GB1381031A – Imidazole derivatives and processes for their production
– Google Patents
GB1381031A – Imidazole derivatives and processes for their production
– Google Patents
Imidazole derivatives and processes for their production
Info
Publication number
GB1381031A
GB1381031A
GB1978172A
GB1978172A
GB1381031A
GB 1381031 A
GB1381031 A
GB 1381031A
GB 1978172 A
GB1978172 A
GB 1978172A
GB 1978172 A
GB1978172 A
GB 1978172A
GB 1381031 A
GB1381031 A
GB 1381031A
Authority
GB
United Kingdom
Prior art keywords
prepared
reacting
phenyl
ketone
ammonia
Prior art date
1971-05-10
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
GB1978172A
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.)
Novartis AG
Original Assignee
Ciba Geigy AG
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.)
1971-05-10
Filing date
1972-04-28
Publication date
1975-01-22
1971-05-10
Priority claimed from CH687571A
external-priority
patent/CH554415A/en
1972-04-28
Application filed by Ciba Geigy AG
filed
Critical
Ciba Geigy AG
1975-01-22
Publication of GB1381031A
publication
Critical
patent/GB1381031A/en
Status
Expired
legal-status
Critical
Current
Links
Espacenet
Global Dossier
Discuss
Classifications
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07D—HETEROCYCLIC COMPOUNDS
C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having 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
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
Abstract
1381031 Phenyl-heteroaromatic substituted imidazole derivatives CIBA-GEIGY AG 28 April 1972 [11 May 1971 22 March 1972] 19781/72 Heading C2C Novel compounds of the Formula I wherein R 1 is C 1-6 alkyl, cycloalkyl or phenyl which is optionally substituted by one or more halogen or C 1-6 alkyl or alkoxy substituents and one of the groups R 2 and R 3 is phenyl optionally substituted by one or more halogen, hydroxy or C 1-6 alkyl, alkoxy, alkylthio or alkylsulphonyl substituents and the other represents a 6-membered heteroaromatic radical containing 1 or 2 ring nitrogen atoms, and N- oxides and salts thereof may be prepared by (a) reacting a diketone II or a mono-oxime or N-oxide thereof with ammonia and an aldehyde R 1 .CHO; (b) reacting an amide V with ammonia; (c) reacting a reactive ester of IIa with an amidine R 1 C(:NH)NH 2 or a salt thereof; (d) reacting an oxazole VII with ammonia and optionally forming an N- oxide or converting an N-oxide to a free compound and/or optionally forming a salt or converting a salt to a free base. The intermediate diketones II may be prepared by oxidation of the monoketones R 2 COCH 2 R 3 or R 2 CH 2 COR 3 , or the olefin R 2 C : CR 3 . The intermediate benzyl pyridyl ketones may be prepared by reaction of a pyridine carboxylic ester with a phenylacetic acid ester in the presence of strong base. Phenyl – (pyrazinyl – 2 – methyl) – ketone may be prepared by reaction of 2-methyl pyrazine with sodamide followed by methyl benzoate. (α – Hydroxyimino – benzyl) – (3 – pyridyl)- ketone may be prepared by reaction of benzyl-(3- pyridyl)-ketone with nitrous acid followed by basicification. Pharmaceutical compositions of the compounds I show anti-inflammatory, antipyretic, antiphlogistic and analgesic activity when administered orally, rectally, parenterally or topically with the usual excipients.
GB1978172A
1971-05-10
1972-04-28
Imidazole derivatives and processes for their production
Expired
GB1381031A
(en)
Applications Claiming Priority (4)
Application Number
Priority Date
Filing Date
Title
CH687571A
CH554415A
(en)
1970-06-01
1971-05-10
PROCESS FOR THE PRODUCTION OF LEMONIC ACID BY SUBMERSE FERMENTATION.
