GB1150397A - New Indole-4-Acetic Acid Compounds and Methods for Their Production - Google Patents
New Indole-4-Acetic Acid Compounds and Methods for Their ProductionInfo
- Publication number
- GB1150397A GB1150397A GB784368A GB784368A GB1150397A GB 1150397 A GB1150397 A GB 1150397A GB 784368 A GB784368 A GB 784368A GB 784368 A GB784368 A GB 784368A GB 1150397 A GB1150397 A GB 1150397A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- acetic acid
- acid
- phenyl
- compound
- 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
Links
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
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Abstract
1,150,397. lndole-4-acetic acid compounds. PARKE DAVIS & CO. 16 Feb., 1968 [23 Feb., 1967], No. 7843/68. Heading C2C. Novel 1-substituted.indole-4-acetic acid compounds of the general formula and pharmaceutically-acceptable salts thereof; where R 1 is phenyl, mono(halo)phenyl, 2,3-dichlorophenyl, 2,4-dichlorophenyl, mono (lower alkyl) phenyl, methoxy phenyl, or cyclohexyl; R 2 is hydrogen, lower alkyl or phenyl, R 4 is hydrogen or lower alkyl; each of R 3 , R 5 and R 6 is hydrogen or methyl, with the further proviso that not more than one of R 3 , R 5 and R 6 is methyl; and A is a single bond or a double bond, are prepared by hydrolysing an ester compound having the general formula where R 1 , R 2 , R 3 , R 4 , R 6 , R 6 and A are as defined above and R<SP>1</SP> represents lower alkyl, preferably methyl or ethyl. The hydrolysis is carried out by heating a solution or suspension of the starting material in a solvent containing an acid or a base at a temperature between 0‹ and 120‹ C., or at the reflux temperature of the solvent, for 1-60 hours. The ester starting materials in the foregoing process may be prepared by reacting 4,5,6,7- tetrahydro - 4 - oxo - 3 - benzofurancarboxylic acid, 4,5,6,7 - tetrahydro - 3 - methyl - 4 - oxo - 2-benzofurancarboxylic acid, or 4,5,6,7-tetrahydro - 4 - oxo - 6 - methyl - 3 - benzofurancarboxylic acid with an amine having the formula R 1 -NH 2 followed by treatment of the resulting 4,5,6,7 - tetrahydro - 4 - iminoindole compound having the formula with acid to give a 6,7-dihydroindol-4(5H)-one compound having the formula or alternatively, by reaction of a 1,3-cycle hexanedione compound having the formula with an amine having the formula R 1 -NH 2 in acetic acid to give a 6,7-dihydroindol-4(5H)-one compound having the formula The 6,7-dihydroindol-4(5H)-one compounds are reacted with an α-haloacetic acid ester having the formula in the presence of zinc, followed by treatment of the reaction product with a strong acid to produce a 6,7-dihydroindole-4-acetic acid ester compound or a 6,7-dihydroindole-#<SP>4(5H)α</SP>-acetic acid ester compound or a mixture of both that can be represented by the formula which ester or mixture of esters is heated at an elevated temperature in a high-boiling point unreactive solvent in the presence of a dehydrogenating agent such as palladium on carbon, chloranil or sulphur, to produce an indole-4- acetic acid ester compound having the formula In the foregoing formulµ R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R<SP>1</SP> have the same meaning as above, R 7 is lower alkyl or phenyl and X represents chlorine, bromine or iodine. Pharmacological compositions containing the above free acid or salt forms possess antiinflammatory activity, and are administered orally or parenterally.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US61786467A | 1967-02-23 | 1967-02-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1150397A true GB1150397A (en) | 1969-04-30 |
Family
ID=24475362
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB784368A Expired GB1150397A (en) | 1967-02-23 | 1968-02-16 | New Indole-4-Acetic Acid Compounds and Methods for Their Production |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1150397A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0626946A1 (en) * | 1992-01-22 | 1994-12-07 | Zeneca Limited | N-phenylindole and n-pyridylindole derivatives, their preparation and their use as herbicides |
| WO1999062899A1 (en) * | 1998-06-04 | 1999-12-09 | Merck Sharp & Dohme Limited | Tetrahydroindolone derivatives as gabaaalpha5 ligands for enhancing cognition |
| WO2002070477A1 (en) * | 2001-03-01 | 2002-09-12 | Ono Pharmaceutical Co., Ltd. | 2-methylindole-4-acetic acid, process for producing the same, and process for producing intermediate therefor |
-
1968
- 1968-02-16 GB GB784368A patent/GB1150397A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0626946A1 (en) * | 1992-01-22 | 1994-12-07 | Zeneca Limited | N-phenylindole and n-pyridylindole derivatives, their preparation and their use as herbicides |
| US5599774A (en) * | 1992-01-22 | 1997-02-04 | Imperial Chemical Industries Plc | N-arylindoles and their use as herbicides |
| US5739353A (en) * | 1992-01-22 | 1998-04-14 | Zeneca Limited | N-arylindoles and their use as herbicides |
| WO1999062899A1 (en) * | 1998-06-04 | 1999-12-09 | Merck Sharp & Dohme Limited | Tetrahydroindolone derivatives as gabaaalpha5 ligands for enhancing cognition |
| US6395766B1 (en) | 1998-06-04 | 2002-05-28 | Merck Sharp & Dohme Limited | Tetrahydroindolone derivatives as gabaaalpha5 ligands for enhancing cognition |
| WO2002070477A1 (en) * | 2001-03-01 | 2002-09-12 | Ono Pharmaceutical Co., Ltd. | 2-methylindole-4-acetic acid, process for producing the same, and process for producing intermediate therefor |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |