GB1353789A - Process for producing 2-n-monosubstituted amino-phenyl ketones and their conversion to quinazoline derivatives - Google Patents

Process for producing 2-n-monosubstituted amino-phenyl ketones and their conversion to quinazoline derivatives

Info

Publication number
GB1353789A
GB1353789A GB5661371A GB5661371A GB1353789A GB 1353789 A GB1353789 A GB 1353789A GB 5661371 A GB5661371 A GB 5661371A GB 5661371 A GB5661371 A GB 5661371A GB 1353789 A GB1353789 A GB 1353789A
Authority
GB
United Kingdom
Prior art keywords
formula
alkyl
phenyl
compound
alkali metal
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
GB5661371A
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.)
Sumitomo Chemical Co Ltd
Original Assignee
Sumitomo Chemical 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 Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd
Publication of GB1353789A publication Critical patent/GB1353789A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/50—Ketonic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom

Abstract

1353789 Quinazolinones; 2-(N-mono-substituted amino)-phenyl-ketones SUMITOMO CHEMICAL CO Ltd 6 Dec 1971 [8 Dec 1970] 56613/71 Heading C2C 2 - (N - mono - substituted amino) - phenylketone derivatives of Formula (V) wherein R 1 and R 2 are individually -H, C 1-4 alkyl, C 1-4 alkoxy, -NO 2 , -CF 3 , C 1-4 alkylthio, C 1-4 alkylsulphonyl or halogen; R 3 is phenyl, halophenyl, C 1-4 alkyl phenyl, C 1-4 alkoxyphenyl, CF 3 -phenyl, C 3-6 cycloalkyl, C 5-6 cycloalkenyl, pyridyl, furyl, thienyl, or naphthyl; and R is C 1-4 alkyl, C 2-5 alkenyl, C 1-4 haloalkyl, aralkyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-4 -alkyl, C 1-4 alkoxy-C 1-4 -alkyl, C 1-4 hydroxyalkyl, C 2-5 alkanoyloxy-C 1-4 -alkyl, trihalomethyl - C 1-4 - alkyl, C 1-4 alkylthio C 1-4 alkyl or a group of the formula (n is an integer from 1 to 3 and R 4 and R 5 are each an alkyl group or R 4 and R 5 together with the common nitrogen atom form an unsubstituted or substituted 5- or 6-membered heterocyclic ring, which may contain a further hetero atom) are obtained by contacting a 2-aminophenyl ketone of Formula (II) with an alkali metal or compound thereof in the presence of a solvent to form an alkali metal salt of Formula (III) wherein M is an alkali metal atom, and reacting the resultant salt in the presence of a solvent with a compound which is a reactive derivative, e.g. or halide or sulphonic acid ester, of the compound of formula, R-OH. The alkali metal compound used is preferably a hydride or amide or an organolithium compound and preferred solvents are benzene, toluene xylene, monochlorobenzene, dimethylacetamide, diethylacetamide, dimethylformamide, dioxane, dimethylsulphoxide and mixtures thereof. Quinazoline derivatives for Formula (I) wherein R, R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> are as defined for Formula (V), are prepared from the 2-(N-monosubstituted amino)-phenyl ketones of Formula (V) by reacting the latter with a C 1-4 alkyl haloformate or a benzyl haloformate to give a carbamate derivative of Formula (VI) wherein R 6 is a C 1-4 alkyl group or a benzyl group, and then heating the compound of Formula (VI) with ammonia. The quinazoline derivatives of Formula (I), which are said to include novel compounds, possess pharmacological properties, particularly anti-inflammatory and analgesic effects with lower toxicity than phenylbutazone. Many examples of compounds of both Formulµ (I) and (V) are listed together with melting point data. The specific example describes in detail the preparation of 2-ethylamino - 5 - chlorobenzophenone and 1 - ethyl- 4-phenyl-6-chloro-2(1H)-quinazolinone.
GB5661371A 1970-12-08 1971-12-06 Process for producing 2-n-monosubstituted amino-phenyl ketones and their conversion to quinazoline derivatives Expired GB1353789A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP10997570A JPS5118423B1 (en) 1970-12-08 1970-12-08

Publications (1)

Publication Number Publication Date
GB1353789A true GB1353789A (en) 1974-05-22

Family

ID=14523882

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5661371A Expired GB1353789A (en) 1970-12-08 1971-12-06 Process for producing 2-n-monosubstituted amino-phenyl ketones and their conversion to quinazoline derivatives

Country Status (13)

