GB1206403A - Oxazoles - Google Patents

Oxazoles

Info

Publication number
GB1206403A
GB1206403A GB5620366A GB5620366A GB1206403A GB 1206403 A GB1206403 A GB 1206403A GB 5620366 A GB5620366 A GB 5620366A GB 5620366 A GB5620366 A GB 5620366A GB 1206403 A GB1206403 A GB 1206403A
Authority
GB
United Kingdom
Prior art keywords
acid
radical
ester
reacting
group
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
GB5620366A
Inventor
Kevan Brown
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.)
John Wyeth and Brother Ltd
Original Assignee
John Wyeth and Brother 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 John Wyeth and Brother Ltd filed Critical John Wyeth and Brother Ltd
Priority to GB5620366A priority Critical patent/GB1206403A/en
Priority to IL2880367A priority patent/IL28803A/en
Priority to FI304067A priority patent/FI50416C/en
Priority to PL12355567A priority patent/PL72562B1/en
Priority to NL6715532.A priority patent/NL157012B/en
Priority to CH1716871A priority patent/CH545308A/en
Priority to CH1717071A priority patent/CH556351A/en
Priority to BE706625A priority patent/BE706625A/xx
Priority to CH1717171A priority patent/CH545310A/en
Priority to CH1717271A priority patent/CH536311A/en
Priority to CH1717371A priority patent/CH560205A5/xx
Priority to CH1716971A priority patent/CH545309A/en
Priority to LU54891D priority patent/LU54891A1/xx
Priority to CH1648872A priority patent/CH554884A/en
Priority to CH1485573A priority patent/CH560203A5/xx
Priority to CH1606467A priority patent/CH528531A/en
Priority to JP7368167A priority patent/JPS4938267B1/ja
Priority to DE19671795822 priority patent/DE1795822C2/en
Priority to FR128733A priority patent/FR8018M/fr
Priority to FR1584222D priority patent/FR1584222A/fr
Priority to DE19671670005 priority patent/DE1670005C2/en
Priority to SE1585567A priority patent/SE369307B/xx
Priority to ES347319A priority patent/ES347319A1/en
Priority to IT2286567A priority patent/IT1060876B/en
Priority to YU244367A priority patent/YU33830B/en
Publication of GB1206403A publication Critical patent/GB1206403A/en
Priority to MY7100197A priority patent/MY7100197A/en
Priority to YU249673A priority patent/YU33868B/en
Priority to SE7316107A priority patent/SE422209B/en
Priority to IN1519/CAL/74A priority patent/IN137972B/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
    • A61M25/00—Catheters; Hollow probes
    • A61M25/01—Introducing, guiding, advancing, emplacing or holding catheters
    • A61M25/02—Holding devices, e.g. on the body
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three 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
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
    • C07D277/24—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
    • C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Hematology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Biomedical Technology (AREA)
  • Anesthesiology (AREA)
  • Engineering & Computer Science (AREA)
  • Pulmonology (AREA)
  • Biophysics (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1,206,403. Oxazoles. JOHN WYETH & BROTHER Ltd. 14 Dec., 1967 [15 Dec., 1966], No. 56203/66. Heading C2C. Novel oxazoles of general Formula (I) and acid addition salts thereof in which R<SP>1</SP> is a saturated or unsaturated C 2-6 aliphatic acid radical attached to the oxazole ring by a carbon atom of the aliphatic chain or a salt, ester, amide or hydroxamic acid derivative thereof, at least one of R<SP>2</SP> and R<SP>3</SP> is a substituted or unsubstituted aryl or heteroaryl group and the other radical R<SP>2</SP> or R<SP>3</SP>, if not an aryl or heteroaryl group is a hydrogen atom or alkyl group with the proviso that, when R<SP>3</SP> is H and R<SP>2</SP> is phenyl optionally substituted by not more than 2 halogen atoms or by a CF 3 group then R<SP>1</SP> contains at least 2C in a straight chain between the oxazole ring and the carboxyl group or its derivative are prepared by: (a) reacting a keto ester (II) R<SP>1</SP>.CO.O.CH(R<SP>3</SP>). CO.R<SP>2</SP> with ammonia or a salt thereof or urea; (b) if R<SP>1</SP> is a carboxylic acid amide radical, reacting the corresponding acid with an alkyl haloformate followed by reaction with ammonia; (c) where R<SP>1</SP> is an alkyl ester or an acyloxymethyl ester of an acid radical, reacting the corresponding acid with an alkanol or acyloxy methyl halide respectively; or (d) cyclizing an α-acylamino-ketone R<SP>3</SP>.CO.CH(NHCOR<SP>4</SP>).R<SP>2</SP>, in which R<SP>4</SP> is the same as R<SP>1</SP> or is a radical convertible thereto, and if necessary converting R<SP>4</SP> to R<SP>1</SP>. The intermediate ketoesters of Formula (II) above are prepared by esterification of the α- hydroxyketone R<SP>3</SP>-CH(OH)-COR<SP>2</SP> or a corresponding compound in which (OH) is replaced by halogen. Pharmaceutical compositions comprise a compound of Formula (I) together with a suitable carrier or diluent, are administered orally or parenterally and exhibit anti-inflammatory activity.
GB5620366A 1966-11-18 1966-12-15 Oxazoles Expired GB1206403A (en)

