GB1064531A

GB1064531A – Substituted 5-carboxyimidazole derivatives and preparation thereof
– Google Patents

GB1064531A – Substituted 5-carboxyimidazole derivatives and preparation thereof
– Google Patents
Substituted 5-carboxyimidazole derivatives and preparation thereof

Info

Publication number
GB1064531A

GB1064531A
GB12665/65A
GB1266565A
GB1064531A
GB 1064531 A
GB1064531 A
GB 1064531A
GB 12665/65 A
GB12665/65 A
GB 12665/65A
GB 1266565 A
GB1266565 A
GB 1266565A
GB 1064531 A
GB1064531 A
GB 1064531A
Authority
GB
United Kingdom
Prior art keywords
alkyl
substituted
acid
esters
alkali metal
Prior art date
1964-04-16
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
GB12665/65A
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.)

Janssen Pharmaceutica NV

Original Assignee
Janssen Pharmaceutica NV
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.)
1964-04-16
Filing date
1965-03-25
Publication date
1967-04-05

1965-03-25
Application filed by Janssen Pharmaceutica NV
filed
Critical
Janssen Pharmaceutica NV

1967-04-05
Publication of GB1064531A
publication
Critical
patent/GB1064531A/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

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

C07D213/36—Radicals substituted by singly-bound nitrogen atoms

C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom

C—CHEMISTRY; METALLURGY

C07—ORGANIC CHEMISTRY

C07D—HETEROCYCLIC COMPOUNDS

C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings

C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members

C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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

C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile 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

Abstract

Substituted 5-carboxyimidazole esters of the formula as the therapeutically active non-toxic acid addition salts thereof wherein R is a straight or branched chain aliphatic radical such as lower alkyl, halo-lower-alkyl, allyl, 2-propynyl or lower-alkoxy-lower-alkyl; R1 is lower-alkyl; and Ar is phenyl, halo-phenyl, lower-alkylphenyl, lower-alkoxy-phenyl, thienyl or pyridyl, the said lower alkyl or alkoxy groups having from 1 to 5 carbon atoms in the chain and preparation thereof either by nitric acid desulphurization of the corresponding 2-mercapto-compound when R in the above formula represents a methyl group or by hydrolysis of compounds of the above formula having a 5-carbo-methoxy group to give the free carboxylic acid, formation of the corresponding acid chloride and subsequent esterification with the appropriate alcohol when R is lower-alkyl (other than methyl), halo-lower-alkyl, allyl, 2-propynyl or lower – alkoxy – lower – alkyl. The above-mentioned 2-mercapto-compounds are obtained by condensing an enol of the formula wherein R is methyl and R1 and Ar have the above significance with an alkali metal thiocyanate under acid conditions. Enols of the second general formula above are prepared by a Claisen formylation of a suitable N-Ar.CH(R1)-substituted – N – formyl – glycine ester, wherein R1 and Ar have the above significance, with an alkyl ester of formic acid in the presence of an alkali metal alkoxide. The reactants preferably contain identical carbalkoxy groups and the enolic product is obtained by acidifying the alkali metal enolate in aqueous solution by acidifying the alkali metal enolate. N – Ar.CH(R1) – substituted – N – formylglycine esters are prepared by acylating the appropriate N-Ar.CH(R1)-substituted glycine ester with, for example, formic acid. N – Ar.CH(R1) – substituted glycine esters are obtained by reacting a primary amine bearing the substituent Ar.CH(R1)-, wherein R1 and Ar have the above significance, with an alkyl ester of chloracetic acid in an inert solvent in the presence of a halogen acid acceptor. Only esters wherein Ar represents a 1-, 2- or 3-pyridyl group are identified. d1 – 1 – (3 – Chlorophenyl)ethylamine and d1-1 – (3,4 – dimethylphenyl)ethylamine are prepared by treating an appropriately substituted acetophenone with ammonium formate or formamide in the presence of formic acid.

GB12665/65A
1964-04-16
1965-03-25
Substituted 5-carboxyimidazole derivatives and preparation thereof

Expired

GB1064531A
(en)

Applications Claiming Priority (1)

Application Number
Priority Date
Filing Date
Title

US360441A

US3354173A
(en)

1964-04-16
1964-04-16
Imidazole carboxylates

Publications (1)

Publication Number
Publication Date

GB1064531A
true

GB1064531A
(en)

1967-04-05

Family
ID=23417963
Family Applications (1)

Application Number
Title
Priority Date
Filing Date

GB12665/65A
Expired

GB1064531A
(en)

1964-04-16
1965-03-25
Substituted 5-carboxyimidazole derivatives and preparation thereof

Country Status (6)

Country
Link

US
(1)

US3354173A
(en)

BE
(1)

BE662474A
(en)

DE
(1)

DE1545988B2
(en)

FR
(2)

FR1604115A
(en)

GB
(1)

GB1064531A
(en)

SE
(1)

SE327708B
(en)

Families Citing this family (18)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

GB1475271A
(en)

*

1975-04-30
1977-06-01
Pfizer Ltd
1-aryl-2-1-imidazolyl-alkyl ethers and thioethers and their use as antifungal agents

DE2732531A1
(en)

*

1977-07-19
1979-02-01
Hoechst Ag

IMIDAZOLE CARBONIC ACIDS AND THEIR DERIVATIVES

JPS54148788A
(en)

*

1978-05-15
1979-11-21
Takeda Chem Ind Ltd
1,2-disubstituted-4-halogenoimidazole-5-acetic acid derivative and its preparation

GR64915B
(en)

*

1978-09-14
1980-06-09
Janssen Pharmaceutica Nv
Improved etomidate-containing compositions

JPS5671073A
(en)

*

1979-11-12
1981-06-13
Takeda Chem Ind Ltd
Imidazole derivative

US4770689A
(en)

*

1986-03-10
1988-09-13
Janssen Pharmaceutica N.V.
Herbicidal imidazole-5-carboxylic acid derivatives

GB8631020D0
(en)

*

1986-12-30
1987-02-04
Janssen Pharmaceutica Nv
1-methyl-1h-imidazole-5-carboxylic acid derivatives

US6878735B2
(en)

*

2002-05-31
2005-04-12
Board Of Trustees Of Michigan State University
Multi-substituted imidazolines and method of use thereof

JPWO2008136428A1
(en)

*

2007-04-27
2010-07-29
武田薬品工業株式会社

Nitrogen-containing 5-membered heterocyclic compound

AU2013242865B2
(en)

*

2008-03-31
2016-05-26
The General Hospital Corporation
Etomidate analogues with improved pharmacokinetic and pharmacodynamic properties

US8557856B2
(en)

*

2008-03-31
2013-10-15
The General Hospital Corporation
Etomidate analogues with improved pharmacokinetic and pharmacodynamic properties

CN102548964B
(en)

2009-07-10
2014-09-24
通用医疗公司
Etomidate analogues that do not inhibit adrenocortical steroid synthesis

BR112014017230A2
(en)

2012-01-13
2020-11-24
The General Hospital Corporation

anesthetic compounds and related methods of use

CN103739553B
(en)

*

2013-12-23
2014-11-12
四川大学华西医院
N-substituted imidazolecarboxylic acid ester chiral compound containing ether side chain, preparation method and application thereof

CN109776509B
(en)

*

2018-01-30
2023-07-07
成都麻沸散医药科技有限公司
N-substituted imidazole formate derivative and application thereof

CN112375039B
(en)

*

2020-11-20
2022-03-08
燃点(南京)生物医药科技有限公司
Novel crystal form A of (R) – (+) -1- (1-phenethyl) -2-mercaptoimidazole-5-carboxylic acid ethyl ester and preparation method thereof

CN113563266A
(en)

*

2021-07-28
2021-10-29
江西汇和化工有限公司
Process for continuously synthesizing prochloraz and intermediate acylate of prochloraz raw material

CN114292236A
(en)

*

2021-12-24
2022-04-08
江苏慈星药业有限公司
Preparation method of etomidate intermediate

Family Cites Families (1)

* Cited by examiner, † Cited by third party

Publication number
Priority date
Publication date
Assignee
Title

FR1184709A
(en)

*

1957-09-21
1959-07-24
Cfmc

New imidazole derivatives, usable as protection agents against ultraviolet rays and their manufacturing processes

1964

1964-04-16
US
US360441A
patent/US3354173A/en
not_active
Expired – Lifetime

1965

1965-03-25
GB
GB12665/65A
patent/GB1064531A/en
not_active
Expired

1965-04-14
DE
DE19651545988
patent/DE1545988B2/en
active
Granted

1965-04-14
BE
BE662474D
patent/BE662474A/xx
unknown

1965-04-14
SE
SE04963/65A
patent/SE327708B/xx
unknown

1965-04-15
FR
FR1604115D
patent/FR1604115A/en
not_active
Expired

1965-07-12
FR
FR24367A
patent/FR4499M/fr
not_active
Expired

Also Published As

Publication number
Publication date

DE1545988A1
(en)

1970-01-29

BE662474A
(en)

1965-10-14

FR1604115A
(en)

1971-07-12

DE1545988B2
(en)

1976-01-29

SE327708B
(en)

1970-08-31

US3354173A
(en)

1967-11-21

FR4499M
(en)

1966-10-10

Similar Documents

Publication
Publication Date
Title

GB1064531A
(en)

1967-04-05

Substituted 5-carboxyimidazole derivatives and preparation thereof

ES371426A1
(en)

1971-10-16

Synthesis of arylchlorocarbonyl ketenes

GB1042631A
(en)

1966-09-14

New fused polycyclic hydrocarbon derivatives and processes for the preparation thereof

ES338638A1
(en)

1968-07-01

New substituted phenylacetic esters, their production and compositions containing them

ES406004A1
(en)

1976-01-16

3-(5-oxyphenethyl)-glutarimides

US3168528A
(en)

1965-02-02

1-(p-nitrophenyl) and 1-(p-cyanophenyl)-5-arylpyrrole-2-propionic acid compounds

GB1091448A
(en)

1967-11-15

Novel d-threo-1-phenyl-2-aminopropan-1,3-diol derivatives and a process for their production

ES316418A1
(en)

1966-04-16

Process for the preparation of 2-nitroimidazoles

GB1057697A
(en)

1967-02-08

Penicillins

ES361113A1
(en)

1970-08-01

Aminoalkylbicyclocarboxylic acids

KR900018032A
(en)

1990-12-20

Method for preparing 2,3-dichloro-5-acetylpyridine

GB1419910A
(en)

1975-12-31

Synthesis of itaconic acid from 2,4,4-substituted-2-oxazolines and intermediates thereof

ES420666A1
(en)

1976-09-01

(1-methyl-5-nitro-2-imidazolyl)thioalkanoic acids and derivatives

GB1114018A
(en)

1968-05-15

Process for producing 4-hydroxycyclohexanecarboxylic acid and derivatives thereof

GB1292662A
(en)

1972-10-11

Bicycloheptaneheptanoic acids and esters thereof

GB1045544A
(en)

1966-10-12

New derivatives of pyrazolidines their production and use

GB1454529A
(en)

1976-11-03

Thiophene derivatives

GB1371155A
(en)

1974-10-23

Process for the manufacture of 6-methyl-uracil

GB1374981A
(en)

1974-11-20

Process for the production of bis-chromone-2-carboxylic acids and intermediates therefor

GB1315269A
(en)

1973-05-02

6-alpha-aryl substituted-2-amino-2-carboxyacylamino penicillanic acids and derivatives thereof

ES446764A2
(en)

1977-06-16

Procedure for the obtaining of derivatives of the fenoxy-acetic acid. (Machine-translation by Google Translate, not legally binding)

GB1382736A
(en)

1975-02-05

Process of producing semi-synthetic penicillin

GB1317257A
(en)

1973-05-16

4-thiazole carboxyldehyde derivatives

IT1039779B
(en)

1979-12-10

Esterifying fatty acids using tetraalkyl titanates – esp. useful for esters of conjugated unsatd. acids

NL7508728A
(en)

1977-01-25

Esterifying fatty acids using tetraalkyl titanates – esp. useful for esters of conjugated unsatd. acids

Download PDF in English