Country Link
JP (1) JPS5118423B1 (en)
AT (1) AT319919B (en)
AU (1) AU448048B2 (en)
BE (1) BE776332A (en)
CA (1) CA1002046A (en)
CH (1) CH558800A (en)
DD (1) DD95841A5 (en)
FR (1) FR2117301A5 (en)
GB (1) GB1353789A (en)
HU (1) HU163952B (en)
NL (1) NL7116769A (en)
SE (1) SE397518B (en)
SU (1) SU517242A3 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004056365A2 (en) * 2002-12-23 2004-07-08 Novartis Ag Derivatives of aryl-quinazoline/aryl-2amino-phenyl methanone which promote the release of parathyroid hormone
US8476286B2 (en) 2001-06-15 2013-07-02 Novartis Ag Quinazoline derivatives which promote the release of parathyroid hormone

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5392915U (en) * 1976-12-28 1978-07-29
US6063921A (en) * 1997-11-20 2000-05-16 Pharm-Eco Laboratories, Inc. Synthesis of 11-aryl-5,6-dihydro-11H-dibenz[b,e]azepines

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8476286B2 (en) 2001-06-15 2013-07-02 Novartis Ag Quinazoline derivatives which promote the release of parathyroid hormone
WO2004056365A2 (en) * 2002-12-23 2004-07-08 Novartis Ag Derivatives of aryl-quinazoline/aryl-2amino-phenyl methanone which promote the release of parathyroid hormone
WO2004056365A3 (en) * 2002-12-23 2004-08-19 Novartis Ag Derivatives of aryl-quinazoline/aryl-2amino-phenyl methanone which promote the release of parathyroid hormone
EP1844780A2 (en) * 2002-12-23 2007-10-17 Novartis Pharma AG Derivatives of aryl-quinazoline/aryl-2-amino-phenyl methanone which promote the release of parathyroid hormone
AU2003296710B2 (en) * 2002-12-23 2007-11-15 Novartis Ag Derivatives of aryl-quinazoline/aryl-2-amino-phenyl methanone which promote the release of parathyroid hormone
EP1844780A3 (en) * 2002-12-23 2008-03-05 Novartis Pharma AG Derivatives of aryl-quinazoline/aryl-2-amino-phenyl methanone which promote the release of parathyroid hormone
US8569317B2 (en) 2002-12-23 2013-10-29 Novartis Ag Aryl-quinazoline/aryl-2amino-phenyl methanone derivatives

Also Published As

Publication number Publication date
DD95841A5 (en) 1973-02-20
CA1002046A (en) 1976-12-21
SE397518B (en) 1977-11-07
HU163952B (en) 1973-11-28
AU3634071A (en) 1973-06-07
AU448048B2 (en) 1974-05-09
AT319919B (en) 1975-01-10
FR2117301A5 (en) 1972-07-21
NL7116769A (en) 1972-06-12
SU517242A3 (en) 1976-06-05
JPS5118423B1 (en) 1976-06-09
DE2159655A1 (en) 1972-06-22
BE776332A (en) 1972-04-04
DE2159655B2 (en) 1975-10-23
CH558800A (en) 1975-02-14

Similar Documents

Publication Publication Date Title
GB1489280A (en) Indazole derivatives
GB1332477A (en) Basic azo dyes free from sulphonic acid groups their production and use
US4551526A (en) Synthesis of alpha-aminonitriles
GB1131191A (en) New imidazole derivatives, their preparation and use
IE37452B1 (en) 2,4-diamino-5-benzylpyrimidines and processes for their production
DK599385D0 (en) PROCEDURE FOR THE PREPARATION OF AMID DERIVATIVES
GB1353789A (en) Process for producing 2-n-monosubstituted amino-phenyl ketones and their conversion to quinazoline derivatives
DE2165056C3 (en) Process for the production of CMnazollnonen
SE7509271L (en) WAY TO PRODUCE CHINOXALINE AND CHINAZOLINE DERIVATIVES
GB1357852A (en) Process for the preparation of 1,2,4-triazin-5-ones
SK284800B6 (en) Process for preparing pyrazole derivatives
GB1429141A (en) 1-substituted pyrazol-5-ones their production and their medicinal use
GB1317338A (en) Quinazoline derivatives and processes for producing them
US4096144A (en) Process for preparing quinazolinone derivatives and their 2-(N-mono-substituted amino)-phenyl ketone intermediate derivatives
GB1139458A (en) 2-phenylamino-2-oxazolines and their production
GB888686A (en) Phosphorus-containing amino-triazole derivatives
ES354273A1 (en) New quinazoline compounds and methods for their production
GB1138530A (en) 2-phenylamino-2-oxazolines and their production
GB1230299A (en)
SE7610051L (en) NEW DERIVATIVES OF 1,2,4-OXADIAZIN-5-ON
GB1361249A (en) 3-sulphoalkyl-6-hydroxy-pyrid--2--ones their manufacture and use
GB1305518A (en)
GB1437895A (en) Thiazolylurea derivatives and process for the preparation thereof
GB1474985A (en) Quinazolinones processes for producing them and compositions containing them
GB1479126A (en) Substituted ureas and the use thereof as herbicides

Legal Events

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