Priority Applications (29)

Application Number Priority Date Filing Date Title
GB5620366A GB1206403A (en) 1966-12-15 1966-12-15 Oxazoles
IL2880367A IL28803A (en) 1966-11-18 1967-10-23 Oxazole and thiazole compounds,their preparation and pharmaceutical compositions containing them
FI304067A FI50416C (en) 1966-11-18 1967-11-10 Process for the preparation of new therapeutically useful trisubstituted branches sols and thiazoles and their acid addition salts
PL12355567A PL72562B1 (en) 1966-11-18 1967-11-13 Substd oxazoles and thiazoles[CH528531A]
NL6715532.A NL157012B (en) 1966-11-18 1967-11-15 PROCESS FOR THE PREPARATION OF PHARMACEUTICAL PREPARATIONS WITH ANTI-INFLAMMATORY ACTION, PREPARED PRODUCTS SO OBTAINED, AND PROCESS FOR PREPARING ANTI-INFLAMMATORY EFFECTIVE HETEROCYCLICAL COMPOUNDS.
CH1606467A CH528531A (en) 1966-11-18 1967-11-16 Substd oxazoles and thiazoles
CH1717071A CH556351A (en) 1966-11-18 1967-11-16 PROCESS FOR PREPARING NEW TRISUBSTITUTED OXAZOLES.
BE706625A BE706625A (en) 1966-11-18 1967-11-16
CH1717171A CH545310A (en) 1966-11-18 1967-11-16 Process for the preparation of new trisubstituted oxazoles
CH1717271A CH536311A (en) 1966-11-18 1967-11-16 Substd oxazoles and thiazoles
CH1717371A CH560205A5 (en) 1966-11-18 1967-11-16
CH1716971A CH545309A (en) 1966-11-18 1967-11-16 Process for the preparation of new trisubstituted oxazoles
LU54891D LU54891A1 (en) 1966-11-18 1967-11-16
CH1648872A CH554884A (en) 1966-11-18 1967-11-16 PROCESS FOR THE PRODUCTION OF NEW TRISUBSTITUTED OXAZOLES OR THIAZOLE.
CH1485573A CH560203A5 (en) 1966-11-18 1967-11-16
CH1716871A CH545308A (en) 1966-11-18 1967-11-16 Process for the preparation of new trisubstituted oxazoles
FR128733A FR8018M (en) 1966-11-18 1967-11-17
DE19671795822 DE1795822C2 (en) 1966-11-18 1967-11-17 Thiazolylalkanecarboxylic acids, process for their preparation and anti-inflammatory preparation
JP7368167A JPS4938267B1 (en) 1966-11-18 1967-11-17
FR1584222D FR1584222A (en) 1966-11-18 1967-11-17
DE19671670005 DE1670005C2 (en) 1966-11-18 1967-11-17 β- (4,5-diphenyloxazol-2-yl) propionic acid or a pharmaceutically acceptable salt thereof, processes for the preparation of these compounds and pharmaceutical preparations containing these compounds
SE1585567A SE369307B (en) 1966-11-18 1967-11-17
ES347319A ES347319A1 (en) 1966-11-18 1967-11-17 A procedure for the preparation of new heterociclic aromatic compounds. (Machine-translation by Google Translate, not legally binding)
IT2286567A IT1060876B (en) 1966-11-18 1967-11-18 Aryl-oxazole derivs - anti-inflammatory agents
YU244367A YU33830B (en) 1966-12-15 1967-12-12 Process for preparing oxazoles
MY7100197A MY7100197A (en) 1966-12-15 1971-12-31 Oxazoles
YU249673A YU33868B (en) 1966-12-15 1973-09-21 Process for preparing oxazoles
SE7316107A SE422209B (en) 1966-11-18 1973-11-28 INTERMEDIATE FOR USE FOR THE PREPARATION OF NEW 1.3-O X 20L AND 1,3-THIAZOLD DERIVATIVES
IN1519/CAL/74A IN137972B (en) 1966-12-15 1974-07-08

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB5620366A GB1206403A (en) 1966-12-15 1966-12-15 Oxazoles

Publications (1)

Publication Number Publication Date
GB1206403A true GB1206403A (en) 1970-09-23

Family

ID=10476023

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5620366A Expired GB1206403A (en) 1966-11-18 1966-12-15 Oxazoles

Country Status (3)

