followed optionally, where appropriate, by salification of the product. Methyl 3 - p - chlorophenyl - 1,2,4 - oxadiazol- 5-ylacetate is prepared by reaction of p-chlorobenzamidoxime with dimethyl malonate. Methyl 5 - p - chlorophenyl - 1,2,4 - oxadiazol- 3-ylacetate is prepared by reaction of a-carbamoylacetamidoxime with p-chlorobenzoyl chloride in the presence of aqueous sodium hydroxide, dehydration of the resulting α-carbamoyl - O p - chlorobenzoylacetamidozime and reaction of the resulting 5-p-chlorophenyl-1,2,4- oxadiazol-3-ylacetamide with hydrogen chloride in methanol.
GB1227978D 1968-09-13 1968-09-13 Expired GB1227978A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB4362868 1968-09-13

Publications (1)

Publication Number Publication Date
GB1227978A true GB1227978A (en) 1971-04-15

Family

ID=10429626

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1227978D Expired GB1227978A (en) 1968-09-13 1968-09-13

Country Status (5)

Country Link
BE (1) BE738831A (en)
DE (1) DE1946638A1 (en)
FR (1) FR2018062B1 (en)
GB (1) GB1227978A (en)
NL (1) NL6913673A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4618617A (en) * 1982-03-03 1986-10-21 Sumitomo Chemical Company, Limited Novel 5-substituted 1,2,4,-oxadiazole derivatives and preparation thereof
JP7637121B2 (en) 2020-03-17 2025-02-27 住友ファーマ株式会社 Oxadiazole Derivatives

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4562186A (en) * 1985-01-22 1985-12-31 Hoechst-Roussel Pharmaceuticals Inc. (1,2,4-Oxadiazol-3-yl)arylmethanones, compositions and pharmaceutical use
JP2002508323A (en) * 1997-12-17 2002-03-19 メルク エンド カムパニー インコーポレーテッド Integrin receptor antagonist

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4618617A (en) * 1982-03-03 1986-10-21 Sumitomo Chemical Company, Limited Novel 5-substituted 1,2,4,-oxadiazole derivatives and preparation thereof
JP7637121B2 (en) 2020-03-17 2025-02-27 住友ファーマ株式会社 Oxadiazole Derivatives

Also Published As

Publication number Publication date
DE1946638A1 (en) 1970-09-03
FR2018062B1 (en) 1974-01-11
NL6913673A (en) 1970-03-17
BE738831A (en) 1970-03-12
FR2018062A1 (en) 1970-05-29

Similar Documents

Publication Publication Date Title
GB1140748A (en) New carboxylic acid derivatives
ES467890A1 (en) Process for the preparation of acetic acid derivatives
GB1250719A (en)
GB1227978A (en)
SU447888A1 (en) The method of obtaining benzo-1,2,4-triazindi- -oxide- (1,4)
GB1382513A (en) 1-pyridylalkyl-indole derivatives
GB1334705A (en) Pharmaceutical compositions containing kynurenic acid derivatives
US3669987A (en) Salts of indole derivatives and a process for preparing the same
GB1432649A (en)
IE44014L (en) Amino-benzocycloheptenes.
GB1497681A (en) Thiomethyl ergolene derivatives
GB1251696A (en)
ES422472A1 (en) 2-(phenoxyalkylthio)imidazoles and congeners
GB1365173A (en) Cyclopentane derivatives
IE792508L (en) Piperidylindoles
GB1139940A (en) Oxazole derivatives
KR890009879A (en) Method for preparing 5-amino-1-phenyl-4-nitropyrazole
GB1118867A (en) Phenoxazine derivatives
ES426951A1 (en) Carboxylic acid esters of 3-biphenylyl-(butanols)
GB1226981A (en)
GB1088295A (en) Derivatives of alkanoic acids and methods for their preparation
GB1220599A (en) New furazan derivatives, processes for their production and compositions containing them
GB1099209A (en) 5-sulfamoylanthranilic acid derivatives
ES442068A1 (en) 3-(2-Halo-4-biphenylyl)-1-butanols and derivatives thereof
SE7705257L (en) KIT FOR PREPARATION OF ACETONITRILE DERIVATIVES

Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees