GB1356409A - Process for the preparation of 3-isoxazolyl carbonylureides - Google Patents

Process for the preparation of 3-isoxazolyl carbonylureides

Info

Publication number
GB1356409A
GB1356409A GB6011271A GB6011271A GB1356409A GB 1356409 A GB1356409 A GB 1356409A GB 6011271 A GB6011271 A GB 6011271A GB 6011271 A GB6011271 A GB 6011271A GB 1356409 A GB1356409 A GB 1356409A
Authority
GB
United Kingdom
Prior art keywords
alkyl
cycloalkyl
formula
isoxazolecarboxamides
compounds
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
GB6011271A
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.)
Shionogi and Co Ltd
Original Assignee
Shionogi and Co 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 Shionogi and Co Ltd filed Critical Shionogi and Co Ltd
Publication of GB1356409A publication Critical patent/GB1356409A/en
Expired legal-status Critical Current

Links

Classifications

    • 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

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)

Abstract

1356409 Isoxazole derivatives SHIONOGI & CO Ltd 23 Dec 1971 [28 Dec 1970] 60112/71 Heading C2C Isoxazole derivatives of the formula wherein R<SP>1</SP> is H, C 1-5 alkyl, C 1-5 alkoxy, or cycloalkyl, R<SP>2</SP> is H, C 1-5 alkyl or cycloalkyl; R<SP>3</SP> and R<SP>4</SP> each are H, C 1-5 alkyl, C 2-6 alkenyl, cycloalkyl phenyl or together with the N atom to which they are attached form a 1-pyrrolindyl, piperidino, 1-piperazinyl, 4-(C 1-5 alkyl)-1-piperazinyl or morpholino group are prepared by (a) reacting 5 - R<SP>1</SP> - 3 - isoxazolecarboxylic acids with carbodiimides of the formula wherein R<SP>3</SP> and R<SP>3</SP> are the same and each is C 1-5 alkyl or cycloalkyl, in inert solvents (R<SP>4</SP>= H), (b) treating 5-R<SP>1</SP>-3-isoxazolecarboxamides or N - (R<SP>2</SP> - substituted) - 5 - R<SP>1</SP> - 3 - isoxazolecarboxamides with compounds of the formula wherein Y is halogen, C 1-4 alkoxy, aryloxy, or acyloxy, or (c) treating 5-R<SP>1</SP>-3-isoxazolecarboxamides with oxalyl halides in inert solvents and reacting the thus obtained 5-R<SP>1</SP>-3-isocyantocarbonylisoxazoles with amines of the formula HNR<SP>3</SP>R<SP>4</SP>(R<SP>2</SP> = H). Pharmaceutical compositions, suitable for oral or parenteral administration, contain the above compounds when prepared by the above processes in admixture with pharmaceutically acceptable diluents or carriers. The compounds possess hypoglycemic activity. Reference has been directed by the Comptroller to Specification 1,305,216.
GB6011271A 1970-12-28 1971-12-23 Process for the preparation of 3-isoxazolyl carbonylureides Expired GB1356409A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP12543170 1970-12-28

Publications (1)

Publication Number Publication Date
GB1356409A true GB1356409A (en) 1974-06-12

Family

ID=14909910

Family Applications (1)

Application Number Title Priority Date Filing Date
GB6011271A Expired GB1356409A (en) 1970-12-28 1971-12-23 Process for the preparation of 3-isoxazolyl carbonylureides

Country Status (5)

Country Link
CA (1) CA935816A (en)
CS (1) CS179963B2 (en)
DE (1) DE2164843A1 (en)
FR (1) FR2120032B1 (en)
GB (1) GB1356409A (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4014876A (en) * 1969-11-12 1977-03-29 Shionogi & Co., Ltd. Isoxazole derivatives
US4163784A (en) 1978-03-09 1979-08-07 Pfizer Inc. Heterocyclylcarbonyl derivatives of urea, agents for dissolution of gallstones

Also Published As

Publication number Publication date
FR2120032B1 (en) 1975-03-14
FR2120032A1 (en) 1972-08-11
CS179963B2 (en) 1977-12-30
DE2164843A1 (en) 1972-07-20
CA935816A (en) 1973-10-23

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee