IE32086L - Oxazole derivatives - Google Patents

Oxazole derivatives

Info

Publication number
IE32086L
IE32086L IE59268A IE59268A IE32086L IE 32086 L IE32086 L IE 32086L IE 59268 A IE59268 A IE 59268A IE 59268 A IE59268 A IE 59268A IE 32086 L IE32086 L IE 32086L
Authority
IE
Ireland
Prior art keywords
phenyl
oxazole
give
acids
prepared
Prior art date
Application number
IE59268A
Other versions
IE32086B1 (en
Original Assignee
Wyeth John & 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 Wyeth John & Brother Ltd filed Critical Wyeth John & Brother Ltd
Publication of IE32086L publication Critical patent/IE32086L/en
Publication of IE32086B1 publication Critical patent/IE32086B1/en

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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Biophysics (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Hematology (AREA)
  • Biomedical Technology (AREA)
  • Anesthesiology (AREA)
  • Engineering & Computer Science (AREA)
  • Pulmonology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

1,226,548. Oxazole derivatives. JOHN WYETH & BRO. Ltd. 15 May, 1968 [14 June, 1967; 16 Aug., 1967], Nos. 27382/67 and 37598/67. Heading C2C. [Also in Division A5] Novel compounds I and their acid addition salts in which R<SP>1</SP> is phenyl, halophenyl, alkylphenyl, alkoxyphenyl, nitrophenyl, haloalkylphenyl, mercaptophenyl, alkylthiophenyl, aminophenyl, dialkylaminophenyl, alkylsulphonylphenyl, naphthyl or heteroaryl; R<SP>2</SP> is H, 1-4 C alkyl, aryl or heteroaryl; and R<SP>3</SP> is a 2-6 C aliphatic carboxylic acid radical attached via a C of its aliphatic chain or an ester, amide, salt or hydroxamic acid derivative of the COOH group in said radical R<SP>3</SP>; with the provisos (a) that when R<SP>1</SP> is phenyl optionally substituted by CF 3 or up to 2 halo and when R<SP>2</SP> is 5-H, then R<SP>3</SP> has at least 2 C in a straight chain between the oxazole ring and the COOH group or its derivative and (b) that if R<SP>1</SP> is phenyl and R<SP>3</SP> is a 4-acrylic or n-propionic acid radical R<SP>2</SP> is not H; are prepared by (a) when R<SP>3</SP> and R<SP>2</SP> are in the 4- and 5-positions respectively, reacting (where R<SP>4</SP> is as R<SP>3</SP> or is convertible thereto) with R<SP>1</SP>CONH 2 ; (b) when R<SP>3</SP> and R<SP>2</SP> are in the 5- and 4-positions respectively, reacting alkyl -OOC-CH(hal)COR<SP>2</SP> in the form of an enamine with ammonia or an amine and an aroyl peroxide to give compounds V which are then cyclized; (c) when R<SP>3</SP> and R<SP>2</SP> are positioned as in (b), reacting alkyl OOC-CH(M)COR<SP>2</SP> (M is an alkali metal) with an aroyl peroxide to give compounds VI which are then cyclized in the presence of a N-donating agent to give I; (d) hydrolysis of esters to give acids; (e) hydrolysis of nitriles to amides and acids; or (f) esterification of the acids. Intermediates isolated are 4-chloromethyl-2- phenyl-oxazole, prepared from benzamide and sym-dichloroacetone; and 4-cyanomethyl-2- phenyl-oxazole, prepared from the former intermediate and NaCN. [GB1226548A]
IE59268A 1967-06-14 1968-05-17 Oxazole derivatives IE32086B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB2738267 1967-06-14
GB3759867 1967-08-16

Publications (2)

Publication Number Publication Date
IE32086L true IE32086L (en) 1968-12-14
IE32086B1 IE32086B1 (en) 1973-04-04

Family

ID=26258780

Family Applications (1)

Application Number Title Priority Date Filing Date
IE59268A IE32086B1 (en) 1967-06-14 1968-05-17 Oxazole derivatives

Country Status (15)

Country Link
JP (1) JPS4938268B1 (en)
BE (1) BE713392A (en)
CH (1) CH560204A5 (en)
DE (1) DE1770177A1 (en)
DK (1) DK137674B (en)
ES (1) ES352579A1 (en)
FR (2) FR8056M (en)
GB (1) GB1226548A (en)
IE (1) IE32086B1 (en)
IL (1) IL29654A (en)
IT (1) IT1053686B (en)
LU (1) LU55869A1 (en)
NL (1) NL6805103A (en)
PL (1) PL71145B1 (en)
SE (1) SE374745B (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE794096A (en) * 1972-08-07 1973-05-16 Lepetit Spa 2,4,5-TRISUBSTITU OXAZOLES AND THEIR PREPARATION
JPS58183676A (en) * 1982-04-19 1983-10-26 Takeda Chem Ind Ltd Oxazole derivative
EP0934937B1 (en) * 1990-11-30 2002-02-27 Otsuka Pharmaceutical Co., Ltd. Azole derivatives as superoxide radical inhibitor
MY128323A (en) 1996-09-30 2007-01-31 Otsuka Pharma Co Ltd Thiazole derivatives for inhibition of cytokine production and of cell adhesion

Also Published As

Publication number Publication date
FR1587052A (en) 1970-03-13
LU55869A1 (en) 1968-07-09
PL71145B1 (en) 1974-04-30
GB1226548A (en) 1971-03-31
IE32086B1 (en) 1973-04-04
JPS4938268B1 (en) 1974-10-16
DE1770177A1 (en) 1972-03-16
FR8056M (en) 1970-07-06
IL29654A (en) 1974-05-16
BE713392A (en) 1968-10-08
DK137674C (en) 1978-09-25
DK137674B (en) 1978-04-17
CH560204A5 (en) 1975-03-27
ES352579A1 (en) 1970-01-01
NL6805103A (en) 1968-12-16
SE374745B (en) 1975-03-17
IT1053686B (en) 1981-10-10

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