CH696771A
CH561202A5
(en)
1971-05-10
1971-05-11
CH697571
1971-05-12
CH425072A
CH579072A5
(en)
1971-05-10
1972-03-22
Publications (1)
Publication Number
Publication Date
GB1381031A
true
GB1381031A
(en)
1975-01-22
Family
ID=27428754
Family Applications (1)
Application Number
Title
Priority Date
Filing Date
GB1978172A
Expired
GB1381031A
(en)
1971-05-10
1972-04-28
Imidazole derivatives and processes for their production
Country Status (10)
Country
Link
AT
(4)
AT316544B
(en)
AU
(1)
AU472065B2
(en)
BE
(1)
BE783244A
(en)
CA
(1)
CA1012148A
(en)
CH
(5)
CH561718A5
(en)
DE
(1)
DE2221546A1
(en)
FR
(1)
FR2137740B1
(en)
GB
(1)
GB1381031A
(en)
NL
(1)
NL7206346A
(en)
SE
(1)
SE405731B
(en)
Cited By (5)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
EP0032113A2
(en)
*
1980-01-07
1981-07-15
E.I. Du Pont De Nemours And Company
Antiinflammatory 4,5-diaryl-alpha-(polyhaloalkyl)-1H-imidazole-2-methanols
US4372964A
(en)
*
1980-10-30
1983-02-08
E. I. Du Pont De Nemours And Company
Antiinflammatory 4,5-diaryl-1H-imidazole-2-methanols
US5620999A
(en)
*
1994-07-28
1997-04-15
Weier; Richard M.
Benzenesulfonamide subtituted imidazolyl compounds for the treatment of inflammation
WO2000061576A1
(en)
*
1999-04-09
2000-10-19
Smithkline Beecham Corporation
Triarylimidazoles
WO2001072737A1
(en)
*
2000-03-27
2001-10-04
Smithkline Beecham Corporation
Triarylimidazole derivatives as cytokine inhibitors
Families Citing this family (17)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
CA1175431A
(en)
*
1980-07-25
1984-10-02
Alfred Sallmann
Tri-substituted imidazole derivatives, processes for their manufacture, pharmaceutical preparations containing them, and their use
GB2123831B
(en)
*
1981-07-20
1986-01-15
Ciba Geigy Ag
Trisubstituted oxazo compounds
AU554104B2
(en)
*
1981-09-01
1986-08-07
F. Hoffmann-La Roche Ag
Heterocyclic compounds and fungicides containing same
EP0084756A1
(en)
*
1982-01-22
1983-08-03
Ciba-Geigy Ag
Trisubstituted oxaza compounds
EP0084757A1
(en)
*
1982-01-25
1983-08-03
Ciba-Geigy Ag
Trisubstituted diaza derivatives
IL83467A0
(en)
*
1986-08-15
1988-01-31
Fujisawa Pharmaceutical Co
Imidazole derivatives,processes for their preparation and pharmaceutical compositions containing the same
MX9300141A
(en)
*
1992-01-13
1994-07-29
Smithkline Beecham Corp
NOVEL IMIDAZOLE COMPOUNDS, PROCEDURE FOR THE PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING IT.
US5656644A
(en)
*
1994-07-20
1997-08-12
Smithkline Beecham Corporation
Pyridyl imidazoles
US5916891A
(en)
1992-01-13
1999-06-29
Smithkline Beecham Corporation
Pyrimidinyl imidazoles
ES2053401B1
(en)
*
1992-01-13
1995-03-01
Smithkline Beecham Corp
IMIDAZOLE COMPOUNDS AND PROCEDURES FOR ITS PREPARATION.
WO1995013067A1
(en)
*
1993-11-08
1995-05-18
Smithkline Beecham Corporation
Oxazoles for treating cytokine mediated diseases
US6426360B1
(en)
*
1994-07-28
2002-07-30
G D Searle & Co.
4,5-substituted imidazolyl compounds for the treatment of inflammation
EP0797575B1
(en)
*
1994-12-13
2003-10-15
F. Hoffmann-La Roche Ag
Imidazole derivatives as protein kinase inhibitors in particular egf-r tyrosine kinase
US6130334A
(en)
*
1998-04-15
2000-10-10
Merck & Co., Inc.
Process for making 2-aryl-3-aryl-5-halo pyridines useful as COX-2 inhibitors
TW492959B
(en)
*
1997-04-18
2002-07-01
Merck & Co Inc
Process for making 2-aryl-3-aryl-5-halo pyridines useful as cox-2 inhibitors
US6127545A
(en)
*
1997-04-18
2000-10-03
Merck & Co., Inc.
