GB1136489A – Indoles
– Google Patents
GB1136489A – Indoles
– Google Patents
Indoles
Info
Publication number
GB1136489A
GB1136489A
GB44313/66A
GB4431366A
GB1136489A
GB 1136489 A
GB1136489 A
GB 1136489A
GB 44313/66 A
GB44313/66 A
GB 44313/66A
GB 4431366 A
GB4431366 A
GB 4431366A
GB 1136489 A
GB1136489 A
GB 1136489A
Authority
GB
United Kingdom
Prior art keywords
alkyl
alkoxy
hydrogen atom
radical
cyclo
Prior art date
1965-10-07
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
GB44313/66A
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.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
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.)
1965-10-07
Filing date
1966-10-04
Publication date
1968-12-11
1966-10-04
Application filed by Merck and Co Inc
filed
Critical
Merck and Co Inc
1968-12-11
Publication of GB1136489A
publication
Critical
patent/GB1136489A/en
Status
Expired
legal-status
Critical
Current
Links
Espacenet
Global Dossier
Discuss
Classifications
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07D—HETEROCYCLIC COMPOUNDS
C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
C07D209/04—Indoles; Hydrogenated indoles
C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
C07D209/18—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
C07D209/26—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 with an acyl radical attached to the ring nitrogen atom
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07D—HETEROCYCLIC COMPOUNDS
C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
C07D209/04—Indoles; Hydrogenated indoles
C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
C07D209/18—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
C—CHEMISTRY; METALLURGY
C07—ORGANIC CHEMISTRY
C07D—HETEROCYCLIC COMPOUNDS
C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
C07D209/04—Indoles; Hydrogenated indoles
C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
C07D209/18—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
C07D209/26—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 with an acyl radical attached to the ring nitrogen atom
C07D209/28—1-(4-Chlorobenzoyl)-2-methyl-indolyl-3-acetic acid, substituted in position 5 by an oxygen or nitrogen atom; Esters thereof
Abstract
1,136,489. Indoles. MERCK & CO. Inc. 4 Oct., 1966 [7 Oct., 1965], No. 44313/66. Heading C2C. Novel diesters of the general formula wherein A is a hydrogen atom or a substituted or unsubstituted carbocyclic or heterocyclic acyl radical preferably an aromatic carbocyclic or heterocyclic acyl radical containing less than three fused rings; R 1 is a hydrogen atom or C 1-5 alkyl, C 1-5 alkoxy, haloalkyl, hydroxyl, mercapto, benzylmercapto, benzyloxy, C 3-6 cyclo-alkyl, C 3-6 cyclo-alkoxy, di-(C 1-5 alkyl)- amino, bis-(C 1-5 hydroxyalkyl)-amino, pyrrolidino, morpholino, piperazino or C 2-5 alkenyl group; R 2 is a hydrogen atom or C 1-5 alkyl or C 1-5 alkoxy radical and R 3 is a bulky labile group subject to non-aqueous cleavage, e.g. t-butyl, are prepared by the interaction of the appropriate aniline, having not more than one substituent ortho to the nitrogen atom thereof and being free of deactivating, meta-directing, electron-attracting substituents, and a diester of γ-halo-#-keto adipic acid (wherein the esterifying radical is the group R 3 ) followed, optionally by acylation of the resulting 1-unsubstitutedindole compound. A process is also described which comprises cleaving the diacetate indole under non-aqueous conditions to form the corresponding unstable indole – 2,3 – diacetic acid which decarboxylates spontaneously thereby forming the corresponding α – (2 – methyl – 3 – indolyl) – acetic acid and, when required, acylating the latter compounds thus forming 1-acyl compounds having anti-inflammatory, antipyretic and analgesic activity.
GB44313/66A
1965-10-07
1966-10-04
Indoles
Expired
GB1136489A
(en)
Applications Claiming Priority (1)
Application Number
Priority Date
Filing Date
Title
US493885A
US3322786A
(en)
1965-10-07
1965-10-07
3-indolyl aliphatic acids
Publications (1)
Publication Number
Publication Date
GB1136489A
true
GB1136489A
(en)
1968-12-11
Family
ID=23962103
Family Applications (1)
Application Number
Title
Priority Date
Filing Date
GB44313/66A
Expired
GB1136489A
(en)
1965-10-07
1966-10-04
Indoles
Country Status (12)
Country
Link
US
(1)
US3322786A
(en)
BE
(1)
BE687885A
(en)
BR
(1)
BR6683338D0
(en)
CH
(2)
CH472405A
(en)
DE
(1)
DE1620039A1
(en)
DK
(1)
DK120542B
(en)
ES
(1)
ES332330A1
(en)
FR
(1)
FR1495978A
(en)
GB
(1)
GB1136489A
(en)
IL
(1)
IL26577A
(en)
NL
(1)
NL6614158A
(en)
SE
(2)
SE312805B
(en)
Families Citing this family (3)
* Cited by examiner, † Cited by third party
Publication number
Priority date
Publication date
Assignee
Title
CA957281A
(en)
*
1970-02-03
1974-11-05
Nathan N. Share
Pharmaceutical compositions containing indole-3-acetic acid derivatives as a skeletal muscle stimulant
DE3531658A1
(en)
*
1985-09-05
1987-03-12
Boehringer Mannheim Gmbh
HETEROCYCLICALLY SUBSTITUTED INDOLE, INTERMEDIATE PRODUCTS, METHOD FOR THEIR PRODUCTION AND MEDICINAL PRODUCTS
US5288743A
(en)
*
1992-11-20
1994-02-22
Abbott Laboratories
Indole carboxylate derivatives which inhibit leukotriene biosynthesis
1965
1965-10-07
US
US493885A
patent/US3322786A/en
not_active
Expired – Lifetime
1966
1966-09-26
IL
IL6626577A
patent/IL26577A/en
unknown
1966-09-30
BR
BR183338/66A
patent/BR6683338D0/en
unknown
1966-10-03
ES
ES0332330A
patent/ES332330A1/en
not_active
Expired
1966-10-04
GB
GB44313/66A
patent/GB1136489A/en
not_active
Expired
1966-10-04
CH
CH1428666A
patent/CH472405A/en
not_active
IP Right Cessation
1966-10-04
CH
CH66169A
patent/CH471123A/en
not_active
IP Right Cessation
1966-10-06
DE
DE19661620039
patent/DE1620039A1/en
active
Pending
1966-10-06
FR
FR79012A
patent/FR1495978A/en
not_active
Expired
1966-10-06
BE
BE687885A
patent/BE687885A/xx
unknown
1966-10-06
SE
SE13493/66A
patent/SE312805B/xx
unknown
1966-10-06
SE
SE01521/69A
patent/SE335127B/xx
unknown
1966-10-07
NL
NL6614158A
patent/NL6614158A/xx
unknown
1968
1968-04-10
DK
DK163868AA
patent/DK120542B/en
unknown
Also Published As
Publication number
Publication date
DK120542B
(en)
1971-06-14
BE687885A
(en)
1967-04-06
DE1620039A1
(en)
1970-02-05
US3322786A
(en)
1967-05-30
SE312805B
(en)
1969-07-28
NL6614158A
(en)
1967-04-10
CH471123A
(en)
1969-04-15
IL26577A
(en)
1970-12-24
FR1495978A
(en)
1967-09-22
ES332330A1
(en)
1967-07-16
SE335127B
(en)
1971-05-17
BR6683338D0
(en)
1973-12-04
CH472405A
(en)
1969-05-15
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