Country Link
GB (1) GB1206403A (en)
MY (1) MY7100197A (en)
YU (2) YU33830B (en)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4190584A (en) 1976-08-13 1980-02-26 John Wyeth & Brother Limited Process for preparing oxazoles
EP0063884A1 (en) * 1981-04-28 1982-11-03 JOHN WYETH &amp; BROTHER LIMITED Oxazole derivatives, their preparation and use
EP0434034A1 (en) * 1989-12-20 1991-06-26 Bristol-Myers Squibb Company Oxazole derivatives
FR2663331A1 (en) * 1990-06-14 1991-12-20 Bellon Labor Sa Roger NEW OXAZOLE DERIVATIVES, THEIR PREPARATION AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM.
WO1992004334A1 (en) * 1990-09-11 1992-03-19 Smith Kline & French Laboratories Limited Compounds
US5239080A (en) * 1989-02-08 1993-08-24 Takeda Chemical Industries, Ltd. Oxazole compounds and their use as antidiabetic and bone-reduction inhibitory agents
US5371098A (en) * 1990-02-01 1994-12-06 Takeda Chemical Industries, Ltd. Use of oxazole compounds to treat osteoporosis
EP0727998A1 (en) * 1993-11-08 1996-08-28 Smithkline Beecham Corporation Oxazoles for treating cytokine mediated diseases
US6030643A (en) * 1996-05-20 2000-02-29 G.D. Searle & Co. Potassium, sodium and tris oxaprozin salt pharmaceutical formulations
EP1095937A1 (en) * 1999-10-27 2001-05-02 L'oreal Process for the preparation of trisubstituted oxazoles
US6362209B1 (en) 1994-12-20 2002-03-26 Japan Tobacco Inc. Heterocyclic aromatic oxazole compounds and use thereof
WO2004065374A1 (en) * 2003-01-17 2004-08-05 Astellas Pharma Inc. Oxazole derivatives as inhibitors of cyclooxygenase
JP2004250401A (en) * 2003-02-21 2004-09-09 Shizuoka Coffein Co Ltd Oxazole derivative
EP2266590A2 (en) 2002-02-22 2010-12-29 Shire LLC Active agent delivery sytems and methods for protecting and administering active agents

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4190584A (en) 1976-08-13 1980-02-26 John Wyeth & Brother Limited Process for preparing oxazoles
EP0063884A1 (en) * 1981-04-28 1982-11-03 JOHN WYETH &amp; BROTHER LIMITED Oxazole derivatives, their preparation and use
US4465838A (en) * 1981-04-28 1984-08-14 John Wyeth & Brother Limited Oxaprozin calcium salt
US4532253A (en) * 1981-04-28 1985-07-30 John Wyeth & Brother Limited Oxaprozin calcium salt pharmaceutical compositions
US5239080A (en) * 1989-02-08 1993-08-24 Takeda Chemical Industries, Ltd. Oxazole compounds and their use as antidiabetic and bone-reduction inhibitory agents
EP0434034A1 (en) * 1989-12-20 1991-06-26 Bristol-Myers Squibb Company Oxazole derivatives
US5371098A (en) * 1990-02-01 1994-12-06 Takeda Chemical Industries, Ltd. Use of oxazole compounds to treat osteoporosis
FR2663331A1 (en) * 1990-06-14 1991-12-20 Bellon Labor Sa Roger NEW OXAZOLE DERIVATIVES, THEIR PREPARATION AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM.
WO1991019714A1 (en) * 1990-06-14 1991-12-26 Laboratoire Roger Bellon Novel oxazole derivatives, a preparation method therefor and pharmaceutical compositions containing same
WO1992004334A1 (en) * 1990-09-11 1992-03-19 Smith Kline & French Laboratories Limited Compounds
EP0727998A1 (en) * 1993-11-08 1996-08-28 Smithkline Beecham Corporation Oxazoles for treating cytokine mediated diseases
EP0727998B1 (en) * 1993-11-08 2004-01-21 Smithkline Beecham Corporation Oxazoles for treating cytokine mediated diseases
US6362209B1 (en) 1994-12-20 2002-03-26 Japan Tobacco Inc. Heterocyclic aromatic oxazole compounds and use thereof
US6030643A (en) * 1996-05-20 2000-02-29 G.D. Searle & Co. Potassium, sodium and tris oxaprozin salt pharmaceutical formulations
EP1095937A1 (en) * 1999-10-27 2001-05-02 L'oreal Process for the preparation of trisubstituted oxazoles
FR2800373A1 (en) * 1999-10-27 2001-05-04 Oreal PROCESS FOR THE PREPARATION OF TRISUBSTITUTED OXAZOLES
US6333414B1 (en) 1999-10-27 2001-12-25 L'ORéAL S.A. Process for the synthesis of trisubstituted oxazoles
EP2266590A2 (en) 2002-02-22 2010-12-29 Shire LLC Active agent delivery sytems and methods for protecting and administering active agents
EP2316469A1 (en) 2002-02-22 2011-05-04 Shire LLC Delivery system and methods for protecting and administering dextroamphetamine
EP2316468A1 (en) 2002-02-22 2011-05-04 Shire LLC Delivery system and methods for protecting and administering dextroamphetamine
WO2004065374A1 (en) * 2003-01-17 2004-08-05 Astellas Pharma Inc. Oxazole derivatives as inhibitors of cyclooxygenase
JP2004250401A (en) * 2003-02-21 2004-09-09 Shizuoka Coffein Co Ltd Oxazole derivative

Also Published As

Publication number Publication date
YU249673A (en) 1977-12-31
YU33830B (en) 1978-06-30
YU33868B (en) 1978-06-30
YU244367A (en) 1977-12-31
MY7100197A (en) 1971-12-31

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Legal Events

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