Process for making 2-aryl-3-aryl-5-halo pyridines useful as COX-2 inhibitors
AR029803A1
(en)
*
2000-02-21
2003-07-16
Smithkline Beecham Plc
IMIDAZOLS REPLACED WITH PIRIDILE AND PHARMACEUTICAL COMPOSITIONS THAT UNDERSTAND THEM
Family Cites Families (2)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
US3192211A
(en)
*
1962-05-03
1965-06-29
Nl Combinatie Chem Ind
5-phenyl-5-(2-pyrazyl)-hydantoin
US3538104A
(en)
*
1969-02-28
1970-11-03
Geigy Chem Corp
Pyridyl-2-imidazolones
1971
1971-05-11
CH
CH76975A
patent/CH561718A5/xx
not_active
IP Right Cessation
1971-05-11
CH
CH696771A
patent/CH561202A5/xx
not_active
IP Right Cessation
1971-05-11
CH
CH76875A
patent/CH561717A5/xx
not_active
IP Right Cessation
1971-05-11
CH
CH76775A
patent/CH561716A5/xx
not_active
IP Right Cessation
1972
1972-03-22
CH
CH425072A
patent/CH579072A5/xx
not_active
IP Right Cessation
1972-04-27
SE
SE7205565A
patent/SE405731B/en
unknown
1972-04-28
GB
GB1978172A
patent/GB1381031A/en
not_active
Expired
1972-05-03
DE
DE19722221546
patent/DE2221546A1/en
not_active
Withdrawn
1972-05-08
CA
CA141,520A
patent/CA1012148A/en
not_active
Expired
1972-05-09
AU
AU42055/72A
patent/AU472065B2/en
not_active
Expired
1972-05-10
FR
FR7216738A
patent/FR2137740B1/fr
not_active
Expired
1972-05-10
AT
AT408972A
patent/AT316544B/en
not_active
IP Right Cessation
1972-05-10
AT
AT386573A
patent/AT319939B/en
not_active
IP Right Cessation
1972-05-10
BE
BE783244A
patent/BE783244A/en
not_active
IP Right Cessation
1972-05-10
AT
AT386673A
patent/AT319940B/en
not_active
IP Right Cessation
1972-05-10
NL
NL7206346A
patent/NL7206346A/xx
not_active
Application Discontinuation
1972-05-10
AT
AT386773A
patent/AT319941B/en
not_active
IP Right Cessation
Cited By (9)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
EP0032113A2
(en)
*
1980-01-07
1981-07-15
E.I. Du Pont De Nemours And Company
Antiinflammatory 4,5-diaryl-alpha-(polyhaloalkyl)-1H-imidazole-2-methanols
EP0032113A3
(en)
*
1980-01-07
1981-08-05
E.I. Du Pont De Nemours And Company
Antiinflammatory 4,5-diaryl-alpha-(polyhaloalkyl)-1h-imidazole-2-methanols
US4372964A
(en)
*
1980-10-30
1983-02-08
E. I. Du Pont De Nemours And Company
Antiinflammatory 4,5-diaryl-1H-imidazole-2-methanols
US5620999A
(en)
*
1994-07-28
1997-04-15
Weier; Richard M.
Benzenesulfonamide subtituted imidazolyl compounds for the treatment of inflammation
EP1211244A2
(en)
*
1994-07-28
2002-06-05
G.D. Searle & Co.
4,5-substitued imidazolyl compounds for the treatment of inflammation
EP1211244A3
(en)
*
1994-07-28
2002-06-12
G.D. Searle & Co.
4,5-substitued imidazolyl compounds for the treatment of inflammation
WO2000061576A1
(en)
*
1999-04-09
2000-10-19
Smithkline Beecham Corporation
Triarylimidazoles
WO2001072737A1
(en)
*
2000-03-27
2001-10-04
Smithkline Beecham Corporation
Triarylimidazole derivatives as cytokine inhibitors
US6906089B2
(en)
2000-03-27
2005-06-14
Smithkline Beecham Corporation
Triarylimidazole derivatives as cytokine inhibitors
Also Published As
Publication number
Publication date
AT316544B
(en)
1974-07-10
AU4205572A
(en)
1973-11-15
CH561716A5
(en)
1975-05-15
CH579072A5
(en)
1976-08-31
AT319941B
(en)
1975-01-10
CH561718A5
(en)
1975-05-15
FR2137740A1
(en)
1972-12-29
NL7206346A
(en)
1972-11-14
CH561717A5
(en)
1975-05-15
DE2221546A1
(en)
1972-11-16
CA1012148A
(en)
1977-06-14
AT319939B
(en)
1975-01-10
BE783244A
(en)
1972-11-10
CH561202A5
(en)
1975-04-30
AU472065B2
(en)
1976-05-13
SE405731B
(en)
1978-12-27
FR2137740B1
(en)
1975-08-01
AT319940B
(en)
1975-01-10
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Legal Events
Date
Code
Title
Description
1975-06-04
PS
Patent sealed
1985-01-03
PCNP
Patent ceased through non-payment of renewal fee
